US2765279A - Shaped mixture of soap and phosphonate - Google Patents
Shaped mixture of soap and phosphonate Download PDFInfo
- Publication number
- US2765279A US2765279A US322563A US32256352A US2765279A US 2765279 A US2765279 A US 2765279A US 322563 A US322563 A US 322563A US 32256352 A US32256352 A US 32256352A US 2765279 A US2765279 A US 2765279A
- Authority
- US
- United States
- Prior art keywords
- soap
- acid
- mixture
- phosphonate
- salts
- 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
- 239000000203 mixture Substances 0.000 title claims description 8
- 239000000344 soap Substances 0.000 title description 7
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 title description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- -1 STEARYL AMINO PHENYL PHOSPHONIC ACID Chemical compound 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 235000019864 coconut oil Nutrition 0.000 claims description 3
- 239000003240 coconut oil Substances 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 239000012459 cleaning agent Substances 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 6
- 150000003007 phosphonic acid derivatives Chemical class 0.000 description 6
- 239000003599 detergent Substances 0.000 description 5
- 235000011007 phosphoric acid Nutrition 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 150000005374 primary esters Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BMYBKYQDGKGCSU-UHFFFAOYSA-N (2-aminophenyl)phosphonic acid Chemical compound NC1=CC=CC=C1P(O)(O)=O BMYBKYQDGKGCSU-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000008028 secondary esters Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C11D1/34—Derivatives of acids of phosphorus
- C11D1/345—Phosphates or phosphites
-
- 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
- C11D1/34—Derivatives of acids of phosphorus
- C11D1/342—Phosphonates; Phosphinates or phosphonites
-
- 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
- C11D9/00—Compositions of detergents based essentially on soap
- C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
- C11D9/22—Organic compounds, e.g. vitamins
- C11D9/34—Organic compounds, e.g. vitamins containing phosphorus
Definitions
- the phosphonic acids may contain the same radicals which are described in the co-pending application Ser. No. 195,480 for the esters of orthophosphoric acid, i. e. alkyl, aryl, aralkyl, alkyl-aryl, cycloaliphatic, cycloaromatic and heterocyclic radicals having at least 4 C atoms per substituting group.
- the phosphorus atom may be linked directly to an aliphatic or aromatic radical according to the formula wherein R1 represents an aromatic radical, for instance, phenyl or naphthyl, if desired with a further substituent group such as the amino, alkyl amino, acyl amino, nitro, halogen, alkyl, hydroxyalkyl, and similar radicals.
- R2 represents an aliphatic, straight-chain or branched, or substituted radical.
- the surface active radical may be linked to the P atom by means of a carbon or nitrogen atom.
- salts of the phosphonic acid derivatives viz. alkali metal, ammonium, or amino salts may be used for the production of soap cakes and similar articles.
- secondary esters of orthophosphoric acid having the same or different surface-active groups linked thereto compounds may be prepared from phosphonic acid derivatives in which at least one of the free hydrogen atoms are substituted by a second surface-active group linked ester-fashion, for instance, according to the general formulae, given below:
- R3 represents a surface-active radical similar to R1 or R2, from which it may, however, differ in certain details.
- a molecule of the new derivatives may also contain several phosphonic acid radicals containing one or more surface-active groups, as shown below:
- R1, R2 and R3 represent organic radicals or may be hydrogen.
- At least one of the radicals must be surface-active; n is an integer.
- the phosphonic acid derivatives used in accordance with the invention are in their mode of application similar to the cleansing agents described in my co-pending application Serial No. 195,480. This applies more particularly to their use in admixture with alkali metal salts of fatty acids, sulfonated fatty acids and similar compounds. There is, moreover, a wide range of useful mixtures of surface-active phosphonic acid derivatives with the phosphoric acid esters and their salts as described in my copending application.
- Example 1 To a fatty acid mixture comprising:
- Example 2 25 parts of the sodium salt of the primary ester of orthophosphoric acid with octodecyl alcohol,
- the product thus obtained is a neutral, non-irritating shaving soap of high resistance to hard Water.
- a shaped washing and cleansing agent pressed in the form of a bar consisting essentially of a mixture of about 80 percent of oleic acid and fatty acids from coconut oil and lard and about 20% of stearyl amino phenyl phosphonic acid, said mixture neutralized With an alkali metal hydroxide.
