US3223718A - Fatty acid-hydroxyethyl-quaternary ammonium compounds and preparation thereof - Google Patents
Fatty acid-hydroxyethyl-quaternary ammonium compounds and preparation thereof Download PDFInfo
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- US3223718A US3223718A US204052A US20405262A US3223718A US 3223718 A US3223718 A US 3223718A US 204052 A US204052 A US 204052A US 20405262 A US20405262 A US 20405262A US 3223718 A US3223718 A US 3223718A
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- 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
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
Definitions
- Another object of this invention is to provide new compositions of matter useful as textile softeners for laundering purposes which do not cause darkening of fabrics during ironing.
- a further object of this invention is to provide new compositions of matter useful as textile softeners for laundering which produce a soft and pleasant feel of the fabric to the touch after being treated with such new compositions of matter.
- a still further object of this invention is to provide compositions of matter suitable as textile softeners in laundering which are easy to handle in powder form.
- a still further object of this invention is to provide compositions of matter suitable as textile softeners in laundering which can be prepared from readily available and relatively inexpensive raw materials.
- compositions of matter are generally prepared by starting with a fatty tertiary amine salt of a fatty acid such as stearic, palmitic or hydrogenated tallow fatty acid and treating the fatty tertiary amine salt with ethylene oxide to produce a quaternary ammonium compound having two fatty chains.
- a fatty acid such as stearic, palmitic or hydrogenated tallow fatty acid
- ethylene oxide such as stearic, palmitic or hydrogenated tallow fatty acid
- Example I 1154 grams (3.9.1 moles) of stearyl dimethyl amine and 1M2 grams (3. 9 1 moles) of stearic acid were loaded into a 2 gallon stainless steel autoclave.
- the autoclave was heated with steam and nitrogen gas was introduced inside the autoclave. When the temperature reached 60 C., heating was discontinued. After 50 minutes, the stearic acid was melted and the agitator turned on. The outlet valve was closed of the autoclave and nitrogen sparging was discontinued.
- the internal pressure at this stage was 2 pounds per square inch.
- the pH of a sample taken from the batch and tested at a concentration of 3% by weight in 50% isopropanol showed 6.85. 177 grams (4.023 moles) ethylene oxide was added from a small scale tank. At this stage the initial temperature was 63 C. The internal pressure rose to 45 pounds per square inch.
- the internal pressure was 23 pounds per square inch.
- the reaction was then continued for another minutes at the end of which time, a test of the percentage of free fatty acid showed only 74%.
- the reaction was continued for an additional 50 minutes, at a pressure of 18 pounds per square inch and a temperature of 77 C.
- the vacuum was turned on for 25 minutes reaching a maximum of 24 inches of mercury. The batch was then steam sparged until the vacuum dropped to 10 inches of mercury and then the vacuum was reduced to zero with nitrogen gas.
- the resulting product stearyl dimethyl hydroxyethyl ammonium stearate, was a cream colored solid flake with a melting point of 64 C.
- the yield was 2293 grams, which was 98.3% of the theoretical yield of 2333 grams.
- the final pH of the product at a concentration of 3% by weight in 50% isopropanol solution was 8.6.
- Example II The same general procedure of Example I was used, except that instead of stearyl dimethyl amine, 2254 grams (7.38) moles of dimethyl hydrogenated tallow amine was the starting material and along with 1978 grams (7.38 moles) of stearic acid were loaded into the autoclave of Example I. 330 grams (7.50 moles) of ethylene oxide were reacted in the same manner as in Example I with the mixture of dimethyl tallow amine and stearic acid. The resulting product, dimethyl (hydrogenated tallow) hydroxyethyl ammonium stearate, was a white solid flake, melting at 59 C. and a yield of 99% of the theoretical was obtained.
