WO2005047384A1 - Uv stabilizing additive composition - Google Patents
Uv stabilizing additive composition Download PDFInfo
- Publication number
- WO2005047384A1 WO2005047384A1 PCT/US2004/036602 US2004036602W WO2005047384A1 WO 2005047384 A1 WO2005047384 A1 WO 2005047384A1 US 2004036602 W US2004036602 W US 2004036602W WO 2005047384 A1 WO2005047384 A1 WO 2005047384A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydroxy
- bis
- triazine
- tetramethyl
- piperidinyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 59
- 230000000087 stabilizing effect Effects 0.000 title claims abstract description 21
- 239000000654 additive Substances 0.000 title description 26
- 230000000996 additive effect Effects 0.000 title description 16
- -1 amine compound Chemical class 0.000 claims abstract description 90
- 239000000463 material Substances 0.000 claims abstract description 33
- 239000012964 benzotriazole Substances 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 10
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 9
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 8
- NJPUGXZMKBZIQZ-UHFFFAOYSA-N 1,5-dioxaspiro[5.5]undecane-3,3-dicarboxylic acid Chemical compound O1CC(C(=O)O)(C(O)=O)COC11CCCCC1 NJPUGXZMKBZIQZ-UHFFFAOYSA-N 0.000 claims description 8
- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 229920000728 polyester Polymers 0.000 claims description 7
- BWJKLDGAAPQXGO-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-octadecoxypiperidine Chemical compound CCCCCCCCCCCCCCCCCCOC1CC(C)(C)NC(C)(C)C1 BWJKLDGAAPQXGO-UHFFFAOYSA-N 0.000 claims description 6
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 claims description 6
- 229920000058 polyacrylate Polymers 0.000 claims description 6
- 229920001470 polyketone Polymers 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- OUBISKKOUYNDML-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) 2-[bis[2-oxo-2-(2,2,6,6-tetramethylpiperidin-4-yl)oxyethyl]amino]acetate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CN(CC(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 OUBISKKOUYNDML-UHFFFAOYSA-N 0.000 claims description 4
- ZSSVCEUEVMALRD-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 ZSSVCEUEVMALRD-UHFFFAOYSA-N 0.000 claims description 4
- SAEZGDDJKSBNPT-UHFFFAOYSA-N 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)N(C)C(C)(C)C1 SAEZGDDJKSBNPT-UHFFFAOYSA-N 0.000 claims description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 229920000180 alkyd Polymers 0.000 claims description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 4
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 4
- 229920000647 polyepoxide Polymers 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 4
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 claims description 4
- 229920002397 thermoplastic olefin Polymers 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 3
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- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 3
- BUFCQVRLKYIQJP-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) prop-2-enoate Chemical compound CC1(C)CC(OC(=O)C=C)CC(C)(C)N1 BUFCQVRLKYIQJP-UHFFFAOYSA-N 0.000 claims description 2
- SXJSETSRWNDWPP-UHFFFAOYSA-N (2-hydroxy-4-phenylmethoxyphenyl)-phenylmethanone Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C(O)=CC=1OCC1=CC=CC=C1 SXJSETSRWNDWPP-UHFFFAOYSA-N 0.000 claims description 2
- JQSSXIRDGUMPNP-UHFFFAOYSA-N (4-decoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 JQSSXIRDGUMPNP-UHFFFAOYSA-N 0.000 claims description 2
- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 claims description 2
- VVEFXKUGUXUOSZ-UHFFFAOYSA-N (4-tert-butylphenyl)-(2,4-dihydroxyphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)C1=CC=C(O)C=C1O VVEFXKUGUXUOSZ-UHFFFAOYSA-N 0.000 claims description 2
- UONCERAQKBPLML-UHFFFAOYSA-N (6-ethoxypyridin-3-yl)boronic acid Chemical compound CCOC1=CC=C(B(O)O)C=N1 UONCERAQKBPLML-UHFFFAOYSA-N 0.000 claims description 2
- FFIJIFGRYNWQNQ-UHFFFAOYSA-N 1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrole-2,5-dione Chemical compound C1C(C)(C)NC(C)(C)CC1N1C(=O)C=CC1=O FFIJIFGRYNWQNQ-UHFFFAOYSA-N 0.000 claims description 2
- QSSWKPVVDJURMQ-UHFFFAOYSA-N 2,2,4,4,6-pentamethyl-1,3-diazinane Chemical compound CC1CC(C)(C)NC(C)(C)N1 QSSWKPVVDJURMQ-UHFFFAOYSA-N 0.000 claims description 2
- IVVLFHBYPHTMJU-UHFFFAOYSA-N 2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro[5.1.11^{8}.2^{6}]henicosan-21-one Chemical compound C1C(C)(C)NC(C)(C)CC21C(=O)NC1(CCCCCCCCCCC1)O2 IVVLFHBYPHTMJU-UHFFFAOYSA-N 0.000 claims description 2
- DCOZBPTXZNTCFM-UHFFFAOYSA-N 2,2-bis(2,2,6,6-tetramethyl-1-octoxypiperidin-3-yl)decanedioic acid Chemical compound CC1(C)N(OCCCCCCCC)C(C)(C)CCC1C(CCCCCCCC(O)=O)(C(O)=O)C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1 DCOZBPTXZNTCFM-UHFFFAOYSA-N 0.000 claims description 2
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 2
- BZQCIHBFVOTXRU-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-butoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 BZQCIHBFVOTXRU-UHFFFAOYSA-N 0.000 claims description 2
- SITYOOWCYAYOKL-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 SITYOOWCYAYOKL-UHFFFAOYSA-N 0.000 claims description 2
- DBYBHKQEHCYBQV-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-dodecoxyphenol Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 DBYBHKQEHCYBQV-UHFFFAOYSA-N 0.000 claims description 2
- LSNNLZXIHSJCIE-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-tridecoxyphenol Chemical compound OC1=CC(OCCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 LSNNLZXIHSJCIE-UHFFFAOYSA-N 0.000 claims description 2
- WPMUMRCRKFBYIH-UHFFFAOYSA-N 2-[4,6-bis(2-hydroxy-4-octoxyphenyl)-1,3,5-triazin-2-yl]-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(OCCCCCCCC)=CC=2)O)=NC(C=2C(=CC(OCCCCCCCC)=CC=2)O)=N1 WPMUMRCRKFBYIH-UHFFFAOYSA-N 0.000 claims description 2
- NPUPWUDXQCOMBF-UHFFFAOYSA-N 2-[4,6-bis(4-methylphenyl)-1,3,5-triazin-2-yl]-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C=CC(C)=CC=2)=NC(C=2C=CC(C)=CC=2)=N1 NPUPWUDXQCOMBF-UHFFFAOYSA-N 0.000 claims description 2
- PIGBIZGGEUNVCV-UHFFFAOYSA-N 2-[4,6-bis[4-(3-butoxy-2-hydroxypropoxy)-2-hydroxyphenyl]-1,3,5-triazin-2-yl]-5-(3-butoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCC)=CC=C1C1=NC(C=2C(=CC(OCC(O)COCCCC)=CC=2)O)=NC(C=2C(=CC(OCC(O)COCCCC)=CC=2)O)=N1 PIGBIZGGEUNVCV-UHFFFAOYSA-N 0.000 claims description 2
- HHIVRACNDKRDTF-UHFFFAOYSA-N 2-[4-(2,4-dimethylphenyl)-6-(2-hydroxy-4-propoxyphenyl)-1,3,5-triazin-2-yl]-5-propoxyphenol Chemical compound OC1=CC(OCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(OCCC)=CC=2)O)=N1 HHIVRACNDKRDTF-UHFFFAOYSA-N 0.000 claims description 2
- VARDNKCBWBOEBW-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazin-2-yl]phenol Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C(=CC=CC=2)O)=N1 VARDNKCBWBOEBW-UHFFFAOYSA-N 0.000 claims description 2
