US3799956A - Surface active agent and method of preparing the same - Google Patents
Surface active agent and method of preparing the same Download PDFInfo
- Publication number
- US3799956A US3799956A US00080030A US8003070A US3799956A US 3799956 A US3799956 A US 3799956A US 00080030 A US00080030 A US 00080030A US 8003070 A US8003070 A US 8003070A US 3799956 A US3799956 A US 3799956A
- Authority
- US
- United States
- Prior art keywords
- surface active
- active agent
- ethylene oxide
- alcohol
- moles
- 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
- 239000004094 surface-active agent Substances 0.000 title abstract description 45
- 238000000034 method Methods 0.000 title description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 28
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract description 14
- 230000000694 effects Effects 0.000 abstract description 7
- 238000005187 foaming Methods 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 5
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- -1 coconut alcohol Chemical compound 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 5
- 125000006353 oxyethylene group Chemical group 0.000 description 5
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002216 antistatic agent Substances 0.000 description 3
- 229960000541 cetyl alcohol Drugs 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940096386 coconut alcohol Drugs 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000011874 heated mixture Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000003921 oil 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
- 239000002994 raw material Substances 0.000 description 2
- 229940012831 stearyl alcohol Drugs 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- QBOZYKRSDXSADT-UHFFFAOYSA-N (2,3,4-tributylphenyl) dihydrogen phosphite Chemical compound CCCCC1=CC=C(OP(O)O)C(CCCC)=C1CCCC QBOZYKRSDXSADT-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- CZTSOXCSVFEFIK-UHFFFAOYSA-N 2-benzylnaphthalen-1-ol Chemical group C1=CC2=CC=CC=C2C(O)=C1CC1=CC=CC=C1 CZTSOXCSVFEFIK-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 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
- 239000005639 Lauric acid Substances 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RRTCFFFUTAGOSG-UHFFFAOYSA-N benzene;phenol Chemical compound C1=CC=CC=C1.OC1=CC=CC=C1 RRTCFFFUTAGOSG-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000009747 press moulding Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012629 purifying agent Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KXDRRFQARLPIBW-UHFFFAOYSA-N tris(2-chlorophenyl) phosphite Chemical compound ClC1=CC=CC=C1OP(OC=1C(=CC=CC=1)Cl)OC1=CC=CC=C1Cl KXDRRFQARLPIBW-UHFFFAOYSA-N 0.000 description 1
- BKHZQJRTFNFCTG-UHFFFAOYSA-N tris(2-methylphenyl) phosphite Chemical compound CC1=CC=CC=C1OP(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C BKHZQJRTFNFCTG-UHFFFAOYSA-N 0.000 description 1
- RMLPZKRPSQVRAB-UHFFFAOYSA-N tris(3-methylphenyl) phosphate Chemical compound CC1=CC=CC(OP(=O)(OC=2C=C(C)C=CC=2)OC=2C=C(C)C=CC=2)=C1 RMLPZKRPSQVRAB-UHFFFAOYSA-N 0.000 description 1
- FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/78—Neutral esters of acids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/1411—Esters of phosphorous acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
Definitions
- R is a conventional nonionic surface active agent residue to which ethylene oxide or both ethylene oxide and propylene oxide is added, and R and R are a con ventional nonionic surface active agent residue to which ethylene oxide or both ethylene oxide and propylene oxide is added or an alkyl group having 8 to 22 carbon atoms and its preparation are described.
- the surface active agent is superior in surface activity, heat-resisting stability and a reduced foaming property.
- This invention relates to a novel surface active agent and a method of preparing the same.
- An object of the present invention is to provide a novel surface active agent which has superior surface activities, a heat-resisting stability and a reduced foaming property.
- the surface active agent of the present invention comprises a compound having the following general formula:
- R is a conventional nonionic surface active agent residue to which one or more moles of ethylene oxide or one or more moles of both ethylene oxide and propylene oxide is added
- R and R are a member selected from the group consisting of a conventional nonionic surface active agent residue to which one or more moles of ethylene oxide or one or more moles of both ethylene oxide and propylene oxide is added and an alkyl group having 8 to 22 carbon atoms.
