Active energy ray-curable resin composition, resin molded article, and method for producing resin molded article

Patent metadata

Field	Value
Publication number	US-11248065-B2
Application number	US-201816217635-A
Country	US
Kind code	B2
Filing date	Dec 12, 2018
Priority date	Jul 1, 2016
Publication date	Feb 15, 2022
Grant date	Feb 15, 2022

Abstract

An active energy ray-curable resin composition which contains (A) inorganic oxide particles each having an organic functional group on the surface, (B) a siloxane oligomer which has at least one functional group selected from the group consisting of a (meth)acryloyl group, an epoxy group and a vinyl group, while having a weight average molecular weight of 200-3,000, (C) a polyfunctional (meth)acrylate having a specific structure, (D) a urethane (meth)acrylate having two or more (meth)acryloyl groups in each molecule, and (E) an ultraviolet absorbent.

First claim

The invention claimed is:

1. An active energy ray-curable resin composition, comprising:
a component (A): inorganic oxide particles having an organic functional group on a front surface;
a component (B): a siloxane oligomer having at least one type of functional group selected from the group consisting of a (meth)acryloyl group, an epoxy group, and a vinyl group, of which a weight average molecular weight is 200 to 3000;
a component (C): polyfunctional (meth)acrylate represented by Formula (1) described below;
a component (D): urethane (meth)acrylate containing two or more (meth)acryloyl groups in one molecule; and
a component (E): an ultraviolet ray absorber,
wherein with respect to 100 parts by mass of the total of the components (A), (B), (C), and (D),
a content of the component (A) is 4 parts by mass to 30 parts by mass,
a content of the component (B) is 2 parts by mass to 20 parts by mass,
a content of the component (C) is 30 parts by mass to 80 parts by mass, and
a content of the component (D) is 5 parts by mass to 50 parts by mass, and
the content of the component (C) is greater than or equal to 60 parts by mass, with respect to 100 parts by mass of the total of (meth)acrylate other than three components of the component (A), the component (B), and the component (D),

in the formula, at least three of the X groups, are each independently,
a modified group (CH 2 ═CR—CO(OC 2 H 4 ) y —O—) of a (meth)acryloyl group modified with ethylene oxide (R represents a hydrogen atom or a methyl group, and y represents an integer of greater than or equal to 1 and less than or equal to 5),
a modified group (CH 2 ═CR—CO(OC 3 H 6 ) y —O—) of a (meth)acryloyl group modified with propylene oxide (R represents a hydrogen atom or a methyl group, and y represents an integer of greater than or equal to 1 and less than or equal to 5),
a modified group (CH 2 ═CR—CO(O(CH 2 ) 5 C═O) y —O—) of a (meth)acryloyl group modified with caprolactone (R represents a hydrogen atom or a methyl group, and y represents an integer of greater than or equal to 1 and less than or equal to 5), or
a (meth)acryloyl oxy group (CH 2 ═CR—COO—) (R represents a hydrogen atom or a methyl group), and
the remaining Xs are a methyl group or a hydroxy group (—OH), and n is an integer of 0 to 4.

2. The active energy ray-curable resin composition according to claim 1 ,
wherein a mass ratio (A/B) of the component (A) to the component (B), is in a range of 0.5 to 8.

3. The active energy ray-curable resin composition according to claim 1 ,
wherein the component (D) is a reactant of,
diisocyanate having an alicyclic structure,
polycarbonate polyol having a branched alkyl structure, of which a number average molecular weight is in a range of 500 to 1000, and
mono(meth)acrylate having a hydroxyl group.

4. The active energy ray-curable resin composition according to claim 1 ,
wherein the component (E) contains a hydroxyphenyl triazine-based ultraviolet ray absorber.

5. The active energy ray-curable resin composition according to claim 1 ,
wherein the component (E) contains an ultraviolet ray absorber of which a light absorbance at a wavelength of 350 nm is greater than or equal to 1.0.

