US1968793A - Sulphuric ester of higher alcohols - Google Patents
Sulphuric ester of higher alcohols Download PDFInfo
- Publication number
- US1968793A US1968793A US350135A US35013529A US1968793A US 1968793 A US1968793 A US 1968793A US 350135 A US350135 A US 350135A US 35013529 A US35013529 A US 35013529A US 1968793 A US1968793 A US 1968793A
- Authority
- US
- United States
- Prior art keywords
- sulphuric
- ester
- acid
- sulphuric ester
- higher alcohols
- 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.)
- Expired - Lifetime
Links
- 150000002148 esters Chemical class 0.000 title description 14
- 150000001298 alcohols Chemical class 0.000 title description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- 239000001117 sulphuric acid Substances 0.000 description 6
- 235000011149 sulphuric acid Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000009736 wetting Methods 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- -1 fatty acid esters Chemical class 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000182067 Fraxinus ornus Species 0.000 description 1
- 235000002917 Fraxinus ornus Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000003925 fat Substances 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D1/00—Fire-extinguishing compositions; Use of chemical substances in extinguishing fires
- A62D1/0071—Foams
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B26—HAND CUTTING TOOLS; CUTTING; SEVERING
- B26D—CUTTING; DETAILS COMMON TO MACHINES FOR PERFORATING, PUNCHING, CUTTING-OUT, STAMPING-OUT OR SEVERING
- B26D7/00—Details of apparatus for cutting, cutting-out, stamping-out, punching, perforating, or severing by means other than cutting
- B26D7/06—Arrangements for feeding or delivering work of other than sheet, web, or filamentary form
-
- 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
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
Definitions
- the sulphuric ester of hydroxystearic acid may be produced from oleic acid or by treatment with sulphuric acid the sulphuric ester of a di-hydroxysteario acid may be obtained from ricinoleic acid, and so forth.
- Oils heretofore treated with sulphuric acid to produce these agents include castor oil, cottonseed oil, arachis oil, and olive oil.
- estersi have a low resistance to lime, which is very deleterious in the textile industry, this objectionable property being ascribed in great part to the fact that the saturation of the carboxyl group may result in salts which are diflicultly soluble.
- corresponding alcohols more specifically, higher unsaturated normal-primary alcohols are subjected to the sulphation, that is the corresponding alcohols are esterifled with for example, sulphuric acid.
- sulphuric acid for instance oleyl alcohol is ⁇ converted to its sulphuric ester.
- stearyl alcohol may be esterified directly with sulfuric acid.
- the esteriflcation may, for example, be effected with concentrated or fuming sulphuric acid or other sulphonating agents which have strongly water-binding properties as for instance chlorosulphonic acid in the cold, that is at temperatures round about 0 C.
- the resultant sulphuric esters are readily soluble in water and are strongly wetting and foaming substances which may be employed for manifoldtextile purposes. Since they contain no carboxyl groups they are not precipitated by the hardness-forming constituents in the water and are thus far superior in their properties to the ordinary sulphuric esters of the fats and fatty acids.
- the reaction may be, illustrated by 55 the following sulphation procedure:
- a wetting, cleaning,.foaming and dispersing agent of the class described comprising a sulphuric ester of a higher unsaturated normal-primary alcohol.
- a compound for use in the treatment of flbrous materials comprising a sulphuric ester of a higher unsaturated normal primary alcohol corresponding in number of carbon atoms with the fatty acid radicals of the fatty acids and fatty acid esters heretofore employed in the form of 10 their sulphuric derivatives as wetting, cleaning and impregnating agents in the textile industry.
- a wetting, cleaning. foaming and dispersing agent comprising a sulphuric ester of a higher unsaturated normal primary alcohol in which the 35 alcohol is ester-flied both at the double bond and at the end of the chain.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Forests & Forestry (AREA)
- Business, Economics & Management (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Emergency Management (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
Description
Patented July 31, 1934 1,968,793 smnumo ns'rnn or manna ALOOHOLS Heinrich Bertsch, Chemnitz, Germany, assignor, by vJnesne assignments, to American Hyalsol Corporation, Wilmington, Del., a corporation of Delaware No Drawing. Application March 26, 1929, Serial No. 350,135. Renewed December 28, 1932. In Germany March 30, 1928 9 Claims. (01. 260-9542) This invention is concerned with the produc- CH3.(CH2) CH=CH.(CH,),CH20H+2H S tion of substances which may be used in the textile, leather and allied industries as wetting, cleaning, dispersing and like agents.