- the above conventional nonionic surface active agent includes, for example, (1) a nonionic surface active agent of such a type as an addition product of l to 100 moles of ethylene oxide or 1 to 100 moles of both ethylene oxide and propylene oxide to one mole of higher alcohol having 8 to 22 carbon atoms such as octyl alcohol, lauryl alcohol, coconut alcohol, cetyl alcohol, stearyl alcohol, oleyl alcop CC hol, tridecyl alchol, etc.; (2) that of such a type as an addition product of 1 to moles of ethylene oxide or 1 to 100 moles of both ethylene oxide and propylene oxide to one mole of alkyl phenol containing an alkyl group having 4 to 22 carbon atoms such as butyl phenol, octyl phenol, nonyl phenol, dodecyl phenol, dinonyl phenol, etc.; (3) that of such a type as an addition product of 1 to 100 moles of ethylene oxide or 1 to 100 moles
- the surface active agent of the present invention is prepared by the following method:
- the compound wherein all of R R and R in the above formula are conventional surface active agent residues, is prepared by reacting one mole of triaryl phosphite or trichloroaryl phosphite with at least about 3 moles of a conventional surface active agent using a strong basic catalyst, which results in ester interchange of the former with the latter.
- the compound wherein one or two of R and R in the formula are alkyl groups having 8 to 22 carbon atoms is prepared by reacting one mole of triaryl phosphite or trichloroaryl phosphite with at least about three moles of both conventional surface active agent and higher alcohol, wherein the mole ratio of the surface active agent to the higher alcohol is approximately /2 to 2, using a strong basic catalyst.
- a strong basic catalyst which is used in the present invention, includes, for example, metal alcoholates such as sodium methylate, potassium phenolate, etc.; quaternary ammonium hydroxides; inorgamc strong bases such as sodium hydroxide, potassium hydroxide, etc; and alkali metals such as sodium, potassium, etc.
- metal alcoholates such as sodium methylate, potassium phenolate, etc.
- quaternary ammonium hydroxides such as sodium hydroxide, potassium hydroxide, etc
- alkali metals such as sodium, potassium, etc.
- the proportion of the basic catalyst from 0.001 to 0.20 mole based on the moles of triaryl phosphite or trichloroaryl phosphite is preferable.
- Triaryl phosphite or trichloroaryl phosphite which is used in the present invention, includes, for example, triphenyl phosphite, tri-p-cresyl phosphite, tri-o-cresyl phosphite, tri-m-cresyl phosphite, tri-butylphenyl phosphite, tri-o-chlorophenyl phosphite, tri-p-chlorophenyl phosphite, tri-m-chlorophenyl phosphite, etc.
- the higher alcohol which is used in the present invention, is a saturated or unsaturated alcohol containing an 3 alkyl group having 8 to 22 carbon atoms which includes, for example, octanol, decanol, lauryl alcohol, myristyl alcohol, palmityl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, coconut alcohol, tridecyl alcohol, etc.
- the ester interchange reaction of the present invention is effected at a temperature of 100 to 250 C. under atmospheric or reduced pressure, preferably a reduced pressure of l to mm. Hg.
- the surface active agent of the present invention has several predominant characteristics; first, it exhibits heatresisting stability. Particularly, in the case where a nonionic surface active agent, which is used as raw material, has saturated alkyl group and does not contain amino or amide group and contains 1 to mols of either ethylene oxide or both ethylene oxide and propylene oxide, and Where the higher alcohol, which is used as the raw material, has a saturated alkyl group, the resultant surface active agent exhibits less weight-reduction due to volatilization and also less change in hue even if it is left in the atmosphere at a high temperature exceeding 200 C. for a long time. Such a high heat resistance couldnot be expected in conventional surface active agents. Secondly, all of the surface active agent of the present invention has remarkably reduced foaming property in comparison with conventional surface active agents.
- the surface active agent of the present invention is widely used as an emulsifier, solubilizer, detergent, dispersant, lubricant, antistatic agent, defoaming agent, etc. in the similar manner to that of conventional sunface active agents.
- the surface active agents of the presuses as, for example, an antistatic agent and lubricant for synthetic fibers which are treated at a high temperature, additive for metal-lubricating oil which has antioxidative property, internal antistatic agent for synthetic molded article or synthetic fiber, and purifying and dispersing agent for engine oil, etc.
