Benzophenone ether esters, processes for their preparation, and

Details Benzophenone ether esters, processes for their preparation, and Benzophenone ether esters, processes for their preparation, and

1992-03-13

1993-09-14

Clingman, A. Lionel

Bleaching and dyeing; fluid treatment and chemical modification

Color protecting process for dyed product

8490, 8524, 8527, 8607, 8609, 8610, 8922, C07C 6914, C07C 6954, C07C 6978, D06P 164

Patent

active

052444767

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to benzophenone ether esters, processes for their preparation, their use for improving the light stability of polyester dyeings and a dyeing process and dye preparations.
A process for improving the light fastness of polyester dyeings, in which alkyl ethers of 2,2',4,4'-tetrahydroxybenzophenone are used, has already been described in DE-AS 11 56 760. However, this process has a number of disadvantages. Thus, in the case of bright dyeings, the hue is shifted and the brilliance is reduced to a greater or lesser degree. The dyes do not show sufficiently good exhaustion onto the fiber, resulting in wastewater problems. Furthermore, the benzophenone derivatives described there have a tendency to migrate during the customary exposure to dry heat setting.
Processes for improving the light fastness of polyester dyeings using certain benzophenone ether esters have also already been disclosed in EP-A 254 987 and EP-A 309 909.
Furthermore, benzophenone ether esters which are used for protecting plastics, such as, for example, polyacrylic esters, polymethacrylic esters, polystyrene and ABS polymers, against the effect of UV light are disclosed in EP 182 056.
The object of the present invention is to provide compounds which lead to an improvement in the light fastness of dyeings on polyester materials, without reduction in the exhaustion of the dye onto the fiber and the depth of shade and brilliance of the dyeing.
Surprisingly, this object is achieved by compounds of the general formula I ##STR2## in which R.sup.1 and R.sup.4, independently of one another, are (C.sub.1 -C.sub.6)-alkyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or hydrogen; -C.sub.6)-alkyl or hydrogen; -C.sub.8)-cycloalkyl; (C.sub.1 -C.sub.12)-alkyl or (C.sub.3 -C.sub.8)-cycloalkyl, each of which is substituted by (C.sub.1 -C.sub.6)-alkoxy, (C.sub.2 -C.sub.7)-alkoxycarbonyl, amino, (C.sub.1 -C.sub.6)-alkylamino, di-(C.sub.1 -C.sub.6)-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or nitro; phenyl or phenyl substituted by (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-alkoxy, (C.sub.2 -C.sub.7)-alkoxycarbonyl, amino, (C.sub.1 -C.sub.6)-alkylamino, di-(C.sub.1 -C.sub.6)-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or nitro.
The alkyl, alkoxy, alkoxycarbonyl, alkylamino and dialkylamino radicals can be straight-chain or branched.
The radicals R.sup.1 and R.sup.4 can be in the ortho, meta or para position relative to the carbonyl group. Where x or y is 2, the substituents can be in the 1,2-, 1,3- or 1,4-position relative to one another.
The radicals R.sup.2 and R.sup.3 can be bound to all three free positions of the six-membered ring.
Preference is given to compounds of the general formula I in which -C.sub.3)-alkyl, cyano, chlorine or trifluoromethyl, -C.sub.3)-alkyl, -C.sub.4)-alkyl, cyclopentyl or cyclohexyl, each of which is substituted by (C.sub.1 -C.sub.4)-alkoxy, (C.sub.2 -C.sub.5)-alkoxycarbonyl, amino, (C.sub.1 -C.sub.4)-alkylamino, di-(C.sub.1 -C.sub.4)-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or nitro; phenyl or phenyl which is substituted by (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.2 -C.sub.5)-alkoxycarbonyl, amino, (C.sub.1 -C.sub.14)-alkylamino, di-(C.sub.1 -C.sub.4)-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or nitro.
Particular preference is given to compounds of the general formula I in which
The compounds according to the invention of the general formula I can be prepared by reacting a compound of the general formula II ##STR3## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, x and y are as defined above, with a compound of the general formula III ##STR4## in which X represents hydroxyl, halogen, (C.sub.1 -C.sub.4)-alkoxy or --OCOR.sup.5 and R.sup.5 is as defined above.
The reaction is advantageously carried out at temperatures of 0.degree. to 150.degree. C., particularly preferably at 50.degree. to 120.degree. C.
Preferably, the reaction is carried out in an inert or

REFERENCES:
patent: 4789382 (1988-12-01), Neumann et al.
patent: 4824892 (1989-04-01), Eiglmeier et al.
patent: 4911732 (1990-03-01), Neumann et al.

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