Water soluble sulphuric esters produced by converting fatty acids or esters of fatty acids, particularly such as contain either a double linkage or a hydroxyl group, into said'sulphuricesters, V
are widely employed as wetting, cleaning and impregnating agents in the textile industry. Thus by the addition of sulphuric acid, the sulphuric ester of hydroxystearic acid may be produced from oleic acid or by treatment with sulphuric acid the sulphuric ester of a di-hydroxysteario acid may be obtained from ricinoleic acid, and so forth. Oils heretofore treated with sulphuric acid to produce these agents include castor oil, cottonseed oil, arachis oil, and olive oil. All these substances are attended by the defect that they contain a carboxyl group which is free or combined with an alkali metal, and as a result they are capable, by reactionat the carboxyl group, of forming salts which, as in particular in the. case of alkaline earth salts, are water insoluble.
Consequently these aforementioned estersihave a low resistance to lime, which is very deleterious in the textile industry, this objectionable property being ascribed in great part to the fact that the saturation of the carboxyl group may result in salts which are diflicultly soluble.
This defect is avoided if, in accordance with the present invention, instead of the fatty acids or fatty acid esters, corresponding alcohols more specifically, higher unsaturated normal-primary alcohols are subjected to the sulphation, that is the corresponding alcohols are esterifled with for example, sulphuric acid. For instance oleyl alcohol is\converted to its sulphuric ester. Similarly stearyl alcohol may be esterified directly with sulfuric acid.
The esteriflcation may, for example, be effected with concentrated or fuming sulphuric acid or other sulphonating agents which have strongly water-binding properties as for instance chlorosulphonic acid in the cold, that is at temperatures round about 0 C. The resultant sulphuric esters are readily soluble in water and are strongly wetting and foaming substances which may be employed for manifoldtextile purposes. Since they contain no carboxyl groups they are not precipitated by the hardness-forming constituents in the water and are thus far superior in their properties to the ordinary sulphuric esters of the fats and fatty acids. The reaction may be, illustrated by 55 the following sulphation procedure:
sulphuric ester of 1,9 octodecandiol.
I claim:-
1. The process of producing agents of the class described, consisting in converting higher unsaturated normal-primary alcohols into sulphuric acid esters by subjecting them to the action of a sulphating medium.
2. The process of producing agents of the class described, consisting in converting higher unsaturated normal-primary alcohols into sulphuric acid esters by subjecting them to the action of a sulphating medium in the cold. 7
3. The process of producing agents of the class described, consisting in converting higher unsaturated normal-primary alcohols into sulphuric acid esters by subjecting them to the action of a sulphating medium at a temperature of about 0 C.
4. The process of producing agents of the class described, consisting in converting higher unsaturated normal-primary alcohols into sulphuric acid esters by subjecting them to the action of a so sulphating medium having water binding proper; ties.
5. The process of producing the sulphuric ester of 1,9-octodecanediol for use as an agent of the kind described, consisting in esterifying oleyl alcohol by subjecting the same to the action of concentrated or fuming sulphuric acid at a temperature of about 0 C.
6. A wetting, cleaning,.foaming and dispersing agent of the class described comprising a sulphuric ester of a higher unsaturated normal-primary alcohol.
7. The compound comprising the sulphuric ester of oleyl alcohol.
8. A compound for use in the treatment of flbrous materials comprising a sulphuric ester of a higher unsaturated normal primary alcohol corresponding in number of carbon atoms with the fatty acid radicals of the fatty acids and fatty acid esters heretofore employed in the form of 10 their sulphuric derivatives as wetting, cleaning and impregnating agents in the textile industry.
9. A wetting, cleaning. foaming and dispersing agent comprising a sulphuric ester of a higher unsaturated normal primary alcohol in which the 35 alcohol is ester-flied both at the double bond and at the end of the chain.
