US20040241111A1 - Highly compatible hydroxyphenyltriazine uv-absorbers - Google Patents
Highly compatible hydroxyphenyltriazine uv-absorbers Download PDFInfo
- Publication number
- US20040241111A1 US20040241111A1 US10/482,680 US48268004A US2004241111A1 US 20040241111 A1 US20040241111 A1 US 20040241111A1 US 48268004 A US48268004 A US 48268004A US 2004241111 A1 US2004241111 A1 US 2004241111A1
- Authority
- US
- United States
- Prior art keywords
- alkyl
- formula
- hydrogen
- tert
- phenyl
- 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.)
- Abandoned
Links
- 239000006096 absorbing agent Substances 0.000 title claims abstract description 14
- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical compound OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000000463 material Substances 0.000 claims abstract description 13
- 230000005855 radiation Effects 0.000 claims abstract description 12
- 239000002537 cosmetic Substances 0.000 claims abstract description 8
- 235000013361 beverage Nutrition 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 7
- 230000002939 deleterious effect Effects 0.000 claims abstract description 6
- 230000004224 protection Effects 0.000 claims abstract description 5
- -1 C1 -C4alkyl Substances 0.000 claims description 102
- 239000000203 mixture Substances 0.000 claims description 87
- 150000001875 compounds Chemical class 0.000 claims description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 70
- 229920000642 polymer Polymers 0.000 claims description 58
- 150000002431 hydrogen Chemical class 0.000 claims description 40
- 239000000654 additive Substances 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 229920003023 plastic Polymers 0.000 claims description 26
- 239000004033 plastic Substances 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000004952 Polyamide Substances 0.000 claims description 15
- 229920002647 polyamide Polymers 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000004417 polycarbonate Substances 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000003073 divalent carboacyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 229920000620 organic polymer Polymers 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 12
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])C([H])([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
- KHMYONNPZWOTKW-UHFFFAOYSA-N pent-1-enylbenzene Chemical class CCCC=CC1=CC=CC=C1 KHMYONNPZWOTKW-UHFFFAOYSA-N 0.000 description 1
- 125000002460 pentacosyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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
- FDUBTTQMOFEVRB-UHFFFAOYSA-N pentadecane-1,1-diol Chemical compound CCCCCCCCCCCCCCC(O)O FDUBTTQMOFEVRB-UHFFFAOYSA-N 0.000 description 1
- 125000002958 pentadecyl 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])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
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000012994 photoredox catalyst Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001627 poly(4-methyl styrene) Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920003251 poly(α-methylstyrene) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 125000002469 tricosyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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
- ZUDWINGCBFUXNG-UHFFFAOYSA-N tridecane-1,1-diol Chemical compound CCCCCCCCCCCCC(O)O ZUDWINGCBFUXNG-UHFFFAOYSA-N 0.000 description 1
- INNSFNJTGFCSRN-UHFFFAOYSA-N tridecyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 INNSFNJTGFCSRN-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- GRXOWOKLKIZFNP-UHFFFAOYSA-N undecane-1,1-diol Chemical compound CCCCCCCCCCC(O)O GRXOWOKLKIZFNP-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 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
- C08K5/16—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- 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]
Definitions
- the present invention relates to highly compatible hydroxyphenyltriazine UV-absorbers and to organic polymer material containing them, especially for use in protecting plants in greenhouses and for protecting packed foodstuffs, beverages, pharmaceuticals, cosmetics, personal care products, shampoos and the like from the deleterious effects of ultraviolet radiation. It has been found that certain highly compatible tris-aryl-s-triazines are especially effective towards this end when incorporated in the containers or films in which such materials are stored. Compounds of present invention are further effective in cosmetic formulations for the protection of human (or animal) skin or hair against UV radiation.
- Antignus et al. The use of UV absorbing plastic sheets to protect crops against insects and spread of virus diseases , CIPA Congress March 1997, pp.23-33].
- bee activity requiring a certain band of UV radiation, needs to be retained in greenhouses in order to ensure fructification on flowering plants, e.g. tomato, cucumber, pumpkin etc.
- UV ultraviolet
- UV absorbers towards protecting bottle and film contents are well known.
- clear or lightly colored containers More aesthetically pleasing containers may be formed from clear plastics which also allow one to view the contents.
- clear and lightly colored containers and films allow the transmission of significant portions of ultraviolet light, i.e. light in the range of about 280 to about 400 nm.
