Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1999-02-05
2000-11-28
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
5483141, 8189, C07D40312, D06M 13322
Patent
active
061537624
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to bridged methylolated bis-4,5-dihydroxyimidazolidin-2-ones, conforming to the formula 1 ##STR2## where X=(CH.sub.2).sub.n where n=2, 3, 4, 5, 7, 8, 9 or 10, branched or cyclic alkyl, each with or without hetero atoms such as O, CH.sub.2), CH.sub.2).sub.m, OCH.sub.2 CH.sub.2 CH.sub.2, to their use in textile finishing, especially on cellulosics.
2. Description of the Background
4,5-Dihydroxy-1,3-dimethylolimidazolidin-2-ones are used as formaldehydic crosslinkers in textile finishing. They impart good crease recovery and reduce textile shrinkage. However, the strength of the fabric is greatly impaired. In addition, the use of these substances on textiles leads to elevated formaldehyde values, which are no longer acceptable to most users for ecotoxicological reasons.
Food chemists use certain crosslinkers to control the gas permeability of cellophane. The compounds of the general formula 1 where X=(CH.sub.2).sub.6 and (CH.sub.2).sub.12 are described by H. Niebergall and H. Seitz in Angew. Makromolekulare Chem. 21 (1972) 41-51; ibid 113 to 128; and ibid 129 to 142. These compounds are, as stated, suitable for crosslinking cellophane and especially for controlling the gas permeability. They are prepared in a two-stage process in which the corresponding bridged urea derivative and glycol are first reacted to prepare the corresponding bridged imidazolidin-2-one. In the second stage, the bridged imidazolidin-2-one is reacted with formaldehyde to form the corresponding hydroxymethylated compound. Nowhere in the literature is there any mention of the use of these known compounds in textile finishing.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide textile crosslinkers which provide good crease recovery and shrinkage reduction without significantly impairing the strength of the fabric. In addition, their use on textiles shall not raise the formaldehyde value to an ecologically unsafe level.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
We have found that this object is achieved by bridged, if appropriate methylolated bis-4,5-dihydroxyimidazolidin-2-ones conforming to the formula 1 N, P in the alkyl chain, CH.sub.2 CH.sub.2).sub.m, OCH.sub.2 CH.sub.2 CH.sub.2,
This invention accordingly provides bridged, if approriate methylolated bis-4,5-dihydroxyimidazolidin-2-ones of the formula 1, a two-stage process for their preparation, a one-stage process for preparing the bridged methylolated bis-4,5-dihydroxyimidazolidin-2-ones of the formula 1, including the compound where X=(CH.sub.2).sub.6, and generally also for the use of these bridged methylolated bis-4,5-dihy-droxyimidazolidin-2-ones, including those where X=(CH.sub.2).sub.6, in textile finishing.
Fabrics treated in this way are preferred because of their enhanced tensile strength in particular.
Surprisingly, the formaldehyde content on the fabric is distinctly lower than expected.
The novel process for preparing the bridged, if appropriate methylolated bis-4,5-dihydroxyimidazolidin-2-ones has a two-stage and a one-stage version.
The two-stage version is described in the below-presented chemical reaction equations: ##STR3## with R.sup.1, R.sup.2 =H and/or CH.sub.2 OH.
The bridged ureas of the above-presented formula (2) are reacted with glyoxal at from 30.degree. C. to 70.degree. C. in the presence of bases, acids or salts thereof to prepare the compounds of the formula (3). This reaction is preferably carried out with a pH of from 4 to 8 for the solutions. The compounds of the formula (3) are then reacted with formaldehyde at from 30.degree. C. to 700.degree. C. and at from pH 4 to 9 to form the desired bridged methylolated bis-4,5-dihydroxyimidazolidin-2-ones in the second step of the process.
Surprisingly, the bridged methylolated bis-4,5-dihydroxyimidazolidin-2-ones can alternatively also be prepared directly from the same reagents in a single-step process as per the following equation 2: ##STR4##
In the direct, single-stage preparation of
REFERENCES:
patent: 3652583 (1972-03-01), Tajima et al.
patent: 3890095 (1975-06-01), Bann et al.
patent: 4284536 (1981-08-01), Bezwada
patent: 4298747 (1981-11-01), Frick et al.
patent: 4306872 (1981-12-01), Herbes et al.
Niebergall et al, Chemical Abstracts, vol. 78, #5 44433h and 44433j, 1973.
Hois Pia
Reichert Jurgen
BASF - Aktiengesellschaft
Higel Floyd D.
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