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US5068309A Expired / Lapsed US ⏱️ 0.0 years remaining

Low temperature curable dicyanate ester of dihydric phenol composition

Assignee: Huntsman Advanced Materials Americas LLC
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Filing: 1990-03-29
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Granted: 1991-11-26
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Expires: 2010-03-29
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Abstract

Abstract Cyanate esters of 4,4'-[1,3-phenylenebis (1-methylethylidene)] 2,2',6,6'-R-bisphenol when properly catalyzed, can be cured at temperatures in the range of about 250° to about 300° F. to obtain percent cyclotrimerization of the cyanate ester groups of at least 80 percent.

Inventors

  • 👤 David A. Shimp
  • 👤 Jeffrey T. Vanderlip

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 00:33
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/0622; C08G73/0638; C08G73/065; C08G73/0655; C07; C07C; C07C261/00; C07C261/02

Claims Analysis

Total Claims: 25
Claim 1
Independent Claim 86 words
A heat curable composition comprising the cyanate ester, 4,4'-[1,3-phenylenebis(1-methylethylidene)]-2,2',6,6'-R-bisphenyl cyanate, ##STR4## wherein R is independently H or C 1 to C 4 alkyl, in admixture with about 20 to about 500 weight parts per million based on the weight of metal and of the cyanate ester of a coordination metal chelate or carboxylate and about 1 to about 10 weight percent based on the weight of the cyanate ester of a compound containing an active hydrogen and having a boiling point of at least 160° C.
Claim 2
Dependent Claim 86 words
A heat curable composition comprising the cyanate ester, 4,4'-[1,3-phenylenebis(1-methylethylidene)]-2,2',6,6'-R-bisphenyl cyanate, ##STR4## wherein R is independently H or C 1 to C 4 alkyl, in admixture with about 20 to about 500 weight parts per million based on the weight of metal and of the cyanate ester of a coordination metal chelate or carboxylate and about 1 to about 10 weight percent based on the weight of the cyanate ester of a compound containing an active hydrogen and having a boiling point of at least 160° C.
Claim 3
Dependent Claim 9 words
The composition of claim 1 wherein R is H.
Claim 4
Dependent Claim 13 words
The composition of claim 1 wherein the coordination metal chelate is cobalt acetylacetonate.
Claim 5
Dependent Claim 13 words
The composition of claim 1 wherein the coordination metal carboxylate is zinc naphthenate.
Claim 6
Dependent Claim 25 words
The composition of claim 1 wherein the active hydrogen containing compound is an alkyl phenol containing 4 to 24 carbon atoms in the alkyl group.
Claim 7
Dependent Claim 12 words
The composition of claim 5 wherein the alkyl phenol is nonyl phenol.
Claim 8
Dependent Claim 43 words
The composition of claim 2 wherein the coordination metal carboxylate is zinc naphthenate in the amount of about 50 to about 150 ppm, and the active hydrogen containing compound is nonyl phenol in the amount of about 2 to about 6 weight percent.
Claim 9
Dependent Claim 117 words
A process for obtaining a cured composition which comprising heating at a temperature of about 250° F. to about 300° F. for a time sufficient to obtain at least about 80 percent cyclotrimerization of cyanate ester groups the compound 4,4'-[d1,3-phenylenebis (1-methylethylidene)] 2,2',6,6'-R-bisphenyl cyanate ##STR5## in admixture with about 20 to about 500 weight parts per million based on the weight of metal and of the cyanate ester of coordination metal chelate or carboxylate and about 1 to about 10 weight percent based on the weight of the cyanate ester of a compound containing an active hydrogen and a boiling point of at least 160° C. wherein R is independently H or C 1 to C 4 alkyl.
Claim 10
Dependent Claim 117 words
