Active energy ray curable hot melt silicone composition, cured product thereof, and method of producing film

Patent metadata

Field	Value
Publication number	US-10604653-B2
Application number	US-201615769335-A
Country	US
Kind code	B2
Filing date	Oct 12, 2016
Priority date	Oct 19, 2015
Publication date	Mar 31, 2020
Grant date	Mar 31, 2020

Abstract

Disclosed is an active energy ray curable hot melt silicone composition that is non-flowable at 25° C. and has a viscosity of 1,000 Pa·s or less at 100° C. The active energy ray curable hot melt silicone composition comprises: (A) a mixture of (A1) an organopolysiloxane having an aliphatic unsaturated bond-containing organic group and (A2) an organopolysiloxane optionally having an aliphatic unsaturated bond-containing organic group, (B) a compound having at least two mercapto groups in a molecule, and (C) a photoradical initiator. A cured product and a method of making a film are also disclosed.

First claim

The invention claimed is:

1. An active energy ray curable hot melt silicone composition that is non-flowable at 25° C. and has a viscosity of 1,000 Pa·s or less at 100° C., comprising:
(A) 100 parts by mass of an organopolysiloxane mixture containing from 10 to 50% by mass of component (A-1) below and from 50 to 90% by mass of component (A-2):
(A-1) an organopolysiloxane represented by the following average unit formula:
(R 1 3 Si O 1/2 ) a (R 1 2 SiO 2/2 ) b (R 1 SiO 3/2 ) c (SiO 4/2 ) d

wherein, each R 1 independently is a methyl group, a phenyl group, or an organic group having an aliphatic unsaturated bond, with the proviso that from 0.01 to 1 mol % of all R 1 are organic groups having an aliphatic unsaturated bond and 90 mol % or greater of the other R 1 are methyl groups, a is a number from 0 to 0.05, b is a number from 0.9 to 1, c is a number from 0 to 0.03, d is a number from 0 to 0.03, and the sum of a to d is 1,
(A-2) an organopolysiloxane represented by the following average unit formula:
(R 2 3 Si O 1/2 ) e (R 2 2 SiO 2/2 ) f (R 2 SiO 3/2 ) g (SiO 4/2 ) h (HO 1/2 ) i

wherein, each R 2 independently is a methyl group, a phenyl group, or an organic group having an aliphatic unsaturated bond, with the proviso that from 0 to 10 mol % of all R 2 are organic groups having an aliphatic unsaturated bond and 90 mol % or greater of the other R 2 are methyl groups, e is a number from 0.3 to 0.7, f is a number from 0 to 0.05, g is a number from 0 to 0.05, h is a number from 0.3 to 0.7, i is a number from 0 to 0.05, and the sum of e to h is 1;
(B) a compound having at least two mercapto groups in a molecule, in an amount such that an amount of the mercapto groups in component (B) is from 0.5 to 5.0 mol per 1 mol of the total of the organic groups having an aliphatic unsaturated bond in component (A); and
(C) a photoradical initiator in an amount that accelerates curing of the composition by an active energy ray.

2. The active energy ray curable hot melt silicone composition according to claim 1 , wherein the organic group having an aliphatic unsaturated bond in component (A) is an alkenyl group, an alkenyloxyalkyl group, an acryloxyalkyl group, or a methacryloxyalkyl group.

3. The active energy ray curable hot melt silicone composition according to claim 1 , wherein component (B) is an organopolysiloxane having at least two mercapto groups in a molecule.

4. The active energy ray curable hot melt silicone composition according to claim 1 , further comprising (D) a radical scavenger in an amount of from 0.0001 to 1 part(s) by mass per 100 parts by mass of the total amount of components (A) to (C).

5. The active energy ray curable hot melt silicone composition according to claim 1 , further comprising (E) a compound containing at least one type of metal atom selected from the group consisting of V, Ta, Nb, and Ce in an amount so that the metal atom in this component is from 5 to 2,000 ppm in terms of mass units relative to the total amount of components (A) to (C).

6. A cured product formed by curing the active energy ray curable hot melt silicone composition of claim 1 .

7. The cured product according to claim 6 , wherein the cured product is in a film form.

8. The cured product according to claim 6 , wherein a surface thereof is adhesive.

9. A method of producing a film comprising: sandwiching the active energy ray curable hot melt silicone composition described in claim 1 in between two releasable transparent resin films, forming to a fixed thickness by thermal compression or heating roller, and then irradiating the composition with an active energy ray to produce the film.

10. A film formed in accordance with the method of claim 9 .

11. The film according to claim 10 having a thickness of from 5 μm to 5 mm.

12. The cured product according to claim 7 having a thickness of from 5 μm to 5 mm.

13. The active energy ray curable hot melt silicone composition according to claim 5 , wherein component (E) comprises an organopolysiloxane containing at least one type of metal atom selected from the group consisting of V, Ta, Nb, and Ce.

14. The cured product according to claim 6 as a layer in an image display device, solar cell module, or touchscreen.

Assignees

• Dow Corning Toray Co Ltd
• Dow Toray Co Ltd

Inventors

• Dogen Ryota
• Yamazaki Haruna
• Yoshida Shin
• Yoshitake Makoto

Classifications

• C08G81/00

  Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers (involving only carbon-to-carbon unsaturated bond reactions C08F299/00 {; polyester-amides C08G69/44; polyester-imides C08G73/16; polyamides-imides C08G73/14; block- or graft polymers containing polysiloxane sequences C08G77/42}) · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08G77/28

  sulfur-containing groups · CPC title

• C08G75/045

  from mercapto compounds and unsaturated compounds · CPC title

• C09J183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title