Triarylmethane compounds

Patent metadata

Field	Value
Publication number	US-11760712-B2
Application number	US-201916968106-A
Country	US
Kind code	B2
Filing date	Feb 1, 2019
Priority date	Feb 9, 2018
Publication date	Sep 19, 2023
Grant date	Sep 19, 2023

Abstract

The present invention relates to triarylmethane compounds of the formula (I), which suitable as monomers for preparing thermoplastic resins having beneficial optical properties and which can be used for producing optical devices. R 1 , R 2 are e.g. hydrogen; Y is an alkylene group having 2, 3 or 4 carbon atoms, Ar is selected from mono- or polycyclic aryl and mono- or polycyclic hetaryl; X 1 , X 2 , X 3 , X 4 are CH, C—R x or N, provided that in each ring at most two of X 1 , X 2 , X 3 , X 4 are N; R x is e.g. halogen, CN or CH═CH 2 . The invention also relates to thermoplastic resins comprising a polymerized unit of the compound of formula (I).

First claim

We claim:

1. A thermoplastic resin comprising a structural unit represented by formula (II) below

where
# represents a connection point to a neighboring structural unit;
R 1 , R 2 are hydrogen, a radical R a or R 1 and R 2 together with the carbon atoms to which they are bound may also form a fused benzene ring, which is unsubstituted or substituted by one radical R a ,
Y represents an alkylene group having 2, 3 or 4 carbon atoms,
Ar is selected from the group consisting of mono- or polycyclic aryl having from 6 to 26 carbon atoms and mono- or polycyclic hetaryl having a total of 5 to 26 atoms, which are ring members, where 1, 2, 3 or 4 of these atoms are selected from nitrogen, sulphur and oxygen, while the remainder of these atoms are carbon atoms, where mono- or polycyclic aryl and mono- or polycyclic hetaryl are unsubstituted or carry one, two, three or four radicals R Ar ;
X 1 , X 2 , X 3 , X 4 are CH, C—R x or N, provided that in each ring at most two of X 1 , X 2 , X 3 , X 4 are N;
R a is selected from the group consisting of fluorine, cyclopropyl, cyclobutyl, CN, R, OR, CH n R 3-n , NR 2 , C(O)R, C(O)NH 2 , CH═CH 2 , CH═CHR′, CH 2 —CH═CH 2 , CH 2 —CH═CHR′, CH 2 —C≡CH and CH 2 —C≡CR′;
R Ar is selected from the group consisting of fluorine, cyclopropyl, cyclobutyl, CN, R, OR, CH n R 3-n , NR 2 , C(O)R, C(O)NH 2 , CH═CH 2 , CH═CHR′, CH 2 —CH═CH 2 , CH 2 —CH═CHR′, CH 2 —C≡CH and CH 2 —C≡CR′, wherein each R Ar is identical or different if more than one R Ar is present on each ring;
R x is selected from the group consisting of halogen, cyclopropyl, cyclobutyl, CN, R, OR, CH n R 3-n , NR 2 , C(O)R, CH═CH 2 , CH═CHR′, CH 2 —CH═CH 2 , CH 2 —CH═CHR′, CH 2 —C≡CH and CH 2 —C≡CR′, wherein each R x is identical or different if more than one R x is present on each ring;
R is selected from methyl, mono- or polycyclic aryl having from 6 to 26 carbon atoms and mono- or polycyclic hetaryl having a total of 5 to 26 atoms, which are ring members, where 1, 2, 3 or 4 of the ring atoms of hetaryl are selected from nitrogen and oxygen, while the remainder of these atoms are carbon atoms, where mono- or polycyclic aryl are unsubstituted or substituted by one, two, three or four identical or different radicals R″;
R′ is selected from methyl, mono- or polycyclic aryl having from 6 to 26 carbon atoms and mono- or polycyclic hetaryl having a total of 5 to 26 atoms, which are ring members, where 1, 2, 3 or 4 of the ring atoms of hetaryl are selected from nitrogen and oxygen, while the remainder of these atoms are carbon atoms, where mono- or polycyclic aryl are unsubstituted or substituted by one, two, three or four identical or different radicals R″;
R″ is selected from fluorine, cyclopropyl, cyclobutyl, phenyl, CN, OCH 3 , CH 3 , N(CH 3 ) 2 , C(O)CH 3 , CH═CH 2 , CH═CHCH 3 , CH 2 —CH═CH 2 , CH 2 —CH═CH—CH 3 , CH 2 —C≡CH and CH 2 —C≡C—CH 3 ; and
n is each 0, 1, 2 or 3;
wherein the thermoplastic resin has a refractive index at 23° C. at a wavelength of 589 nm of 1.6439 or higher.

