US2635100A - Monoquaternary ammonium carbonates and their preparation - Google Patents
Monoquaternary ammonium carbonates and their preparation Download PDFInfo
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- US2635100A US2635100A US127520A US12752049A US2635100A US 2635100 A US2635100 A US 2635100A US 127520 A US127520 A US 127520A US 12752049 A US12752049 A US 12752049A US 2635100 A US2635100 A US 2635100A
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
- D06M13/232—Organic carbonates
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- 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
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/15—Antistatic agents not otherwise provided for
- Y10S260/19—Non-high polymeric antistatic agents/n
- Y10S260/20—Antistatic agent contains pentavalent nitrogen
Definitions
- this inven- -tion which comprises certa n n w qua e n ry e monium carbonates and a process tor their production which comprisesreaotins pre e a y in the presence of alcohol, a temperatur Within the ran e of lQQ Q, 11D 12. 1 h? deoomposi- 7 tion point of the resultin oua erha yammonium carbonate, a tertiaryvrnonoom he, ie, a triall phatic amine which, exclusiye o amin nitrogen. is aliphatic acyclic hydrocarbon, with a dialiphatic hydrocarbon ester of carbonic acid hieh.
- ao ta is aliphatic acyc c hydroearhen- Fo use thi invention prefe ed te t ary mines are ie :phatic saturated acyclic hydr carbon am nes an the preferred dialiphatie esters of c bor e aei are diaiiphatio saturated aeyolio hyd ocarbon eeters of carbonic acid.
- i irhe newv monoqoat rhary ammonium fii nates of this invention are tho e having the vonion of a monoal p acyc ic hydrocarbon ester o carbonic acid attached th ou oxy en to h quaternary nitro en vato t e remainin fou valences of saidcq aierhr y 11 1 195 &9 being bonded to aliphatic acyclic h d oo rh n e eol at least three of which are monovalent aliphatic acyclic hydrocarbon radicals.
- Preferred monoquaternary ammoniumca-rbonates are those havin theanion of a m noaliphati satura ed acycli -hydrocarbon ester of carbonic acid attached throu h oxygen to the quaterna y nitrogen atom, l th ema ng ur alenoes cream quaternary trogen atom bei bond to a inhatio satu- & rated acyclichydrocarbon radicals, or least three of-which are m n alent al p t c sa urate acyclic hydrocarbon radicals.
- quaternary ammonium carbonates can be represented by the formula:
- the mole ratio of tertiary amine to dialkyl carbonate may vary between :1 to 1:10. Best results are achieved, however, with a hole ratio of 2:1 to 3:1.
- the time necessary to complete the reaction decreases with increasing temperature, it is desirable, though not essential, to operate at a temperature as high as possible below the decomposition temperature of the quaternary ammonium carbonate formed.
- the temperature range of 150 to 180 C. has been found the most satisfactory although the reaction may be carried out at a temperature'as low at 100 C.
- the time of reaction varies from 6 to hours although at 150 to 180 C., 8 to 12 hours reaction time is usually satisfactory.
- Example I A mixture of 20.2 parts of triethylamine, 4.5 parts of dimethylcarbonate (boiling point 2 5)s a) 0 OCH:
- Example II Employing the procedure of the above example, 40 parts of triethylamine, 12 parts of dimethyl carbonate, and 40 parts of methanol yielded 7 parts of triethylmethylammonium methyl car-.
- Example III The triethylmethylammonium methyl carbonate (3.3 parts) was also obtained without the methanol solvent by the same procedure as described in Example I from 32 parts of triethylamine and 7.2 parts of dimethyl carbonate.
- Example IV A mixture of 202 parts of triethylamine. 5.9
- tertiary monoamine i. e., a trialiphatic acylic hydrocarbon' amine
- dialiphatic' acyclic hydrocarbon ester of carbonic acid The tertiary monoamines employed in the process of this invention 1 are those having only monovalent ali'phatic acypreferred. Additional examples of these tertiary amines include tripropylamine, triisopropylamine,
- triisobutylamine tri-n-butylamine, tri-n-amylamine, tri-n-octylamine, dimethyldodecylamine, diethylallylamine, dimethyloleylamine, dimethyldocosylamine, and the like.