- Example III Again, the same general procedure was used as in Example I except that .1767 grams (5.8 1 moles) of dimethyl palmityl amine and 1557 grams (5.81 moles) of stearic acid were loaded in the autoclave of Example I. This mixture was reacted with 259 grams (5.88 moles) of ethylene oxide. The resulting product, dimethyl palmityl hydroxyethyl ammonium stearate, was a white solid flake having properties similar to those in Examples I and II and-with a melting point of 57 C.
- Example IV The same procedure as in Example I was used, except that 1160 grams (2.00 moles) of methyl dihydrogenated tallow amine and 218.3 grams (2.02 moles) of 70% by weight hydroxyacetic acid were loaded in the autoclave of Example I. This mixture was reacted with 1.27 grams (2.89 moles) of ethylene oxide and with 98 grams of isopropanol for a solvent. The excess ethylene oxide was removed when the reaction was completed by purging with nitrogen gas.
- the resulting product methyl di(hydrogenated tallow) hydroxyethyl ammonium hydroxy acetate, was an amber paste containing 92.8% of an active quaternary ammonium compound which exhibited similar textile softening properties as the products of the preceding example.
- Example V The same general procedure was used as in Example I except that 1030 grams (1.776 moles) of methyl dihydrogenated tallow amine and grams (2.00 moles) of glacial acetic acid were loaded in the autoclave of Example I. This mixture was reacted with 144 grams (3.27 moles) of ethylene oxide. After the reaction was completed excess ethylene oxide was removed by sparging with nitrogen gas. The resulting product, methyl di(hydrogenated tallow) hydroxyethyl ammonium acetate, was an amber solid having a melting point of 59 C. and exhibiting textile softening properties similar to the products of the preceding examples.
- the textile softening properties of the product of Example I were tested by making up a formulation of the product by first dissolving 5.50% of the product of Example I by weight in a dispersion, containing 0.30% by weight of hydroxyethyl cellulose, available commercially under the designation of Natrosol 250 HR, in 93.15% soft Water at 75 C., to which was added 0.85% by Weight of a nonionic emulsifier of the polyoxypropylenepolyoxyethylene type available commercially under the designation of Pluronic L64.
- the pH of the emulsion was adjusted to 5.0 with 0.20% hydroxyacetic acid.
- This emulsion had a viscosity, using a Brookfield viscometer, of 420 centipoises at 25 C.
- Samples of the emulsion were stored in a refrigerator, then kept overnight in an oven heated to 110 F. The samples were then rotated for 12 hour periods alternately for one week, first in the refrigerator, then kept at room temperature and then placed in a 110 oven. No separation was noted in any of the samples.
- This resulting formulation was tested for textile softening properties by adding 50 cc. to the final rinse in a Kenmore home washing machine containing a normal load of 8-9 pounds of clothes. These clothes had been previously laundered with a commercial anionic household laundry detergent advertised under the trademark Tide. After the final rinse and drying of the clothes, the clothes were examined for feel and softness. The clothes had an exceptional smoothness and softness as compared to other available textile softeners on the market. This washing and softening procedure was repeated times without any noticeable yellowing or darkening upon ironing of the clothes.
- Another formulation was made up in a similar manner as before, containing 3.00% by weight of the product of Example III dissolved in a dispersion of 0.20% by weight of hydroxyethyl cellulose, available commercially under the designation of Natrosol 250 HR, in 96.15% soft water at 70 C.
- a nonionic emulsifier the same one as in the preceding formulation, was added in the amount of .50% by weight to the resulting mixture, and the pH was adjusted to 5.0 with .15% hydroxyacetic acid.
- a viscosity of 270 centipoises at C. was obtained with a Brookfield Viscometer on the finished product. Subjecting samples of the emulsion for 12 hour periods for one week in succession to the refrigerator, the 110 F. oven and at room temperature did not cause any separation of the samples.
- compositions defined above may be more conveniently and accurately expressed by the following formula:
- R is an acyclic hydrocarbyl radical having I from 16 to 22 carbon atoms
- R is selected from the group consisting of an acyclic hydrocarbyl radical having from 16 to 22 carbon atoms and a methyl radical
- R is selected from the group consisting of alkyl and hydroxy alkyl radicals having from 1 to 21 carbon atoms, and two of the radicals of the R R and R are long chain.
