Additive for imparting ultraviolet absorbency and/or high refractive index to matrix, and resin member using same

• US 10,316,024 B2
• Filed: 08/05/2015
• Issued: 06/11/2019
• Est. Priority Date: 08/05/2014
• Status: Active Grant

• Current Assignee: Miyoshi Oil & Fat Co., Ltd., Tokai Optical Co., Ltd.
• Original Assignee: Miyoshi Oil & Fat Co., Ltd., Tokai Optical Co., Ltd.
• Inventors: Kawai, Koji, Kaneko, Kotaro, Kaneko, Nobuhiro, Shishino, Yuichi, Okamoto, Kuniyoshi
• Primary Examiner(s): Balasubramanian, Venkataraman
• Application Number:
  US15/501,253
• Publication Number:
  US 20170217937A1
• Time in Patent Office: 1,406 Days
• Field of Search: 548259, 548260, 2524001
• CPC Class Codes: C07C 321/26 Thiols
• CPC Class Codes: C07C 321/28 Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 323/20 with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
• CPC Class Codes: C07C 323/22 containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
• CPC Class Codes: C07C 49/84 containing ether groups, groups, groups, or groups
• CPC Class Codes: 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
• CPC Class Codes: C07D 249/20 with aryl radicals directly attached in position 2
• CPC Class Codes: C07D 251/24 to three ring carbon atoms
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C08J 5/18 Manufacture of films or sheets
• CPC Class Codes: C08K 5/005 Stabilisers against oxidation, heat, light, ozone
• CPC Class Codes: C08K 5/3475 condensed with carbocyclic rings
• CPC Class Codes: C08K 5/37 Thiols
• CPC Class Codes: C08K 5/372 Sulfides , e.g. R-(S)x-R'
• CPC Class Codes: C08L 101/00 Compositions of unspecified macromolecular compounds
• CPC Class Codes: C09K 3/00 Materials not provided for elsewhere
• CPC Class Codes: G02B 1/04 made of organic materials, e.g. plastics G02B1/08 takes precedence

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 R^1a to R^9a is a monovalent sulfur-containing group represented by the following Formula (i-1) or Formula (i-2):

• • wherein R^10a to R^12a each represent a divalent hydrocarbon group or the like; and R^13a represents a monovalent hydrocarbon group or the like.

Claims

1. An additive represented by the following Formula (I):

2. The additive according to claim 1, wherein R^1a to R^5a are each selected from the group consisting of a methyl group, a t-butyl group and a hydroxyl group, wherein R^1a to R^5a contain no more than one t-butyl group.

3. The additive according to claim 2, wherein R^13a represents a linear alkyl group having 4 to 12 carbon atoms.

4. The additive according to claim 3, wherein R^13a represents a linear alkyl group having 6 to 10 carbon atoms.

25. A transparent resin member comprising the additive according to claim 1 in a matrix, wherein the matrix is a transparent resin.

5. An additive represented by the following Formula (I):

6. The additive according to claim 5, wherein the substituents for R^1a to R^5a and R^16a to R^20a are each selected from the group consisting of a methyl group, a t-butyl group, and a hydroxyl group, wherein R^1a to R^5a and R^16a to R^20a contain no more than one t-butyl group.

26. A transparent resin member comprising the additive according to claim 5 in a matrix, wherein the matrix is a transparent resin.

7. An additive represented by the following Formula (I):

8. The additive according to claim 7, wherein R^10a is an oxyalkylene group having an ether bond at a proximal terminal.

27. A transparent resin member comprising the additive according to claim 7 in a matrix, wherein the matrix is a transparent resin.

9. A method for imparting ultraviolet absorbency and/or a high refractive index to a matrix, comprising combining the matrix with an additive represented by the following Formula (I):

10. The method according to claim 9, wherein the substituents for R^1a to R^5a are each selected from the group consisting of a methyl group, a t-butyl group and a hydroxyl group, wherein R^1a to R^5a contain no more than one t-butyl group.

11. The method according to claim 10, wherein R^13a represents a linear alkyl group having 4 to 12 carbon atoms.

12. The method according to claim 10, wherein R^13a represents a linear alkyl group having 6 to 10 carbon atoms.

17. The method according to claim 10, wherein the matrix is a component of a member selected from the group consisting of a resin plate, an optical material, a resin film, a resin sheet, a coating agent or a protective agent for a glass, a construction material or a glass substitute, a member for a light source, a container, a packaging material, an agricultural sheet, an industrial sheet, a printed matter, a dyed good, a dye, a pigment, a coloring material, an ink, a paint, a pharmaceutical product, a cosmetic, a fabric and a discoloration preventing agent, and wherein the matrix is transparent.

18. The method according to claim 10, wherein the matrix is a component of an optical material or a resin film, wherein the optical material is an optical molded article and the resin film has a functional optical layer.

13. A method for imparting ultraviolet absorbency and/or a high refractive index to a matrix, comprising combining the matrix with an additive represented by the following Formula (I):

14. The method according to claim 13, wherein the substituents for R^1a to R^5a and R^16a to R^20a are each selected from the group consisting of a methyl group, a t-butyl group and a hydroxyl group, wherein R^1a to R^5a and R^16a to R^20a contain no more than one t-butyl group.

19. The method according to claim 13, wherein the matrix is a component of a member selected from the group consisting of a resin plate, an optical material, a resin film, a resin sheet, a coating agent or a protective agent for a glass, a construction material or a glass substitute, a member for a light source, a container, a packaging material, an agricultural sheet, an industrial sheet, a printed matter, a dyed good, a dye, a pigment, a coloring material, an ink, a paint, a pharmaceutical product, a cosmetic, a fabric and a discoloration preventing agent, and wherein the matrix is transparent.

20. The method according to claim 13, wherein the matrix is a component of an optical material or a resin film, wherein the optical material is an optical molded article and the resin film has a functional optical layer.

21. The method according to claim 14, wherein the matrix is a component of a member selected from the group consisting of a resin plate, an optical material, a resin film, a resin sheet, a coating agent or a protective agent for a glass, a construction material or a glass substitute, a member for a light source, a container, a packaging material, an agricultural sheet, an industrial sheet, a printed matter, a dyed good, a dye, a pigment, a coloring material, an ink, a paint, a pharmaceutical product, a cosmetic, a fabric and a discoloration preventing agent, and wherein the matrix is transparent.

22. The method according to claim 14, wherein the matrix is a component of an optical material or a resin film, wherein the optical material is an optical molded article and the resin film has a functional optical layer.

15. A method for imparting ultraviolet absorbency and/or a high refractive index to a matrix, comprising combining the matrix with an additive represented by the following Formula (I):

16. The method according to claim 15, wherein R^10a is an oxyalkylene group having an ether bond at a proximal terminal.

23. The method according to claim 15, wherein the matrix is a component of a member selected from the group consisting of a resin plate, an optical material, a resin film, a resin sheet, a coating agent or a protective agent for a glass, a construction material or a glass substitute, a member for a light source, a container, a packaging material, an agricultural sheet, an industrial sheet, a printed matter, a dyed good, a dye, a pigment, a coloring material, an ink, a paint, a pharmaceutical product, a cosmetic, a fabric and a discoloration preventing agent, and wherein the matrix is transparent.

24. The method according to claim 15, wherein the matrix is a component of an optical material or a resin film, wherein the optical material is an optical molded article and the resin film has a functional optical layer.