Photochromic polyrotaxane compound and curable composition comprising the photochromic polyrotaxane compound

Patent metadata

Field	Value
Publication number	US-11066523-B2
Application number	US-201816621634-A
Country	US
Kind code	B2
Filing date	Jun 18, 2018
Priority date	Jun 20, 2017
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

Abstract

A photochromic polyrotaxane compound which comprises an axial molecule and a plurality of cyclic molecules clathrating the axial molecule, wherein at least one side chain containing a photochromic moiety is bonded to at least one of the cyclic molecules, and a curable composition comprising the photochromic polyrotaxane compound and a polymerizable compound.

First claim

The invention claimed is:

1. A photochromic polyrotaxane compound which is a polyrotaxane compound comprising an axial molecule and a plurality of cyclic molecules clathrating the axial molecule, wherein a side chain containing a photochromic moiety is bonded to at least one of the cyclic molecules, and the cyclic molecules are cyclodextrin rings.

2. The photochromic polyrotaxane compound according to claim 1 , wherein a side chain containing a polymerizable group is bonded to at least one of the cyclic molecules.

3. The photochromic polyrotaxane compound according to claim 1 , wherein the side chain containing a photochromic moiety has at least an ether bond.

4. The photochromic polyrotaxane compound according to claim 2 , wherein the group containing a polymerizable group has at least an ether bond.

5. The photochromic polyrotaxane compound according to claim 1 , wherein the axial molecule includes a chain-like main chain and bulky groups at both ends, the chain-like main chain is formed from polyethylene glycol, and the bulky groups at both ends are adamantyl groups.

6. The photochromic polyrotaxane compound according to claim 1 , wherein the photochromic moiety has at least one structure selected from the group consisting of naphthopyran, spirooxazine, spiropyran, fulgide, fulgimide and diarylethene.

7. The photochromic polyrotaxane compound according claim 1 , wherein the photochromic moiety is indeno[2,1-f]naphtho[1,2-b]pyran.

8. The photochromic polyrotaxane compound according to claim 2 , wherein the polymerizable group is at least one group selected from the group consisting of acrylic group, methacrylic group, allyl group, vinyl group, 4-vinylphenyl group, epoxy group, episulfide group, thietanyl group, OH group, SH group, NH 2 group, NCO group and NCS group.

9. The photochromic polyrotaxane compound according to claim 1 , wherein the side chain containing a photochromic moiety is represented by the following formula (1):

wherein PC is a photochromic group, R 1 is a linear or branched alkylene group having 2 to 8 carbon atoms, R 2 is a linear or branched alkylene group having 2 to 8 carbon atoms, linear or branched alkylene group having an acetyl group branch and 3 to 8 carbon atoms, or linear or branched alkylene group having an ether bond and 3 to 8 carbon atoms, L is represented by the following formula (2):

wherein R 3 is a single bond, linear or branched alkylene group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, or aromatic group having 6 to 12 carbon atoms,
R 4 is a linear or branched alkylene group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, aromatic group having 6 to 12 carbon atoms, or dialkylsilyl group having a linear or branched alkyl group with 1 to 20 carbon atoms, le is a linear or branched alkylene group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, or aromatic group having 6 to 12 carbon atoms, X 1 and X 2 are each independently a single bond, O or NH,
“c” is an integer of 0 to 50, “d” is an integer of 0 to 50, “e” is an integer of 0 or 1, when “c” is 2 or more, a “c” number of divalent groups may be the same or different, and when “d” is 2 or more, a “d” number of divalent groups may be the same or different,
“a” is an integer of 1 to 50, “b” is an integer of 0 to 50, when “a” is 2 or more, an “a” number of divalent groups may be the same or different, and when “b” is 2 or more, a “b” number of divalent groups may be the same or different.

10. The photochromic polyrotaxane compound according to claim 2 , wherein the side chain containing a polymerizable group is represented by the following formula (3):

wherein Z is a polymerizable group, R 6 is a linear or branched alkylene group having 2 to 8 carbon atoms, R 7 is a linear or branched alkylene group having 2 to 8 carbon atoms, linear or branched alkylene group having an acetyl group branch and 3 to 8 carbon atoms, or linear or branched alkylene group having an ether bond and 3 to 8 carbon atoms, L′ is represented by the following formula (2′):

wherein R 31 is a single bond, linear or branched alkylene group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, or aromatic group having 6 to 12 carbon atoms,
R 41 is a linear or branched alkylene group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, aromatic group having 6 to 12 carbon atoms, or dialkylsilyl group having a linear or branched alkyl group with 1 to 20 carbon atoms, R 51 is a linear or branched alkylene group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, or aromatic group having 6 to 12 carbon atoms, X 11 and X 21 are each independently a single bond, O or NH,
“c 1 ” is an integer of 0 to 50, “d 1 ” is an integer of 0 to 50, “e 1 ” is an integer of 0 or 1, when “c 1 ” is 2 or more, a “c 1 ” number of divalent groups may be the same or different, and when “d 1 ” is 2 or more, a “d 1 ” number of divalent groups may be the same or different, “f” is an integer of 1 to 50,
“g” is an integer of 0 to 50, when “f” is 2 or more, an “f” number of divalent groups may be the same, and when “g” is 2 or more, a “g” number of divalent groups may be the same or different.

11. The photochromic polyrotaxane compound according to claim 1 , wherein the cyclic molecules are cyclodextrin rings, 1 to 100% of the side chains bonded to the cyclodextrin rings contain the photochromic moiety, and 0 to 99% of the side chains have the polymerizable group.

12. A curable composition comprising the photochromic polyrotaxane compound of claim 1 and a polymerizable compound other than the photochromic polyrotaxane compound.

13. The curable composition according to claim 12 , wherein the polymerizable compound other than the photochromic polyrotaxane compound is a compound having at least one radically polymerizable group selected from the group consisting of acrylic group, methacrylic group, allyl group, vinyl group and 4-vinylphenyl group.

14. The curable composition according to claim 12 , wherein the polymerizable compound other than the photochromic polyrotaxane compound is a compound having at least one polymerizable group selected from the group consisting of epoxy group, episulfide group and thietanyl group.

15. The curable composition according to claim 12 , wherein the polymerizable compound other than the photochromic polyrotaxane compound is a compound having at least one polymerizable group selected from the group consisting of OH group, SH group, NH 2 group, NCO group and NCS group.

16. A photochromic cured body obtained by curing the photochromic polyrotaxane compound of claim 2 .

17. A photochromic cured body obtained by curing the curable composition of claim 12 .

18. The photochromic polyrotaxane compound according to claim 3 , wherein the group containing a polymerizable group has at least an ether bond.

19. The photochromic polyrotaxane compound according to claim 2 , wherein the cyclic molecules are cyclodextrin rings.

Assignees

• Tokuyama Corp

Inventors

• Takenaka Junji
• Momoda Junji
• Kawasaki Takayoshi
• Noguchi Takao
• Shimizu Yasutomo
• Miyazaki Masayuki

Classifications

• C08G65/48

  Polymers modified by chemical after-treatment · CPC title

• C08G83/007 Primary

  Polyrotaxanes; Polycatenanes · CPC title

• C08F290/00

  Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups · CPC title

• C09K9/02 Primary

  Organic tenebrescent materials · CPC title

• G02B5/23

  Photochromic filters · CPC title