US2002165298A1PendingUtilityA1
Amino- and hydroxysubstituted triphenyl-s-triazines as stabilizers
Priority: Apr 2, 1996Filed: Dec 11, 2001Published: Nov 7, 2002
Est. expiryApr 2, 2016(expired)· nominal 20-yr term from priority
A61Q 17/04C07D 251/24A61K 2800/52C07D 265/22A61K 31/785A61K 8/4966
54
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Claims
Abstract
The present invention provides compounds having the formula: in which R is hydrogen, hydroxy, halogen, C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 1 -C 20 -alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenoxy, C 2 -C 20 alkynoxy or C 7 -C 13 aralkyl; R 1 and R 2 , independently, are hydrogen, C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, C 7 -C 13 aralkyl, —C(═O)-R 4 (in which R 4 is C 1 -C 20 alkyl, C 2 -C 20 alkyl interrupted by 1 to 6 oxygen atoms, hetero-substituted C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, C 2 20 alkenyl, C 2 C 20 alkynyl, C 1 -C 20 -alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenoxy, C 2 alkynoxy, C 6 -C 12 aryl, C 6 -C 12 aryloxy or C 7 C 13 aralkyl), or —C(═O)-NH-R 1 in which R 1 has its previous significance; and R 3 is hydrogen, halogen, hydroxy, C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 1 -C 20 -alkoxy, C 4 -C 12 -cycloalkoxy, C 2 C 20 alkenoxy, C 2 -C 20 alkynoxy, phenyl, C 7 -C 13 aralkyl or —N(R 1 )(R 2 ) in which R 1 and R 2 have their previous significance, or R 1 and R 2 together form a C 4 -C 12 membered ring. The new triphenyltriazine compounds have improved absorption spectrum characteristics and superior resistance to exposure to UV light, relative to known triphenyltriazine compounds.
Claims
exact text as granted — not AI-modified1 . A compound having the formula:
in which R is hydrogen, hydroxy, halogen, C 1 C 20 -alkyl, C 4 -C 12 cycloalkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 1 -C 20 -alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenoxy, C 2 -C 20 alkynoxy or C 7 -C 13 aralkyl; R 1 and R 2 , independently, are hydrogen, C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, C 7 -C 13 aralkyl, —C(═O)-R 4 (in which R 4 is C 1 -C 20 alkyl, C 2 -C 20 alkyl interrupted by 1 to 6 oxygen atoms, hetero-substituted C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 1 -C 20 -alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenoxy, C 2 -C 20 alkynoxy, C 6 -C 12 aryl, C 6 -C 12 aryloxy or C 7 -C 13 aralkyl), or —C(═O)-NH-R 1 in which R 1 has its previous significance; and R 3 is hydrogen, halogen, hydroxy, C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 1 -C 20 -alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenoxy, C 2 -C 20 alkynoxy, phenyl, C 7 -C 13 aralkyl or —N(R 1 )(R 2 ) in which R 1 and R 2 have their previous significance, or R 1 and R 2 together form a C 4 -C 12 membered ring.
2 . A compound according to claim 1 in which R is hydrogen, hydroxy, halogen, C 1 -C 20 -alkyl or C 1 -C 20 -alkoxy; R 1 and R 2 , independently, are hydrogen, C 1 -C 20 alkyl, C 7 -C 13 aralkyl, —C(═O)-R 4 (in which R 4 is C 1 -C 20 alkyl, C 2 -C 20 alkyl interrupted by 1 to 6 oxygen atoms, C 2 -C 20 alkenyl, C 6 -C 12 aryl or C 6 -C 12 aryloxy), or —C(═O)-NH-R 1 in which R 1 has its previous significance; and R 3 is hydrogen, halogen, hydroxy, C 1 -C 2 alkyl, phenyl, —N(R 1 )(R 2 ) in which R 1 and R 2 have their previous significance or R 1 and R 2 together form a C 4 -C 12 membered ring.
3 . A compound according to claim 1 having the formula:
in which R is hydrogen or C 1 -C 4 alkoxy; either R 1 and R 2 are each hydrogen, or R 1 is hydrogen and R 2 is —C(═O)-R 4 in which R 4 is C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 1 -C 20 alkoxy, phenyl optionally substituted with C 1 -C 4 alkoxy or CH 2 -(OCH 2 CH 2 ) n CH 3 in which n is an integer from 1 to 5; and R 3 is hydrogen, C 1 -C 20 alkyl, hydroxy, C 1 -C 4 alkoxy or phenyl.
4 . A compound according to claim 3 in which R is hydrogen or methoxy; either R 1 and R 2 are each hydrogen, or R 1 is hydrogen and R 2 is —CO—CH 2 -(OCH 2 CH 2 ) n -OCH 3 in which n is an integer from 1 to 5; and R 3 is hydrogen, C 1 -C 20 alkyl, hydroxy, methoxy or phenyl.