- SKMNWICOBCDSSQ-UHFFFAOYSA-N 2-[4-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2,6,6-tetramethylpiperidin-1-yl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCN2C(CC(CC2(C)C)OC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(C)C)=C1 SKMNWICOBCDSSQ-UHFFFAOYSA-N 0.000 claims description 2
- LUPQXHNQUVRJFK-UHFFFAOYSA-N 2-butyl-2-[(3,5-ditert-butyl-2-hydroxyphenyl)-bis(1,2,2,6,6-pentamethylpiperidin-3-yl)methyl]propanedioic acid Chemical compound CCCCC(C(=O)O)(C(=O)O)C(C1CCC(N(C1(C)C)C)(C)C)(C2CCC(N(C2(C)C)C)(C)C)C3=CC(=CC(=C3O)C(C)(C)C)C(C)(C)C LUPQXHNQUVRJFK-UHFFFAOYSA-N 0.000 claims description 2
- IXAKLSFFPBJWBS-UHFFFAOYSA-N 2-cycloundecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diazaspiro[4.5]decan-4-one Chemical compound C1C(C)(C)NC(C)(C)CC21C(=O)NC(C1CCCCCCCCCC1)O2 IXAKLSFFPBJWBS-UHFFFAOYSA-N 0.000 claims description 2
- NTKWXRSEJQGLRX-UHFFFAOYSA-N 2-hydrazinyl-2-oxo-n-(2,2,6,6-tetramethylpiperidin-4-yl)acetamide Chemical compound CC1(C)CC(NC(=O)C(=O)NN)CC(C)(C)N1 NTKWXRSEJQGLRX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- GUCMKIKYKIHUTM-UHFFFAOYSA-N 3,3,5,5-tetramethyl-1-[2-(3,3,5,5-tetramethyl-2-oxopiperazin-1-yl)ethyl]piperazin-2-one Chemical compound O=C1C(C)(C)NC(C)(C)CN1CCN1C(=O)C(C)(C)NC(C)(C)C1 GUCMKIKYKIHUTM-UHFFFAOYSA-N 0.000 claims description 2
- PZDBKXIJXWVRPZ-UHFFFAOYSA-N 3-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound C1C(C)(C)NC(C)(C)CC1C1C(=O)NC(=O)C1 PZDBKXIJXWVRPZ-UHFFFAOYSA-N 0.000 claims description 2
- FBIXXCXCZOZFCO-UHFFFAOYSA-N 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)NC(C)(C)C1 FBIXXCXCZOZFCO-UHFFFAOYSA-N 0.000 claims description 2
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- UNQWPCJRFXTMJT-UHFFFAOYSA-N n-cyclohexylmorpholin-4-amine Chemical compound C1CCCCC1NN1CCOCC1 UNQWPCJRFXTMJT-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010107 reaction injection moulding Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/132—Phenols containing keto groups, e.g. benzophenones
-
- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- 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
Definitions
- This invention relates to an improved UV stabilizing additive composition. More specifically, this invention relates to an UV stabilizing additive composition comprising an ortho-hydroxy triazine compound, a hindered amine compound and hydroxybenzophenone compound.
- UV ultraviolet
- Exposure to sunlight and other sources of ultraviolet (UV) radiation is known to cause degradation of a wide variety of materials, especially polymeric materials.
- polymeric materials such as plastics often discolor, lose gloss and/or become brittle as a result of prolonged exposure to UV light due primarily to a reduction in the molecular weight of the polymer.
- This invention relates to an UV stabilizing additive composition
- an UV stabilizing additive composition comprising an ortho- hydroxy triazine compound, a hindered amine compound and a hydroxybenzophenone compound.
- This additive composition may be used to stabilize materials from UV radiation.
- This invention also contemplates a method of stabilizing a material by contacting the material with the UV stabilizing additive composition.
- This invention relates to an UV stabilizing additive composition
- an ortho- hydroxy triazine compound a hindered amine light stabilizing (HALS) compound and a hydroxybenzophenone compound.
- HALS hindered amine light stabilizing
- the ortho-hydroxy tris-aryl-s-triazine compound has the following formula
- A, B and C are each aromatic, at least one of A, B and C is substituted by a hydroxy group ortho to the point of attachment to the triazine ring, and each of R through R 9 is selected from the group consisting of hydrogen, hydroxy, alkyl, alkoxy, sulfonic, carboxy, halo, haloalkyl and acylamino having from about 1 to about 24 carbon atoms.
- One embodiment of the tris-aryl-s-triazine is a compound having the formula II:
- Ari and Ar 2 are the same or different and are substituted or unsubstituted aryl groups; and where R 20 and R 2 ⁇ are each independently a hydrogen, C C 24 alkyl, C ⁇ -C 24 haloalkyl, C 6 -C 24 aryl, C 2 -C 24 alkenyl, C C 24 ac ⁇ , C ⁇ -C 24 cycloalkyl, C 5 -C 24 cycloacyl, C 7 -C 24 aralkyl, or C 6 -C 24 aracyl, substituted or unsubstituted biphenylene, substituted or unsubstituted napthalene, OR, NRR', CONRR', OCOR, CN, SR, S0 2 R, and where R and R' are each independently a hydrogen, C 1 -C 24 alkyl, C ⁇ -C 24 haloalkyl, C 6 -C 24 aryl, C 2 -C 24 alkenyl, C C 2 cycloalky
- R 22 and R 2 3 are each independently a hydrogen, C ⁇ -C 24 alkyl, C ⁇ -C 24 haloalkyl, C 6 -C 24 aryl, C 2 -C 24 alkenyl, C ⁇ -C 24 acyl, C 1 -C 24 cycloalkyl, C 5 -C 24 cycloacyl, C 7 -C 24 aralkyl, or C 6 -C 24 aracyl, substituted or unsubstituted biphenylene, substituted or unsubstituted napthalene, OR, NRR', CONRR', OCOR, CN, SR, and S0 2 R, and where R and R' are as defined above.
- R 20 is hydrogen or a C ⁇ -C 8 alkyl
- R 21 is hydrogen and Ar-i and Ar 2 may be the same or different and are benzyl, methylbenzyl, or dimethylbenzyl.
- suitable tris-aryl-s-triazines that may be used are 2,4,6-tris(2-hydroxy- 4-octyloxyphenyl)-1 ,3,5-triazine; 2-(2-hydroxy-4-n-octyloxyphenyl)-4,6-bis(2,4- dimethylphenyl)-1 ,3,5-triazine; 2-(2-hydroxy-4-(mixed iso-octyloxyphenyl)-4,6-bis(2,4- dimethylphenyl)-1 ,3,5-triazine; 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1 ,3,5- triazine; 2,4-bis(2-hydroxy-4-
- the hindered amine compound may be any suitable hindered amine compound such as those containing a 2,2,6,6-tetraalkylpiperdine or 2,2,6,6-tetraalkylpiperazinone radical.
- a hindered amine compound is one that contains at least one group having the following formula III:
- R-n is hydrogen, O, OH, C Ci8 alkyl, -CH 2 CN, C 1 -C 1 8 alkoxy, C C 18 hydroxyalkoxy, C 5 -C 12 cycloalkoxy, C5-C 12 hydrocycloalkoxy, C 3 -C 6 alkenyl, CrC 18 alkynyl, C 7 -C 9 phenylalkyl, unsubstituted or substituted on the phenyl with 1 , 2 or 3 C C 4 alkyls, or an aliphatic C C 8 acyl;
- R 12 is hydrogen, C-]-C 8 alkyl, or benzyl;
- R 1 3, R 14 , R 1 5, and R 16 are each independently a C C 18 alkyl, benzyl or phenethyl, or optionally R 13 and R 14 , and/or R- ⁇ 5 and R 16 , taken together with the carbon which they are attached, form a C5-C 1 0 cyclo
- R 10 is a morpholino, Ci -C 8 alkylamine, di(C ⁇ -C 8 ) alkylamine, pyrrolidyl, cyclohexylamine or combinations thereof,
- X and Xi which may be the same or different, and are hydrogen, Ci -C 20 alkyl, or a radical of formula III defined above,
- Z is a straight chained or branched CrC 20 alkylene or a straight chained or branched C
- Z is a C 2 to C 6 alkylene
- R 10 is a morpholino or cyclohexylamine
- X and Xi is the radical of formula III
- R-n is hydrogen or methyl
- R- ⁇ 2 is hydrogen
- R 13 , R 14 , R 15 and R 16 are methyl.
