US1981792A - Sulphated condensation products of - Google Patents
Sulphated condensation products of Download PDFInfo
- Publication number
- US1981792A US1981792A US1981792DA US1981792A US 1981792 A US1981792 A US 1981792A US 1981792D A US1981792D A US 1981792DA US 1981792 A US1981792 A US 1981792A
- Authority
- US
- United States
- Prior art keywords
- acid
- wetting
- acids
- fatty acids
- monoethanolamine
- 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
- 239000007859 condensation product Substances 0.000 title description 24
- 239000002253 acid Substances 0.000 description 56
- 235000014113 dietary fatty acids Nutrition 0.000 description 40
- 239000000194 fatty acid Substances 0.000 description 40
- 150000004665 fatty acids Chemical class 0.000 description 40
- 150000007513 acids Chemical class 0.000 description 32
- 239000000080 wetting agent Substances 0.000 description 32
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- 239000003995 emulsifying agent Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000002270 dispersing agent Substances 0.000 description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- 239000001117 sulphuric acid Substances 0.000 description 18
- 235000011149 sulphuric acid Nutrition 0.000 description 18
- 235000013162 Cocos nucifera Nutrition 0.000 description 16
- 240000007170 Cocos nucifera Species 0.000 description 16
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 10
- 238000009736 wetting Methods 0.000 description 8
- 235000021314 Palmitic acid Nutrition 0.000 description 6
- 125000004432 carbon atoms Chemical group C* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 235000015450 Tilia cordata Nutrition 0.000 description 4
- 235000011941 Tilia x europaea Nutrition 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000000749 insecticidal Effects 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 239000004571 lime Substances 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 235000019488 nut oil Nutrition 0.000 description 4
- 239000010466 nut oil Substances 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N Hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- GGLZPLKKBSSKCX-YFKPBYRVSA-N L-ethionine Chemical compound CCSCC[C@H](N)C(O)=O GGLZPLKKBSSKCX-YFKPBYRVSA-N 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000001627 detrimental Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 230000001804 emulsifying Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002169 ethanolamines Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 150000002194 fatty esters Chemical class 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- -1 monobutyl amines Chemical class 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- 230000000149 penetrating Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N triclene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
-
- 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
- Y10S516/05—Organic amine, amide, or n-base containing
Definitions
- My present invention relates to improvements in wetting, dispersing and emulsifying agents and more particularly to the sulphonated condensation products of certain fatty acids and the mono- 5 alkyl amines, as for example monoethanol amines. While it has been proposed to condense certain of the fatty acids or esters thereof with various amines, the proper acids or mixtures thereof have not been condensed with a proper amine. In
- Sulphuric acid treated condensation product formed from:
- First fraction composed of 85% C10 acid 64 sec.
- Second fraction composed of 64% C12 acid -1 33 sec.
- Third fraction composed of 87% Ca acid 2'7 sec.
- Fourth fraction composed of 89% C14 acid 35 sec.
- Fifth fraction composed of 90% Cm 35 acid 90 sec.
- 'Pure stearic acid (Cm acid) f 600 sec.
- the wetting agent will be most eflicient, other factors being equal, when the fatty soluble chain and the water soluble chain will be balanced or of equal strength. For instance, if the oil soluble function is much stronger than the water soluble, the molecule will tend to be withdrawn mostly into the oil layer and poorer wetting power will result. If, on the other hand,
- This product may be subjected to the action of sulphuric acid in the following manner:
- the amount of sulphuric acid used in the sulphonation is not critical, except that a large excess, as for example double the amount specified, is detrimental. Furthermore, while the temperature may vary within limits, it should not exceed C. More active sulphonating agents may be used as desired, such as chlor-sulphonic, ethionic acid, oleum, etc. However, I have found that the ordinary sulphuric acid monohydrate is sufliciently active for the purpose. In the condensation products described there is only one hydroxyl group.
- the sulphated products of my invention are an almost white, thick paste, having remarkable detergent and emulsifying properties. These products when used in the dye bath even in very high dilutions give thorough and even dyeing and an excellent feel to the goods.
- the product is fast to lime, disperses lime soaps and is fast to acid and alkali. It may be incorporated with soap as a soap assistant or it may be used as an emulsifying agent in greases, creams and cosmetics, in securing, as a penetrating agent, in the tanning industry to accelerate tanning, deoiling, dehairing, etc. It may also be used with insecticides to increase their covering power in aqueous form and in such capacity it is termed an insecticide promoter.
- the product may be dried in a vacuum and reduced to a fine white powder.
- the monopropan01 amines and monobutyl amines may be used.
- the new products according to claim 1 being the condensation of a single molecule of fatty acid, a single molecule of amine and a single molecule of sulphuric acid.
