GB846601A - Vinyl hydantoins - Google Patents
Vinyl hydantoinsInfo
- Publication number
- GB846601A GB846601A GB116858A GB116858A GB846601A GB 846601 A GB846601 A GB 846601A GB 116858 A GB116858 A GB 116858A GB 116858 A GB116858 A GB 116858A GB 846601 A GB846601 A GB 846601A
- Authority
- GB
- United Kingdom
- Prior art keywords
- vinyl
- alkyl
- methyl
- hydantoin
- ethyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention comprises polymers and copolymers of vinylhydantoins of formula: <FORM:0846601/IV(a)/1> where R1 is alkyl and R2 is alkyl, carboalkoxyalkyl, aryl, aralkyl, cycloalkyl, cycloalkyl-alkyl, aralkenyl or heterocyclic, or R1 and R2 together form a polymethylene or alkyl-substituted polymethylene ring; R3 is vinyl, alkyl or aryl; and R4 is vinyl, acyl or hydrogen, at least one of R3 and R4 being vinyl. (For preparation see Group IV(b)). The copolymers may be formed by the copolymerisation of two or more vinylhydantoins or by copolymerising at least one vinylhydantoin with at least one compound containing at least one ethylenic linkage. Bulk, solution, suspension or emulsion polymerisation may be used. Water or an inert organic liquid, e.g. benzine may be present. Temperature up to about 100 DEG C. are preferred and one or more catalysts, especially free radical catalysts such as berzoyl peroxide, hydrogen peroxide, azobisiso-butyronitrile, and di-t-butyl-peroxide, are preferably used. Examples describe the preparation of polymers of: 3-vinyl-5,5-dimethyl-; 3-vinyl-5-ethyl-5-methyl-; 3-vinyl-5-methyl-5-isobutyl-; 3-vinyl-5-phenyl-5-undecyl-; 1,3-divinyl-5-methyl-5-thiemyl-; 3-vinyl-5,5-cyclohexylspiro-; 3-vinyl-5,5-cyclopentylspiro-; 1,3-divinyl-5-methyl-5-phenyl-5-phenyl-; 3-vinyl-5-methyl-5-carbethoxymethyl-and 3-vinyl-5-methyl-5-styryl-hydantoin; of the copolymers of 3-vinyl-5,5-dimethyl-hydantoin with vinyl acetate, acrylonitrile, vinyltoluene and styrene; and of a terpolymer of 3-vinyl-5,5-cyclohexylspirohydantoin, 3-vinyl-5,5-dimethylhydantoin and 3-vinyl-5-ethyl-5-methylhydantoin.ALSO:The invention comprises vinylhydantoins of formula :-<FORM:0846601/IV(b)/1> where R1 is alkyl and R2 is alkyl, carbo-alkoxyalkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, aralkenyl, or heterocyclic ; or R1 and R2 together form a polymethylene or alkyl-substituted polymethylene ring ; R3 is vinyl, alkyl or aryl ; and R4 is vinyl, acyl or hydrogen, at least one of R3 and R4 being vinyl. They are prepared by reacting the corresponding hydantoin in which the vinyl group or groups are replaced by hydrogen, in solution or suspension in an inert liquid with acetylene at a pressure within the range 1-30 atm. and at a temperature within the range 140-250 DEG C. in the presence of a vinylation catalyst. Specified p inert liquids are hydrocarbons and halogenated hydrocarbons ; specified catalysts are cadmium and zinc oxides and their salts with weak acids. A polymerisation inhibitor may be present. Anhydrous conditions are preferred. When starting with a hydantoin in which both the 1- and 3- positions are vacant, a mixture of 3-monovinyl and 1, 3-divinyl derivatives normally results, but by controlling the quantity of acetylene at least a 90% proportion by weight of the monovinyl compound may be obtained or alternatively by continued vinylation it is possible to obtain predominantly divinyl derivative. The products may be polymerised (see Group IV(a)). The vinylhydantoins may be hydrogenated to the corresponding ethyl compounds. Starting materials prepared in exapmles by the reaction of a cyanide and ammonium carbonate with the appropriate ketone are :-(17) 5-undecyl-5phenylhydantoin from laurophenone ; (27) 5,5-(2-methylcyclohexyl)-spirohydantoin from methylcyclohexanone; (35) 5-methyl-5-carbethoxymethylhydantoin from acetoacetic ester and (36) 5-methyl-5-hexahydrobenzylhydantoin from cyclohexylacetone : also prepared are (28) 3-ethyl-5,5-dimethylhydantoin by reacting ethyl bromide with the potassium derivative of 5,5-dimethylhydantoin and 1-acetyl-5,5-dimethylhydantoin by the action of acetic anhydride on 5,5-dimethyl hydantoin.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB116858A GB846601A (en) | 1958-01-13 | 1958-01-13 | Vinyl hydantoins |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB116858A GB846601A (en) | 1958-01-13 | 1958-01-13 | Vinyl hydantoins |
Publications (1)
Publication Number | Publication Date |
---|---|
GB846601A true GB846601A (en) | 1960-08-31 |
Family
ID=9717350
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB116858A Expired GB846601A (en) | 1958-01-13 | 1958-01-13 | Vinyl hydantoins |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB846601A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3197477A (en) * | 1961-05-01 | 1965-07-27 | Sterling Drug Inc | Allylhydantoins |
US4091223A (en) * | 1976-08-04 | 1978-05-23 | Ciba-Geigy Corporation | Unsaturated hydantoin coagents |
DE2829307A1 (en) * | 1977-07-07 | 1979-01-25 | Ciba Geigy Ag | NEW VINYLAETHER, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR THE PRODUCTION OF POLYMERS |
US4167465A (en) | 1976-08-04 | 1979-09-11 | Ciba-Geigy Corporation | Unsaturated hydantoin coagents |
US4229519A (en) | 1978-05-31 | 1980-10-21 | Eastman Kodak Company | Photo-polymerizable water-developable composition and elements |
US4241073A (en) * | 1978-05-23 | 1980-12-23 | Lilly Industries Limited | Treatment of immediate hypersensitivity diseases with aryl hydantoins |
US4258149A (en) | 1978-03-13 | 1981-03-24 | Ciba-Geigy Corporation | Process for curing saturated polymers using divinyl hydantoin coagents |
-
1958
- 1958-01-13 GB GB116858A patent/GB846601A/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3197477A (en) * | 1961-05-01 | 1965-07-27 | Sterling Drug Inc | Allylhydantoins |
US4091223A (en) * | 1976-08-04 | 1978-05-23 | Ciba-Geigy Corporation | Unsaturated hydantoin coagents |
US4167465A (en) | 1976-08-04 | 1979-09-11 | Ciba-Geigy Corporation | Unsaturated hydantoin coagents |
DE2829307A1 (en) * | 1977-07-07 | 1979-01-25 | Ciba Geigy Ag | NEW VINYLAETHER, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR THE PRODUCTION OF POLYMERS |
US4256867A (en) | 1977-07-07 | 1981-03-17 | Ciba-Geigy Corporation | Novel vinyl ethers, process for their preparation, and their use for the preparation of polymers |
US4258149A (en) | 1978-03-13 | 1981-03-24 | Ciba-Geigy Corporation | Process for curing saturated polymers using divinyl hydantoin coagents |
US4241073A (en) * | 1978-05-23 | 1980-12-23 | Lilly Industries Limited | Treatment of immediate hypersensitivity diseases with aryl hydantoins |
US4229519A (en) | 1978-05-31 | 1980-10-21 | Eastman Kodak Company | Photo-polymerizable water-developable composition and elements |
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