CN1172439A - 以酰胺为基础的带有至少二个亲水基和至少二个疏水基的两亲化合物 - Google Patents
以酰胺为基础的带有至少二个亲水基和至少二个疏水基的两亲化合物 Download PDFInfo
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- CN1172439A CN1172439A CN95197305A CN95197305A CN1172439A CN 1172439 A CN1172439 A CN 1172439A CN 95197305 A CN95197305 A CN 95197305A CN 95197305 A CN95197305 A CN 95197305A CN 1172439 A CN1172439 A CN 1172439A
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- 125000000524 functional group Chemical group 0.000 claims abstract description 3
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- 150000004703 alkoxides Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000012752 auxiliary agent Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
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- 125000005842 heteroatom Chemical group 0.000 claims description 2
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- 239000002184 metal Substances 0.000 claims description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
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- 150000002632 lipids Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
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- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
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- YRHYCMZPEVDGFQ-UHFFFAOYSA-N methyl decanoate Chemical compound CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 description 2
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- 238000004809 thin layer chromatography Methods 0.000 description 2
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- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
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- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
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- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
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- 125000002091 cationic group Chemical group 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
-
- 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
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
-
- 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
- C09K23/16—Amines or polyamines
-
- 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
- C09K23/22—Amides or hydrazides
-
- 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
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
-
- 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
-
- 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
- C11D1/02—Anionic compounds
- C11D1/34—Derivatives of acids of phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
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Abstract
本发明涉及以酰胺为基础的带有至少二个亲水基和至少二个疏水基的通式(Ⅰ)两亲化合物(R1,R3=C1－C22烃基,R2=间隔基团,X、Y=官能基,Z=1—10)。本发明的两亲化合物大多为界面活性物,适宜作工业和家用乳化剂、反乳化剂、洗涤剂、分散剂和水溶助长剂,例如在金属加工、采矿、表面处理、洗涤和清净,化妆品、医药领域以及食品加工和食品配制过程中应用。
Description
本发明涉及以酰胺为基础的带有至少二个亲水基和至少二个疏水基的两亲化合物。
作为两亲物质，已知有大量阴离子、阳离子、非离子和两性离子化合物。这类物质的绝大多数由一个亲水端基和至少一个疏水部分组成。
对于两亲物质，由于生态学的原因，例如关系到减少包装和运输费用，必须要使所使用物质单位质量达到尽可能大的效能。但通过两亲物质的混配实现优化是很有限的，所以要求能有一种高效的新型两亲物质。为此，特别必须找到具有较低的临界胶束形成浓度和/或较低的表面-和界面张力的特殊物质，这样才能大大减少有效物质的加入量。
已知初始解决方案就是使其结构的一部分(亲水的端基，疏水基)成倍增多。在全甲基化的亚烷基二胺上加成长链烷基卤化物，可得到阳离子界面活性化合物
[R.Zana，M.Benrraou，R.Rueff，Langmuir，7(1991)1072；R.Zana，Y.Talmon，Nature，362(1993)228；E.Alami，G.Beinert，P.Marie，R.Zana，Langmuir，9(1993)1465].
带有至少二个亲水基和至少二个疏水基的阴离子界面活性化合物迄今都是在二缩水甘油醚基础上制造的(US 5 1 60 450、JP 01 304033、JP 4 124 165)。但二缩水甘油醚从毒理学上讲被疑为有害，且价格相当贵，此外在制造该化合物时采用环氧氯丙烷，会生成大量的残余物，所以这类物质不论从生态毒理方面还是从经济角度考虑都不再符合时代要求。
因而提出的任务是找到一种两亲化合物，它至少具有二个亲水基和至少二个疏水基，该两亲化合物相对于其加入量而言，具有很好的效率，此外，它是由工业上易得的原料制造的，而且不生成大量的不希望产生的副产物。
这一任务按本发明可通过两亲的二-或低聚酰胺得到解决，它们的基础物质可由二-或低聚胺和脂肪酸及脂肪酸甲酯制成。相应的二-或低聚酰胺可进行烷氧化。该非离子两亲化合物可变为阴离子两亲化合物。采用的方法是将上述化合物与三氧化硫/惰性气体(或发烟硫酸或氯磺酸)，与聚磷酸，与一种卤代乙酸，与一种磺内酯，与一种牛磺酸进行反应，并各自再进行中和。
本发明的两亲化合物涉及通式I的化合物
其中式I中的R1，R2，R3，X，Y和Z具有下述的意义：
R1和R3互相独立地为非支链或带支链的饱和或不饱和的含1至22个碳原子的烃基，优选为含7至17个碳的烃基。
作为取代基的R1和R3各自可以是甲基、乙基、正丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、正十九烷基、正二十烷基、正二十一烷基、正二十二烷基及其带支链的异构体以及相应含一个、两个或三个不饱和键的烯类。
R2是一个间隔基团，由非支链或带支链的2至100个碳原子的链组成，并含有0至20个氧-，0至20个氮-，0至4个硫-和0至3个磷原子，它有0至20个功能性的侧链基，例如羟基、羰基、羧基、氨基和/或酰氨基。
该间隔基团R2特别是
◆作为基体无支链的或带支链的亚烷基链
-CaH2a- (II)
a＝2至18，优选a＝3至6；
◆作为基体无支链的或带支链的亚烯基
-CbH2b-CH＝CH-CcH2c- (III)
b+c＝2至16，此时b和c各自大于零。
◆作为基体无支链的或带支链的亚炔基
-CdH2d-C≡C-CeH2e- (IV)
d+e＝2至16，此时d和e各自大于零，且在式II至IV的基体上，间隔基团在链的任一位置上互相独立地含有0至4个羰基-、氨基-或酰氨基；
◆式V的亚脂环基
-CfH2f-环 C6H10-CgH2g- (V)
f和g同时互相独立地为1至6，
◆或式VI的亚脂环基
-3(4)，8(9)-二(亚甲基)-三环[5.2.1.02.6]癸烷- (VI)；
◆式VII的任选取代的亚芳基
或式VIII的任选取代的亚芳基
-ChH2h-C10R6-CjH2j- (VIII)
h、j、j1和j2时互相独立地为0至8，i＝1至8，以及R同时互相独立地为H或C1-至C4-烷基；
◆带有特别是氨基、酰氨基、羰基或羧基功能侧链基团的链
此外，间隔基团R2含有0至20，优选为1至12个氧原子和/或氮原子，0至4个硫原子以及0至3个磷原子，其中至少有一个杂原子出现一次。
此外，R2还特别具有下述含义
◆式IX的化合物
-CkH2k-CxRy-Z-CxRy-ClH2l- (IX)
k和l同时互相独立地为0至8，x＝6而y＝4或x＝10而y＝6或x＝14而y＝8，和
Z＝O，NH，NR1，N-C(O)R1，SO2，其中R1为1-22个碳原子的烃基，R相互独立地为H或C1-C4烷基；◆或式X的化合物
-CmH2m-(OCnH2n)p-CqH2q- (X)
m＝1至4，n＝2至4，p＝1至20，优选为p＝1至4，而q＝1至4，
此时也可有混合型烷氧化物单元出现，而烷氧化物单元的顺序可以是任意的，
◆式XI的化合物
-CrH2r(RNCsH2s)t-CuH2u- (XI)
或式XII化合物
-[CrH2r[RN-C(O)-NR]t-CuH2u]w- (XII)
或式XIII化合物
-[CrH2r[RNC(O)CvH2vC(O)NR]t-CuH2u]w- (XIII)
或式XIV化合物
