Mechanochromic luminescent material, mechanochromic resin obtained by crosslinking mechanochromic luminescent material, method for producing mechanochromic luminescent material, and method for producing mechanochromic

• US 10,442,886 B2
• Filed: 11/16/2015
• Issued: 10/15/2019
• Est. Priority Date: 11/18/2014
• Status: Active Grant

• Current Assignee: Japan Science & Technology Trading Co. Limited
• Original Assignee: National Institute of Advanced Industrial Science and Technology (Government of Japan)
• Inventors: Yabu, Hiroshi, Saito, Yuta, Saito, Shohei, Yamaguchi, Shigehiro, Nobusue, Shunpei
• Primary Examiner(s): Lee, Rip A
• Application Number:
  US15/527,639
• Publication Number:
  US 20190031820A1
• Time in Patent Office: 1,429 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. A mechanochromic resin in which the mechanochromic luminescent material according to claim 1 is crosslinked to a polymer chain.

3. The mechanochromic resin according to claim 2, wherein the mechanochromic resin is in the form of a film or a fiber.

4. A tension sensor comprising the mechanochromic resin according to claim 3.

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

comprising a step of reacting a compound represented by formula (16) below and a compound represented by formula (25) below:

6. The method for producing a mechanochromic luminescent material according to claim 5, wherein n is 0 or 1.

7. A method for producing a mechanochromic resin comprising

a step of mixing a mechanochromic luminescent material represented by formula (26) below, a polymerizable monomer, and a catalyst or initiator in an organic solvent,

8. The method for producing a mechanochromic resin according to claim 7, wherein n is 0 or 1.