5 . A compound according to claim 1 having the formula:
in which either R 1 and R 2 are each hydrogen, or R 1 is hydrogen and R 2 is —C(═O)-R 4 in which R 4 is C 1 -C 20 alkyl, C 1 -C 20 alkenyl, C 1 -C 20 alkoxy, phenyl optionally substituted with C 1 -C 4 alkoxy or CH 2 -(OCH 2 CH 2 ) n -OCH 3 in which n is an integer from 1 to 5; and R 3 is hydrogen, hydroxy, C 1 -C 20 alkyl, methoxy or phenyl.
6 . A compound according to claim 5 in which either R 1 and R 2 are each hydrogen, or R 1 is hydrogen and R 2 is —CO—CH 3 ; and R 3 is hydrogen, methoxy or phenyl.
7 . A composition comprising
(A) an organic material which is sensitive to damage by light, oxygen and/or heat, and (B) as stabilizer, a compound according to any one of claims 1 to 3 .
8 . A composition according to claim 7 comprising from 0.01 to 15 parts by weight of component (B), per 100 parts by weight of component (A).
9 . A composition according to claim 7 or 8 comprising, in addition to components (A) and (B), one or more further stabilizers or further additives.
10 . A composition according to any of claims 7 to 9 comprising, as component (A), a synthetic organic polymer.
11 . A composition according to any of claims 7 to 10 comprising, as component (A), a thermoplastic polymer, a binder for coatings or a photographic material.
12 . A composition according to claim 9 comprising, as component (A), a binder for coatings and, as additional component C), one or more stabilizers selected from light stabilizers of the sterically hindered amine and/or 2-hydroxyphenyl-2H-benzotriazole type.
13 . A composition according to claim 12 in which component C) is present in an amount of 0.05 to 5 parts by weight, per 100 parts by weight of the binder.
14 . A composition according to claim 7 in which the organic material which is sensitive to damage by light, oxygen and/or heat is an undyed, dyed or printed fibre material.
15 . A method of increasing the sun protection factor of textile fibre materials, which comprises applying to the fibre materials a compound according to any one of claims 1 to 6 , in an aqueous or aqueous-organic solution, and then fixing this compound.
16 . A cosmetic preparation comprising at least one compound according to any one of claims 1 to 6 and a cosmetically acceptable auxiliary.
17 . A process for stabilizing organic material against damage by light, oxygen and/or heat, which comprises adding to this material a stabilizer comprising one or more compounds according to any one of claims 1 to 6 .
18 . The use of a compound according to any one of claims 1 to 6 as a sunscreen for the human skin.
19 . A process for the production of a compound of formula (1A ) comprising reacting an o-hydroxybenzamide of formula:
in which R is as defined in claim 1 , with a benzoyl chloride of formula:
in which R 3 is as defined in claim 1 , to produce a compound of formula:
in which R and R 3 have their previous significance; and the compound of formula (6) is then reacted with a benzamidine having the formula:
in which R, R 1 and R 2 are as defined in claim 1 , to produce a compound of formula (1A).
20 . A process for the production of a compound of formula (1A ) comprising comprising reacting an o-hydroxybenzamide of formula (4) as definedin claim 19 with a p-nitro-benzoyl chloride of formula:
in which R 3 is as defined in claim 1 , to produce a compound having the formula:
in which R and R 3 are as defined in claim 1 , then reacting the compound of formula (9) with a benzamidine having the formula:
in which R is as defined in claim 1 , to produce a compound of formula:
in which R and R 3 are as defined in claim 1 , and finally hydrogenating the compound of formula (11) to produce a compound of formula (1A).
21 . A process for the production of a compound of formula (1) or (1A) comprising reacting an o-hydroxybenzamide of formula (4) as defined in claim 19 with a p-acylaminobenzoyl chloride having the formula:
in which R 3 and R 4 are as defined in claim 1 , to produce compounds having the formula:
in which R, R 3 and R 4 are as defined in claim 1 , and finally reacting the compound of formula (13) with a compound of formula (10) to produce a compound of formula:
in which R, R 3 and R 4 are as defined in claim 1 .
22 . The compounds having the formula:
in which R and R 3 are as defined in claim 1 .
23 . A process for the production of compounds having the formula (6) as defined in claim 22 comprising reacting an o-hydroxybenzamide of formula:
in which R is as defined in claim 1 , with a benzoyl chloride of formula:
in which R 3 is as defined in claim 1 , to produce a compound of formula (6).
24 . A compound having the formula (9):
in which R and R 3 are as defined in claim 1 .
25 . A process for the production of a compound of formula (9) as defined in claim 24 comprising reacting an o-hydroxybenzamide of formula (4) as defined in claim 19 with a p-nitro-benzoyl chloride of formula:
in which R 3 is as defined in claim 1 , to produce a compound having the formula (9).
26 . A compound having the formula (13):
in which R, R 3 and R 4 are as defined in claim 1 .
27 . A process for the production of a compound having the formula (13) comprising reacting an o-hydroxybenzamide of formula (4) as defined in claim 19 with a p-acylaminobenzoyl chloride having the formula:
in which R 3 and R 4 are as defined in claim 1 , to produce compounds having the formula(13).Join the waitlist — get patent alerts
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