-[CrH2r[RN-C(O)-CH＝CH-C(O)-NR]t-CuH2u]w- (XIV)
或式XV化合物
-[CrH2r[RNC(O)CxRyC(O)NR]t-CuH2u]w- (XV)
r＝2至4，s＝2至4，t＝1至20，优选t＝1至4，
u＝2至4，v＝0至12，w＝1至6，x＝6而y＝4，或
x＝10而y＝6，或
x＝14而y＝8
R同时互相独立地为H或C1-至C4-烷基。
X和Y互相独立地为式(XVI)的取代基
-(C2H4O)α(C3H6O)βH (XVI)
α＝0至50，优选为α＝10至20
β＝0至60，优选为β＝20至40
而α+β＝1至100，优选为α+β＝10至50，
其中当β＝0时，R2不是C2H4。
此时烷氧化物单元为统计的或以嵌段方式连接于其中，且其顺序是任意的。
或为XVII的取代基
-(C2H4O)γ(C3H6O)δ-FR (XVII)
γ＝0至20，优选为γ＝0至8
δ＝0至20，优选为δ＝0至12
而γ+δ＝1至40，优选为γ+δ＝5至20
此时FR为一个功能性基团
-CH2-COOM ，-SO3M，-P(O(OM)2，-O-C(O)-C2H3(SO3M)-CO2M1或
-C2H4-SO3M
M，M′＝碱金属、铵、链烷醇铵，或
1/2碱土金属，
或式XVIII的取代基团
-CH2[CHO(C2H4O)ε(C3H6O)ηH]z-CH2-O(C2H4O)μ(C3H6O)e-H (XVIII)
z＝3至6，优选z＝4，和
ε或μ＝0至30，优选ε和μ＝0至10，和
η或Q＝0至30，优选η或Q＝0至10
此时烷氧化物单元同样是统计的或以嵌段方式连接在其中，其顺序是任意的。
低聚度Z为1至10，优选Z＝1至4，特别优选Z＝1。
烷氧化度在所给出的界限内是一平均值，也可以是任意的非整数值。
本发明的两亲化合物大多数显示极低的临界胶束形成浓度(CMC)和很低的表面-和界面张力(例如与石蜡相比)，这是归因于它们特殊的结构-至少二个亲水基和至少二个疏水基，此外，它们中的大多数还显示相当高的亲水悬浮能力，大致位于常规的表面活性剂和三聚磷酸五钠之间。这些化合物中的一部分是极快的润湿剂。
本发明的两亲化合物特别适用作工业上和家用的乳化剂、反乳化剂、洗涤剂、分散剂和水溶助长剂，例如在金属加工、选矿、表面整理(加工)、洗涤和洁净，化妆品，药物行业和食品加工及制备过程。
在这方面它们可与所有常用的阴离子的、非离子的、阳离子的和两性界面活性物质复合。作为可用于复合的非离子界面活性物质的实例，可以列出脂肪酸甘油酯、脂肪酸多甘油酯、脂肪酸酯、乙氧基化的高级醇、聚氧乙烯脂肪酸甘油酯、聚氧乙烯丙二醇脂肪酸酯，聚氧乙烯脱水山梨醇脂肪酸酯、聚氧乙烯蓖麻油-或硬化蓖麻油衍生物，聚氧乙烯羊毛脂衍生物、聚氧乙烯脂肪酸酰胺、聚氧乙烯烷基胺、烷醇胺、烷基-胺氧化物、蛋白质水解物衍生体、羟基混合醚、烷基多甙类和烷基葡萄糖酰胺类。
作为可用于复合的阴离子界面活性物质的实例，可列出肥皂、醚羧酸及其盐类、烷基磺酸盐、α-烯磺酸盐、高级脂肪酸酯磺酸盐、高级醇硫酸盐、醇醚硫酸盐、羟基混合醚硫酸盐、磷酸酯的盐类、牛磺酸盐、羟乙磺酸盐、线型烷基苯磺酸盐、异丙基磺酸盐、烷基芳基磺酸盐、聚氧乙烯脂肪酸酰胺的硫酸盐和酰氨基酸的盐类。
作为可用于复合的阳离子常用界面活性物质的实例，可列出烷基三甲基铵盐、二烷基二甲基铵盐、烷基二甲基苄基铵盐、烷基吡啶鎓盐、烷基异喹啉鎓盐、苄索氯铵和阳离子酰氨基酸衍生物。
作为可用于复合的两性界面活性物质的实例，可列出氨基酸、甜菜碱、磺基甜菜碱、咪唑啉衍生物、豆油类脂化合物(磷脂)和卵磷脂。
此外，本发明的两亲化合物也能互相复合使用。
本发明的两亲化合物同样通常作为助剂应用，这种助剂选用于专用配方，并通常包括无机盐类，如氯化钠和硫酸钠以及助洗剂、水溶助洗剂、紫外线吸收剂、增塑剂、螯合物组分、粘度改性剂和香料。
