Thiophene AZO carboxylate dyes and laundry care compositions containing the same

Patent metadata

Field	Value
Publication number	US-9752104-B2
Application number	US-201414507860-A
Country	US
Kind code	B2
Filing date	Oct 7, 2014
Priority date	Jun 3, 2011
Publication date	Sep 5, 2017
Grant date	Sep 5, 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 laundry care composition comprising:
a) a thiophene azo carboxylate dye containing a carboxylic acid moiety, with the proviso that the thiophene azo carboxylate dye does not have the following
structures

b) a laundry care ingredient wherein said thiophene azo carboxylate dye is represented by general Formula (I):

wherein:
a.) R 1 is an electron-withdrawing moiety, R 2 is an electron-donating moiety, and R 3 is an electron-withdrawing moiety; and
b.) wherein X is a moiety having Formula (II),

wherein, in Formula (II), R 4 is a moiety having Formula (V) below:

wherein each R 11 and R 12 is hydrogen; m=0 and n=4; Y is —OC(O)GCO 2 M wherein M is H or a charge balancing cation; G is an organic group derived from a substituted succinic anhydride having Formula VI,

said anhydride having a molecular weight less than about 353 Daltons:
R 5 is a C 7 -C 12 arylalkyl moiety, namely benzyl (—CH 2 C 6 H 5 ); a=1; R 6 is C 1 -C 6 alkyl, namely methyl.

2. The laundry care 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 laundry care 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 laundry care 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 laundry care 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. The laundry care composition of claim 1 , wherein for said thiophene azo carboxylate dye R 1 is a cyano, R 2 is a (C 1 -C 4 )-alkyl, and R 3 is a cyano.

7. The laundry care composition of claim 1 , wherein for said thiophene azo carboxylate dye X is a moiety having Formula (II) below:

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

wherein
each R 11 and R 12 is hydrogen; m is 0 and n=4,
Y is —OC(O)GCO 2 M wherein M is H or a charge balancing cation; G is an organic group derived from a substituted succinic anhydride having Formula VI,

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

ii.) R 5 is a C 7 -C 12 arylalkyl moiety, namely benzyl (—CH 2 C 6 H 5 );
ii.) a=1; and each R 6 is methyl.

8. The laundry care composition of claim 7 , wherein for said thiophene azo carboxylate dye R 1 is a cyano, R 2 is a (C 1 -C 4 )-alkyl, namely methyl, and R 3 is a cyano.

9. The laundry care composition of claim 1 wherein said thiophene azo carboxylate dye has Formula (X):
A-N═N—X  Formula X

wherein the A moiety is

and wherein X is

wherein G is an organic group derived from a substituted succinic anhydride having Formula XI

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

10. The laundry care composition of claim 1 wherein said thiophene azo carboxylate dye has Formula (XII):
A-N═N—X  Formula XII

wherein the A moiety is

and wherein the X moiety is

wherein G is an organic group derived from a substituted succinic anhydride having Formula XIII,

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

11. The laundry care composition of claim 10 wherein said G moiety of said thiophene azo carboxylate dye is

12. The laundry care composition of claim 1 , wherein said thiophene azo carboxylate dye has the following formula:

wherein the moiety A is

a=1, R 6 is and a methyl in the 4 position; and R 4 is benzyl and R 5 is

13. The laundry care composition of claim 1 , wherein said thiophene azo carboxylate dye has the following formula:

wherein the moiety A is

a=1, R 6 is a methyl in the 4 position; and R 4 is benzyl and R 5 is

14. The laundry care composition of claim 1 , wherein said thiophene azo carboxylate dye has a formula

15. The laundry care composition of claim 1 , said laundry care composition comprising, based on total laundry care composition weight, less than 15% builder, less than 10% builder, or even less than 5% builder.

16. The laundry care composition of claim 1 , said laundry care composition being a multi-compartment unit dose product.

17. The laundry care composition of claim 1 , said laundry care composition comprising, based on total laundry care composition weight, a total of no more than 20% water; a total of no more than 15% water; a total of no more than 10% water; or even a total of no more than 5% water.

Assignees

• Procter & Gamble

Inventors

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

Classifications

• C09B29/0813

  substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl) · CPC title

• C09B69/106

  containing an azo dye · CPC title

• C09B29/0816

  substituted by -COOR · CPC title

• C11D3/42 Primary

  Brightening agents {; Blueing agents} · CPC title

• C11D3/40 Primary

  Dyes {; Pigments} · CPC title