US4412073A
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Isocyanurate preparation by catalytic, aminosilyl initiated cyclotrimerization of isocyanates
Assignee: Rhone Poulenc Specialites Chimiques
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Filing: 1982-02-01
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Granted: 1983-10-25
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Expires: 2002-02-01
Abstract
Abstract Monomeric or polymeric isocyanurates, e.g., polyisocyanate/polyisocyanurates, are prepared by catalytically cyclotrimerizing an isocyanate, e.g., an aliphatic or cycloaliphatic isocyanate, in the presence of an aminosilyl catalysis initiator, e.g., a mono- or diaminosilane, a silylurea or a silazane, having the structural formula: R.sub.(4-n) Si--NR'R"].sub.n (I) wherein R is a saturated or unsaturated, aliphatic, cycloaliphatic, aryl, aralkyl or alkylaryl monovalent hydrocarbon radical, or halo or cyano substituted such radical, and further wherein any two radicals R may together form a single divalent such hydrocarbon radical; R' is R, SiR 3 or an amido radical having the structural formula: ##STR1## wherein R'" is R or SiR 3 , with R being as above defined, and further wherein R', when R' is neither the amido radical nor SiR 3 , may, together with the radical R", form a single divalent such radical; R" is R, or a hydrogen atom when R' is not the amido radical; and n is either 1 or 2, but when n is 2, R' is R.
Inventors
- 👤 Jean Robin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 13:41
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/02; C08G18/022; C07; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/26; C07D251/30; C07D251/34; Y; Y10; Y10S; Y10S521/00; Y10S521/902
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
173 words
A process for the preparation of a monomeric or polymeric isocyanurate compound, comprising catalytically cyclotrimerizing an isocyanate in which the isocyanate moiety is not directly bonded to an aromatic carbon atom, in the presence of an effective amount of an aminosilyl catalysis initiator having the structural formula: R.sub.(4-n) Si--NR'R"].sub.n (I) wherein R is a saturated or unsaturated, aliphatic, cycloaliphatic, aryl, aralkyl or alkylaryl monovalent hydrocarbon radical, or halo or cyano substituted such radical, and further wherein any two radicals R may together form a single divalent such hydrocarbon radical; R' is R, SiR 3 or an amido radical having the structural formula: ##STR4## wherein R'" is R or SiR 3 , with R being as above defined, and further wherein R', when R' is neither the amido radical nor SiR 3 , may, together with the radical R", form a single divalent such radical; R" is R, or a hydrogen atom when R' is not the amido radical; and n is either 1 or 2, but when n is 2, R' is R.
Claim 2
Dependent Claim
173 words
A process for the preparation of a monomeric or polymeric isocyanurate compound, comprising catalytically cyclotrimerizing an isocyanate in which the isocyanate moiety is not directly bonded to an aromatic carbon atom, in the presence of an effective amount of an aminosilyl catalysis initiator having the structural formula: R.sub.(4-n) Si--NR'R"].sub.n (I) wherein R is a saturated or unsaturated, aliphatic, cycloaliphatic, aryl, aralkyl or alkylaryl monovalent hydrocarbon radical, or halo or cyano substituted such radical, and further wherein any two radicals R may together form a single divalent such hydrocarbon radical; R' is R, SiR 3 or an amido radical having the structural formula: ##STR4## wherein R'" is R or SiR 3 , with R being as above defined, and further wherein R', when R' is neither the amido radical nor SiR 3 , may, together with the radical R", form a single divalent such radical; R" is R, or a hydrogen atom when R' is not the amido radical; and n is either 1 or 2, but when n is 2, R' is R.
Claim 3
Dependent Claim
14 words
The process as defined by claim 1, said aminosilyl catalysis initiator being a monoaminosilane.
Claim 4
Dependent Claim
14 words
The process as defined by claim 1, said aminosilyl catalysis initiator being a diaminosilane.
Claim 5
Dependent Claim
14 words
The process as defined by claim 1, said aminosilyl catalysis initiator being a silylurea.
Claim 6
Dependent Claim
14 words
The process as defined by claim 1, said aminosilyl catalysis initiator being a silazane.
Claim 7
Dependent Claim
15 words
The process as defined by claim 1, said isocyanate starting material being an aliphatic isocyanate.
Claim 8
Dependent Claim
15 words
The process as defined by claim 1, said isocyanate starting material being a cycloaliphatic isocyanate.
Claim 9
Dependent Claim
216 words
The process as defined by claim 1, wherein the aminosilyl catalysis initiator having the structural formula (I), R is an alkyl, alkenyl, halogenoalkyl or halogenoalkenyl radical having from 1 to 5 carbon atoms and containing from 1 to 6 chlorine and/or fluorine atoms, a cycloalkyl, cycloalkenyl, halogenocycloalkyl or halogenocycloalkenyl radical having from 3 to 8 carbon atoms and containing from 1 to 4 chlorine and/or fluorine atoms, an aryl, alkylaryl or halogenoaryl radical having from 6 to 8 carbon atoms and containing from 1 to 4 chlorine and/or fluorine atoms, or a cyanoalkyl radical having from 3 to 4 carbon atoms, and further wherein any two substituents R borne by one and the same silicon atom may together from a single divalent hydrocarbon radical having 1 to 4 carbon atoms; R' is R, SiR 3 or CO(NR)--R'", wherein R'" is R or SiR 3 , with R being as above defined, and further wherein R' may, together with R, form a single alkylene radical having from 4 to 6 carbon atoms; and R" is an alkyl or alkenyl radical having from 1 to 4 carbon atoms, a cycloalkyl or cycloalkenyl radical having from 4 to 6 nuclear carbon atoms, a phenyl, tolyl or xylyl radical, or a hydrogen atom if R' is not an amido radical.
