Use of comb polymers as soil release polymers

Details Use of comb polymers as soil release polymers Use of comb polymers as soil release polymers

2000-02-16

2001-07-03

Gupta, Yogendra (Department: 1751)

Cleaning compositions for solid surfaces, auxiliary compositions

Cleaning compositions or processes of preparing

Specific organic component

C510S276000, C510S346000, C510S356000, C510S357000, C510S361000, C510S414000, C510S426000, C510S434000, C510S477000, C510S488000, C510S489000, C510S533000

Reexamination Certificate

active

06255274

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to the use of soil release comb polymers in detergents and cleaning agents.
DESCRIPTION OF THE RELATED ART
Soil release polymers have for many years been the subject of intensive development work. Originally developed as textile assistants for finishing manmade fibers, in particular polyester fibers, they are now used as so-called washing aids also in detergents and cleaning agents for household laundry. Common names for such compounds having a soil-detaching capability are “soil release polymers” or “soil repellents”, because they impart soil-repellent properties to the treated surfaces.
The predominant number of soil release polymers are polyesters based on terephthalic acid, polyalkylene glycols and monomer glycols.
Owing to their structural relationship, these are readily adsorbed by polyester fabrics or polyester-containing union fabrics from an aqueous solution or a wash liquor and will form a hydrophilic film on the hydrophobic fabric. As a result of this, the affinity of the fabric to hydrophobic oily and greasy dirt is reduced. At the same time, the wettability of the polyester fabric with the aqueous wash liquor is improved. Both lead to easier release of oily and greasy surface dirt, which is usually very difficult to remove from polyester fabrics. In addition, the moisture transport (water absorption and absorptivity) in the treated hydrophobic fabrics, such as polyester or polyester/cotton union fabrics, is substantially improved, which has a positive effect on the wearing properties. In addition, the soil release polymers also improve the antistatic properties and the frictional properties. This facilitates the handling of the fabrics during textile processing.
Soil release polyesters of the abovementioned type which contain anionic groups, such as, for example, sulfo groups, are also known (EP-A-24 985, U.S. Pat. No. 4,427,557, WO 94/03 570, WO 93/21 294, WO 95/02 030).
SUMMARY OF THE INVENTION
It has now been found that so-called comb polymers, as described in DE 198 09 948.7, can be used as soil release polymers.
The invention therefore relates to the use of comb polymers as soil release polymers, these comb polymers being obtained by condensation of
a) a polycarboxylic acid or a polyalcohol
b) one or more optionally sulfo-substituted polyalcohols having 2 to 4 OH groups or polyglycols of the formula HO—(XO)
a
—H, in which X is C
2
H
4
and/or C
3
H
7
and a is a number from 2 to 35, preferably from 2 to 5,
c) one or more optionally sulfonated C
2
-C
10
-dicarboxylic acids and
d) one or more compounds of the formulae NH
2
R, NHR
2
, ROH, R
1
COOH, HO(XO)
b
—H and HO(CH
2
CH
2
)
d
SO
3
K, in which R is C
1
-C
22
-alkyl or C
6
-C
10
-aryl, R
1
is C
1
-C
22
-alkyl, C
1
-C
22
-sulfoalkyl, C
6
-C
10
-aryl or C
6
-C
10
-sulfoaryl, X is C
2
H
4
and/or C
3
H
7
, b is a number from 3 to 40, preferably 3 to 20, d is a number from 1 to 10, preferably 1 to 4, and K is a cation.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The polymeric main chain of the comb polymers according to the invention preferably comprises polymeric aliphatic, cycloaliphatic or aromatic polycarboxylic acids or derivatives thereof, such as, for example, polyacrylic acid, polymethacrylic acid, polymaleic acid, polymaleic anhydride and polynorbornenic acid or esters thereof with aliphatic, cycloaliphatic or aromatic C
1
-C
22
-alcohols. The number average molecular weights of these polycarboxylic acids may be between 1000 and 2,000,000 g/mol, with the range of 2000 to 100,000 g/mol being preferred.
Furthermore, the polymeric main chain may comprise a polymeric aliphatic, cycloaliphatic or aromatic polyalcohol, such as, for example, polyvinyl alcohol or polynorbornyl alcohol. The average molecular weights of these polyalcohols may be between 1000 and 2,000,000 g/mol, the range of 2000 to 100,000 g/mol being preferred.