上述的化合物可按已知方法制造：优选在催化剂存在下，于高温(80-180℃)温度使二-或低聚胺与相对于每一个自由NH-官能团为1当量数量的脂肪酸或脂肪酸甲酯反应，其间真空除去生成的水或甲醇。然后在130-190℃在碱性催化剂存在下进行烷氧化。这种液体产物或在较低温度下软化的产物可接着与三氧化硫/惰性气体(发烟硫酸或氯磺酸)或多磷酸，或与卤代醋酸，磺内酯，或与羟乙磺酸反应，并用碱金属-或碱土金属氢氧化物水溶液或氨水溶液或链烷醇胺中和。在需要时将产品在水溶液中用过氧化氢(为固体物的0.1至2.0％)进行漂白。
实例
下列实例是对发明的进一步描述，但它不止限于此。所有百分比均为重量百分比。
实例1：
R1＝R3＝-C7H15/-C9H19(1∶1)，R2＝-C2H4-，X，Y＝-(C2H4O)5SO3Na
在带有搅拌器、温度计、脱水器和回流冷凝器的1升四口烧瓶中混合91.8克乙二胺和441.5克辛酸-和癸酸甲酯(1∶1)的混合物，并加热至120-140℃。在7小时内，排出72.3ml甲醇，接着结束反应。三种由同系物混合物产生的二酰胺的纯度用13C-NMR确定，并＞99摩尔％，收率447.2g(理论值的85％)。
将170.0g二酰胺混合物与150ml白油混合，并用1.1g固体氢氧化钾处理。在160℃使混合物与220g环氧乙烷反应6小时。催化剂用乳酸中和，滤掉沉淀的钾盐及可能未反应的二酰胺。经称量产物来证实环氧乙烷全部转化的情况，用13C-NMR确定环氧乙烷与残余分子的比例：10 EO-单元/残余分子。
收率390g(定量)，IR表明产物混合物中无残留N-H-官能团。
向117.7g氯磺酸和60.2g乙酸的混合物中滴入于300ml二氯甲烷中的218.5g所得乙氧化物，使温度不超过5℃。接着在室温搅拌3小时(经薄层色谱检测，乙氧化物全部反应)。用2N碳酸钠溶液中和，并用饱和碳酸氢钠溶液稀释。用正丁醇萃取产物，接着除去乙醇。
用薄层色谱和NMR检测纯度。
收率：96.8g(理论值的36％)，纯度：90％，13C-NMR性质数据(DMSO-D6)：
171，8ppm，69，2ppm，68，7ppm，67，8ppm，64，6ppm62，3ppm，32，9ppm，30，7ppm，27，9-28，3ppm，24ppm(宽)，21，9ppm，13，1ppm；CMC：0，011g/l，γCMC＝30mN/m(VE-水中，20℃)，γ石蜡＝2，5mN/m(0，1g/l WAS VE-水中，20℃).实例2
R1＝R3＝-C7H15/-C9H19(1∶1)， R2＝-C2H4-，X，Y＝-(C2H4O)10SO3Na
如实例1进行反应：
如实例1制得二酰胺混合物。
乙氧基化：170g二酰胺混合物，150ml白油，440g环氧乙烷，1.1gKOH，NMR表明每残留分子有20EO单元。收率610g(定量)。
硫酸化：
217.5g乙氧化物，78.8g氯磺酸，40.3g乙酸，
收率123.7g(理论值的50％)，纯度：90％，13C-NMR特性数据：
(DMSO-D6)：172，0ppm，69，4ppm，69，1ppm，65，2ppm，28，5ppm(宽)，21，1ppm，13，4ppm；CMC：0，13g/l，γCMC＝33mN/m(VE-水中，20℃)，γ石蜡＝15，5mN/m(0，1g/lWAS在VE-水中，20℃).实例3
R1＝R3＝-C7H15/-C9H19(1∶1)，R2＝-C6H12-，X，Y＝-(C2H4O)8SO3Na
反应按实例1进行。
116.2g己二胺，344.0g辛酸-和癸酸混合物(1∶1)，0.2g ZnO，
反应时间：7小时，反应温度：140-145℃，二酰胺混合物收率：465g，纯度：＞95％。
乙氧基化：170g二酰胺混合物，150ml白油，292g环氧乙烷，1.1g KOH，
乙氧化物收率：370g，每残留分子有8 EO-单元。
硫酸化：类似实例1
收率105.4g(理论值的62％)，纯度：92％，13C-NMR特性数据：(DMSO-D6)：173，4ppm(宽)，70，4ppm，69，3ppm，68，9ppm，68，1ppm，33，1ppm，28 bis 29ppm(宽)，22，0ppm，13，0ppm；CMC：0，016g/l，γCMC＝28，5mN/m(VE-水中，20℃)，γ石蜡＝3，0mN/m(0，1g/l WAS VE-水中，20℃).
