Compositions – Compositions containing a single chemical reactant or plural... – Organic reactant
Patent
1992-03-03
1994-02-15
Albrecht, Dennis
Compositions
Compositions containing a single chemical reactant or plural...
Organic reactant
8111, 252 98, 252 99, 2521864, 25230126, 252524, 252543, 544 92, 562 2, C07D26522, C11D 3395, D06L 302, D06L 312
Patent
active
052864014
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to the use of heterocyclic compounds of the general formula I ##STR2## where the variables have the following meanings: X is O, S or the group N--R.sup.3, where R.sup.3 hydrogen, C.sub.1 -C.sub.25 -alkyll C.sub.1 -C.sub.25 -acyl or an aryl group of up to 12 carbon atoms, C.sub.2 -C.sub.25 -alkene group or a phenyl radical which may be additionally substituted by one or two C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, hydroxyl, carboxyl, sulfo, amino, C.sub.1 -C.sub.4 -acylamino, nitro or cyano groups or chlorine or bromine atoms, which substituents, if there are two of them, may be identical or different, m-methoxyphenyl or m-methylsulfonylphenyl, C.sub.1 -C.sub.4 -alkoxy, hydroxyl, carboxyl, sulfo, amino or C.sub.1 -C.sub.4 -acylamino group or a chlorine or bromine atom, and
The present invention also relates to washing and cleaning agents which contain compounds I.
In EP-B 099 197 (1) and EP-B 240 057 (2) customary bleach activators mentioned for washing and cleaning agents include acylated amines such as tetraacetylethylenediamine (TAED), acylated sugars such as pentaacetylglucose, carboxylic esters such as sodium p-acetoxybenzenesulfonate and a number of acylated heterocyclic compounds, namely hydantoins, cyclic hydrazides, triazoles, urazoles, imidazolines, glycolurils, piperazines and cyclic ureas.
U.S. application No. 3 822 114 (3) describes aldehyde and ketone compounds for use as bleach activators. The examples mentioned therein of heterocyclic ketones include piperidine derivatives and also tetrahydrothiopyranone and 4-oxacyclohexanone derivatives.
J. Org. Chem. 14 (1949), 967-81, (4), describes the preparation of benz-(4H)1,3-oxazin-4-one and 2-substituted derivatives. The substituents mentioned are methyl, ethyl, n-propyl, phenyl, o- and p-tolyl, o- and p-chlorophenyl, o- and p-nitrophenyl and also 3-pyridyl. Nothing is said about application properties of these compounds.
EP-A-332 294 (5) relates to washing agent compositions which contain inter alia benz-(4H)1,3-oxazin-4-ones of the formula I (X=O, Y=CH, R.sup.2 =H) as bleach activators, where R.sup.1 is hydrogen, alkyl, alkaryl, aryl, aralkyl, alkoxy, haloalkyl, amino, aminoalkyl, carboxyl or a carboxyl-containing group. The Description and the Examples mention without exception only compounds where R.sup.1 is alkyl, in particular methyl, amino, aminoalkyl, acyl, alkoxy, haloalkyl, alkoxyalkyleneoxy or alkylenecarboxylate.
The prior art bleach activators have been found to be in need of improvement. Especially the amount needed of these agents in washing and cleaning agents to obtain an adequate effect is frequently too high.
It is an object of the present invention to provide bleach activators which if used in a smaller amount produce the same effect as the prior art agents.
We have found that this object is achieved by using for this purpose the heterocyclic compounds I mentioned at the beginning.
The compounds I to be used according to the present invention belong for the case Y=CH to the substance classes of the benz-(4H)1,3-oxazin-4-ones (X=O), benz-(4H)1,3-thiazin-4-ones (X=S) and (4H)1,3-quinazolin-4-ones (X=N--R.sup.3 or to the corresponding pyridofused compounds (Y=N).
In a preferred embodiment, use is made of benz-(4H)1,3-oxazin-4-one derivatives (Y=CH) where R.sup.1 is as defined for the case X=O. Particular preference is given to the use of 2-(p-tolyl)-, 2-(p-chlorophenyl)-, 2-(m-nitrophenyl)-, 2-(p-methylsulfonylphenyl)- and in particular 2-phenyl-benz-(4H)1,3-oxazin-4-one.
In a further preferred embodiment, use is made of benz-(4H)1,3-thiazin-4-one (Y=CH) and (4H)1,3-quinazo-lin-4-one (Y=CH) and also of their derivatives where R.sup.1 and R.sup.2 are each as defined for the case X=S or N--R.sup.3.
Suitable R.sup.3 is C.sub.1 -C.sub.25 -allcyl, preferably C.sub.1 -C.sub.10 -alkyl, eg. methyl, ethyl, n-propyl, n-butyl, 2-ethylhexyl or isononyl, C.sub.1 -C.sub.25 -acyl, preferably C.sub.1 -C.sub.10 -acyl, eg. formyl, acetyl, propionyl, butyryl or octanoyl, or aryl of up to 12 carbon atoms such a
REFERENCES:
patent: 3822114 (1974-07-01), Montgomery
patent: 4966723 (1990-10-01), Hodge
Journal Organism Chemical, vol. 14, David T. Zentmyer, et al. "The So-Called Acylanthranils (3,1,4-benzoxazones). I. Preparation; Reactions with Water, Ammonia, and Aniline; Structure", pp. 367-381 (1949).
Dung Bernhard
Hahn Erwin
Oftring Alfred
Perner Johannes
Trieselt Wolfgang
Albrecht Dennis
BASF - Aktiengesellschaft
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