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US 4,086,204 AGranted
Novel polytriazine compounds
AssigneeChimosa Chimica Organica S.p.A.
InventorsPaolo Cassandrini, Antonio Tozzi
Life of this patent
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Abstract
Novel tetraalkyl piperidine radical containing polytriazine compounds are produced by reacting a dihalogen-triazine with a bifunctional compound containing amine, alcohol, mercaptan or phenol groups at least one of the bifunctional compounds containing a tetraalkyl piperidine radical. The compounds are valuable light stabilizers for synthetic polymers, particularly polyolefin in the form of fibers or films.
Claims28
A compound having the formula (I):
- ##STR28## wherein X, Y, Z, the same or different, is a member selected from --O--, --S--, ##STR29## R.sub.3 being a member selected from hydrogen, straight or branched chain C.sub.1 to C.sub.18 alkyl, C.sub.5 to C.sub.18 cycloalkyl, substituted or not substituted C.sub.6 to C.sub.18 aryl, C.sub.7 to C.sub.18 aralkyl, a piperidine radical of formula (II):
- ##STR30## wherein R.sub.4, R.sub.5, R.sub.7, R.sub.8, the same or different, are members selected from C.sub.1 to C.sub.6 alkyl, and R.sub.6 is selected from H, O, C.sub.1 to C.sub.18 straight or branched chain alkyl, C.sub.2 to C.sub.18 alkenyl or alkynyl, C.sub.7 to C.sub.18 aralkyl;
- R.sub.1 is selected from C.sub.2 to C.sub.18 straight or branched chain alkylene, C.sub.5 to C.sub.18 cycloalkylene, C.sub.6 to C.sub.18 arylene, C.sub.7 to C.sub.18 aralkylene;
- R.sub.2 is selected from hydrogen, chlorine, bromine, --OH, C.sub.1 to C.sub.18 straight or branched chain alkyl, C.sub.5 to C.sub.18 cycloalkyl, substituted or not substituted C.sub.6 to C.sub.18 aryl, C.sub.7 to C.sub.18 aralkyl, a piperidine radical of formula (II), a group ##STR31## wherein R.sub.11, R.sub.12 are selected from hydrogen or C.sub.1 to C.sub.12 alkyl, C.sub.5 to C.sub.12 cycloalkyl, C.sub.6 to C.sub.12 aryl, C.sub.7 to C.sub.12 aralkyl;
- m is an integer from 0 to 1;
- n is an integer from 2 to 200;
- A, b are the terminal groups, A being H or ##STR32## and B is halogen or --X--R.sub.1 --YH;
- or where --XR.sub.1 --Y-- represent a bivalent heterocyclic group having 6 to 8 nitrogen atoms with X and y each representing a disubstituted nitrogen atom;
- or where --X--R.sub.1 --Y-- represent a residue ##STR33## in which R.sub.9 and R.sub.10 are hydrogen, C.sub.1 to C.sub.12 alkyl, C.sub.5 to C.sub.12 cycloalkyl, C.sub.6 to C.sub.12 aryl, or C.sub.7 to C.sub.12 aralkyl;
- with the proviso that at least one of the radicals --X--R.sub.1 --Y-- and --(Z).sub.m --R.sub.2 contains a piperidine radical of formula (II).
