Cross-linked silicone polymer and process for producing the same

Patent metadata

Field	Value
Publication number	US-9388284-B2
Application number	US-201414244211-A
Country	US
Kind code	B2
Filing date	Apr 3, 2014
Priority date	Apr 12, 2013
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

A siloxane compound comprises a plurality of siloxane repeating units and at least a portion of the siloxane repeating units are cyclosiloxane repeating units conforming to a specified structure. A process for producing such siloxane compounds is also provided. A process and kit for producing a cross-linked silicone polymer using the described siloxane compounds is also provided. A light emitting diode (LED) comprises an encapsulant, and the encapsulant comprises a cross-linked silicone polymer produced from the described siloxane compounds.

First claim

What is claimed is:

1. A process for producing a cross-linked silicone polymer, the process comprising the steps of:
(a) providing a first siloxane compound, the first siloxane compound comprising a plurality of siloxane repeating units, wherein at least a portion of the siloxane repeating units are cyclosiloxane repeating units, and the cyclosiloxane repeating units are independently selected from the group consisting of cyclosiloxane repeating units conforming to the structure of Formula (XL)

wherein R 1 and R 2 are independently selected from the group consisting of alkyl groups, substituted alkyl groups, cycloalkyl groups, substituted cycloalkyl groups, alkenyl groups, substituted alkenyl groups, cycloalkenyl groups, substituted cycloalkenyl groups, heterocyclyl groups, substituted heterocyclyl groups, aryl groups, substituted aryl groups, heteroaryl groups, substituted heteroaryl groups, trialkylsiloxy groups, aryldialkylsiloxy groups, alkyldiarylsiloxy groups, and triarylsiloxy groups; R 20 and R 21 are independently selected from the group consisting of hydrogen, alkyl groups, substituted alkyl groups, alkanediyl groups, substituted alkanediyl groups, cycloalkyl groups, substituted cycloalkyl groups, alkenyl groups, substituted alkenyl groups, alkenediyl groups, substituted alkenediyl groups, cycloalkenyl groups, substituted cycloalkenyl groups, heterocyclyl groups, substituted heterocyclyl groups, aryl groups, substituted aryl groups, heteroaryl groups, substituted heteroaryl groups, trialkylsiloxy groups, aryldialkylsiloxy groups, alkyldiarylsiloxy groups, and triarylsiloxy groups; provided only one of R 20 and R 21 can be hydrogen; and further provided, if one of R 20 and R 21 is selected from the group consisting of alkanediyl groups, substituted alkanediyl groups, alkenediyl groups, and substituted alkenediyl groups, then the other of R 20 and R 21 is also selected from the group consisting of alkanediyl groups, substituted alkanediyl groups, alkenediyl groups, and substituted alkenediyl groups, and R 20 and R 21 are bonded to form a cyclic moiety; R 3 and R 4 are independently selected from the group consisting of alkyl groups, substituted alkyl groups, alkanediyl groups, substituted alkanediyl groups, cycloalkyl groups, substituted cycloalkyl groups, alkenyl groups, substituted alkenyl groups, alkenediyl groups, substituted alkenediyl groups, cycloalkenyl groups, substituted cycloalkenyl groups, heterocyclyl groups, substituted heterocyclyl groups, aryl groups, substituted aryl groups, heteroaryl groups, substituted heteroaryl groups, trialkylsiloxy groups, aryldialkylsiloxy groups, alkyldiarylsiloxy groups, and triarylsiloxy groups; provided, if one of R 3 and R 4 is selected from the group consisting of alkanediyl groups, substituted alkanediyl groups, alkenediyl groups, and substituted alkenediyl groups, then the other of R 3 and R 4 is also selected from the group consisting of alkanediyl groups, substituted alkanediyl groups, alkenediyl groups, and substituted alkenediyl groups, and R 3 and R 4 are bonded to form a cyclic moiety; x is zero or any positive integer; and y is a positive integer from 1 to 6;
(b) providing a siloxane compound conforming to the structure of Formula (LXX)

