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US 9,499,707 B2Granted
Water soluble and water fast dyes for ink jet printing
AssigneeRex-Tone Industries Ltd
InventorsKurt Battig, Damien Moigno
Life of this patent
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Abstract
The invention relates to azo dyes of desulfo-K-acid [CA: 35400-55-6], their salts, a method for the preparation of these dyes, or salts thereof, a liquid phase comprising at least one of these dyes, a method for applying the liquid phase on a substrate, a printed matter and the use of these dyes in water-based inks for inkjet printing, in writing utensil or dyeing solutions for manufacturing color filters for optical and opto-electronic applications.
Claims24
A dye D1 of formula I,
- wherein
- M is selected from the group consisting of H, Li, Na, K, and N(HkR6m),
- wherein
- each R6 is selected from the group consisting of —H, and a substituted or unsubstituted, saturated or unsaturated aliphatic group having 1 to 10 carbon atoms, and
- k is an integer selected from the group consisting of 0, 1, 2, 3, and 4, and
- m=4−k;
- R1 is —H or —N═N—Ar2,
- wherein Ar2 is a substituted or unsubstituted monocyclic, polycyclic or condensed, at least one aromatic group containing fragment, which at least one aromatic group comprises at least one five- or one six-membered homo- or heterocyclic structure,
- wherein the heterocyclic structure comprises at least one hetero-atom,
- which heteroatom is N, O or S;
- R2 is selected from the group consisting of —H, —C(═O)R6, —C(═O)—(CH2)v—Ar2, —R6, —(CH2)q—X, —SO2R6, and —SO2Ar2;
- wherein
- X is selected from the group consisting of —SO3M, —SO2NH2, —SO2NHR6, —NHSO2R6, —NO2, —COOM, —COOR6, —CH3, —R6, —NH2, —NHR6, —OR6, —OM, —Cl, —Br, —I, —F, —CN, —CO2NHR6, —Ar2, —N═N—Ar2, —SO2R6 and —NHC(═O)—R6,
- M, R6 and Ar2 are defined as above,
- q is an integer in the range of from 1 to 10, and
- v is an integer in the range of from 0 to 10;
- R3 is —NHR2 or —N═N—Ar2, wherein
- R2 has the meaning as defined above, and
- Ar2 has the meaning as defined above;
- and
- R4 is —H or —N═N—Ar2, wherein Ar2 has the meaning defined above, and
- wherein two of the groups selected from the group consisting of R1, R3, and R4 are —N═N—Ar2, wherein each Ar2 is selected independently from any other Ar2.
19 more elements
A dye D2 comprising two fragments of formula I,
- and one fragment R5 of formula II,
- *—N═N—Ar1—N═N—* (II)
- wherein
- M is selected from the group consisting of H, Li, Na, K, and N(HkR6m),
- wherein
- each R6 is selected from the group consisting of —H and a substituted or unsubstituted, saturated or unsaturated aliphatic group having 1 to 10 carbon-atoms, and
- k is an integer selected from the group consisting of 0, 1, 2, 3, and 4, and
- m=4−k;
- R2 is selected from the group consisting of —H, —C(═O)R6, —C(═O)—(CH2)y—Ar2, —R6, —(CH2)q—X, —SO2R6, and —SO2Ar2;
- wherein Ar2 is a substituted or unsubstituted monocyclic, polycyclic or condensed, at least one aromatic group containing fragment, which at least one aromatic group comprises at least one five- or one six-membered homo- or heterocyclic structure,
- wherein the heterocyclic structure comprises at least one hetero-atom,
- which heteroatom is N, O or S;
- and
- wherein
- X is selected from the groups consisting of —SO3M, —SO2NH2, —SO2NHR6, —NHSO2R6, —NO2, —COOM, —COOR6, —CH3, —R6, —NH2, —NHR6, —OR6, —OM, —Cl, —Br, —I, —F, —CN, —CO2NHR6, —Ar2, —N═N—Ar2, —SO2R6 and —NHC(═O)—R6,
- M, R6 and Ar2 are defined as above,
- q is an integer in the range of from 1 to 10, and
- v is an integer in the range of from 0 to 10;
- R3 is —NHR2 or —N═N—Ar2, wherein
- R2 has the meaning as defined above, and
- Ar2 has the meaning as defined above;
- wherein Ar1 is a substituted or unsubstituted, monocyclic, polycyclic or condensed, at least one aromatic group containing linker, which at least one aromatic group comprises at least one five- or one six-membered homo- or heterocyclic structure,
- wherein the heterocyclic structure comprises at least one hetero-atom,
- which heteroatom is N, O or S;
- wherein, independently for each fragment of formula I, R2, R3 and M have the meaning as defined above,
- wherein R1 and R4 of each fragment of formula I are selected from the group consisting of
- a. —H,
- b. —N═N—Ar2,
- c. —R5,
- d. formula III:
- wherein
- r represents the number of X substituents in formula III and is an integer in the range of from 1 to 5, and X has the meaning as defined above,
- M is as defined above, and
- e. formula VI:
- wherein
- each X has the meaning as defined above,
- T is selected from the group consisting of C, N and P,
- u represents the number of X substituents in formula VI and is an integer between 0 and 6;
- wherein, in each of the two fragments of formula I, at least one of the groups R1 and R4 equals R5 as defined for formula II, and wherein R5 is linked at the positions marked with * to the two fragments of formula I, and
- wherein in each fragment of formula I, if R1 equals R5, then R4 is selected from the group consisting of formula III and formula VI.
37 more elements
Dependencies are inferred from the claim text.