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
SHAPED moan or soar AND PHOSPHONATE Joseph Niisslein, Frankfurtam Main, Germany, assignor to Metallgesellschaft Aktiengesellschaft, Frankfurt am Main, Germany, a corporation of Germany No Drawing. Application November 25", 1952, Serial No. 322,563
Claims priority, application Germany November 30, 1951 2 Claims. (Cl. 252-117) The invention relates to the manufacture of shaped washing agents disclosed in my co-pending patent application Serial Number 195,480 filed November 13, 1950, now abandoned.
In this patent application I have described the prepa-' ration of shaped washing agents based on the use of surface-active derivatives of phosphoric acids and more particularly esters of orthophosphoric acid in the form of their alkali metal salts, ammonium salts and amino salts.
While satisfactorily complying with their action as washing or cleansing agents these compounds have the disadvantage of being split-up when acted upon by strong alkaline agents; this is particularly so when for use together with soaps they are mixed with fatty acids or neutral oils and together saponified with caustic soda solution; as a consequence thereof valuable materials are frequently rendered unusable.
It is the main object of this invention to remedy this situation. In pursuance of this object it has been found that the above mentioned inconvenience of splitting of the phosphoric acid group is avoided and the advantages of obtaining soap preparations capable of a surprising shape stability are secured, if phosphonic acids or their alkali metal-, ammoniumor amino salts are used instead of the corresponding phosphoric acid esters or their salts.
The phosphonic acids may contain the same radicals which are described in the co-pending application Ser. No. 195,480 for the esters of orthophosphoric acid, i. e. alkyl, aryl, aralkyl, alkyl-aryl, cycloaliphatic, cycloaromatic and heterocyclic radicals having at least 4 C atoms per substituting group. The phosphorus atom may be linked directly to an aliphatic or aromatic radical according to the formula wherein R1 represents an aromatic radical, for instance, phenyl or naphthyl, if desired with a further substituent group such as the amino, alkyl amino, acyl amino, nitro, halogen, alkyl, hydroxyalkyl, and similar radicals.
These compounds may also have the formula wherein R2 represents an aliphatic, straight-chain or branched, or substituted radical.
In both cases, whether the radical is R1 or R2 as above defined, the surface active radical may be linked to the P atom by means of a carbon or nitrogen atom.
In the same manner as described in my co-pending application Serial No. 195,480 with regard to the esters of orthophosphoric acid and their derivatives, in the present case salts of the phosphonic acid derivatives, viz. alkali metal, ammonium, or amino salts may be used for the production of soap cakes and similar articles.
nitcd States Patent ice Similarly to the secondary esters of orthophosphoric acid having the same or different surface-active groups linked thereto compounds may be prepared from phosphonic acid derivatives in which at least one of the free hydrogen atoms are substituted by a second surface-active group linked ester-fashion, for instance, according to the general formulae, given below:
wherein R3 represents a surface-active radical similar to R1 or R2, from which it may, however, differ in certain details.
A molecule of the new derivatives may also contain several phosphonic acid radicals containing one or more surface-active groups, as shown below:
wherein R1, R2 and R3 represent organic radicals or may be hydrogen.
At least one of the radicals must be surface-active; n is an integer. These last mentioned compounds as well as their salts are likewise suited for making shaped washing and cleansing agents.
The phosphonic acid derivatives used in accordance with the invention are in their mode of application similar to the cleansing agents described in my co-pending application Serial No. 195,480. This applies more particularly to their use in admixture with alkali metal salts of fatty acids, sulfonated fatty acids and similar compounds. There is, moreover, a wide range of useful mixtures of surface-active phosphonic acid derivatives with the phosphoric acid esters and their salts as described in my copending application.
In the following the invention will be described by a number of examples which are presented by way of illustration and not of limitation and that many modifications of the compounds and their quantities may be made without departing from the spirit of my invention.
Example 1 To a fatty acid mixture comprising:
15% fatty acid from coconut oil 60 fatty acid from lard 5% oleic acid,
20% of a surface-active phosphonic acid derivative are added which was obtained by reacting 1 mol stearyl chloride with 1 mol amino-phenyl phosphonic acid; the mixture is neutralized in a conventional manner with NaOH. After cooling, a soap is obtained which is very hard, can be easily adjusted to neutral reaction and is in this respect superior to ordinary soaps, which it greatly surpasses in stability against the hardeners of the Water.
