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

Patent metadata

Field	Value
Publication number	US-10442886-B2
Application number	US-201515527639-A
Country	US
Kind code	B2
Filing date	Nov 16, 2015
Priority date	Nov 18, 2014
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

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, Y 1 and Y 2 each denote a substituent group that inhibits aggregation of the mechanochromic luminescent material represented by formula (1), and Y 1 and Y 2 may be same as or different from each other. Z 1 and Z 2 each denote a polymerizable group, and may be same as or different from each other.) [Chemical formula 2] (In the formula, Y 1 and Y 2 each denote a substituent group that inhibits aggregation of the mechanochromic luminescent material represented by formula (2), and Y 1 and Y 2 may be same as or different from each other. Z 1 and Z 2 each denote a polymerizable group, and may be same as or different from each other).

First claim

What is claimed is:

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

in the formula, Y 1 and Y 2 represent substituents that inhibit aggregation of a mechanochromic luminescent material represented by formula (1), and may be the same or different, Z 1 and Z 2 represent polymerizable groups, and may be the same or different,

in the formula, Y 1 and Y 2 represent substituents that inhibit aggregation of a mechanochromic luminescent material represented by formula (2), and may be the same or different, Z 1 and Z 2 represent polymerizable groups, and may be the same or different,
wherein Y 1 and Y 2 are selected from the following substituents: represented by Chemical formula 3

any one of the substituents R 1 -R 7 represents a polymerizable group Z 1 or Z 2 ; R 1 -R 7 other than the polymerizable group Z 1 or Z 2 represent H, a C1-20 linear, branched, or cyclic alkyl group, C6-20 aryl group, F, Cl, Br, I, CF 3 , CCl 3 , or OCH 3 ; and R 1 -R 7 other than the polymerizable group Z 1 or Z 2 may be the same or different,
wherein the polymerizable groups Z 1 and Z 2 are selected from the following substituents:

in the above formulas (3) and (4), X represents an amide or ester, but may be absent; in the above formulas (3) and (4), R 1 is the same as R 1 in [Chemical formula 3]; in the above formulas (3) to (13), R represents a C1-20 linear, branched, or cyclic alkylene group or a C6-20 arylene group, but R may be absent; and ● represents Y 1 or Y 2 , and
wherein when:

is selected as Z 1 and Z 2 , R is absent, X is absent, and R 1 is H, and

is selected as Y 1 and Y 2 , and R 2 is Z 1 and Z 2 ,
R 1 and R 3 are selected from C1-20 linear, branched, or cyclic alkyl group, C6-20 aryl group, F, Cl, Br, I, CF 3 , CCl 3 , or OCH 3 .

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:

in the formula, Y 1 and Y 2 represent substituents that inhibit aggregation of a mechanochromic luminescent material represented by formula (26), and may be the same or different, Z 1 and Z 2 represent polymerizable groups, and may be the same or different, n represents an integer of 0-3,

in the formula, Y is the same as Y 1 or Y 2 ; and Z is the same as Z 1 or Z 2 ,

in the formula, n represents an integer of 0-3,
wherein Y 1 and Y 2 are selected from the following substituents: represented by Chemical formula 3

any one of the substituents R 1 -R 7 represents a polymerizable group Z 1 or Z 2 ; R 1 -R 7 other than the polymerizable group Z 1 or Z 2 represent H, a C1-20 linear, branched, or cyclic alkyl group, C6-20 aryl group, F, Cl, Br, I, CF 3 , CCl 3 , or OCH 3 ; and R 1 -R 7 other than the polymerizable group Z 1 or Z 2 may be the same or different,
wherein the polymerizable groups Z 1 and Z 2 are selected from the following substituents:

in the above formulas (3) and (4), X represents an amide or ester, but may be absent; in the above formulas (3) and (4), R 1 is the same as R 1 in [Chemical formula 3]; in the above formulas (3) to (13), R represents a C1-20 linear, branched, or cyclic alkylene group or a C6-20 arylene group, but R may be absent; and ● represents Y 1 or Y 2 , and
wherein when:

is selected as Z 1 and Z 2 , R is absent, X is absent, and R 1 is H, and

is selected as Y 1 and Y 2 , and R 2 is Z 1 and Z 2 ,
R 1 and R 3 are selected from C1-20 linear, branched, or cyclic alkyl group, C6-20 aryl group, F, Cl, Br, I, CF 3 , CCl 3 , or OCH 3 .

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,

in the formula, Y 1 and Y 2 represent substituents that inhibit aggregation of a mechanochromic luminescent material represented by formula (26), and may be the same or different, Z 1 and Z 2 represent polymerizable groups, and may be the same or different, n represents an integer of 0-3,
wherein Y 1 and Y 2 are selected from the following substituents: represented by Chemical formula 3

any one of the substituents R 1 -R 7 represents a polymerizable group Z 1 or Z 2 ; R 1 -R 7 other than the polymerizable group Z 1 or Z 2 represent H, a C1-20 linear, branched, or cyclic alkyl group, C6-20 aryl group, F, Cl, Br, I, CF 3 , CCl 3 , or OCH 3 ; and R 1 -R 7 other than the polymerizable group Z 1 or Z 2 may be the same or different,
wherein the polymerizable groups Z 1 and Z 2 are selected from the following substituents:

in the above formulas (3) and (4), X represents an amide or ester, but may be absent; in the above formulas (3) and (4), R 1 is the same as R 1 in [Chemical formula 3]; in the above formulas (3) to (13), R represents a C1-20 linear, branched, or cyclic alkylene group or a C6-20 arylene group, but R may be absent; and ● represents Y 1 or Y 2 , and
wherein when:

is selected as Z 1 and Z 2 , R is absen

Assignees

• Japan Science & Tech Agency

Inventors

• Yabu Hiroshi
• Saito Yuta
• Saito Shohei
• Yamaguchi Shigehiro
• NOBUSUE Shunpei

Classifications

• C08G2261/522

  fluorescent · CPC title

• C07D209/70

  containing carbocyclic rings other than six-membered · CPC title

• C08G2261/62

  Mechanical aspects · CPC title

• C08G2261/122

  statistical · CPC title

• C08G2261/76

  crosslinking · CPC title