- the new products according to claim 2 being the condensation of a single molecule of fatty acid, a single molecule of amine and a single molecule of sulphuric acid.
- the method of making wetting, dispersing 15.
- the method of making wetting,dispersing and emulsifying agents which consists in condensing fatty acids containing a substantial quantity of the acids having from 12 to 14 (inclusive) carbon atoms with monoethanolamine by heating said compounds together until the I acid number, as determined in alcohol, sinks to below 5 while allowing the water evolved to'
Description
PATENT OFFICE SULPHATED CONDENSATION PRODUCTS OF l lill'a.l".l.Y ACIDS AND MONOETHANOLAM- John W. Orelup, Summit, N. J.
No Drawing.
15 Claims;
My present invention relates to improvements in wetting, dispersing and emulsifying agents and more particularly to the sulphonated condensation products of certain fatty acids and the mono- 5 alkyl amines, as for example monoethanol amines. While it has been proposed to condense certain of the fatty acids or esters thereof with various amines, the proper acids or mixtures thereof have not been condensed with a proper amine. In
many cases the condensation products so obtained have not been treated with sulphuric acid to form compounds therewith. In all casesthe proposed products have been practically worthless. The following table gives results obtained by observing the sinking time of a piece of wool serge 4 x 4 in a solution of one gram of the wetting agent per litre of tap water of average hardness. The wetting agents were all made by condensing the acid mixture indicated with monoethanolamine followed by treatment with sulphuric acid as described in detail below.
' Sinking time at 26 C.
Sulphuric acid treated condensation product formed from:
First fraction composed of 85% C10 acid 64 sec. Second fraction composed of 64% C12 acid -1 33 sec. Third fraction composed of 87% Ca acid 2'7 sec. Fourth fraction composed of 89% C14 acid 35 sec. Fifth fraction composed of 90% Cm 35 acid 90 sec. Pure palmitic acid (C16 acid) 1320 sec. 'Pure stearic acid (Cm acid) f 600 sec. Methyl ester of palmitic acid 2400 sec. In concentration of 5 grams per liter: 40 Pure palmitic acid 135 sec. Methyl ester of palmitic' acid 275. sec.
Without wetting agents 24 hours.
These acids from which the wetting agents were derived were obtained by fractionating the cocoanut fatty acids containing acids from Ca to C18, i. e. capronic, caproic, capryllic, lauric, myristic, palmitic, stearic by .distillation. It will be seen that the wetting activity reaches a maximum between C12 and C14 acids. Cu; is almost inactive and Cs on the other side is less active than C12 or C14. Because of the predominance of the C12 and C14. acids in cocoanut oil very good results are obtained by using the fatty acids naturally occurringin cocoanut oil or other nut oils of similar composition such as palm kernel oil. In fact, mixtures of several of these fatty acids, such as the mixture of acids in the proportions in which they occur in cocoanut oil and palm nut oil, seem to yield better results than Application June 17, 1933, Serial No. 676,324
are obtained with the C12 or C14 acids alone.
water soluble as entering into the water layer at the surface or interface of the material to be wetted. Now the wetting agent will be most eflicient, other factors being equal, when the fatty soluble chain and the water soluble chain will be balanced or of equal strength. For instance, if the oil soluble function is much stronger than the water soluble, the molecule will tend to be withdrawn mostly into the oil layer and poorer wetting power will result. If, on the other hand,
the water soluble chain surpasses in power the.
oil soluble chain, a tendency for the withdrawal of the molecule into the water results, again with loss of Wetting power. Thus applying this reasoning to the above table, it may be considered that the C12 and C14 groups are the best balanced of the acids given. My theory finds further confirmation in the action of cbmpounds in which the polar activity is increased by the addition of more hydroxyl groups, as by using diethanolamine in the sulphonation product instead of the mono compound. The sinking power is poorer, being of the order of 171 seconds in the concentration of 1 gram per litre. By increasing these groups still further by using triethanolamine the sinking time is raised to 480 seconds.
In order that my invention may be fully understood, I give the following illustrative example using the naturally occurring cocoanut fatty acids:
210 pounds of cocoanut fatty acids having an average molecular weight of 210 is heated with 67 pounds of monoethanolamine for a fewhours in a still until the acid number determined in alcohol sinks to below 5, the water evolved being allowed to escape. The distillate of water and excess 'monoethanolamine amounts to about 19 pounds. The mass on cooling sets to a pale yellow wax-like substance having a solidification point of 60-65" C., and may be sulphonated directly. This product is slightly soluble in water.
