IP Library Granted Patent US 7,572,327
Granted Patent B2
US 7,572,327 · App. 11/172,814 · Granted Aug 11, 2009

Nitrogen-substituted water-dispersible phthalocyanine dyes

Assignee: Silverbrook Research Pty Ltd
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Quick Facts
Patent No.
US 7,572,327
App. No.
11/172,814
Granted
Aug 11, 2009
Kind
B2
Abstract

A phthalocyanine dye of formula (I) is provided: wherein: M is a metal group or is absent; n is 1 or 2; X is selected from —CHR 3 —, —NR 3 —, —O— or —S—; R 1 , R 2 and R 3 are independently selected from hydrogen, C 1-8 alkyl, C 1-8 alkoxy, carboxy, carboxy-C 1-8 alkyl, hydroxyl, hydroxy-C 1-8 alkyl; or R 1 and R 2 , or R 2 and R 3 together are joined to form a C 4-12 aryl or C 3-12 heteroaryl group, optionally substituted with 1, 2, 3 or 4 substituent groups, the or each substituent group being independently selected from C 1-12 alkyl, C 1-12 alkoxy, phenyl-C 1-8 alkyl, phenyl-C 1-8 alkoxy, —(OCH 2 CH 2 ) d OR d , cyano, halogen, amino, hydroxyl, thiol, —SR v , —NR u R v , nitro, phenyl, phenoxy, —CO 2 R v , —C(O)R v , —OCOR v , —SO 2 R v , OSO 2 R v , —NHC(O)R v , —CONR u R v , —CONR u R v , sulfonic acid, sulfonic acid salt and sulfonamide; d is an integer from 2 to 5000; R d is H, C 1-8 alkyl or C(O)C 1-8 alkyl and R u and R v are independently selected from hydrogen, C 1-12 alkyl, phenyl or phenyl-C 1-8 alkyl.

Claims (11)

1. A phthalocyanine dye of formula (IV) or (V):

wherein:

M is H 2 or a metal group;

n is 1 or 2;

each W is independently selected from the group consisting of: hydrogen, sulfonic acid, sulfonic acid salt and sulfonamide,

and wherein at least one W is a sulfonic acid or sulfonic acid salt.

2. The dye of claim 1 , wherein at least one W is a sulfonic acid or sulfonic acid salt of formula —SO 3 Z, wherein:

Z is H, Li, Na, K or N + (R m )(R n )(R S )(R t ); and

R m , R n , R s , R t may be the same or different and are independently selected from the group consisting of: H, C 1-8 alkyl, C 6-12 arylalkyl and C 6-12 aryl.

3. The dye of claim 1 , wherein M is SnCl 2 , V═O or Ga(OH).

4. An inkjet ink comprising a dye according to claim 1 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 29, 2014
From: SILVERBROOK RESEARCH PTY LTD
To: BASF SE
Reel/Frame 033062/0063 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 30, 2006
From: VONWILLER, SIMONE CHARLOTTE; RIDLEY, DAMON DONALD; INDUSEGARAM, SUTHARSINY; STARLING, SCOTT MATTHEW; GONZAGA, GRACIEL; SILVERBROOK, KIA
To: SILVERBROOK RESEARCH PTY LTD
Reel/Frame 017941/0815 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 5, 2006
From: VONWILLER, SIMONE CHARLOTTE; RIDLEY, DAMON DONALD; INDUSEGARAM, SUTHARSINY; STARLING, SCOTT MATTHEW; GONZAGA, GRACIEL
To: SILVERBROOK RESEARCH PTY LTD.
Reel/Frame 017163/0905 →
Continuity (1)
Related Publication 20070008392A1 · Jan 11, 2007