Poly-trisaryl-1,3,5-Triazine carbamate ultraviolet light absorbers
AssigneeCiba Specialty Chemicals Corporation
InventorsRam Baboo Gupta, Dennis John Jakiela
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Abstract
The present invention relates to novel carbamate containing trisaryl-1,3,5-triazines and the use thereof as an ultraviolet light absorber. In particular, the presently claimed compounds comprise a carbamate triazine polymer which is particularly useful, either alone or in combination with other additives, including other ultraviolet light absorbers and stabilizers, in stabilizing a polymeric film or molded article from degradation due to exposure to actinic radiation.
Claims53
A compound selected from the group consisting of compounds of formula (I), (II) and (III):
- wherein:
- (a) A is a polyvalent hydrocarbyl or a polyvalent 1,3,5-triazine;
- (b) each X is independently hydrogen, allyl, —CORa, —SO2Rb, SiRcRdRe, —PRfRg, or —PORfRg;
- (c) each of Y and Z is independently an aryl ring of formula (IV):
- (d) each R is independently a hydrocarbyl group or a functional hydrocarbyl group;
- and is different from each other R group;
- each R′ is independently a hydrocarbylene group, a functional hydrocarbylene group or the group —CH2CONC4H9(CH2)2—;
- (e) each Ra is independently C1-C8 alkyl, halogen-substituted C1-C8 alkyl, C5-C12 cycloalkyl, C2-C8 alkenyl, —CH2—CO—CH3, C7-C12 aralkyl, C1-C12 alkoxy, or phenyl which is unsubstituted or substituted by C1-C12 alkyl, C1-C4 alkoxy, halogen and/or benzyl;
- (f) each Rb is independently C1-C12 alkyl, C6-C10 aryl, or C7-C18 alkylaryl;
- (g) each Rc, Rd, and Re is independently C1-C18 alkyl, cyclohexyl, phenyl, or C1-C18 alkoxy;
- (h) each Rf and Rg is independently C1-C12 alkoxy, phenoxy, C1-C12 alkyl, C5-C12 cycloalkyl, benzyl, tolyl, or phenyl;
- (i) each R1, R2 and R4 is independently hydrogen, hydrocarbyl, functional hydrocarbyl, —O(hydrocarbyl), —O(functional hydrocarbyl), —SR, halogen, —SO3R, —COOR, —COR, —OCOR, —NRR or cyano;
- (j) each R3 is independently R, —OR, —SR, halogen, —SO3R, —COOR, —COR, —NRR or cyano;
- and
- (k) n is an integer between 2 and about 50.
A method of stabilizing a material which is subject to degradation by actinic radiation which comprises the addition to said material of an effective amount of at least one compound selected from the group consisting of compounds of formula (I), (II) and (III)
- wherein:
- (a) A is a polyvalent hydrocarbyl or a polyvalent 1,3,5-triazine;
- (b) each X is independently hydrogen, allyl, —CORa, —SO2Rb, SiRcRdRe, —PRfRg, or —PORfRg;
- (c) each of Y and Z is independently an aryl ring of formula (IV)
- (d) each R is independently a hydrocarbyl group or a functional hydrocarbyl group;
- and is different from each other R group;
- each R′ is independently a hydrocarbylene group, a functional hydrocarbylene group or the group —CH2CONC4H9(CH2)2—;
- (e) each Ra is independently C1-C8 alkyl, halogen-substituted C1-C8 alkyl, C5-C12 cycloalkyl, C2-C8 alkenyl, —CH2—CO—CH3, C7-C12 aralkyl, C1-C12 alkoxy, or phenyl which is unsubstituted or substituted by C1-C12 alkyl, C1-C4 alkoxy, halogen and/or benzyl;
- (f) each Rb is independently C1-C12 alkyl, C6-C10 aryl, or C7-C18 alkylaryl;
- (g) each Rc, Rd, and Re is independently C1-C18 alkyl, cyclohexyl, phenyl, or C1-C18 alkoxy;
- (h) each Rf and Rg is independently C1-C12 alkoxy, phenoxy, C1-C12 alkyl, C5-C12 cycloalkyl, benzyl, tolyl, or phenyl;
- (i) each R1, R2 and R4 is independently hydrogen, hydrocarbyl, functional hydrocarbyl, —O(hydrocarbyl), —O(functional hydrocarbyl), —SR, halogen, —SO3R, —COOR, —COR, —OCOR, —NRR or cyano;
- (j) each R3 is independently R, —OR, —SR, halogen, —SO3R, —COOR, —COR, —NRR or cyano;
- and
- (k) n is an integer between 2 and about 50.
An actinic radiation stabilizing composition which comprises a binder and a compound selected from the group consisting of compounds of formula (I), (II) and (III):
- wherein:
- (a) A is a polyvalent hydrocarbyl or a polyvalent 1,3,5-triazine;
- (b) each X is independently hydrogen, allyl, —CORa, —SO2Rb, SiRcRdRe, —PRfRg, or —PORfRg;
- (c) each of Y and Z is independently an aryl ring of formula (IV)
- (d) each R is independently a hydrocarbyl group or a functional hydrocarbyl group;
- and is different from each other R group;
- each R′ is independently a hydrocarbylene group, a functional hydrocarbylene group or the group —CH2CONC4H9(CH2)2—;
- (e) each Ra is independently C1-C8 alkyl, halogen-substituted C1-C8 alkyl, C5-C12 cycloalkyl, C2-C8 alkenyl, —CH2—CO—CH3, C7-C12 aralkyl, C1-C12 alkoxy, or phenyl which is unsubstituted or substituted by C1-C12 alkyl, C1-C4 alkoxy, halogen and/or benzyl;
- (f) each Rb is independently C1-C12 alkyl, C6-C10 aryl, or C7-C18 alkylaryl;
- (g) each Rc, Rd, and Re is independently C1-C18 alkyl, cyclohexyl, phenyl, or C1-C18 alkoxy;
- (h) each Rf and Rg is independently C1-C12 alkoxy, phenoxy, C1-C12 alkyl, C5-C12 cycloalkyl, benzyl, tolyl, or phenyl;
- (i) each R1, R2 and R4 is independently hydrogen, hydrocarbyl, functional hydrocarbyl, —O(hydrocarbyl), —O(functional hydrocarbyl), —SR, halogen, —SO3R, —COOR, —COR, —OCOR, —NRR or cyano;
- (j) each R3 is independently R, —OR, —SR, halogen, —SO3R, —COOR, —COR, —NRR or cyano;
- and
- (k) n is an integer between 2 and about 50.
Dependencies are inferred from the claim text.