- Another embodiment of a hindered amine is a 2,2,6,6-tetraalkylpiperazinone.
- One embodiment of a 2,2,6,6-tetraalkylpiperazinone compound is one that contains at least one group of formula IVa:
- hindered amine compounds include, but are not limited to: 1 H-Pyrrole-2,5-dione, 1-octadecyl-, polymer with (l-methylethenyl)benzene and 1-(2,2,6,6- tetramethyl-4-piperidinyl)-1H-pyrrole-2,5-dione; piperazinone, 1 , ,1"-[1 ,3,5-triazine-2,4,6- triyltris[(cyclohexylimino)-2,1-ethanediyl]]tris[3,3,5,5-tetramethyl-]; piperazinone, 1,1',1"- [1,3,5-triazine-2,4,6-triyltris[(cyclohexylimino)-2,1-ethanediyl]]tris[3,3,4,5,5-pentamethyl-]; the reaction product of 7,7,
- R 17 , R 18 and R 2 are each independently hydrogen alkyl, aryl, aralkyl, alkaryl, alkoxy, aryloxy having from 1 to 18 carbon atoms and R 19 is hydrogen, a C C 2 alkyl, or substituted or unsubstituted C 6 -C 24 aryl.
- R 17 , R 18 and R 24 are each hydrogen and Rig is a C C 8 alkyl.
- Suitable hindered hydroxybenzophenone compounds include: 2,4-dihydroxybenzophenone; 2-hydroxy-4-methoxybenzophenone; 2-hydroxy-4- octyloxybenzophenone; 2-hydroxy-4-decyloxybenzophenone; 2-hydroxy-4- dodecyloxybenzophenone; 2-hydroxy-4-benzyloxybenzophenone; 2,2'-dihydroxy-4,4'- dimethoxybenzophenone; 2,2',4,4'-tetrahydroxybenzophenone; 2,4-dihydroxy-4'-tert-butyl- benzophenone; 1 ,6-bis-(3-hydroxy-4-benzoylphenoxy)hexane; methylenebis-(2-benzoyl-5- methoxyphenol).
- the UV stabilizing additive composition of the present invention may be employed to stabilize materials which are subject to degradation by ultraviolet radiation by contacting the UV stabilizing additive composition with a composition comprising polymeric or other materials, either chemically or physically.
- materials that may be so stabilized are polyolefins, polyesters, polyethers, polyketones, polyamides, natural and synthetic rubbers, polyurethanes, polystyrenes, high-impact polystyrenes, polyacrylates, polymethacrylates, polyacetals, polyacrylonitriles, polybutadienes, polystyrenes, acrylonitrile-butadiene-styrene, styrene acrylonitrile, acrylate styrene acrylonitrile, cellulosic acetate butyrate, cellulosic polymers, polyimides, polyamideimides, polyetherimides, polyphenylsulfides, polyphenyloxide, polys
- the materials to be stabilized are thermoplastic olefins, acrylonitrile- butadiene-styrene, polyesters, polyvinylchloride, polyamides, polyurethanes, or homo- and copolymers of propylene, isobutylene, butene, methylpentene, hexene, heptene, octene, isoprene, butadiene, hexadiene, dicyclopentadiene, ethylidene cyclopentene and norbomene. More preferably, the materials are polypropylene and thermoplastic olefins.
- the amount of the triazine compound used in the material to be stabilized using the combination of additives of the present invention is typically lower than normal usage.
- the lower limit of the amount of triazine may be as low as about 10 ppm, or about 20 ppm, or about 50 ppm or about 75 ppm or about 100 ppm or about 200 ppm, based on the amount of material to be stabilized.
- the amount of the hydroxybenzophenone compound used in the material to be stabilized using the combination of additives of the present invention is also typically lower than normal usage.
- the lower limit of the amount of hydroxybenzophenone may be as low as about 10 ppm, or about 20 ppm, or about 50 ppm or about 75 ppm or about 100 ppm or about 200 ppm, or about 500 ppm, based on the amount of material to be stabilized.
- There is no upper limit to the amount of hydroxybenzophenone but it would be about 5000 ppm or about 4000 ppm or about 3000 ppm or about 2000 ppm or about 1000 ppm or about 500 ppm, based on the material to be stabilized.
- the amount of the hindered amine compound used in the material to be stabilized using the combination of additives of the present invention is more or less than its typically used amount.
- the lower limit of the amount of hindered amine compound may be about 250 ppm, or about 500 ppm, or about 1000 ppm or about 2000 ppm, based on the amount of material to be stabilized.
- the amount of hindered amine compound with respect to the other UV absorbers is typically greater.
- the ratio of hindered amine compound to the triazine UV absorber may be as high as about 50:1 , or about 25:1, or about 20:1 or about 10:1 , or about 7:1 or about 3:1.
- the ratio of hindered amine compound to the hydroxybenzophenone UV absorber may be about 25:1 , or about 20:1 or about 10:1 , or about 7:1 or about 3:1 or about 2:1 or about 1.5:1 or about 1 :1.
- the ratio of hydroxybenzophenone compound to the triazine UV absorber may be about 10: 1 , or about 5: 1 , or about 3: 1 or about 2: 1 , or about 1 : 1 or about 1:2. It should be noted that the amounts and ratios disclosed for the above additives are each independent of each other. This invention contemplates that a benzotriazole UV absorber may be substituted for the hydroxybenzophenone UV absorber. The benzotriazole compound may also be added to the other three additives. The same ratios and amounts disclosed above for the hydroxybenzophenone UV absorber may be used for the benzotriazole UV absorber.
- benzotriazole UV absorbers 2-(2-hydroxy-5-methylphenyl)- benzotriazole; 2-(2-hydroxy-5-tert-butylphenyl)-benzotriazoIe; 2-(2-hydroxy-3,5-di-tert- butylphenyl)-benzotriazole; 5-chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)- benzotriazole; 5-chloro-2-(2-hydroxy-3,5-di-tert-butyl-5-methylphenyl)-benzotriazole; 2-(2- hydroxy-3-tert-phenyl-5-methyl)-benzotriazole; 2-(2-hydroxy-3,5-di-tert-amyl)-benzotriazole; 2-(2-hydroxy-3-sec-butyl-5-tert-butyl)-benzotriazole; 2-(2-hydroxy-4-octyloxy)-benzotriazole; 2-(2-hydroxy-5-tert
- This invention also includes a method of preparing the compositions above by contacting the UV stabilizing additive composition with the material to be stabilized.
- the material to be stabilized and UV stabilizing additive composition are contacted by preferably blending or compounding the components in a kneading apparatus such as a single or twin screw extruder, Banbury mixer, or hot rollers.
- a kneading apparatus such as a single or twin screw extruder, Banbury mixer, or hot rollers.
- the processing parameters and the use of such kneading apparatuses are well known to those skilled in the art.
- the composition of the present invention may include conventional additives including but are not limited to, antioxidants, metal deactivators, hydroxylamines, nitrones, lactones, co- stabilizers, nucleating agents, clarifying agents, neutralizers, metallic stearates, metal oxides, hydrotalcites, fillers and reinforcing agents, plasticizers, lubricants, emulsifiers, pigments, rheological additives, catalysts, level agents, optical brighteners, flame retardant agents, anti-static agents and blowing agents and combinations thereof.
- conventional additives including but are not limited to, antioxidants, metal deactivators, hydroxylamines, nitrones, lactones, co- stabilizers, nucleating agents, clarifying agents, neutralizers, metallic stearates, metal oxides, hydrotalcites, fillers and reinforcing agents, plasticizers, lubricants, emulsifiers, pigments, rheological additives, catalysts, level agents, optical brighteners, flame
- the UV stabilizing additive composition and the material to be stabilized may be used to make articles, such as an extruded or molded articles, coatings, tapes and films.
