Phenyl ether-substituted hydroxyphenyl triazine ultraviolet light absorbers
AssigneeCytec Technology Corp.
InventorsRam Baboo Gupta, Hargurpreet Singh, Russell C. Cappadona
Life of this patent
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Abstract
This invention relates generally to phenyl ether substituted triazines compounds and compositions containing same and their use to protect against degradation by environmental forces. A method for stabilizing a material by incorporating such triazines is also disclosed.
Claims34
A compound of Formula I
- 31
- wherein R1, R2, R3, R4, R5 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbon atoms, OR, NRR′, CONRR′, OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R′ are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, and optionally with either of R1 and R2, R3 and R4, or R4 and R5, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring;
- each of T and T′ is independently a direct bond, oxygen, NR, sulfur or a functional groups containing these elements;
- X is independently selected from hydrogen and a blocking group;
- each of Y, R6 and R7 are each independently hydrogen, hydrocarbyl group, a functional hydrocarbyl group, halogen, hydroxyl, cyano, —O(hydrocarbyl), —O(functional hydrocarbyl), —N(hydrocarbyl)2, —N(functional hydrocarbyl)2, —N(hydrocarbyl)(functional hydrocarbyl), —S(hydrocarbyl), —S(functional hydrocarbyl), —SO2(hydrocarbyl), —SO2(functional hydrocarbyl), —SO3(hydrocarbyl), —SO3(functional hydrocarbyl), —CO2(hydrocarbyl), —CO2(functional hydrocarbyl), —CO(hydrocarbyl), —CO (functional hydrocarbyl), —OCO(hydrocarbyl), —OCO(functional hydrocarbyl), —CONH2, —CONH(hydrocarbyl), —CONH(functional hydrocarbyl), —CON(hydrocarbyl)2, —CON(hydrocarbyl)(functional hydrocarbyl), —CON(functional hydrocarbyl)2, wherein the hydrocarbyl or functional hydrocarbyl may be the same or different and has 1 to 24 carbon atoms;
- Z is Y,
- 32
- and wherein L is hydrogen, a hydrocarbyl of 1 to 24 carbon atoms, or a functional hydrocarbyl of 1 to 24 atoms.
A compound according to claim 4 wherein TZ is
- 34
- and wherein L is hydrogen, a hydrocarbyl group of 1 to 24 carbon atoms, or a functional hydrocarbyl group of 1 to 24 carbon atoms;
- X is independently selected from hydrogen and a blocking group;
- and
- R6 and R7 are independently hydrogen, hydrocarbyl, functional hydrocarbyl, halogen, hydroxyl, —O(hydrocarbyl), —O(functional hydrocarbyl), —S(hydrocarbyl), —SO2(hydrocarbyl), —SO3(hydrocarbyl), —COO(hydrocarbyl), —CO(hydrocarbyl), —OCO(hydrocarbyl), —N(hydrocarbyl)(hydrocarbyl), —S(functional hydrocarbyl), —SO2(functional hydrocarbyl), —CO(functional hydrocarbyl), —COO(functional hydrocarbyl), —CO(functional hydrocarbyl), —OCO(functional hydrocarbyl), —N(functional hydrocarbyl)(functional hydrocarbyl) or cyano.
15 The method of claim 13, wherein the material to be stabilized is selected from the group consisting of polyolefins, polyesters, polyethers, polyketones, polyamides, natural and synthetic rubbers, polyurethanes, polystyrenes, high-impact polystyrenes, polyacrylates, polymethacrylates, polyacetals, polyacrylonitriles, polybutadienes, polystyrenes, ABS, SAN (styrene acrylonitrile), ASA (acrylate styrene acrylonitrile), cellulosic acetate butyrate, cellulosic polymers, polyimides, polyamideimides, polyetherimides, polyphenylsulfide, PPO, polysulfones, polyethersulfones, polyvinylchlorides, polycarbonates, polyketones, aliphatic polyketones, thermoplastic TPU's, aminoresin cross-linked polyacrylates and polyesters, or polyisocyanate cross-linked polyesters and polyacrylates, phenol/formaldehyde, urea/formaldehyde and melamine/formaldehyde resins, drying and non-drying alkyd resins, alkyd resins, polyester resins, acrylate resins cross-linked with melamine resins, urea resins, isocyanates, isocyanurates, carbamates, and epoxy resins, cross-linked epoxy resins derived from aliphatic, cycloaliphatic, heterocyclic and aromatic glycidyl compounds, which are cross-linked with anhydrides or amines, polysiloxanes, Michael addition polymers, amines, blocked amines with activated unsaturated and methylene compounds, ketimines with activated unsaturated and methylene compounds, polyketimines in combination with unsaturated acrylic polyacetoacetate resins, polyketimines in combination with unsaturated acrylic resins, radiation curable compositions, epoxymelamine resins, organic dyes, cosmetic products, cellulose-based paper formulations, photographic film paper, ink, fibers and combinations thereof.
The method of claim 15, wherein the material is a polyolefin, polyamide, polyurethane, polyester or a polycarbonate.
A compound having the Formula
- 44
- wherein R1, R2, R3, R4, R5 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbon atoms, OR, NRR′, CONRR′, OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R′ are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, and optionally with either of R1 and R2, R3 and R4, or R4 and R5, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring;
- Z′ is a halogen,
- and W is
- 45
- or a halogen.
Dependencies are inferred from the claim text.