US1906484A - Soap preparation - Google Patents
Soap preparation Download PDFInfo
- Publication number
- US1906484A US1906484A US525603A US52560331A US1906484A US 1906484 A US1906484 A US 1906484A US 525603 A US525603 A US 525603A US 52560331 A US52560331 A US 52560331A US 1906484 A US1906484 A US 1906484A
- Authority
- US
- United States
- Prior art keywords
- soap
- acid
- parts
- per cent
- radicle
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- C—CHEMISTRY; METALLURGY
- 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
- C11D10/00—Compositions of detergents, not provided for by one single preceding group
- C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
- C11D10/042—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on anionic surface-active compounds and soap
-
- 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
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/06—Powder; Flakes; Free-flowing mixtures; Sheets
-
- 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
- C11D1/126—Acylisethionates
-
- 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
-
- 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
- C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
-
- 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
- Y10S516/04—Protein or carboxylic compound containing
Definitions
- JOSEPH N'UESSLEIN OF LUDWiGSHAFEN-ON-THE-RHINE, GERMANY, ASSIGNOR TO I. G. FARBENINDUSTRIE AKTIENGESELLSCHAFT, OF FRANKFORT-ON-THE-MAIN, GER- MANY SOAP PREPARATION No Drawing. Application filed March 26; 1931, Serial No. 525,603, and in Germany April 7, 1930.
- the present invention relates to new and basic oxygen-containing mineral acids, as
- non-aromatic i. e. aliphatic or cycloaliphatic alcohols or oleiines or olefinic alcohols having more than 8 carbon atoms, or of the true sulphonic acids, or their salts, of any non-armomat-ic, i. e.
- esters or amides aliphatic or hydroaromatic compounds containing at least 8 carbon atoms, preferably from 10 to 16 carbon atoms, as for example of acids of fats or oils of vegetable or animal origin, fatty acid esters, amides, or alcohols, ethers or hydrocarbons, in which esters or amides or other derivatives the sulphonic group may be contained in the component of low molecular weight.
- Such products are obtainable, for example, by the condensation of hydroxylated or halogenated derivatives of ethane, mono or di-sulphonic acid or of ethionic acid, carbyl sulphate or aminosulphonic acids with higher fatty acids, such as the fatty acids of vegetal origin or their synthetic equivalents, or their derivatives or salts of these compounds.
- esters and amides correspond to the general formula RCOXR SO Me,
- R denotes an aliphatic radicle
- er/an amino-alkylene radicle and Me denotes an alkali radicle.
- h ulp ric esters emp y according to the present invention may be obtained by treatin the alcohols or olefines with sulphonatmg agents, such as concentrated sulphuric acid, at a temperature up to about 35 C. sulphonic acids being obtained on working at about 100 C. or in the presence of agents removing Water such as anhydrides of strong inorganic polybasic acids or with the aid of sulphuric anhydride.
- sulphonatmg agents such as concentrated sulphuric acid
- the conversion of the said alcohols with the oxygen-containing polybasic mineral acids may be carried out for the production of the sulphuric esters by treating the alcohols with sulphuric acid, or chlorsulphonic acid in the presence of organic inert diluents, and for the production of the phosphoric esters by acting with phosphorus pentoxide on the alcohols in the presence of organic inert diluents.
- Small portions of the initial materials which have not been converted with the mineral acids, as for example fatty acids, neutral fats, parafiins and the like may be present in the finished product before it is incorporated with the soaps.
- esters employed is at least 5 per cent by weight of the soaps but in most cases considerably above 5 per cent will be used, especially as the sensitivity of the preparations to hard water is thus diminished; the esters may be employed, for example, in quantities of from 10, 20, 30, or 80 per cent of the soap but for the aforesaid reasons quantities of from 100 to about 1000 per cent are preferred in order to render the preparations particularly valuable for any purpose and in water of a high degree of hardness.
- soap substitutes may be added as well as salts of all kinds and the soap preparations may be adulterated with protective colloids, as for example albumious substances, vegetable gums, starch and the like.
- protective colloids as for example albumious substances, vegetable gums, starch and the like.
- organic solvents for many purposes, especiallyfor the dissolution and removalvof fat, oil or like stains, an addition of organic solvents to the soap preparations is advantageous.
- the known and, approved substances The parts are by weight.
- Ema/mple 1 80 parts of the sodium salt of the acid sulphuric ester of cetyl alcohol are intimately worked up with 10 parts of potassium and/or sodium stearate and 10 parts of glycerine' and pressed into moulds.
