# US 10,370,473 B2 · Compound, curable composition, cured product, optical member, and lens

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- Number: US 10,370,473 B2
- Document ID: US10370473B2
- Status: Granted
- Kind: B2
- Application number: 16/019,922
- Filed: 2018-06-27
- Published: 2018-10-25
- Granted: 2019-08-06
- Earliest claimed: 2015-12-28
- Assignees: FUJIFILM Corporation
- Applicants: FUJIFILM Corporation
- Inventors: Takafumi Nakayama; Shigeki Uehira; Naoyuki Morooka
- Web page: https://patentgrep.com/patent/US10370473B2

## CPC

- C08F 220/36: containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate}
- C07D 221/18: Ring systems of four or more rings
- C07D 241/38: with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D 471/04: Ortho-condensed systems
- C08F 2/44: Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
- C08F 220/301: {and one oxygen in the alcohol moiety}
- G02B 1/04: made of organic materials, e.g. plastics (G02B1/08 takes precedence)
- G02B 1/041: {Lenses}
- C08F 2/50: with sensitising agents
- C08F 216/125: {Monomers containing two or more unsaturated aliphatic radicals, e.g. trimethylolpropane triallyl ether or pentaerythritol triallyl ether}
- C08F 220/1807: {C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate}
- C08F 220/1811: {C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate}
- C08F 220/382: {and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate}
- C08F 222/102: {of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate}
- C08F 2800/20: as weight or mass percentages
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS

## Abstract

A cured product of a compound of the following formula has a low Abbe number and a high abnormal dispersibility. X and Y are O, S, N or S; Z and X—C═C—Y form 5 to 7-membered ring; R1 and R2 represents H, alkoxy, mercapto, thioalkoxy, amino, alkylamino, carboxy, alkylcarbonyloxy, carbamoyloxy or alkoxycarbonyloxy; and R3 to R6 represent substituent.

## Claims

### Claim 1

A compound represented by Formula (1),
in Formula (1), X and Y each independently represents an oxygen atom, a sulfur atom, a nitrogen atom, or a carbon atom, at least one of X or Y is an oxygen atom, a sulfur atom, or a nitrogen atom;
Z is an atomic group that forms a 5 to 7-membered ring together with X—C═C—Y and represents an atomic group including at least one selected from a carbon atom and a heteroatom;
R1 and R2 each independently represents a hydroxyl group, an alkoxy group having 2 to 6 carbon atoms that may have a substituent, a mercapto group, a thioalkoxy group having 2 to 6 carbon atoms that may have a substituent, an amino group, an alkylamino group having 1 to 6 carbon atoms that may have a substituent, a carboxy group, an alkylcarbonyloxy group having 1 to 6 carbon atoms that may have a substituent, a carbamoyloxy group that may have a substituent, or an alkoxycarbonyloxy group having 2 to 6 carbon atoms that may have a substituent;
R3 to R5 each independently represents a halogen atom, a halogenated alkyl group, an alkyl group, an alkenyl group, an acyl group, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an alicyclic group, or a cyano group;
R6 represents a halogen atom, a halogenated alkyl group, an alkyl group, an alkenyl group, an acyl group, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an alicyclic group, or a cyano group;
m and n each independently represents an integer of 1 to 5, q and r each independently represents an integer of 0 to 4; here, 1≤m+q≤5, and 1≤n+r≤5 are satisfied;
v is an integer of 0 to 4, w is an integer of 0 or more, the maximum number of w is the maximum number of substituents that may be substituted with a ring formed by X—C═C—Y and Z;
in a case where q is an integer of 2 to 4, the plurality of R3's may be identical to or different from each other, and the plurality of R3's may be bonded to each other to form a ring;
in a case where r is an integer of 2 to 4, the plurality of R4's may be identical to or different from each other, and the plurality of R4's may be bonded to each other to form a ring;
in a case where v is an integer of 2 to 4, the plurality of R5's may be identical to or different from each other, but the plurality of R5's are not bonded to each other to form a ring; and
in a case where w is an integer of 2 to 5, the plurality of R6's may be identical to or different from each other, and the plurality of R6's may be bonded to each other to form a ring, provided that in a case where a plurality of R6's are bonded to each other and are groups for forming a fused ring together with a substituted ring, the number of rings for forming a fused ring is 2.

### Claim 2 (depends on 1)

The compound according to claim 1,
wherein in Formula (1), R1 and R2 each independently represents a group having a hydroxyl group, a mercapto group, an amino group, a polymerizable unsaturated bond, an epoxy group, or an oxetanyl group.