- the carbonates i. e., the dialiphatic acyclic hydrocarbon esters of carbonic acid, which can be employed in this process are those in which the two valences of the carbonyldioxy radical,
- aliphatic acyclic hydrocarbon radicals preferably two monovalent alkyl radicals j of up to 6 carbon atoms or the divalent ethylene radical, CHzCH2--.
- Examples include di methyl carbonate, diethyl carbonate, dipropyl carbonate, dibutyl carbonate, diisobutyl carbonate, diamyl carbonate, diisoamyl carbonate,
- t e use f a1 coholic solvents, particularly the monohydric'al- .cohols, for'exam'ple', alkanols, cycloalkanols and aralkanolsof up to 7 carbon atoms, usually give superior results.
- the quaternary ammonium salts of this invention are appreciably water-soluble and useful as antistatic agents for textile yarns.
- Those quaternary ammonium carbonates which contain at least one monovalent aliphatic acyclic hydrocarbon radical, especially an alkyl radical, of six or more carbon atoms attached to the quaternary nitrogen atom are particularly desirable and preferred in this respect.
- the quaternary ammonium salts of this invention are also important intermediates for the preparation of quaternary ammonium bases, beingreadily converted to these on treatment with alkaline earth hydroxides, e. g., barium hydroxide and calcium hydroxide.
- alkaline earth hydroxides e. g., barium hydroxide and calcium hydroxide.
- a monoquaternary ammonium carbonate having the formula wherein the (R)s are alkyl radicals of from 1 to 18 carbon atoms and the (R')s are alkyl radicals of from 1 to 6 carbon atoms.
- a trialiphatic acyclic hydrocarbon amine having the formula (RMN wherein the (R)s are monovalent aliphatic hydrocarbon radicals of from 1 to 22 car; bon atoms from the group consisting of alkyl radicals and alkenyl radicals containing one ethylenic bond only, and at least two of the (R)s are alkyl radicals, and an aliphatic hydrocarbon ester of carbonic acid having the formula R'o- -oR' wherein the (R')s are selected from the group consisting of alkyl radicals of from 1 to 6 carbon atoms and the methylene radical, the latter being joined together and to the two oxygen atoms to form a five-membered heterocyclic ring.
- RPN trialiphatic acyclic hydrocarbon amine having the formula (RMN wherein the (R)s are monovalent aliphatic hydrocarbon radicals of from 1 to 22 car; bon atoms from the group consisting of alkyl radicals and alkenyl
- a process for preparing a monoquaternary ammonium carbonate which comprises heating at a temperature within the range of 100 C. up to the decomposition point of the resulting monoquaternary ammonium carbonate, a trialkyl amine having the formula (R)3N wherein the (R)s are alkyl radicals of from 1 to 18 carbon atoms, and a, dialkyl ester of carbonic acid having the formula wherein the (R')s are alkyl radicals of from 1 to 6 carbon atoms.
- a process for preparing a monoquaternary ammonium carbonate which comprises heating at a temperature within the range of 100 C. up to the decomposition point of the resulting monoquaternary ammonium carbonate, a trialkyl "amine having the formula (R)3N wherein the (ms are alkyl radicals of from 1 to 18 carbon atoms, and cyclic ethylene carbonate.
- a process for preparing triethylmethylammonium methyl carbonate which comprises heating at a temperature within the range of 150- 180 C., triethylamine and dimethyl carbonate in a monohydric alcohol solvent of from 1 to '7 carbon atoms.
- a process for preparing tetraethylammonium ethyl carbon-ate which comprises heating at a temperature'within the range of 150-180" 0., triethylamine and diethyl carbonate in a ,inonohydric alcohol solvent of from 1 to 7 carbon ylammonium methyl carbonate which comprises from 1 to '7 carbon atoms.