- the articles may be formed by extrusion, sheet extrusion, injection molding, blow molding, injection blow molding, rotational or roto-molding, calendering, thermoforming, compression molding, vacuum molding, pressure molding, reaction injection molding, and other similar techniques known in the art.
- coatings may be applied by powder coating, extrusion coating, electrocoating, spraying, dipping, and other similar techniques known in the art.
- Examples 1 to 4 Gloss retention. Retained Elongation and Retained Tensile Strength in a Low Density Polyethylene (LDPE) composition
- the UV additives of Examples 1 to 4 are mixed by using a dry blending technique.
- an antioxidant package containing 0.04% by weight (1 ,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-s-triazine- 2,4,6(1 H,3H,5H)trione), 0.08% of tris(2,4-di-tert-butylphenyl)phosphite (Cytec Industries Inc., W. Paterson, NJ) and 0.05% by weight zinc stearate are also mixed with the UV additives.
- Cyasorb ® UV 3346 is 1,6-hexanediamine, N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-, Polymers with morpholine-2,4,6-trichloro-1 ,3,5-triazine (HALS), Cyasorb ® UV 1164 is 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy) phenol (triazine UV absorber), Cyasorb® UV 531 is 2-hydroxy-4-n-octoxybenzophenone(UV absorber).
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Abstract
A composition of an UV stabilizing composition comprises an ortho-hydroxy tris-aryl-s-triazine compound; a hindered amine compound; and a hydroxybenzophenone compound. The ratio of the hindered amine compound to the triazine compound is about 3:1 to about 25:1; and the ratio of the hindered amine compound to the hydroxybenzophenone compound is about 1:1 to 25:1. The UV stabilizing composition can further comprise a material to be stabilized.
Description
UV STABILIZING ADDITIVE COMPOSITION
FIELD OF THE INVENTION This invention relates to an improved UV stabilizing additive composition. More specifically, this invention relates to an UV stabilizing additive composition comprising an ortho-hydroxy triazine compound, a hindered amine compound and hydroxybenzophenone compound. BACKGROUND OF THE INVENTION Exposure to sunlight and other sources of ultraviolet (UV) radiation is known to cause degradation of a wide variety of materials, especially polymeric materials. For example, polymeric materials such as plastics often discolor, lose gloss and/or become brittle as a result of prolonged exposure to UV light due primarily to a reduction in the molecular weight of the polymer. Accordingly, a large body of art has been developed directed towards materials such as UV light absorbers and stabilizers, which are capable of inhibiting such degradation in polymeric articles. The present inventors have found that a combination of ortho-hydroxy triazine compound, a hindered amine compound and hydroxybenzophenone compound provides synergistic protection of materials against UV light. This combination either provides better protection at typical UV stabilizer loading levels, or typical protection at much lower loading levels resulting in significant cost savings over prior art UV stabilizing additive compositions.
SUMMARY OF THE INVENTION
This invention relates to an UV stabilizing additive composition comprising an ortho- hydroxy triazine compound, a hindered amine compound and a hydroxybenzophenone compound. This additive composition may be used to stabilize materials from UV radiation. This invention also contemplates a method of stabilizing a material by contacting the material with the UV stabilizing additive composition.
DETAILED DESCRIPTION OF THE INVENTION This invention relates to an UV stabilizing additive composition comprising an ortho- hydroxy triazine compound, a hindered amine light stabilizing (HALS) compound and a hydroxybenzophenone compound.
Preferably, the ortho-hydroxy tris-aryl-s-triazine compound has the following formula
where Ari and Ar2 are the same or different and are substituted or unsubstituted aryl groups; and where R20 and R2ι are each independently a hydrogen, C C24 alkyl, Cι-C24 haloalkyl, C6-C24 aryl, C2-C24 alkenyl, C C24ac \, Cι-C24 cycloalkyl, C5-C24 cycloacyl, C7-C24 aralkyl, or C6-C24 aracyl, substituted or unsubstituted biphenylene, substituted or unsubstituted napthalene, OR, NRR', CONRR', OCOR, CN, SR, S02R, and where R and R' are each independently a hydrogen, C1-C24 alkyl, Cι-C24 haloalkyl, C6-C24 aryl, C2-C24 alkenyl, C C2 cycloalkyl, C5-C24 cycloacyl, C7-C24 aralkyl, or C6-C24 aracyl, substituted or unsubstituted biphenylene, or substituted or unsubstituted napthalene. Preferably, in the above formula II, A^ has the formula lla:
where R-n is hydrogen, O, OH, C Ci8 alkyl, -CH2CN, C1-C18 alkoxy, C C18 hydroxyalkoxy, C5-C12 cycloalkoxy, C5-C12 hydrocycloalkoxy, C3-C6 alkenyl, CrC18 alkynyl, C7-C9 phenylalkyl, unsubstituted or substituted on the phenyl with 1 , 2 or 3 C C4 alkyls, or an aliphatic C C8 acyl; R12 is hydrogen, C-]-C8 alkyl, or benzyl; R13, R14, R15, and R16 are each independently a C C18 alkyl, benzyl or phenethyl, or optionally R13 and R14, and/or R-ι5 and R16, taken together with the carbon which they are attached, form a C5-C10 cycloalkyl.
Another embodiment of a hindered amine compound is a compound that has formula IV below:
where R10 is a morpholino, Ci -C8 alkylamine, di(Cι -C8) alkylamine, pyrrolidyl, cyclohexylamine or combinations thereof,
X and Xi, which may be the same or different, and are hydrogen, Ci -C20 alkyl, or a radical of formula III defined above,
Rii to R-I6 are as defined above,
Z is a straight chained or branched CrC20 alkylene or a straight chained or branched C
C20 alkalene chain interrupted by at least oxy, thio, or — N(Rι7) — , where R17 is hydrogen, Cι-C2o alkyl, C5-Cι0 cycloalkylene C6-Cι2 arylene, C8-C14 aralkylene or the radical of formula III; n is an integer greater than 1 ; and Y is a halogen atom, C C8 alkylamine, di(CrC8) alkylamine, pyrrolidyl, morpholino, cyclohexylamine, or X Xi N- N - where X, Xi, and Z are as previously defined. Preferably in the above formula IV, Z is a C2 to C6 alkylene, R10 is a morpholino or cyclohexylamine, X and Xi is the radical of formula III, R-n is hydrogen or methyl, R-ι2 is hydrogen, and R13, R14, R15 and R16 are methyl. Another embodiment of a hindered amine is a 2,2,6,6-tetraalkylpiperazinone. One embodiment of a 2,2,6,6-tetraalkylpiperazinone compound is one that contains at least one group of formula IVa:
