CA1105485A - Mixture of sulfosuccinate halfester and process for the preparation thereof - Google Patents
Mixture of sulfosuccinate halfester and process for the preparation thereofInfo
- Publication number
- CA1105485A CA1105485A CA316,176A CA316176A CA1105485A CA 1105485 A CA1105485 A CA 1105485A CA 316176 A CA316176 A CA 316176A CA 1105485 A CA1105485 A CA 1105485A
- Authority
- CA
- Canada
- Prior art keywords
- sulfosuccinate
- mixture
- fatty
- halfesters
- jojoba oil
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 229940119170 jojoba wax Drugs 0.000 claims abstract description 20
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 16
- 229930195729 fatty acid Natural products 0.000 claims abstract description 16
- 239000000194 fatty acid Substances 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 239000003599 detergent Substances 0.000 claims abstract description 10
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 10
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- 150000001408 amides Chemical class 0.000 claims abstract description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 150000001414 amino alcohols Chemical class 0.000 claims abstract description 3
- 150000001768 cations Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 229930195733 hydrocarbon Natural products 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- -1 aliphatic hydrocarbon radical Chemical group 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 241000221095 Simmondsia Species 0.000 abstract description 4
- 235000004433 Simmondsia californica Nutrition 0.000 abstract description 4
- 239000002453 shampoo Substances 0.000 abstract description 2
- 239000004744 fabric Substances 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 239000004164 Wax ester Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 238000009736 wetting Methods 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
- C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE:
A mixture of sulfosuccinate halfesters based on jojoba oil, containing compounds having the general formulae:
and
A mixture of sulfosuccinate halfesters based on jojoba oil, containing compounds having the general formulae:
and
Description
This invention relates to a novel mixture of sulfo-succinate halfesters based on jojoba oil and to a process ~or the preparation thereof.
Mixtures of sulfosuccinate halfesters which are based on sperm oil or on spermaceti oil are described in German Auslegeschrift 2, 039,745. These sulfosuccinate halfesters have shown as detergents for many applications highly desirable properties, but in some areas their foarming capacity is undesirable high.
It is therefore an object of this invention to provide a novel mixture of sulfosuccinate halfesters with a lowe~ foaming capacity and a process for making such an halfester mixture.
It has now found that valuable mixtures of sulfosucci-nate halfesters may be prepared by using jojoba oil as one of the initial materials for preparing the sulfosuccinate halfesters.
According to the invention, a mixture of sulfosuccinate halfester is obtained by saponifying jojoba oil to fatty alcohol and to fatty acids, or transesterifying jojoba oil with a monovalent alcohol with from 1 to 3 carbon atoms to fatty alcohol and the corresponding fatty acid alkylester, converting the fatty acids or the fatty acid alkylesters in the presence of the fatty alcohol by reaction with an amino alcohol, such as monoethanolamine or isopropanolamine, to acyl alkanol amides, and reacting the mixture of fatty alcohol and acyl alkanol amides with maleic acid anhydride and sulfite to sulfosuccinate halfesters.
Jojoba oil is a wax ester which has,according to the publication of D. M. Yermanos and C.C. Duncan in J.A.O.C.S. 53, 80 (1976) which is based on research work done in the yearC
1973 and 1974,the following distribution of the chain length in the extreme data:
5~
Fatty acid Fatty alcohol distribution dis-tribution C 18 : 1 10.1 - 20.7 %
C 20 : 1 67.5 - 77.0 % 26.1. - 63.3 %
C 22 : 1 6.2 - 13.8 % 27.2. - ~2.0 %
C 24 : 1 1-0- - ~- %
The ~ovel mixture of the sulfosuccinate halfester according to the invention can be characterized as containing compounds of the following ~ormulae:
y y~ R" Y Y' R-O-CO-C~I-CH-COOM and R'-CO-~-X-0-C0-CH-CH-COOM
wherein R represents the hydrocarbon chains of the fatty alcohols of the jojoba oil, R'represents the hydrocarbon chains of the fatty acids of the jojoba oil, X is a straight or branched pr~ferably aliphatic hydrocarbon radical with at least 2 carbon atoms, preferably an alkyl radical with 2 or 3 carbon atoms, R'' is hydrogen, an alkyl group or a hydroylalkyl group, the total number of C atoms in X and R'' being from 2 to 6r M is an equivalent of a cation which is suitable for detergents and make the product water soluble, such as an alkali metal ion or an ammonium ion, Y is hydrogen and Y'is S03M or vice versa.