- compositions as illustrated above for preparation of the product of Example I, are made by reacting an aliphatic carboxylic or hydroxy carboxylic acid R COO'H in which R has the values given in the above formula with a tertiary amine having the formula R (R )N-CH in which R and R are defined as above to form a neutral amine salt of the acid. Thereafter, the amine salt is reacted with ethylene oxide in approximately equal molar quantities to alkylate the neutral amine salt and form a quaternary ammonium compound by introduction of the hydroxyethyl group as shown above.
- R is an acyclic hydrocarbyl radical having from 16 to 22 carbon atoms
- R is selected from the group consisting of an acyclic hydrocarbyl radical having from 16 to 22 carbon atoms and a methyl radical
- R is selected from the group consisting of alkyl and hydroxy .alkyl radicals having from 1 to 21 carbon atoms, and two of the radicals R R and R are long chain.
- a quaternary compound which is stearyl dimethyl hydroxyethyl ammonium stearate.
- a quaternary compound which is dimethyl (hydrogenated tallow) hydroxyethyl ammonium stearate.
- a quaternary ammonium compound which is dimethyl palmityl hydroxyethyl ammonium stearate.
- a quaternary compound which is methyl di (hydrogenated tallow) hydroxyethyl ammonium hydroxy acetate.
- a quaternary compound which is methyl di (hydrogenated tallow) hydroxyethyl ammonium acetate.
- a method for preparing quaternary compounds ate said amine by introduction of a hydroxyethyl which comprises reacting group, thereby forming said quaternary compound.
- R is selected from a group consisting of an acyclic hydrocarbyl radical l0 having from 16 to 22 carbon atoms and a methyl CHARLES PARKER Pr'mary Exammer' radical, to produce a neutral salt of said amine, and HORWITZ, Examinerreacting the neutral salt with ethylene oxide to alkyl-
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- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3223,718 FATTY ACID-HYDRbXYETI-IYL-QUATERNARY AMMONIUM COMPOUNDS AND PREPARA- 7 Claims. (Cl. 260-404) This invention relates to improvements in textile softeners used in the final rinse of laundering cycles, and to methods of preparation of such textile softeners.
Hitherto, commercially available textile softeners, when used on white fabrics repeatedly caused yellowing of the fabrics. Further, such available textile softeners frequently darken the cloth during ironing.
It is, therefore, the object of this invention to provide textile softeners for laundering purposes which do not cause yellowing of fabrics upon repeated washings.
Another object of this invention is to provide new compositions of matter useful as textile softeners for laundering purposes which do not cause darkening of fabrics during ironing.
A further object of this invention is to provide new compositions of matter useful as textile softeners for laundering which produce a soft and pleasant feel of the fabric to the touch after being treated with such new compositions of matter.
A still further object of this invention is to provide compositions of matter suitable as textile softeners in laundering which are easy to handle in powder form.
A still further object of this invention is to provide compositions of matter suitable as textile softeners in laundering which can be prepared from readily available and relatively inexpensive raw materials.
These and other objects will be more readily understood by the following discussion.
These new compositions of matter are generally prepared by starting with a fatty tertiary amine salt of a fatty acid such as stearic, palmitic or hydrogenated tallow fatty acid and treating the fatty tertiary amine salt with ethylene oxide to produce a quaternary ammonium compound having two fatty chains. The products resulting from these methods of preparation have unusual properties as textile softeners in laundering. The following are illustrative examples of these new compositions of matter and methods of preparation:
Example I 1154 grams (3.9.1 moles) of stearyl dimethyl amine and 1M2 grams (3. 9 1 moles) of stearic acid were loaded into a 2 gallon stainless steel autoclave. The autoclave was heated with steam and nitrogen gas was introduced inside the autoclave. When the temperature reached 60 C., heating was discontinued. After 50 minutes, the stearic acid was melted and the agitator turned on. The outlet valve was closed of the autoclave and nitrogen sparging was discontinued. The internal pressure at this stage was 2 pounds per square inch. The pH of a sample taken from the batch and tested at a concentration of 3% by weight in 50% isopropanol showed 6.85. 177 grams (4.023 moles) ethylene oxide was added from a small scale tank. At this stage the initial temperature was 63 C. The internal pressure rose to 45 pounds per square inch.