Claim 10
Dependent Claim
124 words
The process as defined by claim 1, wherein the aminosilyl catalysis initiator having the structural formula (I), R is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, α-pentyl, t-butyl, chloromethyl, dichloromethyl, α-chloroethyl, α,β-dichloroethyl, fluoromethyl, difluoromethyl, α,β-difluoroethyl, 3,3,3-trifluoropropyl, trifluorocyclopropyl, 4,4,4-trifluorobutyl, 3,3,3,4,4,5,5-heptafluoropentyl, β-cyanoethyl, γ-cyanopropyl, phenyl, p-chlorophenyl, m-chlorophenyl, 3,5-dichlorophenyl, trichlorophenyl, tetrachlorophenyl, o-, p- or m-tolyl, α,α,α-trifluorotolyl, 2,3-dimethylphenyl or 3,4-dimethylphenyl, and further wherein any two radicals R may together form a methylene, ethylene or propylene radical; R' is R, SiR 3 or --CO--(NR)--R'", with R being as above defined, and wherein R'" is R or SiR 3 , with R also being as above defined, and further wherein R' may, together with R", form a butylene, pentylene or hexylene radical; and R" is hydrogen, methyl, butyl, cyclohexyl, phenyl or tolyl.
Claim 11
Dependent Claim
74 words
The process as defined by claim 1, wherein the aminosilyl catalysis initiator having the structural formula (I), R is methyl, ethyl, propyl, vinyl or phenyl, or chlorinated and/or fluorinated such radicals; R' is methyl, ethyl, propyl, butyl, SiR 3 , --CO--NR--R or --CO--NR--SiR 3 , with R being as above defined; and R" is methyl, ethyl, propyl, butyl or hydrogen, and further wherein R' may, together with R", form a butylene or pentylene radical.
Claim 12
Dependent Claim
23 words
The process as defined by any of claims 1, 8, 9 or 10, said aminosilyl catalysis initiator having the structural formula: R.sub.3 SiNR'R".
Claim 13
Dependent Claim
23 words
The process as defined by any of claims 1, 8, 9 or 10, said aminosilyl catalysis initiator having the structural formula: R.sub.2 Si(NR'R").sub.2.
Claim 14
Dependent Claim
22 words
The process as defined by any of claims 1, 8, 9 or 10, said aminosilyl catalysis initiator having the structural formula: ##STR5##
Claim 15
Dependent Claim
22 words
The process as defined by any of claims 1, 8, 9 or 10, said aminosilyl catalysis initiator having the structural formula: ##STR6##
Claim 16
Dependent Claim
45 words
The process as defined by claim 1, for the preparation of a polyisocyanate/polyisocyanurate by catalytically cyclotrimerizing an aliphtic or cycloaliphatic polyisocyanate, or polyisocyanate adduct or prepolymer thereof, and comprising destruction of the catalysis initiator when the degree of isocyanurate formation has attained the desired level.
Claim 17
Dependent Claim
23 words
The process as defined by claim 15, said catalysis initiator destruction being effected by addition of an acid compound to the reaction medium.
Claim 18
Dependent Claim
20 words
The process as defined by claims 15 or 16, further comprising removal of residual polyisocyanate upon completion of the reaction.
Claim 19
Dependent Claim
14 words
The process as defined by claim 1, said isocyanate catalytically cyclotrimerized being hexamethylene diisocyanate.
Claim 20
Dependent Claim
33 words
The process as defined by claim 1, said aminosilyl catalysis initiator being methylamino-trimethylsilane, dimethylamino-trimethylsilane, diethylamino-trimethylsilane, dibutylamino-trimethylsilane, diethylamino-dimethyl-vinylsilane, diethylamino-dimethyl-phenylsilane, bis-dimethylamino-dimethylsilane, bis-diethylamino-dimethylsilane, bis-dibutylamino-dimethylsilane, bis-dimethylamino-methyl-phenylsilane, N-methyl-N-trimethylsilyl-N'-methyl-N'-butylurea, N-trimethylsilyl-N-methyl-N',N'-dimethylurea, N-trimethylsilyl-N-ethyl-N',N'-dimethylurea, N-trimethylsilyl-N-butyl-N'-butyl-N'-trimethylsilylurea, hexamethyldisilazane, heptamethyldisilazane, 1,3-diethyl-1,1,3,3-tetramethyldisilazane, 1,3-divinyl-1,1,3,3,-tetramethyldisilazane, hexaethyldisilazane or 1,3-diphenyl-1,1,3,3-tetramethyldisilazane.
Claim 21
Dependent Claim
32 words
The process as defined by claim 1, said isocyanate catalytically cyclotrimerized being methyl isocyanate, butyl isocyanate, n-hexyl isocyanate, cyclohexyl isocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 1,2-diisocyanatocyclohexane, 1,4-diisocyanatocyclohexane, 1,2-bis-(isocyanatomethyl)-cyclobutane, bis-(4-isocyantocyclohexyl)-methane or 3,3,5-trimethyl-5-isocyanatomethyl-1-isocyantocyclohexane.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-10-24 | 1987-04-25 | 1987-10-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-10-24 | 1991-04-25 | 1991-10-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-10-24 | 1995-04-25 | 1995-10-25 | $7700.00 | Window Closed / Lapsed |