CA2396221A1 - Method of content protection with durable uv absorbers - Google Patents
Method of content protection with durable uv absorbers Download PDFInfo
- Publication number
- CA2396221A1 CA2396221A1 CA002396221A CA2396221A CA2396221A1 CA 2396221 A1 CA2396221 A1 CA 2396221A1 CA 002396221 A CA002396221 A CA 002396221A CA 2396221 A CA2396221 A CA 2396221A CA 2396221 A1 CA2396221 A1 CA 2396221A1
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- CA
- Canada
- Prior art keywords
- carbon atoms
- alkyl
- straight
- substituted
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000006096 absorbing agent Substances 0.000 title claims abstract 18
- 230000005855 radiation Effects 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 193
- 125000000217 alkyl group Chemical group 0.000 claims 84
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 49
- 229910052739 hydrogen Inorganic materials 0.000 claims 46
- 239000001257 hydrogen Substances 0.000 claims 46
- 125000003884 phenylalkyl group Chemical group 0.000 claims 42
- 150000002431 hydrogen Chemical class 0.000 claims 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims 29
- 125000003342 alkenyl group Chemical group 0.000 claims 24
- 125000002947 alkylene group Chemical group 0.000 claims 21
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 15
- -1 3-oxapentamethylene Chemical group 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 8
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 7
- 239000012964 benzotriazole Substances 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000004956 cyclohexylene group Chemical group 0.000 claims 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 3
- LEVFXWNQQSSNAC-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxyphenol Chemical compound OC1=CC(OCCCCCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 LEVFXWNQQSSNAC-UHFFFAOYSA-N 0.000 claims 3
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 claims 3
- 239000004593 Epoxy Substances 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 3
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 claims 2
- CIYRKILUPYIMEP-UHFFFAOYSA-N C(C)(CC)N(C(=O)C=1C=C(C=CC=1F)C1NC(NC(=C1C(=O)NC=1C=C2C=NNC2=CC=1)C)=O)C Chemical compound C(C)(CC)N(C(=O)C=1C=C(C=CC=1F)C1NC(NC(=C1C(=O)NC=1C=C2C=NNC2=CC=1)C)=O)C CIYRKILUPYIMEP-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000001118 alkylidene group Chemical group 0.000 claims 2
- 125000000732 arylene group Chemical group 0.000 claims 2
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 claims 2
- 125000005569 butenylene group Chemical group 0.000 claims 2
- 125000005622 butynylene group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000005022 packaging material Substances 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- YYFDMPHIONBOKZ-UHFFFAOYSA-N 4-n-(1-benzylpiperidin-4-yl)-2-n-[3-(dimethylamino)propyl]-6,7-dimethoxyquinazoline-2,4-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC(NCCCN(C)C)=NC=1NC(CC1)CCN1CC1=CC=CC=C1 YYFDMPHIONBOKZ-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 230000002939 deleterious effect Effects 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 125000006839 xylylene group Chemical group 0.000 claims 1
- 150000001565 benzotriazoles Chemical class 0.000 abstract 1
- 235000013361 beverage Nutrition 0.000 abstract 1
- 239000002537 cosmetic Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000010348 incorporation Methods 0.000 abstract 1
- 239000002453 shampoo Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Wrappers (AREA)
- Cosmetics (AREA)
- Packages (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Abstract
The contents of clear or lightly colored plastic containers or films are protected from ultraviolet radiation by the incorporation of certain UV absorbers of the class of durable benzotriazoles and tris-aryl-s-triazines in the container or film. Contents to be protected include foodstuffs, beverages, pharmaceuticals, cosmetics, personal care products, shampoos and the like.
Claims (17)
1. A plastic container or film for content storage which protects the contents therein against the deleterious effects of ultraviolet radiation which comprises (a) a clear or lightly colored plastic, and (b) an effective stabilizing amount of one or more compounds selected from the group consisting of durable hydroxyphenyl benzotriazole and tris-aryl-s-triazine UV
absorbers.
absorbers.
2. A plastic container or film according to claim 1 wherein said benzotriazole UV
absorbers are of formula (I), (II) or (III) wherein G1 and G1' are independently hydrogen or halogen, G2 and G2' are independently halogen, nitro, cyano, perfluoroalkyl of 1 to 12 carbon atoms, -COOG3, -P(O)(C6H5)2, -CO-G3, -CO-NH-G3, -CO-N(G3)2, -N(G3)-CO-G3, E3SO-or E3SO2-; or G2' is also hydrogen, G3 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, E1 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms; or E1 is alkyl of 1 to 24 carbon atoms substituted by one or two hydroxy groups, when E1 is phenylalkyl of 7 to 15 carbon atoms or phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, G2 may also be hydrogen, E2 and E2' are independently straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by one to three alkyl of 1 to 4 carbon atoms; or E2 and E2' are independently said alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more -OH, -OCOE11, -OE4, -NCO, -NH2, -NHCOE11, -NHE4 or -N(E4)2, or mixtures thereof, where E4 is straight or branched chain alkyl of 1 to 24 carbon atoms; or said alkyl or said alkenyl interrupted by one or more -O-, -NH- or -NE4- groups or mixtures thereof and which can be unsubstituted or substituted by one or more -OH, -OE4 or -NH2 groups or mixtures thereof;