After the reaction proceeded for 1 hour and 9 minutes the temperature rose to 75 C. and the internal pressure dropped to 27 pounds per square inch. The temperature was maintained at 7'278 C. for another 54 minutes by running steam through the jacket of the autoclave. At
this stage, the internal pressure was 23 pounds per square inch. The reaction was then continued for another minutes at the end of which time, a test of the percentage of free fatty acid showed only 74%. The reaction was continued for an additional 50 minutes, at a pressure of 18 pounds per square inch and a temperature of 77 C.
To remove any traces of unreacted ethylene oxide, the vacuum was turned on for 25 minutes reaching a maximum of 24 inches of mercury. The batch was then steam sparged until the vacuum dropped to 10 inches of mercury and then the vacuum was reduced to zero with nitrogen gas.
The resulting product, stearyl dimethyl hydroxyethyl ammonium stearate, was a cream colored solid flake with a melting point of 64 C. The yield was 2293 grams, which was 98.3% of the theoretical yield of 2333 grams.
The final pH of the product at a concentration of 3% by weight in 50% isopropanol solution was 8.6.
Example II The same general procedure of Example I was used, except that instead of stearyl dimethyl amine, 2254 grams (7.38) moles of dimethyl hydrogenated tallow amine was the starting material and along with 1978 grams (7.38 moles) of stearic acid were loaded into the autoclave of Example I. 330 grams (7.50 moles) of ethylene oxide were reacted in the same manner as in Example I with the mixture of dimethyl tallow amine and stearic acid. The resulting product, dimethyl (hydrogenated tallow) hydroxyethyl ammonium stearate, was a white solid flake, melting at 59 C. and a yield of 99% of the theoretical was obtained.
Example III Again, the same general procedure was used as in Example I except that .1767 grams (5.8 1 moles) of dimethyl palmityl amine and 1557 grams (5.81 moles) of stearic acid were loaded in the autoclave of Example I. This mixture was reacted with 259 grams (5.88 moles) of ethylene oxide. The resulting product, dimethyl palmityl hydroxyethyl ammonium stearate, was a white solid flake having properties similar to those in Examples I and II and-with a melting point of 57 C.
Example IV The same procedure as in Example I was used, except that 1160 grams (2.00 moles) of methyl dihydrogenated tallow amine and 218.3 grams (2.02 moles) of 70% by weight hydroxyacetic acid were loaded in the autoclave of Example I. This mixture was reacted with 1.27 grams (2.89 moles) of ethylene oxide and with 98 grams of isopropanol for a solvent. The excess ethylene oxide was removed when the reaction was completed by purging with nitrogen gas. The resulting product, methyl di(hydrogenated tallow) hydroxyethyl ammonium hydroxy acetate, was an amber paste containing 92.8% of an active quaternary ammonium compound which exhibited similar textile softening properties as the products of the preceding example.
Example V The same general procedure was used as in Example I except that 1030 grams (1.776 moles) of methyl dihydrogenated tallow amine and grams (2.00 moles) of glacial acetic acid were loaded in the autoclave of Example I. This mixture was reacted with 144 grams (3.27 moles) of ethylene oxide. After the reaction was completed excess ethylene oxide was removed by sparging with nitrogen gas. The resulting product, methyl di(hydrogenated tallow) hydroxyethyl ammonium acetate, was an amber solid having a melting point of 59 C. and exhibiting textile softening properties similar to the products of the preceding examples.