Example 2 25 parts of the sodium salt of the primary ester of orthophosphoric acid with octodecyl alcohol,
25 parts of the sodium salt of the primary ester of orthophc-sphoric acid with octodecyl tetrapoiyglycol and 40 parts of the sodium salt of the phosphonic acid derivative described in Example 1 are mixed with addition of 10 parts of water, stirred until complete homogenization is obtained, and compressed to bars.
The product thus obtained is a neutral, non-irritating shaving soap of high resistance to hard Water.
Since certain cahnges in carrying out the above process could be made without departing from the scope thereof, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense. a
What I claim is:
1. A shaped washing and cleansing agent pressed in the form of a bar consisting essentially of a mixture of about 80 percent of oleic acid and fatty acids from coconut oil and lard and about 20% of stearyl amino phenyl phosphonic acid, said mixture neutralized With an alkali metal hydroxide.
2. A cleansing agent as in claim 1 wherein said alkali metal hydroxide is sodium hydroxide.
References Cited in the file of this patent UNITED STATES PATENTS Nuesslein May 2, Stevens et a1 Aug. 26, Dickey et a1 Dec. 7, Kosolapoff Mar. 26, Jayne Mar. 13, Kosolapoif Apr. 29,
FOREIGN PATENTS Great Britain Dec. 9,
Claims (1)
1. A SHAPED WASHING AND CLEANING AGENT PRESSED IN THE FORM OF A BAR CONSISTING ESSENTIALLY OF A MIXTURE OF ABOUT 80 PERCENT OF OLEIC ACID AND FATTY ACIDS FROM COCONUT OIL AND LARD AND ABOUT 20% OF STEARYL AMINO PHENYL PHOSPHONIC ACID, SAID MIXTURE NEUTRALIZED WITH AN ALKALI METAL HYDROXIDE.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE289076X | 1949-03-11 | ||
| DE742534X | 1951-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2765279A true US2765279A (en) | 1956-10-02 |
Family
ID=25777271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US322563A Expired - Lifetime US2765279A (en) | 1949-03-11 | 1952-11-25 | Shaped mixture of soap and phosphonate |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2765279A (en) |
| BE (1) | BE499590A (en) |
| CH (2) | CH289076A (en) |
| DE (1) | DE973122C (en) |
| FR (2) | FR1110253A (en) |
| GB (2) | GB717407A (en) |
| NL (2) | NL156859B (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1038692B (en) * | 1956-11-20 | 1958-09-11 | Huels Chemische Werke Ag | Synthetic detergents and cleaning agents containing organic phosphorus compounds |
| DE1152497B (en) * | 1961-10-13 | 1963-08-08 | Henkel & Cie Gmbh | Cleaning and dishwashing products |
| US3149151A (en) * | 1960-03-22 | 1964-09-15 | Henkel & Cie Gmbh | Per-compounds of acylation products of phosphorous acid |
| DE1228365B (en) * | 1961-03-17 | 1966-11-10 | Procter & Gamble | Detergent composition containing tertiary phosphine oxides |
| US3351558A (en) * | 1966-09-06 | 1967-11-07 | Procter & Gamble | Detergent composition containing organic phosphonate corrosion inhibitors |
| US3363032A (en) * | 1964-06-11 | 1968-01-09 | Monsanto Co | Long chain aliphatic benzylphosphonic acids, esters and salts |
| US3368978A (en) * | 1964-12-28 | 1968-02-13 | Monsanto Co | Builder compositions and detergent compositions using same |
| US3404178A (en) * | 1963-03-18 | 1968-10-01 | Procter & Gamble | Substituted methylene diphosphonic acids and their salts |
| US3442938A (en) * | 1967-01-31 | 1969-05-06 | Merck & Co Inc | Prosphanilic acid derivatives |
| US3471406A (en) * | 1965-09-07 | 1969-10-07 | Plains Chem Dev Co | Detergent compositions containing methane tri and tetra phosphonic acid compounds |
| US3471552A (en) * | 1965-08-24 | 1969-10-07 | Plains Chem Dev Co | Aliphatic polyphosphonic acids and derivatives thereof |
