IP Library › Granted Patent US 10,259,912
Granted Patent B2
US 10,259,912 · App. 15/241,351 · Granted Apr 16, 2019

Organopolysiloxane composition

Inventors: Kyoung Jin Bok (Gyeonggi-do, KR); Seung Kwang Seo (Seoul, KR); Jung Mo An (Incheon, KR); Seung Han Kim (Gyeonggi-do, KR)
Assignee: KCC CORPORATION
C08G77/80C08K5/56C08L83/00C08L83/04C08G77/12C08G77/14C08G77/20C08L2201/14C08L2203/20C08L2205/025C08L2205/05H01L51/5253
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Quick Facts
Patent No.
US 10,259,912
App. No.
15/241,351
Granted
Apr 16, 2019
Kind
B2
Abstract

A curable organopolysiloxane composition which is capable of maintaining the refractive index and gas barrier at a certain level by incorporating diphenyl group into a silicone resin and maintaining the phenyl content at a certain level.

Claims (88)

1. A curable organopolysiloxane composition comprising a compound of Chemical Formula 1 and a compound of Chemical Formula 2,

which has, on a 2-mm thick specimen in a cured state, an oxygen permeability of 250 cc/m 2 *day or lower measured according to ASTM D3985, and a refractive index of 1.55 or higher measured according to ASTM D1747:

(R 1 R 2 R 3 SiO 1/2 ) a .(R 4 R 5 SiO 2/2 ) b .(R 6 SiO 3/2 ) c .(SiO 4/2 ) d   [Chemical Formula 1]

wherein

each of R 1 , R 2 , and R 3 is independently an alkenyl group with a carbon number of 2 to 10, or a monovalent hydrocarbon group with a carbon number of 1 to 12 other than the alkenyl group, provided that one or more of R 1 , R 2 , and R 3 are alkenyl groups with a carbon number of 2 to 10,

each of R 4 ,R 5 , and R 6 is independently a monovalent hydrocarbon group with a carbon number of 1 to 12 other than the alkenyl group, and

a, b, c and d, respectively, satisfy 0<a<1, 0<b<1, 0<c<1, 0≤d<1, and a+b+c+d=1,

(R 7 R 8 R 9 SiO 1/2 ) e .(R 10 SiO 3/2 ) f   [Chemical Formula 2]

wherein

each of R 7 , R 8 , and R 9 is independently an alkenyl group with a carbon number of 2 to 10, or a monovalent hydrocarbon group with a carbon number of 1 to 12 other than the alkenyl group, provided that one or more of R 7 , R 8 , and R 9 are alkenyl groups with a carbon number of 2 to 10,

R 10 is independently a monovalent hydrocarbon group with a carbon number of 1 to 12 other than the alkenyl group, and

e and f, respectively, satisfy 0<e<1, 0<f<1 and e+f=1.

2. The curable organopolysiloxane composition according to claim 1 , wherein

each of R 4 , R 5 , and R 6 is independently an alkenyl group with a carbon number of 2 to 8, an alkyl group with a carbon number of 1 to 12, or an aryl group with a carbon number of 6 to 12, provided that one or more of R 4 , R 5 , and R 6 are alkenyl groups with a carbon number 2 to 8,

each of R 4 , R 5 , and R 6 is independently an alkyl group with a carbon number of 1 to 12, or an aryl group with a carbon number of 6 to 12, and

a, b, c and d, respectively, satisfy the formula 0<a<0.7, 0.1≤b<0.6, 0<c<0.9, 0≤d<0.5, and a+b+c+d=1,

each of R 7 , R 8 , and R 9 is independently an alkenyl group with a carbon number of 2 to 8, an alkyl group with a carbon number of 1 to 12, or an aryl group with a carbon number of 6 to 12, provided that and one or more of R 7 , R 8 , and R 9 are alkenyl groups with a carbon number 2 to 8,

R 10 is independently an alkyl group with a carbon number of 1 to 12, or an aryl group with a carbon number of 6 to 12, and

a and c, respectively, satisfy the formula 0<a<0.7, 0<c<0.9, and a+c=1.

3. The curable organopolysiloxane composition according to claim 1 , wherein

each of R 1 , R 2 , and R 3 is independently an alkenyl group with a carbon number of 2 to 4, an alkyl group with a carbon number of 1 to 4, or an aryl group with a carbon number of 6 to 12, provided that one or more of R 1 , R 2 , and R 3 are alkenyl groups with a carbon number 2 to 4, and

each of R 4 , R 5 , and R 6 is independently an aryl group with a carbon number of 6 to 12,

each of R 7 , R 8 , and R 9 is independently an alkenyl group with a carbon number of 2 to 4, an alkyl group with a carbon number of 1 to 4, or an aryl group with a carbon number of 6 to 12, provided that one or more of R 7 , R 8 , and R 9 are alkenyl groups with a carbon number 2 to 4, and

R 10 is independently an aryl group with a carbon number of 6 to 12.

4. The curable organopolysiloxane composition according to claim 1 , wherein

each of R 1 , R 2 , and R 3 is independently vinyl, allyl, butenyl, hexenyl, methyl, ethyl, propyl, cyclohexyl, phenyl, tolyl or naphthyl, provided that one or more of R 1 to R 3 are vinyl, allyl, butenyl or hexenyl,

each of R 4 , R 5 , and R 6 is independently methyl, ethyl, propyl, cyclohexyl, phenyl, tolyl or naphthyl, and

a, b, c and d, respectively, satisfy 0.05≤a≤0.7, 0.1≤b≤0.4, 0.3≤c≤0.7, 0≤d<0.3 and a+b+c+d=1,

each of R 7 , R 8 , and R 9 is independently vinyl, allyl, butenyl, hexenyl, methyl, ethyl, propyl, cyclohexyl, phenyl, tolyl or naphthyl, provided that one or more of R 7 to R 9 are vinyl, allyl, butenyl or hexenyl,

R 10 is independently methyl, ethyl, propyl, cyclohexyl, phenyl, tolyl or naphthyl, and

a and c, respectively, satisfy 0.05≤a≤0.7, 0.3≤c≤0.7, and a+c=1.

