Polyvinylpyridinium derivatives as anti-dye transfer agents

Details Polyvinylpyridinium derivatives as anti-dye transfer agents Polyvinylpyridinium derivatives as anti-dye transfer agents

1999-04-28

2001-02-20

Hardee, John (Department: 1751)

Cleaning compositions for solid surfaces, auxiliary compositions

Cleaning compositions or processes of preparing

Specific organic component

C526S265000

Reexamination Certificate

active

06191098

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to water-soluble polyvinylpyrridinium derivative containing a quaternary nitrogen and an anionic moiety selected from a sulfonate or a carboxylate functionality. The polyvinylpyrridinium derivatives are useful as anti-dye transfer and color protection agents in detergent compositions, especially detergent compositions containing a high level of anionic surfactants.
BACKGROUND OF THE INVENTION
One of the most persistent and troublesome problems arising during modern fabric laundering operations is the tendency of some colored fabrics to release dye into the laundering solutions. The dye is then transferred onto other fabrics being washed therewith.
One way of overcoming this problem would be to complex or adsorb the fugitive dyes washed out of dyed fabrics before they have the opportunity to become attached to other articles in the wash. Polyvinylpyrrolidone, by virtue of its dye complexation ability, has been used to inhibit dye deposition during washing of colored fabrics under laundry conditions. The performance of polyvinylpyrrolidone as a dye transfer inhibitor, however, is adversely affected by the presence of high levels of anionic surfactants in the washing process.
Other polymers which have been used in detergent compositions to inhibit dye transfer include polyvinylimidazole, polyvinylpyridine N-oxide, polyvinylimidazole and copolymers of polyvinylpyridine and polyvinylimidazole. DE 2 814 287-A describes detergent compositions containing N-vinyl imidazole homo- or copolymer in combination with anionic and/or nonionic surfactants and other detergent ingredients. WO 95/03390 describes dye inhibiting polymers of polyvinylpyrrolidone, polyamine N-oxide, and vinylimidazole. U.S. Pat. No. 5,460,752 describes polyamine N-oxide polymers.
U.S. Pat. No. 5,627,151 describes copolymers of vinylpyrrolidone or vinylimidazole, vinylpyridine or dimethylaminoethyl methacrylate or dimethylaminopropylmethacrylamide, including up to 20% vinylacetate, for use in laundry detergents. U.S. Pat. No. 5,466,802 describes poly(4-vinylpyridine-N-oxide) and copolymers of vinylpyrrolidone and vinylimidazole. EP 754748 describes vinylpyridine copolymers and formic acid. U.S. Pat. No. 5,458,809 describes poly(4-vinylpyridine-N-oxide). WO 95/27038 describes poly(4-vinylpyridine-N-oxide), polyvinylpyrrolidone, polyvinylpyrrolidone-vinylimidazole and copolymers of vinylpyrrolidone and vinylimidazole.
EP 372 291 describes a process for washing discoloration-sensitive textiles. The wash liquor contains anionic
onionic surfactants and water-soluble polymers, for example, copolymers N-vinylimidazole, N-vinyloxazolidone or N-vinylpyrrolidone. EP 327 927 describes a granular detergent additive comprising water-soluble polymeric compounds based on N-vinylpyrrolidone and/or N-vinylimidazole and/or N-vinyloxazolidone and cationic compounds. DE 4027832 describes electrolyte-free liquid detergent compositions comprising zeolite A, nonionic surfactants and homo- and copolymers selected from N-vinylpyrrolidone and/or N-vinylimidazole and/or N-vinyloxazolidone. U.S. Pat. No. 5,776,879 describes water-soluble poly(vinylpyridine betaines) containing a quaternary nitrogen and a carboxylate salt, which have effective dye transfer inhibitor properties.
It would be advantageous to develop a polymer which provides anti-dye transfer and color protection properties to detergent compositions having a high level of anionic surfactants. The polymer should also provide anti-dye transfer and color protection properties without adversely affecting stain or soil removal or soil redeposition. In addition, the polymer should be effective on a broad range of dyes present in the wash water.
SUMMARY OF THE INVENTION