n is 1 or 2, when n is 1, E5 is OE6 or NE7E8, or E5 is -PO(OE12)2, -OSi(E11)3 or -OCO-E11, or straight or branched chain C1-C24alkyl which is interrupted by -O-, -S- or -NE11 and which can be unsubstituted or substituted by -OH or -OCO-E11, C5-C12 cycloalkyl which is unsubstituted or substituted by -OH, straight chain or branched C2-C18alkenyl which is unsubstituted or substituted by -OH, C7-C15aralkyl, -CH2-CHOH-E13 or glycidyl, E6 is hydrogen, straight or branched chain C1-C24alkyl which is unsubstituted or substituted by one or more OH, OE4 or NH2 groups, or -OE6 is -(OCH2CH2)w OH or -(OCH2CH2)w OE21 where w is 1 to 12 and E21 is alkyl of 1 to 12 carbon atoms, E7 and E8 are independently hydrogen, alkyl of 1 to 18 carbon atoms, straight or branched chain C3-C18alkyl which is interrupted by -O-, -S- or -NE11-, C5-C12cycloalkyl, C6-C14aryl or C1-C3hydroxylalkyl, or E7 and E8 together with the N atom are a pyrrolidine, piperidine, piperazine or morpholine ring, E5 is -X-(Z)p-Y-E15 wherein X is -O- or -N(E16)-, Y is -O- or -N(E17)-, Z is C2-C12-alkylene, C4-C12-alkylene interrupted by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is C3-C12-alkylene, butenylene, butynylene, cyclohexylene or phenylene, each substituted by a hydroxyl group, m is zero, 1 or 2, p is 1, or p is also zero when X and Y are -N(E16)- and -N(E17)-, respectively, E15 is a group -CO-C(E18)=C(H)E19 or, when Y is -N(E17)-, forms together with E17 a group -CO-CH=CH-CO-, wherein E18 is hydrogen or methyl, and E19 is hydrogen, methyl or -CO-X-E20, wherein E20 is hydrogen, C1-C12-alkyl or a group of the formula wherein the symbols E1, G2, X, Z, m and p have the meanings defined above, and E16 and E17 independently of one another are hydrogen, C1-C12-alkyl, C3-C12-alkyl interrupted by 1 to
absorbers are of formula (I), (II) or (III) wherein G1 and G1' are independently hydrogen or halogen, G2 and G2' are independently halogen, nitro, cyano, perfluoroalkyl of 1 to 12 carbon atoms, -COOG3, -P(O)(C6H5)2, -CO-G3, -CO-NH-G3, -CO-N(G3)2, -N(G3)-CO-G3, E3SO-or E3SO2-; or G2' is also hydrogen, G3 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, E1 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms; or E1 is alkyl of 1 to 24 carbon atoms substituted by one or two hydroxy groups, when E1 is phenylalkyl of 7 to 15 carbon atoms or phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, G2 may also be hydrogen, E2 and E2' are independently straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by one to three alkyl of 1 to 4 carbon atoms; or E2 and E2' are independently said alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more -OH, -OCOE11, -OE4, -NCO, -NH2, -NHCOE11, -NHE4 or -N(E4)2, or mixtures thereof, where E4 is straight or branched chain alkyl of 1 to 24 carbon atoms; or said alkyl or said alkenyl interrupted by one or more -O-, -NH- or -NE4- groups or mixtures thereof and which can be unsubstituted or substituted by one or more -OH, -OE4 or -NH2 groups or mixtures thereof;
n is 1 or 2, when n is 1, E5 is OE6 or NE7E8, or E5 is -PO(OE12)2, -OSi(E11)3 or -OCO-E11, or straight or branched chain C1-C24alkyl which is interrupted by -O-, -S- or -NE11 and which can be unsubstituted or substituted by -OH or -OCO-E11, C5-C12 cycloalkyl which is unsubstituted or substituted by -OH, straight chain or branched C2-C18alkenyl which is unsubstituted or substituted by -OH, C7-C15aralkyl, -CH2-CHOH-E13 or glycidyl, E6 is hydrogen, straight or branched chain C1-C24alkyl which is unsubstituted or substituted by one or more OH, OE4 or NH2 groups, or -OE6 is -(OCH2CH2)w OH or -(OCH2CH2)w OE21 where w is 1 to 12 and E21 is alkyl of 1 to 12 carbon atoms, E7 and E8 are independently hydrogen, alkyl of 1 to 18 carbon atoms, straight or branched chain C3-C18alkyl which is interrupted by -O-, -S- or -NE11-, C5-C12cycloalkyl, C6-C14aryl or C1-C3hydroxylalkyl, or E7 and E8 together with the N atom are a pyrrolidine, piperidine, piperazine or morpholine ring, E5 is -X-(Z)p-Y-E15 wherein X is -O- or -N(E16)-, Y is -O- or -N(E17)-, Z is C2-C12-alkylene, C4-C12-alkylene interrupted by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is C3-C12-alkylene, butenylene, butynylene, cyclohexylene or phenylene, each substituted by a hydroxyl group, m is zero, 1 or 2, p is 1, or p is also zero when X and Y are -N(E16)- and -N(E17)-, respectively, E15 is a group -CO-C(E18)=C(H)E19 or, when Y is -N(E17)-, forms together with E17 a group -CO-CH=CH-CO-, wherein E18 is hydrogen or methyl, and E19 is hydrogen, methyl or -CO-X-E20, wherein E20 is hydrogen, C1-C12-alkyl or a group of the formula wherein the symbols E1, G2, X, Z, m and p have the meanings defined above, and E16 and E17 independently of one another are hydrogen, C1-C12-alkyl, C3-C12-alkyl interrupted by 1 to
3 oxygen atoms, or is cyclohexyl or C7-C15aralkyl, and E16 together with E17 in the case where Z is ethylene, also forms ethylene, when n is 2, one of G2 is also hydrogen, E5 is one of divalent radicals -O-E9-O- or -N(E11)-E10-N(E11)-, E9 is C2-C8alkylene, C4-C8alkenylene, C4alkynylene, cyclohexylene, straight or branched chain C4-C10alkylene which is interrupted by -O- or by -CH2-CHOH-CH2-CH2-CHOH-CH2-, E10 being straight or branched chain C2-C12alkylene which may be interrupted by -O-, cyclohexylene, or or E10 and E11with the two nitrogen atoms form a piperazine ring, E14 is straight or branched chain C2-C8alkylene, straight or branched chain C4-C10alkylene which is interrupted by -O-, cycloalkylene, arylene or where E7 and E8 are independently hydrogen, alkyl of 1 to 18 carbon atoms or E7 and E8 together are alkylene of 4 to 6 carbon atoms, 3-oxapentamethylene, 3-iminopentamethylene or 3-methyliminopentamethylene, E11 is hydrogen, straight or branched chain C1-C18alkyl, C5-C12cycloalkyl, straight or branched chain C2-C18alkenyl, C6-C14aryl or C7-C15aralkyl, E12 is straight or branched chain C1-C18alkyl, straight or branched chain C3-C18alkenyl, C5-C10cycloalkyl, C6-C16aryl or C7-C15aralkyl, E13 is H, straight chain or branched C1-C18alkyl which is substituted by -PO(OE12)2, phenyl which is unsubstituted or substituted by OH, C7-C15aralkyl or -CH2OE12, E3 is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20 carbon atoms, alkyl substituted by alkoxycarbonyl of 2 to 9 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one or two alkyl of 1 to 4 carbon atoms or 1,1,2,2-tetrahydroperfluoroalkyl where the perfluoroalkyl moiety is of 6 to 16 carbon atoms, and L is alkylene of 1 to 12 carbon atoms, alkylidene of 2 to 12 carbon atoms, benzylidene, p-xylylene, a,a,a',a'-tetramethyl-m-xylylene or cycloalkylidene;
and with the proviso that formula (I) does not represent 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole, 5-chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole or 2-(2-hydroxy-3,5-di-.alpha.-cumyl)-2H-benzotriazole.
