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US005622926A
United States Patent [191 [11] Patent Number: 5,622,926
Schade et al. [45] Date of Patent: Apr. 22, 1997
TABLE 2
Polymer prepared
according to Copolymer Comparative
Example: 1 2 3 4 5 6 7 8 9 1 2 3 4 Example 1
Direct 31.1 30.4 33.7 32.8 26.2 24.9 35.7 27.7 30.1 25.7 29.3 26.5 25.8 10.8
Black 51
Direct Blue 29.4 34.4 30.5 89.0 23.2 34.8 38.2 32.0 22.7 18.5 31.2 24.2 28.9 10.8
218
Direct 78.8 84.0 80.6 85.2 71.8 73.3 82.2 78.6 68.2 69.6 70.3 69.3 64.1 31.2
Red 79
Direct 76.6 79.3 81.0 80.9 74.3 71.1 82.3 73.4 71.1 79.5 78.4 75.8 68.6 27.8
Black 22
Direct Blue 96.9 97.2 97.1 97.5 90.7 91.7 97.6 96.1 91.9 93.8 92.7 91.2 91.7 4316
71
The Examples show that the novel polymers exhibit 50 The results in Table 2 show that the novel polymers have
substantially improved elimination behavior in sewage 51113913119311)! _h1gher 91119191193 than comparable Polymers
Sludge than polyvinylpyrrolidong having a similar proportion of a less water-soluble compo
Usa Examples nent, for example Comparative Example 1.
washing tests lNfAccizngl mer which is obtainable b free radical co 0
To test the e?iciency, white test fabric was washed 55 ' . y . y p
. . . lymerization of a rmxture of
together with colored textile samples of cotton in a laun- _ I _ _ _
derometer. The dye transfer which occurred was measured (a) from 20 to 95% by Welght Ofa l'vmyhmldazole Ofthe
photometrically. The particular depths of color were deter- formula (I)
mined from the re?ectance values measured on the indi- 60 N R (I)
vidual test fabrics, and the efficiency of the polymers can be "
derived from the said depths of color. An e?iciency of 100%
means that the test fabric retained its original depth of color, N
ie. it was not colored. An efficiency of 0% is determined in \
the case of a test fabric which has the same depth of color 65 CH_CH2
as a test cloth which was washed without the addition of a where R is H, CH3 or CZH5 and n is from 1 to 3, or a
dye transfer-inhibiting additive. mixture of l-vinylimidazoles of the formula I which
5,622,926
13 14
contains up to 20% by weight of other monoethyleni- 3. A detergent comprising surfactants, builders, and other
cally unsaturated monomers, and conventional components, which contains from 0.1 to 10%
(b) from 5 to 80% by weight of water-insoluble polymers by Weight of a copolymer prepared by free radical copoly
selected from the group consisting of unsaturated poly- menzanon of a mlxmre of
esters; homopolymers of butadiene; copolymers of (a) fTQm 20f) 95% by Weight of l'vinylpyrrolidone, a
butadiene with styrene, acrylonitn'le, acrylates of alco- l'vlnyhmldazole of the formula (I)
hols of l to 8 carbon atoms, isoprene, vinyl ethers N
(1)
where the alkyl chain is of l to 18 carbon atoms and ii )yR
acrylic acid; mercaptoalkyl-carrying polysiloxanes;
and bis(thiol)polytetrahydrofurans. 1
N
2. A process for the preparation of a copolymer as claimed
in claim 1, which comprises copolymerizing \
CHZCHZ
(a) from 20 to 95% by weight of a l-vinylimidazole of the where R is H, CH3 or CZH5 and n is from 1 to 3, a mixture
formula I, a mixture of T a 1"dnylimidalole which thereof or a mixture of lvinylpyrrolidone or l-vinylimida
contains up to 20% by weight of other monoethyleni- zoles of the formulaI which contains up to 20% by weight
cally unsaturated monomers and of other monoethylenically unsaturated monomers, and
(b) from 5 to 80% by weight of water-insoluble polymers (b) from 5 to 80% by weight of water-insoluble polymers
selected from the group consisting of unsaturated poly selected from the group consisting of unsaturated poly
esters, homopolymers of butadiene, copolymers of 20 esters; homopolymers of butadiene; copolymers of
butadiene with styrene, acrylonitn'le, acrylates of alco butadiene with styrene, acrylonitrile, acrylates of alco
hols of l to 8 carbon atoms, isoprene, vinyl ethers hols of l to 8 carbon atoms, isoprene, vinyl ethers
where the alkyl chain is of l to 18 carbon atoms and where the alkyl chain is of 1 to 18 carbon atoms and
acrylic acid; mercaptoalkyl-carrying polysiloxanes and acrylic acid; mercaptoalkyl-canying polysiloxanes;
bis(thiol)polytetrahydrofurans 25
and bis (thiol) polytetrahydrofurans, which contain at
in water, an alcohol, an ester or a ketone, each having a least one ethylenically unsaturated double bond or one
boiling point below 135 C., or a mixture of the stated mercapto group in the molecule.
solvents, in the presence of free radical initiators and in the
presence or absence of protective colloids and surfactants.