US3872138A - Process for the preparation of quaternary ammonium salts - Google Patents
Process for the preparation of quaternary ammonium salts Download PDFInfo
- Publication number
- US3872138A US3872138A US304128A US30412872A US3872138A US 3872138 A US3872138 A US 3872138A US 304128 A US304128 A US 304128A US 30412872 A US30412872 A US 30412872A US 3872138 A US3872138 A US 3872138A
- Authority
- US
- United States
- Prior art keywords
- acid
- alkyl
- quaternary ammonium
- carboxylic acid
- carbon atoms
- 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
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title description 5
- -1 alkenyl tertiary amine Chemical class 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000005639 Lauric acid Substances 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 3
- GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 claims description 3
- BUHHOHWMNZQMTA-UHFFFAOYSA-N n,n-dioctadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC BUHHOHWMNZQMTA-UHFFFAOYSA-N 0.000 claims description 3
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 3
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-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
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 claims description 2
- 229950010007 dimantine Drugs 0.000 claims description 2
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 10
- 125000002091 cationic group Chemical group 0.000 abstract description 9
- 150000002148 esters Chemical class 0.000 abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- JWAJUTZQGZBKFS-UHFFFAOYSA-N n,n-diethylprop-2-en-1-amine Chemical compound CCN(CC)CC=C JWAJUTZQGZBKFS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 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
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Definitions
- ABSTRACT A quaternary ammonium salt containing an ester linkage in the cationic moiety is prepared by reacting an epihalohydrin with a salt of an alkyl or alkenyl tertiary amine and a carboxylic acid.
- a conventional method of preparing quaternary ammonium salts comprises reacting an alkyl amine with an alkyl halide. Re cently, methods using an epihalohydrin are adopted sometimes. The most typical method using an epihalohydrin comprises reacting an epihalohydrin directly with a tertiary amine. However, in this method it is difficult to prepare quaternary ammonium salts having a complicated structure. It is especially difficult to introduce a reactive group into the cationic moiety.
- This invention is based on the discovery of a process for preparing quaternary ammonium salts having a reactive ester group in the cationic moiety, which are useful as textile-treating agents.
- the products obtained by the process of this invention are useful as textilesoftening agents having an antistatic property, or as level-dycing or dyeing-retarding agents of the decomposition type.
- this invention is to provide a process for the preparation of quaternary ammonium salts having an ester linkage in the cationic moiety, characterized by reacting an epihalohydrin with a salt of an alkyl or alkenyl tertiary amine and a carboxylic acid.
- the salt of an alkyl tertiary amine and a carboxylic acid may be prepared in an ordinary solvent such as benzene and lower aliphatic alcohols by a customary method.
- the kind ofthe epihalohydrin is appropriately chosen depending on whether the intended quaternary ammonium salt is a chloride or bromide.
- Quaternary ammonium salts to be obtained by the process of the present invention are represented by a chemical formula as follows:
- R is an alkyl, alkenyl or cycloalkyl radical of from 1 to 17 carbon atoms; in which N is a quaternary nitrogen atom; in which X is halogen, such as chlorine, bromine and fluorine; and in which each of R,, R and R is an alkyl or alkenyl radical having 1 to 18 carbon atoms.
- alkyl or alkenyl tertiary amines which may be quaternized in the practice ofthe present invention are as follows:
- Epihalohydrin for example, epichlorohydrin or epibromohydrin.
- carboxylic acids which may be used in the practice of the present invention are as follows:
- Our process involves the preparation of a salt of an alkyl or alkenyl tertiary amine and a carboxylic acid by neutralizing the carboxylic acid with the amine in substantially stoichiometric amounts. Then, the salt is re acted with epihalohydrin.
- the reaction may be carried out at any suitable temperature and pressure, temperatures between 50C and C and pressures at or near atmospheric being suitable. Conveniently, the reaction is carried out in the presence of a solvent such as benzene and a lower aliphatic alcohol, for example, methanol, ethanol, propanol, butanol, pentanol, etc.
- the temperature of the reaction may be very conveniently controlled by conducting the reaction under reflux conditions. We have found that the use of benzene is highly satisfactory.
