US3754909A - Polyester coated paper as a conductive sheet material - Google Patents
Polyester coated paper as a conductive sheet material Download PDFInfo
- Publication number
- US3754909A US3754909A US00236192A US3754909DA US3754909A US 3754909 A US3754909 A US 3754909A US 00236192 A US00236192 A US 00236192A US 3754909D A US3754909D A US 3754909DA US 3754909 A US3754909 A US 3754909A
- Authority
- US
- United States
- Prior art keywords
- photoconductive
- sheet material
- paper
- composition
- conductive sheet
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000463 material Substances 0.000 title claims abstract description 49
- 229920000728 polyester Polymers 0.000 title description 22
- 229920001225 polyester resin Polymers 0.000 claims abstract description 57
- 239000004645 polyester resin Substances 0.000 claims abstract description 57
- 239000000203 mixture Substances 0.000 claims description 61
- -1 polyoxypropylene 2,2-bis(4-hydroxyphenyl) propane Polymers 0.000 claims description 47
- 229920005989 resin Polymers 0.000 claims description 46
- 239000011347 resin Substances 0.000 claims description 46
- 239000011230 binding agent Substances 0.000 claims description 23
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims description 19
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 19
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 18
- 229920005862 polyol Polymers 0.000 claims description 15
- 150000003077 polyols Chemical class 0.000 claims description 15
- 239000000049 pigment Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 229920001451 polypropylene glycol Polymers 0.000 claims description 12
- 229920001228 polyisocyanate Polymers 0.000 claims description 11
- 239000005056 polyisocyanate Substances 0.000 claims description 11
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 10
- 239000004606 Fillers/Extenders Substances 0.000 claims description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 3
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001260 acyclic compounds Chemical class 0.000 claims description 2
- 150000001334 alicyclic compounds Chemical class 0.000 claims description 2
- 239000000758 substrate Substances 0.000 abstract description 24
- 239000000123 paper Substances 0.000 description 69
- 239000002253 acid Substances 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 35
- 238000000034 method Methods 0.000 description 31
- 238000000576 coating method Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 239000011248 coating agent Substances 0.000 description 17
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000011888 foil Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 239000008199 coating composition Substances 0.000 description 7
- 150000003254 radicals Chemical group 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000001530 fumaric acid Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 2
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- FPAYXBWMYIMERV-UHFFFAOYSA-L disodium;5-methyl-2-[[4-(4-methyl-2-sulfonatoanilino)-9,10-dioxoanthracen-1-yl]amino]benzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1S([O-])(=O)=O FPAYXBWMYIMERV-UHFFFAOYSA-L 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 2
- 239000011953 free-radical catalyst Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 230000033458 reproduction Effects 0.000 description 2
- 239000012262 resinous product Substances 0.000 description 2
- 238000007761 roller coating Methods 0.000 description 2
- 229930187593 rose bengal Natural products 0.000 description 2
- 229940081623 rose bengal Drugs 0.000 description 2
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 2
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- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
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- 239000007787 solid Substances 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 2
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- IYNGLSRZLOHZJA-UHFFFAOYSA-N 1,4,7-triazabicyclo[5.2.2]undecane Chemical compound C1CN2CCN1CCNCC2 IYNGLSRZLOHZJA-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
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- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
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- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- PPRWTMVSNOOMDW-UHFFFAOYSA-N 3,5-dichloro-4-[2-(2,6-dichloro-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClC=1C=C(O)C=C(Cl)C=1C(C)(C)C1=C(Cl)C=C(O)C=C1Cl PPRWTMVSNOOMDW-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- ZDTNHRWWURISAA-UHFFFAOYSA-N 4',5'-dibromo-3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C(Br)=C1OC1=C(Br)C(O)=CC=C21 ZDTNHRWWURISAA-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- GDUYFVYTXYOMSJ-TXEJJXNPSA-N 4-[(2s,3r)-3-(4-hydroxyphenyl)butan-2-yl]phenol Chemical compound C1([C@H](C)[C@H](C)C=2C=CC(O)=CC=2)=CC=C(O)C=C1 GDUYFVYTXYOMSJ-TXEJJXNPSA-N 0.000 description 1
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 239000002635 aromatic organic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KSCQDDRPFHTIRL-UHFFFAOYSA-N auramine O Chemical compound [H+].[Cl-].C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 KSCQDDRPFHTIRL-UHFFFAOYSA-N 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000001761 ethyl methyl cellulose Substances 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- MKYIEPXEHPCWIH-UHFFFAOYSA-N formaldehyde;hydroxymethylurea Chemical compound O=C.NC(=O)NCO MKYIEPXEHPCWIH-UHFFFAOYSA-N 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 239000011086 glassine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229960001855 mannitol Drugs 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- VIJMMQUAJQEELS-UHFFFAOYSA-N n,n-bis(ethenyl)ethenamine Chemical compound C=CN(C=C)C=C VIJMMQUAJQEELS-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/10—Bases for charge-receiving or other layers
- G03G5/101—Paper bases
Definitions
- ABSTRACT An electrically conductive sheet material prepared from paper and a particular class of polyester resins is disclosed. The use of this conductive paper as the substrate in preparing a photoconductive recording sheet material is also disclosed.
- This invention relates to an electrically conductive sheet material. More particularly this invention relates to a conductive paper prepared from a polyester and paper which is useful as a conductive substrate in the preparation of photoconductive recording sheet material.
- xerography in the art of preparing photographic reproductions of originals by electrostatic printing techniques there are two distinct methods, a direct and an indirect process.
- the indirect process commonly called xerography, employs a reuseable drum which records, by electrostatic forces, the image which is to be printed and then transfers this image to a sheet of paper which is developed by depositing and fusing thereon a xerographic ink. This results in a clear reproduction of the original.
- xerographic ink in the direct process a sheet material which has the capability of accepting an electrostatic image directly from the original is used and an electrostatic ink, which can be identical to a xerographic ink, is then placed on the sheet material and the final copy prepared.
