WO1996018610A1 - Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base d'esters - Google Patents
Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base d'esters Download PDFInfo
- Publication number
- WO1996018610A1 WO1996018610A1 PCT/EP1995/003583 EP9503583W WO9618610A1 WO 1996018610 A1 WO1996018610 A1 WO 1996018610A1 EP 9503583 W EP9503583 W EP 9503583W WO 9618610 A1 WO9618610 A1 WO 9618610A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- amphiphilic compounds
- compounds according
- spacer
- independently
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 37
- 125000001165 hydrophobic group Chemical group 0.000 title abstract description 8
- 150000002148 esters Chemical class 0.000 title abstract description 4
- 238000004140 cleaning Methods 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 4
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 3
- 238000000605 extraction Methods 0.000 claims abstract description 3
- 125000006850 spacer group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 150000004703 alkoxides Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 150000001241 acetals Chemical class 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 238000005555 metalworking Methods 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 238000004381 surface treatment Methods 0.000 claims 1
- -1 demulsifiers Substances 0.000 abstract description 34
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000003599 detergent Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 230000003165 hydrotropic effect Effects 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 229920002601 oligoester Polymers 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- JBVOQKNLGSOPNZ-UHFFFAOYSA-N 2-propan-2-ylbenzenesulfonic acid Chemical class CC(C)C1=CC=CC=C1S(O)(=O)=O JBVOQKNLGSOPNZ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960003872 benzethonium Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002960 margaryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 238000005457 optimization Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C09K23/08—Sulfation or sulfonation products of fats, oils, waxes, or higher fatty acids or esters thereof with monovalent alcohols
-
- 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
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
-
- 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
-
- 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
Definitions
- the invention relates to amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on esters.
- amphiphilic substances A wide variety of anionic, cationic, nonionic and zwitterionic compounds are known as amphiphilic substances. The vast majority of these substances consist of a hydrophilic head group and at least one hydrophobic part.
- amphiphilic substances there are ecological reasons, e.g. B. bezüg ⁇ Lich the reduction in packaging and transportation, the need to achieve ever greater effect per mass of substance used. Since optimization by mixing amphiphilic substances only continues to a very limited extent, new amphiphilic substances with a higher degree of efficiency are required. In particular, substances with lower critical micelle formation concentrations and / or lower surface and interfacial tensions have to be found in order to be able to significantly reduce the amount of active substance used.
- cationic surface-active compounds can be obtained by adding long-chain alkyl halides to permethylated alkylenediamines [R. Zana, M. Benrraou, R. Rueff, Langmuir, (1991) 1072; R. Zana, Y. Talmon, Nature, 362 (1993) 228; E. Alami, G. Beinert, P. Marie, R. Zana, Langmuir, 9 (1993) 1465].
- Anionic surface-active compounds with at least two hydrophilic and at least two hydrophobic groups have hitherto been produced only on the basis of diglycidyl ethers (US Pat. No. 5,160,450, JP 01,304,033, JP 4,124,165).
- diglycidyl ethers are considered toxicologically unsafe and are quite expensive.
- epichlorohydrin is used for their production, which leads to large amounts of residues, so that these compounds are no longer appropriate from an ecotoxicological as well as an economical point of view.
- amphiphilic compounds which have at least two hydrophilic and at least two hydrophobic groups, the amphiphilic compounds having a very high degree of effectiveness, based on the amount used, and which are also made from readily available raw materials which are not technically large Accidental by-products can be produced.
- amphiphilic di- or oligoesters the base of which can be prepared from di-, oligo- or polyols and fatty acids or fatty acid methyl esters.
- the corresponding di- or oligoesters can be sulfonated.
- sulfonated fatty acid methyl esters can also be transesterified with di-, oligo- or polyols and then neutralized.
- amphiphilic compounds according to the invention are compounds of the general formula I.
- R, R, R, M and M 'in formula I have the meanings described below:
- R and R independently of one another represent an unbranched or branched, saturated or unsaturated hydrocarbon radical having 1 to 22, preferably 6 to 18 carbon atoms.
- R and R are in particular the radicals methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n -
- R means a spacer consisting of an unbranched or branched
- the spacer R means in particular
- the spacer can additionally contain 1 to 4 carbonyl, carboxyl, amino or acylamino groups at any point in the chain;
- the spacer R further contains 0 to 20, preferably 1 to 12, oxygen and / or nitrogen atoms, 0 to 4 sulfur and 0 to 3 phosphorus atoms, at least one of the heteroatoms occurring at least once.
- amphiphilic compounds according to the invention are usually characterized by extremely low critical micelle formation concentrations (CMC) and very low surface and interfacial tensions (e.g. against paraffin), which is due to their special structure - at least two hydrophilic groups and at least two hydrophobic groups - must be returned.
