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US 10,494,520 B2Granted
Benzoxazine low temperature curable composition
AssigneeHuntsman Advanced Materials Americas LLC
InventorsDong Wang, Bradley Rechichar, Derek S. Kincaid, Ronald C. Smith, Jr.
Life of this patent
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Abstract
The present disclosure provides an organic sulfur acid-free composition containing a benzoxazine, phenolic compound and nitrogen-containing heterocyclic compound. The organic sulfur acid-free composition, upon curing at temperatures as low as 130°-140° C., renders void free cured articles having well balanced thermal, chemical and mechanical properties. The organic sulfur acid-free composition may be used in a variety of applications, such as in coatings, structural and non-structural composites and encapsulating systems for electronic and electrical components.
Claims6
An organic sulfur acid-free composition comprising:
- (a) a benzoxazine compound comprising
- (i) a compound of the formula
- where b is an integer from 1 to 4;
- each R is independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C2-C20 heterocyclic group or a C3-C8 cycloalkyl group;
- each R1 is independently hydrogen, a C1-C20 alkyl group, a C2-C20 alkenyl group or a C6-C20 aryl group;
- and Z is a direct bond when b=2, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, O, S, S═O, O═S=O or C═O,
- (ii) a compound having the formula
- where Y is a C1-C20 alkyl group, a C2-C20 alkenyl group or substituted or unsubstituted phenyl;
- and R2 is hydrogen, halogen, a C1-C20 alkyl group or a C2-C20 alkenyl group, or
- (iii) a compound having the formula
- where R2 is a C1-C20 alkyl group or a C2-C20 alkenyl group, each of which is optionally substituted or interrupted by one or more O, N, S, C═O, COO, NHC═O or a C6-C20 aryl group;
- and R3 is hydrogen, a C1-C20 alkyl group or a C2-C20 alkenyl group, each of which is optionally substituted or interrupted by one or more O, N, S, C═O, COOH, NHC═O or a C6-C20 aryl group;
- (b) a phenolic compound comprising
- (i) a monofunctional compound having the formula
- where each X is independently hydrogen, halogen, a hydrocarbyl group having from 1 to 20 carbon atoms or a hydrocarbyloxy group having from 1 to 20 carbon atoms,
- (ii) a difunctional compound having the formula
- where each X1 is independently hydrogen, a C1-C20 alkyl group, an alkoxy group, an alloxy group or a halogen;
- and R4 is a direct bond, a C1-C20 alkyl group,
- —O—, —S—, —S—S—, —S(═O), —(O=)S(═O)—, —C(═O)—, —NHC(═O)— or NHC(═O)—O—, or
- (iii) a multifunctional phenolic compound comprising a novolac resin;
- and
- (c) a nitrogen-containing heterocyclic compound comprising an imidazole, imidazolidine, imidazoline, oxazole, pyrrole, thiazole, pyridine, pyrazine, morpholine, pyridazine, pyrimidine, pyrrolidine, pyrazole, phthalozine, quinoline, purine, indazole, indole, pyrroline, indoline, piperidine, piperazine or a combination thereof.
19 more elements
An organic sulfur acid-free composition comprising:
- (a) about 10% by weight to about 98% by weight of a benzoxazine resin comprising
- (i) a compound of the formula
- where b is an integer from 1 to 4;
- each R is independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C2-C20 heterocyclic group or a C3-C8 cycloalkyl group;
- each R1 is independently hydrogen, a C1-C20 alkyl group, a C2-C20 alkenyl group or a C6-C20 aryl group;
- and Z is a direct bond when b=2, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, O, S, S═O, O=S=O or C═O,
- (ii) a compound having the formula
- where Y is a C1-C20 alkyl group, a C2-C20 alkenyl group or substituted or unsubstituted phenyl;
- and R2 is hydrogen, halogen, a C1-C20 alkyl group or a C2-C20 alkenyl group, or
- (iii) a compound having the formula
- where R2 is a C1-C20 alkyl group or a C2-C20 alkenyl group, each of which is optionally substituted or interrupted by one or more O, N, S, C═O, COO, NHC═O or a C6-C20 aryl group;
- and R3 is hydrogen, a C1-C20 alkyl group or a C2-C20 alkenyl group, each of which is optionally substituted or interrupted by one or more O, N, S, C═O, COOH and NHC═O, or a C6-C20 aryl group;
- (b) greater than 3% by weight to about 60% by weight of a phenolic compound comprising (i) a monofunctional compound having the formula
- where each X is independently hydrogen, halogen, a hydrocarbyl group having from 1 to 20 carbon atoms or a hydrocarbyloxy group having from 1 to 20 carbon atoms,
- (ii) a difunctional compound having the formula
- where each X1 is independently hydrogen, a C1-C20 alkyl group, an alkoxy group, an alloxy group or a halogen;
- and R4 is a direct bond, a C1-C20 alkyl group,
- —O—, —S—, —S—S—, —S(═O), —(O=)S(═O)—, —C(═O)—, —NHC(═O)— or NHC(═O)—O—, or
- (iii) a multifunctional phenolic compound comprising a novolac resin;
- and
- (c) about 0.01% by weight to about 30% by weight of a nitrogen-containing heterocyclic compound comprising an imidazole, imidazolidine, imidazoline, oxazole, pyrrole, thiazole, pyridine, pyrazine, morpholine, pyridazine, pyrimidine, pyrrolidine, pyrazole, phthalozine, quinoline, purine, indazole, indole, pyrroline, indoline, piperidine, piperazine or a combination thereof,
- wherein the % by weight is based on the total weight of composition.
19 more elements
Dependencies are inferred from the claim text.