7 more elements
A method of producing a compound having the general formula (I):
- ##STR45## wherein X, Y, Z, the same or different, is a member selected from --O--, --S--, ##STR46## R.sub.3 being a member selected from hydrogen, straight or branched chain C.sub.1 to C.sub.18 alkyl, C.sub.5 to C.sub.18 cycloalkyl, substituted or not substituted C.sub.6 to C.sub.18 aryl, C.sub.7 to C.sub.18 aralkyl, a piperidine radical of formula (II):
- ##STR47## wherein R.sub.4, R.sub.5, R.sub.7, R.sub.8, the same or different, are members selected from C.sub.1 to C.sub.6 alkyl, and R.sub.6 is selected from H, O, C.sub.1 to C.sub.18 straight or branched chain alkyl, C.sub.2 to C.sub.18 alkenyl or alkynyl, C.sub.7 to C.sub.18 aralkyl;
- R.sub.1 is selected from C.sub.2 to C.sub.18 straight or branched chain alkylene, C.sub.5 to C.sub.18 cycloalkylene, C.sub.6 to C.sub.18 arylene, C.sub.7 to C.sub.18 aralkylene;
- R.sub.2 is selected from hydrogen, chlorine, bromine, -OH C.sub.1 to C.sub.18 straight or branched chain alkyl, C.sub.5 to C.sub.18 cycloalkyl, substituted or not substituted C.sub.6 to C.sub.18 aryl, C.sub.7 to C.sub.18 aralkyl, a piperidine radical of formula (II), a group ##STR48## wherein R.sub.11, R.sub.12 are selected from hydrogen or C.sub.1 to C.sub.12 alkyl, C.sub.5 to C.sub.12 cycloalkyl, C.sub.6 to C.sub.12 aryl, C.sub.7 to C.sub.12 aralkyl;
- m is an integer from 0 to 1;
- n is an integer from 2 to 200;
- A, b are the terminal groups, A being H or ##STR49## and B is halogen or --X--R.sub.1 --YH;
- in formula (I) there is the condition that at least one of the radicals --X--R.sub.1 --Y-- and --(Z).sub.m --R.sub.2 contains a piperidine radical of formula (II), comprising reacting a compound of formula (IV):
- hx -- r.sub.1 -- yh (iv)
- x, y, r.sub.1 having the meaning as previously defined, with a member of the group consisting of
- (a) 2,4-dihalogentriazines of formula (III) ##STR50## and (b) cyanuric halide
- in solution in inert solvent, at a temperature from -10.degree. C to the solvent boiling temperature, in the presence of an organic or inorganic base.
9 more elements
A method of increasing the light stability of a synthetic polymer, comprising adding to a composition of material of said synthetic polymer, an amount of a compound having the formula (I):
- ##STR55## wherein X, Y, Z, the same or different, is a member selected from --O--, --S--, ##STR56## R.sub.3 being a member selected from hydrogen, straight or branched chain C.sub.1 to C.sub.18 alkyl, C.sub.5 to C.sub.18 cycloalkyl, substituted or not substituted C.sub.6 to C.sub.18 aryl, C.sub.7 to C.sub.18 aralkyl, a piperidine radical of formula (II):
- ##STR57## wherein R.sub.4, R.sub.5, R.sub.7, R.sub.8, the same or different, are members selected from C.sub.1 to C.sub.6 alkyl, and R.sub.6 is selected from H, O, C.sub.1 to C.sub.18 straight or branched chain alkyl, C.sub.2 to C.sub.18 alkenyl or alkynyl, C.sub.7 to C.sub.18 aralkyl;
- R.sub.1 is selected from C.sub.2 to C.sub.18 straight or branched chain alkylene, C.sub.5 to C.sub.18 cycloalkylene, C.sub.6 to C.sub.18 arylene, C.sub.7 to C.sub.18 aralkylene;
- R.sub.2 is selected from hydrogen, chlorine, bromine, --OH, C.sub.1 to C.sub.18 straight or branched chain alkyl, C.sub.5 to C.sub.18 cycloalkyl, substituted or not substituted C.sub.6 to C.sub.18 aryl, C.sub.7 to C.sub.18 aralkyl, a piperidine radical of formula (II), a group ##STR58## wherein R.sub.11, R.sub.12 are selected from hydrogen or C.sub.1 to C.sub.12 alkyl, C.sub.5 to C.sub.12 cycloalkyl, C.sub.6 to C.sub.12 aryl, C.sub.7 to C.sub.12 aralkyl;
- m is an integer from 0 to 1;
- n is an integer from 2 to 200;
- A, b are the terminal groups, A being H or ##STR59## and B is halogen or --X--R.sub.1 --YH;
- in formula (I) ruling the condition that at least one of the radicals --X--R.sub.1 --Y-- and --(Z).sub.m --R.sub.2 contains a piperidine radical of formula (II), effective to increase the light stability of said synthetic polymer.
5 more elements
Dependencies are inferred from the claim text.