- the sheet material used in the direct electrostatic printing method is usually a multi-layer material.
- the most common type of sheet material uses as its base a light weight paper, such as a paper that weighs less than 50 pounds per ream, upon which a coating containing a photoconductive pigment such as zinc oxide is deposited.
- This sheet material can then receive an electrostatic image and be developed to produce a good copy of the original. It has been found in the practice of the direct process that paper by itself does not form a good conductive substrate for the photoconductive layer of a photoconductive recording material, i.e. photoconductive paper.
- paper does not form a good conductive substrate is that paper has a varying resistivity with humidity, and this resistivity may become too great or possibly too small to produce the proper electrical effect necessary for preparing a good electrostatic copy.
- conductive materials such as salts, acids, quaternary ammonium salts, and conductive polymers, which enhance the conductive property of the paper as a conductive substrate.
- the primary types of materials used in commercial photoconductive paper are conductive polymers which contain quaternary ammonium substituents. The exact mechanism by which the conductive polymer functions is not material to its effectiveness when used for photoconductive paper.
- any resin which would enhance the electrical conductivity of paper is a candidate for use in a conductive substrate. Not only must a resin or another material enhance the conductivity of the paper, it must also maintain a relatively constant conductivity in varying environments, especially with changing relative humidity.
- a suitable resin must also be relatively insoluble in organic solvents used in the preparation of the photoconductive layer. These solvents are toluene and similar aromatic hydrocarbon materials.
- Hm I in this formula 2 is 0 or 1;
- R is a radical selected from the group consisting of alkylene radicals containing from I to 5 carbon atoms, oxygen, sulfur,
- each E is individually either a halogen atom or a hydrogen atorn;
- m and n are integers frp m 0 through about 15 with the proviso that the sum of m and n is at least 7 and usually no more than about 30;
- X and Y are individually selected from the group consisting of methyl radicals and hydrogen atoms with the proviso that in any X and Y pair on adjacent carbon atoms either X or Y is hydrogen.
- a preferred conductive polyester resin the sum of the integers represented by m and n in said etherified diphenol will be at most 20 and at least 9.
- the etherified diphenols used are prepared from a diphenol.
- diphenols are 2,2-bis(4- hydroxyphenyl) propane; 2,3-bis(4-hydroxyphenyl) butane; 4,4-dihydroxydiphenol; 4,4'-dihydroxydiphenyl ether; bis(dichloro, difluoro-4-hydroxyphenyl) methane; 2,2-bis(2.6 dichloro-4-hydroxyphenyl) propane; bis( 2,3,5 ,6 tetrafluoro-4-hydroxyphenyl) sulfoxide; 3,3- bis(2,3,5,6-tetrabromophenyl) pentane; and 4- hydroxyphenyl-Z'-chloro-4-hydroxyphenyl ketone.
- the diphenols are etherified for use in accordance with the present invention. Etherification may be accomplished by the addition to the diphenol of ethylene oxide, propylene oxide or a mixture of same.
- the ether may also be prepared by reacting an olefin halohydrin with a diphenol as disclosed in U. S. Pat. No. 2,331,265. Methods of performing the reactions are well known in the art. It should be noted, however, that where mixtures of alcoholic and phenolic hydroxyl groups are present, the oxide compound reacts preferentially with phenolic hydroxyl groups. Thus, when an excess of an oxide compound is reacted with a diphenol, both phenolic hydroxyls are etherified prior to any extensive ether chains being formed.
- the preferred etherified diphenols within the class characterized by the above formula are the following etherified bisphenols: polyoxypropylene 2,2-bis(4- hydroxyphenyl) propane; polyoxyethylene 2,2-bis(4- hydroxyphenyl) propane; polyoxyethylene 2,2-bis(4- hydroxy-Z,6-dichloro-phenyl) propane; and polyoxypropylene 2,2-bis (4-hydroxy-2,o-dichlorophenyl) propane; wherein the number of polyoxyalkylene units per ylic acids are the following: phthalic acid, fumaric acid,
- a preferred group of acids include fumaric, maleic, and their anhydrides. Mixtures of dicarboxylic acids may also be used in which case it is preferred that at least 50 weight percent of the acids be unsaturated.
- the conductive polyesters used to make the products of this invention are prepared by the reaction of the etherified diphenol and the dicarboxylic acid, preferra bly in approximately stoichiometric amounts.
- the reaction may be performed in an inert atmosphere employing moderate temperatures and substantially atmospheric pressure during an early stage, to minimize the loss of dicarboxylic acid by volatilization. As the reaction proceeds the temperature may be increased and the pressure reduced.
- Esterification catalyst may be used although it is generally preferred to carry out the reaction in the absence of excessive amounts of catalyst to avoid contamination of the final resinous product. It is usually desirable to include a small amount of polymerization inhibitor such as hydroquinone, pyrogallol, or the lilte when an usaturated dicarboxylic acid is used.
- the reaction temperature for preparing the final polyesters of this invention will usually include heating to about 200C. for a portion of the reaction.
- the resulrant conductive polyesters usually have acid numbers less than about 30.
- the conductive polyesters preferrably are applied to the paper substrate by dispersing them in a liquid vehicle.
- Solvents such as aromatic hydrocarbons are usually suitable vehicles.
- Other examples are polyvinyl alcohol, isopropanol, water, and ethylene glycol monoethyl ether acetate.
- these conductive polyester resins which are not prone to becoming sticky when contacted with organic solvents, such as toluene and styrene, which are used as carriers for the photoconductive coatings applied to the conductive substrate, are those conductive polyester resins which have been modified with a modifying agent such as either an ethylenically unsaturated monomer, a polyfunctional hydroxy compound, a polyisocyanate, a dior triamine or an alkaline earth or alkali metal hydroxide.
- a modifying agent such as either an ethylenically unsaturated monomer, a polyfunctional hydroxy compound, a polyisocyanate, a dior triamine or an alkaline earth or alkali metal hydroxide.
