CA2019584A1 - Aminocarboxy surfactants cycliques, leur synthese et leur utilisation - Google Patents

Aminocarboxy surfactants cycliques, leur synthese et leur utilisation

Info

Publication number: CA2019584A1
Authority: CA; Canada
Prior art keywords: consisting essentially; group; mixtures; alkaryl; alkylene
Prior art date: 1989-08-08
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.): Abandoned

Application number

CA002019584A

Other languages

English (en)

Inventor

Jean M. Goze

Randal J. Bernhardt

James A. Hartlage

Norman R. Smith

Dennis E. Lietz

James W. Kay

Fred W. Breitbeil, Iii

Branko Sajic

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Stepan Co

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1989-08-08

Filing date

1990-06-21

Publication date

1991-02-08

1990-06-21 Application filed by Individual filed Critical Individual

1991-02-08 Publication of CA2019584A1 publication Critical patent/CA2019584A1/fr

Status Abandoned legal-status Critical Current

Links

239000004094 surface-active agent Substances 0.000 title claims abstract description 171
230000015572 biosynthetic process Effects 0.000 title claims abstract description 51
238000003786 synthesis reaction Methods 0.000 title abstract description 24
125000004122 cyclic group Chemical group 0.000 title abstract description 4
239000000203 mixture Substances 0.000 claims abstract description 290
125000000217 alkyl group Chemical group 0.000 claims abstract description 124
125000002947 alkylene group Chemical group 0.000 claims abstract description 106
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 105
125000003118 aryl group Chemical group 0.000 claims abstract description 104
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 102
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 88
229910052708 sodium Inorganic materials 0.000 claims abstract description 77
239000000839 emulsion Substances 0.000 claims abstract description 75
239000003995 emulsifying agent Substances 0.000 claims abstract description 74
150000001768 cations Chemical class 0.000 claims abstract description 57
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 51
239000004816 latex Substances 0.000 claims abstract description 51
229920000126 latex Polymers 0.000 claims abstract description 50
229910052700 potassium Inorganic materials 0.000 claims abstract description 48
239000000463 material Substances 0.000 claims abstract description 39
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 36
-1 i.e. Substances 0.000 claims abstract description 31
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 28
238000000576 coating method Methods 0.000 claims abstract description 27
239000003921 oil Substances 0.000 claims abstract description 23
239000003208 petroleum Substances 0.000 claims abstract description 20
239000011248 coating agent Substances 0.000 claims abstract description 19
239000006260 foam Substances 0.000 claims abstract description 19
229910052782 aluminium Inorganic materials 0.000 claims abstract description 17
239000004744 fabric Substances 0.000 claims abstract description 15
229910052749 magnesium Inorganic materials 0.000 claims abstract description 15
238000006116 polymerization reaction Methods 0.000 claims abstract description 15
239000000853 adhesive Substances 0.000 claims abstract description 14
230000001070 adhesive effect Effects 0.000 claims abstract description 14
229910052788 barium Inorganic materials 0.000 claims abstract description 14
229910052791 calcium Inorganic materials 0.000 claims abstract description 14
239000004753 textile Substances 0.000 claims abstract description 14
239000003599 detergent Substances 0.000 claims abstract description 13
229920002635 polyurethane Polymers 0.000 claims abstract description 11
239000004814 polyurethane Substances 0.000 claims abstract description 11
229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 8
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 8
239000011707 mineral Substances 0.000 claims abstract description 8
229910052751 metal Inorganic materials 0.000 claims abstract description 6
239000002184 metal Substances 0.000 claims abstract description 6
239000002023 wood Substances 0.000 claims abstract description 6
239000000314 lubricant Substances 0.000 claims abstract description 4
239000011734 sodium Substances 0.000 claims description 77
238000000034 method Methods 0.000 claims description 53
150000001412 amines Chemical class 0.000 claims description 52