2. The thermoplastic resin of claim 1 , where the structural unit is connected to one of the structures represented by formulae (III-1) to (III-5) below,

where # represents a connection point to a neighboring structural unit.

3. The thermoplastic resin of claim 1 , which is selected from copolycarbonate resins, copolyestercarbonate resins and copolyester resins, where the thermoplastic resin in addition to structural units represented by formula (II) comprises a structural unit of the formula (V),
#—O—R z -A 3 -R z —O-#-  (V)

where
# represents a connection point to a neighboring structural unit;
A 3 is a polycyclic radical bearing at least two benzene rings, wherein the benzene rings may be connected by A′ and/or directly fused to each other and/or fused by a non-benzene carbocycle, where A 3 is unsubstituted or substituted by one, two or three radicals R aa , which are selected from the group consisting of halogen, C 1 -C 6 -alkyl, C 5 -C 6 -cycloalkyl and phenyl;
A′ is selected from the group consisting of a single bond, O, C═O, S, SO 2 , CH 2 , CH—Ar″, CHAr″ 2 , CH(CH 3 ), C(CH 3 ) 2 and a radical of the formula (A″)

where
Q′ represents a single bond, O, NH, C═O, CH 2 or CH═CH; and
R 10a , R 10b independently of each other are selected from the group consisting of hydrogen, fluorine, CN, R, OR, CH k R 3-k , NR 2 , C(O)R and C(O)NH 2 , where k is 0, 1, 2 or 3;

Ar″ is selected from the group consisting of mono- or polycyclic aryl having from 6 to 26 carbon atoms and mono- or polycyclic hetaryl having a total of 5 to 26 atoms, which are ring members, where 1, 2, 3 or 4 of these atoms are selected from nitrogen, sulphur and oxygen, while the remainder of these atoms are carbon atoms, where Ar” is unsubstituted or substituted by one, two or three radicals R ab , which are selected from the group consisting of halogen, phenyl and C 1 -C 4 -alkyl;
R z is a single bond, Alk 1 or O-Alk 2 - where O is bound to A 3 , and where Alk 1 is C 2 -C 4 -alkandiyl; and
Alk 2 is C 2 -C 4 -alkandiyl.

4. The thermoplastic resin of claim 3 , where the structural unit of the formula V is represented by one of the following formulae V-1 to V-8:

5. An optical device made of a thermoplastic resin as defined in claim 1 .

6. The optical device of claim 5 , wherein the optical device is an optical lens or an optical film.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Reuter Karl
• Andrushko Vasyl
• Kantor Mark
• Stolz Florian
• SHIRATAKE Munenori
• Ishihara Kentaro
• Hirose Koji
• Ikeda Shinya
• Kato Noriyuki
• Kondo Mitsuteru
• Murata Shoko
• Oshima Kensuke

Classifications

• C07C43/23 Primary

  containing hydroxy or O-metal groups · CPC title

• C07C43/202 Primary

  the aromatic ring being a naphthalene · CPC title

• C08G64/06

  not containing aliphatic unsaturation · CPC title

• C07C43/295

  containing hydroxy or O-metal groups · CPC title

• C07C255/00

  Carboxylic acid nitriles (cyanogen or compounds thereof C01C3/00) · CPC title