- a modifying agent such as either an ethylenically unsaturated monomer, a polyfunctional hydroxy compound, a polyisocyanate, a dior triamine or an alkaline earth or alkali metal hydroxide.
- the ethylenically unsaturated monomers may be to modify only those conductive polyester resins of this invention which contain ethylenic unsaturation contributed by presence of unsaturated dicarboxylic acid residues. in general only homopolyrnerizable ethylenically unsaturated monomers are used.
- ethylenically unsaturated monomers which may be used are styrene, vinyl toluene, chlorostyrene, divinyl benzene, diallyl phthalate, acrylonitrile, methyl methacrylate, vinyl acetate, ethyl acrylate, alphamethyistyrene, vinyl pyridine, and Z-ethylhexyl acrylate.
- a conductive polyester resin is dissolved in the ethylenically unsaturated monomer which acts as both a vehicle for the conductive polyester and as a modifier.
- accelerators, or catalysts are usually added to the solution so that the polyester may be modified by copolymerizing with the ethylenically unsaturated monomer.
- catalysts include the kind frequently referred to as free radical catalysts, such as methyl ethyl ketone peroxide, benzoyl peroxide, tertiary butyl perbenzoate, cumene hydroperoxide, and succinic peroxide.
- free radical catalysts such as methyl ethyl ketone peroxide, benzoyl peroxide, tertiary butyl perbenzoate, cumene hydroperoxide, and succinic peroxide.
- accelerators are dimethyl aniline and cobalt naphthenate.
- the polyhydroxy compound when dispersed along with the conductive polyester resins within the class disclosed above is usually accompanied with an acidic catalyst to promote the cross-linking of the modifiers hydroxyl groups with residual hydroxyl and carboxyl groups of the conductive polyester resin. These catalysts include sulfonic acid, borontrifluoride etherate, sulfuric acid, hydrochloric acid, paratoluene sulfonic acid, and similar acid catalysts.
- the polyisocyanate modifications of the conductive polyester resins disclosed above are prepared by reacting the resins with sufficient isocyanate groups to react with residual hydroxyl groups of the conductive polyester resin.
- the minimum isocyanate group to residual hydroxyl group ratio is 1 but ratios as high as 3 yield acceptable modified conductive polyester resins.
- polyisocyanates which can be used in preparing the modified conductive polyester resins are toluene diisocyanate, diphenyl diisocyanate, chloro-phenyl-2,4-diisocyanate, 1,4-tetramethylene diisocyanate, para-phenylene-diisocyanate, 3,3-dimethyl-4,4'- phenylene diisocyanate, 3 ,3 '-dimethoxy-4,4 -diphenyl diisocyanate, polymethylene polyphenyl polyisocyanate (PAPI), methylene-bis(4,4'-polyphenyl polyisocyanate) (MONDUP MR), condensation product of a polyol and isocyanate for-example, the condensation product of 3 mols of toluene diisocyanate and 1 mol of trimethylol propane, urea condensed isocyanates such as the one sold under the tradename DESMODUR N and having the
- isocyanates can be used to cross-link the unsaturated or the saturated conductive polyester resins.
- po1yisocyanates contain an average of more than 2.5 isocyanate groups per molecule.
- the crosslinking may be aided by the addition of standard catalysts used in promoting urethane reactions. Exemplary of these catalysts are dibutyl tin dilaurate, trimethyl amine, N-methyl piperazine and N-methyl morpholine.
- the isocyanate and polyester are usually applied to the paper from an aromatic organic solvent such as benzene or toluene. However, where a catalyst is used the catalyst is usually added just prior to application to minimize crosslinking before application of the coating.
- the diand triamine and alkaline earth or alkali metal hydroxide modifications of the conductive polyester resins of this invention are prepared by mixing a conductive polyester resin with an amine or hydroxide at about room temperature and mixing for to 30 minutes.
- the conductive polyesters are usually liquid, but the conductive polyester-amine or inorganic salt mixture usually takes on a gel like consistency.
- the products are water soluble and relatively insoluble in aromatic hydrocarbons, and thus they may be applied from water solution.
- the amines are generally saturated acyclic, alicyclic, or aromatic.
- Exemplary of amines contemplated are triethylene diamine, cyclohexyldiamine, piperidine, hexamethylene triamine, tetraethylene triamine, and benzoguanamine.
- Exemplary of the hydroxides are calcium, barium, lithium, sodium, and potassium hydroxide.
- EXAMPLE 1 5,940 grams of polyoxypropylene(16)-2,2-bis (4- hydroxyphenyl) propane; 575 grams of fumaric acid; and 2 grams of hydroquinone are added to a fournecked, four-liter reaction vessel. This reaction mixture is purged with nitrogen and heated to 210C. The water of esterification is removed through a condenser as it is formed. The acid value of the reaction mixture is determined by the taking of hourly samples. When the acid value falls below 25, the reaction is stopped by removing the mixture from the heat source and pouring the reaction mixture into an open pan. The resulting polyester resin is a viscous liquid.
- EXAMPLE 2 3,460 grams of polyoxyethylene( 12)-2,2-bis(4- hydroxy-phenyl) propane; 540 grams of fumaric acid; and 2.0 grams of hydroquinone are placed in a 4- necked, 4-liter reaction vessel.
- the reaction mixture is heated with stirring to a temperature of 210C. 1- 5, and the reaction vessel is purged with nitrogen during the heat up period. Maintaining the 210C. and the inert nitrogen atmosphere, hourly samples of the reaction mixture are taken and when the acid value of the polyester reaches less than 25, the reaction mixture is removed from the heat and poured into an open pan for cooling. During the course of the reaction the water of esterification is continually removed.
- the resultant cooled resin is a viscous liquid polyester with an acid value of 19.2.
- EXAMPLE 3 According to the procedure of Example 1, 1,436 grams of polyoxypropylene(9)-2,2-bis(4- hydroxyphenyl) propane, 232 grams of fumaric acid, and 1.1 gram of hydroquinone are added to a 4-necked 4-liter reaction vessel. The reaction mixture is heated to 205C. and samples taken every hour and the acid value determined. When the acid value is determined to be less than about 20 the reaction vessel is removed from the heat source and the resin poured into an open pan for cooling. The resulting resin is a viscous liquid polyester.
