IP Library Granted Patent US 12662558
Granted Patent B2
US 12662558 · App. 18/152,123 · Granted Jun 23, 2026

Polymerizable composition, polymer, ultraviolet shielding material, laminate, compound, ultraviolet absorbing agent, and method of producing compound

Inventors: Yoshihiro Jimbo (Shizuoka, JP); Daisuke Sasaki (Shizuoka, JP)
Assignee: FUJIFILM Corporation
C08F20/38C07D249/20C07D409/04C08F220/14C08F220/387G02B1/04
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Quick Facts
Patent No.
US 12662558
App. No.
18/152,123
Granted
Jun 23, 2026
Kind
B2
Abstract

Provided is a polymerizable composition including a compound represented by Formula (1), and an ultraviolet absorbing agent A having a maximum absorption wavelength on a shorter wavelength side than a maximum absorption wavelength of the compound represented by Formula (1). Provided are a polymer, an ultraviolet shielding material, a laminate, a compound, an ultraviolet absorbing agent, and a method of producing a compound. In Formula (1), R 1 to R 6 each independently represent a hydrogen atom or a substituent, where at least one of R 1 to R 6 represents a group that contains a polymerizable group having an ethylenically unsaturated bond.

Claims (68)

1 . A polymerizable composition comprising:

a compound represented by Formula (1); and

an ultraviolet absorbing agent A having a maximum absorption wavelength on a shorter wavelength side than a maximum absorption wavelength of the compound represented by Formula (1),

in Formula (1), R 1 to R 6 each independently represent a hydrogen atom or a substituent,

R 1 and R 2 may be bonded to each other to form a ring, and

R 3 and R 4 may be bonded to each other to form a ring,

where at least one of R 1 to R 6 represents a group that contains a polymerizable group having an ethylenically unsaturated bond.

2 . The polymerizable composition according to claim 1 ,

wherein the compound represented by Formula (1) is a compound represented by Formula (2),

in Formula (2), R 11 and R 12 each independently represent a hydrogen atom, an alkyl group, or an aryl group,

R 13 and R 14 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, or an aryloxy group,

X 11 and X 12 each independently represent a single bond, —O—, —OC(═O)—, —OC(═O)O—, or —OC(═O)NRx 11 -, where Rx 11 represents a hydrogen atom, an alkyl group, or an aryl group,

Y 11 and Y 12 each independently represent a single bond or a divalent linking group,

Z 11 and Z 12 each independently represent a hydrogen atom or a polymerizable group having an ethylenically unsaturated bond,

R 11 and R 12 may be bonded to each other to form a ring, and

R 13 and R 14 may be bonded to each other to form a ring,

where at least one of Z 11 or Z 12 represents a polymerizable group having an ethylenically unsaturated bond.

3 . The polymerizable composition according to claim 1 ,

wherein the polymerizable group having an ethylenically unsaturated bond is a (meth)acryloyloxy group or a vinylphenyl group.

4 . The polymerizable composition according to claim 1 ,

wherein the maximum absorption wavelength of the ultraviolet absorbing agent A is present in a wavelength range of 300 to 380 nm.

5 . The polymerizable composition according to claim 1 ,

wherein the ultraviolet absorbing agent A is a compound containing a polymerizable group.

6 . The polymerizable composition according to claim 1 ,

wherein the ultraviolet absorbing agent A is at least one selected from a 2-(2-hydroxyphenyl)benzotriazole-based compound, a 2-(2-hydroxyphenyl)-1,3,5-triazine-based compound, or a 2-hydroxybenzophenone-based compound.

7 . The polymerizable composition according to claim 1 , further comprising:

a polymerizable compound other than the compound represented by Formula (1); and

a polymerization initiator.

8 . A polymer which is obtained by polymerizing the polymerizable composition according to claim 1 .

9 . An ultraviolet shielding material comprising:

the polymer according to claim 8 .

10 . A laminate comprising:

a support; and

the ultraviolet shielding material according to claim 9 .

