EP0475967A1 - Alkylsulfates gras et alkylpolyalkylene-glycolethersulfates gras; leur procede de production et leur utilisation - Google Patents
Alkylsulfates gras et alkylpolyalkylene-glycolethersulfates gras; leur procede de production et leur utilisationInfo
- Publication number
- EP0475967A1 EP0475967A1 EP90908223A EP90908223A EP0475967A1 EP 0475967 A1 EP0475967 A1 EP 0475967A1 EP 90908223 A EP90908223 A EP 90908223A EP 90908223 A EP90908223 A EP 90908223A EP 0475967 A1 EP0475967 A1 EP 0475967A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- isostearyl
- polyalkylene glycol
- sulfates
- glycol ethers
- sulfation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- -1 alkyl sulphates Chemical class 0.000 title claims abstract description 44
- 229920001521 polyalkylene glycol ether Polymers 0.000 title claims abstract description 30
- 150000003467 sulfuric acid derivatives Chemical class 0.000 title claims description 22
- 125000000217 alkyl group Chemical group 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 claims description 62
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 28
- 230000019635 sulfation Effects 0.000 claims description 18
- 238000005670 sulfation reaction Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 12
- 230000001180 sulfating effect Effects 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 238000006386 neutralization reaction Methods 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 239000003599 detergent Substances 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 150000004679 hydroxides Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- TURPNXCLLLFJAP-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl hydrogen sulfate Chemical compound OCCOCCOCCOS(O)(=O)=O TURPNXCLLLFJAP-UHFFFAOYSA-N 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 11
- 230000003472 neutralizing effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 13
- 150000008051 alkyl sulfates Chemical class 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000003945 anionic surfactant Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- VIUJGOYYZXDUPO-UHFFFAOYSA-N 16-methyl-1-(16-methylheptadecoxy)heptadecane sulfuric acid Chemical class OS(O)(=O)=O.CC(C)CCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC(C)C VIUJGOYYZXDUPO-UHFFFAOYSA-N 0.000 description 3
- WWKJSUQDMGKSIF-UHFFFAOYSA-N 16-methylheptadecyl hydrogen sulfate Chemical compound CC(C)CCCCCCCCCCCCCCCOS(O)(=O)=O WWKJSUQDMGKSIF-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- JBVOQKNLGSOPNZ-UHFFFAOYSA-N 2-propan-2-ylbenzenesulfonic acid Chemical compound CC(C)C1=CC=CC=C1S(O)(=O)=O JBVOQKNLGSOPNZ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940071118 cumenesulfonate Drugs 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
-
- 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
- C07C305/06—Hydrogenosulfates
-
- 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
- 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
- C11D1/29—Sulfates of polyoxyalkylene ethers
Definitions
- Fatty alkyl sulfates and fatty alkyl polyalkylene glycol ether sulfates which are generally referred to in short as alkyl sulfates or ether sulfates, can be obtained by sulfating fatty alcohols or by sulfating adducts of ethylene oxide and / or propylene oxide with fatty alcohols and then neutralizing the sulfuric acid semiesters formed with suitable bases, e.g. Soda lye, accessible.
- suitable sulfating agents are e.g. Sulfuric acid, oleum, sulfamic acid, but especially chlorosulfonic acid or gaseous sulfur trioxide into consideration [J.Am.Oil.Che. Soc. 36 (1959) 208-210].
- the starting materials for the preparation of the compounds according to the invention are known substances which can be obtained by customary methods in organic chemistry.
- isostearyl alcohol Cosm.Perf. 89.7 (1974) 45-47 and soap-oil-fat waxes 114.7 (1988) 231-233] are appropriately used Isostearic acid, which in turn is obtained from the cis monomer fraction of the dimerization, for example of tall oil fatty acid, after hardening and separation of the network.
- Example 2 Sulfation of isostearyl alcohol-2E0.
