Xanthene dyes for ink jet printing

• US 5,279,656 A
• Filed: 11/09/1992
• Issued: 01/18/1994
• Est. Priority Date: 11/15/1991
• Status: Expired due to Fees

• Current Assignee: Zeneca Incorporated (Astrazeneca PLC)
• Original Assignee: Imperial Chemical Industries PLC (IMPERIAL CHEMICAL INDUSTRIES)
• Inventors: Gregory, Peter, Kenyon, Ronald W.
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US07/973,666
• Time in Patent Office: 435 Days
• Field of Search: 106/22 H, 106/22 K, 549/227, 549/394
• US Class Current: 106/31.43
• CPC Class Codes: C07D 311/82 Xanthenes
• CPC Class Codes: C09B 11/28 Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
• CPC Class Codes: C09B 67/0041 mixtures containing one azo dye

Abstract

A compound of Formula (1): ##STR1## wherein: X¹ is a sulpho or carboxy group;

each X² independently is a substituent;

m has a value of from 0 to 2;

Y¹ and Y² are each independently alkyl or halo; and

Z is a carboxy group.

The above compounds may be used as colorants for ink jet printing inks either alone or as a mixture with a second magenta compound.

Claims

1. A compound of Formula (1):

##STR8## wherein;

X¹ is a sulpho or carboxy group;

each X² independently is a substituent;

m has a value of from 0 to 2;

Y¹ and Y² are each independently alkyl or halo; and

Z is a carboxy group.

2. A compound according to claim 1 wherein X¹ is a carboxy group.

3. A compound according to claim 1 or claim 2 wherein Y¹ and Y² are each independently C_1-4 -alkyl or halo.

4. A compound according to claim 1 wherein one or both of the groups represented by Z are at the 3- or 5-position.

5. A compound according to claim 1 wherein X² contains less than 7 carbon atoms.

9. A composition comprising a compound according to claim 1 and a second water-soluble magenta compound in relative amounts, by weight, in the range 95:

5 to 5;

95.

10. A composition according to claim 9 wherein the second magenta compound is of Formula (5) or salt thereof:

space="preserve" listing-type="equation">Ar.sup.1 N=N--J--W--(NR.sup.1 --L--NR.sup.2 --W).sub.n --J--N=NAr.sup.2(

     5)

wherein;

##STR10## Ar¹ and Ar² are each independently aryl or substituted aryl providing at least one of Ar¹ and Ar² has at least one substituent selected from COOH and COSH;

each R¹ and R² is independently H, alkyl, substituted alkyl, alkenyl or substituted alkenyl;

L is a divalent organic linking group;

n is 0 or 1;

each W independently is carbonyl or a group of the formula (6), (7) or (8);

##STR11## each B independently is NR³ R⁴, SR⁵ or OR⁵ ;

each D independently is H, Cl, B, SR⁶ or OR⁶ ;

each E independently is Cl or CN;

R³, R⁴, R⁵ and R⁶ are each independently H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, aralkyl, substituted aralkyl or R³ and R⁴ together with the nitrogen atom to which they are attached form a 5 or 6 membered ring;

provided the compound of Formula (5) has at least as many groups selected from --COOH and --COSH as --SO₃ H groups.

11. An ink comprising a compound according to claim 1 and a liquid medium.

12. A process for printing a substrate with an ink using an ink jet printer comprising forming the ink into small droplets by ejection from a reservoir through a small orifice so that the droplets of ink are directed at a substrate, wherein said ink is as defined in claim 11.

13. A paper or an overhead projector slide printed with a compound according to claim 1.

14. An ink comprising a composition according to claim 10 and a liquid medium.

6. A compound of Formula (1):

##STR9## wherein;

X¹ is a sulpho or carboxy group;

each X² independently is halo, sulpho, C_1-4 -alkyl, C_1-4 -alkoxy or carboxy;

m has a value of from 0 to 2;

Y¹ and Y² are each independently C_1-4 -alkyl or halo; and

Z is a carboxy group.

7. A compound according to claim 6 wherein the carboxy and sulpho groups are of formula --CO₂^- M⁺ or --SO₃^- M⁺ wherein M⁺ is an alkali metal, substituted ammonium or NH₄⁺.

8. A compound according to claim 6 wherein the carboxy and sulpho groups are of formula --CO₂^- M⁺ or --SO₃^- M⁺ wherein M⁺ is an alkali metal, ammonium or a group selected from the group consisting of (CH₃)₃ N⁺ H, (CH₃)₂ N⁺ H₂, H₂ N⁺ (CH₃)(CH₂ CH₃), CH₃ N⁺ H₃, CH₃ CH₂ N⁺ H₃, H₂ N⁺ (CH₂ CH₃)₂, CH₃ CH₂ CH₂ N⁺ H₃, (CH₃)₂ CHN⁺ H₃, isopropylammonium, pyridinium, piperidinium and morpholinium.

15. A paper or an overhead projector slide printed with a composition according to alaim 9.