- more light-weight and hence thinner walled containers Thin-walled containers, by virtue of a shorter path length, will allow more UV light to pass. Due to these trends in packaging there is a need for more efficient UV absorbers for use in this area.
- Tinuvin® 326 is a benzotriazole UV absorber, 5-chloro-2-(2-hydroxy-3-tert-butyl-5-methyl-phenyl)-2H-benzotriazole, available from Ciba Specialty Chemicals Corp.
- UV absorbers show excellent compatibility and persistence in a variety of plastic materials and protect these materials from the harmful effects of UV radiation. The same time, these UV absorbers provide efficient and selective UV shielding in greenhouse films, window sheets and packaging materials. Due to their extremely long alkyl chains they are highly compatible with many polymers, allowing thus to incorporate higher amounts of UVA. They are thermally stable and do not exude from the polymer, which is important when in contact with food or beverages.
- the present invention relates to a hydroxyphenyltriazine of formula (I) or (Ib)
- x is a number from 1 to 50;
- A is a group of the formula (IIIb)
- D is a divalent residue containing 2 to 60 carbon atoms comprising an aliphatic, cycloaliphatic or aromatic hydrocarbon, or said aliphatic residue substituted by OH or interrupted by O or both substituted by OH and interrupted by O; and in case that D bonds to the carbon atom of L, D also comprises methylene or a direct bond;
- L stands for an ester linkage group
- R 1 are independently of each other H, OR 7 or OH, with the proviso that at least one of R 1 or R 13 is OH;
- R 7 are independently of each other hydrogen, C 1 -C 12 alkyl or a radical of formula (III)
- R 8 is hydrogen, C 1 -C 18 alkyl; C 5 -C 12 cycloalkyl; C 2 -C 18 alkenyl; phenyl; C 7 -C 11 phenylalkyl; C 7 -C 11 alkylphenyl; C 1 -C 18 alkyl substituted by phenyl, OH, halogen; C 1 -C 18 alkoxy, C 5 -C 12 cycloalkoxy, C 3 -C 18 alkenyloxy or COOH;
- Y is —CO— or C 1 -C 12 alkylene
- R 9 if Y is —CO—, is C 20 -C 60 alkyl, C 20 -C 60 alkyl substituted by OH and/or interrupted by O, or is
- C 20 -C 60 alkenyl or is a group of formula (IV)
- n is a number from 1 to 20;
- R 9 if Y is alkylene, is C 20 -C 60 alkanoyl
- R 2 , R 3 , R 4 , R 5 and R 6 are independently of each other hydrogen, C 1 -C 38 alkyl which is unsubstituted or substituted by hydroxy or C 1 -C 8 alkoxy; or
- C 1 -C 38 alkyl which is interrupted by an oxygen atom or a N(C 1 -C 18 )alkyl group; phenyl or C 7 -C 12 phenylalkyl which are unsubstituted or substituted by hydroxy or C 1 -C 8 alkyl;
- R 10 is hydrogen, C 1 -C 4 alkyl, Cl, phenyl or a group —OR 7 ;
- R 11 is hydrogen or methyl
- R 13 is hydrogen, methyl, OH or OR 7 ;
- R 14 and R 15 are independently hydrogen, C 1 -C 8 alkyl, Cl or a group OR 7 ;
- R 16 is is hydrogen, C 1 -C 8 alkyl, Cl or phenyl
- R 18 is hydrogen or C 1 -C 8 alkyl.
- R 8 is hydrogen or C 1 -C 8 alkyl
- Y is —CO— or C 1 -C 2 alkylene;
- R 9 if Y is —CO—, is C 20 -C 60 alkyl, C 20 -C 60 alkyl substituted by OH and/or interrupted by O, or is
- m is a number from 2 to 12;
- R 9 if Y is alkylene, is C 20 -C 60 alkanoyl
- R 2 , R 3 , R 4 , R 5 and R 6 are independently of each other hydrogen, C 1 -C 8 alkyl or C 4 -C 12 hydroxyalkyl or C 4 -C 12 alkoxyalkyl;
- R 10 is hydrogen or a group —OR 7 ;
- R 11 and R 18 independently are hydrogen or methyl
- R 13 is hydrogen, OH or methyl.
- R 1 are OH
- R 7 are hydrogen or methyl or a radical of formula (III)
- R 8 is hydrogen or C 1 -C 4 alkyl
- R 10 is hydrogen, methyl or a group —OR 7 ;
- R 11 and R 18 are hydrogen
- R 13 is hydrogen, OH or methyl.
