# US 12,180,190 B2 · Additive for imparting ultraviolet absorbency and/or high refractive index to matrix, and resin member using same

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- Number: US 12,180,190 B2
- Document ID: US12180190B2
- Status: Granted
- Kind: B2
- Application number: 16/394,284
- Filed: 2019-04-25
- Published: 2019-10-17
- Granted: 2024-12-31
- Earliest claimed: 2014-08-05
- Assignees: Miyoshi Oil & Fat Co., Ltd.; Tokai Optical Co., Ltd.
- Applicants: Miyoshi Oil & Fat Co., Ltd.; Tokai Optical Co., Ltd.
- Inventors: Koji Kawai; Kotaro Kaneko; Nobuhiro Kaneko; Yuichi Shishino; Kuniyoshi Okamoto
- Web page: https://patentgrep.com/patent/US12180190B2

## CPC

- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07C 49/84: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
- C07C 69/94: of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
- C07C 321/26: Thiols
- C07C 321/28: Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C 323/20: with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C 323/22: containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07D 249/20: with aryl radicals directly attached in position 2
- C07D 251/24: to three ring carbon atoms
- C08J 5/18: Manufacture of films or sheets
- C08K 5/005: {Stabilisers against oxidation, heat, light, ozone}
- C08K 5/3475: condensed with carbocyclic rings
- C08K 5/37: Thiols
- C08K 5/372: Sulfides {, e.g. R-(S)x-R'}
- C08L 101/00: Compositions of unspecified macromolecular compounds
- C09K 3/00: Materials not provided for elsewhere
- G02B 1/04: made of organic materials, e.g. plastics (G02B1/08 takes precedence)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS

## Abstract

Provided is an additive for imparting ultraviolet absorbency, or an additive for imparting a high refractive index, which has satisfactory compatibility with a resin serving as a matrix and can maintain high transparency even if added in high concentrations. Also provided is an additive with which the function of imparting both ultraviolet absorbency and a high refractive index can be realized by means of one kind of additive. This additive is represented by the following Formula (I): wherein at least one of R1a to R9a is a monovalent sulfur-containing group represented by the following Formula (i-1) or Formula (i-2): wherein R10a to R12a each represent a divalent hydrocarbon group or the like; and R13a represents a monovalent hydrocarbon group or the like.

## Claims

### Claim 1

A method for imparting ultraviolet absorbency and/or increasing refractive index to a matrix, comprising combining the matrix with an additive represented by the following Formula (I):
wherein:
R1a, R2a, R3a, R4a, and R5a each independently represent a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or a hydroxyl group, wherein at least one of R1a, R2a, R3a, R4a, and R5a represents a methyl group;
R6a, R7a, R8a and R9a each represent a sulfur-containing monovalent group represented by the following Formula (i-2) or a hydrogen atom, wherein at least one of R6a, R7a, R8a and R9a represents the sulfur-containing monovalent group of Formula (i-2):
n and p each represent 0;
R13a represents a reactive functional group selected from the group consisting of a hydrocarbon group substituted with a hydroxyl group, a hydrocarbon group substituted with a thiol group, a hydrocarbon group substituted with a carboxyl group, a hydrocarbon group substituted with an amino group, a hydrocarbon group substituted with a silyl group, and a group containing a carbon-carbon double bond, wherein the group containing a carbon-carbon double bond is selected from the group consisting of a vinyl group, an allyl group, an acryloyl group, a methacryloyl group, a maleoyl group and a styryl group, and wherein each hydrocarbon is that in which a proximal terminal carbon is optionally interrupted by, a hydrogen atom is optionally substituted with, or a carbon-carbon bond is optionally interrupted by a monovalent or divalent group selected from the group consisting of an aromatic group, an unsaturated group, a sulfur-containing group, an oxygen-containing group, a phosphorus-containing group, an alicyclic group and a halogen atom, and
wherein:
the matrix is transparent; and
the additive represented by the Formula (I) has a light absorption peak present in a wavelength range of 350 to 390 nm in a 100 μM chloroform solution, the absorption peak present in the wavelength range is a maximum absorption wavelength (λmax), and a gradient at a longer wavelength side of the absorption peak is 0.025 or more, wherein the gradient of a straight line is connected between an absorption peak and a peak end of an absorption spectrum at the longer wavelength side of the absorption peak.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the reactive functional group of R13a is a hydrocarbon group substituted with a hydroxyl group or a group containing a carbon-carbon double bond, wherein the group containing a carbon-carbon double bond is selected from the group consisting of a vinyl group, an allyl group, an acryloyl group, a methacryloyl group, a maleoyl group and a styryl group, wherein the hydrocarbon is that in which a proximal terminal carbon is optionally interrupted by, a hydrogen atom is optionally substituted with, or a carbon-carbon bond is optionally interrupted by a monovalent or divalent group selected from the group consisting of an aromatic group, an unsaturated group, a sulfur-containing group, an oxygen-containing group, a phosphorus-containing group, an alicyclic group and a halogen atom.

### Claim 3 (depends on 2)

The method according to claim 2, wherein the hydrocarbon group of R13a is that in which a proximal terminal carbon is optionally interrupted by, a hydrogen atom is optionally substituted with, or a carbon-carbon bond is optionally interrupted by a monovalent or divalent group selected from the group consisting of an aromatic group and an oxygen-containing group.

### Claim 4 (depends on 1)

The method according to claim 1, wherein each hydrocarbon group of R13a is an alkyl group having 1 to 8 carbon atoms.

### Claim 5

A method for imparting ultraviolet absorbency and/or increasing refractive index to a matrix, comprising combining the matrix with an additive represented by the following Formula (I):
wherein:
R1a, R2a, R3a, R4a, R5a, R6a, R7a, R8a and R9a each independently represent a monovalent group selected from the group consisting of a monovalent sulfur-containing group represented by the following Formula (i-2), a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, an aromatic group, a sulfur-containing group, an oxygen-containing group, a phosphorus-containing group, an alicyclic group, and a halogen atom:
wherein in Formula (i-2),
R11a represents a divalent hydrocarbon group having 1 to 20 carbon atoms;
R12a represents, or if p is 2 or larger, R12a's each independently represent, a divalent hydrocarbon group having 1 to 20 carbon atoms;
R13a represents a monovalent hydrocarbon group having 1 to 20 carbon atoms;
the total number of carbon atoms of R11a, R12a, and R13a is 25 or less;
n represents 0;
p represents an integer from 0 to 3; and
the monovalent sulfur-containing group of Formula (i-2) is present at one or more of the positions of R1a, R2a, R3a, R4a, and R5a.

### Claim 6 (depends on 5)

The method according to claim 5, wherein R11a and R12a are each an alkylene group having 18 or fewer carbon atoms; and R13a is an alkyl group having 18 or fewer carbon atoms.

### Claim 7 (depends on 5)

The method according to claim 5, wherein R11a and R12a are each an alkylene group having 8 or fewer carbon atoms; and R13a is an alkyl group having 8 or fewer carbon atoms.

### Claim 8 (depends on 1)

The method according to claim 1, wherein R1a, R2a, R3a, R4a, and R5a contain no more than one t-butyl group.

### Claim 9 (depends on 8)

The method according to claim 8, wherein R1a represents a hydroxyl group, R2a represents a t-butyl group, R3a represents a hydrogen atom, R4a represents a methyl group, and R5a represents a hydrogen atom.