3. A plastic container or film according to claim 2 wherein said benzotriazole UV
absorbers are of formula (I) wherein G1 is hydrogen, G2 is hydrogen, cyano, chloro, fluoro, CF3-, -CO-G3, E3SO- or E3SO2-, G3 is straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, E1 is phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, E2 is straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; or E2 is said alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more -OH, -OCOE11, -OE4, -NCO, -NH2, -NHCOE11, -NHE4 or -N(E4)2, or mixtures thereof, where E4 is straight or branched chain alkyl of 1 to 24 carbon atoms; or said alkyl or said alkenyl interrupted by one or more -O-, -NH- or -NE4- groups or mixtures thereof and which can be unsubstituted or substituted by one or more -OH, -OE4 or -NH2 groups or mixtures thereof;
E3 is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one or two alkyl of 1 to 4 carbon atoms or 1,1,2,2-tetrahydroperfluoroalkyl where the perfluoroalkyl moiety is of 6 to 16 carbon atoms;
or is a compound of formula (I) wherein, G1 is hydrogen, G2 is chloro, fluoro, CF3-, E3SO- or E3SO2-, E1 is hydrogen or straight or branched alkyl of 1 to 24 carbon atoms, E2 is as defined above, and E3 is straight or branched chain alkyl of 1 to 7 carbon atoms; and with the proviso that formula (I) does not represent 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole, 5-chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole or 2-(2-hydroxy-3,5-di-.alpha.-cumyl)-2H-benzotriazole.
and with the proviso that formula (I) does not represent 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole, 5-chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole or 2-(2-hydroxy-3,5-di-.alpha.-cumyl)-2H-benzotriazole.
3. A plastic container or film according to claim 2 wherein said benzotriazole UV
absorbers are of formula (I) wherein G1 is hydrogen, G2 is hydrogen, cyano, chloro, fluoro, CF3-, -CO-G3, E3SO- or E3SO2-, G3 is straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, E1 is phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, E2 is straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; or E2 is said alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more -OH, -OCOE11, -OE4, -NCO, -NH2, -NHCOE11, -NHE4 or -N(E4)2, or mixtures thereof, where E4 is straight or branched chain alkyl of 1 to 24 carbon atoms; or said alkyl or said alkenyl interrupted by one or more -O-, -NH- or -NE4- groups or mixtures thereof and which can be unsubstituted or substituted by one or more -OH, -OE4 or -NH2 groups or mixtures thereof;
E3 is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one or two alkyl of 1 to 4 carbon atoms or 1,1,2,2-tetrahydroperfluoroalkyl where the perfluoroalkyl moiety is of 6 to 16 carbon atoms;
or is a compound of formula (I) wherein, G1 is hydrogen, G2 is chloro, fluoro, CF3-, E3SO- or E3SO2-, E1 is hydrogen or straight or branched alkyl of 1 to 24 carbon atoms, E2 is as defined above, and E3 is straight or branched chain alkyl of 1 to 7 carbon atoms; and with the proviso that formula (I) does not represent 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole, 5-chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole or 2-(2-hydroxy-3,5-di-.alpha.-cumyl)-2H-benzotriazole.
4. A plastic container or film according to claim 2 wherein said benzotriazole UV
absorbers of formula (II) are of the formula (IIA) wherein G1 is hydrogen, G2 is CF3- or fluoro, E1 is hydrogen, straight or branched alkyl of 1 to 24 carbon atoms or phenylalkyl of 7 to 15 carbon atoms, when E1 is phenylalkyl of 7 to 15 carbon atoms, G2 may also be hydrogen, E5 is -OE6 or -NE7E8, or E5 is -X-(Z)p-Y-E15 wherein X is -O- or -N(E16)-, Y is -O- or -N(E17)-, Z is C2-C12-alkylene, C4-C12-alkylene interrupted by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is C3-C12-alkylene, butenylene, butynylene, cyclohexylene or phenylene, each substituted by a hydroxyl group, m is 0, 1, 2 or 3, p is 1, or p is also zero when X and Y are -N(E16)- and -N(E17)-, respectively, E15 is a group -CO-C(E18)=C(H)E19 or, when Y is -N(E17)-, forms together with E17 a group -CO-CH=CH-CO-, wherein E18 is hydrogen or methyl, and E19 is hydrogen, methyl or -CO-X-E20, wherein E20 is hydrogen, C1-C12-alkyl or a group of the formula
absorbers of formula (II) are of the formula (IIA) wherein G1 is hydrogen, G2 is CF3- or fluoro, E1 is hydrogen, straight or branched alkyl of 1 to 24 carbon atoms or phenylalkyl of 7 to 15 carbon atoms, when E1 is phenylalkyl of 7 to 15 carbon atoms, G2 may also be hydrogen, E5 is -OE6 or -NE7E8, or E5 is -X-(Z)p-Y-E15 wherein X is -O- or -N(E16)-, Y is -O- or -N(E17)-, Z is C2-C12-alkylene, C4-C12-alkylene interrupted by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is C3-C12-alkylene, butenylene, butynylene, cyclohexylene or phenylene, each substituted by a hydroxyl group, m is 0, 1, 2 or 3, p is 1, or p is also zero when X and Y are -N(E16)- and -N(E17)-, respectively, E15 is a group -CO-C(E18)=C(H)E19 or, when Y is -N(E17)-, forms together with E17 a group -CO-CH=CH-CO-, wherein E18 is hydrogen or methyl, and E19 is hydrogen, methyl or -CO-X-E20, wherein E20 is hydrogen, C1-C12-alkyl or a group of the formula
5. A plastic container or film according to claim 2 wherein said benzotriazole UV
absorbers are of formula (III) are of the formula (IIIA) wherein G2 is CF3, G2' is hydrogen or CF3, E2 and E2' are independently straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; and L is alkylene of 1 to 12 carbon atoms, alkylidene of 2 to 12 carbon atoms, benzylidene, p-xylylene, a,a,a',a'-tetramethyl-m-xylylene or cycloalkylidene.
absorbers are of formula (III) are of the formula (IIIA) wherein G2 is CF3, G2' is hydrogen or CF3, E2 and E2' are independently straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; and L is alkylene of 1 to 12 carbon atoms, alkylidene of 2 to 12 carbon atoms, benzylidene, p-xylylene, a,a,a',a'-tetramethyl-m-xylylene or cycloalkylidene.
