Ciba-Geigy Ag

Ciba-Geigy Corporation

Frederick H Howell

Josef Pfeifer

Jurgen Finter

Visvanathan Ramanathan

Rudolf Duthaler

Konrad Oertle

Anthraquinones having .alpha.,.alpha.-(dialkyl)alkyl groups which are functionally substituted, for example by --COOH or --CONH--NH.sub.2, are described. Compositions which contain such anthraquinones, an aminoalcohol and an epoxy resin with or without a hardener are suitable for preparing metallic coatings and images on the cured composition by exposure to light and currentless metal deposition.

Substituted anthraquinones and use thereof in epoxy resins

New phenols are described containing an alkyl substituent containing a functional group; as well as a process for the production of such phenols. The new phenols are useful e.g. as stabilizers in organic or aqueous systems.

Phenols and their production

New hydroquinones have the formula: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2; R is a residue of formula: ##STR2## wherein Q is (i) -OX or (ii) -PO(OR.sub.11)((O).sub.x R.sub.11); and salts thereof with organic or inorganic acid bases. The groups X and R.sub.11 and x are defined hereinafter. The compounds of formula I are useful as stabilisers in photographic materials.

Hydroquinones

Aminocyclohexyl-substituted, branch alkylamines

New compounds having the formula I are described: ##STR1## wherein R and R.sup.1, independently are H, halogen, a straight- or branched-chain alkyl having 1 to 8 carbon atoms or a residue having the formula II: ##STR2## wherein R.sup.2 and R.sup.3 are the same or different and each is H or straight- or branched-chain alkyl having 1 to 4 carbon atoms and R.sup.4 is H, halogen or straight- or branched-chain alkyl having 1 to 4 carbon atoms; provided that at least one of R and R.sup.1 is a residue of formula II, and that when R is a residue of formula II wherein R.sup.2, R.sup.3, and R.sup.4 and H, R.sup.1 may not be ethyl or n-propyl. Processes for producing the new compounds are also disclosed. Compounds of formula I are useful as intermediates for valuable dispersion dyestuffs.

Ortho nitroanilines and a process for their production

New compounds having the formula 1 ##STR1## wherein W is hydrogen, halogen, n-alkyl, --NHCOR.sup.1, --COR.sup.1, or phenoxyacetylamino optionally substituted by one or two C.sub.1-12 straight- or branched chain alkyl, X is a substituent in the coupling position and is selected from hydrogen, chlorine, bromine, --SR.sup.11 or a nitrogen-containing heterocyclic residue attached at a ring nitrogen atom, and Y is a group having the formula 2 ##STR2## wherein Q is selected from the residues: --COOR.sup.4 or --CONR.sup.4 R.sup.5, --OM, --NR.sup.7 R.sup.8, --PO(OR.sup.9)[O].sub.x R.sup.10 with X=0 or 1, --SO.sub.2 OH, --SO.sub.2 NR.sup.4 R.sup.5 or CN. The groups R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, M, k and n are defined hereinafter. These compounds are used as black color couplers in photographic materials.

Resorcinol compounds

New aminoalkyl anilines having the formula: ##STR1## wherein k is 0 or 1; QNH.sub.2 is a residue of formula ##STR2## which is situated in one of the positions of the benzene ring ortho or para to the amino group and wherein n is an integer from 1 to 15, R.sub.1 is C.sub.1 -C.sub.8 alkyl, R.sub.2 is C.sub.1 -C.sub.4 alkyl or R.sub.1 and R.sub.2, together with the carbon atom to which they are attached, form a C.sub.5 -C.sub.8 cycloalkylene residue, R.sub.3 is H or C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl, or C.sub.6 -C.sub.10 aryl; and R.sub.4 and R.sub.5 are H or C.sub.1 -C.sub.4 alkyl; as well as the corresponding salts of compounds of formula I with organic or inorganic acids and metal salt complexes; process for their production; and their use as intermediates for polyamides.

New diamines and a process for their production

New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification. The new compounds are useful e.g. as stabilizers in photographic material.

Hydroquinone ether compounds

New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and Q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification, The new compounds are useful e.g. as stabilizers in photographic material.

New benzo-1,4-quinones and salts thereof with organic or inorganic acid and bases have the formula I ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## wherein Q is selected from the residues --CO.sub.2 R.sub.4, --CON(R.sub.4)(R.sub.5), --OR.sub.5, --OCOR.sub.7, --N(R.sub.8)(R.sub.9), --PO(OR.sub.10)([O].sub.x R.sub.11), --SO.sub.2 R.sub.12, --CN, Halogen, --NO.sub.2 or --COR.sub.13, n is an integer from 1 to 20, k is 1 or 2 and x is 0 or 1, and R.sub.1 to R.sub.5 and R.sub.7 to R.sub.13 are as defined in the specification. The compounds of formula I are useful in photographic materials such as bleaching inhibitors in films of photographic silver dye bleach materials.

Benzo-1,4-quinones

Aminoalkyl aromatic compounds and their production

New hydroquinones having the formula: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2; R is a residue of formula: ##STR2## wherein Q is selected from the residues --COZR.sub.4 wherein Z is 0 or NR.sub.5, --OX wherein X is R.sub.5 or --COR.sub.7, --NR.sub.8 R.sub.9, --PO(OR.sub.10)[O].sub.x R.sub.11 wherein x is 0 or 1, --SO.sub.2 R.sub.12 or --CN, and salts thereof with organic or inorganic acid bases. The groups, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, k and n are defined hereafter. These compounds are used as stabilizers in photographic materials.

Compounds having the formula I ##STR1## as well as salts or metal salt complexes thereof, in which formula I n, R.sub.1, R.sub.2 and Z have the meanings given in claim 1, can be prepared under mild reaction conditions by reacting 1.0 mole of an aromatic amine having the formula II ##STR2## with up to three moles of an alkylating agent (III) capable of introducing a residue Z into the benzene ring of an amine (II) at a position ortho or para to the NH.sub.2 group, the reaction being effected at elevated temperature in the presence of an acid catalyst in an aqueous acid medium, containing at least 30% by weight of water, based on the acid, and optionally converting compounds (I) into salts or metal salt complexes. The compounds (I) so produced are useful in the production of intermediates for dyestuffs, additives for plastics, rubbers, oils, etc., and in the production of biologically active compounds.

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Atherton, United Kingdom

Frederick H Howell