- EXAMPLE 4 3,782 grams of polyoxypropylene(16)-2,2-bis(2,6- difluoro-4-hydroxyphenyl) propane and 434 grams of phthalic anhydride are added to a 4-liter, 4-necked reaction vessel and reacted according to the procedure of Example 2, at 205C. Hourly samples are removed from the reaction mixture and when the acid value is less than about 30 the resin is removed from the heat source and cooled in an open pan. The resulting polyester resin is a viscous liquid.
- EXAMPLE 5 According to the procedure of Example 1, 1,952 grams of polyoxyethylene(20)-4,4'-diphenyl ketone, 396 grams of glutaric acid, and 1.1 grams of hydroquinone are added to a 4-necked, 4-liter reaction vessel. The reaction is maintained at 200C. and hourly samples taken and the acid value of these samples determined. When the acid value is less than 20, the reaction mixture is removed from the heat source and cooled in an open pan. The resultant resin is a viscous liquid polyester resin.
- EXAMPLE 6 According to the procedure of Example 1, 583 grams of polyoxyethylene(9)-2,2-bis(4-hydroxyphenyl) propane, 540 grams of fumaric acid and 2 grams of hydroquinone are reacted at 210C. When the acid value of the reaction mixture reaches less than about 25 the reaction is stopped. The product is a viscous liquid resin with an acid value of 15.1.
- the conductive sheet material of this invention may be prepared by coating a paper, suitably a bond paper, similar to that described in U. S. Pat. No. 3,501,295, Column 5, line 5 3 through Column 6, line 43, with, for example, from 0.5 to 5.0 pounds of said conductive polyester resins per ream of paper; in which case the conductive polyester resin portion of the conductive substrate will be from about 1 to about 15 percent of the base paper.
- Papers used for preparing photoconductive paper include, for example glassine paper and paper sold by Riegel Paper Company under the Trade No. EC-38-XA and No. EC-35-XE.
- the conductive substrate of this invention is prepared by coating a sheet of paper with a conductive polyester composition, which may include a modifier, in a vehicle.
- a conductive polyester resin concentration will normally be from about 1 through 95 weight percent of said coating composition.
- the coating compositions applied by any standard paper coating method such as roller coating, size press, etc. depending upon the base paper stock used.
- the vehicle may be, for example, water or an organic aromatic compound such as benzene, toluene, or ethyl benzene. After application the coated paper is dried driving off the vehicle.
- film-extending materials are preferably incorporated in the solution. These materials may be added in a weight ratio of from 3 to 0.5 parts of film extender per part of conductive polyester resin.
- the viscosity of the final formulation that is, the polymer, the film extender, and the solvent, is adjusted so that the total viscosity is below 20,000 centipoises.
- an emulsifier to aid in dispersing the film extender in the vehicle.
- Exemplary of the emulsifiers are polyoxyethylene hexitol fatty acid esters, and polyoxyethylene hexitan fatty acid esters.
- Exemplary of film extenders are pigments, starches and rubber-like polymers; specific examples are TiO kaolin clay, butadiene-styrene copolymers, and low molecular weight polyethylene or polypropylene.
- a laboratory method of coating paper employs wire wound rods.
- a conductive polyester resin solution is poured onto the paper to be coated in one comer or at one edge of the paper.
- a wire wound rod is then passed across the paper starting at the solution containing edge. The thickness of the coating depends upon the wire thickness of the wire wound rod.
- the coated paper is then dried at between 50 and 120C. to remove all residual solvent.
- the resulting dry paper is relatively impenneable to organic solvents used for depositing the photoconductive zinc oxide compositions of the final photoconductive paper.
- Conductive substrates of this invention are prepared by using the above wire wound rod technique of spreading the resin on paper.
- the conductive resin may be applied as a conductive coating composition in a liquid vehicle as a solution or dispersion.
- the resins are dispersed or dissolved in the liquid vehicle by blending, mixing, stirring, or by other mechanical methods.
- a modifying agent, a catalyst, a film extender, or other additional ingredients which will make up part of the final coating are to be applied they are dissolved or dispersed with the conductive resin in the liquid vehicle.
- the conductive coating compositions Examples 7-20, which are tabulated Table I, are prepared by mixing all the ingredients into a vehicle, which is listed as the solvent in Table I.
- Table I lists various conductive coating compositions which are applied to either aluminum foil or paper. Examples 7 to which use aluminum foil are not representative of the conductive substrates of this invention but are used to illustrate the good conductive properties of the coatings used in accordance with this invention.
- a conductive coating is applied on a conductive substrate, such as aluminum foil as in Examples 7 to 15
- the conductive properties of the coating can be determined independently of the substrate by subjecting the coated aluminum foil to a voltage discharge of, for example, 9000 volts for about 5 seconds in a corona dishcarge unit capable of maintaining an 8500 to 9500 volt field. It will be found that no charge is accepted by the coated foil of Example 7-15. This result indicates that the resin coating is indeed very conductive.
- Examples 16-20 in Table I illustrate conductive substrates of particular conductive coating compositions on paper. These conductive substrates are prepared in accordance with the aforementioned coating procedure, and are electrically conductive sheet materials of this invention. When these conductive substrates are subjected to a corona discharge, in accordance with the procedure discussed above for coated aluminum foil, the charge acceptance is also zero.
- Procedure A A conductive polyester resin is dissolved in a solvent and coated on paper or aluminum foil using a wire wound rod supplied by R. D. Specialities of Webster, NY. The paper is then dried at C. to C. for 2 to 20 minutes resulting in a dry, flexible conductive paper or substrate.
- Procedure B A conductive polyester resin containing ethylenic unsaturation within the class of conductive polyester resins disclosed above is dissolved in ethylenically unsaturated monomer along with a free radical catalyst and the resulting solution is coated as in Procedure A on aluminum foil or paper sheets and cured at 100C. for 20 minutes.