| US4175051A (en) * | 1977-02-25 | 1979-11-20 | Kao Soap Co., Ltd. | Scouring pad containing phosphoric acid ester-fatty acid soap mixtures |
| US4235733A (en) * | 1978-07-13 | 1980-11-25 | Kao Soap Co., Ltd. | Antibacterial soap containing trichlorohydroxy diphenyl ether bactericide and an organic phosphoric ester as a stabilizer therefor |
| US4460548A (en) * | 1979-07-09 | 1984-07-17 | Societe Nationale Elf Aquitaine (Production) | Extraction of uranium with diphosphonic compounds |
| US4464346A (en) * | 1979-07-09 | 1984-08-07 | Societe Nationale Elf Aquitaine (Production) | Extraction of uranium with triphosphonic esters |
| US4528110A (en) * | 1982-11-04 | 1985-07-09 | Henkel Kommanditgesellschaft Auf Aktien | Method of using alkyl monophosphoric acids as germicidal agents |
| US4587034A (en) * | 1979-07-09 | 1986-05-06 | Societe Nationale Elf Aquitaine (Production) | Triphosphonic esters |
| US4631142A (en) * | 1979-07-09 | 1986-12-23 | Societe Nationale Elf Aquitaine (Production) | Diphosphonic extractants |
| US5015408A (en) * | 1988-03-19 | 1991-05-14 | Reckitt Gmbh | Denture cleaning tablet containing a bleach activator and an organic phosphonic acid stabilizer |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1260066B (en) * | 1963-07-24 | 1968-02-01 | Henkel & Cie Gmbh | Detergent or auxiliary laundry detergent tablets |
| DE3612701A1 (en) * | 1986-04-15 | 1987-10-22 | Degussa | DETERGENT IN PIECE SHAPE |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1906484A (en) * | 1930-04-08 | 1933-05-02 | Ig Farbenindustrie Ag | Soap preparation |
| GB471875A (en) * | 1934-12-08 | 1937-09-13 | Ig Farbenindustrie Ag | Manufacture of substances having capillary activity |
| US2254124A (en) * | 1939-06-05 | 1941-08-26 | Du Pont | Organic compound of quinquevalent phosphorus |
| US2336230A (en) * | 1941-08-15 | 1943-12-07 | Eastman Kodak Co | Surface-active agent |
| US2397422A (en) * | 1945-03-24 | 1946-03-26 | Monsanto Chemicals | Esters of paraffin phosphonic acids |
| US2545357A (en) * | 1946-06-04 | 1951-03-13 | American Cyanamid Co | Detergent composition and method of preparing same |
| US2594454A (en) * | 1946-05-31 | 1952-04-29 | Monsanto Chemicals | Organic phosphorus acids and esters |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE605973C (en) * | 1930-11-30 | 1934-11-22 | I G Farbenindustrie Akt Ges | Process for the production of ethers from hydroxyl-containing organic compounds and ethylene oxide |
| NL39171C (en) * | 1934-01-24 | |||
| US2169829A (en) * | 1937-06-09 | 1939-08-15 | William G Beckers | Detergent composition |
-
1950
- 1950-03-17 DE DEM2368A patent/DE973122C/en not_active Expired
- 1950-10-17 GB GB25309/50A patent/GB717407A/en not_active Expired
- 1950-10-18 FR FR1110253D patent/FR1110253A/en not_active Expired
- 1950-10-26 NL NL156859A patent/NL156859B/xx unknown
- 1950-10-30 CH CH289076D patent/CH289076A/en unknown
- 1950-11-24 BE BE499590D patent/BE499590A/xx unknown
-
1952
- 1952-11-14 NL NL173813A patent/NL173813B/xx unknown
- 1952-11-25 US US322563A patent/US2765279A/en not_active Expired - Lifetime
- 1952-11-25 FR FR66569D patent/FR66569E/en not_active Expired
- 1952-11-26 GB GB29985/52A patent/GB742534A/en not_active Expired
- 1952-11-27 CH CH295584D patent/CH295584A/en unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1906484A (en) * | 1930-04-08 | 1933-05-02 | Ig Farbenindustrie Ag | Soap preparation |
| GB471875A (en) * | 1934-12-08 | 1937-09-13 | Ig Farbenindustrie Ag | Manufacture of substances having capillary activity |
| US2254124A (en) * | 1939-06-05 | 1941-08-26 | Du Pont | Organic compound of quinquevalent phosphorus |