wherein R 70 and R 71 are independently selected from the group consisting of haloalkyl groups, aralkyl groups, aryl groups, substituted aryl groups, heteroaryl groups, and substituted heteroaryl groups; c is 0 or a positive integer from 1 to 3; R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , R 78 , R 80 , R 81 , R 82 , R 83 , R 84 , R 85 , and R 86 are independently selected from the group consisting of alkyl groups, substituted alkyl groups, cycloalkyl groups, substituted cycloalkyl groups, alkenyl groups, substituted alkenyl groups, cycloalkenyl groups, substituted cycloalkenyl groups, heterocyclyl groups, substituted heterocyclyl groups, aryl groups, substituted aryl groups, heteroaryl groups, substituted heteroaryl groups, trialkylsiloxy groups, aryldialkylsiloxy groups, alkyldiarylsiloxy groups, and triarylsiloxy groups; provided, if c is 0, then R 74 and R 82 are independently selected from the group consisting of haloalkyl groups, aralkyl groups, aryl groups, substituted aryl groups, heteroaryl groups, and substituted heteroaryl groups;
(c) providing a ring-opening catalyst;
(d) combining the first siloxane compound, the siloxane compound conforming to the structure of Formula (LXX), and the ring-opening catalyst to produce a reaction mixture;
(e) reacting the components in the reaction mixture under conditions such that (i) the ring-opening catalyst opens at least a portion of the cyclosiloxane repeating units in the first siloxane compound and the rings in the siloxane compound conforming to the structure of Formula (LXX) to form cross-linking groups and (ii) at least a portion of the cross-linking groups react with other molecules of the first siloxane compound to produce cross-links between molecules thereby forming a cross-linked silicone polymer.

2. The process of claim 1 , wherein the process further comprises the step of heating the cross-linked silicone polymer to accelerate the cross-linking.

3. The process of claim 1 , wherein the first siloxane compound further comprises at least one segment conforming to the structure of Formula (X)

wherein R 10 and R 11 are independently selected from the group consisting of hydrogen, alkyl groups, substituted alkyl groups, cycloalkyl groups, substituted cycloalkyl groups, alkenyl groups, substituted alkenyl groups, cycloalkenyl groups, substituted cycloalkenyl groups, heterocyclyl groups, substituted heterocyclyl groups, aryl groups, substituted aryl groups, heteroaryl groups, substituted heteroaryl groups, trialkylsiloxy groups, aryldialkylsiloxy groups, alkyldiarylsiloxy groups, and triarylsiloxy groups; provided only one of R 10 and R 11 can be hydrogen.

4. The process of claim 1 , wherein x is 0 and y is 1.

5. The process of claim 1 , wherein R 3 and R 4 are independently selected from the group consisting of alkyl groups, haloalkyl groups, and aryl groups.

6. The process of claim 5 , wherein R 3 and R 4 are independently selected from the group consisting of aryl groups.

7. The process of claim 6 , wherein R 3 and R 4 are each phenyl groups.

8. The process of claim 1 , wherein R 1 and R 2 are independently selected from the group consisting of alkyl groups and aryl groups.

9. The process of claim 8 , wherein R 1 and R 2 are independently selected from the group consisting of alkyl groups.

10. The process of claim 9 , wherein R 1 and R 2 are methyl groups.

11. The process of claim 1 , wherein the siloxane compound further comprises silyl terminating groups.

12. The process of claim 1 , wherein about 10 mol. % or more of the repeating units in the first siloxane compound conform to the structure of Formula (XL).

13. The process of claim 1 , wherein the reaction mixture further comprises a compound conforming to a structure selected from the group consisting of Formula (LX) and Formula (LXV)

wherein R 60 , R 61 , R 62 , and R 63 are independently selected from the group consisting of alkyl groups, substituted alkyl groups, cycloalkyl groups, subs

Assignees

• Milliken & Co

Inventors

• Liu Yuzhou
• Wang Yunzhang
• Stapleton Russell A

Classifications

• H10W90/756

  between a chip and a stacked lead frame, conducting package substrate or heat sink · CPC title

• H10H20/854

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

• C09D183/04

  Polysiloxanes · CPC title

• C08L83/04

  Polysiloxanes · CPC title

• C08K5/50

  Phosphorus bound to carbon only · CPC title