The textile softening properties of the product of Example I were tested by making up a formulation of the product by first dissolving 5.50% of the product of Example I by weight in a dispersion, containing 0.30% by weight of hydroxyethyl cellulose, available commercially under the designation of Natrosol 250 HR, in 93.15% soft Water at 75 C., to which was added 0.85% by Weight of a nonionic emulsifier of the polyoxypropylenepolyoxyethylene type available commercially under the designation of Pluronic L64.
The pH of the emulsion was adjusted to 5.0 with 0.20% hydroxyacetic acid. This emulsion had a viscosity, using a Brookfield viscometer, of 420 centipoises at 25 C. Samples of the emulsion were stored in a refrigerator, then kept overnight in an oven heated to 110 F. The samples were then rotated for 12 hour periods alternately for one week, first in the refrigerator, then kept at room temperature and then placed in a 110 oven. No separation was noted in any of the samples.
This resulting formulation was tested for textile softening properties by adding 50 cc. to the final rinse in a Kenmore home washing machine containing a normal load of 8-9 pounds of clothes. These clothes had been previously laundered with a commercial anionic household laundry detergent advertised under the trademark Tide. After the final rinse and drying of the clothes, the clothes were examined for feel and softness. The clothes had an exceptional smoothness and softness as compared to other available textile softeners on the market. This washing and softening procedure was repeated times without any noticeable yellowing or darkening upon ironing of the clothes.
Another formulation was made up in a similar manner as before, containing 3.00% by weight of the product of Example III dissolved in a dispersion of 0.20% by weight of hydroxyethyl cellulose, available commercially under the designation of Natrosol 250 HR, in 96.15% soft water at 70 C. A nonionic emulsifier, the same one as in the preceding formulation, was added in the amount of .50% by weight to the resulting mixture, and the pH was adjusted to 5.0 with .15% hydroxyacetic acid. A viscosity of 270 centipoises at C. was obtained with a Brookfield Viscometer on the finished product. Subjecting samples of the emulsion for 12 hour periods for one week in succession to the refrigerator, the 110 F. oven and at room temperature did not cause any separation of the samples.
4 ounces of this formulation was added in a test to the final rinse as before in a home washing machine under the same conditions. Clothes laundered and treated with this formulation repeatedly for 20 times exhibited no yellowing or darkening upon ironing. The treated clothes had an unusual smoothness and softness to the touch as compared to clothes treated with commercially available textile softener-s.
The structural formula of these new compositions of matter may be illustrated as follows, with reference to the preparation of the product of Example I:
methyl amine UHF-CH2 Neutral salt Ethylene Oxide (3 Ha C13H37NCH2CH:OH O0O-C|7H35 47 Ha Stearyl dimethyl hydroxyethyl stearate ammonium Any normal aliphatic carboxylic acid or hydroxylated carboxylic acid having from 2 to 22 carbon atoms may be used in place of stearic acid as shown above. Further, any normal aliphatic radical having from 16 to 22 carbon atoms could be used in place of the palmityl or stearyl radical of the amine. Also, any normal aliphatic radical having from 16 to 22 carbon atoms may be used to replace both the stearyl radical and one of the methyl groups of the tertiary amine. The term normal aliphatic radical as used herein means an acyclic hydrocarbyl radical.
The compositions defined above may be more conveniently and accurately expressed by the following formula:
in which R is an acyclic hydrocarbyl radical having I from 16 to 22 carbon atoms, R is selected from the group consisting of an acyclic hydrocarbyl radical having from 16 to 22 carbon atoms and a methyl radical, and R is selected from the group consisting of alkyl and hydroxy alkyl radicals having from 1 to 21 carbon atoms, and two of the radicals of the R R and R are long chain. These compositions, as illustrated above for preparation of the product of Example I, are made by reacting an aliphatic carboxylic or hydroxy carboxylic acid R COO'H in which R has the values given in the above formula with a tertiary amine having the formula R (R )N-CH in which R and R are defined as above to form a neutral amine salt of the acid. Thereafter, the amine salt is reacted with ethylene oxide in approximately equal molar quantities to alkylate the neutral amine salt and form a quaternary ammonium compound by introduction of the hydroxyethyl group as shown above.