11 . A compound which is represented by Formula (5),

in Formula (5), R 51 and R 52 each independently represent a hydrogen atom, an alkyl group, or an aryl group,

R 53 represents an alkyl group and R 54 represents a hydrogen atom,

X 51 and X 52 each independently represent —O—, —OC(═O)O—, or —OC(═O)NH—,

Y 51 and Y 52 each independently represent a single bond or a divalent linking group, the divalent linking group is a hydrocarbon group or a group having a structure in which two or more hydrocarbon groups are bonded via a linking group, and the linking group represents —O—, —C(═O)—, —OC(═O)—, —C(═O)O—, —NHC(═O)—, or —C(═O)NH—, and

one of Z 51 and Z 52 represents a polymerizable group having an ethylenically unsaturated bond, and the other of Z 51 and Z 52 represents a hydrogen atom,

in a case where X 51 represents —O— and Z 51 represents the polymerizable group having an ethylenically unsaturated bond, the polymerizable group having an ethylenically unsaturated bond which is represented by Z 51 is a vinylphenyl group, and

in a case where X 52 represents —O— and Z 52 represents the polymerizable group having an ethylenically unsaturated bond, the polymerizable group having an ethylenically unsaturated bond which is represented by Z 52 is a vinylphenyl group.

12 . The compound according to claim 11 ,

wherein the polymerizable group having an ethylenically unsaturated bond is a (meth)acryloyloxy group or a vinylphenyl group.

13 . The compound according to claim 11 ,

wherein X 51 and X 52 each independently represent —O— or —OC(═O)NH—.

14 . The compound according to claim 11 ,

wherein X 51 has the same definition as that for X 52 , and Y 51 has the same definition as that for Y 52 .

15 . An ultraviolet absorbing agent comprising:

the compound according to claim 11 .

16 . A polymer which has a structure derived from the compound according to claim 11 .

17 . A method of producing a compound, comprising:

reacting a compound represented by Formula (6) with a compound represented by Formula (7) to produce a compound represented by Formula (5),

in Formula (6), R 61 and R 62 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and

R 63 represents an alkyl group and R 64 represents a hydrogen atom,

Z 71 —Y 71 -E 71   (7)

in Formula (7), E 71 represents a group that reacts with a hydroxy group of Formula (6),

Y 71 represents a single bond or a divalent linking group, the divalent linking group is a hydrocarbon group or a group having a structure in which two or more hydrocarbon groups are bonded via a linking group, and the linking group represents —O—, —C(═O)—, —OC(═O)—, —C(═O)O—, —NHC(═O)—, or —C(═O)NH—, and

Z 71 represents a polymerizable group having an ethylenically unsaturated bond,

in Formula (5), R 51 and R 52 each independently represent a hydrogen atom, an alkyl group, or an aryl group,

R 53 represents an alkyl group and R 54 represents a hydrogen atom,

X 51 and X 52 each independently represent —O—, —OC(═O)O—, or —OC(═O)NH—,

Y 51 and Y 52 each independently represent a single bond or a divalent linking group, the divalent linking group is a hydrocarbon group or a group having a structure in which two or more hydrocarbon groups are bonded via a linking group, and the linking group represents —O—, —C(═O)—, —OC(═O)—, —C(═O)O—, —NHC(═O)—, or —C(═O)NH—, and

one of Z 51 and Z 52 represents a polymerizable group having an ethylenically unsaturated bond, and the other of Z 51 and Z 52 represents a hydrogen atom,

in a case where X 51 represents —O— and Z 51 represents the polymerizable group having an ethylenically unsaturated bond, the polymerizable group having an ethylenically unsaturated bond which is represented by Z 51 is a vinylphenyl group, and

in a case where X 52 represents —O— and Z 52 represents the polymerizable group having an ethylenically unsaturated bond, the polymerizable group having an ethylenically unsaturated bond which is represented by Z 52 is a vinylphenyl group.

18 . The method of producing a compound according to claim 17 ,

wherein E 71 in Formula (7) represents —COCl, —O(C═O)Cl, —NCO, —Cl, —Br, —I, —OSO 2 D 1 , or an oxiranyl group, where D 1 represents a methyl group, an ethyl group, a phenyl group, or a 4-methylphenyl group.