US4086204A
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Novel polytriazine compounds
Assignee: Novartis Corp
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Filing: 1976-06-23
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Granted: 1978-04-25
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Expires: 1996-06-23
Abstract
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.
Inventors
- 👤 Paolo Cassandrini
- 👤 Antonio Tozzi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 21:56
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/02; C08G73/0273; C07; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/26; C08G73/06; C08G73/0622; C08G73/0638; C08G73/0644; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3477; C08K5/3492
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
376 words
A compound having the formula (I): ##STR28## wherein X, Y, Z, the same or different, is a member selected from --O--, --S--, ##STR29## R 3 being a member selected from hydrogen, straight or branched chain C 1 to C 18 alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II): ##STR30## wherein R 4 , R 5 , R 7 , R 8 , the same or different, are members selected from C 1 to C 6 alkyl, and R 6 is selected from H, O, C 1 to C 18 straight or branched chain alkyl, C 2 to C 18 alkenyl or alkynyl, C 7 to C 18 aralkyl; R 1 is selected from C 2 to C 18 straight or branched chain alkylene, C 5 to C 18 cycloalkylene, C 6 to C 18 arylene, C 7 to C 18 aralkylene; R 2 is selected from hydrogen, chlorine, bromine, --OH, C 1 to C 18 straight or branched chain alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II), a group ##STR31## wherein R 11 , R 12 are selected from hydrogen or C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl, C 6 to C 12 aryl, C 7 to C 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 1 --YH; or where --XR 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 1 --Y-- represent a residue ##STR33## in which R 9 and R 10 are hydrogen, C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl, C 6 to C 12 aryl, or C 7 to C 12 aralkyl; with the proviso that at least one of the radicals --X--R 1 --Y-- and --(Z) m --R 2 contains a piperidine radical of formula (II).
Claim 2
Dependent Claim
376 words
A compound having the formula (I): ##STR28## wherein X, Y, Z, the same or different, is a member selected from --O--, --S--, ##STR29## R 3 being a member selected from hydrogen, straight or branched chain C 1 to C 18 alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II): ##STR30## wherein R 4 , R 5 , R 7 , R 8 , the same or different, are members selected from C 1 to C 6 alkyl, and R 6 is selected from H, O, C 1 to C 18 straight or branched chain alkyl, C 2 to C 18 alkenyl or alkynyl, C 7 to C 18 aralkyl; R 1 is selected from C 2 to C 18 straight or branched chain alkylene, C 5 to C 18 cycloalkylene, C 6 to C 18 arylene, C 7 to C 18 aralkylene; R 2 is selected from hydrogen, chlorine, bromine, --OH, C 1 to C 18 straight or branched chain alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II), a group ##STR31## wherein R 11 , R 12 are selected from hydrogen or C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl, C 6 to C 12 aryl, C 7 to C 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 1 --YH; or where --XR 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 1 --Y-- represent a residue ##STR33## in which R 9 and R 10 are hydrogen, C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl, C 6 to C 12 aryl, or C 7 to C 12 aralkyl; with the proviso that at least one of the radicals --X--R 1 --Y-- and --(Z) m --R 2 contains a piperidine radical of formula (II).
Claim 3
Dependent Claim
315 words
A compound according to claim 1 having the formula (I): ##STR34## wherein X, Y, Z, the same or different, is a member selected from --O--, --S--, ##STR35## R 3 being a member selected from hydrogen, straight or branched chain C 1 to C 18 alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II): ##STR36## wherein R 4 , R 5 , R 7 , R 8 , the same or different, are members selected from C 1 to C 6 alkyl, and R 6 is selected from H, O, C 1 to C 18 straight or branched chain alkyl, C 2 to C 18 alkenyl or alkynyl, C 7 to C 18 aralkyl; R 1 is selected from C 2 to C 18 straight or branched chain alkylene, C 5 to C 18 cycloalkylene, C 6 to C 18 arylene, C 7 to C 18 aralkylene; R 2 is selected from hydrogen, chlorine, bromine, -OH, C 1 to C 18 straight or branched chain alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of form-1a (II), a group ##STR37## wherein R 11 , R 12 are selected from hydrogen or C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl, C 6 to C 12 aryl, C 7 to C 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 ##STR38## and B is halogen or --X--R 1 --YH; in formula (I) the condition there is that at least one of the radicals --X--R 1 --Y-- and --(Z) m --R 2 contains a piperidine radical of formula (II).
Claim 4
Dependent Claim
36 words
A compound according to claim 2, wherein --X--R 1 --Y-- represents a bivalent radical of a heterocyclic compound having 6 to 8 members, containing 2 nitrogen atoms, X and Y each representing a disubstituted nitrogen atom.