- Terminal groups of the oligomer or polymer of formula (II) usually are
- R 12 is H or C 1 -C 8 alkyl.
- the ester linkage group L is —COO— or —OCO—.
- ester of formula (II) may conform to the formula (IIa)
- x is a number from 1 to 20;
- the number y is at least 1 and ranges from (x+z ⁇ 1) to (x+z+1);
- z is a number from 0 to 20.
- R 12 is hydrogen or C 1 -C 8 alkyl
- R 18 is hydrogen or C 1 -C 8 alkyl
- Y is —CO— or C 1 -C 12 alkylene
- D′ is C 2 -C 38 alkylene or C 4 -C 60 alkylene interrupted by O; and T is the divalent acyl residue of an aliphatic, cycloaliphatic or aromatic dicarboxylic acid of 2 to 12 carbon atoms;
- D′ is the divalent acyl residue of an aliphatic, cycloaliphatic or aromatic dicarboxylic acid of 2 to 12 carbon atoms
- T is C 2 -C 38 alkylene or C 4 -C 60 alkylene interrupted by O;
- each of the divalent structural units identified by the indices x and z bond to the structural unit —O-D′- identified by the index y, and/or to an end group R 12 or OR 12 .
- ester of formula (II) may also conform to the formula (IIb)
- p ranges from 1 to 12, especially from 2 to 8;
- z is 0 or 1; and all other symbols are as defined above.
- formula III conforms to the formula
- R 8 being H or C 1 -C 8 alkyl, especially methyl.
- Compounds of the formula (II) usually are of the type heteropolyester comprising two classes of structural units, one derived from dicarboxylic acids and the other from dioles. If in formula (II) the moiety L-A-L is a residue of a dicarboxylic acid, -D- is the residue of a divalent alcohol; if in formula (II) the moiety L-D-L is a residue of a dicarboxylic acid, -A- is the residue of a divalent alcohol.
- L-D-L as a divalent acyl residue conforms to the formula —OCO-D-COO—
- D′ or T as a divalent acyl residue conform to the formula —CO—T′—CO—
- D or T′ is, for example, a direct bond, C 1 -C 60 alkylene, C 2 -C 10 alkenylene, phenylene, naphthylene, C 5 -C 8 cycloalkylene, C 2 -C 4 alkylene or alkenylene interrupted by O or cyclohexylene or phenylene, C 2 -C 12 alkylene substituted by OH.
- More preferred D or T′ in this meaning are phenylene, cyclohexylene, C 2 -C 10 alkylene, or C 2 -C 10 alkylene substituted by OH.
- D′ or T as a diol residue conform to the formula —O—T′—O—;
- D or T′ in this meaning are, for example, C 2 -C 60 alkylene, C 2 -C 10 alkenylene, C 5 -C 8 cycloalkylene, C 4 -C 60 alkylene or alkenylene interrupted by O, cyclohexylene and/or phenylene. More preferred D or T′ in this meaning are C 2 -C 24 alkylene, or C 4 -C 60 alkylene interrupted by O.
- x is preferably from the range 2-50, more preferably from the range 2-20, especially 4-12.
- each of x and y are preferably from the range 2-16, more preferably from the range 4-12;
- z is preferably ranging from 0-12.
- Oligomeric or polymeric esters of the invention such as those of formula 11 usually have a molecular weight within the range 1000 to 50000 g/mol, more preferably 1500 to 20000 g/mol, most preferably 2000 to 10000 g/mol (number average Mn as determined by gel permeation chromatography GPC).
- R 1 are independently of each other H, OR 7 or OH, with the proviso that at least one of R 1 or R 13 is OH;
- R 7 are independently of each other hydrogen, C 1 -C 12 alkyl or a radical of formula III
- R 8 is hydrogen, C 1 -C 18 alkyl; C 5 -C 12 cycloalkyl; C 2 -C 18 alkenyl; phenyl; C 7 -C 11 ,phenylalkyl; C 7 - C 11 alkylphenyl; C 1 -C 18 alkyl substituted by phenyl, OH, halogen; C 1 -C 18 alkoxy, C 5 -C 12 cycloalkoxy, C 3 -C 18 alkenyloxy or COOH;
- R 9 is C 20 -C 60 alkyl, C 20 -C 60 alkyl which is substituted in ⁇ position with a OH group or C 20 -C 60 alkenyl or a group of formula (IV)
- m is a number from 1 to 20;
- R 2 , R 3 , R 4 , R 5 and R 6 are independently of each other hydrogen, C 1 -C 38 alkyl which is unsubstituted or substituted by hydroxy or C 1 -C 8 alkoxy; or
- C 1 -C 38 alkyl which is interrupted by an oxygen atom or a N(C 1 -C 18 )alkyl group;
- phenyl or C 7 -C 12 phenylalkyl which are unsubstituted or substituted by hydroxy or C 1 -C 18 alkyl;
- n is a number from 1 to 38;
- p is a number from 2 to 20.
