Thermoplastic resin, method for manufacturing same, and optical lens

Patent metadata

Field	Value
Publication number	US-12516153-B2
Application number	US-202017434258-A
Country	US
Kind code	B2
Filing date	Feb 27, 2020
Priority date	Feb 27, 2019
Publication date	Jan 6, 2026
Grant date	Jan 6, 2026

Abstract

Provided is a thermoplastic resin including constituent units represented by general formula (1). (In formula (1), R1 and R2 each independently represent: a hydrogen atom; a fluorine atom; a chlorine atom; a bromine atom; an iodine atom; a C1-6 alkyl group; a monocyclic or polycyclic C6-36 aryl group; a monocyclic or polycyclic heteroaryl group having 5-36 ring atoms, 1, 2, 3, or 4 of the ring atoms being selected from nitrogen, sulfur, and oxygen, and the other ring atoms being carbon in the heteroaryl group; a C2-6 alkenyl group; a C1-6 alkoxy group; or a C7-17 aralkyl group. In formula (1), X, a, and bare each as described in the present specification.)

First claim

The invention claimed is:

1 . A thermoplastic resin comprising a structural unit represented by general formula (1):

wherein:
R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 6 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 36 carbon atoms, a monocyclic or polycyclic heteroaryl group having 5 to 36 ring atoms where 1, 2, 3 or 4 of the ring atoms are selected from nitrogen, sulfur and oxygen while the other ring atoms are carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or an aralkyl group having 7 to 17 carbon atoms;
the monocyclic or polycyclic aryl group and the monocyclic or polycyclic heteroaryl group may be unsubstituted or have 1 or 2 R a groups selected from the group consisting of CN, CH 3 , OCH 3 , O-phenyl, O-naphthyl, S-phenyl, S-naphthyl and halogen;
with the proviso that both of R 1 and R 2 are not hydrogen;
X represents an alkylene group having 1 to 8 carbon atoms, a cycloalkylene group having 5 to 12 carbon atoms or an arylene group having 6 to 20 carbon atoms;
with the proviso that each of the alkylene group and the cycloalkylene group may be substituted to have a benzene ring; and
a and b each independently represent an integer of 1 to 10,
wherein the thermoplastic resin further comprises a structural unit represented by general formula (2):

wherein Q is represented by the formula below:

wherein R C s each independently represent a single bond that bonds to a CO group in formula (2) or an alkylene group, which may have a substituent, wherein the total carbon number is 1 to 10, and which includes a point of bonding to the CO group in formula (2) at the end,
wherein the thermoplastic resin has a refractive index of higher than 1.660 and Abbe number of 18 or less than 18, and
wherein the thermoplastic resin further comprises a polycarbonate structural unit.

2 . The thermoplastic resin according to claim 1 , which is a polyester carbonate resin.

3 . The thermoplastic resin according to claim 1 , which further comprises at least one additional structural unit represented by the general formula (2-1):

wherein Q′ is represented by formula (2a):

wherein in formula (2a), R c s each independently represent a single bond that bonds to a CO group in formula (2-1) or an alkylene group, which may have a substituent, wherein the total carbon number is 1 to 10, and which includes a point of bonding to the CO group in formula (2-1) at the end.

4 . The thermoplastic resin according to claim 1 , which comprises the structural unit represented by general formula (1) in an amount of more than 50 mol %, based on the structural units of the thermoplastic resin.

5 . The thermoplastic resin according to claim 1 , wherein at least one of R1 and R2 in general formula (1) is an aryl group having 6 to 20 carbon atoms.

6 . The thermoplastic resin according to claim 1 , wherein the structural unit represented by general formula (1) comprises at least one of structural units represented by general formulae (A-1) to (A-7):

7 . The thermoplastic resin according to claim 1 , which further comprises at least one of structural units represented by general formulae (3) and (4):

wherein:
R′ 1 to R′ 20 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or an aralkyl group having 7 to 17 carbon atoms;
Y represents an alkylene group having 1 to 8 carbon atoms, a cycloalkylene group having 5 to 12 carbon atoms or an arylene group having 6 to 20 carbon atoms; and
c and d each independently represent an integer of 1 to 10,

wherein:
R″ 1 to R″ 16 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or an aralkyl group having 7 to 17 carbon atoms;
Z represents an alkylene group having 1 to 8 carbon atoms, a cycloalkylene group having 5 to 12 carbon atoms or an arylene group having 6 to 20 carbon atoms; and
e and f each independently represent an integer of 1 to 10.

8 . The thermoplastic resin according to claim 7 , which comprises a copolymer comprising at least the structural unit represented by general formula (1) and the structural unit represented by general formula (3).

9 . The thermoplastic resin according to claim 7 , which comprises a copolymer comprising at least the structural unit represented by general formula (1) and the structural unit represented by general formula (4).

10 . The thermoplastic resin according to claim 1 , which further comprises at least one of structural units represented by general formula (5):

11 . The thermoplastic resin according to claim 1 , wherein the aryl group is selected from among a pyrenyl group, a furanyl group, a benzodioxanyl group, a dihydrobenzofuranyl group, a piperonyl group, a benzofuranyl group, a dibenzofuranyl group, a pyrrolidinyl group, an isoquinolyl group, a pyrimidinyl group and a carbazole group, which may be substituted with an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or an aryl group having 6 to 16 carbon atoms.

12 . The thermoplastic resin according to claim 1 , which has a refractive index of 1.668 or higher.

13 . The thermoplastic resin according to claim 1 , wherein said X is an ethylene group.

14 . The thermoplastic resin according to claim 1 , wherein the b value in accordance with JIS K 7105 is 10 or less.

15 . An optical lens containing the thermoplastic resin according to claim 1 .

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Ikeda Shinya
• Kato Noriyuki
• Hirakawa Manabu
• Reuter Karl
• Andrushko Vasyl
• Kantor Mark
• Stolz Florian

Classifications

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07C43/202

  the aromatic ring being a naphthalene · CPC title

• G02B1/041

  Lenses · CPC title

• C08G63/78

  Preparation processes · CPC title

• C08G63/66

  Polyesters containing oxygen in the form of ether groups (C08G63/42, C08G63/58 take precedence) · CPC title