where R17, R18 and R2 are each independently hydrogen alkyl, aryl, aralkyl, alkaryl, alkoxy, aryloxy having from 1 to 18 carbon atoms and R19 is hydrogen, a C C2 alkyl, or substituted or unsubstituted C6-C24 aryl. Preferably, R17, R18 and R24 are each hydrogen and Rig is a C C8 alkyl. Examples of suitable hindered hydroxybenzophenone compounds include: 2,4-dihydroxybenzophenone; 2-hydroxy-4-methoxybenzophenone; 2-hydroxy-4- octyloxybenzophenone; 2-hydroxy-4-decyloxybenzophenone; 2-hydroxy-4- dodecyloxybenzophenone; 2-hydroxy-4-benzyloxybenzophenone; 2,2'-dihydroxy-4,4'- dimethoxybenzophenone; 2,2',4,4'-tetrahydroxybenzophenone; 2,4-dihydroxy-4'-tert-butyl- benzophenone; 1 ,6-bis-(3-hydroxy-4-benzoylphenoxy)hexane; methylenebis-(2-benzoyl-5- methoxyphenol). In one embodiment of the present invention, the UV stabilizing additive composition of the present invention may be employed to stabilize materials which are subject to degradation by ultraviolet radiation by contacting the UV stabilizing additive composition with a composition comprising polymeric or other materials, either chemically or physically. Non-limiting examples of materials that may be so stabilized are polyolefins, polyesters, polyethers, polyketones, polyamides, natural and synthetic rubbers, polyurethanes, polystyrenes, high-impact polystyrenes, polyacrylates, polymethacrylates, polyacetals, polyacrylonitriles, polybutadienes, polystyrenes, acrylonitrile-butadiene-styrene, styrene acrylonitrile, acrylate styrene acrylonitrile, cellulosic acetate butyrate, cellulosic polymers, polyimides, polyamideimides, polyetherimides, polyphenylsulfides, polyphenyloxide, polysulfones, polyethersulfones, polyvinylchlorides, polycarbonates, polyketones, aliphatic polyketones, thermoplastic olefins, aminoresin cross-linked polyacrylates and polyesters, 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, fibers, waxes, inks, and blends thereof. Preferably, the materials to be stabilized are thermoplastic olefins, acrylonitrile- butadiene-styrene, polyesters, polyvinylchloride, polyamides, polyurethanes, or homo- and copolymers of propylene, isobutylene, butene, methylpentene, hexene, heptene, octene, isoprene, butadiene, hexadiene, dicyclopentadiene, ethylidene cyclopentene and norbomene. More preferably, the materials are polypropylene and thermoplastic olefins. The amount of the triazine compound used in the material to be stabilized using the combination of additives of the present invention is typically lower than normal usage. The lower limit of the amount of triazine may be as low as about 10 ppm, or about 20 ppm, or about 50 ppm or about 75 ppm or about 100 ppm or about 200 ppm, based on the amount of material to be stabilized. There is no upper limit to the amount of triazine, but it would be about 5000 ppm or about 4000 ppm or about 3000 ppm or about 2000 ppm or about 1000 ppm or about 500 ppm, based on the material to be stabilized. The amount of the hydroxybenzophenone compound used in the material to be stabilized using the combination of additives of the present invention is also typically lower than normal usage. The lower limit of the amount of hydroxybenzophenone may be as low as about 10 ppm, or about 20 ppm, or about 50 ppm or about 75 ppm or about 100 ppm or about 200 ppm, or about 500 ppm, based on the amount of material to be stabilized. There is no upper limit to the amount of hydroxybenzophenone, but it would be about 5000 ppm or about 4000 ppm or about 3000 ppm or about 2000 ppm or about 1000 ppm or about 500 ppm, based on the material to be stabilized. The amount of the hindered amine compound used in the material to be stabilized using the combination of additives of the present invention is more or less than its typically used amount. The lower limit of the amount of hindered amine compound may be about 250 ppm, or about 500 ppm, or about 1000 ppm or about 2000 ppm, based on the amount of material to be stabilized. There is no upper limit to the amount of hindered amine compound, but it would be about 30000 ppm, or about 20000 ppm or about 15000 ppm or about 12500 ppm or about 10000 ppm or about 7500 ppm, or about 5000 ppm, based on the material to be stabilized.
The amount of hindered amine compound with respect to the other UV absorbers is typically greater. The ratio of hindered amine compound to the triazine UV absorber may be as high as about 50:1 , or about 25:1, or about 20:1 or about 10:1 , or about 7:1 or about 3:1. The ratio of hindered amine compound to the hydroxybenzophenone UV absorber may be about 25:1 , or about 20:1 or about 10:1 , or about 7:1 or about 3:1 or about 2:1 or about 1.5:1 or about 1 :1. The ratio of hydroxybenzophenone compound to the triazine UV absorber may be about 10: 1 , or about 5: 1 , or about 3: 1 or about 2: 1 , or about 1 : 1 or about 1:2. It should be noted that the amounts and ratios disclosed for the above additives are each independent of each other. This invention contemplates that a benzotriazole UV absorber may be substituted for the hydroxybenzophenone UV absorber. The benzotriazole compound may also be added to the other three additives. The same ratios and amounts disclosed above for the hydroxybenzophenone UV absorber may be used for the benzotriazole UV absorber. The following are examples of benzotriazole UV absorbers: 2-(2-hydroxy-5-methylphenyl)- benzotriazole; 2-(2-hydroxy-5-tert-butylphenyl)-benzotriazoIe; 2-(2-hydroxy-3,5-di-tert- butylphenyl)-benzotriazole; 5-chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)- benzotriazole; 5-chloro-2-(2-hydroxy-3,5-di-tert-butyl-5-methylphenyl)-benzotriazole; 2-(2- hydroxy-3-tert-phenyl-5-methyl)-benzotriazole; 2-(2-hydroxy-3,5-di-tert-amyl)-benzotriazole; 2-(2-hydroxy-3-sec-butyl-5-tert-butyl)-benzotriazole; 2-(2-hydroxy-4-octyloxy)-benzotriazole; 2-(2-hydroxy-5-tert-octyl)-benzotriazole; 2-[2-hydroxy-3,5-di(σ,σ-dimethylbenzyl)phenyl]- benzotriazole; 2-(2-hydroxy-3-dodecyl-5-methylphenyl)benzotriazoIe; 2-[2-hydroxy-3-(α,α'- dimethylbenzyl)-5-(1 ,1 ,3,3-tetramethylbutyl)phenyl]benzotriazole; 2,2'-methylenebis[4- (1,1 ,3,3-tetramethylbutyl)-6-benzotriazol-2-ylphenol]; 2,[2-hydroxy-3-(3,4,5,6- tetrahydrophthalimidomethyl)-5-methylphenyl]benzotriazole; 2-[3-terf-butyl-5-(2-(2- ethylhexyloxycarbonylethyl))-2-hydroxyphenyl]benzotriazole; a mixture of transesterification products of 2-[(3-terf-butyl-5-(2-methoxycarbonylethyl)-2- hydroxyphenyl)benzotriazole with polyethylene glycol of about MW 300; 5-chloro-2-[2-hydroxy-3-tert-butyl-5-(2- octyloxycarbonyl)ethylphenyl]benzotriazole. This invention also includes a method of preparing the compositions above by contacting the UV stabilizing additive composition with the material to be stabilized. The material to be stabilized and UV stabilizing additive composition are contacted by preferably blending or compounding the components in a kneading apparatus such as a single or twin screw extruder, Banbury mixer, or hot rollers. The processing parameters and the use of such kneading apparatuses are well known to those skilled in the art.
As would be apparent to those skilled in the art of making plastic materials, in addition to the material to be stabilized and UV stabilizing additive composition, the composition of the present invention may include conventional additives including but are not limited to, antioxidants, metal deactivators, hydroxylamines, nitrones, lactones, co- stabilizers, nucleating agents, clarifying agents, neutralizers, metallic stearates, metal oxides, hydrotalcites, fillers and reinforcing agents, plasticizers, lubricants, emulsifiers, pigments, rheological additives, catalysts, level agents, optical brighteners, flame retardant agents, anti-static agents and blowing agents and combinations thereof. The UV stabilizing additive composition and the material to be stabilized may be used to make articles, such as an extruded or molded articles, coatings, tapes and films. The articles may be formed by extrusion, sheet extrusion, injection molding, blow molding, injection blow molding, rotational or roto-molding, calendering, thermoforming, compression molding, vacuum molding, pressure molding, reaction injection molding, and other similar techniques known in the art. In addition, coatings may be applied by powder coating, extrusion coating, electrocoating, spraying, dipping, and other similar techniques known in the art.
EXAMPLES The following examples are provided to illustrate the present invention. The examples are not intended to limit the scope of the present invention and they should not be so interpreted.