The following example and tests further illustrate the invention.
EXAMPLE
100 grams of jojoba oil are reacted with 10 grams of mon~ethanolamine in the presence of 0.1 gram of sodium methylate catalys-t or another well known saponification catalyst with stirring while raising the temperature slowly to 140 degree C, care being taken that some free alkali is available by adding some additional sodium methylate if required~ After a reaction period of 2 hours, a p~oduct is obtained wh.ich at room tempera-ture is a waxy solid and does not show any longer ester bandsin the IR-spectrum. The material is a mixture of the mono-ethanolamlde of jojoba fatty aaids and of jojoba fatty alcohol.
80 grams of this reaction mixture are reacted with 26 grams of maleic acid anhydride at a temperature of about 80 degree C for about 1 hour. The halfester mixture thus formed is then directly sulfonated by reaction with 34 grams sodium sulfite in 310 grams water by heating to about 80 degree C for 1/2 hour.
The reaction product obtained is a milk~ white disper-sion with a solid content of 30 percent by weight which after dilution with water forms anearly clear viscous liquid.
II1 the following tests,a mixture of sulfosuccinate halfesters according to the invention and based on jojoba oil (SB-J) is compared with a mixture of corresponding sul~o-succinate halfester of sperm oil.
1) Foaming capacity and foam stability according Roos Miles (0,1 % at 40 degree C, immediate and after 5 min~)
Mixtures of sulfosuccinate halfesters which are based on sperm oil or on spermaceti oil are described in German Auslegeschrift 2, 039,745. These sulfosuccinate halfesters have shown as detergents for many applications highly desirable properties, but in some areas their foarming capacity is undesirable high.
It is therefore an object of this invention to provide a novel mixture of sulfosuccinate halfesters with a lowe~ foaming capacity and a process for making such an halfester mixture.
It has now found that valuable mixtures of sulfosucci-nate halfesters may be prepared by using jojoba oil as one of the initial materials for preparing the sulfosuccinate halfesters.
According to the invention, a mixture of sulfosuccinate halfester is obtained by saponifying jojoba oil to fatty alcohol and to fatty acids, or transesterifying jojoba oil with a monovalent alcohol with from 1 to 3 carbon atoms to fatty alcohol and the corresponding fatty acid alkylester, converting the fatty acids or the fatty acid alkylesters in the presence of the fatty alcohol by reaction with an amino alcohol, such as monoethanolamine or isopropanolamine, to acyl alkanol amides, and reacting the mixture of fatty alcohol and acyl alkanol amides with maleic acid anhydride and sulfite to sulfosuccinate halfesters.
Jojoba oil is a wax ester which has,according to the publication of D. M. Yermanos and C.C. Duncan in J.A.O.C.S. 53, 80 (1976) which is based on research work done in the yearC
1973 and 1974,the following distribution of the chain length in the extreme data:
5~
Fatty acid Fatty alcohol distribution dis-tribution C 18 : 1 10.1 - 20.7 %
C 20 : 1 67.5 - 77.0 % 26.1. - 63.3 %
C 22 : 1 6.2 - 13.8 % 27.2. - ~2.0 %
C 24 : 1 1-0- - ~- %
The ~ovel mixture of the sulfosuccinate halfester according to the invention can be characterized as containing compounds of the following ~ormulae:
y y~ R" Y Y' R-O-CO-C~I-CH-COOM and R'-CO-~-X-0-C0-CH-CH-COOM
wherein R represents the hydrocarbon chains of the fatty alcohols of the jojoba oil, R'represents the hydrocarbon chains of the fatty acids of the jojoba oil, X is a straight or branched pr~ferably aliphatic hydrocarbon radical with at least 2 carbon atoms, preferably an alkyl radical with 2 or 3 carbon atoms, R'' is hydrogen, an alkyl group or a hydroylalkyl group, the total number of C atoms in X and R'' being from 2 to 6r M is an equivalent of a cation which is suitable for detergents and make the product water soluble, such as an alkali metal ion or an ammonium ion, Y is hydrogen and Y'is S03M or vice versa.
The following example and tests further illustrate the invention.