- EXAMPLE 1 490 g. of poly[8]oxyethylene lauryl ether, which were prepared by adding an average of 8 moles of ethylene oxide to 1 mole of commercial lauryl alcohol, 103 g. of triphenyl phosphite and 0.5 g. of potassium hydroxide were charged into a four neck flask equipped with an agitator, thermometer and vacuum apparatus. The resultant mixture was heated to 130 C. and stirred for one hour and then, treated under a reduced pressure of 10 mm. Hg at a temperature of 130 to 180 C. for three hours to effect dephenolization. 93 g. of phenol was distilled off.
- brackets indicate an average number of moles of ethylene oxide added to the conventional surface active agent.
- EXAMPLE 3 162 g. poly[9]oxyethylene lauryl ether, 138 g. of tri- (o-chlorophenyl) phosphite and 0.2 g. of sodium hydroxide were charged into a four neck flask equipped with an agitator, thermometer and vacuum apparatus. The mixture was heated to C. and then treated at a temperature from 130 to 180 C. .under a reduced pressure of 5 mm. Hg for two hours to effect dephenolization and to distill off 42 g. of o-chlorophenol. Further, 126' g. of commercial lauryl alcohol were added to the above product. Then, the mixture was treated at a temperature from 180 to 250 C. under a reduced pressure of 5 mm.
- Example 8 a mixture of parts by weight of the product in Example 8 and 50 parts by weight of spindle oil having a viscosity of 150 sec. was heated to 80 C. and then, 35 parts by weight of warm water at 80 C. were gradually poured into the heated mixture while being stirred, a uniform and stable emulsion of w/o type was obtained.
- Example 14 In the case where 2 g. of the product in Example 14 was dissolved in 30 g. of water and then, 70 g. of commercial gasoline was dripped for min. while being violently stirred, a highly viscous emulsion having a viscosity of 20,000 cps. at 20 C. was obtained. The resultant emulsion was found to be useful for printing.
- detergency As to the products in Examples 1, 4, 5, 10 and 17, detergency was tested by a detergency testing procedure determined by the Japan Oil Chemists Society using a Launder- O-Meter under the following conditions; temperature, 40i1 C.; time, 30 min.; 20 steel balls each having a diameter of M4 inch were used; number of revolutions, 40 r.p.m.; concentration of surfactant, 0.3% by weight.
- Spectral reflectance was determined by a spectrophotometer made by Hitachi Seisakusho, Japan, wherein a meas ured value of magnesium carbonate specimen was 100 in relation to the standard value. Detergency efficiency was calculated from the following equation:
- each of R R and 3 is represented by the formula C EH11 wherein n is an integer of 1 to 20.
- each of R R and R is represented by the wherein each of R R and R is represented by the forformula mula CnHro 5 @mmmon-cm.
- n is an integer of 1 to 20.
- n is an integer of 1 to 20.
- each of R R and R is represented by the for- 10 References Cited UNITED STATES PATENTS mula 2,361,022 10/ 1944 Gilbert 260-403 c H 2,987,385 6/1961 De Gray 44-66 3,004,057 10/ 1961 Nunn, Jr 260-461 O (CIHO)H CZH V V 15 3,682,988 8 /1972 Lewls 260-403 C H ELBERT L. ROBERTS, Primary Examiner US. Cl. X.R.
- n is an integer of 1 to 20.
- a surface active compound according to claim 1 25232.5, 351; 260-950, 951, 944
Abstract
A NOVEL SURFACE ACTIVE AGENT COMPRISING A PHOSPHOROUS TRIESTER-TYPE COMPOUND HAVING THE FOLLOWING FORMULA:
R1-O-P(-O-R2)-O-R3
WHEREIN R1 IS A CONVENTIONAL NONIONIC SURFACE ACTIVE AGENT RESIDUE TO WHICH ETHYLENE OXIDE OR BOTH ETHYLENE OXIDE AND PROPYLENE OXIDE IS ADDED AND R2 AND R3 ARE TO CONVENTIONAL NONIOONIC SURFACE ACTIVE AGENY RESIDUE TO WHICH ETHYLENE OXIDE OR BOTH ETHYLENE OXIDE AND PROPYLENE OXIDE IS ADDED OR AN ALKYL GROUP HAVING 8 TO 22 CARBON ATOMS AND ITS PREPAATION ARE DESCRIBED. THE SURFACE ACTIVE AGENT IS SUPERIOR IN SURFACE ACTIVITY HEAT RESISTING STABILITY AND A REDUCED FOAMING PROPERTY.
