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US5068309A
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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
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 03:54
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 |