238000006243 chemical reaction Methods 0.000 claims description 48
238000009472 formulation Methods 0.000 claims description 48
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 claims description 38
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 32
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 32
229910003202 NH4 Inorganic materials 0.000 claims description 25
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 24
235000019198 oils Nutrition 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 21
150000003949 imides Chemical class 0.000 claims description 20
239000000944 linseed oil Substances 0.000 claims description 18
238000003756 stirring Methods 0.000 claims description 18
150000008064 anhydrides Chemical class 0.000 claims description 17
239000004615 ingredient Substances 0.000 claims description 17
235000021388 linseed oil Nutrition 0.000 claims description 17
239000002453 shampoo Substances 0.000 claims description 16
VBSAJQAPLZZJAI-UHFFFAOYSA-M sodium;2-(dodecylcarbamoyl)benzoate Chemical compound [Na+].CCCCCCCCCCCCNC(=O)C1=CC=CC=C1C([O-])=O VBSAJQAPLZZJAI-UHFFFAOYSA-M 0.000 claims description 16
OREMCCHQIOQXHP-UHFFFAOYSA-M sodium;2-(octadecylcarbamoyl)benzoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCNC(=O)C1=CC=CC=C1C([O-])=O OREMCCHQIOQXHP-UHFFFAOYSA-M 0.000 claims description 16
239000003974 emollient agent Substances 0.000 claims description 15
238000010438 heat treatment Methods 0.000 claims description 15
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 14
238000007792 addition Methods 0.000 claims description 14
239000011591 potassium Substances 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
229910052726 zirconium Inorganic materials 0.000 claims description 13
230000008859 change Effects 0.000 claims description 12
238000001035 drying Methods 0.000 claims description 12
150000001447 alkali salts Chemical class 0.000 claims description 11
230000000269 nucleophilic effect Effects 0.000 claims description 11
229910052719 titanium Inorganic materials 0.000 claims description 11
230000003750 conditioning effect Effects 0.000 claims description 10
239000002537 cosmetic Substances 0.000 claims description 10
239000002979 fabric softener Substances 0.000 claims description 10
230000006872 improvement Effects 0.000 claims description 9
239000003999 initiator Substances 0.000 claims description 9
239000000178 monomer Substances 0.000 claims description 9
239000003905 agrochemical Substances 0.000 claims description 8
ARZCPZFTGFYWMG-UHFFFAOYSA-M sodium;2-[dodecyl(methyl)carbamoyl]benzoate Chemical compound [Na+].CCCCCCCCCCCCN(C)C(=O)C1=CC=CC=C1C([O-])=O ARZCPZFTGFYWMG-UHFFFAOYSA-M 0.000 claims description 8
GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical compound COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 claims description 7
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
230000001804 emulsifying effect Effects 0.000 claims description 7
239000003265 pulping liquor Substances 0.000 claims description 7
YXVPBQBINZBTLQ-UHFFFAOYSA-M sodium;2-(hexadecylcarbamoyl)benzoate Chemical compound [Na+].CCCCCCCCCCCCCCCCNC(=O)C1=CC=CC=C1C([O-])=O YXVPBQBINZBTLQ-UHFFFAOYSA-M 0.000 claims description 7
IEGFZYAVYGWQDO-UHFFFAOYSA-M sodium;2-[3-(10-methylundecoxy)propylcarbamoyl]benzoate Chemical compound [Na+].CC(C)CCCCCCCCCOCCCNC(=O)C1=CC=CC=C1C([O-])=O IEGFZYAVYGWQDO-UHFFFAOYSA-M 0.000 claims description 7
238000005406 washing Methods 0.000 claims description 7
239000004166 Lanolin Substances 0.000 claims description 6
XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 claims description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
229920000180 alkyd Polymers 0.000 claims description 6
125000000129 anionic group Chemical group 0.000 claims description 6
239000002585 base Substances 0.000 claims description 6
238000007720 emulsion polymerization reaction Methods 0.000 claims description 6
235000019388 lanolin Nutrition 0.000 claims description 6
229940039717 lanolin Drugs 0.000 claims description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 5
150000001342 alkaline earth metals Chemical class 0.000 claims description 5
239000002270 dispersing agent Substances 0.000 claims description 5
235000013305 food Nutrition 0.000 claims description 5
230000002363 herbicidal effect Effects 0.000 claims description 5
239000004009 herbicide Substances 0.000 claims description 5
