WO2002059181A2 - Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof - Google Patents
Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof Download PDFInfo
- Publication number
- WO2002059181A2 WO2002059181A2 PCT/US2002/002148 US0202148W WO02059181A2 WO 2002059181 A2 WO2002059181 A2 WO 2002059181A2 US 0202148 W US0202148 W US 0202148W WO 02059181 A2 WO02059181 A2 WO 02059181A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydrocarbon
- polyether
- copolymer
- product
- block copolymer
- Prior art date
Links
- 229920006147 copolyamide elastomer Polymers 0.000 title description 17
- 229920001400 block copolymer Polymers 0.000 claims abstract description 101
- 239000002253 acid Substances 0.000 claims abstract description 96
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 85
- 229920000570 polyether Polymers 0.000 claims abstract description 82
- 229920001577 copolymer Polymers 0.000 claims abstract description 57
- 150000001412 amines Chemical class 0.000 claims abstract description 54
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 53
- 239000000376 reactant Substances 0.000 claims abstract description 52
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 47
- 150000004985 diamines Chemical class 0.000 claims abstract description 45
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 42
- 239000002904 solvent Substances 0.000 claims abstract description 41
- 239000000539 dimer Substances 0.000 claims abstract description 38
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 30
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims description 90
- 239000004952 Polyamide Substances 0.000 claims description 64
- 229920002647 polyamide Polymers 0.000 claims description 64
- 239000011347 resin Substances 0.000 claims description 63
- 229920005989 resin Polymers 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 33
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 29
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001033 ether group Chemical group 0.000 claims description 12
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 claims description 10
- 239000009261 D 400 Substances 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000004530 micro-emulsion Substances 0.000 claims description 5
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003916 ethylene diamine group Chemical group 0.000 claims 1
- 230000001166 anti-perspirative effect Effects 0.000 abstract description 7
- 239000003213 antiperspirant Substances 0.000 abstract description 7
- 239000000499 gel Substances 0.000 description 63
- 239000000047 product Substances 0.000 description 56
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 34
- -1 alkylnylene Chemical group 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 239000002798 polar solvent Substances 0.000 description 16
- 125000002947 alkylene group Chemical group 0.000 description 15
- 238000009472 formulation Methods 0.000 description 14
- 239000003349 gelling agent Substances 0.000 description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- 125000003368 amide group Chemical group 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 10
- 239000002781 deodorant agent Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 150000002334 glycols Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 229920002614 Polyether block amide Polymers 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 229940051250 hexylene glycol Drugs 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920001515 polyalkylene glycol Polymers 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- ZGUQGPFMMTZGBQ-UHFFFAOYSA-N [Al].[Al].[Zr] Chemical compound [Al].[Al].[Zr] ZGUQGPFMMTZGBQ-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000004450 alkenylene group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 125000005724 cycloalkenylene group Chemical group 0.000 description 4
- 125000002993 cycloalkylene group Chemical group 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 239000002453 shampoo Substances 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 150000002924 oxiranes Chemical group 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000006254 rheological additive Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229920000428 triblock copolymer Polymers 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- 241000640882 Condea Species 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- 229920005603 alternating copolymer Polymers 0.000 description 2
- HAMGNFFXQJOFRZ-UHFFFAOYSA-L aluminum;zirconium(4+);chloride;hydroxide;hydrate Chemical compound O.[OH-].[Al+3].[Cl-].[Zr+4] HAMGNFFXQJOFRZ-UHFFFAOYSA-L 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000021185 dessert Nutrition 0.000 description 2
- LVYZJEPLMYTTGH-UHFFFAOYSA-H dialuminum chloride pentahydroxide dihydrate Chemical compound [Cl-].[Al+3].[OH-].[OH-].[Al+3].[OH-].[OH-].[OH-].O.O LVYZJEPLMYTTGH-UHFFFAOYSA-H 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229910001651 emery Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
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- 239000002184 metal Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
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- 239000003784 tall oil Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
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- 239000001993 wax Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- YHBWXWLDOKIVCJ-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]acetic acid Chemical compound COCCOCCOCC(O)=O YHBWXWLDOKIVCJ-UHFFFAOYSA-N 0.000 description 1