HEINRICH BERTSCH.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB150315D DE659277C (en) | 1928-03-30 | 1928-03-30 | Dispersing, wetting, cleaning and penetrating agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1968793A true US1968793A (en) | 1934-07-31 |
Family
ID=7002162
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US350135A Expired - Lifetime US1968793A (en) | 1928-03-30 | 1929-03-26 | Sulphuric ester of higher alcohols |
| US650203A Expired - Lifetime US1968797A (en) | 1928-03-30 | 1933-01-04 | Sulphuric derivative of higher alcohols |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US650203A Expired - Lifetime US1968797A (en) | 1928-03-30 | 1933-01-04 | Sulphuric derivative of higher alcohols |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US1968793A (en) |
| DE (1) | DE659277C (en) |
| FR (1) | FR671456A (en) |
| GB (1) | GB308824A (en) |
| NL (1) | NL24700C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2619467A (en) * | 1952-11-25 | Detergent mixtures containing | ||
| US2666527A (en) * | 1945-06-22 | 1954-01-19 | Peterson Filters & Eng | Method of promoting filtration |
| US3959334A (en) * | 1969-01-10 | 1976-05-25 | Chevron Research Company | Lime soap dispersant compounds |
| US4000081A (en) * | 1969-01-10 | 1976-12-28 | Chevron Research Company | Lime soap dispersant compounds |
| US5037992A (en) * | 1989-12-18 | 1991-08-06 | The Procter & Gamble Company | Process for sulfating unsaturated alcohols |
| US6239093B1 (en) * | 1996-06-28 | 2001-05-29 | The Procter & Gamble Company | Liquid cleaning compositions and shampoos containing dianionic or alkoxylated dianionic surfactants |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2603606A (en) * | 1952-07-15 | Alkyl sulfates | ||
| DE763809C (en) * | 1933-07-21 | 1954-05-03 | Hydrierwerke A G Deutsche | Process for the manufacture of sulphonation products |
| DE763234C (en) * | 1935-06-09 | 1953-01-19 | Wacker Chemie Gmbh | Process for the production of sulfuric acid or phosphoric acid esters of higher molecular weight, monohydric, saturated, aliphatic, primary alcohols |
| GB391433A (en) * | 1939-07-24 | 1933-04-27 | Ig Farbenindustrie Ag | Improvements relating to the treatment of textile materials |
| US2489955A (en) * | 1943-08-25 | 1949-11-29 | Colgate Palmolive Peet Co | Preparation of nondusting organic detergent compositions |
| US2480579A (en) * | 1943-10-21 | 1949-08-30 | Colgate Palmolive Peet Co | Detergent products and their preparation |
| US2553716A (en) * | 1946-07-19 | 1951-05-22 | Rare Galen Inc | Mild detergent and method of making same |
| US2613218A (en) * | 1950-06-12 | 1952-10-07 | Purex Corp Ltd | Vacuum neutralization of detergents |
| US2819318A (en) * | 1953-12-02 | 1958-01-07 | Ethyl Corp | Alcohols derived from babassu oil |
| US3249550A (en) * | 1964-05-27 | 1966-05-03 | Dow Corning | Glass cleaning compositions |
| DE4322968A1 (en) * | 1993-07-09 | 1995-01-12 | Henkel Kgaa | Process for the preparation of alkyl sulfates |
| DE19503061A1 (en) * | 1995-02-01 | 1996-08-08 | Henkel Kgaa | Dimer alcohol bis- and trimer alcohol tris-sulfates and ether sulfates |
-
0
- GB GB308824D patent/GB308824A/en active Active
- NL NL24700D patent/NL24700C/xx active
-
1928
- 1928-03-30 DE DEB150315D patent/DE659277C/en not_active Expired
-
1929
- 1929-03-14 FR FR671456D patent/FR671456A/en not_active Expired
- 1929-03-26 US US350135A patent/US1968793A/en not_active Expired - Lifetime
-
1933
- 1933-01-04 US US650203A patent/US1968797A/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2619467A (en) * | 1952-11-25 | Detergent mixtures containing | ||
| US2666527A (en) * | 1945-06-22 | 1954-01-19 | Peterson Filters & Eng | Method of promoting filtration |
| US3959334A (en) * | 1969-01-10 | 1976-05-25 | Chevron Research Company | Lime soap dispersant compounds |
| US4000081A (en) * | 1969-01-10 | 1976-12-28 | Chevron Research Company | Lime soap dispersant compounds |
| US5037992A (en) * | 1989-12-18 | 1991-08-06 | The Procter & Gamble Company | Process for sulfating unsaturated alcohols |
| US6239093B1 (en) * | 1996-06-28 | 2001-05-29 | The Procter & Gamble Company | Liquid cleaning compositions and shampoos containing dianionic or alkoxylated dianionic surfactants |
Also Published As
| Publication number | Publication date |
|---|---|
| GB308824A (en) | |
| US1968797A (en) | 1934-07-31 |
| FR671456A (en) | 1929-12-18 |
| NL24700C (en) | |
| DE659277C (en) | 1938-04-29 |
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