DE1443250A1 - Process for the preparation of water-soluble, solvent-free liquid salts of acidic, surface-active alkylsulfuric acid or alkylphosphoric acid esters or of alkyl or alkylarylsulfonic acid - Google Patents
Process for the preparation of water-soluble, solvent-free liquid salts of acidic, surface-active alkylsulfuric acid or alkylphosphoric acid esters or of alkyl or alkylarylsulfonic acidInfo
- Publication number
- DE1443250A1 DE1443250A1 DE19611443250 DE1443250A DE1443250A1 DE 1443250 A1 DE1443250 A1 DE 1443250A1 DE 19611443250 DE19611443250 DE 19611443250 DE 1443250 A DE1443250 A DE 1443250A DE 1443250 A1 DE1443250 A1 DE 1443250A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- alkyl
- acidic
- water
- soluble
- 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.)
- Pending
Links
- 239000002253 acid Substances 0.000 title claims description 17
- 150000003839 salts Chemical class 0.000 title claims description 17
- 230000002378 acidificating effect Effects 0.000 title claims description 15
- 239000007788 liquid Substances 0.000 title claims description 14
- 150000002148 esters Chemical class 0.000 title claims description 8
- 125000000217 alkyl group Chemical group 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- -1 glycol group Aliphatic amines Chemical class 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 8
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- 150000002191 fatty alcohols Chemical class 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 4
- 244000060011 Cocos nucifera Species 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 108010051210 beta-Fructofuranosidase Proteins 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 229940021013 electrolyte solution Drugs 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000011073 invertase Nutrition 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- OMEMQVZNTDHENJ-UHFFFAOYSA-N n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCNC OMEMQVZNTDHENJ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- FODHIQQNHOPUKH-UHFFFAOYSA-N tetrapropylene-benzenesulfonic acid Chemical compound CC1CC11C2=C3S(=O)(=O)OC(C)CC3=C3C(C)CC3=C2C1C FODHIQQNHOPUKH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile 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
- A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
-
- 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
- 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
- A61K8/55—Phosphorus compounds
- A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
-
- 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
-
- 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
- C11D1/143—Sulfonic acid esters
-
- 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
- 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
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Detergent Compositions (AREA)
Description
"Verfahren zur Herstellung wasserlöslicher, lösungsmittelfreier flüssiger Salze von sauren oberflächenaktiven Alkylschwefelsäure- oder Alkylphosphorsäureestern oder von Alkyl- oder Alkylarylsulfonsäuren" ' Die in der Praxis gebräuchlichen Salze, insbesondere Alkalisalze von sauren Einwirkungsprodukten von Mineralsäuren auf höhermolekulare organische Verbindungen, also z,B. die Alkalisalze von sauren höhermolekularen Alkylsulfaten, fallen, wenn man sie technisch in hochkonzentrierter bzw. wasserfreier Form herstellt, in fester, mehr oder weniger kristallisierter oder in festpastöser Form an. Da seit langem praktisches Interesse an der Verwendung von anionaktiven, hochkonzentrierten bzw. wasserfreien flüssigen Mitteln dieser Art besteht, hat man den Ausweg gewählt, diese Stoffe mit Hilfe von Lösungsmitteln, wie Alkoholen; Glykolen usw., in eine klarflüssige Form überzuführen."Process for the preparation of water-soluble, solvent-free liquids Salts of acidic surface-active alkylsulfuric acid or alkylphosphoric acid esters or of alkyl or alkylarylsulfonic acids "'The salts commonly used in practice, in particular alkali salts of acidic products of the action of mineral acids on higher molecular ones organic compounds, e.g. the alkali salts of acidic, higher molecular weight alkyl sulfates, fall if they are technically produced in a highly concentrated or anhydrous form, in solid, more or less crystallized or in solid pasty form. Since long practical interest in the use of anion-active, highly concentrated or anhydrous liquid means of this type, one has chosen the way out, these substances with the help of solvents such as alcohols; Glycols, etc., into one transferring clear liquid form.
