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US3669961A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the preparation of hydroxybenzyl esters of cyanuric acid

Assignee: Goodrich Corp
•
Filing: 1969-05-27
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Granted: 1972-06-13
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Expires: 1989-05-27
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Abstract

Abstract Hydroxybenzyl-substituted isocyanurates are prepared by the condensation reaction of a phenol with cyanuric acid or a partial ester of cyanuric acid and formaldehyde. The hydroxybenzylsubstituted isocyanurates and particularly 3,5-dialkyl-4hydroxybenzyl isocyanurates and useful stabilizers for a wide variety of organic materials including olefin homopolymers and copolymers.

Inventors

  • 👤 Jack C Gilles

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 16:15
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3477

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 23 words
The process of claim 1 wherein the reaction is conducted in the presence of an organic or inorganic basic compound as a catalyst.
Claim 2
Dependent Claim 29 words
The process of claim 2 wherein (1) is a 2,6-dialkyl phenol wherein R2 and R3 are alkyl groups containing from one to 12 carbon atoms and R6 is hydrogen.
Claim 3
Dependent Claim 50 words
The process of claim 3 wherein the organic or inorganic basic compound is selected from the group consisting of primary, secondary and tertiary monoamines, primary, secondary and tertiary polyamines, alkali metal alcoholates, alkali metal hydroxides and quaternary ammonium hydroxides and the reaction temperature is between about 90* and 150* C.
Claim 4
Dependent Claim 33 words
ThE process of claim 4 wherein (1) is a 2,6-di-t-alkyl phenol wherein R2 and R3 are tertiary alkyl groups containing from four to eight carbon atoms and R4, R5 and R6 are hydrogen.
Claim 5
Dependent Claim 20 words
The process of claim 5 wherein the formaldehyde-liberating compound is selected from the group consisting of formalin, paraformaldehyde and trioxane.
Claim 6
Dependent Claim 26 words
The process of claim 6 wherein the organic diluent is selected from the group consisting of amides, N-alkyl-substituted amides, dimethyl sulfoxide, acetonitrile, propylene carbonate and N-methyl-2-pyrrolidone.
Claim 7
Dependent Claim 36 words
The process of claim 7 wherein the organic heterocyclic compound is cyanuric acid, (1) is 2,6-di-t-butyl phenol, the formaldehyde-liberating compound is paraformaldehyde and the basic compound is a polyamine containing up to about 10 carbon atoms.
Claim 8
Dependent Claim 25 words
The process of claim 8 wherein the organic diluent is acetonitrile containing up to about 25% by weight water and the basic compound is hexamethylenetetraamine.
Claim 9
Dependent Claim 25 words
The process of claim 8 wherein the organic diluent is N,N-dimethylformamide containing up to about 25% by weight water and the basic compound is hexamethylenetetraamine.
Claim 10
Dependent Claim 53 words
The process of claim 6 wherein the organic heterocyclic compound is a partial ester of cyanuric acid wherein R is an alkyl group containing from six to 18 carbon atoms, (1) is 2,6-di-t-butyl phenol, the formaldehyde-liberating compound is paraformaldehyde and the basic compound is a polyamine containing up to about 10 carbon atoms.
Claim 11
Dependent Claim 41 words
The process of claim 11 wherein the organic diluent contains up to about 25% by weight water and is selected from the group consisting of amides, N-alkyl-substituted amides, dimethyl sulfoxide, acetonitrile, propylene carbonate and N-methyl-2-pyrrolidone and the basic compound is hexamethylenetetraamine.
Claim 12
Dependent Claim 46 words
The process of claim 7 wherein the organic diluent contains up to about 25% by weight water and is selected from the group consisting of amides, N-alkyl-substituted amides, dimethyl sulfoxide, acetonitrile, propylene carbonate, and N-methyl-2-pyrrolidone and the reaction temperature is between about 90* and 150* C.
Claim 13
Dependent Claim 17 words
The process of claim 13 wherein the methylol derivative of cyanuric acid and 2,6-di-t-butyl phenol are employed.
Claim 14
Dependent Claim 19 words
The process of claim 14 wherein the basic compound is a polyamine containing up to about 10 carbon atoms.
Claim 15
Dependent Claim 34 words
The process of claim 13 wherein the methylol derivative of a partial ester of cyanuric acid wherein R is an alkyl radical containing from six to 18 carbon atoms and 2,6-di-t-butyl phenol are employed.
Claim 16
Dependent Claim 19 words
The process of claim 16 wherein the basic compound is a polyamine containing up to about 10 carbon atoms.
Claim 17
Dependent Claim 19 words
The process of claim 3 wherein the organic diluent is acetonitrile containing up to about 25% by weight water.
Claim 18
Dependent Claim 28 words
The process of claim 18 wherein (1) is 2,6-di-t-butyl phenol, the organic heterocyclic compound is cyanuric acid, the formaldehyde-liberating compound is paraformaldehyde and the basic compound is hexamethylenetetraamine.
Claim 19
Dependent Claim 49 words
The process of claim 18 wherein (1) is 2,6-di-t-butyl phenol, the organic heterocyclic compound is a partial ester of cyanuric acid wherein R is an alkyl radical containing from six to 18 carbon atoms and R1 is hydrogen, the formaldehyde-liberating compound is paraformaldehyde and the basic compound is hexamethylenetetraamine.

References Cited (Backward Citations)

US2454078A Cited
US3531483A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1975-06-13 1975-12-13 1976-06-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1979-06-13 1979-12-13 1980-06-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1983-06-13 1983-12-13 1984-06-13 $7700.00 Window Closed / Lapsed

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