Claims (19)
1.通式I的两亲化合物
其中R1和R3互相独立地为1至22个碳原子的烃基，
R2为间隔基团，和
X和Y互相独立地为取代基，并且低聚度Z＝1至10。
2.按权利要求1的两亲化合物，其特征在于，烃基R1和R3为非支链或带支链的饱和或非饱和的，
间隔基团R2为非支链或带支链的2至100个碳原子的链，它含有0至20个氧和氮原子，0至4个硫原子和0至3个磷原子，并具有0至20个功能性侧链基，和
X和Y互相独立地为烷氧基化的或非烷氧基化的取代基。
3.按权利要求1或2的两亲化合物，其特征在于低聚度Z＝1至4，优选Z＝1。
4.按权利要求1和3之一的两亲化合物，其特征在于，式I中的烃基R1和R3互相独立地含有7至17个碳原子。
5.按权利要求1至4之一的两亲化合物，其特征在于，R2为间隔基团，它含有作为基体的式II的非支链的或带支链的亚烷基链
-CaH2a- (II)
a＝2至18，优选a＝3至6，
或含式III非支链或带支链的亚烯基链
-CbH2b-CH＝CH-CcH2c- (III)
b+c＝2至16，其中b和c各自都大于零，
或者含式IV的非支链或带支链的亚炔基链
-CdH2d-C≡C-CeH2e- (IV)
d+e＝2至16，其中d和e各自都大于零，
并且在式(II)至(IV)的基体中，间隔基团可在链的任何位置含有0至4个羰基、氨基或酰氨基。
6.按权利要求1至4之一的两亲化合物，其特征在于，R2为间隔基团，它由式V的亚脂环基
-CfH2f-环C6H10-CgH2g- (V)
f和g互相独立地各为1至6，
或式VI的亚脂环基
-3(4)，8(9)-二(亚甲基)-三环 [5.2.1.02.6]癸烷- (VI)组成。
7.按权利要求1至4之一的两亲化合物，其特征在于，R2为间隔基团，它由式VII或式VIII的非取代或取代的芳烃基组成，
-ChH2h-C10R6-CjH2j- (VIII)
h、j、j1和j2互相独立地各自为0至8，且i＝1至8，以及
R同时互相独立地各自为H或C1-至C4-烷基。
8.按权利要求1至5之一的两亲化合物，其特征在于，间隔基团R2带有功能性侧链基团，特别是氨基、酰氨基、羰基或羧基。
9.按权利要求1至5之一的两亲化合物，其特征在于，间隔基团R2含有0至20，优选1至12个氧原子和/或氮原子，0至4个硫原子和0至3个磷原子，其中至少有一个杂原子出现至少一次。
10.按权利要求9的两亲化合物，其特征在于，R2为式IX的间隔基团
-CkH2k-CxRy-Z-CxRy-ClH2l- (IX)
k和l互相独立地为0至8，x＝6和y＝4或x＝10和y＝6或x＝14和y＝8，以及
Z＝O，CO，NH，NR1，N-C(O)R1，SO2，其中R1为1-22个碳原子的烃基，R各自独立地为H或C1-C4烷基。
11.按权利要求9的两亲化合物，其特征在于，R2为式X的间隔基团
-CmH2m-(CnH2nO)p-CqH2q- (X)
m＝1至4，n＝2至4，p＝1至20，优选为p＝1至4和q＝1至4
其中也可有混合型烷氧化物单元存在，而烷氧化物单元的顺序是任意的。
12.按权利要求9的两亲化合物，其特征在于，R2为式XI或式XII或式XIII或式XIV或式XV的间隔基团，
-CrH2r(RNCsH2s)t-CuH2u- (XI)
-[CrH2r[RN-C(O)-NR]t-CuH2u]w- (XII)
-[CrH2r[RNC(0)CvH2vC(0)NR]t-CuH2u]w- (XIII)
-[CrH2r[RN-C(O)-CH＝CH-C(O)-NR]t-CuH2u]w- (XIV)
-[CrH2r[RNC(O)CxRyC(O)NR]t-CuH2u]w- (XV)
r＝2至4，s＝2至4，t＝1至20，优选t＝1至4，
u＝2至4，v＝0至12，w＝1至6，x＝6和y＝4，或
x＝10和y＝6，或
x＝14和y＝8
R互相独立地为H或C1-至C4-烷基。
13.按权利要求1-12之一的两亲化合物，其特征在于，X和Y互相独立地为式XVI的取代基
-(C2H40)α(C3H6O)βH (XVI)
α＝0至50，优选α＝10至30，
β＝0至60，优选β＝20至40，
而α+β＝1至100，优选α+β＝10至50，
其中当β＝0时，R2不是C2H4，
其中烷氧化物单元为统计的或以嵌段方式连接，其顺序是任意的。
14.按权利要求1至12之一的两亲化合物，其特征在于，X和Y独立地为式XVII的取代基，
-(C2H4O)γ(C3H6O)δ-FR (XVII)
γ＝0至20，优选γ＝0至8
δ＝0至20，优选δ＝0至12
而γ+δ＝1至40，优选γ+δ＝5至20，
其中FR为功能性基团
-CH2-COOM，-SO3M，-P(O(OM)2，-O-C(O)-C2H3(SO3M)-CO2M1或
-C2H4-SO3M
M，M′＝碱金属、铵、链烷醇铵，或
1/2碱土金属，
或式XVIII的取代基团
-CH2[CHO(C2H4O)ε(C3H6O)ηH]z-CH2-O(C2H4O)μ(C3H6O)Q-H (XVIII)
z＝3至6，优选z＝4，
和ε或μ＝0至30，优选ε或μ＝0至10，
和η或Q＝0至30，优选η或Q＝0至10，
并且其中烷氧化物单元是统计的或以嵌段方式连接，其顺序是任意的。
15.权利要求1至14之一的两亲化合物作为乳化剂或反乳化剂的应用。
16.权利要求1至14之一的两亲化合物在金属加工、采矿或表面处理中作为助剂的应用。
17.权利要求1至14之一的两亲化合物作为纺织助剂或用于纺织品的清净和洗涤中的应用。
18.权利要求1至14之一的两亲化合物在硬表面的清净中的应用。
19.权利要求1至14之一的两亲化合物用于皮肤和头发的清净和洗涤中的应用。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4440328A DE4440328A1 (de) | 1994-11-11 | 1994-11-11 | Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Amiden |
| DEP4440328.3 | 1994-11-11 |