While we have described preferred examples of this invention as to compositions of matter and methods of preparation it is understood that the scope of the invention is not to be limited thereby but numerous variations are possible without departing from the spirit of the invention as claimed hereinafter.
We claim:
1. A quaternary compound having the following general formula:
in which R is an acyclic hydrocarbyl radical having from 16 to 22 carbon atoms, R is selected from the group consisting of an acyclic hydrocarbyl radical having from 16 to 22 carbon atoms and a methyl radical, and R is selected from the group consisting of alkyl and hydroxy .alkyl radicals having from 1 to 21 carbon atoms, and two of the radicals R R and R are long chain.
2. A quaternary compound which is stearyl dimethyl hydroxyethyl ammonium stearate.
3. A quaternary compound which is dimethyl (hydrogenated tallow) hydroxyethyl ammonium stearate.
4. A quaternary ammonium compound which is dimethyl palmityl hydroxyethyl ammonium stearate.
5. A quaternary compound which is methyl di (hydrogenated tallow) hydroxyethyl ammonium hydroxy acetate.
6. A quaternary compound which is methyl di (hydrogenated tallow) hydroxyethyl ammonium acetate.
5 6 7. A method for preparing quaternary compounds ate said amine by introduction of a hydroxyethyl which comprises reacting group, thereby forming said quaternary compound.
(1) a carboxylic acid having the formula R COOH in which R is selected from the group consisting of References Cited y the Examine! alkyl and hydroxy alkyl radicals having from 1 to UNITED STATES PATENTS 21 carbon atoms with (2) a tertiary amine having the formula R (R )N--CH g g i in which R is an acyclic hydrocarbyl radical having c ac e a 2,214,352 9/1940 Schoeller et a1. 260-404 from 16 to 22 carbon atoms and R is selected from a group consisting of an acyclic hydrocarbyl radical l0 having from 16 to 22 carbon atoms and a methyl CHARLES PARKER Pr'mary Exammer' radical, to produce a neutral salt of said amine, and HORWITZ, Examinerreacting the neutral salt with ethylene oxide to alkyl-
Claims (1)
1. A QUATERNARY COMPOUND HAVING THE FOLLOWING GENERAL FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US204052A US3223718A (en) | 1962-06-21 | 1962-06-21 | Fatty acid-hydroxyethyl-quaternary ammonium compounds and preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US204052A US3223718A (en) | 1962-06-21 | 1962-06-21 | Fatty acid-hydroxyethyl-quaternary ammonium compounds and preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3223718A true US3223718A (en) | 1965-12-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US204052A Expired - Lifetime US3223718A (en) | 1962-06-21 | 1962-06-21 | Fatty acid-hydroxyethyl-quaternary ammonium compounds and preparation thereof |
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| Country | Link |
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| US (1) | US3223718A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3915867A (en) * | 1973-04-24 | 1975-10-28 | Stepan Chemical Co | Domestic laundry fabric softener |
| FR2306731A1 (en) * | 1975-04-07 | 1976-11-05 | Ici Ltd | Emulsifiers decomposing on change of acidity in aq. emulsions - for removing mineral or vegetable oils from surfaces, and for use in metal-working oils |
| US4186255A (en) * | 1978-03-13 | 1980-01-29 | Texaco Development Corporation | Bis-quaternary ammonium salts as polyisocyanurate catalysts |