6. A plastic container or film according to claim 2 wherein said benzotriazole UV
absorbers are of formula (I) wherein G1 is hydrogen, G2 is CF3-, E1 is phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, E2 is straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; or E2 is said alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more -OH, -OCOE11, -NH2 or -NHCOE11, or mixtures thereof, or said alkyl or said alkenyl interrupted by one or more -O-and which can be unsubstituted or substituted by one or more -OH, or is a compound of formula (I) wherein, G1 is hydrogen, G2 is CF3-, E1 is hydrogen, straight or branched alkyl of 4 to 24 carbon atoms or phenylalkyl of 7 to 15 carbon atoms, and E2 is straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; or E2 is said alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more -OH, -OCOE11, -NH2 or -NHCOE11, or mixtures thereof, or said alkyl or said alkenyl interrupted by one or more -O-and which can be unsubstituted or substituted by one or more -OH.
absorbers are of formula (I) wherein G1 is hydrogen, G2 is CF3-, E1 is phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, E2 is straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; or E2 is said alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more -OH, -OCOE11, -NH2 or -NHCOE11, or mixtures thereof, or said alkyl or said alkenyl interrupted by one or more -O-and which can be unsubstituted or substituted by one or more -OH, or is a compound of formula (I) wherein, G1 is hydrogen, G2 is CF3-, E1 is hydrogen, straight or branched alkyl of 4 to 24 carbon atoms or phenylalkyl of 7 to 15 carbon atoms, and E2 is straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; or E2 is said alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more -OH, -OCOE11, -NH2 or -NHCOE11, or mixtures thereof, or said alkyl or said alkenyl interrupted by one or more -O-and which can be unsubstituted or substituted by one or more -OH.
7. A plastic container or film according to claim 2 wherein said benzotriazole UV
absorbers of formula (II) are of the formula (IIA) wherein G1 is hydrogen, G2 is CF3-, E1 is hydrogen, straight or branched alkyl of 4 to 24 carbon atoms or phenylalkyl of 7 to 15 carbon atoms, E5 is -OE6 or -NE7E8 where E6 is hydrogen, straight or branched chain C1-C24alkyl which is unsubstituted or substituted by one or more OH groups, or -OE6 is -(OCH2CH2)w OH or -(OCH2CH2)w OE21where w is 1 to 12 and E21 is alkyl of 1 to 12 carbon atoms, and E7 and E8 are independently hydrogen, alkyl of 1 to 18 carbon atoms, straight or branched chain C3-C18alkyl which is interrupted by -O-, -S- or -NE11-, C5-C12cycloalkyl, C6-C14aryl or C1-C3hydroxylalkyl, or E7 and E8 together with the N atom are a pyrrolidine, piperidine, piperazine or morpholine ring.
absorbers of formula (II) are of the formula (IIA) wherein G1 is hydrogen, G2 is CF3-, E1 is hydrogen, straight or branched alkyl of 4 to 24 carbon atoms or phenylalkyl of 7 to 15 carbon atoms, E5 is -OE6 or -NE7E8 where E6 is hydrogen, straight or branched chain C1-C24alkyl which is unsubstituted or substituted by one or more OH groups, or -OE6 is -(OCH2CH2)w OH or -(OCH2CH2)w OE21where w is 1 to 12 and E21 is alkyl of 1 to 12 carbon atoms, and E7 and E8 are independently hydrogen, alkyl of 1 to 18 carbon atoms, straight or branched chain C3-C18alkyl which is interrupted by -O-, -S- or -NE11-, C5-C12cycloalkyl, C6-C14aryl or C1-C3hydroxylalkyl, or E7 and E8 together with the N atom are a pyrrolidine, piperidine, piperazine or morpholine ring.
8. A plastic container or film according to claim 2 wherein said benzotriazole UV
absorbers of formula (III) are of the formula (IIIA) wherein G2 is CF3, G2' is hydrogen or CF3, E2 and E2' are independently straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; and L is methylene.
absorbers of formula (III) are of the formula (IIIA) wherein G2 is CF3, G2' is hydrogen or CF3, E2 and E2' are independently straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; and L is methylene.
