Compound for use in colour change compositions
Novel reaction media for electron donating and electron accepting components in colour-change compositions are described. The compound is of formula (VI); R 1 , and R 2 are independently selected from an optionally substituted linear or branched alkyl group, alkenyl group, alkoxy group, aryl group and an alkylene aryl group having from 5 to 22 carbon atoms; X 1 and X 2 are independently selected from —OC(O)—, —CO 2 — and O; Y 1 , and Y 2 are independently selected from hydrogen, halogen, R 1 , —OR 1 ; y is independently 0 or 1; and suitably the groups R 1 X 1 — and —X 2 R 2 are independently in the ortho or meta position. The compounds are useful in ink compositions, writing implements containing the compound and medical and industrial applications in which temperature sensitive colour change may be required.
1. A compound of formula:
wherein R 1 , and R 2 are independently selected from an optionally substituted linear alkyl group, alkenyl group, and an alkylene aryl group having from 12 to 22 carbon atoms and an aryl group;
X 1 and X 2 are independently selected from —OC(O)— and —CO 2 —;
Y 1 , and Y 2 are independently selected from hydrogen, halogen, R 3 , and —OR 3 wherein R 3 is selected from hydrogen and linear or branched hydrocarbyl group;
y is independently 0 or 1; and
the groups R 1 X 1 — and —X 2 R 2 are independently in the ortho or meta position provided that:
i) where y is 0, Y 2 is independently selected from hydrogen, halogen, R 3 , and —OR 3 wherein R 3 is a linear or branched hydrocarbyl group; and
ii) where y is 1, Y 1 or Y 2 is selected from R 3 , and —OR 3 wherein R 3 is selected from hydrogen and a linear or branched hydrocarbyl group.
2. A compound according to claim 1 wherein y is 1.
3. A compound according to claim 1 wherein R 1 , and R 2 are independently selected from C 12-22 alkyl and phenyl.
4. A compound according to claim 1 wherein R 1 , and R 2 are independently selected from C 12 to C 17 alkyl and phenyl.
5. A compound according to claim 1 wherein Y 1 and Y 2 are independently selected from hydrogen, halogen and C 1-4 alkyl.
6. A compound according to claim 1 wherein Y 1 and Y 2 are all hydrogen, R 1 and R 2 are independently selected from C 12 to C 22 alkyl and X 1 and X 2 are —OCO—.
7. A compound according to claim 1 selected from compound of formula Via:
and compound of formula VIb:
wherein R 1 and R 2 , are independently selected from phenyl, C 12-22 alkyl and alkylene aryl of formula —[CH 2 ] z Ar where z is from 1 to 6 and Ar is optionally substituted phenyl.
8. A method of making a colour-change composition, said method comprising utilizing a compound of formula (VI):
wherein R 1 , and R 2 are independently selected from an optionally substituted linear or branched alkyl group, alkenyl group, alkoxy group, aryl group and an alkylene aryl group having from 5 to 22 carbon atoms;
X 1 and X 2 are independently selected from —OC(O)—, —CO 2 — and O;
Y 1 , and Y 2 are independently selected from hydrogen, halogen, R 3 , and —OR 3 wherein R 3 is selected from hydrogen and an optionally substituted linear or branched hydrocarbyl group;
y is independently 0 or 1; and
the groups R 1 X 1 — and —X 2 R 2 are independently in the ortho or meta position.
9. A colour-change composition comprising: A) an electron donating organic colouring compound, B) an electron accepting compound and C) a compound of formula (VI):
wherein R 1 , and R 2 are independently selected from an optionally substituted linear or branched alkyl group, alkenyl group, alkoxy group, aryl group and an alkylene aryl group having from 5 to 22 carbon atoms;
X 1 and X 2 are independently selected from —OC(O)—, —CO 2 — and O;
Y 1 , and Y 2 are independently selected from hydrogen, halogen, R 3 , and —OR 3 wherein R 3 is selected from hydrogen and an optionally substituted linear or branched hydrocarbyl group;
y is independently 0 or 1; and
the groups R 1 X 1 — and —X 2 R 2 are independently in the ortho or meta position.
10. A colour-change composition according to claim 9 wherein compound A) is selected from the group consisting of 3-(4-diethylamino-2-hexyloxyphenyl)-3-(1-ethyl-2-methylindol-3-yl)-4-azaphthalide, 3,3-bis(1-n-butyl-2-methylindol-3-yl)phthalide, 6′-(diethylamino)-2′-(phenylamino)-3H-spiro[2-benzofuran-1,9′-xanthen]-3-one, 2′-chloro-6′-diethylaminofluoran and 2-(2-chloroanilino)-6-di-n-butylaminofluoran.
11. A colour-change composition according to claim 9 wherein compound B) is selected from the group consisting of 2,2-bis(4′-hydroxyphenyl)hexafluoropropane, 4,4′-Cyclohexylidenebisphenol, 1,1-bis(4′-hydroxyphenyl)-2-methylpropane and mixtures thereof.
12. A colour-change composition according to claim 9 which has a hysteresis range from 10 to 80° C.
13. A colour-change composition according to claim 9 which has a fully coloured temperature T4 higher than ambient temperature and a fully decolorized temperature T1 lower than 20° C.
14. A colour-change composition according to claim 9 further comprising a non-ionic surfactant.
15. A colour-change microencapsulated pigment comprising a microencapsulated composition according to claim 9 .
16. An ink composition for a writing implement which comprises a colour-change microencapsulated pigment according to claim 15 .
17. A writing implement comprising a writing device and an ink composition according to the claim 16 .
18. A colour-change composition or a colour-change microencapsulated pigment according to claim 9 wherein component C) is such that said composition or pigment has a T2 temperature at 0° C. and a T3 temperature above 50° C.
19. An indicator including the colour change composition according to claim 9 , wherein said composition further comprises a first portion in its coloured state and a second portion in its discolored state.
20. A process for producing an indicator according to claim 19 comprising providing a support with a first portion of the colour-change composition, having colour change temperatures T1 comprising a fully colored temperature, T2 comprising a minimum discolored state retaining temperature, T3 comprising a maximum color-retaining temperature and T4 comprising a fully decolorized temperature, heating the first portion of the colour-change composition, pigment or ink to a temperature exceeding T4, cooling a second portion of the colour-change composition, pigment or ink composition to a temperature below T1, applying the said second portion to the support and drying the colour-change composition, pigment or ink composition at temperature not exceeding temperature T3 and not below temperature T2.