- CMC critical micelle formation concentrations
- hydrophilic suspending capacity is about halfway between that of conventional surfactants and that of pentasodium tripolyphosphate.
- amphiphilic compounds according to this invention are particularly suitable as emulsifiers, demulsifiers, detergents, dispersants and hydrotropes in industry and in the home, for example in the fields of metalworking, ore extraction, surface finishing, washing and cleaning, cosmetics, medicine and food processing and preparation.
- nonionic surface-active substances which can be used for a combination include fatty acid glycerides, fatty acid polyglycerides, fatty acid esters, ethoxylates of higher alcohols, polyoxyethylene fatty acid glycerides, polyoxyethylene propylene glycol fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene-dericinoleedirate, or urethane oil derivatives, or polyoxyethylene-dericin derivative or di-urethane oil derivatives , Polyoxyethylene fatty acid amides, polyoxyethylene alkylamines, alkanolamines, alkyl amine oxides, derivatives of protein hydrolyzates, hydroxy mixed ethers, alkyl polyglycosides and alkyl glucamides.
- anionic surface-active substances that can be used for combinations are soaps, ether carboxylic acids and their salts, alkyl sulfonates, o-olefin sulfonates, sulfonates of higher fatty acid esters, higher alcohol sulfates, alcohol ether sulfates, hydroxymixed ether sulfates, salts of phosphate esters, taurides, isethionates , linear alkylbenzenesulfonates, cumene sulfonates, alkylarylsulfonates, sulfates of polyoxyethylene fatty acid ide and salts of acylamino acids.
- cationic common surface-active substances examples include aikyltrimethylammonium salts, dialkyldimethylammonium salts, alkyldimethylbenzylam onium salts, alkylpyridine salts, alkylisoquinolinium salts, benzethonium chlorides and cationic acylamino acid derivatives.
- ampholytic surface-active substances examples include amino acids, betaines, sulfobetaines, imidazoline derivatives, soybean lipids and lecithin.
- amphiphilic compounds according to the invention can also be combined with one another.
- additives can also be added to the amphiphilic compounds according to the invention.
- Such additives are specially selected for a formulation and usually include inorganic salts such as sodium chloride and sulfate, as well as builders, hydrotropics, UV absorbers, plasticizers, chelating agents, viscosity modifiers and fragrances.
- the abovementioned compounds can be prepared from di-, oligo- or polyols and at least twice the equivalent of sulfonated fatty acid methyl esters or by at least double sulfonation of the di-, oligo- or polyester and with aqueous alkali or alkaline earth metal hydroxides or aqueous ammonia or neutralize alkanols. If necessary, the products are bleached in aqueous solution with hydrogen peroxide (0.1 to 2.0%, based on solids).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
L'invention concerne des composés amphiphiles de formule générale (I), comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes à base d'esters. Ces composés amphiphiles sont généralement tensioactifs et sont utilisés en particulier sous forme d'émulsifiants, désémulsifiants, détergents, agents dispersants et hydrotropes, à usage industriel et domestique, par exemple dans les domaines de l'usinage des métaux, de l'extraction de minerais, du traitement de surface, du lavage et du nettoyage, des cosmétiques, de la médecine, du traitement et de la préparation des aliments.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU35661/95A AU3566195A (en) | 1994-12-17 | 1995-09-12 | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on esters |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4445133.4 | 1994-12-17 | ||
| DE4445133A DE4445133A1 (de) | 1994-12-17 | 1994-12-17 | Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Estern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1996018610A1 true WO1996018610A1 (fr) | 1996-06-20 |
Family
ID=6536160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1995/003583 WO1996018610A1 (fr) | 1994-12-17 | 1995-09-12 | Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base d'esters |
Country Status (4)
| Country | Link |
|---|---|
| AU (1) | AU3566195A (fr) |
| DE (1) | DE4445133A1 (fr) |
| WO (1) | WO1996018610A1 (fr) |
| ZA (1) | ZA9510680B (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997009304A1 (fr) * | 1995-09-01 | 1997-03-13 | HÜLS Aktiengesellschaft | Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2166142A (en) * | 1937-01-21 | 1939-07-18 | Benjamin R Harris | Sulphocarboxylic acid esters |
