Polyrotaxane, Production Method Therefor, and Optical Composition Containing said Polyrotaxane

Patent metadata

Field	Value
Publication number	US-2018312643-A1
Application number	US-201615757062-A
Country	US
Kind code	A1
Filing date	Aug 31, 2016
Priority date	Sep 3, 2015
Publication date	Nov 1, 2018
Grant date	—

Abstract

The present invention provides an optical composition from which an optical article having reduced poor appearance such as cloudiness and optical strain during lens base material production can be obtained, and when a photochromic compound is added, a photochromic cured body having excellent photochromism and mechanical strength can also be formed, and a polyrotaxane used therefor. The polyrotaxane has a composite molecular structure formed of an axle molecule and a plurality of cyclic molecules clathrating the axle molecule, satisfying at least one of (X) and (Y). (X): A side chain having a secondary or tertiary hydroxyl group is introduced into at least part of the cyclic molecule of the polyrotaxane. (Y): A side chain having a group represented by -A (A is an organic group, and contains at least one hydroxyl group) is introduced into at least part of the cyclic molecule of the polyrotaxane, and a pKa of the hydroxyl group of the compound represented by H-A is 6 or more and less than 14.

First claim

1 . A polyrotaxane, comprising a composite molecular structure formed of an axle molecule and a plurality of cyclic molecules clathrating the axle molecule, wherein the polyrotaxane satisfies at least one of requirements (X) and (Y):
requirement (X): a side chain having a secondary or tertiary hydroxyl group is introduced into at least part of the cyclic molecule of the polyrotaxane; and requirement (Y): a side chain having a group represented by the following formula (1):
-A  (1)

(wherein, A is an organic group having 1 to 10 carbon atoms and contains at least one hydroxyl group) is introduced into at least part of the cyclic molecule of the polyrotaxane; and a pKa of a hydroxyl group of a compound represented by the following formula (2):
H-A  (2)

is 6 or more and less than 14.

2 . The polyrotaxane according to claim 1 , satisfying the requirement (X).

3 . The polyrotaxane according to claim 2 , wherein a proportion of a primary hydroxyl group is 50% or less, when the total mole number of primary, secondary and tertiary hydroxyl groups of the side chain is taken as 100%.

4 . The polyrotaxane according to claim 2 , wherein the side chain having the secondary or tertiary hydroxyl group comprises a structure represented by the following formula (1):

[wherein, Q is formed of at least one kind selected from structures represented by the following formulas (Q-1), (Q-2) and (Q-3):

(wherein, G is a straight-chain alkylene group or alkenylene group having 1 to 8 carbon atoms; a branched-chain alkylene group or alkenylene group having 3 to 20 carbon atoms; an alkylene group or alkenylene group formed by replacement of a part of the alkylene group or alkenylene group by a —O— bond, a —NH— bond, a —SO— bond or a —SiO— bond; or an alkylene group formed by replacement of a part of hydrogen of the alkylene group by at least one kind selected from the group consisting of a hydroxyl group, a carboxyl group, an acyl group, a phenyl group, a halogen atom and an olefin group, and when a plurality of G exist, each G may be a same group or a different group, and n 1 , n 2 and n 3 are each independently an integer from 1 to 200), and
when Q is formed of two or more kinds selected from the formulas (Q-1), (Q-2) and (Q-3), G constituting (Q-1) to (Q-3) may be a same group or a different group, a total of n 1 , n 2 and n 3 is an integer from 1 to 200, R 1 and R 2 are each independently a group selected from hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms and a branched-chain alkyl group having 1 to 6 carbon atoms, excluding a group in which R 1 and R 2 are simultaneously hydrogen].