239000012978 lignocellulosic material Substances 0.000 claims description 5
239000000575 pesticide Substances 0.000 claims description 5
238000009991 scouring Methods 0.000 claims description 5
NMQURXVYDJRACL-UHFFFAOYSA-M sodium;2-[hexadecyl(methyl)carbamoyl]benzoate Chemical compound [Na+].CCCCCCCCCCCCCCCCN(C)C(=O)C1=CC=CC=C1C([O-])=O NMQURXVYDJRACL-UHFFFAOYSA-M 0.000 claims description 5
ZJARAATVXUVMTN-UHFFFAOYSA-M sodium;2-[methyl(octadecyl)carbamoyl]benzoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCN(C)C(=O)C1=CC=CC=C1C([O-])=O ZJARAATVXUVMTN-UHFFFAOYSA-M 0.000 claims description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
235000019485 Safflower oil Nutrition 0.000 claims description 4
229940008099 dimethicone Drugs 0.000 claims description 4
239000004205 dimethyl polysiloxane Substances 0.000 claims description 4
235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 4
235000005713 safflower oil Nutrition 0.000 claims description 4
239000003813 safflower oil Substances 0.000 claims description 4
238000000926 separation method Methods 0.000 claims description 4
PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 4
LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 claims description 4
229920001567 vinyl ester resin Polymers 0.000 claims description 4
239000004264 Petrolatum Substances 0.000 claims description 3
150000004703 alkoxides Chemical class 0.000 claims description 3
150000003863 ammonium salts Chemical class 0.000 claims description 3
239000008172 hydrogenated vegetable oil Substances 0.000 claims description 3
150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 3
239000007764 o/w emulsion Substances 0.000 claims description 3
239000010690 paraffinic oil Substances 0.000 claims description 3
235000019271 petrolatum Nutrition 0.000 claims description 3
229940066842 petrolatum Drugs 0.000 claims description 3
239000003549 soybean oil Substances 0.000 claims description 3
235000012424 soybean oil Nutrition 0.000 claims description 3
239000003784 tall oil Substances 0.000 claims description 3
RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 claims description 2
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 claims description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 claims description 2
XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 claims description 2
239000003945 anionic surfactant Substances 0.000 claims description 2
239000012298 atmosphere Substances 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
229940110456 cocoa butter Drugs 0.000 claims description 2
235000019868 cocoa butter Nutrition 0.000 claims description 2
229940086555 cyclomethicone Drugs 0.000 claims description 2
ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 claims description 2
238000007599 discharging Methods 0.000 claims description 2
235000011187 glycerol Nutrition 0.000 claims description 2
XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 claims description 2
239000002480 mineral oil Substances 0.000 claims description 2
235000010446 mineral oil Nutrition 0.000 claims description 2
JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims description 2
229940101267 panthenol Drugs 0.000 claims description 2
239000011619 pantothenol Substances 0.000 claims description 2
235000020957 pantothenol Nutrition 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
235000013772 propylene glycol Nutrition 0.000 claims description 2
239000008159 sesame oil Substances 0.000 claims description 2
235000011803 sesame oil Nutrition 0.000 claims description 2
229940083542 sodium Drugs 0.000 claims description 2
239000000600 sorbitol Substances 0.000 claims description 2
235000010356 sorbitol Nutrition 0.000 claims description 2
238000005507 spraying Methods 0.000 claims description 2
229940032094 squalane Drugs 0.000 claims description 2
229940042585 tocopherol acetate Drugs 0.000 claims description 2
238000004804 winding Methods 0.000 claims description 2
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 12
125000005209 triethanolammonium group Chemical class 0.000 claims 5
230000002194 synthesizing effect Effects 0.000 claims 3
WTXXSZUATXIAJO-OWBHPGMISA-N (Z)-14-methylpentadec-2-enoic acid Chemical compound CC(CCCCCCCCCC\C=C/C(=O)O)C WTXXSZUATXIAJO-OWBHPGMISA-N 0.000 claims 1
WXQWKYFPCLREEY-UHFFFAOYSA-N azane;ethanol Chemical class N.CCO.CCO.CCO WXQWKYFPCLREEY-UHFFFAOYSA-N 0.000 claims 1
239000011538 cleaning material Substances 0.000 claims 1
239000000356 contaminant Substances 0.000 claims 1
