MECHANOCHROMIC LUMINESCENT MATERIAL, MECHANOCHROMIC RESIN OBTAINED BY CROSSLINKING MECHANOCHROMIC LUMINESCENT MATERIAL, METHOD FOR PRODUCING MECHANOCHROMIC LUMINESCENT MATERIAL, AND METHOD FOR PRODUCING MECHANOCHROMIC

• US 20190031820A1
• Filed: 11/16/2015
• Published: 01/31/2019
• Est. Priority Date: 11/18/2014
• Status: Active Grant

• Current Assignee: Japan Science And Technology Agency
• Original Assignee: Japan Science And Technology Agency
• Inventors: YABU, Hiroshi, SAITO, Yuta, SAITO, Shohei, YAMAGUCHI, Shigehiro, NOBUSUE, Shunpei
• Granted Patent: US 10,442,886 B2
• Time in Patent Office: Days
• CPC Class Codes: C07D 209/70 containing carbocyclic rings other than six-membered
• CPC Class Codes: C08G 2261/122 statistical
• CPC Class Codes: C08G 2261/135 Cross-linked structures
• CPC Class Codes: C08G 2261/3324 derived from norbornene
• CPC Class Codes: C08G 2261/418 Ring opening metathesis polymerisation [ROMP]
• CPC Class Codes: C08G 2261/522 fluorescent
• CPC Class Codes: C08G 2261/62 Mechanical aspects
• CPC Class Codes: C08G 2261/76 crosslinking
• CPC Class Codes: C08G 61/08 of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials
• CPC Class Codes: G01L 1/24 by measuring variations of optical properties of material when it is stressed, e.g. by photoelastic stress analysis using infrared, visible light, ultraviolet

Abstract

Provided is a mechanochromic resin by which a stress applied to a material can be visualized in real time, and a mechanochromic luminescent material that is used in the synthesis of the mechanochromic resin. Stress can be visualized in real time by means of a mechanochromic luminescent material represented by formula (1) or formula (2) and a mechanochromic resin obtained by crosslinking the mechanochromic luminescent material. [Chemical formula 1] (In the formula, Y₁ and Y₂ each denote a substituent group that inhibits aggregation of the mechanochromic luminescent material represented by formula (1), and Y₁ and Y₂ may be same as or different from each other. Z₁ and Z₂ each denote a polymerizable group, and may be same as or different from each other.) [Chemical formula 2] (In the formula, Y₁ and Y₂ each denote a substituent group that inhibits aggregation of the mechanochromic luminescent material represented by formula (2), and Y₁ and Y₂ may be same as or different from each other. Z₁ and Z₂ each denote a polymerizable group, and may be same as or different from each other.)

Claims

1. A mechanochromic luminescent material represented by formula (1) or formula (2) below.

2. The mechanochromic luminescent material according to claim 1, wherein Y₁ and Y₂ are selected from the following substituents.

3. The mechanochromic luminescent material according to claim 2, wherein the polymerizable groups Z₁ and Z₂ are selected from the following substituents.

4. A mechanochromic resin in which the mechanochromic luminescent material according to claim 1is crosslinked to a polymer chain.

5. The mechanochromic resin according to claim 4, wherein the mechanochromic resin is in the form of a film or a fiber.

6. A tension sensor comprising the mechanochromic resin according to claim 5.

15. The mechanochromic luminescent material according to claim 1, wherein the polymerizable groups Z1 and Z2 are selected from the following substituents.

16. A mechanochromic resin in which the mechanochromic luminescent material according to claim 2 is crosslinked to a polymer chain.

17. A mechanochromic resin in which the mechanochromic luminescent material according to claim 3 is crosslinked to a polymer chain.

18. A mechanochromic resin in which the mechanochromic luminescent material according to claim 15 is crosslinked to a polymer chain.

7. A method for producing a mechanochromic luminescent material represented by formula (26) below,

comprising a step for reacting a compound represented by formula (16) below and a compound represented by formula (25) below.

8. The method for producing a mechanochromic luminescent material according to claim 7, wherein Y₁ and Y₂ are selected from the following substituents.

9. The method for producing a mechanochromic luminescent material according to claim 8, wherein the polymerizable groups Z₁ and Z₂ are selected from the following substituents.

10. The method for producing a mechanochromic luminescent material according to claim 7, wherein n is 0 or 1.

19. The method for producing a mechanochromic luminescent material according to claim 7, wherein the polymerizable groups Z1 and Z2 are selected from the following substituents.

11. A method for producing a mechanochromic resin comprising a step for mixing a mechanochromic luminescent material represented by formula (26) below, a polymerizable monomer, and a catalyst or initiator in an organic solvent.

12. The method for producing a mechanochromic resin according to claim 11, wherein Y₁ and Y₂ are selected from the following substituents.

13. The method for producing a mechanochromic resin according to claim 11, wherein the polymerizable groups Z₁ and Z₂ are selected from the following sub stituents.

14. The method for producing a mechanochromic resin according to claim 11, wherein n is 0 or 1.

20. The method for producing a mechanochromic resin according to claim 11, wherein the polymerizable groups Z1 and Z2 are selected from the following substituents.