Examples 1 to 4. Gloss retention. Retained Elongation and Retained Tensile Strength in a Low Density Polyethylene (LDPE) composition The UV additives of Examples 1 to 4 are mixed by using a dry blending technique. In addition to the additives, an antioxidant package containing 0.04% by weight (1 ,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-s-triazine- 2,4,6(1 H,3H,5H)trione), 0.08% of tris(2,4-di-tert-butylphenyl)phosphite (Cytec Industries Inc., W. Paterson, NJ) and 0.05% by weight zinc stearate are also mixed with the UV additives. These additives are compounded with low density polyethylene from Equistar, Houston TX (Microthene, Ml = 3.6, density = 0.9395 g/mL) and extruded using a Davis Standard Killion with conventional single-screw extrusion parameters. After extrusion, standard 2 x 2.5 x 0.125 inch plaques are injection molded using an Arburg injection molder. The performance criteria of Gloss retention, Retained Elongation and Retained Tensile Strength are measured at set exposure intervals (500 for gloss and 2500 hours
for retained elongation and tensile strength) using accelerated exposure in a xenon weather-ometer under ASTM-G-26 with water spray testing conditions. Prior to gloss and color measurements, the samples are washed with Dl water and wiped. Gloss retention measurements are conducted on a Gardner instrument under ASTM Test Procedure D523 with a 60° angle. For breaking strength, 5 tensile bars per each data point are tested on an Instron Engineering Company Tensile Tester (Series IX Automated Test System 7.51.00). The average tensile breaking strength of the three test samples are measured and normalized to samples that are not UV exposed to give a % breaking strength. The cross-head speed of the tensile tester is 1 inch (0.254 cm.) per minute.
The results are shown in Tables 1 to 3 below. Table 1. Percent Gloss Retention of Examples 1 to 4
Table 2. Retained Tensile Stren th of Exam les 1 to 4
The results demonstrate that additive compositions containing half the amount of a triazine UV absorber with a benzophenone perform better than compositions containing the triazine UV alone at double loading.
Claims
1. A composition comprising an UV stabilizing composition comprising: (i) an ortho-hydroxy tris-aryl-s-triazine compound; (ii) a hindered amine compound; and (Hi) a hydroxybenzophenone compound.
2. A composition comprising an UV stabilizing composition comprising: (i) an ortho-hydroxy tris-aryl-s-triazine compound; (ii) a hindered amine compound; and (iii) a hydroxybenzophenone compound where the ratio of the hindered amine compound to the triazine compound is about 3:1 to about 25:1 ; and the ratio of the hindered amine compound to the hydroxybenzophenone compound is about 1:1 to 25:1
The composition of claim 2 further comprising a material to be stabilized.
4. The composition of claim 3 wherein the amount of the triazine compound is about 20 ppm to about 2000 ppm, the amount of the hydroxybenzophenone is about 20 ppm to about 5000 ppm and the amount of the hindered amine is about 250 ppm to about 20000 ppm, all based on the weight of the material to be stabilized.
5. The composition of claim 3, wherein said 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, acrylonitrile-butadiene-styrene, styrene acrylonitrile, acrylate styrene acrylonitrile, cellulosic acetate butyrate, cellulosic polymers, polyimides, polyamideimides, polyetherimides, polyphenylsulfides, polyphenyloxide, polysulfones, polyethersulfones, polyvinylchlorides, polycarbonates, polyketones, aliphatic polyketones, thermoplastic olefins, aminoresin cross-linked polyacrylates and polyesters, 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, heterocyciic 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, fibers, waxes, inks, and blends thereof.
6. The composition of claim 2, wherein said triazine is selected from the group consisting of: 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine; 2-(2-hydroxy-4-n- octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine; 2-(2-hydroxy-4-(mixed iso- octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine; 2-(2,4-dihydroxyphenyl)-4,6- bis(2,4-dimethylphenyl)-1,3,5-triazine; 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4- dimethylphenyl)-1,3,5-triazine; 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)- 1 ,3,5-triazine; 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine; 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine; 2-[2-hydroxy-4- (2-hydroxy-3-butyloxypropyloxy)phenyl]-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine; 2-[2- hydroxy-4-(2-hydroxy-3-octyloxypropyloxy)-phenyl]-4,6-bis(2,4-dimethylphenyl)-1 ,3,5- triazine; 2-[4-dodecyloxy/tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4- dimethylphenyl)-1 ,3,5-triazine; 2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6- bis(2,4-dimethylphenyl)-1 ,3,5-triazine; 2-(2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyl-1 ,3,5- triazine; 2-(2-hydroxy-4~methoxyphenyl)-4,6-diphenyl-1 ,3,5-triazine; 2,4,6-tris[2-hydroxy-4- (3-butoxy-2-hydroxypropoxy)phenyl]-1 ,3,5-triazine; 2-(2-hydroxyphenyl)-4-(4- methoxyphenyl)-6-phenyl-1,3,5-triazine and mixtures thereof.
7. The composition of claim 2, wherein said hindered amine compound is selected from the group consisting of: 1 H-Pyrrole-2,5-dione, 1-octadecyl-, polymer with (1- methylethenyl)benzene and 1 -(2,2,6,6-tetramethyl-4-piperidinyl)-1 H-pyrrole-2,5-dione; piperazinone, 1,1',1"-[1 ,3,5-triazine-2,4,6-triyltris[(cyclohexylimino)-2,1- ethanediyl]]tris[3,3,5,5-tetramethyl-]; piperazinone, 1 ,1',1"-[1,3,5-triazine-2,4,6- triyltris[(cyclohexylimino)-2,1-ethanediyl]]tris[3,3,4,5,5-pentamethyl-]; the reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane and epichlorohydrin; the condensate of N,N'-bis(2,2,6,6-tetramethylpiperidin-4- yl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1 ,3,5-triazine; the condensate of 1 ,2-bis(3-aminopropylamino)ethane, 2,4,6-trichloro-1 ,3,5-triazine and 4- butylamino-2,2,6,6-tetramethylpiperidine; the condensate of N,N'-bis(2, 2,6,6- tetramethylpiperidin-4-yl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1 ,3,5- triazine; the condensate of 2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidyl)- 1 ,3,5-triazine and 1,2-bis(3-aminopropylamino)ethane; the condensate of 2-chloro-4,6- bis(4-n-butylamino-1 ,2,2,6,6-pentamethylpiperidyl)-1 ,3,5-triazine and 1 ,2-bis-(3- aminopropylamino)ethane; 2-[(2-hydroxyethyl)amino]-4,6-bis[N-(1-cyclohexyloxy-2,2,6,6- tetramethylpiperidin-4-yl)butylamino-1 ,3,5-triazine; propanedioic acid, [(4-methoxyphenyl)- methylene]-bis-(1 ,2,2,6,6-pentamethyl-4-piperidinyl) ester; tetrakis(2,2,6,6- tetramethylpiperidin-4-yl)-1 ,2,3,4-butanetetracarboxylate; benzenepropanoic acid, 3,5- bis(1 ,1-dimethylethyl)-4-hydroxy-, 1-[2-[3-[3,5-bis(1 ,1-dimethylethyl)-4-hydroxyphenyl]-1- oxopropoxy]ethyl]-2,2,6,6-tetramethyl-4-piperidinyl ester; N-(1-octyloxy-2,2,6,6- tetramethylpiperidin-4-yl)-N'-dodecyloxalamide; tris(2,2,6,6-tetramethylpiperidin-4-yl) nitrilotriacetate; 