R1-O-P(-O-R2)-O-R3
WHEREIN R1 IS A CONVENTIONAL NONIONIC SURFACE ACTIVE AGENT RESIDUE TO WHICH ETHYLENE OXIDE OR BOTH ETHYLENE OXIDE AND PROPYLENE OXIDE IS ADDED AND R2 AND R3 ARE TO CONVENTIONAL NONIOONIC SURFACE ACTIVE AGENY RESIDUE TO WHICH ETHYLENE OXIDE OR BOTH ETHYLENE OXIDE AND PROPYLENE OXIDE IS ADDED OR AN ALKYL GROUP HAVING 8 TO 22 CARBON ATOMS AND ITS PREPAATION ARE DESCRIBED. THE SURFACE ACTIVE AGENT IS SUPERIOR IN SURFACE ACTIVITY HEAT RESISTING STABILITY AND A REDUCED FOAMING PROPERTY.
Description
United States Patent US. Cl. 260-403 Claims ABSTRACT OF THE DISCLOSURE A novel surface active agent comprisin a phosphorous triester-type compound having the following formula:
wherein R is a conventional nonionic surface active agent residue to which ethylene oxide or both ethylene oxide and propylene oxide is added, and R and R are a con ventional nonionic surface active agent residue to which ethylene oxide or both ethylene oxide and propylene oxide is added or an alkyl group having 8 to 22 carbon atoms and its preparation are described. The surface active agent is superior in surface activity, heat-resisting stability and a reduced foaming property.
This invention relates to a novel surface active agent and a method of preparing the same.
An object of the present invention is to provide a novel surface active agent which has superior surface activities, a heat-resisting stability and a reduced foaming property.
Other objects and advantages of the present invention will become apparent from the following description.
The surface active agent of the present invention comprises a compound having the following general formula:
wherein R is a conventional nonionic surface active agent residue to which one or more moles of ethylene oxide or one or more moles of both ethylene oxide and propylene oxide is added, and R and R are a member selected from the group consisting of a conventional nonionic surface active agent residue to which one or more moles of ethylene oxide or one or more moles of both ethylene oxide and propylene oxide is added and an alkyl group having 8 to 22 carbon atoms.
The above conventional nonionic surface active agent includes, for example, (1) a nonionic surface active agent of such a type as an addition product of l to 100 moles of ethylene oxide or 1 to 100 moles of both ethylene oxide and propylene oxide to one mole of higher alcohol having 8 to 22 carbon atoms such as octyl alcohol, lauryl alcohol, coconut alcohol, cetyl alcohol, stearyl alcohol, oleyl alcop CC hol, tridecyl alchol, etc.; (2) that of such a type as an addition product of 1 to moles of ethylene oxide or 1 to 100 moles of both ethylene oxide and propylene oxide to one mole of alkyl phenol containing an alkyl group having 4 to 22 carbon atoms such as butyl phenol, octyl phenol, nonyl phenol, dodecyl phenol, dinonyl phenol, etc.; (3) that of such a type as an addition product of 1 to 100 moles of ethylene oxide or 1 to 100 moles of both ethylene oxide and propylene oxide to one mole of higher fatty acid having 8 to 22 carbon atoms such as coconut fatty acid, lauric acid, oleic acid, stearic acid, palmitic acid, etc.; (4) that of such a type as an addition product of 1 to 100 moles of ethylene oxide or 1 to 100 moles of both ethylene oxide and propylene oxide to one mole of alkyl amine having 8 to 22 carbon atoms such as coconut amine, lauryl amine, stearyl amine, hexadecyl amine, etc.; (5) that of such a type as an addition product of 1 to 100 moles of ethylene oxide or 1 to 100 moles of both ethylene oxide and propylene oxide to one mole of higher fatty acid amide having 8 to 22 carbon atoms such as lauric acid amide, stearic acid amide, palmitic acid amide, oleic acid amide, etc., and (6) that of such a type as an addition product of 1 to 100 moles of ethylene oxide or 1 to 100 moles of both ethylene oxide and propylene oxide to one mole of aryl phenol having 2 to 5 benzene rings such as p-phenyl phenol, benzyl naphthol and tri-ethylbenzene phenol, etc.
The surface active agent of the present invention is prepared by the following method:
The compound wherein all of R R and R in the above formula are conventional surface active agent residues, is prepared by reacting one mole of triaryl phosphite or trichloroaryl phosphite with at least about 3 moles of a conventional surface active agent using a strong basic catalyst, which results in ester interchange of the former with the latter.