- R 10 is hydrogen, C 1 -C 4 alkyl, Cl, phenyl or a group —OR 7 ;
- R 11 is hydrogen or methyl
- R 12 is hydrogen, methyl or ethyl
- R 13 is hydrogen, methyl, OH or a group OR 7 ;
- R 14 and R 15 are independently hydrogen, C 1 -C 8 alkyl, Cl or a group OR 7 ;
- R 16 is is hydrogen, C 1 -C 8 alkyl, Cl or phenyl.
- Alkylphenyl is alkyl-substituted phenyl; C 7 -C 14 alkylphenyl embraces examples such as methylphenyl (tolyl), dimethylphenyl (xylyl), trimethylphenyl (mesityl), ethylphenyl, propylphenyl, butylphenyl, dibutylphenyl, pentylphenyl, hexylphenyl, heptylphenyl and octylphenyl.
- Phenylalkyl is phenyl-substituted alkyl; C 7 -C 11 phenylalkyl embraces examples such as benzyl, ⁇ -methylbenzyl, ⁇ -ethylbenzyl, ⁇ , ⁇ -dimethylbenzyl, phenylethyl, phenylpropyl, phenylbutyl and phenylpentyl.
- Alkyl interrupted by O, NH, N(C 1 -C 12 )alkyl can generally comprise one or more nonadjacent heteroatoms.
- the alkyl radicals are branched or unbranched alkyl such as methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hex
- Examples for the C 20 -C 60 alkyl radicals in the definition of R 9 are icosyl, henicosyl, docosyl, tricosyl, pentacosyl, heptacosyl, nonacosyl, triacontyl, dotriacontyl, tetracontyl, pentacontyl and hexacontyl.
- the alkenyl radicals include allyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl; n-oct-2-enyl, n-dodec-2-enyl, isododecenyl, n-octadec-2-enyl and n-octadec-4-enyl.
- R 8 is C 1 -C 18 alkyl more preferably C 1 -C8alkyl, in particular methyl.
- R 18 is hydrogen or methyl, especially hydrogen.
- R 9 as C 20 -C 60 alkyl substituted by OH preferably carries only one OH group in ⁇ position.
- Preferred is a compound wherein R 9 is C 20 -C 60 alkyl, more preferred C 26 -C 52 alkyl and in particular R 9 is a mixture of alkyl with a range from 20 to 40 carbon atoms the mean value being around 32 carbon atoms.
- the high alkyl groups of R 9 may also have a certain molecular distribution around their main component. Ranges may for example be from 22-26, 28-32 or 34-38 C-atoms. It is however also possible that broader ranges are used such as for example from 20 to 40, from 30 to 50 or from 40 to 60 carbon atoms.
- the educts for preparing a compound of formula (I), (Ia) or (Ib) are commercial products they may vary within certain specifications. This is particularly the case for high molecular weight alcohols from which the R 9 groups are derived, when R 9 is C 20 -C 60 alkyl.
- Rg is a mixture containing up to 10% of alkyl chains below 20 carbon atoms and 90 to 100% of alkyl chains between 20 and 60, particularly between 20 and 40 carbon atoms are also subject of the invention. Percentage is weight percent, based on the total mixture.
- R 9 is a group of formula (IV)
- R 2 is preferably hydrogen or C 1 -C 4 alkyl
- R 3 , R 4 , R 5 and R 6 are preferably hydrogen or C 1 -C 38 alkyl, more preferably C 4 -C 24 alkyl and in particular C 4 -C 12 alkyl.
- n is preferably 2-24, more preferably 4-16 and most preferably 4-12.
- p is preferably 2-12 and more preferably 2-8.
