Charged particles

Patent metadata

Field	Value
Publication number	US-9403987-B2
Application number	US-201013376874-A
Country	US
Kind code	B2
Filing date	Jun 11, 2010
Priority date	Jun 24, 2009
Publication date	Aug 2, 2016
Grant date	Aug 2, 2016

Abstract

Disclosed is a composition comprising a charged particle of volume 5 nm 3 to 50 million nm 3 preferably having an inorganic core of SiO 2 , AI 2 O 3 , and/or TiO 2 , or a core essentially consisting of an organic pigment and/or pigment derivative, and a counter ion which is separable from the particle and is not covalently linked to the particle, said counter ion comprising a silicon atom which is directly bound to a carbon atom. Preferably, said charged particle comprises a dye attached to said inorganic core and said counter ion comprises a (poly)siloxane moiety linked via suitable bridge members to a quaternary, positively charged, nitrogen or phosphorus atom, or to a moiety carrying an anionic functional group. Said composition may be used e.g. in the form of a homogenous dispersion in an electrophoretic display.

First claim

The invention claimed is:

1. A composition comprising:
a charged particle of volume 5 nm 3 to 500 million nm 3 having an inorganic core, and
a counter ion which is separable from the particle and is not covalently linked to the particle, said counter ion comprising a polysiloxane moiety linked via suitable bridge members to a positively or negatively charged functional group, wherein a dye is covalently bound to the core.

2. The composition according to claim 1 , wherein the inorganic core is a SiO 2 , Al 2 O 3 , TiO 2 or mixed SiO 2 , Al 2 O 3 , and/or TiO 2 core.

3. The composition according to claim 1 , wherein the dye is covalently bound to an oxygen atom on the surface of the core, via a radical of formula

wherein
q is 1 to 4,
R 1 and R 2 are independently of each other hydrogen, core surface—O—, or a substituent,
X is alkylene,
B is a direct bond or a bridge member extending to D, and
D is the charged residue of a dye.

4. The composition according to claim 1 , wherein the dye is selected from the group consisting of a magenta dye of formula (4), a yellow dye of formula (12), a cyan dye of formula (17), a blue dye of formula (24), and a magenta dye of formula (32)

5. The composition according to claim 1 , wherein the counter ion has formula (II) or (202), in each of which n represents 5 to 20 and each of R 4 , R 11 and R 12 , independently of each other represents C 1 -C 12 alkyl, or formula (183)

6. The composition according to claim 1 in the form of a homogenous dispersion.

7. The composition according to claim 1 in the form of an electrophoretic ink.

8. A method of using the composition according to claim 1 comprising adding the composition according to claim 1 in an electrophoretic display.

9. A method of using the composition according to claim 1 comprising effecting a color change under electrophoretic conditions.

10. The composition according to claim 1 , wherein the polysiloxane moiety comprises a branched or unbranched backbone comprising two or more linked siloxane groups according to the following formula:
—Si(R′ 2 )—O—

wherein:
R′ is selected from the group consisting of hydrogen, a C 1 -C 7 alkyl group, a C 1 -C 7 haloalkyl group, and —O—Si(R″ 2 )—;
R″ can be the same or different from R′ and is selected from the group consisting of hydrogen, a C 1 -C 7 alkyl group, and a C 1 -C 7 haloalkyl group.

11. A composition comprising:
a charged particle of volume 5 nm 3 to 500 million nm 3 having a core consisting of an organic pigment and/or an organic pigment derivative, and
a counter ion which is separable from the particle and is not covalently linked to the particle, said counter ion comprising a polysiloxane moiety linked via suitable bridge members to a positively or negatively charged functional group,
wherein a dye is covalently bound to the core.

12. The composition according to claim 11 , wherein the organic pigment is selected from the group consisting of carbon black and pigments of the 1-amino-anthraquinone, anthanthrone, anthrapyrimidine, azo, azomethine, quinacridone, quinacridonequinone, quinophthalone, dioxazine, diketopyrrolopyrrole, flavanthrone, indanthrone, isoindoline, isoindolinone, isoviolanthrone, perinone, perylene, phthalocyanine, pyranthrone, thioindigo or oxobenzofuranyliden -dihydroindolone series.

13. The composition according to claim 11 , wherein the polysiloxane moiety comprises a branched or unbranched backbone comprising two or more linked siloxane groups according to the following formula:
—Si(R′ 2 )—O—

wherein:
R′ is selected from the group consisting of hydrogen, a C 1 -C 7 alkyl group, a C 1 -C 7 haloalkyl group, and —O—Si(R″ 2 )—O—;
R″ can be the same or different from R′ and is selected from the group consisting of hydrogen, a C 1 -C 7 alkyl group, and a C 1 -C 7 haloalkyl group.

14. A method of using a counter ion comprising:
adding a polysiloxane moiety linked via suitable bridge members to a quaternary, positively charged, nitrogen or phosphorus atom, or to a moiety carrying an anionic functional group in electrophoresis;
wherein the counter ion has formula (II) or (202), in each of which n represents 5 to 20 and each of R 4 , R 11 and R 12 , independently of each other represents C 1 -C 12 alkyl, or formula (183)

15. The method according to claim 14 , wherein the polysiloxane moiety comprises a branched or unbranched backbone comprising two or more linked siloxane groups according to the following formula:
—Si(R′ 2 )—O—

wherein:
R′ is selected from the group consisting of hydrogen, a C 1 -C 7 alkyl group, a C 1 -C 7 haloalkyl group, and —O—Si(R″ 2 )—;
R″ can be the same or different from R′ and is selected from the group consisting of hydrogen, a C 1 -C 7 alkyl group, and a C 1 -C 7 haloalkyl group.

Assignees

• Hayoz Pascal
• Lamatsch Bernd
• Lamatsch Achim
• Fontana Margherita
• Burkhardt Stephan
• Michau Laurent
• Lehmann Urs
• Bugnon Philippe
• Basf Se

Inventors

• Hayoz Pascal
• Lamatsch Bernd
• Fontana Margherita
• Burkhardt Stephan
• Michau Laurent
• Lehmann Urs
• Bugnon Philippe

Classifications

• G02F1/167

  by electrophoresis · CPC title

• C09B69/103

  containing a diaryl- or triarylmethane dye · CPC title

• C09B69/008 Primary

  Dyes containing a substituent, which contains a silicium atom · CPC title

• C09B69/04

  of anionic dyes with nitrogen containing compounds · CPC title

• G02F2001/1678

  characterised by the composition or particle type · CPC title