Ultraviolet light absorbing ketones of 2-(2-hydroxyphenyl) benzotriazole
OwnerChia-Hu Changinventor
Life of this patent
Estimating the term…
Abstract
The invention relates to ultraviolet light absorbing compounds, their preparation and uses as protective agents and stabilizers in coatings, plastics and topically applied products. The compounds are ketone derivatives of 2-(2-hydroxyphenol)benzotriazole of formula I, where R1 is hydrogen atom, or a halogen atom, or a straight-chain or branched lower alkyl or lower alkoxy of 1 to 4 carbon atoms; R2 is an unsubtituted or substituted aryl group or an unsubstituted or substituted straight-chain or branched alkyl having 1 to 18 carbon atoms or a cycloaliphatic group having 5 to 6 carbon atoms; and R3 is a straight-chain or branched alkyl or alkylaryl group or alkoxyl or phenyl or phenyl substituted with alkyl, cycloalkyl, carboalkoxy, chlorine or arylalkyl groups.
Claims12
A composition of matter comprising:
- i) a polymer selected from the group consisting of polyesters, polycarbonates, polyester resins, polysulfones, polyamides, acrylic polymers, acrylic resins, alkyd resins, polyolefins, polystyrenes, vinyl polymers, polyvinylchloride, polyureas, polyurethanes, poly hydrocarbons, polypeptides, cellulose polymers, cellulose ethers, cellulose esters, latex polymers, and combinations thereof;
- ii) from 0.01 to 10% of an ultraviolet light absorbing compound or compounds having the formula I that acts as stabilizer against damage from UV radiation:
- wherein
- R1 is is selected from the group consisting of hydrogen, a halogen atom, a straight-chain or branched lower alkyl or lower alkoxy of 1 to 4 carbon atoms;
- R2 is selected from the group consisting of, a propyl group, a butyl group, an amyl group, a hexyl group, an octyl group, a nonyl group, an isopropyl group, a tertiary butyl group, a tertiary octyl group, a 2-ethylhexyl group, a cumyl group, a cyclohexyl group, a cyclohexyl group substituted with an alkyl group of 1 to 4 carbon atoms and a cyclohexyl group substituted with an alkoxyl group of 1 to 4 carbon atoms;
- and
- R3 is selected from the group consisting of a straight-chain or branched alkyl of 1 to 14 carbon atoms, an alkylaryl group of 7 to 12 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a phenyl group, a phenyl group substituted with an alkyl group of 1 to 8 carbon atoms, a cycloalkyl group of 5 to 6 carbon atoms, a carboalkoxy group of 2 to 9 carbon atoms, chlorine, and an arylalkyl group of 7 to 9 carbon atoms;
- and
- wherein the ultraviolet light absorbing compound or compounds is prepared by a process comprising the steps of:
- (a) reacting a 2-benzotriazolyl-4-hydrocarbyl phenol with an acid chloride or an organic acid or an organic anhydride in the presence of an acid catalyst and an optional solvent at a temperature up to reflux conditions wherein the ratio the 2-benzotriazolyl-4-hydrocarbyl phenol to the acid chloride, organic acid or organic anhydride is about 3:1 to about 1:3;
- (b) increasing the temperature to between about 100° C. and about 200° C. for a period of time sufficient to produce the UV absorbing compound of Formula I by a Fries rearrangement.
Dependencies are inferred from the claim text.