Azo compound or salt thereof, and dye-based polarizing film and dye-based polarizing plate containing same

Patent metadata

Field	Value
Publication number	US-12098287-B2
Application number	US-201917414571-A
Country	US
Kind code	B2
Filing date	Dec 17, 2019
Priority date	Dec 27, 2018
Publication date	Sep 24, 2024
Grant date	Sep 24, 2024

Abstract

An azo compound represented by the following formula (1) or a salt thereof, WhereinA1 represents a naphthyl group which may have a substituent;A2, A3, and A4 each independently represent a phenyl group which may have a substituent or a naphthyl group which may have a substituent;R1 represents a hydrogen atom, a hydroxy group, a C1-4 alkoxy group, or a substituted or unsubstituted amino group;m represents an integer of 0 to 5;M represents a hydrogen atom or ion, a metal ion, or an ammonium ion;n represents 1 or 2;k represents 0 or 1; andeach hydrogen atom on ring a and ring b may be substituted with the substituent R1 or substituent SO3M.

First claim

The invention claimed is:

1. An azo compound represented by the following formula (1) or a salt thereof:

wherein
A 1 represents a naphthyl group which may have a substituent;
A 2 , A 3 and A 4 are each independently represented by the following formula (2) or formula (3), and at least one of A 2 , A 3 and A 4 is represented by the formula (2):

wherein
R 2 represents a hydrogen atom, a hydroxy group, a C1-4 aliphatic hydrocarbon group, a C1-4 alkoxy group, a substituted or unsubstituted amino group, or a C1-4 alkoxy group having a sulfo group;
m 2 represents an integer of 0 to 6;
M represents a hydrogen atom or ion, a metal ion or an ammonium ion; and
n 3 represents an integer of 0 to 2, and

wherein
R 3 and R 4 each independently represent a hydrogen atom, a C1-4 aliphatic hydrocarbon group, a C1-4 alkoxy group, a C1-4 alkoxy group having a hydroxy group, or a C1-4 alkoxy group having a sulfo group;
R 1 represents a hydrogen atom, a hydroxy group, a C1-4 alkoxy group or a substituted or unsubstituted amino group;
m represents an integer of 0 to 5;
M represents a hydrogen atom or ion, a metal ion, or an ammonium ion;
n represents 1 or 2;
k represents 0 or 1; and
each hydrogen atom on ring a and ring b may be substituted with the substituent R 1 or substituent SO 3 M.

2. The azo compound or a salt thereof according to claim 1 , wherein A 1 in the above formula (1) represents a naphthyl group having one or more substituents selected from the group consisting of a hydroxy group, a C1-4 alkoxy group having a sulfo group, and a sulfo group.

3. The azo compound or a salt thereof according to claim 1 , wherein A 1 in the above formula (1) is represented by the following formula (4):

wherein n 4 represents 1 or 2.

4. The azo compound or a salt thereof according to claim 1 , wherein the above formula (1) is represented by the following formula (5):

wherein
A 1 , A 2 , A 3 , A 4 , M, n and k are each the same as those in the above formula (1); and
each hydrogen atom on ring a and ring b may be substituted with a substituent SO 3 M.

5. The azo compound or a salt thereof according to claim 1 , wherein the above formula (1) is represented by the following formula (6):

wherein
R 5 , R 6 and R 7 each independently represent a hydrogen atom, a hydroxy group, a C1-4 alkoxy group or a substituted or unsubstituted amino group;
m 3 to m 5 each independently represent an integer of 0 to 5;
M represents a hydrogen atom or ion, a metal ion or an ammonium ion;
n 5 and n 6 each independently represent 1 or 2; and
k 1 represents 0 or 1.

6. A polarizing film, comprising at least one azo compound or a salt thereof according to claim 1 .

7. The polarizing film according to claim 6 , wherein at least one of wavelengths at which an absorbance ratio Rd=A H /A L of an absorbance A H on an axis giving the lowest transmittance of polarized light to an absorbance A L on an axis giving the highest transmittance of the polarized light indicates a value of 5 or higher is in 700 to 1,500 nm.

8. The polarizing film according to claim 6 , further comprising one or more organic dyes other than the azo compound or the salt thereof.

9. The polarizing film according to claim 6 , wherein the polarizing film exhibits neutral gray.

10. The polarizing film according to claim 6 , using a film comprising a polyvinyl alcohol resin or a derivative thereof as a base material.

11. A polarizing plate, comprising a transparent protection layer on at least one surface of the polarizing film according to claim 6 .

12. A display, comprising a polarizing plate according to claim 11 .

13. A display, comprising a polarizing film according to claim 6 .

14. The display according to claim 13 , wherein the display is used for vehicular usage or outdoor display usage.

Assignees

• Nippon Kayaku Kk

Inventors

• Hattori yu
• Morita Ryoutarou
• Mochizuki Noriaki

Classifications

• G02B5/3025

  Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state (G02B5/3008, G02B5/3016 take precedence) · CPC title

• G02B1/08

  made of polarising materials · CPC title

• C09B31/30

  Other polyazo dyes · CPC title

• C09B31/18

  from a coupling component "D" containing a directive amine group · CPC title

• C09B31/22

  from a coupling component "D" containing directive hydroxyl and amino groups · CPC title