| US2460968A (en) * | 1943-09-28 | 1949-02-08 | Innovations Chimiques Sinnova | Method for the obtainment of aliphatic sulfonic acids and esters thereof |
| CH273548A (de) * | 1949-02-04 | 1951-02-15 | Hoffmann La Roche | Verfahren zur Darstellung eines wasserlöslichen Stilböstrolderivates. |
| US3173940A (en) * | 1962-04-16 | 1965-03-16 | Eastman Kodak Co | Polyoxyloweralkylene glycol di alpha-sulpho monocarboxylates and salts thereof |
| US3268563A (en) * | 1962-05-03 | 1966-08-23 | Petrolite Corp | Esters of an alpha-sulfo carboxylic acid and a glycol |
| WO1993025646A1 (fr) * | 1992-06-17 | 1993-12-23 | Lion Corporation | Composition detergente peu agressive pour la peau |
| DE4300935A1 (de) * | 1993-01-15 | 1994-07-21 | Henkel Kgaa | Sulfonierte Diester |
-
1994
- 1994-12-17 DE DE4445133A patent/DE4445133A1/de not_active Withdrawn
-
1995
- 1995-09-12 AU AU35661/95A patent/AU3566195A/en not_active Abandoned
- 1995-09-12 WO PCT/EP1995/003583 patent/WO1996018610A1/fr active Application Filing
- 1995-12-15 ZA ZA9510680A patent/ZA9510680B/xx unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2166142A (en) * | 1937-01-21 | 1939-07-18 | Benjamin R Harris | Sulphocarboxylic acid esters |
| US2460968A (en) * | 1943-09-28 | 1949-02-08 | Innovations Chimiques Sinnova | Method for the obtainment of aliphatic sulfonic acids and esters thereof |
| CH273548A (de) * | 1949-02-04 | 1951-02-15 | Hoffmann La Roche | Verfahren zur Darstellung eines wasserlöslichen Stilböstrolderivates. |
| US3173940A (en) * | 1962-04-16 | 1965-03-16 | Eastman Kodak Co | Polyoxyloweralkylene glycol di alpha-sulpho monocarboxylates and salts thereof |
| US3268563A (en) * | 1962-05-03 | 1966-08-23 | Petrolite Corp | Esters of an alpha-sulfo carboxylic acid and a glycol |
| WO1993025646A1 (fr) * | 1992-06-17 | 1993-12-23 | Lion Corporation | Composition detergente peu agressive pour la peau |
| DE4300935A1 (de) * | 1993-01-15 | 1994-07-21 | Henkel Kgaa | Sulfonierte Diester |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997009304A1 (fr) * | 1995-09-01 | 1997-03-13 | HÜLS Aktiengesellschaft | Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA9510680B (en) | 1996-07-13 |
| DE4445133A1 (de) | 1996-06-20 |
| AU3566195A (en) | 1996-07-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0804279B1 (fr) | Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base d'amides | |
| EP0809625B1 (fr) | Composes amphiphiles anioniques, comportant au moins deux groupements hydrophiles et au moins deux groupements hydrophobes, a base de diamides d'acides dicarboxyliques | |
| EP0885185B1 (fr) | Tensioactifs jumeles betainiques a base d'amines | |
| EP0793647B1 (fr) | Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base de di, oligo ou polyolethers | |
| EP0809628B1 (fr) | Composes amphiphiles, comportant au moins deux groupements hydrophiles et au moins deux groupements hydrophobes, a base de diesters d'acides dicarboxyliques | |
| EP0836590B1 (fr) | Composes amphiphiles avec plusieurs groupes hydrophiles et hydrophobes a base d'amines alcoxylees et/ou d'amides alcoxyles et d'acides di-, oligo- ou polycarboxyliques | |
| EP0876328B1 (fr) | Composes amphiphiles a plusieurs groupes hydrophiles et hydrophobes a base de derives d'acide carbonique | |
| WO1996018610A1 (fr) | Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base d'esters | |
| EP0641377B1 (fr) | Melanges de tensioactifs doux | |
| EP0927158A1 (fr) | Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base de diesters d'acide dicarboxylique | |
| WO1997007089A1 (fr) | Composes amphiphiles a plusieurs groupes hydrophiles et hydrophobes a base de derives d'acide aminosuccinique | |
| EP0847385A1 (fr) | Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene | |
| EP0977732B1 (fr) | Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base de dienes, d'oligo-enes ou de polyenes | |
| WO2017198527A1 (fr) | Compositions tensio-actives aqueuses | |
| DE3051165C2 (de) | Gemisch von nicht-ionogenen Tensiden, Verfahren zur Herstellung desselben und Mittel, die dieses enthalten | |
| DE19748399A1 (de) | Sulfatierte Pseudoceramide | |
| CN1179772A (zh) | 以二羧酸二酯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 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): AU BG BR BY CA CN CZ EE HU JP LT LV PL RO RU SI SK UA US VN |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE |
|
| DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| 122 | Ep: pct application non-entry in european phase | ||
| NENP | Non-entry into the national phase |
Ref country code: CA |