Es wurde nun gefunden, daß man wasserlösliche, losungsmittelfreie flüssige Salze von sauren oberflächenaktiven Alkylschwefelsäure- oder Alkylphosphorsäureestern oder von Alkyl- oder Alkylarylsulfonsäuren dadurch herstellen kann, daß man diese in an sich bekannter Weise mit wenigstens eine Die oder Polyalkylenglykolgruppen im Molekül enthaltenden aliphatischen Aminen, die durch Anlagerung eines oder mehrerer Alkylenoxide an primäre, sekundäre. oder hydroxylsubstituierte tertiäre Amine erhalten worden sind, neutralisiert.It has now been found that water-soluble, solvent-free liquid salts of acidic surface-active alkylsulfuric acid or alkylphosphoric acid esters or of alkyl or alkylarylsulfonic acids can be prepared by these in a manner known per se with at least one die or polyalkylene glycol group Aliphatic amines contained in the molecule, which are formed by the addition of a or several alkylene oxides to primary, secondary. or hydroxyl-substituted tertiary Amines obtained are neutralized.
Diese Salze besitzen praktische Bedeutung für die Herstellung von Körperpflegemitteln, insbesondere für die Haarwäsche und für Badeschaumpräparate. Sie sind aber auch auf anderen, bekannten Anwendungsgebieten für anionaktive Stoffe verwendbar, weil sie leicht wasserlöslich sind und ohne Shwierigkeiten wäßrige Lösungen auch höherer Konzentration ergeben. Die Salze zeichnen sich ferner durch besonders geringe Salzempfindlichkeit aus, so daß sie mit besonderem Vorteil in Verbindung mit wäßrigen Elektrolytlösungen angewendet werden können.These salts are of practical importance for the production of Body care products, in particular for hair washing and for bath foam preparations. But they are also in other, known areas of application for anionic substances can be used because they are easily soluble in water and aqueous solutions without difficulty also result in higher concentration. The salts are also characterized by special low salt sensitivity, so that they are associated with particular advantage can be used with aqueous electrolyte solutions.
Weiterhin erwiesen sie sich~im Fermenttest, z.Bi mit Saccharase, erheblich weniger schädigend als entsppechende Salze aus nicht alkoxylierten Amiden. Erfahrungsgemäß kann hieraus geschlossen wereden, daß die erfindungsgemäßen Salae hautverträglicher sind als die üblichen Aminsalze.Furthermore, they proved to be considerable in the ferment test, e.g. with saccharase less damaging than corresponding salts from non-alkoxylated amides. According to experience it can be concluded from this that the Salae according to the invention are more skin-friendly are than the usual amine salts.
Die genannten sauren Alkylschwefelsäure- oder Alkylphosphorsäureester bzw. Alkyl- oder Alkylarylsulfonsäuren leiten sich in bekannter Weise von aliphatischen oder aliphatisch-aromatischen Verbindungen mit 8 - 18, vorzugsweise 12 - 18 Kohlenstoffatomen ab. Als Beispiele für diese Verbindungen sind zu nennen die sauren Schwefelsäureester des Dodecylalkohols, des Octadecylalkohols von Kokosfettalkoholgemischen der Kettenlängeh C12 - C14 sowie deren Glykoläther und dergl-eichen, ferner saure Alkylsulfonsäuren mit Alkylresten von C10 - C18, Alkyl- -benzol - oder -naphthalin-sulfosäuren mit Alkylresten C3 - XZ8 saure Mono- und Dialkylphosphorsäureester und dergleichen.The acidic alkylsulfuric acid or alkylphosphoric acid esters mentioned or alkyl or alkylarylsulfonic acids are derived in a known manner from aliphatic or aliphatic-aromatic compounds with 8-18, preferably 12-18 carbon atoms away. Examples of these compounds are the acidic sulfuric acid esters of dodecyl alcohol, of octadecyl alcohol of coconut fatty alcohol mixtures of chain length h C12 - C14 and their glycol ethers and the like, furthermore acidic alkyl sulfonic acids with alkyl radicals from C10 - C18, alkyl benzene - or -naphthalene sulfonic acids with alkyl radicals C3-XZ8 acidic mono- and dialkyl phosphoric acid esters and the like.