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| Publication Number | Publication Date |
|---|---|
| CN1172439A true CN1172439A (zh) | 1998-02-04 |
| CN1090051C CN1090051C (zh) | 2002-09-04 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95197305A Expired - Lifetime CN1090051C (zh) | 1994-11-11 | 1995-09-15 | 以酰胺为基础的带有至少二个亲水基和至少二个疏水基的两亲化合物 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6342625B1 (zh) |
| EP (1) | EP0804279B1 (zh) |
| JP (1) | JP4390021B2 (zh) |
| CN (1) | CN1090051C (zh) |
| AT (1) | ATE210493T1 (zh) |
| AU (1) | AU689649B2 (zh) |
| BR (1) | BR9509636A (zh) |
| DE (2) | DE4440328A1 (zh) |
| ES (1) | ES2171194T3 (zh) |
| TR (1) | TR199501368A2 (zh) |
| WO (1) | WO1996014926A1 (zh) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101302296B (zh) * | 2008-06-03 | 2010-08-25 | 江南大学 | 一种双亲性共聚物自组装胶束乳化剂的制备方法 |
| CN101554569B (zh) * | 2009-04-21 | 2012-06-27 | 西安楚龙达化工有限公司 | 一种阴离子型Gemini表面活性剂的合成方法 |
| CN109364530A (zh) * | 2018-11-27 | 2019-02-22 | 浙江大学 | 一种对水包油型乳状液进行破乳的方法 |
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|---|---|---|---|---|
| WO1997023449A1 (en) * | 1995-12-21 | 1997-07-03 | Rhone-Poulenc Inc. | Anionic surfactants having multiple hydrophobic and hydrophilic groups |
| DE19616096A1 (de) * | 1996-04-23 | 1997-11-06 | Huels Chemische Werke Ag | Verwendung von anionischen Geminitensiden in Formulierungen für Wasch-, Reinigungs- und Körperpflegemittel |
| DE19625937A1 (de) * | 1996-06-28 | 1997-01-23 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Mono-, Di- oder Oligoamidalkoxylaten |
| AU4393097A (en) * | 1996-10-04 | 1998-05-05 | Rhodia Inc. | Detergent compositions containing low concentration levels of gemini surfactan ts |
| US6121222A (en) * | 1996-12-27 | 2000-09-19 | Rhodia Inc. | Anionic surfactants having multiple hydrophobic and hydrophilic groups |
| DE19943668A1 (de) | 1999-09-13 | 2001-03-15 | Rwe Dea Ag | Tensidzusammensetzung enthaltend Geminitenside und Co-Amphiphile, ihre Herstellung und ihre Verwendung |
| US6649138B2 (en) * | 2000-10-13 | 2003-11-18 | Quantum Dot Corporation | Surface-modified semiconductive and metallic nanoparticles having enhanced dispersibility in aqueous media |
| DE102007063134A1 (de) | 2007-12-24 | 2009-06-25 | Sasol Germany Gmbh | Verfahren zur Herstellung von Öl in Wasser Emulsionen aus selbstemulgierenden Gelkonzentraten |
| DE102007063133A1 (de) | 2007-12-24 | 2009-06-25 | Sasol Germany Gmbh | Verfahren zur Herstellung von Wachs in Wasser Dispersionen aus selbstemulgierenden Gelkonzentraten |
| FR2956579B1 (fr) | 2010-02-24 | 2012-02-10 | Oreal | Composition comprenant un polymere superabsorbant et tensioactif gemine |