- the product is eminently suitable as a bath soap.
- Example 2 parts of the disodium salt of the sulphonic acid of stearic acid are ground with 10 parts of Glaubers salt, 10 parts of sodium palmitate and 10 parts of trisodium phosphate.
- a soap powder is obtained which has an excellent cleansing action.
- Example 3 80 parts of the neutral sodium salt of the condensation product of oleic acid chloride and ethionic acid are intimately mixed with 15 parts of sodium palmitate and 5 parts of sodium perborate. The product obtained has an excellent cleansing and bleaching action even in hard water.
- E wample 4 30 parts of the neutral ammonium salt of the acid sulphuric ester of stearyl alcohol together with 30 parts of ammonium oleate and 40 parts of water are kneaded into a homogeneous paste.
- the preparation possesses a good cleansing action which may be increased by the addition of 5 parts of cyclohexanol.
- Example 5 100 parts of a normal grain soap paste containing about 65 per cent of fatty acid is kneaded with a concentrated solution of 10 parts of the neutral sodium salt of the sulphuric ester of laur 1 alcohol. The mixture is worked up in t e usual manner into shreds or flakes which are distinguished by their high solubility. 1 per cent by weight of the mass of purified lemon grass oil may be added in order to give a. fresh smell to the soap.
- Soap preparations comprising an alkali metal soap and from 100 to about 1000 per cent, by weight of the soap, of neutralized sulphonic acid corresponding to the formula R.COO.C H .SO H in which RCOO is the radicle of a fatty acid of vegetal origin.
- Soap preparations comprising an alkali metal soap and from 100 to about 1000 per cent, by. weight of the soap, of an alkali metal salt of a sul honic acid corresponding to the formula R. OO.G H.,.SO H in which H.600 is the radicle of a fatty acid of vegetal origin.
- Soap preparations comprising an alkali metal soap and from 100 to about 1000 per cent, by weight of the soap, of an alkali metal salt of a sul honic acid corresponding to the formula R. OO.C H .SO H in which RG00 is the radicle of oleic acid.
- Soap preparations comprising a soap derived from a water-soluble base and at least 5 per cent, by weight of the soap, of a true sulphonic acid substance containing at least 8 carbon atoms and corresponding to the formula RCOX- -R SO -OMe in which R denotes an aliphatic radicle, XR denotes an oxalkylene (O-R or an amino-alkylene radicle and Me denotes an alkali radicle.
- Soap preparations comprising a soap derived from a water-soluble base and from 100 to about 1000 per cent, by weight of the soap, of a true sulphonic acid substance containing at least 8 carbon atoms and corresponding to the formula.
- R denotes an aliphatic radicle
- XR denotes an oxalkylene (OR or an aminolene radicle
- Me denotes an alkali radio e.
- Soap preparations comprising an alkali metal soap and from 100 to about 1000 per 5 cent, by weight of the soap, of a true sulmy hand. 5 JOSEPH NUESSLEIN.
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)
Description
Patented May 2, 1933 UNITED STATES PATENT OFFICE.
JOSEPH N'UESSLEIN, OF LUDWiGSHAFEN-ON-THE-RHINE, GERMANY, ASSIGNOR TO I. G. FARBENINDUSTRIE AKTIENGESELLSCHAFT, OF FRANKFORT-ON-THE-MAIN, GER- MANY SOAP PREPARATION No Drawing. Application filed March 26; 1931, Serial No. 525,603, and in Germany April 7, 1930.
The present invention relates to new and basic oxygen-containing mineral acids, as
for example sulphuric acid or phosphoric acid, and non-aromatic, i. e. aliphatic or cycloaliphatic alcohols or oleiines or olefinic alcohols having more than 8 carbon atoms, or of the true sulphonic acids, or their salts, of any non-armomat-ic, i. e. aliphatic or hydroaromatic compounds containing at least 8 carbon atoms, preferably from 10 to 16 carbon atoms, as for example of acids of fats or oils of vegetable or animal origin, fatty acid esters, amides, or alcohols, ethers or hydrocarbons, in which esters or amides or other derivatives the sulphonic group may be contained in the component of low molecular weight. Such products are obtainable, for example, by the condensation of hydroxylated or halogenated derivatives of ethane, mono or di-sulphonic acid or of ethionic acid, carbyl sulphate or aminosulphonic acids with higher fatty acids, such as the fatty acids of vegetal origin or their synthetic equivalents, or their derivatives or salts of these compounds. These last-mentioned esters and amides correspond to the general formula RCOXR SO Me,
in Which R denotes an aliphatic radicle,
" er/an amino-alkylene radicle and Me denotes an alkali radicle. Thus, for example,
' acid sulphuric esters of high molecular aloxidation of paraffin hydrocarbons, may be I. very advantageously employed. h ulp ric esters emp y according to the present invention may be obtained by treatin the alcohols or olefines with sulphonatmg agents, such as concentrated sulphuric acid, at a temperature up to about 35 C. sulphonic acids being obtained on working at about 100 C. or in the presence of agents removing Water such as anhydrides of strong inorganic polybasic acids or with the aid of sulphuric anhydride.