EXAMPLE
100 grams of jojoba oil are reacted with 10 grams of mon~ethanolamine in the presence of 0.1 gram of sodium methylate catalys-t or another well known saponification catalyst with stirring while raising the temperature slowly to 140 degree C, care being taken that some free alkali is available by adding some additional sodium methylate if required~ After a reaction period of 2 hours, a p~oduct is obtained wh.ich at room tempera-ture is a waxy solid and does not show any longer ester bandsin the IR-spectrum. The material is a mixture of the mono-ethanolamlde of jojoba fatty aaids and of jojoba fatty alcohol.
80 grams of this reaction mixture are reacted with 26 grams of maleic acid anhydride at a temperature of about 80 degree C for about 1 hour. The halfester mixture thus formed is then directly sulfonated by reaction with 34 grams sodium sulfite in 310 grams water by heating to about 80 degree C for 1/2 hour.
The reaction product obtained is a milk~ white disper-sion with a solid content of 30 percent by weight which after dilution with water forms anearly clear viscous liquid.
II1 the following tests,a mixture of sulfosuccinate halfesters according to the invention and based on jojoba oil (SB-J) is compared with a mixture of corresponding sul~o-succinate halfester of sperm oil.
1) Foaming capacity and foam stability according Roos Miles (0,1 % at 40 degree C, immediate and after 5 min~)
2) Wetting capacity according DI~ 53 901, 0,1 % in distilled water SB - ~12 sec.
SB - S10 sec.
SB - S10 sec.
3) Dispersing capacity for calcium soap according DI~ 53 903 Ss - S 11
4) Washing power The washing power was tested with a co-tton s-tandard fabric with artificial soiling. The fabric was washed in an automatical drum washing machine at 60 degree C and the wash lye was maintained at a content of active substance of 5 grams per liter. The washed test fabric was measured wi-th the 670 colour-and glossmeter of Pho-tovolt, ~ew York.
1. Measurement 2. r~easurement Untreated test fabric 82 % 82 %
Soiled test fabric 35 % 35 %
Soiled and washed test fabric A) SB - J 75 % 76 %
B ) SB - S 80 % U0 ~/o
1. Measurement 2. r~easurement Untreated test fabric 82 % 82 %
Soiled test fabric 35 % 35 %
Soiled and washed test fabric A) SB - J 75 % 76 %
B ) SB - S 80 % U0 ~/o
5) Swelllng in syndet soaps SB - J 12 %
SB - S 15 %
From these tests and comparision it is apparent that the sulfosuccinate halfester based on jojoba oil has a distintly lower foaming capacity what is of considerable interest for a number of applications. The substantially lower swelling value in syndet soaps is another advantage over sulfosuccinate based on sperm oil.
The new mixture of sulfosuccinate halfesters based on jojoba oil can be employed in household detergents, cosmetical compositions, shampoos and in other detergent compositions.
SB - S 15 %
From these tests and comparision it is apparent that the sulfosuccinate halfester based on jojoba oil has a distintly lower foaming capacity what is of considerable interest for a number of applications. The substantially lower swelling value in syndet soaps is another advantage over sulfosuccinate based on sperm oil.
The new mixture of sulfosuccinate halfesters based on jojoba oil can be employed in household detergents, cosmetical compositions, shampoos and in other detergent compositions.
Claims (5)
1. A process for preparing a mixture of sulfosuccinate halfesters, which comprises:
a) saponifying jojoba oil to fatty alcohol and to fatty acids, or b) transesterifying jojoba oil with a monovalent alcohol having from 1 to 3 carbon atoms to fatty alcohol and the corresponding fatty acid alkylesters, c) converting said fatty acids or said fatty acid alkylesters in the presence of said fatty alcohol to acyl alkanol amides by reaction with an amino alcohol, and d) reacting the mixture of fatty alcohol and acyl alkanol amides with maleic anhydride and sulfite to form sulfosuccinate halfesters.
a) saponifying jojoba oil to fatty alcohol and to fatty acids, or b) transesterifying jojoba oil with a monovalent alcohol having from 1 to 3 carbon atoms to fatty alcohol and the corresponding fatty acid alkylesters, c) converting said fatty acids or said fatty acid alkylesters in the presence of said fatty alcohol to acyl alkanol amides by reaction with an amino alcohol, and d) reacting the mixture of fatty alcohol and acyl alkanol amides with maleic anhydride and sulfite to form sulfosuccinate halfesters.