- a process for preparing the cyclic carbonate of triethyl-Z-hydroxyethylammonium hydroxide which comprises heating at a temperature Within the range of 150-180 C., triethylamine and cyclic ethylene carbonate in a monohydric alcohol solvent of from 1 to 7 carbon atoms.
Description
Patented Apr. 14, 1953 UNITED STATES PATENT QFFICE;
MQNOQUATEBNARY AMMONIUM CARBON! ATES. AND THEIR rncramrron James H. Werntz, Wilmington, DeL, assignor to E. I. du Pont de Nemours & Company, Wil? min ten, De. a p ation of Delaware No Drawing. Application November 115, 1949, Serial No. 127,520 4 invention relates to quaternary ammonium salts and, more particularly, to quate nary ammcnium carbonates'and to methods tor thei pr paration.
Altho gh ccnside abletechniool in rest q r ary a mon um sa ts and their correspondin bases has developed i re ent yea s,
ua nary a monium salts f the very weak acids, notably monoquaternary ammo um salts of carbonic acid, have remained unknown.
It is an object of this invention to provide monoquaternary ammonium salts of carbonic acid. A further object is to provide a novel method for the production of quaternary ammonium carbonates. other Objects will appear hereinafter.
These objects are accomplished by this inven- -tion which comprises certa n n w qua e n ry e monium carbonates and a process tor their production which comprisesreaotins pre e a y in the presence of alcohol, a temperatur Within the ran e of lQQ Q, 11D 12. 1 h? deoomposi- 7 tion point of the resultin oua erha yammonium carbonate, a tertiaryvrnonoom he, ie, a triall phatic amine which, exclusiye o amin nitrogen. is aliphatic acyclic hydrocarbon, with a dialiphatic hydrocarbon ester of carbonic acid hieh.
. exclusive of the .carbonyldioxy radical.
ao ta is aliphatic acyc c hydroearhen- Fo use thi invention prefe ed te t ary mines are ie :phatic saturated acyclic hydr carbon am nes an the preferred dialiphatie esters of c bor e aei are diaiiphatio saturated aeyolio hyd ocarbon eeters of carbonic acid. I
i irhe newv monoqoat rhary ammonium fii nates of this invention are tho e having the vonion of a monoal p acyc ic hydrocarbon ester o carbonic acid attached th ou oxy en to h quaternary nitro en vato t e remainin fou valences of saidcq aierhr y 11 1 195 &9 being bonded to aliphatic acyclic h d oo rh n e eol at least three of which are monovalent aliphatic acyclic hydrocarbon radicals. Preferred monoquaternary ammoniumca-rbonates are those havin theanion of a m noaliphati satura ed acycli -hydrocarbon ester of carbonic acid attached throu h oxygen to the quaterna y nitrogen atom, l th ema ng ur alenoes cream quaternary trogen atom bei bond to a inhatio satu- & rated acyclichydrocarbon radicals, or least three of-which are m n alent al p t c sa urate acyclic hydrocarbon radicals. These'new mono 1 Claims. (01. 260-244) quaternary ammonium carbonates can be represented by the formula:
o (an 'ogsoe' :ljhe fol-lowing equation with a typical tertiary amine and diester of carb nic acid represents the 7 reaction in thep ooe s o t is invention:
- QuHuNWLHa): :ilQaHrOlzQst) b 0 C i s Es1N( CHa)2O( O c 3H1 V v I 31, 1 in ee he p oe iee e pre a at n o t e .1
ie ry ammoni m a on t o this n en he ea n d-out by t r n; into a i bl oe o the se ected ialip o rtiar amine, fo exampl h l m riel end th d ll hh t o st or oer-home heid; in er xam e m th carbonate and iocsireooo.oi oooisooo seth ol Th react on vessel is closed and then heated u der qautoeenous pressure at a suitame'ierhnere hr preierablyinthe raneeoi 50 to liafiio-nforalooo 146 torn hours with agitation. .hiters mpleti.
of t reaction, e ree toris coolednoreened and he contents are discharged. The-product is then isolated by removal, through distillation, of the solvent, if present, and'of any unreacted reagents.