The conversion of the said alcohols with the oxygen-containing polybasic mineral acids may be carried out for the production of the sulphuric esters by treating the alcohols with sulphuric acid, or chlorsulphonic acid in the presence of organic inert diluents, and for the production of the phosphoric esters by acting with phosphorus pentoxide on the alcohols in the presence of organic inert diluents. Small portions of the initial materials which have not been converted with the mineral acids, as for example fatty acids, neutral fats, parafiins and the like may be present in the finished product before it is incorporated with the soaps.
The quality of the aforesaid esters employed is at least 5 per cent by weight of the soaps but in most cases considerably above 5 per cent will be used, especially as the sensitivity of the preparations to hard water is thus diminished; the esters may be employed, for example, in quantities of from 10, 20, 30, or 80 per cent of the soap but for the aforesaid reasons quantities of from 100 to about 1000 per cent are preferred in order to render the preparations particularly valuable for any purpose and in water of a high degree of hardness.
If desired, soap substitutes may be added as well as salts of all kinds and the soap preparations may be adulterated with protective colloids, as for example albumious substances, vegetable gums, starch and the like. For many purposes, especiallyfor the dissolution and removalvof fat, oil or like stains, an addition of organic solvents to the soap preparations is advantageous. In order to produce special cosmetic pharmaceutical, insecticidal or germicidal effects, the known and, approved substances The parts are by weight.
Ema/mple 1 80 parts of the sodium salt of the acid sulphuric ester of cetyl alcohol are intimately worked up with 10 parts of potassium and/or sodium stearate and 10 parts of glycerine' and pressed into moulds. The product is eminently suitable as a bath soap.
Example 2 parts of the disodium salt of the sulphonic acid of stearic acid are ground with 10 parts of Glaubers salt, 10 parts of sodium palmitate and 10 parts of trisodium phosphate. A soap powder is obtained which has an excellent cleansing action.
Example 3 80 parts of the neutral sodium salt of the condensation product of oleic acid chloride and ethionic acid are intimately mixed with 15 parts of sodium palmitate and 5 parts of sodium perborate. The product obtained has an excellent cleansing and bleaching action even in hard water.
Similar results are obtained by. employing taurine instead of ethionic acid.
E wample 4 30 parts of the neutral ammonium salt of the acid sulphuric ester of stearyl alcohol together with 30 parts of ammonium oleate and 40 parts of water are kneaded into a homogeneous paste. The preparation possesses a good cleansing action which may be increased by the addition of 5 parts of cyclohexanol.
Example 5 100 parts of a normal grain soap paste containing about 65 per cent of fatty acid is kneaded with a concentrated solution of 10 parts of the neutral sodium salt of the sulphuric ester of laur 1 alcohol. The mixture is worked up in t e usual manner into shreds or flakes which are distinguished by their high solubility. 1 per cent by weight of the mass of purified lemon grass oil may be added in order to give a. fresh smell to the soap.
Ewample 6' 25 parts of an about 80 per cent aqueous paste of the neutral sodium salt of the prodnot obtained by the action of gaseous sulphur trioxide on dodecylene are worked into 100 parts of a solid coco soap. The soap preparation obtained has an excellent foammg power.
For preparing a very good bath soap, from /2 to 1 per cent of a suitable perfume composition stable to alkali may be added.
What I claim is 1. Soap preparations comprising an alkali metal soap and from 100 to about 1000 per cent, by weight of the soap, of neutralized sulphonic acid corresponding to the formula R.COO.C H .SO H in which RCOO is the radicle of a fatty acid of vegetal origin.