### Claim 3 (depends on 1)

The compound according to claim 1,
wherein in Formula (1), R1 and R2 each independently represents a group represented by Formula (2);
-L1Alkylene-L2n1P Formula (2)
in Formula (2), L1 represents —O—, —S—, or —NH—, Alkylene represents an alkylene group having 2 to 6 carbon atoms, L2 represents —O—, —S—, or —NH—, n1 represents an integer of 0 to 2, P is a hydrogen atom or a group represented by any one of Formulae (P1) to (P4); and
in Formulae (P) to (P4), R511, R512, R513, R521, R522, R523, R531, R532, R533, R541, R542, R543, R544, and R545 each independently represents a hydrogen atom or an alkyl group, m represents an integer of 0 to 2, and R11 and R12 each independently represents a hydrogen atom, a halogen atom, a halogenated alkyl group, an alkyl group, an alkenyl group, an acyl group, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an alicyclic group, a cyano group, an epoxy group, an oxetanyl group, a mercapto group, an amino group, or a (meth)acryloyl group.

### Claim 4 (depends on 1)

The compound according to claim 1,
wherein, in Formula (1), at least one selected from X and Y is a nitrogen atom.

### Claim 5 (depends on 1)

The compound according to claim 1,
wherein, in Formula (1), R1 and R2 are the same group.

### Claim 6 (depends on 1)

The compound according to claim 1, which is represented by Formula (3);
in Formula (3), R1 and R2 each independently represents a hydroxyl group, an alkoxy group having 2 to 6 carbon atoms that may have a substituent, a mercapto group, a thioalkoxy group having 2 to 6 carbon atoms that may have a substituent, an amino group, an alkylamino group having 1 to 6 carbon atoms that may have a substituent, a carboxy group, an alkylcarbonyloxy group having 1 to 6 carbon atoms that may have a substituent, a carbamoyloxy group that may have a substituent, or an alkoxycarbonyloxy group having 2 to 6 carbon atoms that may have a substituent;
R3 to R5 each independently represents a halogen atom, a halogenated alkyl group, an alkyl group, an alkenyl group, an acyl group, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an alicyclic group, or a cyano group;
R6 represents a halogen atom, a halogenated alkyl group, an alkyl group, an alkenyl group, an acyl group, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an alicyclic group, or a cyano group;
m and n each independently represents an integer of 1 to 5, q and r each independently represents an integer of 0 to 4; here, 1≤m+q≤5, and 1≤n+r≤5 are satisfied;
v is an integer of 0 to 4, and w is an integer of 0 to 2;
in a case where q is an integer of 2 to 4, the plurality of R3's may be identical to or different from each other, and the plurality of R3's may be bonded to each other to form a ring;
in a case where r is an integer of 2 to 4, the plurality of R4's may be identical to or different from each other, and the plurality of R4's may be bonded to each other to form a ring;
in a case where v is an integer of 2 to 4, the plurality of R5's may be identical to or different from each other, but the plurality of R5's are not bonded to each other to form a ring; and
in a case where w is 2, the plurality of R6's may be identical to or different from each other, and the plurality of R6's may be bonded to each other to form a ring, provided that in a case where a plurality of R6's are bonded to each other and are groups for forming a fused ring together with a substituted ring, the number of rings for forming a fused ring is 2.

### Claim 7 (depends on 1)

The compound according to claim 1,
wherein R1 and R2 are each independently represented by Formula (4);
in Formula (4), L represents —O—, —S—, or —NH—, Alkylene represents an alkylene group having 2 to 6 carbon atoms, and R531, R532, and R533 each independently represents a hydrogen atom or an alkyl group.

### Claim 8 (depends on 1)

A curable composition comprising the compound according to claim 1.

### Claim 9 (depends on 8)

The curable composition according to claim 8,
wherein the curable composition contains a (meth)acrylate monomer and at least one selected from a photoradical polymerization initiator and a thermal radical polymerization initiator.

### Claim 10 (depends on 9)

The curable composition according to claim 9,
wherein viscosity of the (meth)acrylate monomer of the curable composition at 25° C. is less than 2,000 mPa·s.

### Claim 11 (depends on 8)

A cured product of the curable composition according to claim 8.

### Claim 12 (depends on 11)

An optical member comprising the cured product according to claim 11.

### Claim 13 (depends on 11)

A lens comprising the cured product according to claim 11.

### Claim 14 (depends on 1)

The compound according to claim 1,
wherein, in Formula (1), R3 to R6 each independently represents a halogen atom, an alkyl group, an alkoxy group, an aryl group, or a cyano group.

### Claim 15 (depends on 3)

The compound according to claim 3, wherein, in Formulae (P1) to (P4), R11 and R12 each independently represents a hydrogen atom or an alkyl group.