| FR2967056B1 (fr) | 2010-11-05 | 2012-11-09 | Oreal | Composition solaire fluide aqueuse a base d'un polymere superabsorbant et d'un copolymere reticule d'acide methacrylique et d'acrylate d'alkyle en c1-c4. |
| WO2012095786A2 (en) | 2011-01-11 | 2012-07-19 | L'oreal | Anti-uv cosmetic composition |
| FR2971151B1 (fr) | 2011-02-04 | 2013-07-12 | Oreal | Composition cosmetique contenant des particules filtrantes de materiau composite, des particules non filtrantes non-spheriques et au moins une huile polaire |
| FR2971149B1 (fr) | 2011-02-04 | 2013-07-12 | Oreal | Composition cosmetique contenant un melange de particules filtrantes de materiau composite spheriques et non spheriques |
| WO2012105060A1 (en) | 2011-02-04 | 2012-08-09 | L'oreal | Composite pigment and method for preparation thereof |
| WO2013010590A1 (en) | 2011-07-21 | 2013-01-24 | L'oreal | Cosmetic and/or dermatological composition containing a merocyanine derivative comprising specific polar groups consisting of hydroxyl- and ether-functionalities |
| FR2989886B1 (fr) | 2012-04-26 | 2016-12-09 | Oreal | Composition comprenant un silane et un tensioactif gemine |
| JP6096898B2 (ja) | 2012-07-13 | 2017-03-15 | ロレアル | 化粧料組成物 |
| ES2822151T5 (es) | 2012-07-13 | 2024-03-18 | Oreal | Pigmento compuesto y procedimiento para prepararlo |
| FR3001131B1 (fr) | 2013-01-21 | 2015-06-19 | Oreal | Emulsion cosmetique ou dermatologique comprenant une merocyanine et un systeme emulsionnant contenant un tensioactif gemine. |
| CN103566816B (zh) * | 2013-10-22 | 2016-03-23 | 中国石油化工股份有限公司 | 一种三聚酰胺类非离子型表面活性剂及制备方法和用途 |
| FR3068354B1 (fr) | 2017-06-29 | 2020-07-31 | Oreal | Compositions photoprotectrices comprenant un derive dibenzoylmethane, un compose merocyanine et un compose susceptible d'accepter l'energie de niveau excite triplet du compose dibenzoylmethane |
| WO2020163928A1 (en) | 2019-02-13 | 2020-08-20 | L'oreal | Sunscreen composition, use of the sunscreen composition and process of manufacturing the sunscreen composition |
| EP4175609A1 (en) | 2020-07-02 | 2023-05-10 | L'oreal | Cosmetic composition comprising polymers |
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| JPS6096695A (ja) | 1983-10-31 | 1985-05-30 | 三洋化成工業株式会社 | 洗浄剤組成物 |
| EP0258923B1 (en) * | 1986-09-02 | 1993-10-06 | Akzo Nobel N.V. | Fabric softening composition and detergent-composition comprising the same |
| GB9018157D0 (en) * | 1990-08-17 | 1990-10-03 | Procter & Gamble | Detergent compositions |
| JP2907517B2 (ja) | 1990-09-12 | 1999-06-21 | 鐘紡株式会社 | 二鎖または三鎖二親水基型化合物 |