9. A plastic container or film according to claim 1 wherein said tris-aryl-s-triazine UV
absorbers are of formula (IV), (V), (VI), (VII), (VIII) or (IX) wherein X and Y are independently phenyl, naphthyl, or said phenyl or said naphthyl substituted by one to three alkyl of 1 to 6 carbon atoms, by halogen, by hydroxy or by alkoxy of 1 to 6 carbon atoms or by mixtures thereof; or X and Y are independently Z1 or Z2;
R1 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, cycloalkyl of to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, halogen, -SR3, -SOR3 or -SO2R3;
or said alkyl, said cycloalkyl or said phenylalkyl substituted by one to three halogen, -R4, -OR5, -N(R5)2, -COR5, -COOR5, -OCOR5, -CN, -NO2, -SR5, -SOR5, -SO2R5 or -P(O)(OR5)2, morpholinyl, piperidinyl, 2,2,6,6-tetramethylpiperidinyl, piperazinyl or N-methylpiperidinyl groups or combinations thereof; or said alkyl or said cycloalkyl interrupted by one to four phenylene, -O-, -NR5-, -CONR5-, -COO-, -OCO- or -CO groups or combinations thereof; or said alkyl or said cycloalkyl both substituted and interrupted by combinations of the groups mentioned above;
R3 is alkyl of 1 to 20 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one or two alkyl of 1 to 4 carbon atoms;
R4 is aryl of 6 to 10 carbon atoms or said aryl substituted by one to three halogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms or combinations thereof;
cycloalkyl of 5 to 12 carbon atoms; phenylalkyl of 7 to 15 carbon atoms or said phenylalkyl substituted on the phenyl ring by one to three halogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms or combinations thereof; or straight or branched chain alkenyl of 2 to 18 carbon atoms;
R5 is defined as is R4; or R5 is also hydrogen or straight or branched chain alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms; or R5 is a group for formula T is hydrogen, oxyl, hydroxyl, -OT1, alkyl of 1 to 24 carbon atoms, said alkyl substituted by one to three hydroxy; benzyl or alkanoyl of 2 to 18 carbon atoms;
T1 is alkyl of 1 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, alkenyl of 2 to 24 carbon atoms, cycloalkenyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, a radical of a saturated or unsaturated bicyclic or tricyclic hydrocarbon of 7 to 12 carbon atoms or aryl of 6 o 10 carbon atoms or said aryl substituted by one to three alkyl of 1 to 4 carbon atoms;
R2 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms or cycloalkyl of 5 to 12 carbon atoms; or said alkyl or said cycloalkyl substitute by one to four halogen, epoxy, glycidyloxy, furyloxy, -R4, -OR5, -N(R5)2, -CON(R5)2, -COR5, -COOR5, -OCOR5, -OCOC(R5)=C(R5)2, -C(R5)=CCOOR5, -CN, -NCO, or or combinations thereof; or said alkyl or said cycloalkyl interrupted by one to four epoxy, -O-, -NR5-, -CONR5-, -COO-, -OCO-, -CO-, -C(R5)=C(R5)COO-, -OCOC(R5)=C(R5)-, -C(R5)=C(R5)-, phenylene or phenylene-G-phenylene in which G is -O-, -S-, -SO2-, -CH2- or -C(CH3)2- or combinations thereof, or said alkyl or said cycloalkyl both substituted and interrupted by combinations of the groups mentioned above; or R2 is -SO2R3 or -COR6;
R6 is straight or branched chain alkyl of 1 to 18 carbon atoms, straight or branched chain alkenyl of 2 to 12 carbon atoms, phenoxy, alkylamino of 1 to 12 carbon atoms, arylamino of 6 to 12 carbon atoms, -R7COOH or -NH-R8-NCO;
R7 is alkylene of 2 to 14 carbon atoms or phenylene;
R8 is alkylene of 2 to 24 carbon atoms, phenylene, tolylene, diphenylmethane or a group R1' and R1" are the same or different and are as defined for R1;
R2' and R2" are the same or different and are as defined for R2;
X, X', Y and Y' are the same or different and are as defined for X and Y;
t is 0 to 9;
L is straight or branched alkylene of 1 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms or alkylene substituted or interrupted by cyclohexylene or phenylene; or L is benzylidene; or L is -S-, -S-S-, -S-E-S-, -SO-, -SO2-, -SO-E-SO-, -SO2-E-SO2-, NH-CH2- or E is alkylene of 2 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms or alkylene interrupted or terminated by cycloalkylene of 5 to 12 carbon atoms;
n is 2, 3 or 4;
when n is 2; Q is straight or branched alkylene of 2 to 16 carbon atoms; or said alkylene substituted by one to three hydroxy groups; or said alkylene interrupted by one to three -CH=CH- or -O-; or said alkylene both substituted and interrupted by combinations of the groups mentioned above; or Q is xylylene or a group -CONH-R8-NHCO-, -CH2CH(OH)CH2O-R9-OCH2CH(OH)CH2-, -CO-R10-CO-, or-(CH2)m-COO-R11-OOC-(CH2)m-, where m is 1 to 3;
or Q is R9 is alkylene of 2 to 50 carbon atoms; or said alkylene interrupted by one to ten -O-, phenylene or a group -phenylene-G-phenylene in which G is -O-, -S-, -SO2-, -CH2- or -C(CH3)2-;
R10 is alkylene of 2 to 10 carbon atoms, or said alkylene interrupted by one to four -O--S- or -CH=CH-; or R10 is arylene of 6 to 12 carbon atoms;
R11 is alkylene of 2 to 20 carbon atoms or said alkylene interrupted by one to eight -O-;
when n is 3, Q is a group -[(CH2)m COO]3-R12 where m is 1 to 3, and R12 is an alkanetriyl of 3 to 12 carbon atoms;
when n is 4, Q is a group -[(CH2)m COO]4-R13 where m is 1 to 3, and R14 is an alkanetetrayl of 4 to 12 carbon atoms;
Z1 is a group of formula Z2 is a group of formula where r1 and r2 are independently of each other 0 or 1;
R14, R15, R16, R17, R18, R19, R20, R21, R22 and R23 are independently of one another hydrogen, hydroxy, cyano, alkyl of 1 to 20 carbon atoms, alkoxy of 1 to 20 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms, halogen, haloalkyl of 1 to 5 carbon atoms, sulfo, carboxy, acylamino of 2 to 12 carbon atoms, acyloxy of 2 to 12 carbon atoms, alkoxycarbonyl of 2 to 12 carbon atoms or aminocarbonyl; or R17 and R18 or R22 and R23 together with the phenyl radical to which they are attached are a cyclic radical interrupted by one to three -O-or -NR5-;
with the proviso that the compound of formula (IV) is not 4,6-diphenyl-2-(4-hexyloxy-2-hydroxyphenyl)-s-triazine.