- Procedure C A conductive polyester resin within the class of conductive polyester resins disclosed above is dispersed in water with an acid catalyst and polyhydroxy compound within the class disclosed above. This dispersion is coated as in Procedure A on aluminum foil or paper and cured for 30 minutes at 100 C.
- Procedure D A conductive polyester resin within the class disclosed above is mixed with a polyisocyanate in an aromatic hydrocarbon. This mixture is coated as in Procedure A on aluminum foil or paper and cured at room temperature for an hour.
- W is a mixture of 1 part benzoyl peroxide and 0.4 parts of dimethyl aniline by weight
- X is paratoluene sulfoncic acid
- Y is triethylene diamine
- Z is dibutyl tin dilaurate.
- Table I TDI toluene diisocyanate; HMM Hexamethylolmelamine; EG MBA-Ethylene glycol monoethyl ether acetate; PTDI condensation product of 3 mols of toluenediisocyanate and 1 mol of trimethylol propane; and EC-3S-XE A bond paper produced by the Reigel Paper Company. All quantities in Table l are parts by weight.
- Conductive coating contains 0.5 part of polyoxycthylene (20) sorbitan monooleatc as an emulsifier.
- a number of resins are available which may be used as binder resins in the photoconductive composition which comprises the top layer of a photoconductive paper.
- binder resins are silicone resins, cellulose esters (such as cellulose acetate, cellulose acetate butyrate, and cellulose nitrate), cellulose ethers (such as ethyl cellulose and methyl cellulose), polyvinyl acetate, polystyrene, acrylics, and polyesters.
- the photoconductive composition may in general be comprised of from about 15 parts to 2.5 parts of a photoconductive pigment per part by weight of binder resin.
- the ratio of photoconductive pigment to binder resin is from 9 to 5.
- Polyester resins which may be advantageously used as binder resins in a photoconductive composition, are those electrically insulating polyester resins prepared from a dicarboxylic acid and a polyol composition which comprises a short chain etherified dephenol, or a mixture of a dihydroxy alkane and a short chain etherified diphenol.
- tion may be represented by the following formula:
- alkylene radicals of l to 5 carbon atoms selected from the group consisting of alkylene radicals of l to 5 carbon atoms, oxygen, sulfur,
- A is individually selected from a halogen atom or hydrogen atom, the letters m and n are integers from 0 through 6 with the proviso that the sum of m and n is at least about 2 and less than 7;
- X and Y are radicals which are individually selected from the following group: alkyl radicals of l to 3 carbon atoms, a phenyl radical, or a hydrogen atom; provided that in any and Y pair an adjacent carbon atom either X or Y is a hydrogen atom.
- a preferred group of short chain etherified diphenols within the above formula include those where A is a chlorine atom or a hydrogen atom and/or R is an alkylene radical containing 1 to 3 carbon atoms and X'and Y are either hydrogen or a methyl radical. In this preferred group the average sum of n and m is at most about 3.
- polyoxypropylene(4)-4,4l'-bisphenol polyoxyethylene( 65 )-bis( 2,3 ,6-fluorodichloro-4- hydroxyphenyl) ether; polyoxyethylene(3.5)-4,4- bis(4-hydroxyphenyl) pentane; polyoxystyrene(4)- 2-fluoro-4-hydroxy-phenyl 4-hydroxypheny1 sulfoxide; and polyoxybutylene(2)-3,2-bis(2,3,6- tribromo-4-hydroxyphenyl) butane.
- polyester resins within the above class are those containing 2,2-bis(4-hydroxyphenyl) propane or the corresponding 2,6,2',6'-tetrachloro, tetrabromo, or tetrafluoro bisphenol alkoxylated with from two to four mols of propylene or ethylene oxide per mol of bisphenol.
- the dihydroxy alkanes which can be present at a level up to 60% by weight of the polyol composition used in preparing the non-conductive polyester resins of the photoconductive composition used to prepare electrofax paper in accordance with this invention are dihydroxy alkanes containing from 2 to 8 carbon atoms.
- a preferred group of dihydroxy alkanes include propylene glycol, ethylene gylcol, and neopentyl glycol.
- Examples of other dihydroxy alkanes which can be used include 1 ,3-dihydroxybutane, 1,4- dihydroxypentane, 1 ,Z-dihydroxyhexane, 2,3- dihydroxybutane, and 1,2-dihydroxyoctane.
- up to about 3 weight percent of said polyol composition can be comprised of a polyhydroxy alkane containing 3 to 6 carbon atoms and 3 to 6 hydroxyl groups or etherified derivatives of said polyhydroxy alkanes wherein the etherifying compounds are preferably ethylene or propylene oxide and there is up to 10 mols of oxide per hydroxyl group of said polyhydroxy alkane and preferably at least 1 mol of oxide per hydroxy group.
- polyhydroxy alkanes and the etherified polyhydroxy alkanes are sorbitol; erythritol, xylitol; pentaerythritol; 1,2,3-butane-tn'ol; l,2,5,6-hexanetetrol; polyoxyethylene(3) glycerol; polyoxypropylene(25) sorbitol; polyoxyethylene(6) 1,2,4,-butane-triol and polyoxypropylene(50) manni-- tol.
- the dicarboxylic acid used in preparing the non-conductive polyester resin may be saturated or unsaturated and may contain substituents such as halogen.
- these dicarboxylic acids are the following; phthalic acid, furmaric acid, maleic acid, isophthalic acid, malonic acid, glutaric acid, adipic acid, and the anhydrides of these acids.
- a preferred group of acids and anhydrides include fumaric, maleic, and succinic acids.
- the electrically insulating polyester resins are usually prepared by the reaction of a dicarboxylic acid with a polyol composition selected from those disclosed above.
- the reaction may be performed in an inert atmosphere employing moderate temperatures and substantially atmospheric pressures during the early stage, thus minimizing the loss of dicarboxylic acid by volatilization. As the reaction proceeds the temperature may be increased and the pressure reduced.