5 . The polyrotaxane according to claim 2 , wherein the side chain having the secondary or tertiary hydroxyl group comprises a structure represented by the following formula (1′):

[wherein, Q is formed of at least one kind selected from structures represented by the following formulas (Q-1), (Q-2) and (Q-3):

(wherein, G is a straight-chain alkylene group or alkenylene group having 1 to 8 carbon atoms; a branched-chain alkylene group or alkenylene group having 3 to 20 carbon atoms; an alkylene group or alkenylene group formed by replacement a part of the alkylene group or alkenylene group by a —O— bond, a —NH— bond, a —SO— bond or a —SiO— bond; or an alkylene group formed by replacement of a part of hydrogen of the alkylene group by at least one kind selected from the group consisting of a hydroxyl group, a carboxyl group, an acyl group, a phenyl group, a halogen atom and an olefin group, and when a plurality of G exist, each G may be a same group or a different group, and n 1 , n 2 , n 3 are each independently an integer from 1 to 200), and
when Q is formed of two or more kinds selected from the formulas (Q-1), (Q-2) and (Q-3), G constituting (Q-1) to (Q-3) may be a same group or a different group, a total of n 1 , n 2 and n 3 is an integer from 1 to 200, X is an alkylene group or alkenylene group having 2 to 20 carbons, or an alkylene group or alkenylene group formed by replacement of a part of the alkylene group or alkenylene group by a —O— bond or a —NH— bond; R 3 and R 4 are each independently selected from hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms or a branched-chain alkyl group having 1 to 6 carbon atoms, excluding a group in which R 3 and R 4 are simultaneously hydrogen; and R 5 is carbon or sulfur].

6 . The polyrotaxane according to claim 1 , satisfying the requirement (Y).

7 . The polyrotaxane according to claim 6 , wherein a proportion of a hydroxyl group having a pKa of less than 6 or 14 or more is 50% or less, when the total mole number of the hydroxyl groups of the side chain is taken as 100%.

8 . The polyrotaxane according to claim 6 , wherein a side chain represented by the following formula (3) is introduced into at least part of the cyclic molecule:
-Q-A  (3)
[wherein, Q is formed of at least one kind selected from structures represented by the following formulas (Q-1), (Q-2) and (Q-3):

(wherein, G is a straight-chain alkylene group or alkenylene group having 1 to 8 carbon atoms; a branched-chain alkylene group or alkenylene group having 3 to 20 carbon atoms; an alkylene group or alkenylene group formed by replacement of a part of the alkylene group or alkenylene group by a —O— bond, a —NH— bond, a —SO— bond or a —SiO— bond, or an alkylene group formed by replacement of a part of hydrogen of the alkylene group by at least one kind selected from the group consisting of a carboxyl group, an acyl group, a phenyl group, a halogen atom and an olefin group, and when a plurality of G exist, each G may be a same group or a different group, and n 1 , n 2 and n 3 are each independently an integer from 1 to 200), and
when Q is formed of two or more kinds selected from the formulas (Q-1), (Q-2) and (Q-3), G constituting (Q-1) to (Q-3) may be a same group or a different group, a total of n 1 , n 2 and n 3 is an integer from 1 to 200, and A is an organic group having 1 to 10 carbon atoms, and contains at least one hydroxyl group].

9 . The polyrotaxane according to claim 6 , wherein a side chain represented by the following formula (3′) is introduced into at least part of the cyclic molecule:

[wherein, Q is formed of at least one kind selected from structures represented by the following formulas (Q-1), (Q-2) and (Q-3):

(wherein, G is a straight-chain alkylene group or alkenylene group having 1 to 8 carbon atoms; a branched-chain alkylene group or alkenylene group having 3 to 20 carbon atoms; an alkylene group or alkenylene group formed by replacement of a part of the alkylene group or alkenylene group by a —O— bond, a —NH— bond, a —SO— bond or a —SiO— bond; or an alkylene group formed by replacement of a part of hydrogen of the alkylene group by at least one kind selected from the group consisting of a carboxyl group, an acyl group, a phenyl group, a halogen atom and an olefin group, and when a plurality of G exist, e

Assignees

• Tokuyama Corp

Inventors

• Shimizu Yasutomo
• Mori Katsuhiro
• Momoda Junji
• Yamamoto Hiromasa

Classifications

• C08G18/3876

  containing mercapto groups · CPC title

• C08G18/757 Primary

  containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group · CPC title

• C08G18/4018

  Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48 · CPC title

• C08K5/0041

  Optical brightening agents, organic pigments · CPC title

• C08G18/288

  Compounds containing at least one heteroatom other than oxygen or nitrogen · CPC title