absorbers are of formula (IV), (V), (VI), (VII), (VIII) or (IX) wherein X and Y are independently phenyl, naphthyl, or said phenyl or said naphthyl substituted by one to three alkyl of 1 to 6 carbon atoms, by halogen, by hydroxy or by alkoxy of 1 to 6 carbon atoms or by mixtures thereof; or X and Y are independently Z1 or Z2;
R1 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, cycloalkyl of to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, halogen, -SR3, -SOR3 or -SO2R3;
or said alkyl, said cycloalkyl or said phenylalkyl substituted by one to three halogen, -R4, -OR5, -N(R5)2, -COR5, -COOR5, -OCOR5, -CN, -NO2, -SR5, -SOR5, -SO2R5 or -P(O)(OR5)2, morpholinyl, piperidinyl, 2,2,6,6-tetramethylpiperidinyl, piperazinyl or N-methylpiperidinyl groups or combinations thereof; or said alkyl or said cycloalkyl interrupted by one to four phenylene, -O-, -NR5-, -CONR5-, -COO-, -OCO- or -CO groups or combinations thereof; or said alkyl or said cycloalkyl both substituted and interrupted by combinations of the groups mentioned above;
R3 is alkyl of 1 to 20 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one or two alkyl of 1 to 4 carbon atoms;
R4 is aryl of 6 to 10 carbon atoms or said aryl substituted by one to three halogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms or combinations thereof;
cycloalkyl of 5 to 12 carbon atoms; phenylalkyl of 7 to 15 carbon atoms or said phenylalkyl substituted on the phenyl ring by one to three halogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms or combinations thereof; or straight or branched chain alkenyl of 2 to 18 carbon atoms;
R5 is defined as is R4; or R5 is also hydrogen or straight or branched chain alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms; or R5 is a group for formula T is hydrogen, oxyl, hydroxyl, -OT1, alkyl of 1 to 24 carbon atoms, said alkyl substituted by one to three hydroxy; benzyl or alkanoyl of 2 to 18 carbon atoms;
T1 is alkyl of 1 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, alkenyl of 2 to 24 carbon atoms, cycloalkenyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, a radical of a saturated or unsaturated bicyclic or tricyclic hydrocarbon of 7 to 12 carbon atoms or aryl of 6 o 10 carbon atoms or said aryl substituted by one to three alkyl of 1 to 4 carbon atoms;
R2 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms or cycloalkyl of 5 to 12 carbon atoms; or said alkyl or said cycloalkyl substitute by one to four halogen, epoxy, glycidyloxy, furyloxy, -R4, -OR5, -N(R5)2, -CON(R5)2, -COR5, -COOR5, -OCOR5, -OCOC(R5)=C(R5)2, -C(R5)=CCOOR5, -CN, -NCO, or or combinations thereof; or said alkyl or said cycloalkyl interrupted by one to four epoxy, -O-, -NR5-, -CONR5-, -COO-, -OCO-, -CO-, -C(R5)=C(R5)COO-, -OCOC(R5)=C(R5)-, -C(R5)=C(R5)-, phenylene or phenylene-G-phenylene in which G is -O-, -S-, -SO2-, -CH2- or -C(CH3)2- or combinations thereof, or said alkyl or said cycloalkyl both substituted and interrupted by combinations of the groups mentioned above; or R2 is -SO2R3 or -COR6;
R6 is straight or branched chain alkyl of 1 to 18 carbon atoms, straight or branched chain alkenyl of 2 to 12 carbon atoms, phenoxy, alkylamino of 1 to 12 carbon atoms, arylamino of 6 to 12 carbon atoms, -R7COOH or -NH-R8-NCO;
R7 is alkylene of 2 to 14 carbon atoms or phenylene;
R8 is alkylene of 2 to 24 carbon atoms, phenylene, tolylene, diphenylmethane or a group R1' and R1" are the same or different and are as defined for R1;
R2' and R2" are the same or different and are as defined for R2;
X, X', Y and Y' are the same or different and are as defined for X and Y;
t is 0 to 9;
L is straight or branched alkylene of 1 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms or alkylene substituted or interrupted by cyclohexylene or phenylene; or L is benzylidene; or L is -S-, -S-S-, -S-E-S-, -SO-, -SO2-, -SO-E-SO-, -SO2-E-SO2-, NH-CH2- or E is alkylene of 2 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms or alkylene interrupted or terminated by cycloalkylene of 5 to 12 carbon atoms;
n is 2, 3 or 4;
when n is 2; Q is straight or branched alkylene of 2 to 16 carbon atoms; or said alkylene substituted by one to three hydroxy groups; or said alkylene interrupted by one to three -CH=CH- or -O-; or said alkylene both substituted and interrupted by combinations of the groups mentioned above; or Q is xylylene or a group -CONH-R8-NHCO-, -CH2CH(OH)CH2O-R9-OCH2CH(OH)CH2-, -CO-R10-CO-, or-(CH2)m-COO-R11-OOC-(CH2)m-, where m is 1 to 3;
or Q is R9 is alkylene of 2 to 50 carbon atoms; or said alkylene interrupted by one to ten -O-, phenylene or a group -phenylene-G-phenylene in which G is -O-, -S-, -SO2-, -CH2- or -C(CH3)2-;
R10 is alkylene of 2 to 10 carbon atoms, or said alkylene interrupted by one to four -O--S- or -CH=CH-; or R10 is arylene of 6 to 12 carbon atoms;
R11 is alkylene of 2 to 20 carbon atoms or said alkylene interrupted by one to eight -O-;
when n is 3, Q is a group -[(CH2)m COO]3-R12 where m is 1 to 3, and R12 is an alkanetriyl of 3 to 12 carbon atoms;
when n is 4, Q is a group -[(CH2)m COO]4-R13 where m is 1 to 3, and R14 is an alkanetetrayl of 4 to 12 carbon atoms;
Z1 is a group of formula Z2 is a group of formula where r1 and r2 are independently of each other 0 or 1;
R14, R15, R16, R17, R18, R19, R20, R21, R22 and R23 are independently of one another hydrogen, hydroxy, cyano, alkyl of 1 to 20 carbon atoms, alkoxy of 1 to 20 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms, halogen, haloalkyl of 1 to 5 carbon atoms, sulfo, carboxy, acylamino of 2 to 12 carbon atoms, acyloxy of 2 to 12 carbon atoms, alkoxycarbonyl of 2 to 12 carbon atoms or aminocarbonyl; or R17 and R18 or R22 and R23 together with the phenyl radical to which they are attached are a cyclic radical interrupted by one to three -O-or -NR5-;
with the proviso that the compound of formula (IV) is not 4,6-diphenyl-2-(4-hexyloxy-2-hydroxyphenyl)-s-triazine.
10. A plastic container or film according to claim 9 wherein said tris-aryl-s-triazine UV
absorbers are of the formula (IV) where X and Y are the same or different and are phenyl or said phenyl substituted by one to three alkyl of 1 to 6 carbon atoms, halogen, hydroxy or alkoxy of 1 to 12 carbon atoms; or X and Y are Z1 or Z2;
R1 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, cycloalkyl of to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms or halogen;
R2 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms or cycloalkyl of 5 to 12 carbon atoms; or said alkyl or said cycloalkyl substituted by one to three -R4, -OR5, -COOR5, -OCOR5 or combinations thereof; or said alkyl or cycloalkyl interrupted by one to three epoxy, -O-, -COO-, -OCO- or -CO-;
R4 is aryl of 6 to 10 carbon atoms or said aryl substituted by one to three halogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms or combinations thereof;
cycloalkyl of 5 to 12 carbon atoms; phenylalkyl of 7 to 15 carbon atoms or said phenylalkyl substituted on the phenyl ring by one to three halogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms or combinations thereof;
R5 is defined as is R4; or R5 is also hydrogen or straight or branched chain alkyl of 1 to 24 carbon atoms;
Z1 is a group of formula Z2 is a group of formula where r1 and r2 are each 1; and R14, R15, R16, R17, R18, R19, R20, R21, R22 and R23 are independently of one another hydrogen, hydroxy, cyano, alkyl of 1 to 20 carbon atoms, alkoxy of 1 to 20 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms, halogen, haloalkyl of 1 to 5 carbon atoms, sulfo, carboxy, acylamino of 2 to 12 carbon atoms, acyloxy of 2 to 12 carbon atoms, or alkoxycarbonyl of 2 to 12 carbon atoms or aminocarbonyl;
with the proviso that the compound of formula (IV) is not 4,6-diphenyl-2-(4-hexyloxy-2-hydroxyphenyl)-s-triazine.
absorbers are of the formula (IV) where X and Y are the same or different and are phenyl or said phenyl substituted by one to three alkyl of 1 to 6 carbon atoms, halogen, hydroxy or alkoxy of 1 to 12 carbon atoms; or X and Y are Z1 or Z2;
R1 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, cycloalkyl of to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms or halogen;
R2 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms or cycloalkyl of 5 to 12 carbon atoms; or said alkyl or said cycloalkyl substituted by one to three -R4, -OR5, -COOR5, -OCOR5 or combinations thereof; or said alkyl or cycloalkyl interrupted by one to three epoxy, -O-, -COO-, -OCO- or -CO-;
R4 is aryl of 6 to 10 carbon atoms or said aryl substituted by one to three halogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms or combinations thereof;
cycloalkyl of 5 to 12 carbon atoms; phenylalkyl of 7 to 15 carbon atoms or said phenylalkyl substituted on the phenyl ring by one to three halogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms or combinations thereof;
R5 is defined as is R4; or R5 is also hydrogen or straight or branched chain alkyl of 1 to 24 carbon atoms;
Z1 is a group of formula Z2 is a group of formula where r1 and r2 are each 1; and R14, R15, R16, R17, R18, R19, R20, R21, R22 and R23 are independently of one another hydrogen, hydroxy, cyano, alkyl of 1 to 20 carbon atoms, alkoxy of 1 to 20 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms, halogen, haloalkyl of 1 to 5 carbon atoms, sulfo, carboxy, acylamino of 2 to 12 carbon atoms, acyloxy of 2 to 12 carbon atoms, or alkoxycarbonyl of 2 to 12 carbon atoms or aminocarbonyl;
with the proviso that the compound of formula (IV) is not 4,6-diphenyl-2-(4-hexyloxy-2-hydroxyphenyl)-s-triazine.
11. A plastic container or film according to claim 9 wherein said tris-aryl-s-triazine UV
absorbers are of the formula (V) wherein X is phenyl, naphthyl or said phenyl or said naphthyl substituted by one to three alkyl of 1 to 6 carbon atoms, by halogen, by hydroxy or by alkoxy of 1 to 6 carbon atoms or by mixtures thereof; or X is Z1.
absorbers are of the formula (V) wherein X is phenyl, naphthyl or said phenyl or said naphthyl substituted by one to three alkyl of 1 to 6 carbon atoms, by halogen, by hydroxy or by alkoxy of 1 to 6 carbon atoms or by mixtures thereof; or X is Z1.
12. A plastic container or film according to claim 9 wherein said tris-aryl-s-triazine UV
absorbers are of the formula (VI).
absorbers are of the formula (VI).
13. A plastic container or film according to claim 9 wherein said tris-aryl-s-triazine UV
absorbers are of the formula (IX) wherein X and Y are independently phenyl or said phenyl substituted by one to three alkyl of 1 to 6 carbon atoms, by halogen, by hydroxy or by alkoxy of 1 to 6 carbon atoms or by mixtures thereof; or X and Y are independently Z1 or Z2; and L is straight or branched alkylene of 1 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms or alkylene substituted or interrupted by cyclohexylene or phenylene.
absorbers are of the formula (IX) wherein X and Y are independently phenyl or said phenyl substituted by one to three alkyl of 1 to 6 carbon atoms, by halogen, by hydroxy or by alkoxy of 1 to 6 carbon atoms or by mixtures thereof; or X and Y are independently Z1 or Z2; and L is straight or branched alkylene of 1 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms or alkylene substituted or interrupted by cyclohexylene or phenylene.
14. A plastic container or film according to claim 9 wherein said tris-aryl-s-triazine UV
absorbers are of the formula (IV) wherein X and Y are the same or different and are phenyl or said phenyl substituted by one to three alkyl of 1 to 6 carbon atoms; Z1 or Z2;
R1 is hydrogen or phenylalkyl of 7 to 15 carbon atoms;
R2 is hydrogen, straight or branched chain alkyl of 1 to 18 carbon atoms; or said alkyl substituted by one to three -R4, -OR5 or mixtures thereof; or said alkyl interrupted by one to eight -O- or -COO-;
R4 is aryl of 6 to 10 carbon atoms;
R5 is hydrogen;
Z1 is a group of formula Z2 is a group of formula where r1 and r2 are each 1; and R14, R15, R16, R17, R18, R19, R20, R21, R22 and R23 are each hydrogen;
with the proviso that the compound of formula (IV) is not 4,6-diphenyl-2-(4-hexyloxy-2-hydroxyphenyl)-s-triazine.
absorbers are of the formula (IV) wherein X and Y are the same or different and are phenyl or said phenyl substituted by one to three alkyl of 1 to 6 carbon atoms; Z1 or Z2;
R1 is hydrogen or phenylalkyl of 7 to 15 carbon atoms;
R2 is hydrogen, straight or branched chain alkyl of 1 to 18 carbon atoms; or said alkyl substituted by one to three -R4, -OR5 or mixtures thereof; or said alkyl interrupted by one to eight -O- or -COO-;
R4 is aryl of 6 to 10 carbon atoms;
R5 is hydrogen;
Z1 is a group of formula Z2 is a group of formula where r1 and r2 are each 1; and R14, R15, R16, R17, R18, R19, R20, R21, R22 and R23 are each hydrogen;
with the proviso that the compound of formula (IV) is not 4,6-diphenyl-2-(4-hexyloxy-2-hydroxyphenyl)-s-triazine.
