US 4,785,102 AGranted

Photolytically cleavable, N-acylated sterically hindered amines

AssigneeCiba-Geigy Corporation

InventorsGodwin Berner, Mario Slongo

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Abstract

Sterically hindered cyclic amines which are substituted by a photoactivatable acyl group at the basic nitrogen atom can be deacylated by irradiation with UV light. This is advantageous if the basicity of the amines proves troublesome during application. Examples of such photoactivatable acyl groups are phenylglyoxyl, phenylacetyl or naphthylacetyl groups.

Claims5

Dependent claims

A compound of formula I ##STR14## wherein m is 1, 2 or 3,

A is a R.sup.1 --CO-- or R.sup.2 --CH.sub.2 -- group, wherein
R.sup.1 is phenyl or phenyl which is substituted by halogen, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy or hydroxy, or is naphthyl, C.sub.1 -C.sub.12 alkoxy, cyclohexyloxy, phenoxy or benzyloxy and, if m=1, may also be a radical B,
R.sup.2 is --CN, --P(O)(OR.sup.3).sub.2, CH.sub.3 CO-- or OR.sup.4, wherein
R.sup.3 is C.sub.1 -C.sub.4 alkyl or phenyl, and
R.sup.4 is phenyl or phenyl which is substituted by halogen or C.sub.1 -C.sub.4 alkyl, and
when m is 1,
B is a radical corresponding to the formulae ##STR15## wherein R.sup.5 is hydrogen, --OR.sup.8, ##STR16## --N(R.sup.10 R.sup.11), R.sup.6 is --OH or --OR.sup.12 and R.sup.7 is --OR.sup.12, --CN, --COOR.sup.13 or --CONH.sub.2, or R.sup.6 and R.sup.7 together are the oxo radical (.dbd.O), or R.sup.6 and R.sup.7, together with the C-atom to which they are attached, form an unsubstituted 2-spiro-1,3-dioxolane, 2-spiro-1,3-dioxane, 5-spiro-1,3-oxazolidine, 2-spiro-1,3-oxazolidine or 5-spiro-1,3-imidazolidine ring or said ring substituted by one or more identical or different members selected from C.sub.1 -C.sub.12 alkyl or the oxo radical,
R.sup.8 is C.sub.1 -C.sub.12 alkyl, benzyl, allyl or 2-cyanoethyl,
R.sup.9 is C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.12 alkenyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by halogen, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy or hydroxyl, or is C.sub.7 -C.sub.12 phenylalkyl, C.sub.1 -C.sub.4 alkoxy or phenoxy,
R.sup.10 is C.sub.1 -C.sub.12 alkyl, cyclohexyl, phenyl, naphthyl, or phenyl which is substituted by C.sub.1 -C.sub.4 alkyl,
R.sup.11 is C.sub.2 -C.sub.12 alkanoyl, C.sub.3 -C.sub.8 alkenoyl, benzoyl or a group of the formula ##STR17## wherein R.sup.14 and R.sup.15 are each independently of the other C.sub.1 -C.sub.8 alkoxy, phenoxy, or a group --N(R.sup.10)(R.sup.16), in which R.sup.16 is hydrogen or C.sub.1 -C.sub.12 alkyl,
R.sup.12 is C.sub.1 -C.sub.12 alkyl and R.sup.13 is C.sub.1 -C.sub.4 alkyl, and
Y is hydrogen, C.sub.1 -C.sub.12 alkyl, allyl or benzyl;
when m is 2,
B is a divalent radical corresponding to the formulae ##STR18## wherein Z is --O--, --NH-- or --NR.sup.10 --,
R.sup.17 is methylene, 1,2-ethylene, C.sub.3 -C.sub.20 polymethylene, or branched C.sub.3 -C.sub.20 alkylene, C.sub.2 -C.sub.10 alkenylene, 1,4-cyclohexylene, 1,3-cyclohexylene, cyclohexane-1,4-dimethylene, 1,3- or 1,4-phenylene, 1,4- or 1,5-naphthylene, 4,4'-diphenylene, diphenylmethane-4,4'-diyl, diphenyl oxide-4,4'-diyl or m- or p-xylene, or a radical --NH--R.sup.19 --NH--,
R.sup.18 is 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,2-butylene, 1,4-butylene, hexamethylene, 1,4-cyclohexylene or cyclohexane-1,4-dimethylene,
R.sup.19 is 1,2-ethylene, trimethylene, tetramethylene, hexamethylene, octamethylene, dodecamethylene, 2,2-dimethyltrimethylene, trimethyloctamethylene, 1,4-cyclohexylene, cyclohexane-1,4-dimethylene, 1,3-phenylene, 4,4'-diphenylene, diphenylmethane-4,4'-diyl, diphenyl oxide-4,4'-diyl, or m- or p-xylylene, and
R.sup.10 and R.sup.14 are as defined above;
and, when m is 3,
B is a trivalent radical corresponding to the formulae ##STR19## wherein R.sup.20 is propane-1,2-3-triyl, butane-1,2,4-triyl, benzene-1,3,5-triyl, benzene-1,2,4-triyl or naphthalene-1,4,5-triyl, R.sup.21 is a 1,3,5-triazin-2,4,6-triyl radical and Z is as defined above.

