Cyclic olefin-based resin composition, molded product, and optical component

Patent metadata

Field	Value
Publication number	US-12209147-B2
Application number	US-202017613969-A
Country	US
Kind code	B2
Filing date	May 14, 2020
Priority date	May 27, 2019
Publication date	Jan 28, 2025
Grant date	Jan 28, 2025

Abstract

Provided is a cyclic olefin-based resin composition including a cyclic olefin-based polymer (A), and a hindered amine compound (Y) that contains a piperidyl group represented by General Formula (1) and a carboxylic acid amide group represented by General Formula (2) within the same molecule.

First claim

The invention claimed is:

1. A cyclic olefin-based resin composition comprising:
a cyclic olefin-based polymer (A); and
a hindered amine compound (Y) that contains a piperidyl group represented by General Formula (1) and a carboxylic acid amide group represented by General Formula (2) within the same molecule,

wherein, in General Formula (1), X is a hydrogen atom, an oxyradical group, an alkyl group, an alkoxy group, an aryl group, or a hydroxy group, and R 1 to R 4 are each independently an alkyl group,
wherein the hindered amine compound (Y) further contains an alicyclic structure represented by General Formula (3) within the same molecule,

wherein, in General Formula (3), at least one of R 400 , R 401 , R 402 , R 403 , R 404 , or R 405 is a bond, and except for the bond, remainders are each independently a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and g is equal to or more than 1 and equal to or less than 18.

2. The cyclic olefin-based resin composition according to claim 1 ,
wherein the alicyclic structure represented by General Formula (3) has a spiro-bond.

3. The cyclic olefin-based resin composition according to claim 1 ,
wherein the hindered amine compound (Y) has a structure represented by General Formula (4),

wherein, in General Formula (4), at least one of R 5 , R 6 , or R 7 is a bond, and except for the bond, R 5 and R 6 are each independently a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R 7 is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a structure represented by General Formula (4-1), and

wherein, in General Formula (4-1), n is 0 to 10, and R 8 is a hydrocarbon group having 1 to 20 carbon atoms.

4. The cyclic olefin-based resin composition according to claim 1 ,
wherein the hindered amine compound (Y) includes at least one selected from a compound represented by General Formula (5) or a compound represented by General Formula (6),

wherein, in General Formula (5), n is 1 to 20.

5. The cyclic olefin-based resin composition according to claim 1 ,
the cyclic olefin-based polymer (A) includes at least one selected from a copolymer (A1) of ethylene or an α-olefin and a cyclic olefin or a ring-opening polymer (A2) of a cyclic olefin.

6. The cyclic olefin-based resin composition according to claim 5 ,
wherein the cyclic olefin-based polymer (A) includes the copolymer (A1), and the copolymer (A1) contains
a repeating unit (a) derived from at least one olefin represented by General Formula (I), and
a repeating unit (b) derived from at least one cyclic olefin selected from the group consisting of a repeating unit represented by General Formula (II), a repeating unit represented by General Formula (III), a repeating unit represented by General Formula (IV), a repeating unit represented by General Formula (V), and a repeating unit represented by General Formula (VI),

wherein, in General Formula (I), R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms,

wherein, in General Formula (II), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, R 61 to R 78 and R a1 and R b1 may be the same or different from each other and are each a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, and R 75 to R 78 may be bonded to each other to form a monocyclic ring or a polycyclic ring,

wherein, in General Formula (III), x and d are each an integer of 0 or equal to or more than 1, y and z are each 0, 1, or 2, R 81 to R 99 may be the same or different from each other and are each a hydrogen atom, a halogen atom, an aliphatic hydrocarbon group that is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 15 carbon atoms, and an aromatic hydrocarbon group having 6 to 20 carbon atoms or an alkoxy group, a carbon atom to which R 89 and R 90 are bonded and a carbon atom to which R 93 is bonded or a carbon atom to which R 91 is bonded may be bonded directly or through an alkylene group having 1 to 3 carbon atoms, and in a case of y=z=0, R 95 and R 92 or R 95 and R 99 may be bonded to each other to form a monocyclic aromatic ring or polycyclic aromatic ring,

wherein, in General Formula (IV), n and m are each independently 0, 1, or 2, q is 1, 2, or 3, R 18 to R 31 are each independently a hydrogen atom, a halogen atom excluding a fluorine atom, or a hydrocarbon group having 1 to 20 carbon atoms, which may be substituted with a halogen atom excluding a fluorine atom, and in a case of q=1, R 28 and R 29 , R 29 and R 30 , and R 30 and R 31 may be bonded to each other to form a monocyclic ring or a polycyclic ring and in a case of q=2 or 3, R 28 and R 28 , R 28 and R 29 , R 29 and R 30 , R 30 and R 31 , and R 31 and R 31 may be bonded to each other to form a monocyclic ring or a polycyclic ring, and the monocyclic ring or the polycyclic ring may be an aromatic ring,

wherein, in General Formula (V), R 100 and R 101 may be the same or different from each other and are each represent a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and f is 1≤f≤18, and

wherein, in General Formula (VI), q is 1, 2, or 3, R 32 to R 39 are each independently a hydrogen atom, a halogen atom excluding a fluorine atom, or a hydrocarbon group having 1 to 20 carbon atoms, which may be substituted with a halogen atom excluding a fluorine atom, and in a case of q=1, R 36 and R 37 , R 37 and R 38 , and R 38 and R 39 may be bonded to each other to form a monocyclic ring or a polycyclic ring and in a case of q=2 or 3, R 36 and R 36 , R 36 and R 37 , R 37 and R 38 , R 38 and R 39 , and R 39 and R 39 may be bonded to each other to form a monocyclic ring or a polycyclic ring, the monocyclic ring or the polycyclic ring may have a double bond, and the monocyclic ring or the polycyclic ring may be an aromatic ring.

7. The cyclic olefin-based resin composition according to claim 6 ,
wherein the repeating unit (b) derived from the cyclic olefin in the copolymer (A1) includes a repeating unit derived from at least one compound selected from bicyclo[2.2.1]-2-heptene, tetracyclo[4.4.0.1 2,5 .1 7,10 ]-3-dodecene, and benzonorbornadiene.

8. The cyclic olefin-based resin composition according to claim 6 ,
wherein the repeating unit (a) derived from the olefin in the copolymer (A1) includes a repeating

Assignees

• Mitsui Chemicals Inc

Inventors

• Kasuya Masakatsu
• Kizu Kouichi
• Soeda Yasuyuki
• Okuno Takayuki
• Kato Hisahiro
• Endo Keisuke

Classifications

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C08K5/353

  Five-membered rings · CPC title

• C08K5/3435 Primary

  Piperidines · CPC title

• C08F2500/32

  Glass transition temperature [Tg] · CPC title

• G02B3/00

  Simple or compound lenses · CPC title