Thermochromic pigment compositions

Patent metadata

Field	Value
Publication number	US-12043596-B2
Application number	US-201816608452-A
Country	US
Kind code	B2
Filing date	Apr 24, 2018
Priority date	Apr 27, 2017
Publication date	Jul 23, 2024
Grant date	Jul 23, 2024

Abstract

A thermochromic pigment composition including compounds of formula (I):in which: X represents CHR2, O, OCO or CH═CH; Y represents O, COO, or OCOO; R1 represents H or (CH2)pCH3; R2 represents phenyl or H; m=12-18; n=0-14; p=12-18; and on the condition that, if n=0, X represents CHR2 or CH═CH.The thermochromic pigment compositions having compounds of formula (I), include thermochromic pigment microcapsules. The thermochromic pigment capsules are useable for thermochromic pigment compositions in ink which may be used writing instruments.

First claim

The invention claimed is:

1. A thermochromic pigment composition, comprising:
(A) at least one organic electron-donating dye compound,
(B) at least one electron-accepting compound, and
at least one compound of formula (I):

in which:
X represents CHR 2 , O, OCO, or CH═CH,
Y represents O or COO,
R 1 represents H or (CH 2 ) p CH 3 ,
R 2 represents a phenyl group or H,
m=12-18,
n=0-14,
p=12-18, and

on the condition that, if n=0, X represents CHR 2 or CH═CH.

2. The thermochromic pigment composition according to claim 1 , corresponding to the following formula (I a ):

in which:
m=12-18, and
n=1-14.

3. The thermochromic pigment composition according to claim 1 , corresponding to the following formula (I b ):

in which:
m=12-18, and
n=0-14.

4. The thermochromic pigment composition according to claim 1 , corresponding to the following formula (I c ):

in which:
X represents CH 2 , or O,
Y represents O or COO,
m=12-18, and
n=1-14.

5. The thermochromic pigment composition according to claim 1 , wherein the at least one compound of formula (I) is selected from the group consisting of

6. The thermochromic pigment composition according to claim 1 , wherein 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 no.: 69898-40-4), 2′-(dibenzylamino)-6′-(diethylamino)fluorane (CAS no.: 34372-72-0), N,N-dimethyl-4-[2-[2-(octyloxy)phenyl]-6-phenyl-4-pyridinyl]benzenamine (Yellow CK37, CAS no.: 144190-25-0), 7-(4-diethylamino-2-hexyloxyphenyl)-7-(1-ethyl-2-methyl-1H-indol-3-yl)-7H-furo[3,4-b]pyridine-5-one (Blue 203, CAS no.: 98660-18-5), 2-(2,4-dimethylphenylamino)-3-methyl-6-diethylaminofluoran (Black 15, CAS no.: 36431-22-8), and 3,3-bis-(1-butyl-2-methyl-indol-3-yl)-3H-isobenzofuran-1-one (Red 40, CAS no.: 50292-91-6).

7. The thermochromic pigment composition according to claim 1 , wherein compound (B) is selected from the group consisting of 2,2-bis (4-hydroxy-3-methylphenyl)propane (Bisphenol C, CAS no.: 79-97-0), 4-hexyl-1,3-dihydroxybenzene (4-hexylresorcinol, CAS no.: 136-77-6), 4,4′-cyclohexylidenebisphenol (BPZ, CAS no.: 843-55-0), 4,4′-(hexafluoroisopropylidene)diphenol (Bisphenol AF, CAS no.: 1478-61-1), 4,4′-(1-phenylethylidene)bisphenol (CAS no.: 1571-75-1), 2,2′-dihydroxybiphenyl (CAS no.: 1806-29-7), 4,4′-(1,4-phenylenediisopropylidene)bisphenol (CAS no.: 2167-51-3), 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane (CAS no.: 2362-14-3), 9,9-bis(4-hydroxyphenyl)fluorene (CAS no.: 3236-71-3), 4,4′-(1,3-phenylenediisopropylidene)bisphenol (CAS no.: 13595-25-0), 1,1,1-tris(4-hydroxyphenyl)ethane (CAS no.: 27955-94-8), 4,4′-(2-ethylhexylidene)diphenol (CAS no.: 74462-02-5), α,α,α′-tris(4-hydroxyphenyl)-1-ethyl-4-isopropylbenzene (CAS no.: 110726-28-8).

8. A thermochromic pigment microcapsule comprising a composition according to 1 .

9. An ink composition comprising a thermochromic pigment microcapsules according to claim 8 .

10. A writing instrument comprising an ink composition according to claim 9 .

11. The writing instrument according to claim 10 , wherein the ink is erasable and the writing instrument is a ballpoint pen with an eraser.

12. A compound selected from the group consisting of

Assignees

• SOCIéTé BIC

Inventors

• Debrauwer Christelle
• Damiano Anne-Lise
• Bourque Alexander
• Foulonneau Francois
• Chollet Guillaume

Classifications

• C09D11/50

  Sympathetic, colour changing or similar inks · CPC title

• C09D11/18

  specially adapted for ball-point writing instruments · CPC title

• C09D11/17

  characterised by colouring agents · CPC title

• C07C69/34

  Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom · CPC title

• C07C43/205

  the aromatic ring being a non-condensed ring · CPC title