- Esterification catalyst may be used although it is generally preferred to carry out the reaction in the absence of excessive amounts of catalyst to avoid contamination of the final resinous product.
- an unsaturated dicarboxylic acid it is usually desirable to include a small amount of polymerization inhibitor such as hydroquinone, or pyrogallol.
- the reaction temperature required for preparing the final polyesters will usually include heating to about 200C.
- the resultant polyesters have low acid numbers; that is acid numbers less than about 30.
- the ratio of carboxyl groups and hydroxyl groups in the reaction mixture used for preparing the polyester resins of this invention is about 1. However, ratios as low as about 0.8 and as high as about 1.2 can readily be used.
- EXAMPLE 21 1,865 grams of polyoxypropylene(2.2)-2,2-bis(4- hydroxyphenyl) propane and 2.9 grams of polyoxypropylene(6)sorbitol are charged to a 3 liter, 4 necked, round-bottom reaction flask which is fitted with a thermometer, a stainlesssteel stirrer, a gas inlet tube, and a downward condenser. The flask is supported in a GLAS-COL electric heating mantle. Through the gas inlet tube nitrogen gas is allowed to flow sparging the polyol blend and resulting in an inert atmosphere in-the reaction vessel. The agitator and heating mantel are then activated and the polyol composition is heated to 50C.
- the resin has an acid value of 18.6, a ball and ring softening point of 104C., a tack point of C., and a liquid point of C.
- the ratio of hydroxyl groups and carboxyl groups in the preparation of this resin is 1 to 1.
- EXAMPLE 22 In accordance with the procedure of Example 1, 985 grams of polyoxyethylene( 3) bis( 4-hydroxyphenyl) ketone and 44.3 grams of polyoxyethylene(30) pentaerythritol are placed in a 3 liter, round-bottom flask. This mixture is heated and when the reaction temperature reaches 50C. 348 grams of succinic acid are added. The reaction mixture is then heated to a temperature of 215C. and the water of reaction is continually removed. The course of the reaction is followed by taking hourly samples in determining the acid value. After an acid value of 30 is reached the heat is removed and the reaction mixture is slowly cooled to room temperature. The resulting polyester is hard, tough and solid.
- EXAMPLE 23 According to the procedure of Example 1, 2190 grams of polyoxyethylene(2.5)-2,2-bis(4-hydroxy2,6- chlorophenyl) propane and 21 grams of polyoxyethylene(12) xylitol are placed in a 4 liter flask. This mixture is heated and when a temperature of 50C. is obtained, 465 grams of maleic acid is added. The heating is continued until a temperature of 210C. is achieved at which point the temperature is maintained at 210C. The water of esterification is removed as it is formed through a condenser. The acid value of the reaction mixture is tested at hourly intervals and when the acid number is less than 30, the reaction mixture is cooled to room temperature. The resultant polyester is a tough solid resin.
- EXAMPLE 24 pigment in a mechanical mixing device such as a rubber mill, ball mill or knife mill in the presence or absence of a solvent for the binder resin. Any other additives such as a sensitizer is added simultaneously.
- the photoconductive compositions may then be coated on conductive sheet material of this invention by standard paper coating techniques such as roller coating, size press, air knife or trailing blade coating.
- standard paper coating techniques such as roller coating, size press, air knife or trailing blade coating.
- the aforementioned wire wound rod technique is desirably used.
- Examples 25 to 36 tabulated in Table 11 illustrate photoconductive paper of the invention.
- the photoconductive composition listed in Table 11 are prepared by dissolving the electrically insulating polyester in one third of the solvent, i.e. toluene, and mixing the so formed solution with a slurry of the photoconductive pigment in the remaining two thirds of the solvent. This mixture is then charged to an 8580 Eberbach stainless steel container fitted for a WARlNG Blendor and ground to a finess of 5 to 6.5 of the N. S. Hegman scale.
- the parts listed in Table 11 are parts by weight.
- Examples 25-36 are exceptionally good photoconductive papers for the direct electrostatic process. When prints were prepared from the photoconductive paper illustrated in Table II, excellent clarity and black and white contrast are observed. This photoconductive paper can be used in any electrostatic direct process machine whether it is a dry or a wet developing machine.
- acid value is determined. When the acid value is less than 25 but more than 15, teh reaction mixture is removed from the heat source and allowed to cool to room temperature on a tray cooler. The final acid value for this resin in 16.4 and the resin exhibits a ball and ring softening point of 103C.
- sensitizers such as bromophenol blue, dibromofluorescein, acrydin yellow, rose bengal, disodium fluorescein, alizarin cyanine green GWA, and other sensitizers as illustrated in U. S. Pat. No. 3,245,735 at line 54, column 15.
- the sensitizer concentration will vary from about 0.01 to about 5.0 weight percent based upon the photoconductive material, with a preferred concentration of 0.01 to 0.1.
- the photoconductive compositions may be prepared by mixing the binder resin and the photoconductive
- the zinc oxide listed in Table 11 is photoconductive quality and sold under the trademark of PHOTOX zinc oxide.
- the sensitizer listed as part of the photoconductive composition in Table 11 is a mixture of bromophenol blue, disodium fluorescein, alizarin cyanine green GWA, and auramin 0 in a 1/l.4/l/0.1 weight ratio respectively and labeled sensitizer A or a 10 to 1 blend of rose bengal and bromophenol blue labeled sensitizer B.
- DE SOTO E041 a styrene-acrylic copolymer of DE SOTO Chemical Co.
- AROTAP 3201 an alkyd resin produced by Ashland Oil Co.
- GELVA 269 a vinyl polymer of the Monsanto Chemical Co.
