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US 4,055,431 AGranted
N(.beta.-chloro-propionyl or acryloyl)carbamyl or ureido piperazines
AssigneeCiba-Geigy Corporation
InventorsRolf Kyburz, Rainer Kitzing
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AssigneeCiba-Geigy Corporation
InventorsRolf Kyburz, Rainer Kitzing
Estimating the term…
This invention relates to new compounds of the formula ##STR1## m is 1 or 2, n is 2, 3, 4, 5 or 6, Z represents a polyamine radical containing a basic tertiary or a quaternary nitrogen atom. The compounds of formula (m) an useful as crosslinking agents. They are particularly useful for crosslinking gelatine, preferably gelatin present in layers of photographic material.
An acylurea compound which corresponds to the formula ##STR28## wherein m is 1 or 2, p and q each denote one of the numbers 1 and 2 and A.sub.4 and A.sub.5 denote alkylene radicals with 1 to 4 carbon atoms.
Process for crosslinking hydrophilic colloids which contain amino, imino and/or hydroxyl groups, which comprises using as a crosslinking agent a
A hydrophilic colloid crosslinked by means of an acylurea compound as
Dependencies are inferred from the claim text.
From the US filing history. Foreign family members aren’t listed.
By radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof: radicals derived from nitrogen analogues of carbonic acid
Y being a hydrogen or a carbon atom: y being a hydrogen or an acyclic carbon atom
With the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings:…
With non-macromolecular additives: hardeners
Term ended 25 Oct 1994 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
The subject of the invention are new acylurea compounds of the formula ##STR2## wherein m is 1 or 2, n denotes an integer of value from 2 to 6 and Z denotes the radical of a polyamine which is bonded by nitrogen atoms to the --CO--NH--CO-- groups and in addition to these nitrogen atoms contains at least one tertiary or quaternary nitrogen atom.
If m is 2, the compounds contain .beta.-chloropropionic acid radicals (ClH.sub.2 C--CH.sub.2 --CO--). Particularly valuable compounds are in general, those with two acrylic acid radicals (H.sub.2 C=CH--CO--), that is to say the compounds of the formula (1), wherein m is 1.
The polyamine from which the radical Z is derived possesses n at most secondary (that is to say primary and/or secondary) amino groups, which are then bonded to the acyl groups in the acyl urea compounds of the formula (1): ##STR3##
143.0 g (1.065 mol) of freshly distilled 3-chloropropionyl isocyanate in 1 l of absolute toluene are first introduced into a 2 l reaction vessel equipped with a stirrer, thermometer and dropping funnel. The mixture is cooled to -5.degree. C and a solution of 72.5 g (0.5 mol) of freshly distilled N,N'-bis-(3-amino-propyl)methylamine in 200 ml of absolute toluene is added dropwise. Hereupon, the reaction product separates out as a white precipitate. After completion of the addition, the mixture is allowed to warm to room temperature and is then left for a further 11/2 hours whilst stirring. The product is then filtered off and rinsed with 50 ml of toluene and 50 ml of ether, and dried in a vacuum cabinet at up to 40.degree. C. 208.2 g of the chloropropionyl-urea compound of the formula ##STR9## of melting point: 95.degree. C (with decomposition) are obtained in quantitative yield.
In the same way, reaction of 6.5 g (50 mmols) of N-(2-aminoethyl)piperazine with 14.3 g (106 mmols) of 3-chloropropionyl isocyanate gives a quantitative yield of 19.8 g of the 3-chloropropionyl urea of the formula ##STR10## Melting point: 125.degree.-130.degree. C.
In the same way as in Example 1, reaction of 10.0 g (50 mmols) of N,N'-bis(3-aminopropyl)piperazine with 14.3 g (106 mmols) of 3-chloropropionyl isocyanate gives 24.0 g of the 3-chloropropionylurea compound of the formula ##STR11##