2. Soap preparations comprising an alkali metal soap and from 100 to about 1000 per cent, by. weight of the soap, of an alkali metal salt of a sul honic acid corresponding to the formula R. OO.G H.,.SO H in which H.600 is the radicle of a fatty acid of vegetal origin.
3. Soap preparations comprising an alkali metal soap and from 100 to about 1000 per cent, by weight of the soap, of an alkali metal salt of a sul honic acid corresponding to the formula R. OO.C H .SO H in which RG00 is the radicle of oleic acid.
4. Soap preparations comprising a soap derived from a water-soluble base and at least 5 per cent, by weight of the soap, of a true sulphonic acid substance containing at least 8 carbon atoms and corresponding to the formula RCOX- -R SO -OMe in which R denotes an aliphatic radicle, XR denotes an oxalkylene (O-R or an amino-alkylene radicle and Me denotes an alkali radicle.
5. Soap preparations comprising a soap derived from a water-soluble base and from 100 to about 1000 per cent, by weight of the soap, of a true sulphonic acid substance containing at least 8 carbon atoms and corresponding to the formula.
in which R denotes an aliphatic radicle, ---XR denotes an oxalkylene (OR or an aminolene radicle and Me denotes an alkali radio e.
6. Soap preparations comprising an alkali metal soap and from 100 to about 1000 per 5 cent, by weight of the soap, of a true sulmy hand. 5 JOSEPH NUESSLEIN.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE638302T | 1930-04-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
US1906484A true US1906484A (en) | 1933-05-02 |
Family
ID=34812936
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US525603A Expired - Lifetime US1906484A (en) | 1930-04-08 | 1931-03-26 | Soap preparation |
Country Status (5)
Country | Link |
---|---|
US (1) | US1906484A (en) |
BE (1) | BE378069A (en) |
DE (1) | DE638302C (en) |
FR (1) | FR712913A (en) |
NL (1) | NL55394C (en) |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2494580A (en) * | 1947-05-24 | 1950-01-17 | Procter & Gamble | Detergent composition |
US2508578A (en) * | 1944-05-05 | 1950-05-23 | Colgate Palmolive Peet Co | Combined soap and synthetic detergent bar |
US2567645A (en) * | 1947-05-16 | 1951-09-11 | Shell Dev | Process of producing a detergent composition |
US2603606A (en) * | 1952-07-15 | Alkyl sulfates | ||
US2739130A (en) * | 1956-03-20 | Cleaning composition | ||
US2749315A (en) * | 1951-04-28 | 1956-06-05 | Colgate Palmolive Co | Toilet detergent bar and process of preparing same |
US2765279A (en) * | 1949-03-11 | 1956-10-02 | Metallgesellschaft Ag | Shaped mixture of soap and phosphonate |
US2781320A (en) * | 1957-02-12 | All purpose | ||
US2781321A (en) * | 1953-05-12 | 1957-02-12 | Gen Aniline & Film Corp | All purpose detergent bar |
US2865811A (en) * | 1952-05-02 | 1958-12-23 | Irval Cosmetics Inc | Hair straightener containing a kerating reducing agent, anionic wetting agent and water-soluble soap and method of using same |
US2886585A (en) * | 1956-08-15 | 1959-05-12 | Drew & Co Inc E F | Method of making a synthetic detergent in cake form |
US2894912A (en) * | 1954-09-21 | 1959-07-14 | Lever Brothers Ltd | Isethionate detergent bar |
US2988511A (en) * | 1955-03-31 | 1961-06-13 | Mills Victor | Nonsmearing detergent bar |
US2991253A (en) * | 1952-08-20 | 1961-07-04 | Armour & Co | Solid soap composition |
US3043778A (en) * | 1958-02-20 | 1962-07-10 | Lever Brothers Ltd | Soap bar compositions |
US3057805A (en) * | 1962-10-09 | Synthetic detergent cake and process | ||
US3070547A (en) * | 1953-07-13 | 1962-12-25 | Procter & Gamble | Soap-synthetic bar |
US3224976A (en) * | 1960-05-20 | 1965-12-21 | Colgate Palmolive Co | Detergent bar |
US4260507A (en) * | 1970-08-18 | 1981-04-07 | Lever Brothers Company | Soap-synthetic detergent tablets |