- Epihalohydrin can be used in a substantially stoichiometric amount, but it may be preferably employed in a slight excess, for example, 20 percent excess over its stoichiometric amount.
- the solvent employed is first distilled off. Purification is largely by way of removal of small quantities of unreacted reactants by any suitable means such as extraction with a suitable solvent, for example, diethyl ether and/or recrystallization from a suitable solvent, for example, acetone and diethyl ether.
- a suitable solvent for example, diethyl ether and/or recrystallization from a suitable solvent, for example, acetone and diethyl ether.
- tertiary amine is selected from the group consisting of trimethylamine, triethylamine, trinormalpropylamine, dimethylethylamine, methyldiethylamine, dimethylallylamine, diethyallylamine, dimethyldodecylamine, dimethyloctadecylamine, trioctylamine, trioctadecylamine and trioleylamine and mixtures thereof and said carboxylic acid is selected from the group consisting of acetic acid, lauric acid, crotonic acid, acrylic acid, methacrylic acid, oleic acid, l-adamantyl carboxylic acid and cyclohexyl carboxylic acid.
- each of R R and R is alkyl having 1 to 18 carbon atoms and R is selected from the group consisting of alkyl having 1 to 17 carbon atoms, alkenyl having from 2 to 17 carbon atoms, adamantyl and cyclohexyl.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46089225A JPS5229292B2 (en:Method) | 1971-11-09 | 1971-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3872138A true US3872138A (en) | 1975-03-18 |
Family
ID=13964777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US304128A Expired - Lifetime US3872138A (en) | 1971-11-09 | 1972-11-06 | Process for the preparation of quaternary ammonium salts |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3872138A (en:Method) |
| JP (1) | JPS5229292B2 (en:Method) |
| GB (1) | GB1390534A (en:Method) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992304A (en) * | 1975-02-10 | 1976-11-16 | Kao Soap Co., Ltd. | Softening agent for a woven fabric |
| US4339391A (en) * | 1979-07-14 | 1982-07-13 | Hoechst Aktiengesellschaft | Quaternary ammonium compounds |
| US4368127A (en) * | 1979-07-02 | 1983-01-11 | Akzona Incorporated | Fabric softening compounds and method |
| US4621141A (en) * | 1984-04-26 | 1986-11-04 | Mobil Oil Corporation | Additives for improving low temperature characteristics of fuels and method for use thereof |
| US4840738A (en) * | 1988-02-25 | 1989-06-20 | The Procter & Gamble Company | Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts |
| US5422021A (en) * | 1989-09-19 | 1995-06-06 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening |
| US5516438A (en) * | 1989-09-19 | 1996-05-14 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening |
| FR2756823A1 (fr) * | 1996-12-11 | 1998-06-12 | Oreal | Procede de preparation de derives ammoniums quaternaires hydroxypropyles a fonction ester d'acide gras |
| EP0918104A1 (en) * | 1997-11-19 | 1999-05-26 | Arizona Chemical Oy | A papermaking process and a cationic chemical |
| US6214325B1 (en) | 1996-12-11 | 2001-04-10 | L'oreal | Hydroxypropyl quaternary ammonium compounds containing an ester function, and cosmetic and dermatological compositions containing them |
| US6521782B1 (en) * | 1999-01-21 | 2003-02-18 | Atofina | Method for making aqueous solutions of unsaturated quaternary ammonium salts |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59184897U (ja) * | 1983-05-27 | 1984-12-08 | 株式会社 タカラ | 走行玩具 |
| IT1249056B (it) * | 1991-05-22 | 1995-02-11 | Donegani Guido Ist | Catalizzatori liquidi per la polimerizzazione rapida di composizioni liquide a base di poliisocianati ed epossidi. |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3272712A (en) * | 1962-10-29 | 1966-09-13 | Oreal | Quaternary ammonium salts of esters of fatty acids and a precursor of amino-2-hydroxy propanol, methods of their preparation and their use |
