Phosphorus element-containing crosslinking agents and flame retardant phosphorus element-containing epoxy resin compositions prepared therewith
View Patent ↗Novel phosphorus element-containing vinyl ester resin compositions and process for preparing epoxy vinyl ester resin compositions include non-halogenated, ignition resistant epoxy vinyl ester resin formulations. The ignition resistant epoxy vinyl ester resin formulations are advantageously used for making laminates for printed wiring boards and composite materials.
1. A vinyl ester resin composition comprising a compound having the following chemical structure of Formula VIII:
wherein R in Formula VIII is independently a hydrogen or a C 1 -C 40 alkyl group and R 1 is an unsaturated functionality.
2. The composition of claim 1 wherein R is hydrogen.
3. The composition of claim 1 wherein R is a methyl group.
4. The composition of claim 3 wherein R is in the 5 position of the phenyl ring.
5. The composition of claim 1 wherein R 1 is a moiety having the following formula:
where R″ is a hydrogen or an alkyl group from C 1 -C 20 and R′″ is hydrogen, an alkyl group from C 1 -C 20 , or a carboxylic acid group or ester derivatives thereof.
6. The composition of claim 5 wherein R 1 is a methacrylate, an acrylate, a maleate, or a fumarate.
7. A process for preparing an epoxy vinyl ester resin comprising reacting (a) a compound of Formula V
wherein R in Formula V is independently a hydrogen or a C 1 -C 10 allyl group, with (b) a carboxylic acid which contains an unsaturated functionality to produce the compound as shown in the following chemical structure of Formula VIII:
wherein R in Formula VIII is independently a hydrogen or a C 1 -C 10 allyl group and R 1 is a moiety containing an unsaturated functionality.
8. The process of claim 7 wherein the composition of Formula V is an isomer mixture of two or more different triaryl phosphine oxide isomer compounds having the general chemical structural formula of Formula V:
wherein R is a methyl group.
9. The process of claim 8 wherein at least one of the isomers in the isomeric mixture contains a 2-glycidyloxy-4-methyphenyl moiety.
10. The process of claim 8 wherein at least one of the isomers in the isomeric mixture contains 2-glycidyloxy-5-methylphenyl moiety.
11. The process of claim 8 wherein the isomeric mixture contains at least a mixture of a 2-glycidyloxy 4-methyipheflyl moiety and a 2-glycidyloxy-5-methylphenyl moiety.
12. The process of claim 11 wherein the ratio of 2-glycidyloxy 4-methyipheflyl moiety to 2-glycidyloxy-5-methylphenyl moiety is from about 99:1 to about 1:99.
13. The process of claim 7 wherein the carboxylic acid is an acrylic acid, a methacrylic acid, a maleic acid or a furmaric acid.