| US5160450A (en) | 1990-12-05 | 1992-11-03 | Lion Corporation | Surface-active agents having two hydrophobic chains and two hydrophilic groups |
| DE4227894A1 (de) | 1992-08-22 | 1994-02-24 | Basf Ag | Verfahren zur Reduktion organischer Bestandteile in Abwässern aus gewerblichen Wäschereien |
| SE9303458L (sv) | 1993-10-21 | 1994-10-03 | Berol Nobel Ab | Användning av en amfotär tensid som friktionsreducerande medel i ett vattenbaserat vätskesystem |
| WO1995019955A1 (en) * | 1994-01-25 | 1995-07-27 | The Procter & Gamble Company | Gemini polyether fatty acid amides and their use in detergent compositions |
| DE19505368A1 (de) * | 1995-02-17 | 1996-08-22 | Huels Chemische Werke Ag | Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Dicarbonsäurediamiden |
-
1994
- 1994-11-11 DE DE4440328A patent/DE4440328A1/de not_active Withdrawn
-
1995
- 1995-09-15 EP EP95932759A patent/EP0804279B1/de not_active Expired - Lifetime
- 1995-09-15 WO PCT/EP1995/003635 patent/WO1996014926A1/de active IP Right Grant
- 1995-09-15 DE DE59509951T patent/DE59509951D1/de not_active Expired - Lifetime
- 1995-09-15 ES ES95932759T patent/ES2171194T3/es not_active Expired - Lifetime
- 1995-09-15 AT AT95932759T patent/ATE210493T1/de not_active IP Right Cessation
- 1995-09-15 US US08/817,930 patent/US6342625B1/en not_active Expired - Lifetime
- 1995-09-15 BR BR9509636A patent/BR9509636A/pt not_active IP Right Cessation
- 1995-09-15 AU AU35678/95A patent/AU689649B2/en not_active Ceased
- 1995-09-15 JP JP51566496A patent/JP4390021B2/ja not_active Expired - Fee Related
- 1995-09-15 CN CN95197305A patent/CN1090051C/zh not_active Expired - Lifetime
- 1995-11-03 TR TR95/01368A patent/TR199501368A2/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101302296B (zh) * | 2008-06-03 | 2010-08-25 | 江南大学 | 一种双亲性共聚物自组装胶束乳化剂的制备方法 |
| CN101554569B (zh) * | 2009-04-21 | 2012-06-27 | 西安楚龙达化工有限公司 | 一种阴离子型Gemini表面活性剂的合成方法 |
| CN109364530A (zh) * | 2018-11-27 | 2019-02-22 | 浙江大学 | 一种对水包油型乳状液进行破乳的方法 |
| CN109364530B (zh) * | 2018-11-27 | 2020-11-24 | 浙江大学 | 一种对水包油型乳状液进行破乳的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59509951D1 (de) | 2002-01-24 |
| DE4440328A1 (de) | 1996-05-15 |
| TR199501368A2 (tr) | 1996-06-21 |
| ATE210493T1 (de) | 2001-12-15 |
| EP0804279B1 (de) | 2001-12-12 |
| JP4390021B2 (ja) | 2009-12-24 |
| JPH10511932A (ja) | 1998-11-17 |
| AU3567895A (en) | 1996-06-06 |
| AU689649B2 (en) | 1998-04-02 |
| CN1090051C (zh) | 2002-09-04 |
| ES2171194T3 (es) | 2002-09-01 |
| WO1996014926A1 (de) | 1996-05-23 |
| BR9509636A (pt) | 1997-10-14 |
| US6342625B1 (en) | 2002-01-29 |
| EP0804279A1 (de) | 1997-11-05 |
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