- the compounds of formula I, (Ia), (Ib) and (II) or precursors thereof can be prepared in analogy to one of the methods indicated in EP-A-434 608, one of the publications specified at the outset, or in the publication by H. Brunetti and C. E. Lüthi, Helv. Chim. Acta 55, 1566 (1972), by Friedel-Crafts addition of halotriazines with corresponding phenols; see also U.S. Pat. No. 3,118,887 and EP-A-1 65608.
- This can be followed by a further, conventional reaction to give compounds of the formula I in which R 7 is other than hydrogen; such reactions and methods are described, for example, in EP-A-434 608, page 15, line 11, to page 17, line 1. Further examples of the preparation are given in GB 2337049.
- (Poly)esters of formula (Ia), (II) or (IIa) are advantageously prepared starting from tris-aryl-triazines containing 2 carboxylic acid groups or suitable derivatives thereof such as acid chloride, anhydride or especially ester groups, or, alternatively, 2 reactable, preferably primary, OH groups.
- Such educts or their homologues are described, inter alia, in U.S. Pat. No. 4,826,978, U.S. Pat. No. 5,736,597 (see e.g. columns 11-13), U.S. Pat. No. 5,686,233, U.S. Pat. No. 5,959,008 (see e.g. col. 30, line 35, until col. 31, line 11).
- dicarboxylic educts e.g. aliphatic, cycloaliphatic or aromatic dicarboxylic acids or derivatives thereof, or dialcohols
- the dicarboxylic educts are preferably reacted according to methods known in the art with suitable amounts, e.g. 0.9 - 1.1 mol per mol dicarboxyl or equimolar amounts, of a diol HO-D-OH, with or without additional dicarboxylic compounds present; diol educts are correspondingly reacted with dicarboxylic acids, anhydrides, acid chlorides or preferably esters e.g. of formula R 12 —O-D-O—R 12 .
- Preferred dicarboxylic acid educts include those based on oxalic, malonic, maleic, malic, fumaric, succinic, glutaric, adipinic, pimelic, suberic, azelaic, sebacic, phthalic, isophthalic, terephthalic, cyclohexyl dicarboxylic, glutaconic, itaconic, tartaric acid; preferred diols include glycol, glycerine, various polyethylene glycoles, or ⁇ , ⁇ -dihydroxyalkanes of various chain lengths such as butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol, undecanediol, dodecanediol, tridecanediol, pentadecanediol,
- Reaction can be carried out with or without addition of further components such as solvents (e.g. aliphatic alcohols, ethers, aromatic hydrocarbons or halogenated hydrocarbons such as chlorobenzene, or solvent mixtures) or catalysts, e.g. transesterification catalysts such as mineral or organic (Lewis or Broensted-type) acids or bases.
- solvents e.g. aliphatic alcohols, ethers, aromatic hydrocarbons or halogenated hydrocarbons such as chlorobenzene, or solvent mixtures
- catalysts e.g. transesterification catalysts such as mineral or organic (Lewis or Broensted-type) acids or bases.
- an educt such as the diol or a suitable ester of a dicarboxylic acid may be used in excess and serve simultaneously as a solvent.
- Temperature and pressure are usually not critical, thus, the reaction often is carried out at temperatures in the range ⁇ 5° C. to 200° C., e.g. between
- Present invention also pertains to an oligoester or polyester which is obtained by reacting a tris-aryl-triazine of the formula V
- Y is alkylene, with a diacid or diester R 12 —O-T-O—R 12 , optionally in presence of a diol of the formula HO-T-OH.
- Present invention also pertains to a composition protected against the permeation of ultraviolet radiation comprising
- a further subject of the invention is a plastic container or film which protects against the deleterious effects of ultraviolet radiation which comprise
- the compounds are useful for many kinds of plastic materials from which containers, sheets, films and woven or nonwoven fabrics can be made. Examples are given below.
- Polymers of monoolefins and diolefins for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyvinylcyclohexane, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for instance of cyclopentene or norbornene, polyethylene (which optionally can be crosslinked), for example high density polyethylene (HDPE), high density and high molecular weight polyethylene (HDPE-HMW), high density and ultrahigh molecular weight polyethylene (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE).
- HDPE high density polyethylene
- HDPE-HMW high density and high molecular weight polyethylene
- HDPE-UHMW high density and ultrahigh molecular weight polyethylene
- MDPE medium density polyethylene
- LDPE low density
- Polyolefins i.e. the polymers of monoolefins exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different, and especially by the following, methods:
- These metals usually have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and/or aryls that may be either ⁇ - or ⁇ -coordinated.