Claim 5
Dependent Claim
57 words
A compound according to claim 2, wherein the group --X--R 1 --Y-- represents a residue ##STR39## in which R 9 and R 10 , the same or different are members selected from hydrogen, C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl, C 6 to C 12 aryl, C 7 to C 12 aralkyl.
Claim 6
Dependent Claim
23 words
A compound according to claim 2, wherein m is one and the radical R 2 --Z-- is the same as --X--R 1 --YH.
Claim 7
Dependent Claim
30 words
A compound according to claim 2, wherein R 3 is selected from hydrogen, C 1 to C 12 straight or branched chain alkyl, and a piperidine radical of formula (II).
Claim 8
Dependent Claim
30 words
A compound according to claim 2, wherein R 1 is selected from straight or branched chain C 2 to C 10 , alkylene, and C 6 to C 10 arylene.
Claim 9
Dependent Claim
31 words
A compound according to claim 2, wherein R 2 is selected from hydrogen, a C 1 to C 12 straight or branched chain alkyl, and a piperidine radical of formula (II).
Claim 10
Dependent Claim
21 words
A compound according to claim 2, wherein the radical R 2 --Z-- is ##STR40## Pip being the radical of formula (II).
Claim 11
Dependent Claim
16 words
A compound according to claim 2, wherein A is hydrogen and B is --X--R 1 --YH.
Claim 12
Dependent Claim
14 words
A compound according to claim 9, wherein A is hydrogen and B is ##STR41##
Claim 13
Dependent Claim
28 words
A compound according to claim 2, wherein R 4 , R 5 , R 7 , R 8 are each methyl and R 6 is hydrogen or methyl.
Claim 14
Dependent Claim
128 words
A compound according to claim 2, wherein R 1 is C 2 to C 10 alkylene or C 6 to C 8 arylene; R 2 is H, C 4 to C 12 alkyl or piperidyl of formula (II); R 3 is H, C 4 to C 12 alkyl or piperidyl of formula (II); R 4 , r 5 , r 7 and R 8 are methyl; R 6 is hydrogen or methyl; R 9 , r 10 , r 11 , r 12 are hydrogen; X, y, z represents --O--, --NH--, or ##STR42## Pip being a piperidyl of formula (II); A is H; B is ##STR43## r being an integer from 2 to 6; m is 0 or 1; and n is an integer from 2 to 100.
Claim 15
Dependent Claim
29 words
A synthetic polymer of increased stability having incorporated with the polymer an amount of a compound according to claim 1 effective to increase the light stability of the polymer.
Claim 16
Dependent Claim
40 words
A composition according to claim 14 wherein --XR 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 1 --Y-- represent a residue ##STR44##
Claim 17
Dependent Claim
13 words
A composition according to claim 14, wherein said synthetic polymer is a polyolefin.
Claim 18
Dependent Claim
12 words
A composition according to claim 16, wherein said synthetic polymer is polypropylene.
Claim 19
Dependent Claim
12 words
A composition according to claim 16, wherein said synthetic polymer is polyethylene.
Claim 20
Dependent Claim
18 words
A composition according to claim 16, wherein said synthetic polymer is in the form of fibers or film.
Claim 21
Dependent Claim
31 words
A composition according to claim 14, wherein said compound is added to the synthetic polymer composition in an amount from 0.1 to 1% by weight referred to the synthetic polymer composition.
Claim 22
Dependent Claim
29 words
A synthetic polymer of increased stability having incorporated with the polymer an amount of a compound according to claim 2 effective to increase the light stability of the polymer.
Claim 23
Independent Claim
382 words
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 3 being a member selected from hydrogen, straight or branched chain C 1 to C 18 alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II): ##STR47## wherein R 4 , R 5 , R 7 , R 8 , the same or different, are members selected from C 1 to C 6 alkyl, and R 6 is selected from H, O, C 1 to C 18 straight or branched chain alkyl, C 2 to C 18 alkenyl or alkynyl, C 7 to C 18 aralkyl; R 1 is selected from C 2 to C 18 straight or branched chain alkylene, C 5 to C 18 cycloalkylene, C 6 to C 18 arylene, C 7 to C 18 aralkylene; R 2 is selected from hydrogen, chlorine, bromine, -OH C 1 to C 18 straight or branched chain alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II), a group ##STR48## wherein R 11 , R 12 are selected from hydrogen or C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl, C 6 to C 12 aryl, C 7 to C 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 1 --YH; in formula (I) there is the condition that at least one of the radicals --X--R 1 --Y-- and --(Z) m --R 2 contains a piperidine radical of formula (II), comprising reacting a compound of formula (IV): hx -- r.sub.1 -- yh (iv) x, y, r 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° C to the solvent boiling temperature, in the presence of an organic or inorganic base.
