US 6,645,631 B2 · Flame retardant phosphorus element-containing epoxy resin compositions

Abstract

A flame retardant phosphorus element-containing epoxy resin composition substantially free of halogen, including: (I) a non-halogenated epoxy resin material selected from: (A) a non-halogenated phosphorus element-containing epoxy resin; (B) a mixture of: (1) a non-halogenated, non-phosphorus element-containing epoxy resin, and (2) a phosphorus element-containing compound; or (C) the reaction product of: (1) a non-halogenated epoxy resin; and (2) a phosphorus element-containing compound; or (D) a combination of two or more of components (A) to (C); and (II) (A) a multi-functional phenolic crosslinking agent having a hydroxy functionality of at least 2; (B) a material which forms a multifunctional phenolic crosslinking agent having a hydroxy functionality of at least 2, upon heating or (C) a mixture of components (A) and (B); in an amount of from about 50% to about 150% of the stoichiometric amount needed to cure the epoxy resin. Electrical laminate circuit boards having reduced flammability may be made from these compositions.

Claims39

Dependent claims

A flame retardant phosphorus element-containtng epoxy resin composition substantially free of halogen, comprising:

(I) a non-halogenated epoxy resin material selected from:
(A) a non-halogenated, phosphorus element-containing epoxy resin;
wherein the non-halogenated, phosphorus element-containing epoxy resin is a reaction product of:
(1) an epoxy novolac, an epoxy of tris(hydroxyphenyl)methane, a cresol epoxy novolac, a dicyclopentadiene modified phenol epoxy novolac, a glycidyl of tetraphenol ethane, a diglycidyl ether of bisphenol-A, a diglycidyl ether of bisphenol-F, or mixture thereof;
and (2) 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide;
10-(2′,5′-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide;
bis(4-hydroxyphenyl)phosphine oxide;
tris(2-hydroxyphenyl)phosphine oxide;
dimethyl-1-bis(4-hydroxyphenyl)-1-phenylmethylphonate;
tris(2-hydroxy-4/5-methylphenyl)phosphine oxide;
dimethyl phosphite;
vinyl phosphonic acid;
tris(4-hydroxyphenyl)phosphine oxide;
bis(2-hydroxyphenyl)phenylphosphine oxide;
bis(2-hydroxyphenyl)phenylphosphinate;
tris(2-hydroxy-5-methylphenyl)phosphine oxide;
or mixtures thereof;
(B) a combination of (3) Component (A) and (4) a blend of:
(a) a non-halogenated, non-phosphorus element-containing epoxy resin, and
(b) a phosphorus element-containing compound;
(C) a combination of (S) Component (A) and (6) the reaction product of:
(c) a non-halogenated epoxy resin;
and
(d) a phosphorus element-containing compound;
or
(D) a combination of two or more of Components (A) to (C);
(II)
(E) a multi-functional phenolic crosslinking agent having a hydroxy functionality of at least 2;
(F) a material which forms a multi-functional phenolic crosslinking agent having a hydroxy functionality of at least 2 upon heating;
or
(G) a mixture of Components (E) and (F);
and
(IV) a Lewis acid.

30 more elements

A flame retardant phosphorus element-containing epoxy resin composition substantially free of halogen, comprising:

(I) a non-halogenated epoxy resin material selected from:
(A) a non-halogenated, phosphorus element-containing epoxy resin;
wherein the non-halogenated, phosphorus element-containing epoxy resin is a reaction product of:
(1) an epoxy novolac, an epoxy of tris(hydroxyphenyl)methane, a cresol epoxy novolac, a dicyclopentadiene modified phenol epoxy novolac, a glycidyl of tetraphenol ethane, a diglycidyl ether of bisphenol-A, a diglycidyl ether of bisphenol-F, or a mixture thereof;
and (2)9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide;
10-(2′,5′-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide;
bis(4-hydroxyphenyl)phosphine oxide;
tris(2-hydroxyphenyl)phosphine oxide;
dimethyl-1-bis(4-hydroxyphenyl)-1-phenylmethylphonate;
tris(2-hydroxy-4/5-methylphenyl)phosphine oxide;
dimethyl phosphite;
vinyl phosphonic acid;
tris(4-hydroxyphenyl)phosphine oxide;
bis(2-hydroxyphenyl)phenylphosphine oxide;
bis(2-hydroxyphenyl)phenylphosphinate;
tris(2-hydroxyl-5-methylphenyl)phosphine oxide;
or mixtures thereof;
(B) a combination of (3) Component (A) and (4) a blend of:
(a) a non-halogenated, non-phosphorus element-containing epoxy resin, and
(b) a phosphorus element-containing compound;
(C) a combination of (5) Component (A) and (6) the reaction product of:
(c) a non-halogenated epoxy resin;
and
(d) a phosphorus element-containing compound;
or
(D) a combination of two or more of Components (A) to (C);
(II)
(E) a multi-functional phenolic crosslinking agent having a hydroxy functionality of at least 2;
(F) a material which forms a multi-functional phenolic crosslinking agent having a hydroxy functionality of at least 2 upon heating;
or
(G) a mixture of Components (E) and (F);
and
(III) a catalyst capable of promoting the reaction of the phenolic/hydroxy group of the multi-functional phenolic crosslinking agent with the epoxy group of the epoxy resin material, wherein the catalyst is an amine catalyst compound.