- These metal complexes may be in the free form or fixed on substrates, typically on activated magnesium chloride, titanium(III) chloride, alumina or silicon oxide.
- These catalysts may be soluble or insoluble in the polymerisation medium.
- the catalysts can be used by themselves in the polymerisation or further activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, said metals being elements of groups Ia, IIa and/or IIIa of the Periodic Table.
- the activators may be modified conveniently with further ester, ether, amine or silyl ether groups.
- These catalyst systems are usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC).
- Copolymers of monoolefins and diolefins with each other or with other vinyl monomers for example ethylene/propylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene/but-1-ene copolymers, propylene/isobutylene copolymers, ethylene/but-1-ene copolymers, ethylene/hexene copolymers, ethylene/methylpentene copolymers, ethylene/heptene copolymers, ethylene/octene copolymers, ethylene/vinylcyclohexane copolymers, ethylene/cycloolefin copolymers (e.g.
- ethylene/norbornene like COC ethylene/1-olefins copolymers, where the 1-olefin is gene-rated in-situ; propylene/butadiene copolymers, isobutylene/isoprene copolymers, ethylene/vinylcyclohexene copolymers, ethylene/alkyl acrylate copolymers, ethylene/alkyl methacrylate copolymers, ethylene/vinyl acetate copolymers or ethylene/acrylic acid copolymers and their salts (ionomers) as well as terpolymers of ethylene with propylene and a diene such as hexadiene, dicyclopentadiene or ethylidene-norbornene; and mixtures of such copolymers with one another and with polymers mentioned in 1) above, for example polypropylene/ethylene-propylene copolymers, LDPE/ethylene-vinyl acetate cop
- Hydrocarbon resins for example C 5 -C 9
- hydrogenated modifications thereof e.g. tackifiers
- mixtures of polyalkylenes and starch
- Homopolymers and copolymers from 1.)-4.) may have any stereostructure including syndiotactic, isotactic, hemi-isotactic or atactic; where atactic polymers are preferred. Stereoblock polymers are also included.
- Homopolymers and copolymers may have any stereostructure including syndiotactic, isotactic, hemi-isotactic or atactic; where atactic polymers are preferred. Stereoblock polymers are also included.
- Copolymers including aforementioned vinyl aromatic monomers and comonomers selected from ethylene, propylene, dienes, nitriles, acids, maleic anhydrides, maleimides, vinyl acetate and vinyl chloride or acrylic derivatives and mixtures thereof, for example styrene/butadiene, styrene/acrylonitrile, styrene/ethylene (interpolymers), styrene/alkyl methacrylate, styrene/butadiene/alkyl acrylate, styrene/butadiene/alkyl methacrylate, styrene/maleic anhydride, styrene/acrylonitrile/methyl acrylate; mixtures of high impact strength of styrene copolymers and another polymer, for example a polyacrylate, a diene polymer or an ethylene/propylene/diene terpolymer; and block copoly
- 6b Hydrogenated aromatic polymers derived from hydrogenation of polymers mentioned under 6.), especially including polycyclohexylethylene (PCHE) prepared by hydrogenating atactic polystyrene, often referred to as polyvinylcyclohexane (PVCH).
- PCHE polycyclohexylethylene
- PVCH polyvinylcyclohexane
- 6c Hydrogenated aromatic polymers derived from hydrogenation of polymers mentioned under 6a.).
- Homopolymers and copolymers may have any stereostructure including syndiotactic, isotactic, hemi-isotactic or atactic; where atactic polymers are preferred. Stereoblock polymers are also included.
- Halogen-containing polymers such as polychloroprene, chlorinated rubbers, chlorinated and brominated copolymer of isobutylene-isoprene (halobutyl rubber), chlorinated or sulfochlorinated polyethylene, copolymers of ethylene and chlorinated ethylene, epichlorohydrin homo- and copolymers, especially polymers of halogen-containing vinyl compounds, for example polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride, as well as copolymers thereof such as vinyl chloride/vinylidene chloride, vinyl chloride/vinyl acetate or vinylidene chloride/vinyl acetate copolymers.
- halogen-containing polymers such as polychloroprene, chlorinated rubbers, chlorinated and brominated copolymer of isobutylene-isoprene (halobutyl rubber), chlorinated
- Copolymers of the monomers mentioned under 9) with each other or with other unsaturated monomers for example acrylonitrile/ butadiene copolymers, acrylonitrile/alkyl acrylate copolymers, acrylonitrile/alkoxyalkyl acrylate or acrylonitrile/vinyl halide copolymers or acrylonitrile/alkyl methacrylate/butadiene terpolymers.