- An electrically conductive sheet material which comprises paper coated with a conductive polyester resin of a dicarboxylic acid and an etherified diphenol wherein z is or 1; R is a radical selected from the group consisting of alkylene radicals containing from 1 to carbon atoms, oxygen, sulfur,
- each E is individually selected from a halogen atom or a hydrogen atom; m and n are integers from 0 through about with the proviso that the sum of m and n is at least 7.0 through about 30; and X and Y are individually selected from the group consisting of a methyl radical and a hydrogen atom with the proviso that in any X and Y pair on adjacent carbon atoms either X or Y is hydrogen.
- dicarboxylic acid is selected from unsaturated dicarboxylic acids and mixtures of unsaturated dicarboxylic acids containing at least about 50% unsaturated dicarboxylic acid and wherein in said etherified diphenol the sum of m and n is at most and at least 9.
- An electrically conductive sheet material according to claim 1 wherein the said etherified diphenol is selected from the group consisting of polyoxypropylene 2,2-bis(4-hydroxyphenyl) propane; polyoxyethylene 2,2-bis(4-hydroxyphenyl propane; polyoxyethylene 2,- 2-bis(4-hydroxy-2,6-dichloro-phenyl) propane; and polyoxypropylene 2,2-bis(4-hydroxy-2,6- dichlorophenyl) propane; and wherein the number of polyoxypropylene or polyoxyethylene units per mol of etherified diphenol is from 9 to 20.
- a modifying agent selected from the group consisting of an ethylenically unsaturated monomer, a polyfunctional hydroxy compound dispersible in aromatic hydrocarbons, a polyisocyanate, a dior triamine, and an alkaline earth or alkali metal hydroxide and wherein from 1 to 50 parts of modifying agent are present per 100 parts of the combination of polyester resin and modifying agent.
- An electrically conductive sheet material wherein said ethylenically unsaturated monomer is homopolymerizable, said polyisocyanate contains an average of more than 2.5 isocyanate groups per molecule, and said diand triamines are either saturated acyclic, alicyclic, or aromatic compounds.
- a photoconductive paper composition which comrial to said binder resin is from l5 to 2.5.
- a photoconductive paper composition which comprises an electrically conductive sheet material of claim 4 and a photoconductive composition coated thereon which comprises a photoconductive pigment and a binder resin wherein the weight ratio of said photoconductive material to said binder resin is from 15 to 2.5.
- a photoconductive paper composition which comprises an electrically conductive sheet material of claim 1 coated with a photoconductive composition comprising a photoconductive pigment and a binder resin wherein said binder resin is an electrically nonconductive polyester resin of a dicarboxylic acid and a polyol composition which contains a short chain etherified diphenol which may be represented by the formula:
- R is a radical selected from the group consisting of alkylene radicals of l to 5 carbon atoms, oxygen, sulfur,
- A is individually selected from a halogen atom or a hydrogen atom; the letters m and n are integers from 0 through 6 with the proviso that the sum of m and n is at least 2 and less than 7; and X and Y are radicals which are individually selected from the group consisting of alkyl radicals containing 1 to 3 carbon atoms, a phenyl radical, and a hydrogen atom, with the proviso that in any X and Y pair on adjacent carbon atoms either X or Y is a hydrogen atom.
- a photoconductive paper composition comprises the electrically conductive sheet material of claim 4 coated with a photoconductive composition consisting of a photoconductive pigment and binder resin wherein said binder resin is an electrically nonconductive polyester resin of a dicarboxylic acid and a polyol composition which contains a short chain etherified diphenol which may be represented by the formula:
- A is individually selected from a halogen atom or a hydrogen atom; the letters m and n are integers from 0 through 6 with the proviso that the sum of m and n is at least 2 and less than 7; and X and Y are radicals which are individually selected from the group consisting of alkyl radicals containing 1 to 3 carbon atoms, a phenyl radical, or a hydrogen atom, with the proviso that in any X and Y pair on adjacent carbon atoms either X or Y is a hydrogen atom.
Abstract
Description
Claims (11)
- 2. An electrically conductive sheet material according to claim 1 wherein said dicarboxylic acid is selected from unsaturated dicarboxylic acids and mixtures of unsaturated dicarboxylic acids containing at least about 50% unsaturated dicarboxylic acid and wherein in said etherified diphenol the sum of m and n is at most 20 and at least 9.
- 3. An electrically conductive sheet material according to claim 1 wherein the said etherified diphenol is selected from the group consisting of polyoxypropylene 2,2-bis(4-hydroxyphenyl) propane; polyoxyethylene 2,2-bis(4-hydroxyphenyl propane; polyoxyethylene 2,2-bis(4-hydroxy-2,6-dichloro-phenyl) propane; and polyoxypropylene 2,2-bis(4-hydroxy-2,6-dichlorophenyl) propane; and wherein the number of polyoxypropylene or polyoxyethylene units per mol of etherified diphenol is from 9 to 20.
- 4. An electrically conductive sheet material according to claim 1 wherein said conductive polyester resin has been modified with a modifying agent selected from the group consisting of an ethylenically unsaturated monomer, a polyfunctional hydroxy compound dispersible in aromatic hydrocarbons, a polyisocyanate, a di- or triamine, and an alkaline earth or alkali metal hydroxide and wherein from 1 to 50 parts of modifying agent are present per 100 parts of the combination of polyester resin and modifying agent.
- 5. An electrically conductive sheet material according to claim 4 wherein said ethylenically unsaturated monomer is homopolymerizable, said polyisocyanate contains an average of more than 2.5 isocyanate groups per molecule, and said di- and triamines are either saturated acyclic, alicyclic, or aromatic compounds.
- 6. An electrically conductive sheet material according to claim 1 wherein a film extending material is in admixture with said conductive polyester resin in a weight ratio of from 3 to 0.5 parts of film extender to polyester resin.
- 7. A photoconductive paper composition which comprises an electrically conductive sheet material of claim 1 coated with a photoconductive composition containing a photoconductive pigment and a binder resin wherein the weight ratio of said photoconductive material to said binder resin is from 15 to 2.5.