A process for obtaining a cured composition which comprising heating at a temperature of about 250° F. to about 300° F. for a time sufficient to obtain at least about 80 percent cyclotrimerization of cyanate ester groups the compound 4,4'-[d1,3-phenylenebis (1-methylethylidene)] 2,2',6,6'-R-bisphenyl cyanate ##STR5## in admixture with about 20 to about 500 weight parts per million based on the weight of metal and of the cyanate ester of coordination metal chelate or carboxylate and about 1 to about 10 weight percent based on the weight of the cyanate ester of a compound containing an active hydrogen and a boiling point of at least 160° C. wherein R is independently H or C 1 to C 4 alkyl.
Claim 11
Dependent Claim 9 words
The process of claim 8 wherein R is H.
Claim 12
Dependent Claim 15 words
The process of claim 8 wherein the percent cyclotrimerization is at least about 85 percent.
Claim 13
Dependent Claim 13 words
The process of claim 8 wherein the coordination metal chelate is cobalt acetylacetonate.
Claim 14
Dependent Claim 12 words
The process of claim 8 wherein the metal carboxylate is zinc napthenate.
Claim 15
Dependent Claim 24 words
The process of claim 8 wherein the active hydrogen compound is an alkyl phenol containing 4 to 24 carbon atoms in the alkyl groups.
Claim 16
Dependent Claim 12 words
The process of claim 13 wherein the alkyl phenol is nonyl phenol.
Claim 17
Dependent Claim 50 words
The process of claim 9 wherein the coordination metal carboxylate is zinc naphthenate in the amount of about 50 to about 150 ppm, the active hydrogen containing compound is nonylphenol in the amount of about 2 to about 6 weight percent and the percent cyclotrimerization is at least 85 percent.
Claim 18
Dependent Claim 122 words
The cured composition comprised of cyclotrimerized 4,4'-[1,3-phenylenebis(1-methylethylidene)]-2,2',6,6'-R-bisphenyl cyanate ##STR6## and about 20 to about 500 weight parts per million based on the weight of metal and of the cyanate ester of a coordination metal chelate or carboxylate and about 1 to about 10 weight percent based on the weight of the cyanate ester of a compound containing an active hydrogen and having a boiling point of at least 160° C. wherein R is independently H or C 1 to C 4 alkyl, wherein the percent cyclotrimerization is at least about 80 percent and wherein the water absorption of the cured casting is no more than about 1 weight percent based on the weight of the casting after 200 hours in boiling water.
Claim 19
Dependent Claim 122 words
The cured composition comprised of cyclotrimerized 4,4'-[1,3-phenylenebis(1-methylethylidene)]-2,2',6,6'-R-bisphenyl cyanate ##STR6## and about 20 to about 500 weight parts per million based on the weight of metal and of the cyanate ester of a coordination metal chelate or carboxylate and about 1 to about 10 weight percent based on the weight of the cyanate ester of a compound containing an active hydrogen and having a boiling point of at least 160° C. wherein R is independently H or C 1 to C 4 alkyl, wherein the percent cyclotrimerization is at least about 80 percent and wherein the water absorption of the cured casting is no more than about 1 weight percent based on the weight of the casting after 200 hours in boiling water.
Claim 20
Dependent Claim 9 words
The composition of claim 16 wherein R is H.
Claim 21
Dependent Claim 12 words
The composition of claim 16 wherein the metal chelate is cobalt acetylacetonate.
Claim 22
Dependent Claim 12 words
The composition of claim 16 wherein the metal carboxylate is zinc napthenate.
Claim 23
Dependent Claim 24 words
The composition of claim 16 wherein the active hydrogen compound is an alkyl phenol containing 4 to 24 carbon atoms in the alkyl group.
Claim 24
Dependent Claim 12 words
The composition of claim 20 wherein the alkyl phenol is nonyl phenol.
Claim 25
Dependent Claim 51 words
The composition of claim 17 wherein the coordination metal carboxylate is zinc naphthenate in the amount of about 50 to about 150 ppm, the active hydrogen containing compound is nonyl phenol in the amount of about 2 to about 6 weight percent and the percent cyclotrimerization is at least 85 percent.

References Cited (Backward Citations)

US4839442A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-11-25 1995-05-27 1995-11-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-11-25 1999-05-27 1999-11-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-11-25 2003-05-27 2003-11-26 $7700.00 Window Closed / Lapsed

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