2. A mixture of sulfosuccinate halfesters based on jojoba oil, which contains compounds having the general formulae:
and wherein R represents the hydrocarbon chains of the fatty alcohols of jojoba oil, R' represents the hydrocarbon chains of the fatty acids of jojoba oil, X is a straight or branched hydro-carbon radical having at least 2 carbon atoms, R" is hydrogen, an alkyl or hydroxyalkyl group, the total number of carbon atoms in X and R" being from 2 to 6, M is an equivalent of a cation which is suitable for detergents and makes the product water soluble and Y and Y' which are different from one another each represents hydrogen or SO3M in which M has the aforesaid measning.
and wherein R represents the hydrocarbon chains of the fatty alcohols of jojoba oil, R' represents the hydrocarbon chains of the fatty acids of jojoba oil, X is a straight or branched hydro-carbon radical having at least 2 carbon atoms, R" is hydrogen, an alkyl or hydroxyalkyl group, the total number of carbon atoms in X and R" being from 2 to 6, M is an equivalent of a cation which is suitable for detergents and makes the product water soluble and Y and Y' which are different from one another each represents hydrogen or SO3M in which M has the aforesaid measning.
3. A mixture of sulfosuccinate halfesters according to claim 2, wherein X is an aliphatic hydrocarbon radical.
4. A mixture of sulfosuccinate halfesters according to claim 3, wherein X is an alkyl radical containing 2 or 3 carbon atoms.
5. A mixture of sulfosuccinate halfesters according to claims 2, 3 or 4, wherein M is an alkali metal ion or an ammonium ion.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772750732 DE2750732A1 (en) | 1977-11-12 | 1977-11-12 | Mixed sulpho-succinate half ester prodn. - from jojoba oil by saponification, conversion to acyl-alkanol:amide then reaction with maleic anhydride and sulphite |
| DEP2750732.0 | 1977-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1105485A true CA1105485A (en) | 1981-07-21 |
Family
ID=6023634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA316,176A Expired CA1105485A (en) | 1977-11-12 | 1978-11-14 | Mixture of sulfosuccinate halfester and process for the preparation thereof |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA1105485A (en) |
| DE (1) | DE2750732A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102197022A (en) * | 2008-10-24 | 2011-09-21 | 考格尼斯知识产权管理有限责任公司 | Alkyl sulfosuccinate mixtures, and use thereof |
| RU2605932C1 (en) * | 2015-10-08 | 2016-12-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Воронежский государственный университет" (ФГБОУ ВПО "ВГУ") | Method of producing sulfosuccinates of alkanolamides of fatty acids of vegetable oils |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE453828C (en) * | 1983-12-17 | 1988-07-18 | Inst Khim Akademii Nauk Estons | AMIN (OR AMMONIUM) AND ALKALIMETAL DOUBLE SALTS OF ACYLAMIDOALKYLEN (OR ACYLAMIDO-N-HYDROXIALKYL-N-ALKYL) SULPHOBARCYLIC ACID, PROCEDURE FOR PREPARING THEREOF, AS WELL AS SUBSEQUENTLY, AS WELL AS MANUFACTURING ITS ALSO SUBSEQUENTLY |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2490459A (en) * | 1946-04-10 | 1949-12-06 | Emulsol Corp | Paste shampoo |
| GB1281219A (en) * | 1969-08-11 | 1972-07-12 | Adolf Koebner | Sulphosuccinate compositions |
| DE2230073A1 (en) * | 1971-06-25 | 1972-12-28 | Unilever N.V., Rotterdam (Niederlande) | Alpha-substituted beta-sulfosuccinic acids and their use as builders in detergents |
-
1977
- 1977-11-12 DE DE19772750732 patent/DE2750732A1/en active Granted
-
1978
- 1978-11-14 CA CA316,176A patent/CA1105485A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102197022A (en) * | 2008-10-24 | 2011-09-21 | 考格尼斯知识产权管理有限责任公司 | Alkyl sulfosuccinate mixtures, and use thereof |
| RU2605932C1 (en) * | 2015-10-08 | 2016-12-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Воронежский государственный университет" (ФГБОУ ВПО "ВГУ") | Method of producing sulfosuccinates of alkanolamides of fatty acids of vegetable oils |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2750732A1 (en) | 1979-05-17 |
| DE2750732C2 (en) | 1991-05-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |