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US 8,262,945 B2Granted
Stabilization of photochromic systems
AssigneeBASF SE
InventorsMara Destro, Dario Lazzari, Dirk Simon, Manuele Vitali
Life of this patent
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Abstract
Photochromic compositions are disclosed comprising a polymeric material, a photochromic dye, a hydroxyphenyl triazine UV absorber and, optionally, a further light stabilizer selected from the sterically hindered amines. These systems provide a reversible photochromic effect and show improved light stabilization and color fastness.
Claims10
A photochromic composition comprising
- (a) a polymeric material,
- (b) a photochromic dye and
- (c) a stabilizer combination of
- (i) a hydroxyphenyl triazine UV absorber and
- (ii) at least one sterically hindered alkoxyamine light stabilizer, wherein the sterically hindered alkoxyamine is a compound having a molecular weight of 1500-15000 g/mol, and is compound of formula (2g)
- in which the index m18 ranges from 1 to 15;
- R12 is C2-C12alkylene, C4-C12alkenylene, C5-C7cycloalkylene, C5-C7cycloalkylene-di(C1-C4alkylene), C1-C4alkylenedi(C5-C7cycloalkylene), phenylenedi(C1-C4alkylene) or C4-C12alkylene interrupted by 1,4-piperazinediyl, —O— or >N—X1 with X1 being C1-C12acyl or (C1-C12alkoxy)carbonyl or having one of the definitions of R14 given below except hydrogen;
- or R12 is a group of the formula (2g′) or (2g″);
- X2 being C1-C18alkyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl;
- phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl or C1-C4alkoxy;
- C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl;
- and
- the radicals X3 being independently of one another C2-C12alkylene;
- the radicals A are independently of one another —OR13, —N(R14)(R15) or a group of the formula (2g′″);
- R13, R14 and R15, which are identical or different, are hydrogen, C1-C18alkyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl;
- C3-C18alkenyl, phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl or C1-C4alkoxy;
- C7-C9-phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl;
- tetrahydrofurfuryl or C2-C4alkyl which is substituted in the 2, 3 or 4 position by —OH, C1-C8alkoxy, di(C1-C4alkyl)amino or a group of the formula (2gIV);
- with Y being —O—, —CH2—, —CH2CH2— or >N—CH3,
- or —N(R14)(R15) is additionally a group of the formula (2gIV);
- X is —O— or >N—R16;
- R16 is hydrogen, C1-C18alkyl, C3-C18alkenyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl;
- C7-C9-phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl;
- tetrahydrofurfuryl, a group of the formula (2gV),
- or C2-C4alkyl which is substituted in the 2, 3 or 4 position by —OH, C1-C8alkoxy, di(C1-C4alkyl)amino or a group of the formula (2gIV);
- R11 has one of the definitions given for R16;
- and
- the radicals B have independently of one another one of the definitions given for A,
- wherein
- a ratio of component (c) to component (b) is in the range of 0.01 to 100 parts of component (c) per part of component (b),
- wherein the triazine UV absorber is of formula
- wherein
- R28 is (CH2—CH2—O—)n—R29;
- —CH2—CH(OH)—CH2—O—R29 or —CH(R30)—CO—O—R40;
- n is 0 or 1;
- R29 is C1-C13alkyl or C2-C20alkenyl or C6-C12aryl or CO—C1-C18alkyl;
- R30 is hydrogen or C1-C8alkyl;
- R40 is C1-C12alkyl or C2-C12alkenyl or C5-C6cycloalkyl and
- wherein the photochromic dye is a naphthopyran of formula
- where R is hydrogen;
- C1-C6alkyl;
- C1-C6alkoxy;
- —NR′R″—NO2;
- where R′ and R″ independently are hydrogen or C1-C12alkyl, C4-C12cycloalkyl, C7-C13 phenylalkyl or together are tetramethylene or pentamethylene or O-interruped tetramethylene wherein the dye is present in an amount of 0.001 to 10% by weight, with respect to the total weight of the polymeric material (a).
41 more elements
A process of stabilizing a photochromic system comprising (b) a photochromic dye in (a) a polymer matrix against colour fading induced by irradiation, which process comprises incorporating
- (c) (i) a hydroxyphenyl triazine UV absorber into the polymer matrix and/or into a polymer layer covering said polymer matrix and incorporating (c) (ii) a sterically hindered alkoxyamine light stabilizer into the polymer matrix,
- wherein the hydroxyphenyl triazine UV absorber (i) is of formula
- wherein
- R28 is (CH2—CH2—O—)n—R29;
- —CH2—CH(OH)—CH2—O—R29;
- or —CH(R30)—CO—O—R40;
- n is 0 or 1;
- R29 is C1-C13alkyl or C2-C20alkenyl or C6-C12aryl or CO—C1-C18alkyl;
- R30 is hydrogen or C1-C8alkyl;
- R40 is C1-C12alkyl or C2-C12alkenyl or C5-C6cycloalkyl, wherein the sterically hindered alkoxyamine is a compound having a molecular weight of 1500-15000 g/mol, and is compound of formula (2g)
- in which the index m18 ranges from 1 to 15;
- R12 is C2-C12alkylene, C4-C12alkenylene, C5-C7cycloalkylene-di(C1-C4alkylene), C1-C4alkylenedi(C5-C7cycloalkylene), phenylenedi(C1-C4alkylene) or C4-C12alkylene interrupted by 1,4-piperazinediyl, —O— or >N—X1 with X1 being C1-C12acyl or (C1-C12alkoxy)carbonyl or having one of the definitions of R14 given below except hydrogen;
- or R12 is a group of the formula (2g′) or (2g″);
- X2 being C1-C18alkyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl;
- phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl or C1-C4alkoxy;
- C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl;
- and
- the radicals X3 being independently of one another C2-C12alkylene;
- the radicals A are independently of one another —OR13, —N(R14)(R15) or a group of the formula (2g′″);
- R13, R14 and R15, which are identical or different, are hydrogen, C1-C18alkyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl;
- C3-C18alkenyl, phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl or C1-C4alkoxy;
- C7-C9-phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl;
- tetrahydrofurfuryl or C2-C4alkyl which is substituted in the 2, 3 or 4 position by —OH, C1-C8alkoxy, di(C1-C4alkyl)amino or a group of the formula (2gIV);
- with Y being —O—, —CH2—, —CH2CH2— or >N—CH3,
- or —N(R14)(R15) is additionally a group of the formula (2gIV);
- X is —O— or >N—R16;
- R16 is hydrogen, C1-C18alkyl, C3-C18alkenyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl;
- C7-C9-phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl;
- tetrahydrofurfuryl, a group of the formula (2gV),
- or C2-C4alkyl which is substituted in the 2, 3 or 4 position by —OH, C1-C8alkoxy, di(C1-C4alkyl)amino or a group of the formula (2gIV);
- R11 has one of the definitions given for R16;
- and
- the radicals B have independently of one another one of the definitions given for A,
- wherein the photochromic dye of component (b) is present in an amount of 0.001 to 10% by weight, with respect to the total weight of the polymeric material (a) and is a naphthopyran of formula
- where R is hydrogen;
- C1-C6alkyl;
- C1-C6alkoxy;
- —NR′R″;
- —NO2;where R′ and R″ independently are hydrogen or C1-C12alkyl, C4-C12cycloakyl, C7-C13phenylalkyl or together are tetramethylene or pentamethylene or O-interrupted tetramethylene and
- wherein
- a ratio of component (c) to component (b) is in the range of 0.01 to 100 parts of component (c) per part of component (b).
38 more elements
Dependencies are inferred from the claim text.