Thiophene azo carboxylate dyes and laundry care compositions containing the same

Patent metadata

Field	Value
Publication number	US-9567465-B2
Application number	US-201514831935-A
Country	US
Kind code	B2
Filing date	Aug 21, 2015
Priority date	Jun 3, 2011
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

Abstract

This application relates to thiophene azo carboxylate dyes for use as hueing agents, laundry care compositions comprising such dyes that may serve as hueing agents, processes for making such dyes and laundry care compositions and methods of using the same. The aforementioned dyes contain a formally charged moiety and are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. Suitable chromophore components generally fluoresce blue, red, violet, or purple color when exposed to ultraviolet light, or they may absorb light to reflect these same shades. Such dyes are advantageous in providing a hueing effect, for example, a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics. Such dyes are also generally stable to bleaching agents used in laundry care compositions.

First claim

We claim:

1. A composition comprising a thiophene azo carboxylate dye containing a carboxylic acid moiety, wherein said thiophene azo carboxylate dye is represented by general Formula (I):

wherein:
a.) R 1 , R 2 and R 3 are independently selected from hydrogen, (C 1 -C 4 )-alkyl, (C 3 -C 10 )-aryl, carboxylate, cyano, sulfonate, phosphonate, sulfate, acetate, nitro, (C 1 -C 4 )-alkyl ester, halogen or amino moiety; and
b.) X is a moiety having Formula (II) below:

wherein:
i.) R 4 is selected from a moiety having Formula (III) below

wherein:
 each R 8 is independently selected from hydrogen, C 1 -C 8 alkyl optionally substituted with a hydroxy, or acetyl;
 m is an integer from 0 to 10;
 Y is —OC(O)GCO 2 M wherein M is H or a charge balancing cation; G is an organic group selected from the group consisting of a substituted or unsubstituted succinic, maleic, glutaric, adipic or phthalic anhydride and is present as shown below,

 said anhydride having a molecular weight less than about 353 Daltons;

R 5 is selected from C 1 -C 12 alkyl moiety, a C 2 -C 12 ether moiety; C 6 -C 10 aryl moiety or C 7 -C 12 arylalkyl moiety;
wherein the index a is an integer from 0 to 4 and each R 6 may be independently selected from a C 1 -C 6 alkyl, a C 1 -C 4 alkoxy, a nitro, a hydroxyl, a halogen, or —NHC(O)R 22 wherein R 22 is selected from H, —NH 2 , C 1 -C 6 alkyl, phenyl, —(CH 2 ) s OR 23 where the index s is 1 or 2 and R 23 is selected from Me, phenyl, and —CO 2 CH 2 CN; —NHSO 2 R 24 wherein R 24 is C 1 -C 4 alkyl or phenyl; said alkyl, alkoxy and acetamido moieties may be optionally substituted with a carboxylate moiety.

2. The composition of claim 1 , wherein said thiophene azo carboxylate dye has, in the wavelength range of about 400 nm to about 750 nm in methanol solution, a maximum extinction coefficient greater than about 1000 liter/mol/cm.

3. The composition of claim 2 , wherein said thiophene azo carboxylate dye has, in the wavelength range of about 540 nm to about 630 nm, a maximum extinction coefficient from about 20,000 to about 100,000 liter/mol/cm.

4. The composition of claim 3 , wherein said thiophene azo carboxylate dye has, in the wavelength range of about 560 nm to about 610 nm, a maximum extinction coefficient from about 20,000 to about 65,000 liter/mol/cm.

5. The composition of claim 1 , wherein said thiophene azo carboxylate dye has a molecular weight from greater than 232 Daltons, from about 233 Daltons to about 5000 Daltons, from about 365 Daltons to about 2500 Daltons, or even from about 423 Daltons to about 1000 Daltons.

6. A composition comprising a thiophene azo carboxylate dye of Formula (XII):
A-N═N—X   Formula XII

wherein the A moiety is selected from the group consisting of:

No.
A

9

10

11

15

23

34

35

37

38

39

41

43

Assignees

• Milliken & Co

Inventors

• Torres Eduardo
• Dey Sanjeev Kumar
• Bruhnke John David
• Miracle Gregory Scot

Classifications

• C09B29/0059 Primary

  the heterocyclic ring containing only sulfur as heteroatom · CPC title

• C09B69/00

  Dyes not provided for by a single group of this subclass · CPC title

• C09B29/0802

  containing COOH · CPC title

• C11D3/40

  Dyes {; Pigments} · CPC title

• C09B43/263 Primary

  Polycarboxylic acids · CPC title