- PIXJURSCCVBKRF-UHFFFAOYSA-N 2-amino-3-(5-tert-butyl-3-oxo-4-isoxazolyl)propanoic acid Chemical compound CC(C)(C)C=1ONC(=O)C=1CC([NH3+])C([O-])=O PIXJURSCCVBKRF-UHFFFAOYSA-N 0.000 description 1
- CZRCFAOMWRAFIC-UHFFFAOYSA-N 5-(tetradecyloxy)-2-furoic acid Chemical compound CCCCCCCCCCCCCCOC1=CC=C(C(O)=O)O1 CZRCFAOMWRAFIC-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
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- 239000004909 Moisturizer Substances 0.000 description 1
- 235000005128 Sapium sebiferum Nutrition 0.000 description 1
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- 239000001361 adipic acid Substances 0.000 description 1
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- 239000002386 air freshener Substances 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- DNXNYEBMOSARMM-UHFFFAOYSA-N alumane;zirconium Chemical class [AlH3].[Zr] DNXNYEBMOSARMM-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
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- 101150088806 atpA gene Proteins 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
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- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/042—Gels
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/88—Polyamides
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/90—Block copolymers
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
- A61L9/012—Deodorant compositions characterised by being in a special form, e.g. gels, emulsions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
- A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
- A61L9/12—Apparatus, e.g. holders, therefor
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/34—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids using polymerised unsaturated fatty acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides containing oxygen in the form of ether groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D9/00—Chemical paint or ink removers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09G—POLISHING COMPOSITIONS; SKI WAXES
- C09G1/00—Polishing compositions
- C09G1/06—Other polishing compositions
- C09G1/14—Other polishing compositions based on non-waxy substances
- C09G1/16—Other polishing compositions based on non-waxy substances on natural or synthetic resins
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J123/04—Homopolymers or copolymers of ethene
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J123/04—Homopolymers or copolymers of ethene
- C09J123/08—Copolymers of ethene
- C09J123/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
- C09J123/0869—Acids or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C5/00—Candles
- C11C5/002—Ingredients
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
- C11D17/0017—Multi-phase liquid compositions
- C11D17/0021—Aqueous microemulsions
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
- C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3719—Polyamides or polyimides
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3788—Graft polymers
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/173—Macromolecular compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/48—Thickener, Thickening system
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
Definitions
- This invention generally relates to organic resins, more particularly to resins having an internal structure comprised of polyamide and polyether, and terminal structure comprised of hydrocarbon.
- the invention also relates to the preparation of these resins, and their use as, for example, gelling agents for organic solvents.
- the consistency of the product is critical to its commercial success.
- personal care products which generally contain one or more active ingredients within a carrier formulation. While the active ingredient(s) determine the ultimate performance properties of the product, the carrier formulation is equally critical to the commercial success of the product in that it largely determines the consistency of the product.
- the rheology of the carrier also referred to as the "base" largely determines the flow properties of the product, and the flow properties largely determine the manner in which the consumer will apply or use the product.
- Polyamide resin prepared from polymerized fatty acid and diamine is reported to function as a gellant in formulations developed for personal care products.
- U.S. Patent No. 3,148,125 is directed to a clear lipstick carrier composition formed from polyamide resin compounded with a lower aliphatic alcohol and a so-called "polyamide solvent.”
- U.S. Patent No. 5,500,209 is directed to forming a gel or stick deodorant, where the composition contains polyamide gelling agent and a solvent system including monohydric or polyhydric alcohols.
- the prior art recognizes to blend certain poly amides with alcohols, to thereby form a gel.
- Polar solvents e.g., ether- and hydroxyl-containing materials which are liquid at or slightly above room temperature
- Polar solvents are desirably included in personal care formulations because they are often benign, allow dilution with at least some water, dissolve a wide range of active and inactive formulation ingredients and are relatively inexpensive.
- Polar solvents are also available in a wide variety of viscosities and grades. However, these solvents typically do not have the rheological properties that are desired in a carrier, e.g., they do not naturally exhibit gel-like character. Furthermore, gelants for this type of solvent are uncommon and often unavailable. Accordingly, there is a need in the art for materials that can be combined with solvents, and particularly polar solvents, to afford a transparent material that has gel-like character.
