IP Library › Granted Patent US 11,591,440
Granted Patent B2
US 11,591,440 · App. 16/760,538 · Granted Feb 28, 2023

Method for producing organopolysiloxane cured product, organopolysiloxane cured product, layered product, and optical part

Inventor: Makoto Yoshitake (Ichihara, JP)
Assignee: DOW TORAY CO., LTD.
C08G77/08B32B27/283C08G77/14C08G77/20C08J3/24C08J3/28B32B2310/08B32B2551/00
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Quick Facts
Patent No.
US 11,591,440
App. No.
16/760,538
Granted
Feb 28, 2023
Kind
B2
Abstract

Provided is a cured product using a composition that is capable of quick curing at low temperatures while having sufficient pot life at room temperature, a method of producing the same, a laminate, and an optical device. A method of producing an organopolysiloxane cured product is provided. The method includes: (i) performing, without irradiating with high-energy radiation, a hydrosilylation reaction upon a composition containing a first hydrosilylation reaction catalyst that exhibits activity in the composition and a second hydrosilylation reaction catalyst that does not exhibit activity when not irradiated with high-energy radiation, but exhibits activity in the composition when irradiated with high-energy radiation, to obtain a thickened material that is fluid at room temperature or a thermoplastic material that is non-fluid at room temperature but exhibits fluidity at 100° C.; and (ii) irradiating the thickened material or thermoplastic material obtained in step (i) with high-energy radiation to obtain a cured product.

Claims (45)

1. A laminate wherein an organopolysiloxane cured product is disposed between layers, and wherein the organopolysiloxane cured product is produced via a method including:

(i) performing, without irradiating with high-energy radiation, a hydrosilylation reaction upon a composition comprising:

(A) an organopolysiloxane represented by the following average composition formula (1):

R 1 a R 2 b SiO (4-a-b)/2   (1);

wherein R 1 is an alkenyl group comprising 2-12 carbon atoms; R 2 is a group selected from a monovalent hydrocarbon group comprising 1-12 carbon atoms and not comprising an aliphatic unsaturated bond, a hydroxyl group and an alkoxy group; and a and b are numbers satisfying the following conditions: 1≤a+b≤3 and 0.001≤a/(a+b)≤0.33;

(B) an organopolysiloxane represented by the following average composition formula (2):

H c R 3 d SiO (4-c-d)/2   (2);

wherein R 3 is a group selected from a monovalent hydrocarbon group comprising 1-12 carbon atoms and not comprising an aliphatic unsaturated bond, a hydroxyl group, and an alkoxy group; and c and d are numbers satisfying the following conditions: 1≤c+d≤3 and 0.01≤c/(c+d)≤0.33;

(C) a first hydrosilylation reaction catalyst that exhibits activity in the composition without being irradiated with high-energy radiation; and

(D) a second hydrosilylation reaction catalyst that does not exhibit activity when not irradiated with high-energy radiation, but exhibits activity in the composition when irradiated with high-energy radiation;

to obtain a thickened material that is fluid at room temperature, or a thermoplastic material that is non-fluid at room temperature but exhibits fluidity at 100° C.; and

(ii) irradiating the thickened material or thermoplastic material obtained in step (i) with high-energy radiation.

2. The laminate according to claim 1 , wherein the high-energy radiation is selected from the group consisting of ultraviolet radiation, gamma radiation, X-ray radiation, alpha radiation, and electron beam radiation.

3. The laminate according to claim 1 , wherein component (B) is an organohydrogen polysiloxane represented by the following average unit formula (3):

(HR 4 2 SiO 1/2 ) e (R 4 3 SiO 1/2 ) f (HR 4 SiO 2/2 ) g (R 4 2 SiO 2/2 ) h (HSiO 3/2 ) i (R 4 SiO 3/2 ) j (SiO 4/2 ) k (R 5 O 1/2 ) l   (3);

wherein each R 4 is, independently, a group selected from a monovalent hydrocarbon group comprising 1-12 carbon atoms and not comprising an aliphatic unsaturated bond, a hydroxyl group, and an alkoxy group; R 5 is a hydrogen atom or an alkyl group comprising 1-6 carbon atoms; and e, f, g, h, i, j, k, and 1 are numbers satisfying the following conditions: e+f+g+h+i+j+k=1, 0≤1≤0.1, 0.01≤e+g+i≤0.2, 0≤e≤0.6, 0≤g≤0.6, 0≤i≤0.4, 0.01≤e+f≤0.8, 0.01≤g+h≤0.8, 0≤i+j≤0.6.

