Diester of bisphenol fluorene compounds and thermochromic pigment compositions comprising the same

Patent metadata

Field	Value
Publication number	US-11814528-B2
Application number	US-201917278457-A
Country	US
Kind code	B2
Filing date	Sep 20, 2019
Priority date	Sep 24, 2018
Publication date	Nov 14, 2023
Grant date	Nov 14, 2023

Abstract

There is a compound represented by the following formula (I):

in which R1 and R2, identical or different, represent a C 2 -C 30 alkyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, or a C 2 -C 30 alkoxy group, the alkyl, alkenyl, alkynyl, or alkoxy groups being optionally substituted with at least one hydroxy, halogen, amino, C 1 -C 8 alkyl, or C 1 -C 8 alkoxy group, as a temperature change regulating agent in a thermochromic ink composition. There also are thermochromic pigment microcapsules having a compound of formula (I) according to the disclosure, to ink compositions having such thermochromic pigment microcapsules, and to writing instruments comprising such ink compositions.

First claim

The invention claimed is:

1. Method of regulating temperature change in a thermochromic ink composition, comprising incorporating into the composition a compound represented by the following formula (I):

wherein R1 and R2, identical or different, represent a C 2 -C 30 alkyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, or a C 2 -C 30 alkoxy group, wherein the groups are optionally substituted with at least one hydroxy, halogen, amino, C 1 -C 8 alkyl, or C 1 -C 8 alkoxy group.

2. The method according to claim 1 , wherein R1 and R2 are identical and represent a linear or branched C 2 -C 30 alkyl group.

3. The method according to claim 1 wherein R1 and R2 are identical and represent a linear or branched C 6 -C 30 alkyl group.

4. A thermochromic pigment composition comprising:
(A) an electron-donating color-developing organic compound,
(B) an electron-accepting compound, and
(C) a compound represented by the formula (I) according to claim 1 as a reaction medium which controls color reaction between said components (A) and (B).

5. The thermochromic pigment composition according to claim 4 , wherein the compound (A) is selected from the group consisting of
3-(4-diethylamino-2-ethoxyphenyl)-3-(1-ethyl-2-methylindol-3-yl)-4-azaphthalide (Blue 63, CAS number: 69898-40-4),
2′-(dibenzylamino)-6′-(diethylamino)fluoran (CAS number: 34372-72-0),
N,N-dimethyl-4[2-[2-(octyloxy)phenyl]-6-phenyl-4-pyridinyl]benzenamine (Yellow CK37, CAS number: 144190-25-0),
7-(4-diethylamino-2-hexyloxyphenyl)-7-(1-ethyl-2-methyl-1H-indol-3-yl)-7H-furo[3,4-b]pyridin-5-one (Blue 203, CAS number: 98660-18-5),
2-(2,4-dimethylphenylamino)-3-methyl-6-diethylaminofluoran (Black 15, CAS number: 36431-22-8),
3,3-bis-(1-butyl-2-methyl-indol-3-yl)-3H-isobenzofuran-1-one (Red 40, CAS number: 50292-91-6),
and mixtures thereof.

6. The thermochromic pigment composition according to claim 4 , wherein the compound (B) is selected from the group consisting of
2,2-bis(4-hydroxy-3-methylphenyl)propane (bisphenol C, CAS number: 79-97-0),
4-hexyl-1,3-dihydroxybenzene (4-hexylresorcinol, CAS number: 136-77-6),
4,4′-cyclohexylidenebisphenol (BPZ, CAS number: 843-55-0),
4,4′-(hexafluoroisopropylidene)diphenol (bisphenol AF, CAS number: 1478-61-1),
4,4′-(1-phenylethylidene)bisphenol (CAS number: 1571-75-1),
2,2′-dihydroxybiphenyl (CAS number: 1806-29-7),
4,4′-(1,4-phenylenediisopropylidene)bisphenol (CAS number: 2167-51-3),
1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane (CAS number: 2362-14-3), 9,9-bis(4-hydroxyphenyl)fluorene (CAS number: 3236-71-3),
4,4′-(1,3-phenylenediisopropylidene)bisphenol (CAS number: 13595-25-0),
1,1,1-tris(4-hydroxyphenyl)ethane (CAS number: 27955-94-8),
4,4′-(2-ethylhexylidene)diphenol (CAS number: 74462-02-5),
α,α,α′-tris(4-hydroxyphenyl)-1-ethyl-4-isopropylbenzene (CAS number: 110726-28-8),
and mixtures thereof.

7. A thermochromic pigment microcapsule encapsulating a thermochromic pigment composition according to claim 4 .

8. A thermochromic ink composition comprising thermochromic pigment microcapsules according to claim 7 , and a carrier.

9. The thermochromic ink composition according to claim 8 , wherein the thermochromic pigment microcapsules are present in an amount of 5 to 40% by weight relative to the total weight of the thermochromic ink composition.

10. A writing instrument comprising:
an axial barrel containing a thermochromic ink composition according to claim 8 , and
a pen body which delivers the thermochromic ink composition stored in the axial barrel.

11. The writing instrument according to claim 10 , further comprising a friction member.

12. A writing instrument according to claim 10 , selected from the group consisting of ballpoint pens, brush pens, colored pencils, highlighters, chalks and felt pens.

13. The thermochromic pigment composition according to claim 4 , wherein R1 and R2 are identical and represent a linear or branched C 2 -C 30 alkyl group.

14. The thermochromic pigment composition according to claim 4 , wherein R1 and R2 are identical and represent a linear or branched C 4 -C 20 alkyl group.

15. The thermochromic pigment composition according to claim 4 , wherein R1 and R2 are identical and represent a linear or branched C 6 -C 30 alkyl group.

16. A writing instrument according to claim 15 , wherein the writing instrument is ballpoint pens erasable by friction.

17. A compound represented by the following formula (II) according to claim 16 , wherein R1a and R2b, identical or different, represent a linear or branched C 6 -C 18 alkyl group.

18. A compound represented by the following formula (II) according to claim 16 , wherein R1a and R2b, identical or different, represent a linear C 13 alkyl group.

19. The thermochromic pigment composition according to claim 4 , wherein R1 and R2 are identical and represent a linear or branched C 6 -C 18 alkyl group.

20. A compound represented by the following formula (II):

wherein R1a and R2b, identical or different, represent a linear or branched C 6 -C 30 alkyl group.

Assignees

• SOCIéTé BIC

Inventors

• Bourque Alexander

Classifications

• C09D11/50 Primary

  Sympathetic, colour changing or similar inks · CPC title

• B43K7/00

  Ball-point pens ({B43M11/085 takes precedence}; multiple-point writing implements B43K27/00) · CPC title

• B43K29/02

  with rubbers · CPC title

• C07C69/28

  esterified with dihydroxylic compounds · CPC title

• C09B5/00

  Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings · CPC title