5. The curable organopolysiloxane composition according to claim 1 , wherein

the compound of Chemical Formula 1 is selected from the group consisting of:

(ViMe 2 SiO 1/2 ) a .(MePhSiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 2 MeSiO 1/2 ) a .(MePhSiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 3 SiO 1/2 ) a .(MePhSiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViMe 2 SiO 1/2 ) a .(MePhSiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 2 MeSiO 1/2 ) a .(MePhSiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 3 SiO 1/2 ) a .(MePhSiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViMe 2 SiO 1/2 ) a .(Ph 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 2 MeSiO 1/2 ) a .(Ph 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 3 SiO 1/2 ) a .(Ph 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViMe 2 SiO 1/2 ) a .(Ph 2 SiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 2 MeSiO 1/2 ) a .(Ph 2 SiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 3 SiO 1/2 ) a .(PhSiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViMe 2 SiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 2 MeSiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 3 SiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViMe 2 SiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 2 MeSiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) c .

(Vi 3 SiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViMePhSiO 1/2 ) a .(MePhSiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d .

(Vi 2 PhSiO 1/2 ) a .(MePhSiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViMePhSiO 1/2 ) a .(Ph 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4,2 ) d ,

(Vi 2 PhSiO 1/2 ) a .(Ph 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViMePhSiO 1/2 ) a .(Ph 2 SiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 2 PhSiO 1/2 ) a .(Ph 2 SiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViMePhSiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 2 PhSiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViMePhSiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 2 PhSiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViPh 2 SiO 1/2 ) a .(MePhSiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(Vi 2 PhSiO 1/2 ) a .(MePhSiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViPh 2 SiO 1/2 ) a .(MePhSiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViPh 2 SiO 1/2 ) a .(Ph 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViPh 2 SiO 1/2 ) a .(Ph 2 SiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d ,

(ViPh 2 SiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(PhSiO 3/2 ) c .(SiO 4/2 ) d , and

(ViPh 2 SiO 1/2 ) a .(Me 2 SiO 2/2 ) b .(MeSiO 3/2 ) c .(SiO 4/2 ) d .

6. The curable organopolysiloxane composition according to claim 1 , wherein

the compound of Chemical Formula 1 is included in the composition in an amount of 50 to 90% by weight, based on the total weight of the composition.

7. The curable organopolysiloxane composition according to claim 6 , wherein

the compound of Chemical Formula 1 is included in the composition in an amount of 60 to 80% by weight, based on the total weight of the composition.

8. The curable organopolysiloxane composition according to claim 1 , wherein

the compound of Chemical Formula 2 is selected from the group consisting of: (Me 2 ViSiO 1/2 ) e .(PhSiO 3/2 ) f , (MePhViSiO 1/2 ) e .(PhSiO 3/2 ) f , (Ph 2 ViSiO 1/2 ) e .(PhSiO 3/2 ) f , (MeVi 2 SiO 1/2 ) e .(PhSiO 3/2 ) f , (PhVi 2 SiO 1/2 ) e .(PhSiO 3/2 ) f , (Vi 3 SiO 1/2 ) e .(PhSiO 3/2 ) f , (Me 2 ViSiO 1/2 ) e .(MeSiO 3/2 ) f , (MePhViSiO 1/2 ) e .(MeSiO 3/2 ) f , (Ph 2 ViSiO 1/2 ) e .(MeSiO 3/2 ) f , (MeVi 2 SiO 1/2 ) e .(MeSiO 3/2 ) f , (PhVi 2 SiO 1/2 ) e .(MeSiO 3/2 ) f , and (Vi 3 SiO 1/2 ) e .(MeSiO 3/2 ) f .

9. The curable organopolysiloxane composition according to claim 1 , wherein

the compound of Chemical Formula 2 is included in the composition in an amount of 1 to 15% by weight, based on the total weight of the composition.

10. The curable organopolysiloxane composition according to claim 9 , wherein

the compound of Chemical Formula 2 is included in the composition in an amount of 3 to 8% by weight, based on the total weight of the composition.

11. The curable organopolysiloxane composition according to claim 1 ,

further comprising 5 to 45% by weight of a hydrogen crosslinking agent, based on the total weight of the composition.

12. The curable organopolysiloxane composition according to claim 1 ,

further comprising 1 to 10% by weight of an adhesion promoter, based on the total weight of the composition.

13. The curable organopolysiloxane composition according to claim 1 ,

further comprising a catalyst selected from the group consisting of a platinum-based catalyst, a rhodium-based catalyst and a palladium-based catalyst.

14. The curable organopolysiloxane composition according to claim 1 ,

further comprising 0.08% by weight or less of a reaction-retarding agent.

15. A molding material for a light emitting diode element comprising a cured product of the composition according to claim 1 .

16. A light emitting diode device comprising a light emitting diode element, wherein the light emitting diode element is molded with the molding material comprising a cured product of the composition according to claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 30, 2016
From: BOK, KYOUNG JIN; SEO, SEUNG KWANG; AN, JUNG MO; KIM, SEUNG HAN
To: KCC CORPORATION
Reel/Frame 039905/0521 →
Priority Claims (1)
KR 10-2015-0117818 · Aug 21, 2015 · national
Continuity (1)
Related Publication 20170051115A1 · Feb 23, 2017