Organopolysiloxane prepolymer and a curable organopolysiloxane composition comprising the same

Patent metadata

Field	Value
Publication number	US-9994681-B2
Application number	US-201715647648-A
Country	US
Kind code	B2
Filing date	Jul 12, 2017
Priority date	Jan 13, 2015
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

The present invention discloses an organopolysiloxane prepolymer and a curable organopolysiloxane composition comprising the same, particularly used as an encapsulant in light emitting diodes.

First claim

What is claimed is:

1. A curable organopolysiloxane composition, comprising:
(a) an organopolysiloxane prepolymer being a reaction product of reactants comprising:
(1) a cyclic isocyanurate having two or more ethylenically unsaturated double bonds which is represented by formula (1)

wherein
R 1 , R 2 and R 3 independently from each other represent an alkyl group having from 1 to 20 carbon atoms, an aromatic group having from 6 to 20 carbon atoms, a monovalent organic group represented by —(CH 2 ) m —X or —(CH 2 ) p —O—(CH 2 ) q —Y, in which
m is from 0 to 3, p is from 0 to 3, q is from 0 to 3, X and Y are selected from the group consisting of an alkenyl group having from 2 to 20 carbon atoms, an epoxy group having from 2 to 20 carbon atoms, and a trialkoxysilyl group having from 1 to 20 carbon atoms independently for each alkoxy group; and
at least two of R 1 , R 2 and R 3 contain an ethylenically unsaturated double bond,

(2) a linear organohydroqensiloxane having at least one hydrogen atom directly bonded to a silicon atom in one molecule, represented by the average compositional formula (2):
R 4 R 5 R 6 SiO 1/2 ) a (R 7 R 8 SiO 2/2 ) b   (2),

wherein
at least one of R 4 to R 8 is a hydrogen atom directly bonded to a silicon atom, at least one of R 4 to R 8 is an aromatic group having from 6 to 20 carbon atoms, the others of R 4 to R 8 independently from each other represent an alkyl group having from 1 to 20 carbon atoms or an alkoxy group having from 1 to 20 carbon atoms, a is from 0.1 to 0.9, b is from 0.1 to 0.9, and the sum of a+b is 1; and
(3) an hydrosilylation catalyst (I),

wherein the molar ratio of the ethylenically unsaturated double bonds contained in component (a) to the hydrogen atom directly bonded to a silicon atom contained in component (b) is from 2.2 to 5.0,
(b) an organopolysiloxane comprising at least two ethylenically unsaturated double bonds in one molecule represented by the average compositional formula (3):
(R 9 R 10 R 11 SiO 1/2 ) c (R 12 SiO 3/2 ) d (SiO 4/2 ) e   (3)

wherein
at least one of R 9 to R 12 is an alkenyl group having from 2 to 20 carbon atoms, at least one of R 9 to R 12 is an aromatic group having from 6 to 20 carbon atoms, the others of R 9 to R 12 independently from each other represent an alkyl group having from 1 to 20 carbon atoms or an alkoxy group having from 1 to 20 carbon atoms, from 15 to 65 mol % of R 9 to R 12 in one molecule of the organopolysiloxane are an aromatic group having from 6 to 20 carbon atoms, from 1 to 50 mol % of R 9 to R 12 in one molecule of the organopolysiloxane are an alkenyl group having from 2 to 20 carbon atoms, and the total mol % of R 9 to R 12 in one molecule of the organopolysiloxane is 100 mol %,
c is from 0.1 to 0.8, d is from 0.2 to 0.9, e is from 0 to 0.2, and the sum of c+d+e is 1,
(c) a branched polyorganohydrogensiloxane having 1 to 3 hydrogen atoms directly bonded to a silicon atom in one molecule represented by the average compositional formula (4):
(R 13 R 14 R 15 SiO 1/2 ) f (R 16 SiO 3/2 ) g (SiO 4/2 ) h   (4)

wherein
at least one of R 13 to R 16 is a hydrogen atom directly bonded to a silicon atom, at least one of R 13 to R 16 is an aromatic group having from 6 to 20 carbon atoms, the others of R 13 to R 16 independently from each other represent an alkyl group having from 1 to 20 carbon atoms or an alkoxy group having from 1 to 20 carbon atoms, f is from 0.1 to 0.8, g is from 0.2 to 0.9, h is from 0 to 0.5, and the sum of f+g+h is 1;
(d) a linear organohydrogensiloxane having at least one hydrogen atom directly bonded to a silicon atom in one molecule, represented by the average compositional formula (5):
(R 17 R 18 R 19 SiO 1/2 ) i (R 20 R 21 SiO 2/2 ) i   (5),

wherein
at least one of R 17 to R 21 is a hydrogen atom directly bonded to a silicon atom, at least one of R 17 to R 21 is an aromatic group having from 6 to 20 carbon atoms, the others of R 17 to R 21 independently from each other represent an alkyl group having from 1 to 20 carbon atoms or an alkoxy group having from 1 to 20 carbon atoms, i is from 0.1 to 0.9, j is from 0.1 to 0.9, and the sum of i+j is 1, and
(e) a hydrosilylation catalyst (II).

2. The curable organopolysiloxane composition according to claim 1 , wherein component (a) is present in an amount of from 5 to 25% by weight of the total weight of all components.

3. The curable organopolysiloxane composition according to claim 1 , wherein from 20 to 50 mol % of R 9 to R 12 in one molecule of component (b) is an aromatic group having from 6 to 20 carbon atoms.

4. The curable organopolysiloxane composition according to claim 1 , wherein from 5 to 30 mol % of R 9 to R 12 in one molecule of component (b) is alkenyl group having from 2 to 20 carbon atoms.

5. The curable organopolysiloxane composition according to claim 1 , wherein component (b) is present in an amount of from 5 to 80% by weight of the total weight of all components.

6. The curable organopolysiloxane composition according to claim 1 , wherein the component (c) is present in an amount of from 1 to 50% by weight of the total weight of all components.

7. The curable organopolysiloxane composition according to claim 1 , wherein in component (d), i is a positive number of from 0.2 to 0.6, j is a positive number of from 0.4 to 0.8, and the sum of i+j is 1.

8. The curable organopolysiloxane composition according to claim 1 , wherein the molar ratio of the hydrogen atom directly bonded to a silicon atom contained in component (d) to the alkenyl group contained in component (b) is from 0.5 to 1.2.

9. The curable organopolysiloxane composition according to claim 1 , wherein the amount of component (d) is from 1 to 40% by weight of the total amount of all components.

10. An optical device comprising the curable organopolysiloxane composition according to claim 1 .

11. A cured product of the curable organopolysiloxane composition according to claim 1 .

12. A light emitting material comprising the cured product according to claim 11 .

13. An optical device comprising the cured product according to claim 11 .

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Wu Hao
• Tan Wenjuan
• Xing Wentao
• Zhang Yong
• Sano Mieko
• Hikita Aya
• Takano Tadashi
• Zhang Liwei
• Yang Carol
• Li Zhiming
• Du Juan

Classifications

• C08K5/3477

  Six-membered rings · CPC title

• C08G77/12

  containing silicon bound to hydrogen · CPC title

• C08G77/20 Primary

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C08G77/08

  characterised by the catalysts used · CPC title

• H10H20/854

  characterised by their material, e.g. epoxy or silicone resins · CPC title