- isostearyl sulfates or isostearyl ether sulfates according to the invention have better wetting properties than the comparative examples.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Cosmetics (AREA)
Abstract
On obtient des alkylsulfates ou des éthersulfates à bonnes propriétés d'écoulement et de mouillabilité en sulfatant des isostéarylalcools ou des isostéarylpolyalkylène-glycoléthers puis en les neutralisant avec des bases appropriées.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3918252 | 1989-06-05 | ||
| DE3918252A DE3918252A1 (de) | 1989-06-05 | 1989-06-05 | Fettalkylsulfate und fettalkyl-polyalkylenglycolethersulfate, verfahren zu ihrer herstellung und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0475967A1 true EP0475967A1 (fr) | 1992-03-25 |
Family
ID=6382071
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90110111A Withdrawn EP0401642A1 (fr) | 1989-06-05 | 1990-05-28 | Sulfates d'alkyle gras et sulfates d'éthers alkyliques gras du polyalkylène glycol, procédé pour leur préparation et leur utilisation |
| EP90908223A Withdrawn EP0475967A1 (fr) | 1989-06-05 | 1990-05-28 | Alkylsulfates gras et alkylpolyalkylene-glycolethersulfates gras; leur procede de production et leur utilisation |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90110111A Withdrawn EP0401642A1 (fr) | 1989-06-05 | 1990-05-28 | Sulfates d'alkyle gras et sulfates d'éthers alkyliques gras du polyalkylène glycol, procédé pour leur préparation et leur utilisation |
Country Status (5)
| Country | Link |
|---|---|
| EP (2) | EP0401642A1 (fr) |
| JP (1) | JPH04505916A (fr) |
| DE (1) | DE3918252A1 (fr) |
| PT (1) | PT94260A (fr) |
| WO (1) | WO1990015049A1 (fr) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4109250A1 (de) * | 1991-03-21 | 1992-09-24 | Henkel Kgaa | Verfahren zur herstellung von hochkonzentrierten fettalkoholsulfat-pasten |
| DE4114243A1 (de) * | 1991-05-02 | 1992-11-05 | Henkel Kgaa | Verfahren zur herstellung von glycerinethersulfaten |
| DE4218075A1 (de) * | 1992-06-01 | 1993-12-02 | Henkel Kgaa | Verfahren zur Herstellung geruchsarmer Fettalkoholethersulfat-Salze |
| EP0609574B1 (fr) * | 1993-02-04 | 1997-06-18 | The Procter & Gamble Company | Solutions de sulfate d'alkyle hautement concentrées |
| DE4322968A1 (de) * | 1993-07-09 | 1995-01-12 | Henkel Kgaa | Verfahren zur Herstellung von Alkylsulfaten |
| GB9410678D0 (en) * | 1994-05-27 | 1994-07-13 | Unilever Plc | Surfactant composition and cleaning composition comprising the same |
| DE19503061A1 (de) * | 1995-02-01 | 1996-08-08 | Henkel Kgaa | Dimeralkohol-bis- und Trimeralkohol-tris-sulfate und -ethersulfate |
| DE19540295A1 (de) * | 1995-10-28 | 1997-04-30 | Henkel Kgaa | Verfahren zur Herstellung kurzkettiger Alkylsulfate |
| EG21623A (en) * | 1996-04-16 | 2001-12-31 | Procter & Gamble | Mid-chain branced surfactants |
| PH11997056158B1 (en) * | 1996-04-16 | 2001-10-15 | Procter & Gamble | Mid-chain branched primary alkyl sulphates as surfactants |
| EG21174A (en) * | 1996-04-16 | 2000-12-31 | Procter & Gamble | Surfactant manufacture |
| JP3043434B2 (ja) * | 1996-04-16 | 2000-05-22 | ザ、プロクター、エンド、ギャンブル、カンパニー | 長鎖の枝分れしたアルカノールおよびアルコキシル化アルカノールの硫酸塩の製造方法 |
| EG22088A (en) * | 1996-04-16 | 2002-07-31 | Procter & Gamble | Alkoxylated sulfates |
| JP4509223B2 (ja) * | 1996-04-16 | 2010-07-21 | ザ、プロクター、エンド、ギャンブル、カンパニー | 選択された中間鎖分岐界面活性剤を含有する洗剤組成物 |
| WO1997039089A1 (fr) * | 1996-04-16 | 1997-10-23 | The Procter & Gamble Company | Compositions liquides nettoyantes contenant des tensioactifs ramifies en milieu de chaine selectionnes |