235000003084 food emulsifier Nutrition 0.000 claims 1
239000000654 additive Substances 0.000 abstract description 30
239000000047 product Substances 0.000 abstract description 20
239000010779 crude oil Substances 0.000 abstract description 13
238000009736 wetting Methods 0.000 abstract description 8
239000000375 suspending agent Substances 0.000 abstract description 5
239000000080 wetting agent Substances 0.000 abstract description 5
239000003245 coal Substances 0.000 abstract description 4
239000004567 concrete Substances 0.000 abstract description 4
238000004519 manufacturing process Methods 0.000 abstract description 4
239000011236 particulate material Substances 0.000 abstract description 4
238000012545 processing Methods 0.000 abstract description 4
PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 abstract description 4
239000004566 building material Substances 0.000 abstract description 3
239000003795 chemical substances by application Substances 0.000 abstract description 3
238000009713 electroplating Methods 0.000 abstract description 3
239000010440 gypsum Substances 0.000 abstract description 3
229910052602 gypsum Inorganic materials 0.000 abstract description 3
239000011505 plaster Substances 0.000 abstract description 3
238000011084 recovery Methods 0.000 abstract description 3
208000001840 Dandruff Diseases 0.000 abstract description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
150000002191 fatty alcohols Chemical class 0.000 abstract description 2
239000011593 sulfur Substances 0.000 abstract description 2
229910052717 sulfur Inorganic materials 0.000 abstract description 2
239000004902 Softening Agent Substances 0.000 abstract 1
239000004568 cement Substances 0.000 abstract 1
238000013329 compounding Methods 0.000 abstract 1
238000005065 mining Methods 0.000 abstract 1
238000004537 pulping Methods 0.000 abstract 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
229910052757 nitrogen Inorganic materials 0.000 description 19
AZPJXONNBLOZFE-UHFFFAOYSA-N 2-[(3-methylphenyl)carbamoyl]benzoic acid Chemical class CC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(O)=O)=C1 AZPJXONNBLOZFE-UHFFFAOYSA-N 0.000 description 17
239000008367 deionised water Substances 0.000 description 16
229910021641 deionized water Inorganic materials 0.000 description 16
238000004566 IR spectroscopy Methods 0.000 description 15
229910052739 hydrogen Inorganic materials 0.000 description 15
238000012360 testing method Methods 0.000 description 15
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 14
238000004945 emulsification Methods 0.000 description 13
OTVDESMGXUUCQW-UHFFFAOYSA-N 2-(dodecylcarbamoyl)benzoic acid Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=CC=C1C(O)=O OTVDESMGXUUCQW-UHFFFAOYSA-N 0.000 description 11
150000001875 compounds Chemical class 0.000 description 11
239000007787 solid Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000000126 substance Substances 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
239000012467 final product Substances 0.000 description 10
238000003860 storage Methods 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
239000011777 magnesium Substances 0.000 description 9
239000011575 calcium Substances 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
150000003335 secondary amines Chemical class 0.000 description 8
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
238000013019 agitation Methods 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
150000003141 primary amines Chemical class 0.000 description 7
239000002904 solvent Substances 0.000 description 7
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
230000000996 additive effect Effects 0.000 description 6
238000005187 foaming Methods 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000008399 tap water Substances 0.000 description 6
235000020679 tap water Nutrition 0.000 description 6
NXXTWCCTMAXGSS-UHFFFAOYSA-N 2-(dodecylcarbamoyl)benzoate;triethylazanium Chemical compound CC[NH+](CC)CC.CCCCCCCCCCCCNC(=O)C1=CC=CC=C1C([O-])=O NXXTWCCTMAXGSS-UHFFFAOYSA-N 0.000 description 5
239000004604 Blowing Agent Substances 0.000 description 5
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 5
239000003125 aqueous solvent Substances 0.000 description 5
AOLVVXHUXDOKTN-UHFFFAOYSA-N azanium;2-(dodecylcarbamoyl)benzoate Chemical compound [NH4+].CCCCCCCCCCCCNC(=O)C1=CC=CC=C1C([O-])=O AOLVVXHUXDOKTN-UHFFFAOYSA-N 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