This product may be subjected to the action of sulphuric acid in the following manner:
To 100 pounds of sulphuric acid monohydrate pletely homogeneous, tests are made to determine the water solubility. -As soon as the solubility is complete, the mass is mixed with '75 pounds of ice and neutralized while cooling with suflioient 50% caustic soda to bring the whole to a neutral reaction to litmus. The excess sulphuric acid may also be separated by slight dilution or salted out.
This treatment results, as nearly as can beascertained, in the formation of a predominant quantity of the sulphuric esters in which the sulphur atom is joined to the compound by an oxygen linkage and possibly of some slight quantities of true sulphonated compounds in which the sulphur is attached to the carbon atoms. To the type of reaction with sulphuric acid exemplified by said treatment I apply herein the term sulphation.
The amount of sulphuric acid used in the sulphonation is not critical, except that a large excess, as for example double the amount specified, is detrimental. Furthermore, while the temperature may vary within limits, it should not exceed C. More active sulphonating agents may be used as desired, such as chlor-sulphonic, ethionic acid, oleum, etc. However, I have found that the ordinary sulphuric acid monohydrate is sufliciently active for the purpose. In the condensation products described there is only one hydroxyl group.
Contrary to the sulphonated fatty alcohol series, it has been found that the saturated fatty acids give more active compounds with ethanolamine followed by sulphation than the unsaturated. Inert solvents may also be used in the treatment as, for example, trichlorethylene, carbon tetrachloride, etc., but it has been my experience that the advantage so gained does not usually warrant the expense entailed by the use of solvents.
The sulphated products of my invention are an almost white, thick paste, having remarkable detergent and emulsifying properties. These products when used in the dye bath even in very high dilutions give thorough and even dyeing and an excellent feel to the goods. The product is fast to lime, disperses lime soaps and is fast to acid and alkali. It may be incorporated with soap as a soap assistant or it may be used as an emulsifying agent in greases, creams and cosmetics, in securing, as a penetrating agent, in the tanning industry to accelerate tanning, deoiling, dehairing, etc. It may also be used with insecticides to increase their covering power in aqueous form and in such capacity it is termed an insecticide promoter. The product may be dried in a vacuum and reduced to a fine white powder.
In lieu of monoethanolamine, the monopropan01 amines and monobutyl amines may be used.
I claim:
1. As new wetting, dispersing and emulsifying agents, the sulphated product of the condensation reaction of the fatty acids containing a substantial quantity of the C12 and C14 acids withmonoethanolamine.
2. As new wetting, dispersing and emulsifying agents, the sulphated product of the condensation reaction of the naturally occurring fatty acids in cocoanut oil, with monoethanolamine.
3. The new products according to claim 1 being the condensation of a single molecule of fatty acid, a single molecule of amine and a single molecule of sulphuric acid.
4. The new products according to claim 2 being the condensation of a single molecule of fatty acid, a single molecule of amine and a single molecule of sulphuric acid.
5. As new wetting, dispersing and emulsifying agents, the sulphated condensation of products of equi-molar quantities of the naturally occurring fattyacids in cocoanut oil and monoethanolamine. 6. The method of making wetting, dispersing and emulsifying agents which consists in condensing fatty acids containing a substantial quantity of the C12 and C14 acids with monoethanolamine and sulphating the condensation product formed.
7. The method of making wetting, dispersing and emulsifying agents which consists in condensing fatty acids containing a substantial quantity of the C12 and C14 acids with monoethanolamine and sulphating the condensation product formed.
8. In the manufacture of wetting, dispersing and emulsifying agents, the steps of condensing fatty acids containing a substantial quantity of the C12 and C14 acids with monoethanolamine followed by sulphation in which the condensation product is treated with a substantially equal quantity by weight of sulphuric acid mono-hydrate until the mass is homogeneous and water soluble.
9. The method according to the preceding claim in which the temperature of sulphation is maintained at from 30 to 35 C.
10. As new wetting, dispersing, and emulsifying agents, the sulphated condensation products of fatty acids and monoethanolamine in which the respective dissolving powers of the polar and nonpolar components are substantially the same magnitude.
11. As new wetting, dispersing and emulsifying agents, the sulphation products of an acid amide formed by condensing monoethanolamine with a mixture of fatty acids between C10 and C18- 12. The method of making wetting, dispersing and emulsifying agents which consists in condensing fatty acids containing a substantial quantity of the C12 and C14 acids with monoethanolamine by heating such compounds together until the acid number sinks to below 5, and sulphating the condensation product formed.
13. The method of makingwetting, dispersing and emulsifying agents which consists in condensing fatty acids containing a substantial quantity of the acids having from 12 to 14 (inclusive) carbon atoms with monoethanolamine by heating said compounds together until the water formed by the reaction is substantially driven off and sulphating the condensation product formed.