- the present invention provides this and related advantages as described herein. BRIEF SUMMARY OF THE INVENTION
- the present invention provides a block copolymer of the formula: hydrocarbon-polyether-polyamide-polyether-hydrocarbon.
- the present invention also provides compositions that include this block copolymer, where such compositions may also include one or more of a diacid, diamine or hydrocarbon- terminated polyether.
- R is selected from C 1 _ 22 hydrocarbon radicals
- R is selected from C 2.6 hydrocarbon diradicals
- R is selected from C 2.52 hydrocarbon diradicals, where at least 50% of the R 3 diradicals have at least 34 carbons
- R 4 is selected from C 2.36 hydrocarbon diradicals and C 4 -C 100 polyether diradicals
- Z is selected from O and NH
- x is an integer from 2 to 100
- y is an integer from 1 to 10
- Z is NH
- R is a C 2 hydrocarbon diradical
- at least 80% of the R 3 diradicals have at least 34 carbon atoms.
- the present invention provides a composition that includes a copolymer as described above, that meets one or more of the following criteria: an acid number of less than 25; an amine number of less than 5; a softening point of 50-150°C; a weight average molecular weight of 2,000 to 20,000; a melting point above 50°C and a viscosity at 160°C of less than 5,000 cps.
- the present invention provides a gelled composition that includes a hydrocarbon-terminated block copolymer as described above, and a polar organic solvent, the solvent having hydroxyl and/or ether functionality.
- the present invention provides a method for preparing a gel, where the method includes combining a hydrocarbon-terminated block copolymer as described above, at elevated temperature with a liquid having hydroxyl and/or ether functionality to provide a mixture, and allowing the mixture to cool to room temperature to form the gel.
- a hydrocarbon group contains only carbon and hydrogen atoms.
- a polyether groups contains 2 or more ether groups, t.e., groups of the formula hydrocarbon-O-hydrocarbon, where the hydrocarbon of one ether group can also serve as the hydrocarbon of another ether group.
- R in the amide group is determined by the choice of diamine used in the preparation of the polyamide block of the block copolymer of the present invention.
- at least one amide group of the polyamide is flanked by polyether groups, while in another aspect all of the amide groups in the polyamide block are flanked by hydrocarbon groups.
- Suitable hydrocarbon groups are formed from one or more of aliphatic and aromatic moieties. Suitable aliphatic moieties are alkyl, alkylene, alkenyl, alkenylene, alkynyl, alkylnylene, cycloalkyl, cycloalkylene, cycloalkenyl, cycloalkenylene, cycloalkynyl, and cycloalkynylene moieties. Aromatic moieties are also referred to herein as aryl groups.
- the hydrocarbon groups that terminate the block copolymers of the present invention will be referred to herein as R 1 .
- the block copolymer of formula (1) contains at least two polyether blocks.
- a polyether block contains a plurality of ether groups, i.e., groups of the formula -C-O-C-.
- a polyether block contains the repeating
- R is a hydrocarbon group.
- R is an alkylene group.
- the alkylene group R may be aliphatic (saturated and/or unsaturated) or aromatic, straight chain and/or branched, independently at each occurrence in the polyether block.
- R has 1-6 carbons at each occurrence in the polyether
- Dimer acid typically contains some byproducts of the fatty acid polymerization process.
- One common byproduct is so-called trimer acid, which results when three fatty acid molecules react together to form a C 64 tricarboxylic acid.
- trimer acid which results when three fatty acid molecules react together to form a C 64 tricarboxylic acid.
- trimer acid it may happen, in the preparation of a block copolymer of the present invention, that two of the carboxylic acid groups of trimer acid will react with, e.g., a diamine, leaving one carboxylic acid group unreacted.
- the block copolymer will contain a carboxylic acid-substituted R group, which is technically not a hydrocarbon.
- a co-diacid is a compound of formula HOOC-R 3 -COOH where R 3 is not C 34 as defined above.
- the polyamide block in copolymers of formula (1) includes R 3 groups having 2-32 carbons, which are referred to herein a co-diacid R groups.