6. The active energy ray-curable resin composition according to claim 1 , further comprising:
a photopolymerization initiator having maximum absorption at a wavelength of 360 nm to 400 nm, as a component (F).

7. The active energy ray-curable resin composition according to claim 1 , wherein a resin laminate obtained by laminating a cured film of the active energy ray-curable resin composition on a front surface of a transparent resin base material to have a thickness of greater than or equal to 5 μm, satisfies requisites (α), (β), and (γ) described below,
(α) in a Taber wear resistance test based on ASTM D1044 (a load 500 gf (4.90 N), and 500 rotations), a haze difference before and after a wear test is less than or equal to 15%,
(β) in a steel wool abrasion resistance test based on FMVSS 108 (14 kPa, steel wool #0000, and 11 reciprocal slidings), a haze difference before and after an abrasion test is less than 1%, and
(γ) a haze difference of the resin laminate before and after an accelerated weather resistance test of repeating light irradiation of a sunshine carbon arc lamp type weather resistance tester based on JIS D 0205 (an irradiation intensity: 255 W/m 2 at 300 nm to 700 nm, continuous irradiation, a temperature: a black panel temperature of 63° C.±3° C., and rainfall for 12 minutes in 1 hour), is performed for 5000 hours, is less than or equal to 2%.

8. The active energy ray-curable resin composition according to claim 1 , wherein a resin laminate obtained by laminating a cured film of the active energy ray-curable resin composition on a front surface of a transparent resin base material to have a thickness of greater than or equal to 10 μm, satisfies requisites (α), (β), and (γ) described below,
(α) in a Taber wear resistance test based on ASTM D1044 (a load of 500 gf (4.90 N), and 500 rotations), a haze difference before and after a wear test is less than or equal to 15%,
(β) in a steel wool abrasion resistance test based on FMVSS 108 (14 kPa, steel wool #0000, and 11 reciprocal slidings), a haze difference before and after an abrasion test is less than 1%, and
(γ) a haze difference of the resin laminate before and after an accelerated weather resistance test of repeating light irradiation of a sunshine carbon arc lamp type weather resistance tester based on JIS D 0205 (an irradiation intensity: 255 W/m 2 at 300 nm to 700 nm, continuous irradiation, a temperature: a black panel temperature of 63° C.±3° C., and rainfall for 12 minutes in 1 hour) is performed for 7000 hours, is less than or equal to 2%.

9. A resin molded article,
wherein a cured film of the active energy ray-curable resin composition according to claim 1 , is formed on a front surface of a resin molding base.

10. The resin molded article according to claim 9 ,
wherein the resin molded article is an automotive headlamp lens.

11. A method of producing the resin molded article according to claim 9 , the method comprising:
a step of applying the active energy ray-curable resin composition onto the front surface of the resin molding base, and of irradiating the active energy ray-curable resin composition with an active energy ray.

12. A resin molded article,
wherein a cured film of the active energy ray-curable resin composition according to claim 7 , is formed on a front surface of a resin molding base.

13. The resin molded article according to claim 12 ,
wherein the resin molded article is an automotive headlamp lens.

14. A resin molded article,
wherein a cured film of the active energy ray-curable resin composition according to claim 8 , is formed on a front surface of a resin molding base.

15. The resin molded article according to claim 14 ,
wherein the resin molded article is an automotive headlamp lens.

16. A method of producing the resin molded article according to claim 12 , the method comprising:
a step of applying the active energy ray-curable resin composition onto the front surface of the resin molding base, and of irradiating the active energy ray-curable resin composition with an active energy ray.

17. A method of producing the resin molded article according to claim 14 , the method comprising:
a step of applying the active energy ray-curable resin compos

Assignees

• Mitsubishi Chem Corp

Inventors

• Miyachi Akira
• Kanbara Riina
• Serizawa Masashi

Classifications

• C08J7/046

  Forming abrasion-resistant coatings; Forming surface-hardening coatings · CPC title

• C08F290/067

  Polyurethanes; Polyureas · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C09D183/06

  containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence) · CPC title

• C09D4/06

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00 · CPC title