14. The method of making wetting, dispersing 15. The method of making wetting,dispersing and emulsifying agents which consists in condensing fatty acids containing a substantial quantity of the acids having from 12 to 14 (inclusive) carbon atoms with monoethanolamine by heating said compounds together until the I acid number, as determined in alcohol, sinks to below 5 while allowing the water evolved to'
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1981792A true US1981792A (en) | 1934-11-20 |
Family
ID=3426735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1981792D Expired - Lifetime US1981792A (en) | Sulphated condensation products of |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1981792A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2545357A (en) * | 1946-06-04 | 1951-03-13 | American Cyanamid Co | Detergent composition and method of preparing same |
| US2581677A (en) * | 1952-01-08 | Phosphate detergent composition in | ||
| US2843550A (en) * | 1954-03-02 | 1958-07-15 | California Research Corp | Synthetic detergent compositions |
| US4116986A (en) * | 1977-05-06 | 1978-09-26 | The United States Of America As Represented By The Secretary Of Agriculture | Process for sulfating fatty alkanolamides |
| US4252665A (en) * | 1979-06-13 | 1981-02-24 | Monsanto Company | Disinfectant cleaning compositions |
| EP0780367A2 (en) | 1995-12-19 | 1997-06-25 | Henkel Kommanditgesellschaft auf Aktien | Anionic detergent mixture |
| US20090291864A1 (en) * | 2001-02-13 | 2009-11-26 | Schlumberger Technology Corporation | Viscoelastic compositions |
-
0
- US US1981792D patent/US1981792A/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2581677A (en) * | 1952-01-08 | Phosphate detergent composition in | ||
| US2545357A (en) * | 1946-06-04 | 1951-03-13 | American Cyanamid Co | Detergent composition and method of preparing same |
| US2843550A (en) * | 1954-03-02 | 1958-07-15 | California Research Corp | Synthetic detergent compositions |
| US4116986A (en) * | 1977-05-06 | 1978-09-26 | The United States Of America As Represented By The Secretary Of Agriculture | Process for sulfating fatty alkanolamides |
| US4252665A (en) * | 1979-06-13 | 1981-02-24 | Monsanto Company | Disinfectant cleaning compositions |
| EP0780367A2 (en) | 1995-12-19 | 1997-06-25 | Henkel Kommanditgesellschaft auf Aktien | Anionic detergent mixture |
| US20090291864A1 (en) * | 2001-02-13 | 2009-11-26 | Schlumberger Technology Corporation | Viscoelastic compositions |
| US8785355B2 (en) | 2001-02-13 | 2014-07-22 | Schlumberger Technology Corporation | Viscoelastic compositions |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH06502402A (en) | Method for producing a concentrated aqueous dispersion of α-sulfo fatty acid monosalt and/or disalt | |
| US2271619A (en) | Process of making pure soaps | |
| EP0247509B1 (en) | Process for the manufacture of natural fat or oil derivatives, being liquid or having cold-flowing properties at room temperature, and their use | |
| US2527076A (en) | Detergent composition | |
| US1981792A (en) | Sulphated condensation products of | |
| US4903362A (en) | Sulfited fats as oiling agents for leather and skins | |
| US2366027A (en) | Detergent and wetting compositions | |
| US3627822A (en) | Novel compounds with detergency and fabric-softening ability and method of making the same | |
| CN114746603A (en) | Softening base | |
| US2235098A (en) | Aliphatic sulphates and method of | |
| US1968794A (en) | Process of making sulphuric reaction products of aliphatic alcohols | |
| US2156996A (en) | Detergent and wetting compositions | |
| WO1992000959A1 (en) | New thiodiglycolalkoxylate derivatives, method for their preparation, and their use as textile softeners | |
| US2527075A (en) | Detergent composition | |
| US2088019A (en) | Secondary alkyl sulphates as wetting agents | |
| US2044400A (en) | Sulphonation of oils or their fatty acids | |
| DE4003096A1 (en) | SULFURED HYDROXYCARBONIC ACID ESTERS | |
| US1543157A (en) | Process of obtaining sulphonated products of wool fat | |
| JPH09512844A (en) | Cationic formulations for fatting leather and fur | |
| US2584701A (en) | Surface-active compounds | |
| US2044399A (en) | Sulphonation of waxes | |
| US2938872A (en) | Sulfated chloroalkanol detergents | |
| Trusler | Ethanolamine soaps | |
| US2283437A (en) | x c chacl | |
| EP0763139B1 (en) | Stuffing agents for leathers and fur-skins |