The compound wherein one or two of R and R in the formula are alkyl groups having 8 to 22 carbon atoms, is prepared by reacting one mole of triaryl phosphite or trichloroaryl phosphite with at least about three moles of both conventional surface active agent and higher alcohol, wherein the mole ratio of the surface active agent to the higher alcohol is approximately /2 to 2, using a strong basic catalyst.
A strong basic catalyst, which is used in the present invention, includes, for example, metal alcoholates such as sodium methylate, potassium phenolate, etc.; quaternary ammonium hydroxides; inorgamc strong bases such as sodium hydroxide, potassium hydroxide, etc; and alkali metals such as sodium, potassium, etc. As to the proportion of the basic catalyst, from 0.001 to 0.20 mole based on the moles of triaryl phosphite or trichloroaryl phosphite is preferable.
Triaryl phosphite or trichloroaryl phosphite, which is used in the present invention, includes, for example, triphenyl phosphite, tri-p-cresyl phosphite, tri-o-cresyl phosphite, tri-m-cresyl phosphite, tri-butylphenyl phosphite, tri-o-chlorophenyl phosphite, tri-p-chlorophenyl phosphite, tri-m-chlorophenyl phosphite, etc.
Conventional surface active agents, which are used in the present invention, are listed hereinbefore.
The higher alcohol, which is used in the present invention, is a saturated or unsaturated alcohol containing an 3 alkyl group having 8 to 22 carbon atoms which includes, for example, octanol, decanol, lauryl alcohol, myristyl alcohol, palmityl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, coconut alcohol, tridecyl alcohol, etc.
The ester interchange reaction of the present invention is effected at a temperature of 100 to 250 C. under atmospheric or reduced pressure, preferably a reduced pressure of l to mm. Hg.
The surface active agent of the present invention has several predominant characteristics; first, it exhibits heatresisting stability. Particularly, in the case where a nonionic surface active agent, which is used as raw material, has saturated alkyl group and does not contain amino or amide group and contains 1 to mols of either ethylene oxide or both ethylene oxide and propylene oxide, and Where the higher alcohol, which is used as the raw material, has a saturated alkyl group, the resultant surface active agent exhibits less weight-reduction due to volatilization and also less change in hue even if it is left in the atmosphere at a high temperature exceeding 200 C. for a long time. Such a high heat resistance couldnot be expected in conventional surface active agents. Secondly, all of the surface active agent of the present invention has remarkably reduced foaming property in comparison with conventional surface active agents.
The surface active agent of the present invention is widely used as an emulsifier, solubilizer, detergent, dispersant, lubricant, antistatic agent, defoaming agent, etc. in the similar manner to that of conventional sunface active agents. Among the surface active agents of the presuses as, for example, an antistatic agent and lubricant for synthetic fibers which are treated at a high temperature, additive for metal-lubricating oil which has antioxidative property, internal antistatic agent for synthetic molded article or synthetic fiber, and purifying and dispersing agent for engine oil, etc.
In order that the invention may be more fully under- Y stood, examples are given below.
EXAMPLE 1 490 g. of poly[8]oxyethylene lauryl ether, which were prepared by adding an average of 8 moles of ethylene oxide to 1 mole of commercial lauryl alcohol, 103 g. of triphenyl phosphite and 0.5 g. of potassium hydroxide were charged into a four neck flask equipped with an agitator, thermometer and vacuum apparatus. The resultant mixture was heated to 130 C. and stirred for one hour and then, treated under a reduced pressure of 10 mm. Hg at a temperature of 130 to 180 C. for three hours to effect dephenolization. 93 g. of phenol was distilled off. After filtration, colorless and transparent oily product having a speeific gravity of 1.014 (ZS/4 C.) was obtained. The resultant product proved that it did not have an infrared absorption spectrum corresponding to an OH product was tested as will be described later.
A numerical value within the brackets indicates an average number of moles of ethylene oxide added to the conventional surface active agent.
EXAMPLE 2 group. The
980 g. of poly[l5]oxyethylene-poly[2]oxypropylene g 4 hol, 103 g. of triphenyl phosphite and 0.5 g. of potassium hydroxide were treated in the same manner as'described in- Example 1 to effect dephenolization. 93 g. of phenol was distilled off. After filtration, a white waxy product was obtained. The product proved that it did not have an infrared absorption spectrum corresponding to an OH group. The product was tested as will be described later.
EXAMPLE 3 162 g. poly[9]oxyethylene lauryl ether, 138 g. of tri- (o-chlorophenyl) phosphite and 0.2 g. of sodium hydroxide were charged into a four neck flask equipped with an agitator, thermometer and vacuum apparatus. The mixture was heated to C. and then treated at a temperature from 130 to 180 C. .under a reduced pressure of 5 mm. Hg for two hours to effect dephenolization and to distill off 42 g. of o-chlorophenol. Further, 126' g. of commercial lauryl alcohol were added to the above product. Then, the mixture was treated at a temperature from 180 to 250 C. under a reduced pressure of 5 mm. Hg for 4 hours to effect dephenolization. 84 g. of o-chlorophenol were distilled off. After filtration, colorless and transparent oily product having a specific gravity of 0.952 (25/ 4 C.) was obtained. The resultant product proved that it did not exhibit an infrared absorption spectrum corresponding to an OH group. The product was also tested as will be described Methods similar to those described in Examples 1 to 3 were repeated except that starting materials and reacting conditions were as listed in Table l and Table 2, respectively.
OH group. They were tested as will. be described later.
TABLE 1 Ex. Nonionic surfactant Ph No. Higher alcohol G. este r i G. 4. Poly[8]oxyethy1ene 00!; l 560 Tri hl h phenol ether. y phii ph ii i enyl 138 5- Polylaloxypropylenepoly[10] 834 .....do 138 orgethylene nonyl phenol e er. I
6. Poly[10]oxyethylene oleyl 708 Trl-p-cresyl phos- 119 ether. phlte. 7. Polt3lr1[15]oxyethylenecetyl Y 902 .....do 119 Y a e er. 8. .-..Polyl2loxyethy1ene non l 308 Ti-o-cre 1 l1" I v phenol ether. y q phite. 9. Poly[18]oxyethylene trl-ethyl 1,199 .....do .119
benzene phenol ether. v 10--.- Poly[10]oxyethylene lauric I 654 'I'rl-butylphenyl am ester. 1 a phosphite. v, 11- Polyl3loxypropylene-polylQ] 710 ..-Ld0......'.'.-..-.-.'.
otxlyethylene butylphenol e er. 12- Poly[l0]oxyethylene hexa- 681 'Iri-phenyl phos- 103 decylamjne. phite. 13-... Poly[10]oxyethylene stearie 1722 -..-.do 103 acid amide. 14- Po1y[60]oxyethylene nonyl- 2,860 103 1 plhenol ether. 15 gggi 0157] 'lrl-o-chlorophenyl 138 Lam-y] alcohol; p "I i i 16 Poalggllilgoxyethylenelauryl 208 w t lphenyl 135 f li% 1------,;----=...-.- 87 PMSPM- o y oxyet lene oct 1- 395 I phenol ether. y 135 Decanol I 53 18 Poly[10]oxyethylene-poly[5 338 oxypropylene stearyl ether.
gtearlgll alcoh olim 187 oy oxye yeneol 4 261 i 19- i opylenelaurib e e id Tn'phenyl phosl 103 T amide. phite. p auryl alcohol 262 "'{P0lt[6]oxyethylene lauryl 296 103 e er. Lauryl alcohol 60 Poly[6]oxyethylene oleyl ether. 354 m3 glelsylzzallcoholifiul 90 0y oxye ene di-non l- 818 phenol ether. y 103 Myrlstyl alcohol 57 All of the resultant products proved that they did not"- have an infrared absorption spectrum corresponding to an TABLE 2 Amount of phenolic Reaction oompd. distilled Temp. Time ofi(g.) 0.) (hr.) Catalyst G. Appearance oiproduct Example No.
0. 2 Pale yellow and transparent oily. 0. 4 Colorless and transparent oily. 0. 3 Pale yellow and transparent oily. 8 NaOlight of the prodof 30 parts by 0.3 Pale yellow waxy.
(2) Emulsification At 220 C. for hr.
Decrement by volatilization (percent by weight) Each of the mixtures of parts by we net in Example 1 and parts by weight of refined mineral oil having a viscosity of sec., weight of the product in Example 15 and 70 parts by given in weight of refined mineral oil having a viscosity of 100 30 sec., and of 30 parts by weight of the product in Example 20 and 70 parts by weight of refined mineral oil having Heat-resisting stability At 220 C, for 1 hr.