30 more elements

A flame retardant phosphorus element-containing epoxy resin composition substantially free of halogen, comprising:

(I) a non-halogenated epoxy resin material selected from:
(A) a non-halogenated, phosphorus element-containing epoxy resin;
wherein the non-halogenated, phosphorus element-containing epoxy resin is a reaction product of:
(1) an epoxy novolac, an epoxy of tris(hydroxyphenyl)methane, a cresol epoxy novolac, a dicyclopentadiene modified phenol epoxy novolac, a glycidyl of tetraphenol ethane, a diglycidyl ether of bisphenol-A, a diglycidyl ether of bisphenol-F, or a mixture thereof;
and (2) 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide;
10-(2′,5′-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide;
bis(4-hydroxyphenyl)phosphine oxide;
tris(2-hydroxylphenyl)phosphine oxide;
dimethyl-1-bis(4-hydroxyphenyl)-1-phenylmethylphonate;
tris(2-hydroxy-4/5-methylphenyl)phosphine oxide;
dimethyl phosphite;
vinyl phosphonic acid;
tris(4-hydroxyphenyl)phosphine oxide;
bis(2-hydroxyphenyl)phenylphosphine oxide;
bis(2-hydroxyphenyl)phenylphosphinate;
tris(2-hydroxy-5-methylphenyl)phosphine oxide;
or mixtures thereof;
(B) a combination of (3) Component (A) and (4) a blend of:
(a) a non-halogenated, non-phosphorus element-containing epoxy resin, and
(b) a phosphorus element-containing compound;
(C) a combination of (5) Component (A) and (6) the reaction product of:
(c) a non-halogenated epoxy resin;
and
(d) a phosphorus element-containing compound;
or
(D) a combination of two or more of Components (A) to (C);
(II)
(E) a multi-functional phenolic crosslinking agent having a hydroxy functionality of at least 2;
(F) a material which forms a multi-functional phenolic crosslinking agent having a hydroxy functionality of at least 2 upon heating;
or
(G) a mixture of Components (E) and (F);
and
(V) a flame-retardant additive.

30 more elements

A flame retardant phosphorus element-containing epoxy resin composition substantially free of halogen, comprising:

(I) a non-halogenated epoxy resin material selected from:
(A) a non-halogenated, phosphorus element-containing epoxy resin;
wherein the non-halogenated, phosphorus element-containing epoxy resin is a reaction product of:
(1) an epoxy novolac, an epoxy of tris(hydroxyphenyl)methane, a cresol epoxy novolac, a dicyclopentadiene modified phenol epoxy novolac, a glycidyl of tetraphenol ethane, a diglycidyl ether of bisphenol-A, a diglycidyl ether of bisphenol-F, or mixture thereof;
and (2)9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide;
10-(2′,5′-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide;
bis(4-hydroxyphenyl)phosphine oxide;
tris(2-hydroxyphenyl)phosphine oxide;
dimethyl-1-bis(4-hydroxyphenyl)-1-phenylmethylphonate;
tris(2-hydroxy-4/5-methylphenyl)phosphine oxide;
dimethyl phosphite;
vinyl phosphonic acid;
tris(4-hydroxyphenyl)phosphine oxide;
bis(2-hydroxyphenyl)phenylphosphine oxide;
bis(2-hydroxyphenyl)phenylphosphinate;
tris(2-hydroxy-5-methylphenyl)phosphine oxide;
or mixtures thereof;
(B) a combination of (3) Component (A) and (4) a blend of:
(a) a non-halogenated, non-phosphorus element-containing epoxy resin, and
(b) a phosphorus element-containing compound;
(C) a combination of (5) Component (A) and (6) the reaction product of:
(c) a non-halogenated epoxy resin;
and
(d) a phosphorus element-containing compound;
or
(D) a combination of two or more of Components (A) to (C);
(II)
(E) a multi-functional phenolic crosslinking agent having a hydroxy functionality of at least 2;
(F) a material which forms a multi-functional phenolic crosslinking agent having a hydroxy functionality of at least 2 upon heating;
or
(G) a mixture of Components (E) and (F);
and
(VII) a multi-functional co-crosslinking agent different from the multi-functional phenolic crosslinking agent (II).

30 more elements

Dependencies are inferred from the claim text.

Flame retardant phosphorus element-containing epoxy resin compositions

Life of this patent

Flame retardant phosphorus element-containing epoxy resin compositions

Life of this patent

Abstract

Claims39