Den als Neutralisationsmittel verwendeten alkoxylierten Aminen liegen vorwiegend niedermolekulare, primäre oder sekundare aliphatische Amine zugrunde, die auch Substituenten, insbesondere Hydroxylsubstituenten besitzen können, oder vorwiegend niedermolekulare tertiäre Amine, die Hydroxylsubstituenten aufweisen. Man kann Jedoch als Neutralisationsmittel auch höhermolekulare Alkylamine verwenden, die zur Anlagerung von Alkylenoxidresten befähigt sind.The alkoxylated amines used as neutralizing agents are predominantly low molecular weight, primary or secondary aliphatic amines, which can also have substituents, in particular hydroxyl substituents, or predominantly low molecular weight tertiary amines which have hydroxyl substituents. However, higher molecular weight alkylamines can also be used as neutralizing agents, which are capable of the addition of alkylene oxide residues.
Als Amine sind demgemäß zu nennen Triäthanolamin, Dialkylmonoäthanolamine, Alkyldiäthanolamine oder auch höhermolekulare Amine, wie beispielsweise Hexylamin, Dioctylamin, Dodecylamin, N-Methyldodecylamin, Cyclohexylamin und dergleichen. An diese Amine werden zur Herstellung der erfindungsgemäß als Neutralieationsmittel verwendeten Alkoxylierungsprodukte relativ geringe Mengen von 1 - 12 Mol, vorzugsweise 3 - 6 Mol Alkylenoxid, wie z.B, Athylenoxid in üblicher Weise angelagert. Als Anlagerungsprodukte dieser Art sind z.B. zu nennen das Anlagerungsprodukt von 3 - 6 Mol Athylenoxid an Triäthanolamin, Diäthylaminoäthanol, Butylamin, Dodecylamin und dergleichen. Bei der Anlagerung entstehen in der Regel Mischprodukte, die auch geringe Anteile an Polyglykolen enthalten können.As amines, triethanolamine, dialkylmonoethanolamine, Alkyl diethanolamines or even higher molecular weight amines, such as hexylamine, Dioctylamine, dodecylamine, N-methyldodecylamine, cyclohexylamine and the like. At these amines are used as neutralizing agents for the production of the invention alkoxylation products used relatively small amounts of 1 to 12 mol, preferably 3 - 6 moles of alkylene oxide, such as ethylene oxide, added in the usual way. As addition products of this type are, for example, the addition product of 3 - 6 moles of ethylene oxide of triethanolamine, diethylaminoethanol, butylamine, dodecylamine and the like. During the accumulation, mixed products, which also contain small proportions, are usually formed may contain polyglycols.
Die Neutralisation der vorgenannten sauren oberflächenaktiven Verbindungen mit den obigen Aminbasen erfolgt in üblicher Weise, Man erhält entsprechende Salze, die sich dadurch auszeichnen, daß sie im wasserfreien, hochkonzentrierten-Zustand klar und flüssig sind, sich ohne Schwierigkeiten mit Wasser verdünnen lassen; und klare, wäßrige Lösungen verschiedener Viskosität ergeben, die im hohen Maße salzbeständig sind.The neutralization of the aforementioned acidic surface-active compounds with the above amine bases is carried out in the usual way, corresponding salts are obtained, the are characterized by the fact that they are in the anhydrous, highly concentrated state are clear and fluid and can be diluted with water without difficulty; and Clear, aqueous solutions of different viscosities result which are salt-resistant to a high degree are.
Man kann die erhaltenen Salze auch mit anderen anionaktiven oder nichtionogenen oberflächenaktiven Stoffen und/oder mit bekannten Zusätzen -zu derartigen Stoffen, also z.B. bekannten Waschhilfsmitteln' kombinieren.The salts obtained can also be mixed with other anionic or nonionic surface-active substances and / or with known additives -to such substances, e.g. combine known washing aids'.