The mole ratio of tertiary amine to dialkyl carbonate may vary between :1 to 1:10. Best results are achieved, however, with a hole ratio of 2:1 to 3:1. The use of alcoholic solvents ordinarily gives superior results, the preferable mole ratio of alcohol to tertiary amine being about 5:1, although mole ratios of 1:1 to :1 can also be satisfactorily employed.
Since the time necessary to complete the reaction decreases with increasing temperature, it is desirable, though not essential, to operate at a temperature as high as possible below the decomposition temperature of the quaternary ammonium carbonate formed. In general, the temperature range of 150 to 180 C. has been found the most satisfactory although the reaction may be carried out at a temperature'as low at 100 C. Depending on the temperature and reagents employed as well as the presence of solvent, the time of reaction varies from 6 to hours although at 150 to 180 C., 8 to 12 hours reaction time is usually satisfactory.
The invention is illustrated in further detail by the following examples in which parts, unless otherwise specified, are given by weight.
Example I y A mixture of 20.2 parts of triethylamine, 4.5 parts of dimethylcarbonate (boiling point 2 5)s a) 0 OCH:
Example II Employing the procedure of the above example, 40 parts of triethylamine, 12 parts of dimethyl carbonate, and 40 parts of methanol yielded 7 parts of triethylmethylammonium methyl car-.
bonate.
Example III The triethylmethylammonium methyl carbonate (3.3 parts) was also obtained without the methanol solvent by the same procedure as described in Example I from 32 parts of triethylamine and 7.2 parts of dimethyl carbonate.
Example IV A mixture of 202 parts of triethylamine. 5.9
parts of diethyl carbonate and 16 parts of methanol was heated at 170 C. in a sealed glass reactor for 8 hours. The reaction product was then heated at 100 C. under about 15 mm. pressure to remove the unreacted tertiary amine and.
dialkyl carbonate. The residual tetraethylammonium ethyl carbonate (2.4 parts), a brown, hygroscopic oil, soluble in water, liberated carbon dioxide when dissolved in aqueous acid solution. Analysis by the Knorr method showed 28.9% carbonate as compared to the calculated value of 27.4% for carbonate'(COs) in (CzH5)4NO(|'|JOCzH 4 Example V Fifteen (15) parts of octadecyldimethylamine. 18 parts of dimethyl carbonate and 32 parts of methanol were heated in a sealed glass reactor for eight hours at 170 C. After removal of volatile material by heating on the steam bath under reduced pressure (about 5 mm.), 18.5 parts of octadecyltrimethyl ammonium methyl carbonate was obtained. This product, soluble in water, gave clear, strongly sudsing solutions. It analyzed for 3.78% nitrogen as compared to a calculated value of 3.62% for the above product.
Example VI Cyclic ethylene carbonate,
H JJ--CH F. P. 36 C.; B. P. 248 C., 10.1 parts, was reacted with 46.5 parts of triethylaminej in the presence of 37 parts of methanol at 170 C. for about 8 hours. After removal through distillation of the solvent, unreacted amine and cyclic ester from the reaction mixture, there was obtained 9.8 parts of hygroscopic, viscous, brown, water-soluble, oily cyclic carbonate of triethyl-2-hydroxyethylammonium hydroxide having the structural formula Analysis of the product showed a nitrogen content of 5.8%. a
This invention is not limited to the specific reactants illustrated in the foregoing examples, but
' embraces more broadly the reaction of a tertiary monoamine, i. e., a trialiphatic acylic hydrocarbon' amine, with a dialiphatic' acyclic hydrocarbon ester of carbonic acid. The tertiary monoamines employed in the process of this invention 1 are those having only monovalent ali'phatic acypreferred. Additional examples of these tertiary amines include tripropylamine, triisopropylamine,
triisobutylamine, tri-n-butylamine, tri-n-amylamine, tri-n-octylamine, dimethyldodecylamine, diethylallylamine, dimethyloleylamine, dimethyldocosylamine, and the like.