- 8. A photoconductive paper composition which comprises an electrically conductive sheet material of claim 4 and a photoconductive composition coated thereon which comprises a photoconductive pigment and a binder resin wherein the weight ratio of said photoconductive material to said binder resin is from 15 to 2.5.
- 9. A photoconductive paper composition which comprises an electrically conductive sheet material of claim 1 coated with a photoconductive composition comprising a photoconductive pigment and a binder resin wherein said binder resin is an electrically non-conductive polyester resin of a dicarboxylic acid and a polyol composition which contains a short chain etherified diphenol which may be represented by the formula:
- 10. A photoconductive paper composition which comprises the electrically conductive sheet material of claim 4 coated with a photoconductive composition consisting of a photoconductive pigment and binder resin wherein said binder resin is an electrically non-conductive polyester resin of a dicarboxylic acid and a polyol composition which contains a short chain etherified diphenol which may be represented by the formula:
- 11. A photoconductive paper composition according to claim 9 wherein said polyol composition includes up to 60 weight percent of a dihydroxy alkAne containing from 2 to 8 carbon atoms.
- 12. A photoconductive paper composition according to claim 9 wherein said polyol composition contains up to about 3 weight percent of a polyhydroxy alkane containing from 3 to 6 carbon atoms and from 3 to 6 groups or an ethylene or propylene oxide derivative of said polyhydroxy alkane, said derivative containing up to 10 mols of oxide per hydroxyl group of said polyhydroxy alkane.
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US23619272A | 1972-03-20 | 1972-03-20 |
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US00236192A Expired - Lifetime US3754909A (en) | 1972-03-20 | 1972-03-20 | Polyester coated paper as a conductive sheet material |
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Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3905813A (en) * | 1973-05-21 | 1975-09-16 | Ici America Inc | Low weight photoconductive compositions |
US3922448A (en) * | 1973-05-21 | 1975-11-25 | Ici America Inc | Water-soluble polyester resin electrographic coatings |
US3923509A (en) * | 1973-05-21 | 1975-12-02 | Ici America Inc | Water-soluble polyester resins as binders for photoconductors |
US3991256A (en) * | 1972-08-02 | 1976-11-09 | The Dow Chemical Company | Preparing electrostatographic printing sheet, article thereof and article coated with quaternary ammonium electroconductive resin |
US4182830A (en) * | 1978-07-24 | 1980-01-08 | Ici Americas Inc. | Vinyl ester urethanes |
US4271248A (en) * | 1980-01-28 | 1981-06-02 | Xerox Corporation | Magnetic latent image toner material and process for its use in flash fusing developing |
US4387211A (en) * | 1980-12-26 | 1983-06-07 | Kao Soap Co., Ltd. | Process for producing new polyester resin and product thereof |
US5302574A (en) * | 1992-12-23 | 1994-04-12 | Eastman Kodak Company | Thermal dye transfer receiving element with polyester/polycarbonate blended dye image-receiving layer |
US5317001A (en) * | 1992-12-23 | 1994-05-31 | Eastman Kodak Company | Thermal dye transfer receiving element with aqueous dispersible polyester dye image-receiving layer |
US5387571A (en) * | 1991-12-03 | 1995-02-07 | Eastman Kodak Company | Thermal dye transfer receiving element with polyester dye image-receiving |
US5441726A (en) * | 1993-04-28 | 1995-08-15 | Sunsmart, Inc. | Topical ultra-violet radiation protectants |
US5518812A (en) * | 1993-04-28 | 1996-05-21 | Mitchnick; Mark | Antistatic fibers |
US5770216A (en) * | 1993-04-28 | 1998-06-23 | Mitchnick; Mark | Conductive polymers containing zinc oxide particles as additives |
US6465097B1 (en) * | 1998-11-24 | 2002-10-15 | Sumitomo Electric Industries, Ltd. | Insulated wire |
-
1972
- 1972-03-20 US US00236192A patent/US3754909A/en not_active Expired - Lifetime
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3991256A (en) * | 1972-08-02 | 1976-11-09 | The Dow Chemical Company | Preparing electrostatographic printing sheet, article thereof and article coated with quaternary ammonium electroconductive resin |
US3905813A (en) * | 1973-05-21 | 1975-09-16 | Ici America Inc | Low weight photoconductive compositions |
US3922448A (en) * | 1973-05-21 | 1975-11-25 | Ici America Inc | Water-soluble polyester resin electrographic coatings |
US3923509A (en) * | 1973-05-21 | 1975-12-02 | Ici America Inc | Water-soluble polyester resins as binders for photoconductors |
US4182830A (en) * | 1978-07-24 | 1980-01-08 | Ici Americas Inc. | Vinyl ester urethanes |
US4271248A (en) * | 1980-01-28 | 1981-06-02 | Xerox Corporation | Magnetic latent image toner material and process for its use in flash fusing developing |
US4387211A (en) * | 1980-12-26 | 1983-06-07 | Kao Soap Co., Ltd. | Process for producing new polyester resin and product thereof |
US5387571A (en) * | 1991-12-03 | 1995-02-07 | Eastman Kodak Company | Thermal dye transfer receiving element with polyester dye image-receiving |
US5302574A (en) * | 1992-12-23 | 1994-04-12 | Eastman Kodak Company | Thermal dye transfer receiving element with polyester/polycarbonate blended dye image-receiving layer |
US5317001A (en) * | 1992-12-23 | 1994-05-31 | Eastman Kodak Company | Thermal dye transfer receiving element with aqueous dispersible polyester dye image-receiving layer |
US5441726A (en) * | 1993-04-28 | 1995-08-15 | Sunsmart, Inc. | Topical ultra-violet radiation protectants |
US5518812A (en) * | 1993-04-28 | 1996-05-21 | Mitchnick; Mark | Antistatic fibers |
US5770216A (en) * | 1993-04-28 | 1998-06-23 | Mitchnick; Mark | Conductive polymers containing zinc oxide particles as additives |
US6465097B1 (en) * | 1998-11-24 | 2002-10-15 | Sumitomo Electric Industries, Ltd. | Insulated wire |
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