Back to results
US 5,912,308 AGranted
Multifunctional cyanate ester and epoxy blends
AssigneeAlliedSignal Inc.
InventorsSajal Das, Geraldine Shu-Chuin Su
Life of this patent
Estimating the term…
Abstract
A curable resin blend including a multifunctional phenolic cyanate/phenolic triazine copolymer; and an epoxy resin, and articles manufactured therefrom. The cured resin blend possesses a high glass transition temperature, flexural strength, elongation, flexural modulus, compressive strength, and compressive modulus properties as well as low moisture absorption properties. The cured blend is suitable for making laminates, coatings, composites, and molds such as via resin transfer molding, compression molding, and the like.
Claims31
A blend comprising, based upon the total weight of the blend,
- a) from about 15 percent to about 50 percent of a multifunctional phenolic cyanate/phenolic triazine copolymer comprising three or more phenolic moieties of formula I:
- ##STR15## linked by way of at least one of open valences to one or more triazine moieties of the formula II:
- ##STR16## and wherein the remainder of the open valences of said phenolic moieties are substituted with --OH, --OCN, or other triazine moieties, provided that at least one of said remaining open valences is substituted with a --OCN moiety;
- wherein:
- n is about 3 to about 10;
- from, based upon the total moles of phenyl groups in said copolymer, about 5 to about 20 percent of the phenyl groups of said copolymer are substituted with --OCN groups and from about 5 to about 20 percent of said phenyl groups are substituted with --OH groups;
- q is 0;
- o is 0;
- X is a moiety selected from the group consisting of --OH.sub.2 --, --CF.sub.2 --;
- ##STR17## r is 3;
- and p is 4;
- and
- R.sub.2 and R.sub.3 are the same or different at each occurrence and are a substituent other than hydrogen which is unreactive under conditions necessary to completely cure the copolymer;
- and
- b) from about 25 percent to about 70 percent of a brominated epoxy resin having the formula ##STR18## wherein k is from about 2 to about 3, said brominated epoxy resin comprising, based upon the total weight of said brominated epoxy resin, from about 50 percent to about 70 percent bromination;
- c) from about 5 to about 10 percent of a tetrafunctional epoxy resin having the formula:
- ##STR19## d) from about 0.01 percent to about 1 percent of a manganese octoate catalyst;
- and
- e) from about 0.5 percent to about 1 percent of a 2-methyl imidazol curing agent, said blend being curable whereby said tetrafunctional epoxy resin is crosslinked with said multifunctional phenolic cyanate/phenolic triazine copolymer, and said epoxy resin is crosslinked with said multifunctional phenolic cyanate/phenolic triazine copolymer.
16 more elements
A blend comprising, based upon the total weight of the blend,
- (a) from about 15 percent to about 50 percent of a multifunctional phenolic cyanate/phenolic triazine copolymer comprising three or more phenolic moieties of formula I:
- ##STR20## linked by way of at least one of open valences to one or more triazine moieties of the formula II:
- ##STR21## and wherein the remainder of the open valences of said phenolic moieties are substituted with --OH, --OCN, or other triazine moieties, provided that at least one of said remaining open valences is substituted with a --OCN moiety;
- wherein:
- n is about 3 to about 10;
- from, based upon the total moles of phenyl groups in said copolymer, about 5 to about 20 percent of the phenyl groups of said copolymer are substituted with --OCN groups and from about 5 to about 20 percent of said phenyl groups are substituted with --OH groups;
- q is 0;
- o is 0;
- X is a moiety selected from the group consisting of --CH.sub.2 --, --CF.sub.2 --, ##STR22## r is 3;
- and p is 4;
- and
- R.sub.2 and R.sub.3 are the same or different at each occurrence and are substituent other than hydrogen which is unreactive under conditions necessary to completely cure the polymer;
- and
- (b) from about 25 percent to about 70 percent of an epoxy having the formula:
- ##STR23## wherein R is ##STR24## wherein said blend, upon being cured, has a glass transition temperature of at least about 200.degree. C. (392.degree. F.) and a water absorption rate of about 0.32 percent water after 24 hours immersion at room temperature;
- blended with at least one catalyst selected from the group consisting of lead naphthenate, manganese naphthenate, manganese octoate, manganic acetylacetonate, cobalt octoate, cobalt naphthenate, cobalt acetylacetonate, zinc octoate, zinc naphthenate, zinc acetylacetonate, copper acetylacetonate, cupric naphthenate, nickel acetylacetonate, titanyl acetylacetonate, ferric octoate, tin octoate, diazobicyclo2.2.2!-octane, catechol, 1,1-dimethyl-3-phenylurea, nonylphenole, 1-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, and 2-methylimidazole, said blend being curable wherein said epoxy resin (b) is crosslinked with said multifunctional phenolic cyanate/phenolic triazine copolymer