239000007844 bleaching agent Substances 0.000 description 5
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 5
239000000920 calcium hydroxide Substances 0.000 description 5
229910001861 calcium hydroxide Inorganic materials 0.000 description 5
235000011116 calcium hydroxide Nutrition 0.000 description 5
239000011280 coal tar Substances 0.000 description 5
230000006870 function Effects 0.000 description 5
239000006210 lotion Substances 0.000 description 5
238000005191 phase separation Methods 0.000 description 5
229920005862 polyol Polymers 0.000 description 5
150000003077 polyols Chemical class 0.000 description 5
230000008569 process Effects 0.000 description 5
159000000000 sodium salts Chemical group 0.000 description 5
239000000725 suspension Substances 0.000 description 5
150000003512 tertiary amines Chemical class 0.000 description 5
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DIVBQLCSYFMNCT-UHFFFAOYSA-N n-methyl-4-octadecylaniline Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=C(NC)C=C1 DIVBQLCSYFMNCT-UHFFFAOYSA-N 0.000 description 1
SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
QWERMLCFPMTLTG-UHFFFAOYSA-N n-methyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCNC QWERMLCFPMTLTG-UHFFFAOYSA-N 0.000 description 1
ZTQADAPGLVMBSC-UHFFFAOYSA-N n-nitrosonitramide Chemical class [O-][N+](=O)NN=O ZTQADAPGLVMBSC-UHFFFAOYSA-N 0.000 description 1
CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
HLERILKGMXJNBU-UHFFFAOYSA-N norvaline betaine Chemical compound CCCC(C([O-])=O)[N+](C)(C)C HLERILKGMXJNBU-UHFFFAOYSA-N 0.000 description 1
IQMGCJKDXCTZBG-UHFFFAOYSA-N octadecyl 2-carbamoylbenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(N)=O IQMGCJKDXCTZBG-UHFFFAOYSA-N 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000003973 paint Substances 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
230000037368 penetrate the skin Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000004999 plastisol Substances 0.000 description 1
229920005906 polyester polyol Polymers 0.000 description 1
229920000582 polyisocyanurate Polymers 0.000 description 1
239000011495 polyisocyanurate Substances 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
229920005903 polyol mixture Polymers 0.000 description 1
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
CHHGWMFMDLZDDM-UHFFFAOYSA-M potassium;2-(octadecylcarbamoyl)benzoate Chemical compound [K+].CCCCCCCCCCCCCCCCCCNC(=O)C1=CC=CC=C1C([O-])=O CHHGWMFMDLZDDM-UHFFFAOYSA-M 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000007639 printing Methods 0.000 description 1
CMDGQTVYVAKDNA-UHFFFAOYSA-N propane-1,2,3-triol;hydrate Chemical compound O.OCC(O)CO CMDGQTVYVAKDNA-UHFFFAOYSA-N 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 1
229960002026 pyrithione Drugs 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
235000012045 salad Nutrition 0.000 description 1
238000004904 shortening Methods 0.000 description 1
239000002884 skin cream Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229940057950 sodium laureth sulfate Drugs 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
229940048842 sodium xylenesulfonate Drugs 0.000 description 1
CCYGAAKCTJSTBG-UHFFFAOYSA-M sodium;2-(decylcarbamoyl)benzoate Chemical compound [Na+].CCCCCCCCCCNC(=O)C1=CC=CC=C1C([O-])=O CCYGAAKCTJSTBG-UHFFFAOYSA-M 0.000 description 1
DIDXNZLXVMGDJE-UHFFFAOYSA-M sodium;2-(tetradecylcarbamoyl)benzoate Chemical compound [Na+].CCCCCCCCCCCCCCNC(=O)C1=CC=CC=C1C([O-])=O DIDXNZLXVMGDJE-UHFFFAOYSA-M 0.000 description 1
SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
NYZZOURZZAHWFH-UHFFFAOYSA-M sodium;2-[3-(8-methylnonoxy)propylcarbamoyl]benzoate Chemical compound [Na+].CC(C)CCCCCCCOCCCNC(=O)C1=CC=CC=C1C([O-])=O NYZZOURZZAHWFH-UHFFFAOYSA-M 0.000 description 1
QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
239000011973 solid acid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000013112 stability test Methods 0.000 description 1
239000010902 straw Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000000475 sunscreen effect Effects 0.000 description 1
239000000516 sunscreening agent Substances 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
239000003760 tallow Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
238000011179 visual inspection Methods 0.000 description 1
239000012936 vulcanization activator Substances 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000004260 weight control Methods 0.000 description 1