- Suitable co-diacid R groups include ethylene (from, e.g., succinic acid) and n-butylene (from, e.g., adipic acid).
- the C 34 R groups constitute at least 50 mol% of the total of the R 3 groups.
- the block copolymer contains 0 ester groups (e.g., when the polyether is amine terminated rather than hydroxyl terminated), or no more than 1 ester group (when a mixture of amine terminated and hydroxyl terminated polyether are used), or no more than 2 ester groups.
- the present invention provides a composition comprising a hydrocarbon-terminated polyether-polyamide block copolymer of the present invention having an amine number of less than 25, or less than 20, or less than 15, or less than 10, or less than 5 or less than 2 or less than 1.
- the hydrocarbon-terminated polyether- polyamide block copolymer of formula (1) does not have any free amine groups, and accordingly has an amine number of zero.
- some of the diamine may not react with the diacid, and according the final product may have some unreacted amine groups that will be responsible for the product having an amine number greater than zero.
- block copolymers are prepared from compounds of
- propylene glycol is a preferred solvent to prepare gels from solvent and resins of the invention (t.e., resins prepared from polyether diamine and polyether • monoamine).
- resins of the invention t.e., resins prepared from polyether diamine and polyether • monoamine.
- dimer-acid based polyamides even those including a significant level of both polyether diamine and polyether monoamine among the reactants leads to a resin that it not particularly compatible with glycerol.
- a polyether diamine and polyether monoamine-derived resin is dissolved in a polar solvent, and then this solution is diluted with water, it is typically observed that the solution remains homogeneous, t.e., the resin does not precipitate.
- the diamine may be a mixture of hydrocarbon diamine and polyether diamine.
- HMD A hexamethylene diamine
- EDA ethylene diamine
- ethylene diamine is a reactant used in preparing the block copolymer, and in particular is used in preparing the polyamide block of the block copolymer.
- EDA is blended with a polyetherdiamine, in order to prepare the polyamide block of the block copolymer of the present invention, where the diamine(s) are reacted with diacid, e.g., dimer acid.
- diamines, dicarboxylic acids, and hydrocarbon- terminated polyethers having a reactive group W selected from hydroxyl, amine and carboxyl are preferred starting materials to form the triblock copolymers of the invention.
- These starting materials are preferably reacted together with a stoichiometry, and under reaction conditions, such that the acid number of the resulting block copolymer is less than 25, preferably less than 15, and more preferably less than 10, while the amine number is preferably less than 10, more preferably less than 5, and still more preferably less than 1.
- the softening point of the block copolymer is preferably greater than room temperature, more preferably is about 50°C to about 150°C, and still more preferably is about 75°C to about 125°C.
- Gels prepared with block copolymers of the present invention may be anywhere from soft to hard, where a "hard” gel has a rigid structure and is very resistant to deformation, while a “soft” gel exhibits some, but not too much, resistance to deformation.
- An illustration of "soft” gel may be seen in the preparation of Jell-O ® dessert, which is a well known food product from Kraft Foods Inc. (division of Philip Morris Companies Inc., Northfield, IL). When prepared according to the package instructions, Jell-O ® dessert is mixed with water to form a relatively soft gel.
- a preferred solvent is a polar solvent, where exemplary polar solvents include lower alcohols (e.g., methanol, ethanol, propanol, butanol), glycols, ethers, glycol ethers (t.e., polyalkyleneglycol ethers), and polyols.
- the polar solvent may be a mixture of solvents. Exemplary polar solvents are described in TABLE E (TABLE E - POLAR SOLVENTS CONTAINING HYDROXYL AND/OR ETHER FUNCTIONALITIES).
- the gels containing block copolymer of the present invention are also stable, in that they do not display syneresis.
- syneresis is the spontaneous separation of a liquid from a gel or colloidal suspension due to contraction of the gel.
- syneresis is observed as the separation of liquid from a gel, and is sometimes referred to as "bleeding", in that wetness is seen along the surfaces of a gel that displays syneresis.
- syneresis is typically an undesirable property, and the gels of the present invention desirably, and surprisingly do not exhibit syneresis.