15. A plastic container or film according to claim 1 which comprises at least one hydroxyphenyl benzotriazole and at least one tris-aryl-s-triazine or a mixture of two or more hydroxyphenyl benzotriazoles or two or more tris-aryl-s-triazines.
16. A packaging material according to claim 1 wherein the UV absorbers of component (b) are incorporated into a coating applied to the outer surface of the packaging material.
17. A plastic container or film according to claim 1 in which the UV absorbers of component (b) are present from 0.1 to 20 % by weight based on the weight of the plastic container or film.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17956700P | 2000-02-01 | 2000-02-01 | |
| US60/179,567 | 2000-02-01 | ||
| PCT/EP2001/000694 WO2001057124A2 (en) | 2000-02-01 | 2001-01-23 | Method of content protection with durable uv absorbers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2396221A1 true CA2396221A1 (en) | 2001-08-09 |
| CA2396221C CA2396221C (en) | 2010-03-23 |
Family
ID=22657115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2396221A Expired - Fee Related CA2396221C (en) | 2000-02-01 | 2001-01-23 | Method of content protection with durable uv absorbers |
Country Status (13)
| Country | Link |
|---|---|
| US (4) | US20020028861A1 (en) |
| EP (1) | EP1252226B1 (en) |
| JP (1) | JP4681193B2 (en) |
| KR (1) | KR100689232B1 (en) |
| CN (1) | CN1180008C (en) |
| AT (1) | ATE353353T1 (en) |
| AU (1) | AU780351B2 (en) |
| BR (2) | BR0117305B1 (en) |
| CA (1) | CA2396221C (en) |
| DE (1) | DE60126476T8 (en) |
| MX (2) | MX229551B (en) |
| RU (1) | RU2266306C2 (en) |
| WO (1) | WO2001057124A2 (en) |
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-
2001
- 2001-01-23 AU AU44106/01A patent/AU780351B2/en not_active Ceased
- 2001-01-23 BR BRPI0117305-7A patent/BR0117305B1/en not_active IP Right Cessation
- 2001-01-23 DE DE60126476T patent/DE60126476T8/en active Active
- 2001-01-23 KR KR1020027009228A patent/KR100689232B1/en not_active IP Right Cessation
- 2001-01-23 MX MXPA02007355 patent/MX229551B/en active IP Right Grant
- 2001-01-23 JP JP2001557952A patent/JP4681193B2/en not_active Expired - Fee Related
- 2001-01-23 AT AT01916950T patent/ATE353353T1/en active
- 2001-01-23 CA CA2396221A patent/CA2396221C/en not_active Expired - Fee Related
- 2001-01-23 WO PCT/EP2001/000694 patent/WO2001057124A2/en active IP Right Grant
- 2001-01-23 BR BRPI0108013-0A patent/BR0108013B1/en not_active IP Right Cessation
- 2001-01-23 CN CNB018043992A patent/CN1180008C/en not_active Expired - Fee Related
- 2001-01-23 RU RU2002123360/04A patent/RU2266306C2/en not_active IP Right Cessation
- 2001-01-23 EP EP01916950A patent/EP1252226B1/en not_active Expired - Lifetime
- 2001-01-29 US US09/772,245 patent/US20020028861A1/en not_active Abandoned
-
2002
- 2002-07-30 MX MXPA05001128 patent/MX257080A/en unknown
- 2002-11-15 US US10/295,313 patent/US6746739B2/en not_active Expired - Lifetime
- 2002-12-18 US US10/323,238 patent/US6797751B2/en not_active Expired - Lifetime
-
2004
- 2004-03-30 US US10/812,722 patent/US7288583B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1427866A (en) | 2003-07-02 |
| DE60126476D1 (en) | 2007-03-22 |
| AU780351B2 (en) | 2005-03-17 |
| WO2001057124A3 (en) | 2002-01-17 |
| BR0108013A (en) | 2002-10-29 |
| US20030144389A1 (en) | 2003-07-31 |
| BR0108013B1 (en) | 2011-05-03 |
| EP1252226B1 (en) | 2007-02-07 |
| DE60126476T2 (en) | 2007-11-29 |
| US6746739B2 (en) | 2004-06-08 |
| ATE353353T1 (en) | 2007-02-15 |
| AU4410601A (en) | 2001-08-14 |
| US6797751B2 (en) | 2004-09-28 |
| JP2003522242A (en) | 2003-07-22 |
| DE60126476T8 (en) | 2008-03-27 |
| MX257080A (en) | 2008-05-12 |
| MX229551B (en) | 2005-07-29 |
| RU2266306C2 (en) | 2005-12-20 |
| EP1252226A2 (en) | 2002-10-30 |
| CN1180008C (en) | 2004-12-15 |
| US20040191447A1 (en) | 2004-09-30 |
| US20030119950A1 (en) | 2003-06-26 |
| JP4681193B2 (en) | 2011-05-11 |
| KR100689232B1 (en) | 2007-03-02 |
| MXPA02007355A (en) | 2002-12-09 |
| US20020028861A1 (en) | 2002-03-07 |
| KR20020079784A (en) | 2002-10-19 |
| RU2002123360A (en) | 2004-01-10 |
| WO2001057124A2 (en) | 2001-08-09 |
| US7288583B2 (en) | 2007-10-30 |
| CA2396221C (en) | 2010-03-23 |
| BR0117305B1 (en) | 2013-02-05 |
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| MKLA | Lapsed |
Effective date: 20180123 |