Ultraviolet light curable acrylic functional silicone compositions

• US 4,348,454 A
• Filed: 03/02/1981
• Issued: 09/07/1982
• Est. Priority Date: 03/02/1981
• Status: Expired due to Term

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Eckberg, Richard P.
• Primary Examiner(s): BRIGGS SR, WILBERT
• Application Number:
  US06/239,297
• Time in Patent Office: 554 Days
• Field of Search: 528/26, 528/25, 525/479, 204/159.13, 556/451, 428/40, 428/334, 428/452, 427/54.1
• US Class Current: 428/334
• CPC Class Codes: C08G 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence
• CPC Class Codes: C08G 77/385 containing halogens
• CPC Class Codes: C09D 183/06 containing silicon bound to oxygen-containing groups C09D183/12 takes precedence
• CPC Class Codes: D21H 19/32 obtained by reactions forming a linkage containing silicon in the main chain of the macromolecule
• CPC Class Codes: Y10T 428/1452 Polymer derived only from ethylenically unsaturated monomer
• CPC Class Codes: Y10T 428/1462 Polymer derived from material having at least one acrylic or alkacrylic group or the nitrile or amide derivative thereof [e.g., acrylamide, acrylate ester, etc.]
• CPC Class Codes: Y10T 428/263 Coating layer not in excess of 5 mils thick or equivalent
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

Acrylic functional siloxane polymer compositions which are especially useful for ultraviolet curable silicone release coating applications are provided as a reaction product of omega-chloro-1-alkenes, dialkylhydrogen chainstopped polydialkylalkylhydrogen siloxane copolymers, catalytic amounts of precious metal complexes and acrylic functional monomers.

Claims

1. An acrylic functional polyorganosiloxane composition comprising:

the reaction product of (A) an omega-haloalkene;

(B) a dialkylhydrogen chainstopped polydialkylalkylhydrogensiloxane copolymer;

(C) an amount of precious metal catalyst effective for catalyzing a hydrosilation reaction between said alkene and said siloxane copolymer; and

(D) an acrylic functional monomer.

2. A composition as in claim 1 wherein said omega-haloalkene is selected from the group consisting of gamma-chloropropene, 4-chloro-1-butene, 10-chloro-1-decene, and 3-chloro-2-methylpropene.

3. A composition as in claim 1 wherein said dimethylhydrogen chainstopped polydialkyl-alkylhydrogen siloxane copolymer has the general formula:

##STR5## wherein each R represents, independently, a monovalent hydrocarbon radical;

R'"'"' represents, independently, a hydrogen atom or a monovalent hydrocarbon radical;

y plus z is an integer of, approximately, 25 to 600 such that said copolymer has a viscosity of, approximately 20 to 5000 centipoise at 25°

C. and a hydrogen content of 0.5 to 50 weight % based on methylhydrogen siloxy unit functionality.

4. A composition as in claim 1 wherein said precious metal catalyst is a complex of chloroplatinic acid and a compound selected from the group consisting of octyl alcohol and divinyltetramethyldisiloxane.

5. A composition as in claim 1 wherein said acrylic functional monomer is selected from the group consisting of acrylic acid, methacrylic acid, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, and pentaerythritoltriacrylate.

6. A composition as in claim 1 further comprising an amount of free radical photoinitiator effective for curing a 0.1 to 5.0 mil coating of said composition to a non-adherent film upon exposure to an amount of ultraviolet or electron beam radiation effective for curing said coating composition.

7. An article of manufacture comprised of a substrate and a film of 0.1 to 5.0 mils of the composition of claims 1 or 6 coated thereon.

8. An article as in claim 7 wherein said substrate is paper.

16. A process for providing an article of manufacture comprised of a substrate and a film of 0.5 to 5.0 mils of the composition of claim 1 coated thereon.

17. A process for providing an article as in claim 16 wherein said substrate is paper.

9. A process for providing acrylic functional polyorganosiloxane compositions comprising the steps of reacting (A) 1 to 50 parts by weight of an omega-chloro-1-alkene;

(B) 50 to 99 parts by weight of a dialkylhydrogen chainstopped polydialkyl-alkylhydrogen siloxane copolymer and;

(C) an amount of precious metal catalyst effective for catalysing a hydrosilation reaction between said alkene and said siloxane copolymer; and

thereafter further reacting (D) 0.2 to 30 parts by weight of an acrylic functional moiety effective for providing a siloxane copolymer having 0.5 to 50 weight percent acrylic siloxy units.

10. A process as in claim 9 wherein said omega-chloro-1-alkene is selected from the group consisting of gamma-chloropropene, 4-chloro-1-butene, 10-chloro-1-decene, and 3-chloro-2-methylpropene.

11. A process as in claim 9 wherein said dimethylhydrogen chainstopped polydialkyl-alkylhydrogen siloxane copolymer has the general formula:

##STR6## wherein each R represents, independently, a monovalent hydrogen atom or a monovalent hydrocarbon radical;

y plus z is an integer of, approximately, 25 to 600 such that said copolymer has a viscosity of, approximately, 20 to 5000 centipoise at 25°

C. and a hydrogen content of 0.5 to 50 weight % based on methylhydrogensiloxy unit functionality.

12. A process as in claim 9 wherein said precious metal catalyst is a complex of chloroplatinic acid and a compound selected from the group consisting of octyl alcohol and divinyltetramethyldisiloxane.

13. A process as in claim 9 wherein said acrylic functional monomer is selected from the group consisting of acrylic acid, methacrylic acid, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, and pentaerythritoltriacrylate.

14. A process as in claim 9 further comprising the steps of adding an amount of free radical photoinitiator effective for curing a 0.5 to 5.0 mil coating of said composition to a non-adherent film applying a coating of said composition to a substrate, and exposing said coating to an amount of ultraviolet or electron beam radiation effective for curing said coating.

15. A process for as in claim 14 wherein said free radical photoinitiator is selected from the group consisting of alkylbenzoin ethers, benzophenone, diethoxyacetophenone, and Michler'"'"'s ketone.