4. The laminate according to claim 1 , wherein the molar ratio ((C)/(D)) of component (C) and component (D) is 0.001-1000.

5. The laminate according to claim 1 , wherein the product is an image display device.

6. An optical device comprising the laminate according to claim 1 .

7. A method of manufacturing a laminate in which an organopolysiloxane cured product is disposed between layers, the method including providing a composition comprising:

(A) an organopolysiloxane represented by the following average composition formula (1):

R 1 a R 2 b SiO (4-a-b)/2   (1);

wherein R 1 is an alkenyl group comprising 2-12 carbon atoms; R 2 is a group selected from a monovalent hydrocarbon group comprising 1-12 carbon atoms and not comprising an aliphatic unsaturated bond, a hydroxyl group and an alkoxy group; and a and b are numbers satisfying the following conditions: 1≤a+b≤3 and 0.001≤a/(a+b)≤0.33;

(B) an organopolysiloxane represented by the following average composition formula (2):

H c R 3 d SiO (4-c-d)/2   (2);

wherein R 3 is a group selected from a monovalent hydrocarbon group comprising 1-12 carbon atoms and not comprising an aliphatic unsaturated bond, a hydroxyl group, and an alkoxy group; and c and d are numbers satisfying the following conditions: 1≤c+d≤3 and 0.01≤c/(c+d)≤0.33;

(C) a first hydrosilylation reaction catalyst that exhibits activity in the composition without being irradiated with high-energy radiation; and

(D) a second hydrosilylation reaction catalyst that does not exhibit activity when not irradiated with high-energy radiation, but exhibits activity in the composition when irradiated with high-energy radiation.

8. The method of manufacturing a laminate according to claim 7 , the method including:

(iii) applying the composition comprising components (A) through (D) to a substrate, and performing a hydrosilylation reaction without irradiating with high-energy radiation to form a layer of a thickened material that is fluid at room temperature, or a thermoplastic material that is non-fluid at room temperature but exhibits fluidity at 100° C.;

(iv) forming an upper layer member over the layer of thickened material or thermoplastic material obtained in step (iii); and

(v) irradiating the layer of thickened material or thermoplastic material with high-energy radiation from at least one of below the substrate, above the upper layer member, and the side of the layer of thickened material or thermoplastic material.

9. A laminate obtained via the method according to claim 8 .

10. The method of manufacturing a laminate according to claim 7 , the method including:

(vi) applying the composition comprising components (A) through (D) to a substrate, and performing a hydrosilylation reaction without irradiating with high-energy radiation to form a layer of a thickened material that is fluid at room temperature, or a thermoplastic material that is non-fluid at room temperature but exhibits fluidity at 100° C.;

(vii) irradiating the layer of thickened material or thermoplastic material obtained in step (vi) with high-energy radiation;

(viii) forming an upper layer member over the layer of thickened material or thermoplastic material following irradiation with the high-energy radiation; and

(ix) curing the layer of thickened material or thermoplastic material by heating or letting stand at room temperature.

11. A laminate obtained via the method according to claim 10 .

12. The method of manufacturing a laminate according to claim 7 , the method including:

(x) applying the composition comprising components (A) through (D) to a substrate, and performing a hydrosilylation reaction without irradiating with high-energy radiation to form a layer of a thickened material that is fluid at room temperature, or a thermoplastic material that is non-fluid at room temperature but exhibits fluidity at 100° C.;

(xi) irradiating the layer of thickened material or thermoplastic material obtained in step (x) with high-energy radiation;

(xii) forming an upper layer member over the layer of thickened material or thermoplastic material following irradiation with the high-energy radiation; and

(xiii) irradiating the layer of thickened material or thermoplastic material with high-energy radiation from at least one of below the substrate, above the upper layer member, and the side of the layer of thickened material or thermoplastic material.

13. A laminate obtained via the method according to claim 12 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 11, 2023
From: YOSHITAKE, MAKOTO
To: DOW TORAY CO., LTD.
Reel/Frame 062343/0009 →
Priority Claims (1)
JP JP2017-211400 · Oct 31, 2017 · national
Continuity (1)
Related Publication 20210179783A1 · Jun 17, 2021