Als Beispiele hierfür sind vor allem Athylenoxidanlagerungsprodukte an höhermolekulare Verbindungen mit austauschbaren. Wasserstoffatomen und Fettsäurealkanolamide zu- nennen.. Bekannte Waschhilfsmittel sind z. B. Alkalicarbonat,e -sulfate, -silikate,-phosphate, -borate, Methylcellulose, Salze von Celluloseäthercarbonsäuren und dergleichen.Examples of this are primarily ethylene oxide addition products of higher molecular weight compounds with interchangeable. Hydrogen atoms and fatty acid alkanolamides to name .. Known washing aids are z. B. alkali carbonate, e-sulfates, -silicates, -phosphates, borates, methyl cellulose, salts of cellulose ether carboxylic acids and the like.
Die erfindungsgemäßen Salze sind auch mit Vorteil in der Textil-, Leder- und Papierhilfsmittelindustrie verwendbar, ferner in der Lack- und Kunststoffindustrie, sowie als Spül-, Wasser und Reinigungsmittel aller Art.The salts according to the invention are also advantageous in textile, Leather and paper auxiliary industry can be used, furthermore in the paint and plastics industry, as well as washing up liquid, water and cleaning agents of all kinds.
Beispiele 1.) In der nachstehenden Tabelle sind Ausgangsstoffe und Mengenanteile für die Herstellung von Salzen aus äthoxylierten Aminen und Alkylsulfaten bzw. Alkyläthersulfaten angegeben, aus denen sich nach der erfindungsgemäßen Arbeitsweise flüssige Salze herstellen lassen.Examples 1.) In the table below are starting materials and Quantities for the production of salts from ethoxylated amines and alkyl sulfates or alkyl ether sulfates indicated, from which, according to the procedure according to the invention Let make liquid salts.
Ausgangsstoffe in g
.2.) 4o g technische Tetrapropylenbenzolsulfosäure läßt man unter Kühlung langsam zu etwa 44 g des Anlagerungsproduktes von 3 Mol Äthylenoxid an 1 Mol TRiäthanolamin zulaufen, bis ein pH-Wert von etwa 6,5 - 7,0 erreicht ist. Man erhält eine klare, viskose Flüssigkeit, die klar wasserlöslich ist..2.) 4o g of technical grade tetrapropylenebenzenesulfonic acid is left under Slow cooling to about 44 g of the adduct of 3 moles of ethylene oxide and 1 Add moles of diethanolamine until a pH of about 6.5 - 7.0 is reached. Man receives a clear, viscous liquid that is clearly soluble in water.
3.) Auf 41 g eines Fettalkoholgemisches C12 C C18 läßt man 13 g Phosphorpentoxid einwirken und erhält einen sauren Ester, den man mit 94 g des Anlagerunsproduktes von.3.) 13 g of phosphorus pentoxide are left on 41 g of a C12 C C18 fatty alcohol mixture act and obtain an acidic ester, which is mixed with 94 g of the additive product from.
6 Mol Äthylenoxid an 1 Mol Triäthanolamin bis zu einem pH-Wert von 6,5 - 7,o neutralisiert. Das so gewonnene Salz des Fettalkoholphosphats ist ein flüssiges, klares, schwach gelb gefärbtes Produkt. 6 moles of ethylene oxide on 1 mole of triethanolamine up to a pH of 6.5 - 7, o neutralized. The salt of the fatty alcohol phosphate obtained in this way is a liquid, clear, slightly yellow colored product.
4.) Das Anlagerungsprodukt von 3 Mol Äthylenoxid an ein Bettalkoholgemisch der Kettenlängen C12 - C14 wird im Molverhältnis 1 : 1 mit Chlorsulfonsäure in üblicher Weise umgesetzt. Der entstehende saure Ester wird mit einem Anlagerungsprodukt von-5 Mol Äthylenoxid an Triäthanolamin bis zu einem pH-Wert von 7,o neutralisiert. Es entsteht ein klares, flüssiges Produkt, das in Wasser vollkommen klar löslich ist.4.) The adduct of 3 moles of ethylene oxide onto a bed alcohol mixture the chain lengths C12 - C14 in a molar ratio of 1: 1 with chlorosulfonic acid in the usual way Wise implemented. The acidic ester formed is treated with an adduct of -5 Moles of ethylene oxide in triethanolamine up to a pH of 7, o neutralized. It the result is a clear, liquid product that is completely soluble in water.