| MA24137A1 (fr) * | 1996-04-16 | 1997-12-31 | Procter & Gamble | Fabrication d'agents de surface ramifies . |
| US6150322A (en) | 1998-08-12 | 2000-11-21 | Shell Oil Company | Highly branched primary alcohol compositions and biodegradable detergents made therefrom |
| US6093856A (en) * | 1996-11-26 | 2000-07-25 | The Procter & Gamble Company | Polyoxyalkylene surfactants |
| DE19714043C2 (de) * | 1997-04-05 | 2002-09-26 | Cognis Deutschland Gmbh | Verwendung von Glycerinsulfaten als Viskositätsregulatoren für konzentrierte wäßrige Alkyl(ether)sulfatpasten |
| ZA989155B (en) | 1997-10-10 | 1999-04-12 | Procter & Gamble | Mixed surfactant system |
| CN1281500A (zh) | 1997-10-14 | 2001-01-24 | 普罗格特-甘布尔公司 | 含有中链支链表面活性剂的轻垢液体或凝胶餐具洗涤剂组合物 |
| JP2001519376A (ja) | 1997-10-14 | 2001-10-23 | ザ、プロクター、エンド、ギャンブル、カンパニー | 中間鎖分岐界面活性剤を含んでなるパーソナルクレンジング組成物 |
| WO1999019435A1 (fr) | 1997-10-14 | 1999-04-22 | The Procter & Gamble Company | Compositions detergentes granuleuses comprenant des tensioactifs ramifies en milieu de chaine |
| DE19929511C2 (de) * | 1999-06-29 | 2003-04-10 | Cognis Deutschland Gmbh | Hochkonzentriert fließfähige Aniontensidmischungen |
| DE102007032670A1 (de) * | 2007-07-13 | 2009-01-15 | Clariant International Ltd. | Wässrige Zusammensetzungen enthaltend Alkylpolyethylenglykolethersulfate |
| US20130023687A1 (en) * | 2010-03-04 | 2013-01-24 | Hirosaki University | Surfactant for stabilizing water/supercritical carbon dioxide microemulsion |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2654772A (en) * | 1950-05-06 | 1953-10-06 | Du Pont | 2-(1, 3, 3-trimethylbutyl)-5, 7, 7-trimethyl octanol-1-sulfate |
| US2644831A (en) * | 1951-04-16 | 1953-07-07 | Monsanto Chemicals | Alkali metal and ammonium sulfates of hydroxy ethers |
| US3338949A (en) * | 1962-11-13 | 1967-08-29 | Eastman Kodak Co | 2, 2-dimethylalkyl sulfates and salts thereof |
| US3376333A (en) * | 1964-11-16 | 1968-04-02 | Textilana Corp | Sulfuric acid esters of linear secondary alcohol ethoxylates and salts thereof and method of producing same |
| GB1159112A (en) * | 1966-01-12 | 1969-07-23 | Ici Ltd | Process for the Production of Synthetic Detergents |
| US3647851A (en) * | 1967-06-29 | 1972-03-07 | Chevron Res | Secondary alcohol sulfation process in the presence of inorganic salts |
| GB1345533A (en) * | 1970-06-04 | 1974-01-30 | Agfa Gevaert | Coating compositions for photographic materials |
| GB1445997A (en) * | 1973-11-06 | 1976-08-11 | Unilever Ltd | Process for sulphating ethoxylated secondary alcohols |
| EP0024711B2 (fr) * | 1979-09-01 | 1989-02-08 | Henkel Kommanditgesellschaft auf Aktien | Produits concentrés de tensides aqueux et procédé pour l'amélioration des propriétés d'écoulement de produits concentrés de tensides aqueux difficilement transportables |
-
1989
- 1989-06-05 DE DE3918252A patent/DE3918252A1/de not_active Withdrawn
-
1990
- 1990-05-28 EP EP90110111A patent/EP0401642A1/fr not_active Withdrawn
- 1990-05-28 JP JP2507708A patent/JPH04505916A/ja active Pending
- 1990-05-28 EP EP90908223A patent/EP0475967A1/fr not_active Withdrawn
- 1990-05-28 WO PCT/EP1990/000850 patent/WO1990015049A1/fr not_active Ceased
- 1990-06-04 PT PT94260A patent/PT94260A/pt not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9015049A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0401642A1 (fr) | 1990-12-12 |
| DE3918252A1 (de) | 1990-12-13 |
| PT94260A (pt) | 1991-02-08 |
| JPH04505916A (ja) | 1992-10-15 |
| WO1990015049A1 (fr) | 1990-12-13 |
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