← Back to Patent Explorer
US3966683A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the preparation of compounds which contain hydantoin groups

Assignee: Bayer AG
•
Filing: 1974-08-01
•
Granted: 1976-06-29
•
Expires: 1994-08-01
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract A process for preparing compounds which contain hydantoin groups, which is characterized in that compounds which contain isocyanate or isothiocyanate groups are reacted with compounds which contain an α-halocarboxylic acid group or derivatives thereof at least once in the molecule.

Inventors

  • 👤 Rudolf Merten
  • 👤 Jurgen Lewalter
  • 👤 Wilfried Zecher

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 09:03
CPC Classifications
C; C07; C07D; C07D235/00; C07D235/02; C07D233/00; C07D233/54; C07D233/66; C07D233/72; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3802; C08G18/70; C08G18/72; C08G18/77; C08G18/78; C08G18/7875; C08G18/7887; C08G18/80; C08G73/00; C08G73/06; C08G73/0605; C08G73/0616; Y; Y10; Y10S; Y10S260/00; Y10S260/34; Y10S525/00; Y10S525/908

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 215 words
A process for the preparation of a hydantoin which comprises reacting at a temperature of 50° to 350°C. a. at least one compound of the formula R.sup.3 (--NCX).sub.z wherein X is O or S; z is an integer of from 2 to 3 and R 3 is an optionally substituted aliphatic radical containing 1-20 carbon atoms, an optionally substituted aromatic radical containing 5-12 carbon atoms, a cycloaliphatic radical containing 5-12 carbon atoms, an aliphatic-aromatic radical containing 6-20 carbon atoms or an aromatic or cycloaliphatic heterocyclic radical containing 5-12 ring atoms which contains or is substituted by hetero atoms such as N, O or S, with b. at least one α-halocarboxylic acid selected from the group consisting of ##EQU11## wherein Hal is halogen; R 4 is an optionally substituted aromatic radical containing 5-10 carbon atoms, an aliphatic radical containing 1-20 carbon atoms, a cycloaliphatic radical containing 5-10 carbon atoms, hydrogen or two radicals R 4 taken together with the carbon atom to which they are attached form a cycloaliphatic ring of 5-7 ring members; R 6 is an aliphatic radical containing 1-10 carbon atoms, a cycloaliphatic radical containing 5-10 carbon atoms, an aliphatic-aromatic radical containing 6-10 carbon atoms or an aromatic radical containing 5-10 carbon atoms and y is an integer of from 1 to 3.
Claim 2
Dependent Claim 215 words
A process for the preparation of a hydantoin which comprises reacting at a temperature of 50° to 350°C. a. at least one compound of the formula R.sup.3 (--NCX).sub.z wherein X is O or S; z is an integer of from 2 to 3 and R 3 is an optionally substituted aliphatic radical containing 1-20 carbon atoms, an optionally substituted aromatic radical containing 5-12 carbon atoms, a cycloaliphatic radical containing 5-12 carbon atoms, an aliphatic-aromatic radical containing 6-20 carbon atoms or an aromatic or cycloaliphatic heterocyclic radical containing 5-12 ring atoms which contains or is substituted by hetero atoms such as N, O or S, with b. at least one α-halocarboxylic acid selected from the group consisting of ##EQU11## wherein Hal is halogen; R 4 is an optionally substituted aromatic radical containing 5-10 carbon atoms, an aliphatic radical containing 1-20 carbon atoms, a cycloaliphatic radical containing 5-10 carbon atoms, hydrogen or two radicals R 4 taken together with the carbon atom to which they are attached form a cycloaliphatic ring of 5-7 ring members; R 6 is an aliphatic radical containing 1-10 carbon atoms, a cycloaliphatic radical containing 5-10 carbon atoms, an aliphatic-aromatic radical containing 6-10 carbon atoms or an aromatic radical containing 5-10 carbon atoms and y is an integer of from 1 to 3.
Claim 3
Dependent Claim 27 words
The process as claimed in claim 1 wherein the reaction is carried out in a phenolic solvent or in the presence of an aliphatic alcohol or polyol.
Claim 4
Dependent Claim 19 words
The process as claimed in claim 1 wherein up to 50% of (a) is replaced by a corresponding O-alkylurethane.
Claim 5
Dependent Claim 32 words
The process as claimed in claim 1 wherein the reaction is carried out in the presence of an organic iron, lead or tin compound or iron chloride, lead oxide or lead carbonate.
Claim 6
Dependent Claim 20 words
The process as claimed in claim 1 wherein the reaction is carried out in the presence of a tertiary amine.
Claim 7
Dependent Claim 19 words
The process as claimed in claim 1 wherein 1 mol of (b) is reacted with 2/z mol of (a).
Claim 8
Dependent Claim 19 words
The process as claimed in claim 1 wherein 1 mol of (b) is reacted with 4/z mol of (a).
Claim 9
Dependent Claim 22 words
The process as claimed in claim 1 wherein 1 mol of (b) is reacted with from 2/z to 4/z mol of (a).
Claim 10
Dependent Claim 23 words
The process as claimed in claim 1 wherein (a) is tolylene diisocyanate, m-phenylene diisocyanate, polyphenylmethylene-polyisocyanate, 4,4-diisocyanato-diphenylmethane, 4,4-diisocyanato-diphenylether, 4,4-diisocyanato-diphenyldimethylmethane, p-phenylene diisocyanate or hexamethylene diisocyanate.
Claim 11
Dependent Claim 36 words
The process as claimed in claim 1 wherein (b) is chloroacetic acid, α-chlorinated or α-brominated propionic, butyric, 2-ethylhexanoic, stearic, phenylacetic, diphenylacetic, dimethylacetic, isopropylacetic, cyclohexanoic acid, α,α'-chlorinated or α,α'-brominated succinic, adipic, glutaric, sebacic or phenylene diacetic acid.
Claim 12
Dependent Claim 78 words
An oligohydantoin or polyhydantoin containing in statistical arrangement the structural unit ##EQU12## wherein R 4 is hydrogen, an optionally substituted aromatic radical containing 5-10 carbon atoms, an aliphatic radical containing 1-20 carbon atoms, a cycloaliphatic radical containing 5-10 carbon atoms or the two radicals R 4 taken together with the carbon atom to which they are attached from a cycloaliphatic ring of 5-7 ring members and R 3 is an optionally substituted aromatic radical containing 5-12 carbon atoms.
Claim 13
Dependent Claim 78 words
An oligohydantoin or polyhydantoin containing in statistical arrangement the structural unit ##EQU12## wherein R 4 is hydrogen, an optionally substituted aromatic radical containing 5-10 carbon atoms, an aliphatic radical containing 1-20 carbon atoms, a cycloaliphatic radical containing 5-10 carbon atoms or the two radicals R 4 taken together with the carbon atom to which they are attached from a cycloaliphatic ring of 5-7 ring members and R 3 is an optionally substituted aromatic radical containing 5-12 carbon atoms.
Claim 14
Dependent Claim 23 words
An oligohydantoin of claim 11 which contains isocyanate groups of the formula ##EQU13## wherein o is an integer of from 2 to 200.
Claim 15
Dependent Claim 30 words
An oligohydantoin of claim 11 which contains masked isocyanate groups of the formula ##EQU14## wherein A is an aliphatic or aromatic radical and o is an integer of from 2-200.

References Cited (Backward Citations)

US2829157A Cited
US3296208A Cited
US3397253A Cited
US3642524A Cited
US3676455A Cited
US3839354A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-06-29 1979-12-29 1980-06-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-06-29 1983-12-29 1984-06-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-06-29 1987-12-29 1988-06-29 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag