Radiation-curable release compositions

• US 5,510,190 A
• Filed: 02/27/1995
• Issued: 04/23/1996
• Est. Priority Date: 02/27/1995
• Status: Expired due to Fees

• Current Assignee: Avery Dennison Corporation
• Original Assignee: Avery Dennison Corporation
• Inventors: Allen, John, Yu, Qun
• Primary Examiner(s): Dean, Ralph H.
• Assistant Examiner(s): MOORE, MARGARET G
• Application Number:
  US08/394,572
• Time in Patent Office: 421 Days
• Field of Search: 525/477, 522/99, 428/448, 428/449, 428/447
• US Class Current: 428/448
• CPC Class Codes: C08L 2666/28 Non-macromolecular organic substances
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/06 containing silicon bound to oxygen-containing groups C08L83/12 takes precedence
• CPC Class Codes: C09D 183/06 containing silicon bound to oxygen-containing groups C09D183/12 takes precedence
• CPC Class Codes: C09J 2301/416 use of irradiation
• CPC Class Codes: C09J 2483/005 in the release coating
• CPC Class Codes: C09J 7/401 characterised by the release coating composition
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

A radiation-curable release composition is disclosed which comprises:

(A) an organopolysiloxane represented by the formula

RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n

(Si(CH₃)(R)O)_m Si(CH₃)₂ R (I)

wherein in Formula (I), each R is --R¹ --O(O)C--C(R²)═CH₂, --R¹ --O--C(R²)═CH₂ or ##STR1## R¹ is a hydrocarbylene group; each R² is independently hydrogen or a methyl or ethyl group; m is a number from about 1 to about 15; and n is a number from about 50 to about 300; and

(B) an organosiloxane polymer represented by the formula

(R.sub.3 SiO)(Si(CH.sub.3).sub.2 O).sub.n (SiR.sub.3)

wherein in Formula (II), each R is independently a hydrocarbon group and n is a number in the range of about 1000 to about 20,000. A method of producing release-coated substrates, the release-coated articles thus produced, and multi-layer articles or constructions incorporating a release layer also are disclosed. When the release compositions are cured such as by radiation, the cured compositions exhibit a desirable high and controlled release force at high speeds such as the speeds utilized in label processing.

Claims

1. A radiation-curable release composition, comprising:

(A) an organopolysiloxane represented by the formula

space="preserve" listing-type="equation">RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I)

wherein in Formula (I), each R is --R¹ --O(O)C--C(R²)═

CH₂, --R¹ --O--C(R²)═

CH₂ or ##STR4## R¹ is a hydrocarbylene group;

each R² is independently hydrogen or a methyl or ethyl group;

m is a number from 1 to about 15; and

n is a number from about 50 to about 300; and

(B) an organosiloxane polymer represented by the formula

space="preserve" listing-type="equation">(R.sub.3 SiO)(Si(CH.sub.3).sub.2 O).sub.n (SiR.sub.3) (II)

wherein in Formula (II), each R is independently a hydrocarbon group and n is a number in the range of about 1000 to about 20,000.

2. The composition of claim 1 wherein said composition further comprises

(C) a photoinitiator.

3. The composition of claim 1 wherein in Formula (I), R¹ is an aliphatic, cycloaliphatic or aromatic group of up to about 10 carbon atoms.

4. The composition of claim 1 wherein in Formula (I), each R² is hydrogen.

5. The composition of claim 1 wherein R is 4-vinyl cyclohexene epoxide.

6. The composition of claim 1 wherein R is vinyl ether.

7. The composition of claim 1 wherein in Formula (II), n is a number in the range of about 5,000 to about 15,000.

8. The composition of claim 1 wherein in Formula (II), each R group contains up to about 10 carbon atoms.

9. The composition of claim 1 wherein in Formula (II), each R group is an alkyl group of about 2 to about 6 carbon atoms.

10. The composition of claim 1 wherein (B) is a silicone gum.

11. The composition of claim 2 wherein said photoinitiator (C) is a compound selected from the group consisting of:

2,2-diethoxyacetophenone;

2- or 3- or 4-bromoacetophenone;

benzoin;

benzophenone;

4-chlorobenzophenone;

4-phenylbenzophenone;

benzoquinone;

1-chloroanthroquinone;

p-diacetyl-benzene;

9,10-dibromoanthracene;

1,3-diphenyl-2-propanone;

1,4-naphthyl-phenyl ketone;

2,3-pentenedione;

propiophenone;

chlorothioxanthone;

xanthone;

fluorenone; and

mixtures of two or more thereof.

12. A method of producing a release coated substrate which comprises

applying a coating of the composition of claim 1 to a substrate;

and

curing the coating on the substrate by exposing the coating to radiation.

13. The method of claim 12 wherein the composition is cured with ultraviolet light.

14. A release-coated article comprising a substrate which has been coated with the release composition of claim 1 and which has been cured by exposure to radiation.

15. The release-coated article of claim 14 wherein the substrate is paper.

16. A multilayer article comprising

(a) a first substrate;

(b) a second substrate;

(c) a release layer comprising the release composition of claim 1 which has been cured by exposure to radiation; and

(d) a pressure-sensitive adhesive layer, wherein the release layer (c) is interposed between the first substrate and the layer of pressure-sensitive adhesive (d) and is adherent to the first substrate, and the pressure sensitive adhesive layer (d) is interposed between the release layer and the second substrate and is adherent to the second substrate.

17. The multilayer article of claim 16 wherein the first and second substrates are paper.

18. A radiation-curable release composition, comprising:

(A) an organopolysiloxane represented by the formula

space="preserve" listing-type="equation">RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I)

wherein in Formula (I), R is --(CH₂)₆ OC(O)CH═

CH₂ ;

m is a number from about 2 to about 10; and

n is a number from about 75 to about 125; and

(B) an organosiloxane polymer represented by the formula

space="preserve" listing-type="equation">(R.sub.3 SiO)(Si(CH.sub.3).sub.2 O).sub.n (SiR.sub.3) (II)

wherein in Formula (II), each R is independently a hydrocarbon group and n is a number in the range of about 1000 to about 20,000.

19. A radiation-curable release composition, comprising:

(A) an organopolysiloxane represented by the formula

space="preserve" listing-type="equation">RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I)

wherein in Formula (I), R is --(CH₂)₆ OC(O)CH═

CH₂ ;

m is about 6; and

n is about 136; and

(B) an organosiloxane polymer represented by the formula

space="preserve" listing-type="equation">(R.sub.3 SiO)(Si(CH.sub.3).sub.2 O).sub.n (SiR.sub.3) (II)

wherein in Formula (II), each R is independently a hydrocarbon group and n is a number in the range of about 1000 to about 20,000.

20. A radiation-curable release composition, comprising:

(A) an organopolysiloxane represented by the formula

space="preserve" listing-type="equation">RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I)

wherein in Formula (I), R is --(CH₂)₆ OC(O)CH═

CH₂ ;

m is about 2; and

n is about 100; and

(B) an organosiloxane polymer represented by the formula

space="preserve" listing-type="equation">(R.sub.3 SiO)(Si(CH.sub.3).sub.2 O).sub.n (SiR.sub.3) (II)

wherein in Formula (II), each R is independently a hydrocarbon group and n is a number in the range of about 1000 to about 20,000.