The carbonates, i. e., the dialiphatic acyclic hydrocarbon esters of carbonic acid, which can be employed in this process are those in which the two valences of the carbonyldioxy radical,
are bonded to aliphatic acyclic hydrocarbon radicals, preferably two monovalent alkyl radicals j of up to 6 carbon atoms or the divalent ethylene radical, CHzCH2--. Examples include di methyl carbonate, diethyl carbonate, dipropyl carbonate, dibutyl carbonate, diisobutyl carbonate, diamyl carbonate, diisoamyl carbonate,
gen-ids evens et yle e" car nate. a d e lik Thi by the roc ss des ibed. herein ca be prepar tetra-n-b y ammoni m bu lca bona e, m
'tri-n-butyla mine and di-nebutyl carbonate, do-
.decyltr me hvl amm ium me h carbonate rom dim hvldodcv amin a d me h l ca nate, and r v -e h l-buty a monium ethvlbutyl carb nat fromtri t y m ne nd hi (l-e h lbntvbcarb a e- In the proce of this nvention, t e use f a1 coholic solvents, particularly the monohydric'al- .cohols, for'exam'ple', alkanols, cycloalkanols and aralkanolsof up to 7 carbon atoms, usually give superior results. -'When processing the aliphatic tertiary amin whi h cont in at leas on mon valent aliphatic acyclic hydrocarbon group pfat least six carbon atoms, it is preferred to operate The quaternary ammonium salts of this invention are appreciably water-soluble and useful as antistatic agents for textile yarns. Those quaternary ammonium carbonates which contain at least one monovalent aliphatic acyclic hydrocarbon radical, especially an alkyl radical, of six or more carbon atoms attached to the quaternary nitrogen atom are particularly desirable and preferred in this respect. The quaternary ammonium salts of this invention are also important intermediates for the preparation of quaternary ammonium bases, beingreadily converted to these on treatment with alkaline earth hydroxides, e. g., barium hydroxide and calcium hydroxide.
As many apparently widely different embodiments of this invention may be made without departing from the spirit and scope thereof, it is to be understood that this invention is not limited to the specific embodiments thereof except as defined in the appended claims.
I claim:
1. A monoquaternary ammonium carbonate having the formula and oxygen atoms to form a six-membered heterocyclic ring.
2. A monoquaternary ammonium carbonate having the formula wherein the (R)s are alkyl radicals of from 1 to 18 carbon atoms and the (R')s are alkyl radicals of from 1 to 6 carbon atoms.
A monoqu te rnary ammonium ethane having the formu wherein the (R.)s are alkyl radicals of from 1 to lBcarbon atoms. I i
4; v'Jf.riethylmethylasnrnoriiium a e, 3 Q w V T t 'a thvhmmmium me hyl arbonate: 6. Octadecyltrimethylammonium' methyl carbonate.
methyl carbon- 7. The cycliccarbonateof 'triethyl -fi hydroxyethylammonium hydroxide having the formula 8. A process for preparing a monoquaternary ammonium carbonate which comprises heating at a temperature within the range of C. up to the decomposition point of the resulting monoquaternary ammonium carbonate, a trialiphatic acyclic hydrocarbon amine having the formula (RMN wherein the (R)s are monovalent aliphatic hydrocarbon radicals of from 1 to 22 car; bon atoms from the group consisting of alkyl radicals and alkenyl radicals containing one ethylenic bond only, and at least two of the (R)s are alkyl radicals, and an aliphatic hydrocarbon ester of carbonic acid having the formula R'o- -oR' wherein the (R')s are selected from the group consisting of alkyl radicals of from 1 to 6 carbon atoms and the methylene radical, the latter being joined together and to the two oxygen atoms to form a five-membered heterocyclic ring.