1 ,5-dioxaspiro{5,5}undecane-3,3-dicarboxylic acid, bis(1 ,2,2,6,6- pentamethyl-4-piperidinyl); 1 ,5-dioxaspiro{5,5}undecane-3,3-dicarboxylic acid, bis(2,2,6,6- tetramethyl-4-piperidinyl); the condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4- hydroxypiperidine and succinic acid; the condensate of N,N'-bis(2,2,6,6- tetramethylpiperidin-4-yl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1 ,3,5- triazine; 1 ,2,3,4-butanetetracarboxylic acid, 1 ,2,2,6,6-pentamethyl-4-piperidinyl tridecyl ester; tetrakis(2,2,6,6-tetramethylpiperidin-4-yl)-1 ,2,3,4-butanetetracarboxylate; 1 ,2,3,4- butanetetracarboxylic acid, 2,2,6,6-tetramethyl-4-piperidinyl tridecyl ester; tetrakis(1 ,2,2,6,6- pentamethylpiperidin-4-yl)-1 ,2,3,4-butanetetracarboxylate; mixture of 2,2, ,4-tetramethyl- 21 -oxo-7-oxa-3.20-diazaspiro(5.1.11.2)-heneicosane-20-propanoic acid-dodecylester; 2,2,4,4-tetramethyl-21-oxo-7-oxa-3.20-diazaspiro(5.1.11.2)-heneicosane-20-propanoic acid- tetradecylester; 1H,4H,5H,8H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8-dione, hexahydro-2,6-bis(2,2,6,6-tetramethyl-4-piperidinyl)-; polymethyl[propyl-3-oxy(2',2,,6,,6'- tetramethyl-4,4'-piperidinyl)]siloxane; polymethyl[propyl-3-oxy(1',2',2',6,,6'-pentamethyl-4,4I- piperidinyl)]siloxane; copolymer of methylmethacrylate with ethyl acrylate and 2,2,6,6- tetramethylpiperidin-4-yl acrylate; copolymer of mixed C2o to C24 alpha-olef ins and (2,2,6,6- tetramethylpiperidin-4-yl)succinimide; 1,2,3,4-butanetetracarboxylic acid, polymer with β,β,β',β'-tetramethyl-2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol, 1,2,2,6,6- pentamethyl-4-piperidinyl ester; 1 ,2,3,4-butanetetracarboxylic acid, polymer with β,β,β',β'- tetramethyl-2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol, 2,2,6,6-tetramethyI-4- piperidinyl ester copolymer; 1 ,3-benzenedicarboxamide, N,N'-bis(2,2,6,6-tetramethyl-4- piperidinyl; 1,r-(1,10-dioxo-1 ,10-decanediyl)-bis(hexahydro-2,2,4,4,6- pentamethylpyrimidine; ethane diamide, N-(1-acetyl-2,2,6,6-tetramethylpiperidinyl)-N'- dodecyl; formamide, N,N'-1,6-hexanediylbis[N-(2,2,6,6-tetramethyl-4-piperidinyl); D-glucitol, 1 ,3:2,4-bis-O-(2,2,6,6-tetramethyl-4-piperidinylidene)-; 2,2,4,4-tetramethyl-7-oxa-3,20-diaza- 21-oxo-dispiro[5.1.11.2]heneicosane; propanamide, 2-methyl-N-(2,2,6,6-tetramethyl-4- piperidinyl)-2-[(2,2,6,6-tetramethyl-4-piperidinyl)amino]~; 7-oxa-3,20- diazadispiro[5.1.11.2]heneicosane-20-propanoic acid, 2,2,4,4-tetramethyl-21-oxo-, dodecyl ester; N-(2,2,6,6-tetramethylpiperidin-4-yl)-β-aminopropionic acid dodecyl ester; N-(2,2,6,6- tetramethylpiperidin-4-yl)-N'-aminooxalamide; propanamide, N-(2,2,6,6-tetramethyl-4- piperidinyl)-3-[(2,2,6,6-tetramethyl-4-piperidinyl)amino]-; mixture of 4-hexadecyIoxy- and 4- stearyloxy-2,2,6,6-tetramethylpiperidine; 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4- yl)pyrrolidine-2,5-dione; 3-dodecyl-1-(1-ethanoyl-2,2,6,6-pentamethylpiperidin-4- yl)pyrrolidine-2,5-dione; bis(2,2,6,6-tetramethylpiperidin-4-yl)succinate; bis(1 ,2,2,6,6- pentamethylpiperidin-4-yl) n-butyl 3,5-di-tert-butyl-4-hydroxybenzylmalonate; tris(2,2,6,6- tetramethylpiperidin-4-yl) nitrilotriacetate; 1 ,1 '-(1 ,2-ethanediyl)bis(3,3,5,5- tetramethylpiperazinone); 4-benzoyl-2,2,6,6-tetramethylpiperidine; 4-stearyloxy-2, 2,6,6- tetramethylpiperidine; bis(1,2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert- butylbenzyl)malonate; 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decan-2,4-dione; bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)sebacate; bis(1-octyloxy-2,2,6,6- tetramethylpiperidyl)succinate; 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8- triazaspiro[4.5]decane-2,4-dione; 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidin- 2,5-dione; 3-dodecyl-1-(1-ethanoyl-2,2,6,6-tetramethylpiperidin-4-yI)pyrrolidin-2,5-dione; 3- dodecyl-1-(1 ,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione; a mixture of 4- hexadecyloxy- and 4-stearyloxy-2,2,6,6-tetramethylpiperidine; 2-undecyl-7, 7,9,9- tetramethyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane; 1 ,5-dioxaspiro{5,5}undecane-3,3- dicarboxylic acid, bis(2,2,6,6-tetramethyl-4-piperidinyl) and 1 ,5-dioxaspiro{5,5}undecane- 3,3-dicarboxylic acid, bis(1 ,2,2,6,6-pentamethyl-4-piperidinyl) and mixtures thereof.
8. The composition of claim 2 wherein said hydroxybenzophenone is selected from the group consisting of 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2- hydroxy-4-octyloxybenzophenone, 2-hydroxy-4-decyloxybenzophenone, 2-hydroxy-4- dodecyloxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone, 2,2'-dihydroxy-4,4'- dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2,4-dihydroxy-4'-tert-butyl- benzophenone; 1 ,6-bis-(3-hydroxy-4-benzoylphenoxy)hexane; methylenebis-(2-benzoyl-5- methoxyphenol) and mixtures thereof.
9. The composition of claim 2, further comprising a benzotriazole compound.
10. A composition comprising an UV stabilizing composition comprising: (i) an ortho-hydroxy tris-aryl-s-triazine compound; (ii) a hindered amine compound; and (iii) a benzotriazole compound wherein the ratio of the hindered amine compound to the triazine compound is about 3:1 to about 25:1 ; and the ratio of the hindered amine compound to the benzotriazole compound is about 2:1 to 10:1.
11. The composition of claim 10 further comprising a material to be stabilized.
12. The composition of claim 11 wherein the amount of the triazine compound is about 20 ppm to about 2000 ppm, the amount of the benzotriazole is about 20 ppm to about 5000 ppm and the amount of the hindered amine is about 250 ppm to about 20000 ppm, all based on the weight of the material to be stabilized.
13. The composition of claim 10, wherein the benzotriazole compound is selected from the group consisting of: 2-(2-hydroxy-5-methylphenyl)-benzotriazole, 2-(2-hydroxy-5-tert- butylphenyl)-benzotriazole, 2-(2-hydroxy-3,5-di-tert-butylphenyl)-benzotriazole, 5-chloro-2- (2-hydroxy-3-tert-butyl-5-methylphenyl)-benzotriazole, 5-c loro-2-(2-hydroxy-3,5-di-tert- butyl-5-methylphenyl)-benzotriazole, 2-(2-hydroxy-3-tert-phenyl-5-methyl)-benzotriazole, 2- (2-hydroxy-3,5-di-tert-amyl)-benzotriazole, 2-(2-hydroxy-3-sec-butyl-5-tert-butyl)- benzotriazole, 2-(2-hydroxy-4-octyloxy)-benzotriazole, 2-(2-hydroxy-5-tert-octyl)- benzotriazole, 2-[2-hydroxy-3,5-di(σ,σ-dimethylbenzyl)phenyl]-benzotriazole; 2-(2-hydroxy- 3-dodecyl-5-methylphenyl)benzotriazole; 2-[2-hydroxy-3-(α,α'-dimethylbenzyl)-5-(1 ,1 ,3,3- tetramethylbutyl)phenyl]benzotriazole; 2,2'-methylenebis[4-(1 ,1 ,3,3-tetramethylbutyl)-6- benzotriazol-2-ylphenol]; 2,[2-hydroxy-3-(3,4,5,6-tetrahydrophthalimidomethyl)-5- methylphenyljbenzotriazole; 2-[3-fe/τ-butyl-5-(2-(2-ethylhexyloxycarbonylethyl))-2- hydroxyphenyljbenzotriazole; a mixture of transesterification products of 2-[(3-te/τ-butyl-5- (2-methoxycarbonylethyl)-2-hydroxyphenyl)benzotriazole with polyethylene glycol of about MW 300; 5-chloro-2-[2-hydroxy-3-tert-butyl-5-(2-octyloxycarbonyl)ethylphenyl]benzotriazole and mixtures thereof.