The invention provides a water-soluble polyvinylpyrridinium derivative comprising a quaternary nitrogen and an anionic moiety selected from a sulfonate and/or a carboxylate functionality. The polyvinylpyrridinium derivative has the structure:
wherein a is a repeating unit of 1 to 100; b is a repeating unit of 0 to 99; c is a repeating unit of 0 to 99; d is a repeating unit of 0 to 99; R is selected from the group consisting of (CR
1
R
2
)
m1
, benzene, and substituted benzene; Y is selected from the group consisting of (CR
3
R
4
)
m2
, benzene, and substituted benzene; substituted benzene is independently a benzene substituted with a group selected from the group consisting of amino moeity, nitro moiety, halogen moiety, and combinations thereof; Z is derived from an ethylenically unsaturated monomer; m
1
and m
2
are independently 0 to 10; M
+
is independently a cation wherein M is selected from the group consisting of hydrogen, ammonia, alkali metals, alkaline earth metals, zinc, copper, organic amines, amino acids, and amino saccharides; R
1
, R
2
, R
3
, and R
4
are independently selected from the group consisting of hydrogen, hydroxyl, alkyl having C
1
to C
6
, aryl having C
6
to C
18
, and alkaryl having C
7
to C
18
; and X
−
is independently a halide, with the proviso that if Y is benzene or substituted benzene then a is 0 to 99 and b is 1 to 100.
The polyvinylpyrridinium derivatives of the invention inhibit dye transfer in detergent compositions having a high level of anionic surfactants. The polymer also provides anti-dye transfer and color protection properties without adversely affecting stain or soil removal or soil redeposition. In addition, the polymer is effective on a broad range of dyes present in the wash water.
DESCRIPTION OF THE INVENTION
In accordance with the invention, the water-soluble polyvinylpyrridinium derivative comprises a quaternary nitrogen and an anionic moiety selected from a sulfonate and/or a carboxylate functionality. The polyvinylpyrridinium derivative has the general structure:
wherein a is a repeating unit of 1 to 100; b is a repeating unit of 0 to 99; c is a repeating unit of 0 to 99; d is a repeating unit of 0 to 99; R is selected from the group consisting of (CR
1
R
2
)
m1
, benzene, and substituted benzene; Y is selected from the group consisting of (CR
3
R
4
)
m2
, benzene, and substituted benzene; substituted benzene is independently a benzene substituted with a group selected from the group consisting of amino moeity, nitro moiety, halogen moiety, and combinations thereof; Z is derived from an ethylenically unsaturated monomer; m
1
and m
2
are independently 0 to 10; M
+
is independently a cation wherein M is selected from the group consisting of hydrogen, ammonia, alkali metals, alkaline earth metals, zinc, copper, organic amines, amino acids, and amino saccharides; R
1
, R
2
, R
3
, and R
4
are independently selected from the group consisting of hydrogen, hydroxyl, alkyl having C
1
to C
6
, aryl having C
6
to C
18
, and alkaryl having C
7
to C
18
; and X
−
is independently a halide, with the proviso that if Y is benzene or substituted benzene then a is 0 to 99 and b is 1 to 100.
In a preferred embodiment of the polyvinylpyrridinium derivative, a is 50 to 100; b is 0 to 50; c is 0 to 50; d is 0 to 50, more preferably a is 50 to 100; b is 0 to 10; c is 0 to 10; d is 0 to 50; R is selected from the group consisting of (CR
1
R
2
)
m1
and benzene; Y is selected from the group consisting of (CR
3
R
4
)
m2
and benzene; Z is derived from a nitrogen-containing ethylenically unsaturated monomer; m
1
and m
2
are independently 1 to 6; M
+
is independently a cation wherein M is sodium or potassium; R
1
, R
2
, R
3
, and R
4
are independently hydrogen or hydroxyl; and X
−
is independently selected from fluoride, chloride, iodide, and bromide, more preferably chloride.
The letter Z represents the derivative of an ethylenically unsaturated monomer. Preferably, the ethylenically unsaturated monomer is a nitrogen-containing, ethylenically unsaturated monomer which may be in the form of free bases, salts with organic or inorganic acids, or in quaternized form. In addition, such nitrogen-containing, ethylenically unsaturated monomers may be functionalized to from the corresponding betaine or sult

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