9. A process as set forth in claim 8 wherein said amine and said ester of carbonic acid are heated in an alcohol solvent.
10. A process for preparing a monoquaternary ammonium carbonate which comprises heating at a temperature within the range of 100 C. up to the decomposition point of the resulting monoquaternary ammonium carbonate, a trialkyl amine having the formula (R)3N wherein the (R)s are alkyl radicals of from 1 to 18 carbon atoms, and a, dialkyl ester of carbonic acid having the formula wherein the (R')s are alkyl radicals of from 1 to 6 carbon atoms.
11. A process as set forth in claim 10 wherein said amine and said ester of carbonic acid are heated in a monohydric alcohol solvent of from 1 to 7 carbon atoms.
12. A process for preparing a monoquaternary ammonium carbonate which comprises heating at a temperature within the range of 100 C. up to the decomposition point of the resulting monoquaternary ammonium carbonate, a trialkyl "amine having the formula (R)3N wherein the (ms are alkyl radicals of from 1 to 18 carbon atoms, and cyclic ethylene carbonate.
.aesmoo 13. A process as set forth in claim 12 wherein said amine and said cyclic ethylene carbonate are heated in a monohydric alcohol solvent of from 1 to 7 carbon atoms.
14. A process for preparing triethylmethylammonium methyl carbonate which comprises heating at a temperature within the range of 150- 180 C., triethylamine and dimethyl carbonate in a monohydric alcohol solvent of from 1 to '7 carbon atoms.
15. A process for preparing tetraethylammonium ethyl carbon-ate which comprises heating at a temperature'within the range of 150-180" 0., triethylamine and diethyl carbonate in a ,inonohydric alcohol solvent of from 1 to 7 carbon ylammonium methyl carbonate which comprises from 1 to '7 carbon atoms.
17. A process for preparing the cyclic carbonate of triethyl-Z-hydroxyethylammonium hydroxide which comprises heating at a temperature Within the range of 150-180 C., triethylamine and cyclic ethylene carbonate in a monohydric alcohol solvent of from 1 to 7 carbon atoms.
JAMES H. WERNTZ.
References Cited in the file of this patent Hackhs Chemical Dictionary, Third Edition, page 30 (1944)
Claims (2)
1. A MONOQUATERNARY AMMONIUM CARBONATE HAVING THE FORMULA
8. A PROCESS FOR PREPARING A MONOQUATERNARY AMMONIUM CARBONATE WHICH COMPRISES HEATING AT A TEMPERATURE WITHIN THE RANGE OF 100* C. UP TO THE DECOMPOSITION POINT OF THE RESULTING MONOQUATERNARY AMMONIUM CARBONATE, A TRIALIPHATIC ACYCLIC HYDROCARBON AMINE HAVING THE FORMULA (R)3N WHEREIN THE (R)S ARE MONOVALENT ALIPHATIC HYDROCARBON RADICALS OF FROM 1 TO 22 CARBON ATOMS FROM THE GROUP CONSISTING OF ALKYL RADICALS AND ALKENYL RADICALS CONTAINING ONE ETHYLENIC BOND ONLY, AND AT LEAST TWO OF THE (R)S ARE ALKYL RADICALS, AND AN ALIPHATIC HYDROCARBON ESTER OF CARBONIC ACID HAVING THE FORMULA
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Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4098686A (en) * | 1976-03-19 | 1978-07-04 | Vojislav Petrovich | Froth flotation method for recovering of minerals |
| JPS63284148A (en) * | 1987-05-14 | 1988-11-21 | Mitsubishi Petrochem Co Ltd | Production of quaternary ammonium inorganic acid salt |
| US4792417A (en) * | 1985-12-19 | 1988-12-20 | Enichem Sintesi S.P.A. | Stainless steels stress corrosion inhibitors |