- Polymers derived from unsaturated alcohols and amines or the acyl derivatives or acetals thereof for example polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, polyallyl phthalate or polyallyl melamine; as well as their copolymers with olefins mentioned in 1) above.
- Polyacetals such as polyoxymethylene and those polyoxymethylenes which contain ethylene oxide as a comonomer; polyacetals modified with thermoplastic polyurethanes, acrylates or MBS.
- Polyamides and copolyamides derived from diamines and dicarboxylic acids and/or from aminocarboxylic acids or the corresponding lactams for example polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamide 11, polyamide 12, aromatic polyamides starting from m-xylene diamine and adipic acid; polyamides prepared from hexamethylenediamine and isophthalic or/and terephthalic acid and with or without an elastomer as modifier, for example poly-2,4,4,-trimethylhexamethylene terephthalamide or poly-m-phenylene isophthalamide; and also block copolymers of the aforementioned polyamides with polyolefins, olefin copolymers, ionomers or chemically bonded or grafted elastomers; or with polyethers, e.g. with polyethylene glycol, polypropylene glycol or polytet
- Polyesters derived from dicarboxylic acids and diols and/or from hydroxycarboxylic acids or the corresponding lactones for example polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylolcyclohexane terephthalate, polyalkylene naphthalate (PAN) and polyhydroxybenzoates, as well as block copolyether esters derived from hydroxyl-terminated polyethers; and also polyesters modified with polycarbonates or MBS.
- Blends of the aforementioned polymers for example PP/EPDM, Polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylates, POM/thermoplastic PUR, PC/thermoplastic PUR, POM/acrylate, POM/MBS, PPO/HIPS, PPO/PA 6.6 and copolymers, PA/HDPE, PA/PP, PA/PPO, PBT/PC/ABS or PBT/PET/PC.
- polyblends for example PP/EPDM, Polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylates, POM/thermoplastic PUR, PC/thermoplastic PUR, POM/acrylate, POM/MBS
- a is a polyolefin, a polyester, a polyvinylalcohol, a polyvinylacetate, a polycarbonate, a polyamide, an acrylic (co)polymer, or acryl-butadiene-styrene terpolymer (ABS); especially a polyolefin, a polyester, a polyvinylalcohol, a polyvinylacetate or a polycarbonate.
- the organic polymer material is a plastic container or film or sheet wherein the plastic material is transparent, for instance clear, or lightly colored.
- More preferred materials for films or plastic containers are a polyolefin, a polyester, a polyvinylalcohol, a polyvinylacetate or a polycarbonate; most preferred are polyethylenetherephthalate (PET) and polyolefins, in particular (PE), polyethylene, (LDPE), low density polyethylene, linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE). More preferred materials for sheets are polycarbonate, a polyamide, a polyacryl, or transparent ABS, especially polycarbonate.
- the present UV absorbers may also be incorporated into optical lenses or glasses, such as acryl glasses, or coatings thereon.
- Preferred materials for optical lenses and glasses, e.g. for sunglasses, are acrylics or polycarbonate, especially polymethyl methacrylate (PMMA).
- PMMA polymethyl methacrylate
- the composition of the invention is a plastic container or film used as a food packaging material.
- the thickness of the film is from 10 ⁇ to 200 ⁇ , more preferably from 20 ⁇ to 80 ⁇ and in particular from 20 ⁇ to 60 ⁇ and of the plastic container from 200 ⁇ to 1000 ⁇ .
- the thickness of the sheet may vary between about 0.5 to 8 mm, e.g. for solid sheets, to about 3 to 100 mm, e.g. for twin or multiple wall sheets.
- the compound of formula (I), (II), (IIa), (Ia) or (Ib) is present in an amount of from 0.005% to 10%, more preferably of from 0.05% to 4%, and most preferably of from 0. 1% to 2.5%, based on the weight of the plastic material.
- the plastic material of the invention may also include other stabilizers or other additives, such as a phenolic antioxidant, a sterically hindered amine and/or a phosphite or phosphonite.
- the plastic container or film may also additionally contain an iron based additive as oxygen absorber.
- Alkylated monophenols for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-di-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-( ⁇ -methylcyclohexyl)-4,6-dimethyl-phenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, nonylphenols which are linear or branched in the side chains, for example, 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6-(1′-methylundec-1′-
- Alkylithiomethylphenols for example 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctyl-thiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonylphenol.