- the gels of the invention, and articles prepared therefrom may be stable in the sense that they do not exhibit syneresis. Thus, they do not have an oily feeling when handled.
- the block copolymer of the invention may be incorporated into commercial products such as those listed above, as well as cable filling compounds, urethane/alkyl paint additives, and soaps/surfactants. These products may be prepared by blending the block copolymer with the other components of the product. In these commercial products, the block copolymer will typically be present at a concentration of about 1% to about 50% of the composition, based on the total weight of the composition. It is a routine matter to optimize the amount of block copolymer in a composition, and indeed the amount will vary depending on the actual product and the desired consistency of the product. In general, as more block copolymer is used in a formulation, the product will display a more pronounced gel character, and will form a more rigid, or hard, gel.
- EMPOLTM dimer acid is available from Henkel Corporation, Emery Oleochemicals Division (Cincinnati, OH; http://www.henkelcorp.com).
- Ethylene diamine (EDA) is available from Aldrich (Milwaukee, WI; www.sigma-aldrich.com).
- NEODOLTM alcohol ethoxylates are available from Shell Chemical Company (Houston, TX; www.shell.com).
- EXAMPLE 1 HYDROCARBYL ETHOXYLATE-TERMINATED BLOCK COPOLYMER
- the product block copolymer was characterized and found to have an acid number of 18.3 (higher than the theoretical value of 6, indicating incomplete reaction of the alcohol ethoxylate), an amine number of 1.1, a softening point of 9,0.3 °C and a viscosity at 160°C of 85 cPs.
- Example 1 The procedure of Example 1 was followed using 47.8 parts EMPOLTM 1008 (100 eq.% acid), 2.8 parts EDA (56.2 eq.% amine + hydroxyl, based on acid equivalents) and 49.4 parts NEODOLTM 45-13 (37.4 eq.% amine + hydroxyl, based on acid equivalents).
- the product had an acid number of 21.4 (higher than the theoretical value of 6, indicating incomplete reaction of the alcohol ethoxylate), an amine number of 0.4, a softening point of 83.7°C and a viscosity at 160°C of 67 cPs.
- Example 1 The procedure of Example 1 was followed using 61.8 parts EMPOLTM 1008 (100 eq.% acid), 4.3 parts EDA (66.5 eq.% amine + hydroxyl, based on acid equivalents) and 33.9 parts MPEG 550 (28.5 eq.% amine + hydroxyl, based on acid equivalents).
- the product had an acid number of 20.5 (higher than the theoretical value of 6, indicating incomplete reaction of the alcohol ethoxylate), an amine number of 1.0, a softening point of 91°C and a viscosity at 160°C of 52 cPs.
- the gelling behavior of this block copolymer is described in Example 8. At high termination levels (see Examples 6 and 7), the properties of the block copolymer are dominated by the polyalkyl glycol.
- the gel characteristics are related to the level of termination and the density of amide groups.
- the use of HMDA versus EDA increased the hardness of the gels in propylene glycol.
- the clearest and hardest gels are obtained by using HMDA and the maximum level of termination possible.
- Resins having high levels of M-2070 were slightly soluble in water (at concentrations up to about 3-4%). Thus, these resins are extremely hydrophilic materials and demonstrate some surfactant properties.
- a preferred range of termination, using M-2070, is about 15-18 eq.% with a co-diamine level of about 45-48 eq.% (more than this results in a clear, but mobile "jelly").
- the polyoxyalkyleneamine may have the structure of JEFFAMINE M2070.
- the polyoxyalkyenediamine may have the formula H 2 N-[(R a -O) n -(R b -O) -R c -NH 2 where (R a -O) n -(R b -O) m represents a plurality of R a -O and R b -O units arranged in any sequence, the sum of n and m provides a molecular weight of 200 to 800 g/mol and either m or n may be zero, R a is -CH 2 CH 2 -, R b is -CH(CH 3 )-CH 2 -, and R c is selected from R a and R b .