Die ausgezeichnet schäumenden wäßrigen Lösungen zeigen gegenüber Wasserstoffperoxid eine bemerkenswerte Stabilisierwirkung. So betrug die Abnahme der Sauerstoffaktivität einer 19,5 % H2O2 sowie 10,5 % des vorgenannten Produktes enthaltenden wäßrigen Lösung innerhalb von 12 Wochen bei 350 und schwachsauren pH-Werten (ca. 6 - 7) nur 19. The excellent foaming aqueous solutions show opposite Hydrogen peroxide has a remarkable stabilizing effect. So the decrease was the oxygen activity of 19.5% H2O2 and 10.5% of the aforementioned product containing aqueous solution within 12 weeks at 350 and weakly acidic pH values (approx. 6 - 7) only 19.
5.) 50 g Mersolsäure wurden mit 38 g eines Umsetzungsproduktes von Äthylendiamin mit 4 Mol Athylenoxid neutralisiert. Es wurde ein flüssiges, honigartig aussehendes Produkt erhalten, das in wäßriger Lösung ausgezeichnete Schaumeigenschaften besitzt und ebenfalls gegen Wasserstoffperoxid stabilisierend wirkt.5.) 50 g of mersolic acid were with 38 g of a reaction product of Ethylenediamine neutralized with 4 moles of ethylene oxide. It became a liquid, honey-like looking product obtained, which in aqueous solution excellent foam properties and also has a stabilizing effect against hydrogen peroxide.
6.) loo g Dodecylbenzolsulfonsäure werden mit 83 g eines Einwirkungsproduktes von 1 Mol Athylenoxid und 1 Mol Propylenoxid auf Diäthylaminoäthanol bis zum pH von 7 neutralisiert. Man.erhält 183 g eines flüssigen, wasserfreien Reinigungsmittels, das auch nach dem Abkühlen auf 50 flüssig bleibt.6.) 100 g of dodecylbenzenesulfonic acid are mixed with 83 g of an action product of 1 mole of ethylene oxide and 1 mole of propylene oxide on diethylaminoethanol to pH neutralized by 7. You get 183 g of a liquid, water-free cleaning agent, which remains liquid even after cooling to 50.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0036644 | 1961-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1443250A1 true DE1443250A1 (en) | 1971-11-25 |
Family
ID=7043212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19611443250 Pending DE1443250A1 (en) | 1961-07-24 | 1961-07-24 | Process for the preparation of water-soluble, solvent-free liquid salts of acidic, surface-active alkylsulfuric acid or alkylphosphoric acid esters or of alkyl or alkylarylsulfonic acid |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE620530A (en) |
| CH (1) | CH418326A (en) |
| DE (1) | DE1443250A1 (en) |
| NL (1) | NL281270A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2538279A1 (en) * | 1975-08-28 | 1977-03-10 | Zschimmer & Schwarz Chemische | Dubbing leather and pelts - with materials prepd. by sulphonating alkyl aromatic cpds. and neutralising or hydrolysing prod. |
| DE4443643A1 (en) * | 1994-12-08 | 1996-06-13 | Henkel Kgaa | Prepn. of anionic glucamide detergents without strong oxidn. of sugar components |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2121325C2 (en) * | 1971-04-30 | 1982-11-11 | Basf Ag, 6700 Ludwigshafen | Process for the preparation of methoxypropionitrile |
-
0
- BE BE620530D patent/BE620530A/fr unknown
- NL NL281270D patent/NL281270A/xx unknown
-
1961
- 1961-07-24 DE DE19611443250 patent/DE1443250A1/en active Pending
-
1962
- 1962-05-10 CH CH562762A patent/CH418326A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2538279A1 (en) * | 1975-08-28 | 1977-03-10 | Zschimmer & Schwarz Chemische | Dubbing leather and pelts - with materials prepd. by sulphonating alkyl aromatic cpds. and neutralising or hydrolysing prod. |
| DE4443643A1 (en) * | 1994-12-08 | 1996-06-13 | Henkel Kgaa | Prepn. of anionic glucamide detergents without strong oxidn. of sugar components |
Also Published As
| Publication number | Publication date |
|---|---|
| CH418326A (en) | 1966-08-15 |
| BE620530A (en) | |
| NL281270A (en) |
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