| EP0400435A2 (en) * | 1989-06-01 | 1990-12-05 | BASF Aktiengesellschaft | Carbonic half-ester of betaine structure |
| US5489663A (en) * | 1994-02-17 | 1996-02-06 | Basf Aktiengesellschaft | Preparation of polyisocyanates containing isocyanurate groups and use thereof |
| WO2003006419A1 (en) * | 2001-07-09 | 2003-01-23 | Lonza Inc. | In situ process for preparing quaternary ammonium bicarbonates and quaternary ammonium carbonates |
| JP2003313170A (en) * | 2002-04-23 | 2003-11-06 | Tosoh Corp | Method for producing cyclic amidinium organic acid salt |
| US20070227675A1 (en) * | 2003-07-04 | 2007-10-04 | Sinorgchem Co. | Process for preparing 4-aminodiphenylamine |
| US20110226606A1 (en) * | 2003-07-04 | 2011-09-22 | Jiangsu Sinorgchem Technology Co., Ltd. | Falling film evaporator |
| EP2374836A1 (en) | 2010-04-07 | 2011-10-12 | Nuplex Resins B.V. | Crosslinkable composition crosslinkable with a latent base catalyst. |
| EP2457981A1 (en) * | 2006-09-01 | 2012-05-30 | The Lubrizol Corporation | Quaternary ammonium salt of a mannich compound |
| EP2522682A1 (en) | 2005-03-15 | 2012-11-14 | Polyplastics Co., Ltd. | Unstable terminal group decomposer, and stabilized polyacetal resin, manufacturing method, composition and molded article using the same |
| WO2013050574A1 (en) | 2011-10-07 | 2013-04-11 | Nuplex Resins B.V. | A crosslinkable composition comprising a latent base catalyst and latent base catalyst compositions |
| US8686188B2 (en) | 2003-07-04 | 2014-04-01 | Jiangsu Sinorgchem Technology Co., Ltd. | Process for preparing 4-aminodiphenylamine |
| US20140296573A1 (en) * | 2013-03-27 | 2014-10-02 | Johnson Matthey Plc | Method of Making a Templating Agent |
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| US10604622B2 (en) | 2013-04-08 | 2020-03-31 | Allnex Netherlands B.V. | Composition crosslinkable by Real Michael Addition (RMA) reaction |
| US10647876B2 (en) | 2011-10-07 | 2020-05-12 | Allnex Netherlands B.V. | Crosslinkable composition cross-linkable by real Michael addition reaction and resins for use in said composition |
| US10759962B2 (en) | 2015-04-17 | 2020-09-01 | Allnex Netherlands B.V. | Method for applying RMA crosslinkable coating on modified epoxy primer coating |
| US10767074B2 (en) | 2015-04-17 | 2020-09-08 | Allnex Netherlands B.V. | Process for the manufacture of a crosslinkable composition |
| US10774238B2 (en) | 2015-04-17 | 2020-09-15 | Allnex Netherlands B.V. | Method for curing a RMA crosslinkable resin coating, RMA crosslinkable compositions and resins for use therein |
| US11814536B2 (en) | 2015-04-17 | 2023-11-14 | Allnex Netherlands B.V. | Floor coating compositions |
-
1949
- 1949-11-15 US US127520A patent/US2635100A/en not_active Expired - Lifetime
Non-Patent Citations (1)
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Cited By (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4098686A (en) * | 1976-03-19 | 1978-07-04 | Vojislav Petrovich | Froth flotation method for recovering of minerals |
| US4792417A (en) * | 1985-12-19 | 1988-12-20 | Enichem Sintesi S.P.A. | Stainless steels stress corrosion inhibitors |
| US4849170A (en) * | 1985-12-19 | 1989-07-18 | Enichem Sintesi S.P.A. | Stainless steels stress corrosion inhibitors |
| JPS63284148A (en) * | 1987-05-14 | 1988-11-21 | Mitsubishi Petrochem Co Ltd | Production of quaternary ammonium inorganic acid salt |
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