US4476055A (en) * | 1982-07-06 | 1984-10-09 | Westvaco Corporation | C21-Dicarboxylic acid isethionates as primary anionic surfactants |
US4514335A (en) * | 1982-07-06 | 1985-04-30 | Westvaco Corporation | C21 -Dicarboxylic acid isethionates as primary anionic surfactants |
US4571309A (en) * | 1983-07-20 | 1986-02-18 | Westvaco Corporation | C22 -Cycloaliphatic tricarboxylic acid derived isethionate esters and method of preparation |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE895289C (en) * | 1934-07-03 | 1953-11-02 | Bataafsche Petroleum | Process for preparing salts of acidic alkyl esters |
DE750286C (en) * | 1935-05-02 | 1945-01-03 | Kalle & Co Ag | Soap-free detergents |
DE895815C (en) * | 1940-01-06 | 1953-11-05 | Basf Ag | laundry detergent |
CA636022A (en) * | 1958-04-14 | 1962-02-06 | California Research Corporation | Detergent bar |
DE1111761B (en) * | 1959-09-25 | 1961-07-27 | Shell Int Research | Toilet soap |
BE611781A (en) * | 1960-12-23 |
-
0
- BE BE378069D patent/BE378069A/xx unknown
- NL NL55394D patent/NL55394C/xx active
-
1930
- 1930-04-08 DE DE1930638302D patent/DE638302C/en not_active Expired
-
1931
- 1931-03-09 FR FR712913D patent/FR712913A/en not_active Expired
- 1931-03-26 US US525603A patent/US1906484A/en not_active Expired - Lifetime
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3057805A (en) * | 1962-10-09 | Synthetic detergent cake and process | ||
US2603606A (en) * | 1952-07-15 | Alkyl sulfates | ||
US2739130A (en) * | 1956-03-20 | Cleaning composition | ||
US2781320A (en) * | 1957-02-12 | All purpose | ||
US2508578A (en) * | 1944-05-05 | 1950-05-23 | Colgate Palmolive Peet Co | Combined soap and synthetic detergent bar |
US2567645A (en) * | 1947-05-16 | 1951-09-11 | Shell Dev | Process of producing a detergent composition |
US2494580A (en) * | 1947-05-24 | 1950-01-17 | Procter & Gamble | Detergent composition |
US2765279A (en) * | 1949-03-11 | 1956-10-02 | Metallgesellschaft Ag | Shaped mixture of soap and phosphonate |
US2749315A (en) * | 1951-04-28 | 1956-06-05 | Colgate Palmolive Co | Toilet detergent bar and process of preparing same |
US2865811A (en) * | 1952-05-02 | 1958-12-23 | Irval Cosmetics Inc | Hair straightener containing a kerating reducing agent, anionic wetting agent and water-soluble soap and method of using same |
US2991253A (en) * | 1952-08-20 | 1961-07-04 | Armour & Co | Solid soap composition |
US2781321A (en) * | 1953-05-12 | 1957-02-12 | Gen Aniline & Film Corp | All purpose detergent bar |
US3070547A (en) * | 1953-07-13 | 1962-12-25 | Procter & Gamble | Soap-synthetic bar |
US2894912A (en) * | 1954-09-21 | 1959-07-14 | Lever Brothers Ltd | Isethionate detergent bar |
US2988511A (en) * | 1955-03-31 | 1961-06-13 | Mills Victor | Nonsmearing detergent bar |
US2886585A (en) * | 1956-08-15 | 1959-05-12 | Drew & Co Inc E F | Method of making a synthetic detergent in cake form |
US3043778A (en) * | 1958-02-20 | 1962-07-10 | Lever Brothers Ltd | Soap bar compositions |
US3224976A (en) * | 1960-05-20 | 1965-12-21 | Colgate Palmolive Co | Detergent bar |
US4260507A (en) * | 1970-08-18 | 1981-04-07 | Lever Brothers Company | Soap-synthetic detergent tablets |
US4476055A (en) * | 1982-07-06 | 1984-10-09 | Westvaco Corporation | C21-Dicarboxylic acid isethionates as primary anionic surfactants |
US4514335A (en) * | 1982-07-06 | 1985-04-30 | Westvaco Corporation | C21 -Dicarboxylic acid isethionates as primary anionic surfactants |
US4571309A (en) * | 1983-07-20 | 1986-02-18 | Westvaco Corporation | C22 -Cycloaliphatic tricarboxylic acid derived isethionate esters and method of preparation |
Also Published As
Publication number | Publication date |
---|---|
FR712913A (en) | 1931-10-15 |
NL55394C (en) | |
BE378069A (en) | |
DE638302C (en) | 1936-11-13 |
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