Landscapes

Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

CA002019584A 1989-08-08 1990-06-21 Aminocarboxy surfactants cycliques, leur synthese et leur utilisation Abandoned CA2019584A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US39118789A	1989-08-08	1989-08-08
US391,187		1989-08-08

Publications (1)

Publication Number	Publication Date
CA2019584A1 true CA2019584A1 (fr)	1991-02-08

Family

ID=23545608

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002019584A Abandoned CA2019584A1 (fr)	1989-08-08	1990-06-21	Aminocarboxy surfactants cycliques, leur synthese et leur utilisation

Country Status (1)

Country	Link
CA (1)	CA2019584A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN120005672A (zh) *	2025-02-14	2025-05-16	东莞市英飞特润滑科技有限公司	一种黑色金属加工用磨削液及其制备方法

1990
- 1990-06-21 CA CA002019584A patent/CA2019584A1/fr not_active Abandoned

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN120005672A (zh) *	2025-02-14	2025-05-16	东莞市英飞特润滑科技有限公司	一种黑色金属加工用磨削液及其制备方法
CN120005672B (zh) *	2025-02-14	2025-10-24	东莞市英飞特润滑科技有限公司	一种黑色金属加工用磨削液及其制备方法

Legal Events

Date	Code	Title	Description
1997-06-18	EEER	Examination request
2001-06-21	FZDE	Discontinued

Publication	Publication Date	Title
WO1991001970A2 (fr)	1991-02-21	Tensio-actifs amidocarboxy cycliques, leur synthese et leur emploi
US5945393A (en)	1999-08-31	Nonionic gemini surfactants
US5656586A (en)	1997-08-12	Amphoteric surfactants having multiple hydrophobic and hydrophilic groups
DE69631026T2 (de)	2004-09-09	Verwendung von Kokosölfettsäureacylglutamin in Reinigungsmitteln
US5643864A (en)	1997-07-01	Anionic surfactants having multiple hydrophobic and hydrophilic groups
US9573884B2 (en)	2017-02-21	Imidazoline amides and derivitives from natural oil metathesis
CN103228615B (zh)	2016-06-22	源自天然油复分解的季铵化脂肪胺、酰胺基胺以及它们的衍生物
DE69305031T2 (de)	1997-02-13	In Wasser dispergierbares, UV-Strahlung absorbierendes Copolymer
DE69024183T2 (de)	1996-07-04	Quaternäre alkoxylierte Alkylglykosid-Ether und ihre Verwendung als Körperpflege
DE19743687C1 (de)	1998-11-26	Detergensgemische und deren Verwendung
EA023402B1 (ru)	2016-05-31	Амины жирного ряда, амидоамины жирных кислот и их производные из метатезиса натурального масла
DE19904513A1 (de)	2000-08-10	Detergensgemische
JPH07509740A (ja)	1995-10-26	発泡性洗剤混合物
JPS606996B2 (ja)	1985-02-21	洗剤組成物
MX2007004654A (es)	2008-01-16	Compuestos tensioactivos.
US5567808A (en)	1996-10-22	Alkyl polyglycosides having improved aesthetic and tactile properties
US5952290A (en)	1999-09-14	Anionic gemini surfactants and methods for their preparation
EP0038862A1 (fr)	1981-11-04	Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles
EP1339818B1 (fr)	2007-04-11	Combinaison nettoyante tensioactive constituee de matieres premieres renouvelables a fort pouvoir nettoyant
US5811384A (en)	1998-09-22	Nonionic gemini surfactants
Tyagi	2006	Sulfosuccinates as mild surfactants
MXPA04012727A (es)	2005-08-15	Dispersiones de un solido en un liquido acuoso que incluye un ester o amida de polialquilenglicol de un dimero y/o trimero de acido graso.
US20160002571A1 (en)	2016-01-07	Surfactants based on monounsaturated fatty alcohol derivatives
CA2019584A1 (fr)	1991-02-08	Aminocarboxy surfactants cycliques, leur synthese et leur utilisation
DE60215158T2 (de)	2007-08-16	Pumpfähige, flüssige, grenzflächenaktive mittel enthaltende zusammensetzungen, umfassend alkanolaminsalze von alkylphosphatestern