| US2336230A (en) * | 1941-08-15 | 1943-12-07 | Eastman Kodak Co | Surface-active agent |
| US2397422A (en) * | 1945-03-24 | 1946-03-26 | Monsanto Chemicals | Esters of paraffin phosphonic acids |
| US2594454A (en) * | 1946-05-31 | 1952-04-29 | Monsanto Chemicals | Organic phosphorus acids and esters |
| US2545357A (en) * | 1946-06-04 | 1951-03-13 | American Cyanamid Co | Detergent composition and method of preparing same |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1038692B (en) * | 1956-11-20 | 1958-09-11 | Huels Chemische Werke Ag | Synthetic detergents and cleaning agents containing organic phosphorus compounds |
| US3149151A (en) * | 1960-03-22 | 1964-09-15 | Henkel & Cie Gmbh | Per-compounds of acylation products of phosphorous acid |
| DE1228365B (en) * | 1961-03-17 | 1966-11-10 | Procter & Gamble | Detergent composition containing tertiary phosphine oxides |
| DE1152497B (en) * | 1961-10-13 | 1963-08-08 | Henkel & Cie Gmbh | Cleaning and dishwashing products |
| US3404178A (en) * | 1963-03-18 | 1968-10-01 | Procter & Gamble | Substituted methylene diphosphonic acids and their salts |
| US3422021A (en) * | 1963-03-18 | 1969-01-14 | Procter & Gamble | Detergent composition |
| US3363032A (en) * | 1964-06-11 | 1968-01-09 | Monsanto Co | Long chain aliphatic benzylphosphonic acids, esters and salts |
| US3368978A (en) * | 1964-12-28 | 1968-02-13 | Monsanto Co | Builder compositions and detergent compositions using same |
| US3471552A (en) * | 1965-08-24 | 1969-10-07 | Plains Chem Dev Co | Aliphatic polyphosphonic acids and derivatives thereof |
| US3471406A (en) * | 1965-09-07 | 1969-10-07 | Plains Chem Dev Co | Detergent compositions containing methane tri and tetra phosphonic acid compounds |
| US3351558A (en) * | 1966-09-06 | 1967-11-07 | Procter & Gamble | Detergent composition containing organic phosphonate corrosion inhibitors |
| US3442938A (en) * | 1967-01-31 | 1969-05-06 | Merck & Co Inc | Prosphanilic acid derivatives |
| US4175051A (en) * | 1977-02-25 | 1979-11-20 | Kao Soap Co., Ltd. | Scouring pad containing phosphoric acid ester-fatty acid soap mixtures |
| US4235733A (en) * | 1978-07-13 | 1980-11-25 | Kao Soap Co., Ltd. | Antibacterial soap containing trichlorohydroxy diphenyl ether bactericide and an organic phosphoric ester as a stabilizer therefor |
| US4460548A (en) * | 1979-07-09 | 1984-07-17 | Societe Nationale Elf Aquitaine (Production) | Extraction of uranium with diphosphonic compounds |
| US4464346A (en) * | 1979-07-09 | 1984-08-07 | Societe Nationale Elf Aquitaine (Production) | Extraction of uranium with triphosphonic esters |
| US4587034A (en) * | 1979-07-09 | 1986-05-06 | Societe Nationale Elf Aquitaine (Production) | Triphosphonic esters |
| US4631142A (en) * | 1979-07-09 | 1986-12-23 | Societe Nationale Elf Aquitaine (Production) | Diphosphonic extractants |
| US4528110A (en) * | 1982-11-04 | 1985-07-09 | Henkel Kommanditgesellschaft Auf Aktien | Method of using alkyl monophosphoric acids as germicidal agents |
| US5015408A (en) * | 1988-03-19 | 1991-05-14 | Reckitt Gmbh | Denture cleaning tablet containing a bleach activator and an organic phosphonic acid stabilizer |
Also Published As
| Publication number | Publication date |
|---|---|
| GB742534A (en) | 1955-12-30 |
| CH295584A (en) | 1953-12-31 |
| NL156859B (en) | 1953-11-16 |
| FR66569E (en) | 1957-04-16 |
| CH289076A (en) | 1953-02-28 |
| DE973122C (en) | 1959-12-03 |
| NL173813B (en) | 1954-11-15 |
| GB717407A (en) | 1954-10-27 |
| BE499590A (en) | 1953-03-16 |
| FR1110253A (en) | 1956-02-10 |
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