Abstract
Description
Claims
Priority Applications (9)
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KR1020037009819A KR100775189B1 (en) | 2001-01-24 | 2002-01-24 | Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof |
AU2002240081A AU2002240081A1 (en) | 2001-01-24 | 2002-01-24 | Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof |
BR0206701-3A BR0206701A (en) | 2001-01-24 | 2002-01-24 | Hydrocarbon-terminated polyether polyamide block copolymers and uses thereof |
EP02705967A EP1358248B1 (en) | 2001-01-24 | 2002-01-24 | Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof |
MXPA03006588A MXPA03006588A (en) | 2001-01-24 | 2002-01-24 | Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof. |
DE60206879T DE60206879T2 (en) | 2001-01-24 | 2002-01-24 | HYDROCARBON END-POLYETHERMAL POLYAMIDE BLOCK COPOLYMERS AND THEIR USE |
JP2002559476A JP4040974B2 (en) | 2001-01-24 | 2002-01-24 | Hydrocarbon-terminated polyether polyamide block copolymers and uses thereof |
CA002435428A CA2435428C (en) | 2001-01-24 | 2002-01-24 | Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof |
AT02705967T ATE307844T1 (en) | 2001-01-24 | 2002-01-24 | POLYETHER-POLYAMIDE BLOCK COPOLYMERS CONTAINING HYDROCARBON END GROUPS AND THEIR APPLICATION |
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US09/769,081 | 2001-01-24 | ||
US09/769,081 US6399713B1 (en) | 2001-01-24 | 2001-01-24 | Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof |
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US (1) | US6399713B1 (en) |
EP (2) | EP1616896B1 (en) |
JP (1) | JP4040974B2 (en) |
KR (1) | KR100775189B1 (en) |
AT (2) | ATE382067T1 (en) |
AU (1) | AU2002240081A1 (en) |
BR (1) | BR0206701A (en) |
CA (1) | CA2435428C (en) |
DE (2) | DE60224309T2 (en) |
ES (2) | ES2300911T3 (en) |
MX (1) | MXPA03006588A (en) |
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US8013021B2 (en) | 2001-01-24 | 2011-09-06 | Arizona Chemical Company, Llc | Hydrocarbon-terminated polyether-polyamide block copolymer and uses thereof |
EP1504050A1 (en) * | 2002-05-08 | 2005-02-09 | Arizona Chemical Company | Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof |
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US8114424B2 (en) | 2003-03-20 | 2012-02-14 | Arizona Chemical Company, Llc | Polyamide-polyether block copolymer |
US8114387B2 (en) | 2003-03-20 | 2012-02-14 | Arizona Chemical Company, Llc | Polyamide-polyether block copolymer |
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JP2006520835A (en) * | 2003-03-20 | 2006-09-14 | アリゾナ・ケミカル・カンパニー | Polyamide-polyether block copolymer |
US9668472B2 (en) | 2012-11-01 | 2017-06-06 | Huntsman Petrochemical Llc | Polyamide and polyimide sticker adjuvants |
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Also Published As
Publication number | Publication date |
---|---|
DE60206879T2 (en) | 2006-07-20 |
MXPA03006588A (en) | 2004-10-15 |
DE60224309T2 (en) | 2008-12-11 |
CA2435428A1 (en) | 2002-08-01 |
EP1358248B1 (en) | 2005-10-26 |
KR100775189B1 (en) | 2007-11-12 |
AU2002240081A1 (en) | 2002-08-06 |
ATE307844T1 (en) | 2005-11-15 |
JP4040974B2 (en) | 2008-01-30 |
EP1616896B1 (en) | 2007-12-26 |
CA2435428C (en) | 2008-07-22 |
DE60224309D1 (en) | 2008-02-07 |
KR20030094238A (en) | 2003-12-11 |
PT1616896E (en) | 2008-04-07 |
WO2002059181A3 (en) | 2003-03-27 |
JP2004518006A (en) | 2004-06-17 |
DE60206879D1 (en) | 2005-12-01 |
US6399713B1 (en) | 2002-06-04 |
EP1358248A2 (en) | 2003-11-05 |
EP1616896A1 (en) | 2006-01-18 |
ATE382067T1 (en) | 2008-01-15 |
ES2250619T3 (en) | 2006-04-16 |
ES2300911T3 (en) | 2008-06-16 |
BR0206701A (en) | 2004-12-28 |
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