GB1112439A - Aminoalkyl esters of ª‡,ª‰-unsaturated acids and method of preparing these compounds - Google Patents
Aminoalkyl esters of ª‡,ª‰-unsaturated acids and method of preparing these compoundsInfo
- Publication number
- GB1112439A GB1112439A GB161566A GB161566A GB1112439A GB 1112439 A GB1112439 A GB 1112439A GB 161566 A GB161566 A GB 161566A GB 161566 A GB161566 A GB 161566A GB 1112439 A GB1112439 A GB 1112439A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- alkenyl
- specified
- compounds
- group
- 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
Links
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 125000004103 aminoalkyl group Chemical group 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 239000003054 catalyst Substances 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000003112 inhibitor Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- -1 alkyl phenols Chemical class 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000004780 naphthols Chemical class 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 229920000058 polyacrylate Polymers 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 150000008442 polyphenolic compounds Chemical class 0.000 abstract 1
- 235000013824 polyphenols Nutrition 0.000 abstract 1
- 238000010526 radical polymerization reaction Methods 0.000 abstract 1
- 239000010936 titanium Substances 0.000 abstract 1
- 229910052719 titanium Inorganic materials 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Acrylic polymers are obtained by free radical polymerization at elevated temperatures of esters of the formula <FORM:1112439/C3/1> where R is hydrogen or a methyl group, n is 2, 3 or 4 and A is <FORM:1112439/C3/2> or <FORM:1112439/C3/3> where R1 is an alkyl or alkenyl group, R2 is an alkenyl group and R3 and R4 are alkyl groups. A suitable catalyst is bis - (azobutyronitrile). Those monomers in which R2 and/or R1 are alkenyl groups can be polymerized in a first stage under mild conditions to polymerize the acrylyl bond and in a subsequent stage under more severe conditions to obtain a three-dimensional polymer through the alkenyl groups. A number of monomers are specified.ALSO:The invention comprises aminoalkyl esters of the formula <FORM:1112439/C2/1> where R is hydrogen or methyl, n is 2, 3 or 4 and A is <FORM:1112439/C2/2> where R1 is alkyl or alkenyl, R2 is alkenyl, R3 is alkyl and R4 is an alkyl group. The compounds are made by heating a C1- 4 alkyl ester of acrylic or methacrylic acid with an aminoalcohol HO-CnH2n-A in the presence of a transesterification catalyst and a polymerization inhibitor. Specified catalysts are the alkali metals and the alcoholates of the alkali metals, titanium and aluminium. Suitable inhibitors are phenols, alkyl phenols, polyphenols, naphthols, aromatic amines and aminophenols. Specified reaction temperatures are in the range 60-160 DEG C. Numerous compounds are specified.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB161566A GB1112439A (en) | 1966-01-13 | 1966-01-13 | Aminoalkyl esters of ª‡,ª‰-unsaturated acids and method of preparing these compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB161566A GB1112439A (en) | 1966-01-13 | 1966-01-13 | Aminoalkyl esters of ª‡,ª‰-unsaturated acids and method of preparing these compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1112439A true GB1112439A (en) | 1968-05-08 |
Family
ID=9725014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB161566A Expired GB1112439A (en) | 1966-01-13 | 1966-01-13 | Aminoalkyl esters of ª‡,ª‰-unsaturated acids and method of preparing these compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1112439A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000496A1 (en) * | 1977-07-19 | 1979-02-07 | Ciba-Geigy Ag | Acrylic polymers substituted by N-heterocyclic rings and their use as light protection agents |
| EP0010518A1 (en) * | 1978-10-13 | 1980-04-30 | Ciba-Geigy Ag | Acrylic copolymers bearing N-heterocyclic side rings, their use, and process for their preparation |
-
1966
- 1966-01-13 GB GB161566A patent/GB1112439A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000496A1 (en) * | 1977-07-19 | 1979-02-07 | Ciba-Geigy Ag | Acrylic polymers substituted by N-heterocyclic rings and their use as light protection agents |
| US4210612A (en) | 1977-07-19 | 1980-07-01 | Ciba-Geigy Corporation | Novel polymeric N-heterocyclic compounds |
| EP0010518A1 (en) * | 1978-10-13 | 1980-04-30 | Ciba-Geigy Ag | Acrylic copolymers bearing N-heterocyclic side rings, their use, and process for their preparation |
| US4276401A (en) | 1978-10-13 | 1981-06-30 | Ciba-Geigy Corporation | N-Heterocyclic substituted acryloyl polymeric compounds |
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