Curable silicone composition and cured product thereof
A curable silicone composition is provided. The composition comprises: (A) an epoxy-functional silicone resin having monovalent aromatic hydrocarbon groups; (B) an epoxy-functional silicone; and (C) a mixture of cationic photoinitiators comprising: (C-1) an iodonium salt type cationic photoinitiator and (C-2) a sulfonium salt type cationic photoinitiator. The composition has excellent curability with UV radiation, and further with heating, generally forms a cured product with excellent transparency.
1 . A curable silicone composition comprising:
(A) an epoxy-functional silicone resin represented by the following average unit formula:
(R 1 3 SiO 1/2 ) a (R 1 2 SiO 2/2 ) b (R 1 SiO 3/2 ) c (SiO 4/2 ) d
wherein each R 1 is the same or different organic group selected from a C 1-6 monovalent aliphatic hydrocarbon group, a C 6-10 monovalent aromatic hydrocarbon group, and a monovalent epoxy-substituted organic group, provided that at least about 15 mol % of the total R 1 are the C 6-10 monovalent aromatic hydrocarbon groups; and “a”, “b”, “c” and “d” are numbers that satisfy the following conditions: 0≤a<0.4, 0<b<0.5, 0<c<1, 0≤d<0.4, 0.1≤b/c≤0.6, and a+b+c+d=1; and about 2 to about 30 mol % of the total siloxane units have the monovalent epoxy-substituted organic groups;
(B) an epoxy-functional silicone represented by the following general formula:
X 1 -R 2 2 SiO(SiR 2 2 O) m SiR 2 2 -X 1
wherein each R 2 is the same or different organic group selected from a C 1-6 monovalent aliphatic hydrocarbon group and a C 6-10 monovalent aromatic hydrocarbon group; each X 1 is the same or different group selected from a monovalent epoxy-substituted organic group and an epoxy-functional siloxy group represented by the following general formula:
X 2 -R 3 2 SiO(SiR 3 2 O) x SiR 3 2 -R 4 -
wherein each R 3 is the same or different C 1-6 monovalent aliphatic hydrocarbon group; R 4 is a C 2-6 alkylene group; X 2 is a monovalent epoxy-substituted organic group; “x” is a number of from about 0 to about 5; and “m” is a number of from about 0 to about 100, in an amount of from about 5 mass % to about 40 mass % of the total mass of components (A), (B) and (C); and
(C) a mixture of cationic photoinitiators comprising:
(C-1) an iodonium salt type cationic photoinitiator; and
(C-2) a sulfonium salt type cationic photoinitiator; in an amount of from about 0.2 mass % to about 2 mass % of the total mass of components (A), (B) and (C);
wherein component (C-1) comprises (c1) 4-isopropyl-4′-methyldiphenyliodonium tetrakis(pentafluorophenyl) borate salt represented by the following formula:
and
wherein component (C-2) comprises at least one of (c2) and (c3):
(c2) a triarylsulfonium borate salt represented by the following formula:
where each R 5 is the same or different alkyl group, aryl group, alkoxy group, or heteroatom-containing organic group, and X − is SbF 6- , AsF 6- , PF 6- , BF 4- , B(C 6 F 5 ) 4- , HSO 4- , ClO 4- , CF 3 SO 3- , nonafluorobutanesulfonate, tris (pentafluoroethyl) trifluorophosphate, tris (hepta fluoropropyl) trifluorophosphate, tris (nonafluoroisobutyl) trifluoro phosphate, or bis (nonafluorobutyl isobutyl) tetrafluoro phosphate;
(c3) a triarylsulfonium tetrakis(pentafluorophenyl) borate salt represented by the following formula
2 . The curable silicone composition according to claim 1 , wherein the monovalent epoxy-substituted organic groups in component (A) are groups selected from glycidoxyalkyl groups, 3,4-epoxycyclohexylalkyl groups, and epoxyalkyl groups.
3 . The curable silicone composition according to claim 1 , wherein the monovalent epoxy-substituted organic groups in component (B) are groups selected from glycidoxyalkyl groups, 3,4-epoxycyclohexylalkyl groups, and epoxyalkyl groups.
4 . The curable silicone composition according to claim 1 , wherein component (C-2) comprises component (c2).
5 . The curable silicone composition according to claim 1 , wherein component (C-2) comprises component (c3).
6 . The curable silicone composition according to claim 1 , wherein a mass ratio of component (C-1): component (C-2) is in a range of from 1:10 to 10:1.
7 . The curable silicone composition according to claim 1 , further comprising:
(D) an adhesion promoter, in an amount of from about 0.01 to about 5 mass % of the total mass of components (A), (B), (C) and (D).
8 . A cured product obtained by curing the curable silicone composition according to claim 1 .