| US4392965A (en) * | 1981-11-12 | 1983-07-12 | Woodward Fred E | Laundry softener antistatic composition |
| EP0107088A1 (en) * | 1982-09-30 | 1984-05-02 | Ppg Industries, Inc. | Novel pigment grinding vehicle |
| EP0146097A2 (en) * | 1983-12-17 | 1985-06-26 | Hoechst Aktiengesellschaft | Oxyalkylated quaternary ammonium compounds, their preparation and their use as drag reducing agents |
| US4530945A (en) * | 1982-09-30 | 1985-07-23 | Ppg Industries, Inc. | Pigment grinding vehicle |
| WO1989009204A1 (en) * | 1988-04-02 | 1989-10-05 | Henkel Kommanditgesellschaft Auf Aktien | Quaternary ammonium compounds |
| US5576459A (en) * | 1994-02-02 | 1996-11-19 | Sachem, Inc. | Quaternary nitrogen or phosphorus chirates |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2129264A (en) * | 1935-03-29 | 1938-09-06 | Du Pont | Nitrogen-containing organic compounds |
| US2143388A (en) * | 1934-11-30 | 1939-01-10 | Ig Farbenindustrie Ag | Manufacture of hydroxyalkylated nitrogen bases |
| US2214352A (en) * | 1935-06-22 | 1940-09-10 | Gen Aniline & Film Corp | Process for the production of condensation products containing onium groups |
-
1962
- 1962-06-21 US US204052A patent/US3223718A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2143388A (en) * | 1934-11-30 | 1939-01-10 | Ig Farbenindustrie Ag | Manufacture of hydroxyalkylated nitrogen bases |
| US2129264A (en) * | 1935-03-29 | 1938-09-06 | Du Pont | Nitrogen-containing organic compounds |
| US2214352A (en) * | 1935-06-22 | 1940-09-10 | Gen Aniline & Film Corp | Process for the production of condensation products containing onium groups |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3915867A (en) * | 1973-04-24 | 1975-10-28 | Stepan Chemical Co | Domestic laundry fabric softener |
| FR2306731A1 (en) * | 1975-04-07 | 1976-11-05 | Ici Ltd | Emulsifiers decomposing on change of acidity in aq. emulsions - for removing mineral or vegetable oils from surfaces, and for use in metal-working oils |
| US4186255A (en) * | 1978-03-13 | 1980-01-29 | Texaco Development Corporation | Bis-quaternary ammonium salts as polyisocyanurate catalysts |
| US4392965A (en) * | 1981-11-12 | 1983-07-12 | Woodward Fred E | Laundry softener antistatic composition |
| JPH0256378B2 (en) * | 1982-09-30 | 1990-11-30 | Ppg Industries Inc | |
| EP0107088A1 (en) * | 1982-09-30 | 1984-05-02 | Ppg Industries, Inc. | Novel pigment grinding vehicle |
| JPS5991164A (en) * | 1982-09-30 | 1984-05-25 | ピーピージー・インダストリーズ・インコーポレイテッド | Quaternary ammonium group containing substance |
| US4530945A (en) * | 1982-09-30 | 1985-07-23 | Ppg Industries, Inc. | Pigment grinding vehicle |
| EP0146097A2 (en) * | 1983-12-17 | 1985-06-26 | Hoechst Aktiengesellschaft | Oxyalkylated quaternary ammonium compounds, their preparation and their use as drag reducing agents |
| EP0146097A3 (en) * | 1983-12-17 | 1986-05-14 | Hoechst Aktiengesellschaft | Oxyalkylated quaternary ammonium compounds, their preparation and their use as drag reducing agents |
| WO1989009204A1 (en) * | 1988-04-02 | 1989-10-05 | Henkel Kommanditgesellschaft Auf Aktien | Quaternary ammonium compounds |
| EP0336267A2 (en) * | 1988-04-02 | 1989-10-11 | Henkel Kommanditgesellschaft auf Aktien | Quaternary ammonium compounds |
| EP0336267A3 (en) * | 1988-04-02 | 1989-10-25 | Henkel Kommanditgesellschaft auf Aktien | Quaternary ammonium compounds |
| US5576459A (en) * | 1994-02-02 | 1996-11-19 | Sachem, Inc. | Quaternary nitrogen or phosphorus chirates |
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