Claim 24
Independent Claim
382 words
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 3 being a member selected from hydrogen, straight or branched chain C 1 to C 18 alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II): ##STR47## wherein R 4 , R 5 , R 7 , R 8 , the same or different, are members selected from C 1 to C 6 alkyl, and R 6 is selected from H, O, C 1 to C 18 straight or branched chain alkyl, C 2 to C 18 alkenyl or alkynyl, C 7 to C 18 aralkyl; R 1 is selected from C 2 to C 18 straight or branched chain alkylene, C 5 to C 18 cycloalkylene, C 6 to C 18 arylene, C 7 to C 18 aralkylene; R 2 is selected from hydrogen, chlorine, bromine, -OH C 1 to C 18 straight or branched chain alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II), a group ##STR48## wherein R 11 , R 12 are selected from hydrogen or C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl, C 6 to C 12 aryl, C 7 to C 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 1 --YH; in formula (I) there is the condition that at least one of the radicals --X--R 1 --Y-- and --(Z) m --R 2 contains a piperidine radical of formula (II), comprising reacting a compound of formula (IV): hx -- r.sub.1 -- yh (iv) x, y, r 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° C to the solvent boiling temperature, in the presence of an organic or inorganic base.
Claim 25
Dependent Claim
26 words
The method according to claim 22, comprising reacting 2,4-dihalogentriazines of formula (III) with a compound of formula (IV) in a molar ratio from 1:1.5 to 1.5:1.
Claim 26
Dependent Claim
12 words
A method according to claim 22, in which said halogen is chlorine.
Claim 27
Dependent Claim
46 words
A method according to claim 22, comprising reacting a cyanuric halide with a compound of formula (IV) in a molar ratio from 1:1 to 1:1.2, to obtain a product having the formula (VI) ##STR51## ##STR52## in which m is as defined in formula (I) is zero.
Claim 28
Dependent Claim
31 words
A method according to claim 25, wherein said product (VI) is successively reacted with a compound of formula (V) to obtain a product of formula (I) in which m is 1.
Claim 29
Dependent Claim
34 words
A method according to claim 22, comprising reacting a cyanuric halide with a compound of formula (IV) in a molar ratio from 1:2.4 to 1:2.1 to obtain a product of formula (VII) ##STR53## ##STR54##
Claim 30
Independent Claim
345 words
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 3 being a member selected from hydrogen, straight or branched chain C 1 to C 18 alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II): ##STR57## wherein R 4 , R 5 , R 7 , R 8 , the same or different, are members selected from C 1 to C 6 alkyl, and R 6 is selected from H, O, C 1 to C 18 straight or branched chain alkyl, C 2 to C 18 alkenyl or alkynyl, C 7 to C 18 aralkyl; R 1 is selected from C 2 to C 18 straight or branched chain alkylene, C 5 to C 18 cycloalkylene, C 6 to C 18 arylene, C 7 to C 18 aralkylene; R 2 is selected from hydrogen, chlorine, bromine, --OH, C 1 to C 18 straight or branched chain alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II), a group ##STR58## wherein R 11 , R 12 are selected from hydrogen or C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl, C 6 to C 12 aryl, C 7 to C 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 1 --YH; in formula (I) ruling the condition that at least one of the radicals --X--R 1 --Y-- and --(Z) m --R 2 contains a piperidine radical of formula (II), effective to increase the light stability of said synthetic polymer.
Claim 31
Independent Claim
345 words
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 3 being a member selected from hydrogen, straight or branched chain C 1 to C 18 alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II): ##STR57## wherein R 4 , R 5 , R 7 , R 8 , the same or different, are members selected from C 1 to C 6 alkyl, and R 6 is selected from H, O, C 1 to C 18 straight or branched chain alkyl, C 2 to C 18 alkenyl or alkynyl, C 7 to C 18 aralkyl; R 1 is selected from C 2 to C 18 straight or branched chain alkylene, C 5 to C 18 cycloalkylene, C 6 to C 18 arylene, C 7 to C 18 aralkylene; R 2 is selected from hydrogen, chlorine, bromine, --OH, C 1 to C 18 straight or branched chain alkyl, C 5 to C 18 cycloalkyl, substituted or not substituted C 6 to C 18 aryl, C 7 to C 18 aralkyl, a piperidine radical of formula (II), a group ##STR58## wherein R 11 , R 12 are selected from hydrogen or C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl, C 6 to C 12 aryl, C 7 to C 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 1 --YH; in formula (I) ruling the condition that at least one of the radicals --X--R 1 --Y-- and --(Z) m --R 2 contains a piperidine radical of formula (II), effective to increase the light stability of said synthetic polymer.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1981-04-24 | 1981-10-24 | 1982-04-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-04-24 | 1985-10-24 | 1986-04-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-04-24 | 1989-10-24 | 1990-04-25 | $7700.00 | Window Closed / Lapsed |