| US3290304A (en) * | 1961-11-02 | 1966-12-06 | Oreal | Quaternary ammonium compounds, their preparation and their use |
| US3383397A (en) * | 1965-01-14 | 1968-05-14 | Arizona Chem | 3-amino-2-hydroxypropyl esters and methods for preparing the same |
| US3514473A (en) * | 1967-08-02 | 1970-05-26 | Dow Chemical Co | Aminohydroxyalkyl methacrylates |
| US3694393A (en) * | 1969-04-04 | 1972-09-26 | Rohm & Haas | Method of producing paper,and paper obtained |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3397227A (en) * | 1967-11-09 | 1968-08-13 | Shell Oil Co | Ester production |
-
1971
- 1971-11-09 JP JP46089225A patent/JPS5229292B2/ja not_active Expired
-
1972
- 1972-11-06 US US304128A patent/US3872138A/en not_active Expired - Lifetime
- 1972-11-08 GB GB5151572A patent/GB1390534A/en not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3290304A (en) * | 1961-11-02 | 1966-12-06 | Oreal | Quaternary ammonium compounds, their preparation and their use |
| US3272712A (en) * | 1962-10-29 | 1966-09-13 | Oreal | Quaternary ammonium salts of esters of fatty acids and a precursor of amino-2-hydroxy propanol, methods of their preparation and their use |
| US3383397A (en) * | 1965-01-14 | 1968-05-14 | Arizona Chem | 3-amino-2-hydroxypropyl esters and methods for preparing the same |
| US3514473A (en) * | 1967-08-02 | 1970-05-26 | Dow Chemical Co | Aminohydroxyalkyl methacrylates |
| US3694393A (en) * | 1969-04-04 | 1972-09-26 | Rohm & Haas | Method of producing paper,and paper obtained |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992304A (en) * | 1975-02-10 | 1976-11-16 | Kao Soap Co., Ltd. | Softening agent for a woven fabric |
| US4368127A (en) * | 1979-07-02 | 1983-01-11 | Akzona Incorporated | Fabric softening compounds and method |
| US4339391A (en) * | 1979-07-14 | 1982-07-13 | Hoechst Aktiengesellschaft | Quaternary ammonium compounds |
| EP0022562B1 (de) * | 1979-07-14 | 1985-06-19 | Hoechst Aktiengesellschaft | Quaternäre Ammoniumverbindungen, deren Herstellung und deren Verwendung als Wäscheweichspülmittel |
| US4621141A (en) * | 1984-04-26 | 1986-11-04 | Mobil Oil Corporation | Additives for improving low temperature characteristics of fuels and method for use thereof |
| EP0330261A3 (en) * | 1988-02-25 | 1990-12-27 | The Procter & Gamble Company | Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts |
| US4840738A (en) * | 1988-02-25 | 1989-06-20 | The Procter & Gamble Company | Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts |
| US5422021A (en) * | 1989-09-19 | 1995-06-06 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening |
| US5516438A (en) * | 1989-09-19 | 1996-05-14 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening |
| FR2756823A1 (fr) * | 1996-12-11 | 1998-06-12 | Oreal | Procede de preparation de derives ammoniums quaternaires hydroxypropyles a fonction ester d'acide gras |
| EP0847985A1 (fr) * | 1996-12-11 | 1998-06-17 | L'oreal | Procédé de préparation de dérivés ammoniums quaternaires hydroxypropyles à fonction ester d'acide gras |
| US6046344A (en) * | 1996-12-11 | 2000-04-04 | L'oreal | Process for the preparation of hydroxypropylated quaternary ammonium compounds containing an ester functional group |
| US6214325B1 (en) | 1996-12-11 | 2001-04-10 | L'oreal | Hydroxypropyl quaternary ammonium compounds containing an ester function, and cosmetic and dermatological compositions containing them |
| EP0918104A1 (en) * | 1997-11-19 | 1999-05-26 | Arizona Chemical Oy | A papermaking process and a cationic chemical |
| US6521782B1 (en) * | 1999-01-21 | 2003-02-18 | Atofina | Method for making aqueous solutions of unsaturated quaternary ammonium salts |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5229292B2 (en:Method) | 1977-08-01 |
| GB1390534A (en) | 1975-04-16 |
| JPS4852716A (en:Method) | 1973-07-24 |
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