Decrement by volatili- (p Hue weight) change stability Properties of the products obtained in the above Ex- TABLE 3 Testing items Foaming prop- (dyne/cm.) erty (mm.)
Immedi- 3 min; ately after after Hue 1% 0.5% dripping dripping change Properties of the surface active agent of the present tion is hereinafter described.
(1) Surface tension, foaming property and heat-resisting Surface tension v i i 0 n t I w m w v 0 v m m v n t n p t n 0 m 0 m m o t t t n M n m M n m p. m t .p. m 8 S a 0 m 8 D m n. n as P w a m aye". m B u m n mam u 0 m a n a my Y i m. mum hwhw n ls s SHUWS... 1. .SV 90 OOOM OBX m tmDDD e D t a m d mm m M C PWC YPYP 0% 55338559551559% 0 0 0 0 00 0 0 &0 00 0 & n rm u n n u u u n n Tm u u n n n n r .r u u .v. .m u n n n u "m n e :mm m u n m "awa t: "we .tt e m .tH .68 H mArHHmHHm Hmm Oaa MOOaOO aOaa KNN TKKNKKKNKNN 54333344332708 3 1 0000000000 000 mmwwmmwwwmmwmmm 11111 111111 11 778888443337444 220000229992222 11111111 1111 n u 4 amples 1 to 22 were determined. Results are Table 3 in comparison with conventional surface active agents.
inven Surfactants 3894678385255599621949 alzLnmomLLlfiz mkfiiamzamiLamnm nnnnncnnnnnocsccnnnnfln 3082377355 18161744487 LLL10 0 0 0 0 2 L0 &2 2 LL2LLQ 1.-.-..-..---.---.- S 165 c r 1 Control surface active agents are as follows: 1 poly[8]oxyethylene lauryl ether, 2 poly [8]oxyethy1ene octyl phenol ether, 3=poly[l0]oxyethylene oleyl phenol ether, 4=poly[20]oxyethylene sorbitan tristearate, 5=poly[10]oxyethylene stearic acid amide. 9 Surface tension was determined by a Du N oily-type tension meter at 25 C. a Foaming properties were tested by Ross Meiles method at 40 C. using 0.25% by weight solution of surfactant. Height of foams were determined immediately after and 3 min. after dripping.
4 Heat-resisting stability was tested by the following method; 30 g. of each sample surfactant were charged into a test tube (36 mm. x 200 mm.). Aiter the sam e was left in a thermostat at 220 C. r 6 hours without corking the test tube, decrement of the sample by volatlllzation and hue change of the sample were measured. Marks "n," gfilfiz" and r" designate no change," "slightly changed," changed" and remarkably changed," respec ve y.
a viscosity of 100 Saybolt sec. could be uniformly dispersed in water at room temperature.
In the case where a mixture of 30 parts by weight of the product in Example 6 and 70 parts by weight of butyl stearate was heated to 50 C. and then, 150 parts by weight of warm water at 60 C. were poured into the heated mixture while being gradually stirred, a uniform emulsion was obtained.
Further, in the case where a mixture of parts by weight of the product in Example 8 and 50 parts by weight of spindle oil having a viscosity of 150 sec. was heated to 80 C. and then, 35 parts by weight of warm water at 80 C. were gradually poured into the heated mixture while being stirred, a uniform and stable emulsion of w/o type was obtained.
Still further, in the case where 2 g. of the product in Example 14 was dissolved in 30 g. of water and then, 70 g. of commercial gasoline was dripped for min. while being violently stirred, a highly viscous emulsion having a viscosity of 20,000 cps. at 20 C. was obtained. The resultant emulsion was found to be useful for printing.
(3) Detergency As to the products in Examples 1, 4, 5, 10 and 17, detergency was tested by a detergency testing procedure determined by the Japan Oil Chemists Society using a Launder- O-Meter under the following conditions; temperature, 40i1 C.; time, 30 min.; 20 steel balls each having a diameter of M4 inch were used; number of revolutions, 40 r.p.m.; concentration of surfactant, 0.3% by weight. Spectral reflectance was determined by a spectrophotometer made by Hitachi Seisakusho, Japan, wherein a meas ured value of magnesium carbonate specimen was 100 in relation to the standard value. Detergency efficiency was calculated from the following equation:
Detergency efficiency (percent) 55 X 100 where;
D=Detergency efliciency of deterged fabric,
S=Detergency efficiency of stained fabric,
O=Detergency efficiency of original fabric. Results are given in Table 4.
