US4289868A
Expired / Lapsed
US
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Polyhydantoins from unsaturated carboxylic acids and polyiso(thio)cyanates
Assignee: Bayer AG
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Filing: 1979-12-06
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Granted: 1981-09-15
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Expires: 1999-12-06
Abstract
Abstract Poly(thio)hydantoins are prepared by reacting an iso(thio)cyanate having at least two iso(thio)cyanate moieties with a compound of the formula ##STR1## wherein R 1 and R 2 are the same or different and each represents hydrogen, halogen, a C 1 -C 20 aliphatic group, a C 7 -C 20 aliphatic-aromatic group, a C 6 -C 20 aromatic group or a heterocyclic group having from 4 to 16 ring members and at least one N, O or S atom; A represents CN, COR, substituted or unsubstituted C 1 -C 20 aliphatic group, C 7 -C 20 aliphatic-aromatic group, C 6 -C 20 aromatic group or a heterocyclic group having from 4 to 16 ring members and at least one N, O or S atom wherein the substituents are NO 2 , COOR 4 , CN, CO or OH; R and R 4 are selected from the definition of R 1 and R 2 with the exclusion of halogen; M represents OH or ##STR2## and R 6 represents hydrogen, unsubstituted or substituted C 2 -C 20 aliphatic, C 5 -C 12 cycloaliphatic, C 6 -C 20 aliphatic aromatic, or a C 5 -C 12 aromatic or C 5 -C 12 cycloaliphatic containing a heteroatom N, O or S in the ring, wherein the substituents are at least one halogen, C 1 -C 10 alkyl, or C 6 -C 12 aryl.
Inventors
- 👤 Jurgen Lewalter
- 👤 Rudolf Merten
- 👤 Wilfried Zecher
- 👤 Willi Dunwald
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 15:16
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/72; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/671; C08G18/675; C08G18/6755
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
243 words
A process for the preparation of polyhydantoins and polythiohydantoins, comprising reacting organic polyisocyanates or polyisothiocyanates at temperatures of from -20° to +500° C. with compounds consisting essentially of unsaturated carboxylic acid derivatives of the formula: ##STR11## wherein R 1 and R 2 are the same or different and each represents hydrogen, halogen, a C 1 -C 20 aliphatic group, a C 7 -C 20 aliphatic-aromatic group, a C 6 -C 20 aromatic group or a hetercyclic group having from 4 to 16 ring members and at least one N, O or S atom; A represents CN, COR, substituted or unsubstituted C 1 -C 20 aliphatic group, C 7 -C 20 aliphatic-aromatic group, C 6 -C 20 aromatic group or a heterocyclic group having from 4 to 16 ring members and at least one N, O or S atom wherein the substituents are NO 2 , COOR 4 , CN, CO or OH; R and R 4 are selected from the definition of R 1 and R 2 with the exclusion of halogen; M represents OH or ##STR12## and R 6 represents hydrogen, unsubstituted or substituted C 2 -C 20 aliphatic, C 5 -C 12 cycloaliphatic, C 6 -C 20 aliphatic aromatic, or a C 5 -C 12 aromatic or C 5 -C 12 cycloaliphatic containing a heteroatom N, O or S in the ring, wherein the substituents are at least one halogen, C 1 -C 10 alkyl or C 6 -C 12 aryl.
Claim 2
Dependent Claim
243 words
A process for the preparation of polyhydantoins and polythiohydantoins, comprising reacting organic polyisocyanates or polyisothiocyanates at temperatures of from -20° to +500° C. with compounds consisting essentially of unsaturated carboxylic acid derivatives of the formula: ##STR11## wherein R 1 and R 2 are the same or different and each represents hydrogen, halogen, a C 1 -C 20 aliphatic group, a C 7 -C 20 aliphatic-aromatic group, a C 6 -C 20 aromatic group or a hetercyclic group having from 4 to 16 ring members and at least one N, O or S atom; A represents CN, COR, substituted or unsubstituted C 1 -C 20 aliphatic group, C 7 -C 20 aliphatic-aromatic group, C 6 -C 20 aromatic group or a heterocyclic group having from 4 to 16 ring members and at least one N, O or S atom wherein the substituents are NO 2 , COOR 4 , CN, CO or OH; R and R 4 are selected from the definition of R 1 and R 2 with the exclusion of halogen; M represents OH or ##STR12## and R 6 represents hydrogen, unsubstituted or substituted C 2 -C 20 aliphatic, C 5 -C 12 cycloaliphatic, C 6 -C 20 aliphatic aromatic, or a C 5 -C 12 aromatic or C 5 -C 12 cycloaliphatic containing a heteroatom N, O or S in the ring, wherein the substituents are at least one halogen, C 1 -C 10 alkyl or C 6 -C 12 aryl.
Claim 3
Dependent Claim
275 words
A process as claimed in claim 1 wherein the unsaturated carboxylic acid derivative correspond to the formula ##STR13## wherein R 1 and R 2 , which may be the same or different, each represents hydrogen, halogen, a C 1 -C 20 aliphatic group, a C 7 -C 20 aliphatic-aromatic group, a C 6 -C 20 aromatic group or a heterocyclic group having from 4 to 16 ring members and at least one N, O or S atom; A represents a substituted or unsubstituted C 1 -C 20 aliphatic group, a C 7 -C 20 aliphatic-aromatic group, a C 6 -C 20 aromatic group or a heterocyclic group having from 4 to 16 ring members and at least one N, O or S atom wherein the substituents of the substituted moieties are halogen, NO 2 , COOR 4 , CN, CO, OH, CN or COR wherein R 4 is the same as R 1 wherein R represents hydrogen, a C 1 -C 20 aliphatic group, a C 7 -C 20 aliphatic-aromatic group, a C 6 -C 20 aromatic group or a heterocyclic group having from 4 to 16 ring members and at least one N, O or S atoms; R 6 represents hydrogen, a C 2 -C 20 aliphatic group, a C 5 -C 12 cycloaliphatic group, a C 6 -C 12 aliphatic-aromatic group, or a C 5 -C 12 aromatic or C 5 -C 12 cycloaliphatic group containing N, O or S heteroatoms in the ring, each of which may be substituted by halogen, by C 1 -C 10 alkyl groups and/or by C 6 -C 12 aryl groups and m is 1 or 2.
Claim 4
Dependent Claim
16 words
A process as claimed in claim 1, wherein as unsaturated carboxylic acid, cinnamic acid is used.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1984-09-14 | 1985-03-16 | 1985-09-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-14 | 1989-03-16 | 1989-09-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-14 | 1993-03-16 | 1993-09-15 | $7700.00 | Window Closed / Lapsed |