13 more elements
A blend comprising:
- (a) a multifunctional phenolic cyanate/phenolic triazine copolymer comprising three or more phenolic moieties of formula I:
- ##STR25## linked by way of at least one of open valences to one or more triazine moieties of the formula II:
- ##STR26## and wherein the remainder of the open valences of said phenolic moieties are substituted with --OH, --OCN, or other triazine moieties, provided that at least one of said remaining open valences is substituted with a --OCN moiety, wherein:
- n is a positive whole number equal to or greater than 1,
- q and r are the same or different at each occurrence and are whole numbers from 0 to 3 with the proviso that the sum of q and r at each occurrence is equal to 3,
- o and p are the same or different at each occurrence and are whole numbers from 0 to 4, with the proviso that the sum of o and p is equal to 4,
- --X-- is a divalent organic radical;
- and
- R.sub.3 is the same or different at each occurrence and is a substituent other than hydrogen which is unreactive under conditions necessary to completely cure the copolymer;
- and
- (b) an epoxy resin selected from the group consisting of bisphenol-A-based epoxy resins, halogenated epoxy resins, epoxy novolac resins, polyglycol epoxy resins, multifunctional epoxy resins, mixtures thereof and copolymers thereof, said blend comprising, based upon the total weight of the blend, from about 5 to about 95 weight percent of said multifunctional phenolic cyanate/phenolic triazine copolymer and from about 5 to about 95 percent of said epoxy resin;
- blended with at least one catalyst selected from the group consisting of lead naphthenate, manganese naphthenate, manganese octoate, manganic acetylacetonate, cobalt octoate, cobalt naphthenate, cobalt acetylacetonate, zinc octoate, zinc naphthenate, zinc acetylacetonate, copper acetylacetonate, cupric naphthenate, nickel acetylacetonate, titanyl acetylacetonate, ferric octoate, tin octoate, diazobicyclo2.2.2!octane, catechol, 1,1-dimethyl-3-phenylurea, nonylphenol, 1-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-methylimidazole, and mixtures thereof.
9 more elements
A blend comprising:
- (a) a multifunctional phenolic cyanate/phenolic triazine copolymer comprising three or more phenolic moieties of formula I:
- ##STR31## linked by way of at least one of open valences to one or more triazine moieties of the formula II:
- ##STR32## and wherein the remainder of the open valences of said phenolic moieties are substituted with --OH, --OCN, or other triazine moieties, provided that at least one of said remaining open valences is substituted with a --OCN moiety, wherein:
- n is a positive whole number equal to or greater than 1,
- q and r are the same or different at each occurrence and are whole numbers from 0 to 3 with the proviso that the sum of q and r at each occurrence is equal to 3,
- o and p are the same or different at each occurrence and are whole numbers from 0 to 4, with the proviso that the sum of o and p is equal to 4,
- --X-- is a divalent organic radical;
- and
- R.sub.3 is the same or different at each occurrence and is a substituent other than hydrogen which is unreactive under conditions necessary to completely cure the copolymer;
- and
- (b) an epoxy resin selected from the group consisting of the compounds having the following formulas:
- ##STR33## wherein m is from about 0.1 to about 1, ##STR34## wherein k is from about 2 to about 3, ##STR35## wherein I is from about 0.1 to about 2, ##STR36## wherein j is from about 1 to about 2 and R' is an organic group or hydrogen, tetra-functional epoxy resins, tri-functional epoxy resins, mixtures thereof and combinations thereof, said blend comprising, based upon the total weight of the blend, from about 5 to about 95 weight percent of said multifunctional phenolic cyanate/phenolic triazine copolymer and from about 5 to about 95 weight percent of said epoxy resin;
- blended with at least one catalyst selected from the group consisting of lead naphthenate, manganese naphthenate, manganese octoate, manganic acetylacetonate, cobalt octoate, cobalt naphthenate, cobalt acetylacetonate, zinc octoate, zinc naphthenate, zinc acetylacetonate, copper acetylacetonate, cupric naphthenate, nickel acetylacetonate, titanyl acetylacetonate, ferric octoate, tin octoate, diazobicyclo2.2.2.!octane, catechol, 1,1-dimethyl-3-phenylurea, nonylphenol, 1-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-methylimidazole, and mixtures thereof.
10 more elements
Dependencies are inferred from the claim text.