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US4011180A Expired / Lapsed US ⏱️ 0.0 years remaining

Novel cocatalyst system for trimerizing polyisocyanates

Assignee: Pharmacia and Upjohn Co
•
Filing: 1975-05-02
•
Granted: 1977-03-08
•
Expires: 1995-05-02
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Abstract

Abstract A novel catalyst combination for the trimerization of polyisocyanates to polyisocyanurates is disclosed. The catalyst combination comprises (i) an alkali metal salt of an N-substituted amide, (ii) an alkali metal salt of an N-(2-hydroxyphenyl)methyl glycine, and optionally a tertiary amine trimerization catalyst. The use of these catalyst combinations in the preparation of polyisocyanurate foams results in the facile continuous formation of laminate board stock. The polyisocyanurate foams produced using the novel catalyst combinations of the invention are characterized by having high resistance to heat distortion and volume change.

Inventors

  • 👤 Robert J. Lockwood
  • 👤 Harold E. Reymore, Jr.
  • 👤 Edward J. Thompson

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 20:07
CPC Classifications
B; B32; B32B; B32B15/00; B32B15/04; B32B15/046; B32B5/00; B32B5/18; B32B5/20; B32B15/20; C; C08; C08G; C08G12/00; C08G12/02; C08G18/00; C08G18/02; C08G18/022; B32B2307/00; B32B2307/30; B32B2307/306; B32B2311/00; B32B2311/24; Y; Y10; Y10S; Y10S521/00; Y10S521/902; Y10T; Y10T428/00; Y10T428/249921; Y10T428/249953; Y10T428/249982; Y10T428/249984