In addition, random, alternating or block-type copolymers of the two abovementioned classes of compounds with other vinylic monomers, such as, for example, styrene, acrylamide, &agr;-methylstyrene, N-vinylpyrrolidone, N-vinylpyridine, N-vinylformamide, N-vinylcaprolactone, vinyl acetate or acrylamidopropylenesulfonic acid, vinylsulfonic acid, vinylphosphonic acid and the alkali metal, alkaline earth metal and ammonium salts thereof, may also be used.
These polycarboxylic acids and polyalcohols are reacted with a mixture of the components b) to d) as defined above, oligomeric polyester side chains forming. Suitable components b) are optionally sulfo-substituted aromatic, aliphatic or cycloaliphatic polyalcohols as defined above, for example ethylene glycol, 1,2-propanediol, 1,2-butanediol, 1,4-butanediol, sodium 1,2-dihydroxypropoxyethanesulfonate, glycerol, pentaerythritol.
The component c) comprises at least difunctional aromatic, aliphatic and/or cycloaliphatic C
2
-C
10
-dicarboxylic acids, such as, for example, terephthalic acid, isophthalic acid, cyclohexanedicarboxylic acid, succinic acid, adipic acid, 2,6-naphthalenedicarboxylic acid and optionally one or more sulfonated aromatic, aliphatic or cycloaliphatic C
3
-C
10
-dicarboxylic acids, for example sulfosuccinic acid or 5-sulfoisophthalic acid or mixtures thereof.
To improve the water solubility, in the case of the components containing sulfo groups, the sulfo group is preferably present as an alkali metal, alkaline earth metal or ammonium or mono-, di-, tri- or tetraalkyl- or -hydroxyalkyl-ammonium salt, it being possible for one alkyl group to contain 1 to 22 carbon atoms and the other alkyl groups, as well as the hydroxyalkyl group, to contain 1 to 4 carbon atoms.
Component d) is a so-called endcap group. Suitable terminal groups of this type are: aromatic, aliphatic or cycloaliphatic monoalkylamines or dialkylamines, it being possible for the alkyl group to contain 1 to 22 carbon atoms; aromatic, aliphatic or cycloaliphatic monocarboxylic acids having 1 to 200 carbon atoms in the case of the aliphatic monocarboxylic acids and 6 to 10 carbon atoms in the case of the aromatic or cycloaliphatic monocarboxylic acids;
aliphatic monoalcohols having 1 to 22 carbon atoms or aromatic and cycloaliphatic monoalcohols having 6 to 10 carbon atoms;
polyalkoxy compounds of the formula HO—(AO)
x
R, A being —C
2
H
4
— or —C
3
H
7
—, x being a number from 3 to 40, preferably 3 to 20, and R being hydrogen or C
1
-C
22
-alkyl.
Sulfonated mono- or polyethylene glycols of the formula H(OCH
2
CH
2
)
d
SO
3
M, d being a number from 1 to 10, preferably from 1 to 4, and M being an alkali metal or alkaline earth metal cation, are particularly preferred as component e). The comb polymers according to the invention may alternatively also be free of components according to d). In this case, the side chains of the comb polymer are terminated by a hydrogen atom.
The comb polymers preferably comprise 0.5 to 10% by weight of the component a), 15 to 45% by weight of the component b), 30 to 70% by weight of the component c) and 10 to 30% by weight of the component d).
The number average molecular weights of the comb polymers may advantageously be between 2000 and 2,000,000 g/mol, particularly advantageously between 2000 and 100,000 g/mol, the range of 2000-30,000 g/mol preferably being used, very particularly advantageously 5000-15,000 g/mol.
The synthesis of the comb polymers is carried out by processes known per se, by first heating the components a) to d) to temperatures of 160 to about 220° C. at atmospheric pressure with the addition of a catalyst. The reaction is then continued under reduced pressure at temperatures of 160 to about 240° C. with removal of excess glycols by-distillation. The known transesterification and condensation catalysts of the prior art, such as, for example, titanium tetraisopropylate, dibutyltin oxide or antimony trioxide/calcium acetate, are suitable for the reaction. Regarding further details for carrying out the process, reference is made to EP-442 101.
The invention also relates to the use of these comb polymers in detergents and cleaning agents, in particular for increasing

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