TABLE 4 Detergency Surfactant efliciency Product in Example:
(4) Antistatic property to pick-up OWF, the taffeta was air-dried. -Anti'static property of the resultant taffeta was measured-by a Tex- I I and TABLE 5 Surface electric resistance (ohm) Nylon Surfactant Product in Example:
Tetoron Further as to the products in Examples 1-3, 13, 18, 19 and 20, antistatic property was tested by the following method:
0.2 g. of each product was added to g. of polyethylene ("Sumikasen L-702 made by Sumitomo Chemical, Japan) and the mixture was roll-milled at C. for 10 min. and then, subjected to press molding at C. for 10 min. to form a sheet having a thickness of 2 mm.
When the resultant sheet was superposed above the ash of cigarette at a distance of 1 cm. after it was rubbed with nylon cloth ten times, the ash was not attracted to the sheet, resulting in proof that the sheet contained a favorable antistatic property. On the other hand, in the case of the sheet which did not contain the product, the ash was attracted to it.
Color of both sheets did not change through the above press moulding.
What we claim is:
1. A surface active compound having the formula R1O\ RzO-P wherein R R and R are each the same residue of a nonionic surface active compound, said residue having a formula selected from a member of the group consisting of wherein in each of said formulas, n is an integer of 1 to 20.
2. A surface active compound according to claim 1 wherein each of R R and 3 is represented by the formula C EH11 wherein n is an integer of 1 to 20.
3. A surface active compound according to claim 1 wherein each of R R and R is represented by the wherein each of R R and R is represented by the forformula mula CnHro 5 @mmmon-cm.
-O(C3H40) r-CzHrwherein n is an integer of 1 to 20.
wherein n is an integer of 1 to 20.
4. A surface active compound according to claim 1 wherein each of R R and R is represented by the for- 10 References Cited UNITED STATES PATENTS mula 2,361,022 10/ 1944 Gilbert 260-403 c H 2,987,385 6/1961 De Gray 44-66 3,004,057 10/ 1961 Nunn, Jr 260-461 O (CIHO)H CZH V V 15 3,682,988 8 /1972 Lewls 260-403 C H ELBERT L. ROBERTS, Primary Examiner US. Cl. X.R.
wherein n is an integer of 1 to 20.
5. A surface active compound according to claim 1 25232.5, 351; 260-950, 951, 944
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP8156969 | 1969-10-14 | ||
JP8736369 | 1969-11-01 |
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US3799956A true US3799956A (en) | 1974-03-26 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2455607A1 (en) * | 1979-05-04 | 1980-11-28 | Lubrizol Corp | PHOSPHORUS COMPOSITIONS AND LUBRICANTS CONTAINING THESE COMPOSITIONS |
US4568480A (en) * | 1983-11-17 | 1986-02-04 | Basf Wyandotte Corporation | Microemulsions |
US5202056A (en) * | 1991-12-30 | 1993-04-13 | Texaco Inc. | Composition of matter for oligomeric aliphatic ethers as asphaltene dispersants |
US5922897A (en) * | 1998-05-29 | 1999-07-13 | Xerox Corporation | Surfactant processes |
US5944650A (en) * | 1997-10-29 | 1999-08-31 | Xerox Corporation | Surfactants |
-
1970
- 1970-10-12 US US00080030A patent/US3799956A/en not_active Expired - Lifetime
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2455607A1 (en) * | 1979-05-04 | 1980-11-28 | Lubrizol Corp | PHOSPHORUS COMPOSITIONS AND LUBRICANTS CONTAINING THESE COMPOSITIONS |
US4568480A (en) * | 1983-11-17 | 1986-02-04 | Basf Wyandotte Corporation | Microemulsions |
US5202056A (en) * | 1991-12-30 | 1993-04-13 | Texaco Inc. | Composition of matter for oligomeric aliphatic ethers as asphaltene dispersants |
US5944650A (en) * | 1997-10-29 | 1999-08-31 | Xerox Corporation | Surfactants |
US5922897A (en) * | 1998-05-29 | 1999-07-13 | Xerox Corporation | Surfactant processes |
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