Claims Analysis

Total Claims: 28
Claim 1
Independent Claim 224 words
In a process for the preparation of a cellular polymer in which the major recurring polymer unit is isocyanurate which process comprises bringing together in the presence of a blowing agent, a polyisocyanate, a trimerization catalyst, and from about 0.01 equivalent to about 0.3 equivalent of a polyol per equivalent of isocyanate, the improvement which consists essentially of employing as the catalyst, a combination of the following ingredients: a. from 0.00075 to 0.03 equivalent per equivalent of said polyisocyanate of an amide salt having the formula ##STR12## wherein M is an alkali metal, R 1 , R 2 and R 3 can be the same or different and are selected from the group consisting of H, lower alkyl, aryl, aralkyl, and cycloalkyl, and R 4 is selected from the group consisting of lower alkyl and aryl; and b. from 0.0015 to 0.025 equivalent per equivalent of said polyisocyanate of a glycine salt having the formula ##STR13## wherein M is an alkali metal, R 5 is selected from the class consisting of hydrogen and alkyl having from 1 to 12 carbon atoms, inclusive, R 6 is selected from the class consisting of hydrogen, alkyl having from 1 to 12 carbon atoms, inclusive and --CH 2 --COO -M + , and R 7 is selected from the class consisting of hydrogen and the group ##STR14## .
Claim 2
Dependent Claim 224 words
In a process for the preparation of a cellular polymer in which the major recurring polymer unit is isocyanurate which process comprises bringing together in the presence of a blowing agent, a polyisocyanate, a trimerization catalyst, and from about 0.01 equivalent to about 0.3 equivalent of a polyol per equivalent of isocyanate, the improvement which consists essentially of employing as the catalyst, a combination of the following ingredients: a. from 0.00075 to 0.03 equivalent per equivalent of said polyisocyanate of an amide salt having the formula ##STR12## wherein M is an alkali metal, R 1 , R 2 and R 3 can be the same or different and are selected from the group consisting of H, lower alkyl, aryl, aralkyl, and cycloalkyl, and R 4 is selected from the group consisting of lower alkyl and aryl; and b. from 0.0015 to 0.025 equivalent per equivalent of said polyisocyanate of a glycine salt having the formula ##STR13## wherein M is an alkali metal, R 5 is selected from the class consisting of hydrogen and alkyl having from 1 to 12 carbon atoms, inclusive, R 6 is selected from the class consisting of hydrogen, alkyl having from 1 to 12 carbon atoms, inclusive and --CH 2 --COO -M + , and R 7 is selected from the class consisting of hydrogen and the group ##STR14## .
Claim 3
Dependent Claim 19 words
The process according to claim 1 wherein a monomeric polyepoxide is present in the polymer foam forming reaction mixture.
Claim 4
Dependent Claim 52 words
The process according to claim 2 wherein the catalyst combination also contains from 0.0008 to 0.03 equivalent per equivalent of said polyisocyanate of a tertiary amine trimerization catalyst selected from the group consisting of N,N-dialkylpiperazines, trialkylamines, 1,4-diazabicyclooctane, N,N',N"-tris(dialkylaminoalkyl)hexahydrotriazines, mono-, di-, and tri-(dialkylaminoalkyl)monohydric phenols or thiophenols, N,N,N',N'-tetraalkylalkylenediamines, N,N-dialkylcyclohexylamines, N-alkylmorpholines, N,N-dialkylalkanolamines, and N,N,N',N'-tetraalkyl guanidines.
Claim 5
Dependent Claim 27 words
The process according to claim 1 wherein said polyisocyanate is polymethylene polyphenyl isocyanate containing about 30 percent to about 35 percent by weight of methylenebis (phenyl isocyanate).
Claim 6
Dependent Claim 17 words
the process according to claim 1 wherein the polyisocyanate has an acidity less than about 0.10 percent.
Claim 7
Dependent Claim 45 words
The process according to claim 1 wherein the polyisocyanate has been previously mixed at room temperature with about 0.25 equivalent to about 1.0 equivalent of a monomeric epoxide per equivalent of acid present in said polyisocyanate to reduce acidity to less than about 0.10 percent.
Claim 8
Dependent Claim 12 words
The process according to claim 6 wherein said epoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate.
Claim 9
Dependent Claim 13 words
The process according to claim 1 wherein the amide salt is potassium N-phenyl-2-ethyl-hexamide.
Claim 10
Dependent Claim 14 words
The process according to claim 1 wherein the glycine salt is sodium N-(2-hydroxy-5-nonylphenyl)methyl-N-methyl glycinate.
Claim 11
Dependent Claim 32 words
The process according to claim 1 wherein the amide salt is present in the form of a solution containing from about 25 percent to about 75 percent by weight in a diluent.
Claim 12
Dependent Claim 17 words
The process according to Claim 10 wherein said diluent is a mixture of ethylene glycol and dimethyl-formamide.
Claim 13
Dependent Claim 28 words
The process according to claim 1 wherein said glycinate is present in the form of a solution from about 25 percent to about 75 percent in a diluent.
Claim 14
Dependent Claim 12 words
The process according to Claim 12 wherein said diluent is diethylene glycol.
Claim 15
Dependent Claim 97 words
In a process for the preparation of a cellular polymer in which the major recurring polymer unit is isocyanurate which process comprises bringing together in the presence of a blowing agent, a polyisocyanate, a trimerization catalyst, and from about 0.01 equivalent to about 0.3 equivalent of a polyol per equivalent of isocyanate, the improvement which consists essentially of employing as the catalyst, a combination of the following ingredients: a. from 0.00075 to 0.03 equivalent per equivalent of said polyisocyanate of potassium N-phenyl-2-ethylhexamide; and b. from 0.0015 to 0.025 equivalent per equivalent of said polyisocyanate of sodium N-(2-hydroxy-5-nonylphenyl)methyl-N-methylglycinate.
Claim 16
Dependent Claim 97 words
In a process for the preparation of a cellular polymer in which the major recurring polymer unit is isocyanurate which process comprises bringing together in the presence of a blowing agent, a polyisocyanate, a trimerization catalyst, and from about 0.01 equivalent to about 0.3 equivalent of a polyol per equivalent of isocyanate, the improvement which consists essentially of employing as the catalyst, a combination of the following ingredients: a. from 0.00075 to 0.03 equivalent per equivalent of said polyisocyanate of potassium N-phenyl-2-ethylhexamide; and b. from 0.0015 to 0.025 equivalent per equivalent of said polyisocyanate of sodium N-(2-hydroxy-5-nonylphenyl)methyl-N-methylglycinate.
Claim 17
Dependent Claim 25 words
The process according to claim 14 wherein there is also present a glycidyl ether of a novolac resin having a functionality of at least two.
Claim 18
Dependent Claim 24 words
The process according to claim 15 wherein the catalyst combination also contains from 0.0008 to 0.03 equivalent per equivalent of said polyisocyanate of N-ethylmorpholine.
Claim 19
Dependent Claim 24 words
The process according to claim 15 wherein the catalyst combination also contains from 0.0008 to 0.03 equivalent per equivalent of said polyisocyanate of N,N-dimethylcyclohexylamine.
Claim 20
Dependent Claim 28 words
The process according to Claim 14 wherein the polyisocyanate is polymethylene polyphenyl isocyanate containing from about 30 percent to about 85 percent by weight of methylenebis (phenyl isocyanate).
Claim 21
Dependent Claim 17 words
The process according to Claim 18 wherein said polyisocyanate has an acidity less than about 0.10 percent.
Claim 22
Dependent Claim 45 words
The process according to Claim 18 wherein said polyisocyanate has been previously mixed at room temperature with about 0.25 equivalent to about 1.0 equivalent of a monomeric epoxide per equivalent of acid present in said polyisocyanate to reduce acidity to less than about 0.10 percent.
Claim 23
Dependent Claim 13 words
The process according to claim 20 wherein said monomeric epoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate.
Claim 24
Dependent Claim 31 words
The process according to claim 14 wherein said amide salt is present in the form of a solution from about 25 percent to about 75 percent by weight in a diluent.
Claim 25
Dependent Claim 17 words
The process according to claim 22 wherein said diluent is a mixture of ethylene glycol and dimethylformamide.
Claim 26
Dependent Claim 30 words
The process according to claim 14 wherein said glycinate is present in the form of a solution from about 25 percent to about 75 percent by weight in a diluent.
Claim 27
Dependent Claim 12 words
The process according to claim 24 wherein said diluent is diethylene glycol.
Claim 28
Dependent Claim 23 words
The process according to claim 14 wherein said polyol is a polyoxyalkylene glycol having a molecular weight from about 200 to about 600.

References Cited (Backward Citations)

US3516950A Cited
US3801421A Cited
US3814659A Cited
US3903346A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-03-07 1980-09-06 1981-03-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-03-07 1984-09-06 1985-03-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-03-07 1988-09-06 1989-03-08 $7700.00 Window Closed / Lapsed

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