Curable silicone compositions having enhanced cure-through-volume

• US 6,827,985 B2
• Filed: 11/04/2002
• Issued: 12/07/2004
• Est. Priority Date: 05/02/2001
• Status: Active Grant

• Current Assignee: Henkel IP & Holding GmbH (Henkel AG & Co KGaA)
• Original Assignee: Henkel Corporation (Henkel AG & Co KGaA)
• Inventors: Levandoski, Michael P., DeCato, Alfred A.
• Primary Examiner(s): Robertson, Jeffrey B.
• Application Number:
  US10/275,374
• Publication Number:
  US 20030212229A1
• Time in Patent Office: 764 Days
• Field of Search: 427/387, 427/515, 522/65, 522/99, 522/148, 528/12, 528/22, 528/32, 528/38, 528/41, 525/477
• US Class Current: 427/515
• CPC Class Codes: C08G 77/14 containing silicon bound to oxygen-containing groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/18 to alkoxy or aryloxy groups
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/26 nitrogen-containing groups
• CPC Class Codes: C08G 77/70 Siloxanes defined by use of the MDTQ nomenclature
• CPC Class Codes: C08L 101/10 containing hydrolysable silane groups
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/06 containing silicon bound to oxygen-containing groups C08L83/12 takes precedence

Abstract

A photocurable silicone composition which includes an additive which provides cure-through-volume of the overall composition. The additive is desirably a curable amino silyl-terminated polyorganosiloxane.

Claims

1. A photocurable silicone composition comprising:

a. a photocurable silicone polymer;

b. a photoinitiator; and

c. a curable amino silyl-terminated polymer additive comprising the reaction product of at least one silanol-terminated polyorganosiloxane and at one or more end-capping silane components.

2. The composition of claim 1 wherein said polymer additive is present in amounts sufficient to increase CTV as compared to the same composition without said additive.

3. The composition of claim 1 wherein said polymer additive comprises a predominant amount of a polymer corresponding to the structure:

wherein A represents a polymer or copolymer backbone selected from the group consisting of polyurethane, silicone, polyamide, polyether, polyester and combinations thereof and n is an integer 1 to 1,200;

R³ and R⁵ are different functional groups having up to 10 carbon atoms and are selected from (meth)acryl, amino, vinyl, alkoxy, aryloxy, acetoxy, oxime and combinations thereof, and either R³ or R⁵ may also be a monovalent heterohydrocarbon radical having up to 10 carbon atoms (C_1-10), wherein the hetero atoms are selected from O, N and S;

R⁴ is alkyl) (C_1-10) or —

CH₂CH₂OCH₃.

4. The composition of claim 1 wherein said curable amino silyl-terminated polymer additive comprises vinydimethyoxy/aminopropyldimethoxy terminated polydimethylsiloyane.

5. The composition of claim 1 wherein said polymer additive is present in amounts of about 0.2-15% by weight of the total silicone composition.

6. The composition of claim 1, wherein said photocurable silicone polymer corresponds to the structure:

wherein R₁ is H or alkyl C_1-10;

R² is a divalent hydrocarbon or hydrocarbonoxy group;

R³ and R⁴ may be the same or different and are C_1-10 monovalent hydrocarbon radicals;

R⁵ is C_1-10 monovalent hydrocarbon radical and n is an integer from 1 to 1200.

7. The composition of claim 6, wherein said photocurable silicone polymer corresponds to the structure:

wherein R¹ is H or alkyl C_1-10;

R² is a divalent hydrocarbon or hydrocarbonoxy group;

R³ and R⁴ may be the same or different and are selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, alkoxy, aryloxy, (meth)acryl, oxime, acetoxy, N, N-dialkylamino, N,N-dialkylamines, N-alkylamido,

wherein R is H or hydrocarbyl and combinations thereof;

R⁵ is C_1-10 monovalent hydrocarbon radical and n is an integer from 1 to 1200.

8. The composition of claim 1, wherein the photocurable silicone composition is also moisture curable.

9. The composition of claim 1, wherein the photoinitiator is selected from the group consisting of benzoin, benzophenones, acetophenones and combinations thereof.

10. The composition of claim 8 further including a moisture curing catalyst.

11. A method of preparing a photocurable silicone composition having enhanced cure-through-volume comprising the steps of:

(i) providing a photocurable silicone polymer and a photoiniatiator; and

(ii) incorporating therein a curable amino silyl-terminated polymer additive comprising the reaction product of at least one silanol-terminated polyorganosiloxane and one or more silane components.

12. A method of providing enhanced cure-through-volume in a photocurable silicone composition comprising the steps of:

(i) providing a photocurable silicone composition comprising;

a. A photocurable silicone polymer;

b. a photoinitiator; and

c. a curable amino silyl-terminated polymer additive comprising the reaction product of at least one silanol-terminated polyorganosiloxane and one or more end-capping silane components;

(ii) applying said photocurable silicone compositions to a substrate; and

exposing said silicone composition to sufficient radiation to photocure said silicone composition.

13. A photocurable silicone composition comprising:

a. a photocurable silicone polymer;

b. a photoinitiator; and

c. a curable amino silyl-terminated polymer additive comprising the reaction product of at least one silanol-terminated polyorganosiloxane and one or more end-capping silane components, provided that at least one of the end-capping silane components is an amino containing component.

14. A method of preparing a photocurable silicone composition having enhanced cure-through-volume comprising the steps of:

(i) providing a photocurable silicone polymer and a photoiniatiator; and

(ii) incorporating therein a curable amino silyl-terminated polymer additive comprising the reaction product of at least one silanol-terminated polyorganosiloxane and one or more end-capping silane components, provided that at least one of the end-caping silane components is an amino containing component.

15. A method of providing enhanced cure-through-volume in a photocurable silicone composition comprising the steps of:

(i) providing a photocurable silicone composition comprising;

a. a photocurable silicone polymer;

b. a photoinitiator; and

c. a curable amino silyl-terminated polymer additive comprising the reaction product of at least one silanol-terminated polyorganosiloxane and one or more end-capping silane components, provided that at least one of the end-caping silane components is an amino containing component;

(ii) applying said photocurable silicone compositions to a substrate; and

(iii) exposing said silicone composition to sufficient radiation to photocure said silicone composition.