14. A composition according to claim 2, where the ratio of the hindered amine compound to the triazine compound is about 3:1 to about 25:1 ; and the ratio of the hindered amine compound to the hydroxybenzophenone compound is about 2:1 to 10:1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006538454A JP2007510781A (en) | 2003-11-04 | 2004-11-03 | Additive composition for UV stabilization |
| EP04800664A EP1680465A1 (en) | 2003-11-04 | 2004-11-03 | Uv stabilizing additive composition |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| US51730203P | 2003-11-04 | 2003-11-04 | |
| US60/517,302 | 2003-11-04 |
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| WO2005047384A1 true WO2005047384A1 (en) | 2005-05-26 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2004/036602 WO2005047384A1 (en) | 2003-11-04 | 2004-11-03 | Uv stabilizing additive composition |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1680465A1 (en) |
| JP (1) | JP2007510781A (en) |
| KR (1) | KR20060113934A (en) |
| CN (1) | CN1875061A (en) |
| WO (1) | WO2005047384A1 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009132924A1 (en) * | 2008-04-30 | 2009-11-05 | Evonik Degussa Gmbh | Polymer composition comprising phenolic resin |
| US7763184B2 (en) | 2007-01-03 | 2010-07-27 | Double Bond Chem. Ind. Co., Ltd. | Light stabilizing liquid matter containing 2- (2-hydroxy-3-α-cumyl-5-tert-octylphenyl) -2h-benzotriazole |
| US7999019B2 (en) * | 2007-09-14 | 2011-08-16 | Sri Sports Limited | Golf ball |
| EP2647664A1 (en) * | 2012-04-04 | 2013-10-09 | Cytec Technology Corp. | Method for stabilizing polyolefin films against UV degradation |
| US10125251B2 (en) | 2014-06-25 | 2018-11-13 | 3M Innovative Properties Company | Fluoropolymer composition including at least one oligomer |
| US10519350B2 (en) | 2015-06-25 | 2019-12-31 | 3M Innovative Properties Company | Copolymer including ultraviolet light-absorbing group and compositions including the same |
| US10577467B2 (en) | 2012-12-20 | 2020-03-03 | 3M Innovative Properties Company | Fluoropolymer composition including an oligomer having an ultraviolet absorbing group |
| WO2021160524A1 (en) * | 2020-02-10 | 2021-08-19 | Basf Se | Light stabilizer mixture |
| WO2023001717A1 (en) * | 2021-07-17 | 2023-01-26 | Basf Se | An additive mixture for stabilization of organic material |
| WO2023041690A1 (en) * | 2021-09-16 | 2023-03-23 | Basf Se | Stabilizer formulation |
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| JP5693274B2 (en) * | 2011-02-07 | 2015-04-01 | 積水フィルム株式会社 | Agricultural film |
| CN103255501B (en) * | 2013-05-31 | 2016-12-28 | 中国科学院长春应用化学研究所 | The preparation method of polyimide fiber |
| CN105218857B (en) * | 2014-09-25 | 2016-08-24 | 黄秀茹 | A kind of additive for polymer |
| EP3591001A1 (en) * | 2014-11-20 | 2020-01-08 | Cytec Industries Inc. | Stabilizer compositions and methods for using same for protecting organic materials from uv light and thermal degradation |
| CN105486558B (en) * | 2015-12-24 | 2018-05-29 | 上海微谱化工技术服务有限公司 | The separation of benzotriazole light stabilizer and detection method in polyphenyl ether engineering plastic |
| CN109651275B (en) * | 2017-10-12 | 2022-12-06 | 江苏裕事达新材料科技有限责任公司 | Triazine compound, composition and preparation method thereof |
| CN109135395A (en) * | 2018-09-03 | 2019-01-04 | 烟台新秀化学科技股份有限公司 | A kind of preparation method of water dispersible light stabilizer |
| JPWO2022065230A1 (en) * | 2020-09-28 | 2022-03-31 | ||
| JP2023013321A (en) * | 2021-07-15 | 2023-01-26 | 東洋インキＳｃホールディングス株式会社 | Compositions, moldings and coatings |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6051164A (en) * | 1998-04-30 | 2000-04-18 | Cytec Technology Corp. | Methods and compositions for protecting polymers from UV light |
| WO2003057772A2 (en) * | 2001-12-27 | 2003-07-17 | Cytec Technology Corp. | Uv stabilized thermoplastic olefins |
-
2004
- 2004-11-03 CN CNA2004800326886A patent/CN1875061A/en active Pending
- 2004-11-03 WO PCT/US2004/036602 patent/WO2005047384A1/en not_active Application Discontinuation
- 2004-11-03 EP EP04800664A patent/EP1680465A1/en not_active Withdrawn
- 2004-11-03 JP JP2006538454A patent/JP2007510781A/en active Pending
- 2004-11-03 KR KR1020067010795A patent/KR20060113934A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6051164A (en) * | 1998-04-30 | 2000-04-18 | Cytec Technology Corp. | Methods and compositions for protecting polymers from UV light |
| WO2003057772A2 (en) * | 2001-12-27 | 2003-07-17 | Cytec Technology Corp. | Uv stabilized thermoplastic olefins |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7763184B2 (en) | 2007-01-03 | 2010-07-27 | Double Bond Chem. Ind. Co., Ltd. | Light stabilizing liquid matter containing 2- (2-hydroxy-3-α-cumyl-5-tert-octylphenyl) -2h-benzotriazole |
| US7999019B2 (en) * | 2007-09-14 | 2011-08-16 | Sri Sports Limited | Golf ball |
| US8450399B2 (en) | 2008-04-30 | 2013-05-28 | Evonik Degussa Gmbh | Polymer composition comprising phenolic resin |
| WO2009132924A1 (en) * | 2008-04-30 | 2009-11-05 | Evonik Degussa Gmbh | Polymer composition comprising phenolic resin |
| EP2647664A1 (en) * | 2012-04-04 | 2013-10-09 | Cytec Technology Corp. | Method for stabilizing polyolefin films against UV degradation |
| WO2013152100A1 (en) | 2012-04-04 | 2013-10-10 | Cytec Technology Corp. | Stabilized polyolefins having increased agrochemical and uv resistance and methods of use |
| US10577467B2 (en) | 2012-12-20 | 2020-03-03 | 3M Innovative Properties Company | Fluoropolymer composition including an oligomer having an ultraviolet absorbing group |
| US10125251B2 (en) | 2014-06-25 | 2018-11-13 | 3M Innovative Properties Company | Fluoropolymer composition including at least one oligomer |
| US10519350B2 (en) | 2015-06-25 | 2019-12-31 | 3M Innovative Properties Company | Copolymer including ultraviolet light-absorbing group and compositions including the same |
| WO2021160524A1 (en) * | 2020-02-10 | 2021-08-19 | Basf Se | Light stabilizer mixture |
| MA57229B2 (en) * | 2020-02-10 | 2024-09-30 | Basf Se | PHOTOSTABILIZING MIXTURE |
| WO2023001717A1 (en) * | 2021-07-17 | 2023-01-26 | Basf Se | An additive mixture for stabilization of organic material |
| WO2023041690A1 (en) * | 2021-09-16 | 2023-03-23 | Basf Se | Stabilizer formulation |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1875061A (en) | 2006-12-06 |
| EP1680465A1 (en) | 2006-07-19 |
| KR20060113934A (en) | 2006-11-03 |
| JP2007510781A (en) | 2007-04-26 |
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