18 more elements

Dependencies are inferred from the claim text.

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Abstract

A compound of formula I ##STR14## wherein m is 1, 2 or 3,

A is a R.sup.1 --CO-- or R.sup.2 --CH.sub.2 -- group, wherein
R.sup.1 is phenyl or phenyl which is substituted by halogen, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy or hydroxy, or is naphthyl, C.sub.1 -C.sub.12 alkoxy, cyclohexyloxy, phenoxy or benzyloxy and, if m=1, may also be a radical B,
R.sup.2 is --CN, --P(O)(OR.sup.3).sub.2, CH.sub.3 CO-- or OR.sup.4, wherein
R.sup.3 is C.sub.1 -C.sub.4 alkyl or phenyl, and
R.sup.4 is phenyl or phenyl which is substituted by halogen or C.sub.1 -C.sub.4 alkyl, and
when m is 1,
B is a radical corresponding to the formulae ##STR15## wherein R.sup.5 is hydrogen, --OR.sup.8, ##STR16## --N(R.sup.10 R.sup.11), R.sup.6 is --OH or --OR.sup.12 and R.sup.7 is --OR.sup.12, --CN, --COOR.sup.13 or --CONH.sub.2, or R.sup.6 and R.sup.7 together are the oxo radical (.dbd.O), or R.sup.6 and R.sup.7, together with the C-atom to which they are attached, form an unsubstituted 2-spiro-1,3-dioxolane, 2-spiro-1,3-dioxane, 5-spiro-1,3-oxazolidine, 2-spiro-1,3-oxazolidine or 5-spiro-1,3-imidazolidine ring or said ring substituted by one or more identical or different members selected from C.sub.1 -C.sub.12 alkyl or the oxo radical,
R.sup.8 is C.sub.1 -C.sub.12 alkyl, benzyl, allyl or 2-cyanoethyl,
R.sup.9 is C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.12 alkenyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by halogen, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy or hydroxyl, or is C.sub.7 -C.sub.12 phenylalkyl, C.sub.1 -C.sub.4 alkoxy or phenoxy,
R.sup.10 is C.sub.1 -C.sub.12 alkyl, cyclohexyl, phenyl, naphthyl, or phenyl which is substituted by C.sub.1 -C.sub.4 alkyl,
R.sup.11 is C.sub.2 -C.sub.12 alkanoyl, C.sub.3 -C.sub.8 alkenoyl, benzoyl or a group of the formula ##STR17## wherein R.sup.14 and R.sup.15 are each independently of the other C.sub.1 -C.sub.8 alkoxy, phenoxy, or a group --N(R.sup.10)(R.sup.16), in which R.sup.16 is hydrogen or C.sub.1 -C.sub.12 alkyl,
R.sup.12 is C.sub.1 -C.sub.12 alkyl and R.sup.13 is C.sub.1 -C.sub.4 alkyl, and
Y is hydrogen, C.sub.1 -C.sub.12 alkyl, allyl or benzyl;
when m is 2,
B is a divalent radical corresponding to the formulae ##STR18## wherein Z is --O--, --NH-- or --NR.sup.10 --,
R.sup.17 is methylene, 1,2-ethylene, C.sub.3 -C.sub.20 polymethylene, or branched C.sub.3 -C.sub.20 alkylene, C.sub.2 -C.sub.10 alkenylene, 1,4-cyclohexylene, 1,3-cyclohexylene, cyclohexane-1,4-dimethylene, 1,3- or 1,4-phenylene, 1,4- or 1,5-naphthylene, 4,4'-diphenylene, diphenylmethane-4,4'-diyl, diphenyl oxide-4,4'-diyl or m- or p-xylene, or a radical --NH--R.sup.19 --NH--,
R.sup.18 is 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,2-butylene, 1,4-butylene, hexamethylene, 1,4-cyclohexylene or cyclohexane-1,4-dimethylene,
R.sup.19 is 1,2-ethylene, trimethylene, tetramethylene, hexamethylene, octamethylene, dodecamethylene, 2,2-dimethyltrimethylene, trimethyloctamethylene, 1,4-cyclohexylene, cyclohexane-1,4-dimethylene, 1,3-phenylene, 4,4'-diphenylene, diphenylmethane-4,4'-diyl, diphenyl oxide-4,4'-diyl, or m- or p-xylylene, and
R.sup.10 and R.sup.14 are as defined above;
and, when m is 3,
B is a trivalent radical corresponding to the formulae ##STR19## wherein R.sup.20 is propane-1,2-3-triyl, butane-1,2,4-triyl, benzene-1,3,5-triyl, benzene-1,2,4-triyl or naphthalene-1,4,5-triyl, R.sup.21 is a 1,3,5-triazin-2,4,6-triyl radical and Z is as defined above.

18 more elements