- Hydroquinones and alkylated hydroquinones for example 2,6-di-tert-butyl-4-methoxy-phenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octade-cyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis-(3,5-di-tert-butyl-4-hydroxyphenyl) adipate.
- 2,6-di-tert-butyl-4-methoxy-phenol 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphen
- Tocopherols for example ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol and mixtures thereof (Vitamin E).
- Hydroxylated thiodiphenyl ethers for example 2,2′-thiobis(6-tert-butyl-4-methylphenol), 2,2′-thiobis(4-octylphenol), 4,4′-thiobis(6-tert-butyl-3-methylphenol), 4,4′-thiobis(6-tert-butyl-2-methylphenol), 4,4′-thiobis-(3,6-di-sec-amylphenol), 4,4′-bis(2,6-dimethyl-4-hydroxyphenyl) disulfide.
- 2,2′-thiobis(6-tert-butyl-4-methylphenol 2,2′-thiobis(4-octylphenol), 4,4′-thiobis(6-tert-butyl-3-methylphenol), 4,4′-thiobis(6-tert-butyl-2-methylphenol), 4,4′-thiobis-(3,6-di-sec-amylphenol), 4,4′-bis(2,6-
- Alkylidenebisphenols for example 2,2′-methylenebis(6-tert-butyl-4-methylphenol), 2,2′-methylenebis (6-tert-butyl-4-ethylphenol), 2,2′-methylenebis[4-methyl-6-( ⁇ -methylcyclohexyl)-phenol], 2,2′-methylenebis(4-methyl-6-cyclohexylphenol), 2,2′-methylenebis(6-nonyl-4-methylphenol), 2,2′-methylenebis(4,6-di-tert-butylphenol), 2,2′-ethylidenebis(4,6-di-tert-butylphenol), 2,2′-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2′-methylenebis[6-( ⁇ -methylbenzyl)-4-nonylphenol], 2,2′-methylenebis[6-( ⁇ , ⁇ -dimethylbenzyl)-4-isobutylphenol
- 1.8. Hydroxybenzylated malonates for example dioctadecyl-2,2-bis-(3,5-di-tert-butyl-2-hydroxybenzyl)-malonate, di-octadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)-malonate, didodecylmercaptoethyl-2,2-bis-(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, bis[4-(1,1,3,3-tetramethylbutyl) phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate.
- Hydroxybenzylated malonates for example dioctadecyl-2,2-bis-(3,5-di-tert-butyl-2-hydroxybenzyl)-malonate, di-octadecyl-2-(3-tert-buty
- Aromatic hydroxybenzyl compounds for example 1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-2, 4,6-trimethylbenzene, 1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetrame-thylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol.
- Triazine Compounds for example 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1, 3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris-(3, 5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 2,4,
- Benzylphosphonates for example dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, droxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, the calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid.
- esters of ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols e.g. with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl) isocyanurate, N,N′-bis(hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylol-propane, 4-hydroxymethyl-1-phospha-2,6,7-trihydroxyphenyl)propi
- esters of ⁇ -(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid with mono- or polyhydric alcohols e.g. with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl) isocyanurate, N,N′-bis-(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-triox
- esters of ⁇ -(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols e.g. with methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2, 6,7-trioxabicyclo[2.2.2]octane.
- esters of 3,5-di-tert-butyl4-hydroxyphenyl acetic acid with mono- or polyhydric alcohols e.g. with methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.
- Aminic antioxidants for example N,N′-di-isopropyl-p-phenylenediamine, N,N′-di-sec-butyl-p-phenylenediamine, N,N′-bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N′-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N′-bis(1-methylheptyl)-p-phenylenediamine, N,N′-dicyclohexyl-p-phenylenediamine, N,N′-diphenyl-p-phenylenediamine, N,N′-bis(2-naphthyl)-p-phenylenediamine, N-isopropyl-N′-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N′-
- 2-(2′-Hvdroxyphenyl)benzotriazoles for example 2-(2′-hydroxy-5′-methylphenyl)-benzo-triazole, 2-(3′,5′-di-tert-butyl-2′-hydroxyphenyl)benzotriazole, 2-(5′-tert-butyl-2′-hydroxyphenyl) benzotriazole, 2-(2′-hydroxy-5′-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3′,5′-di-tert-butyl-2′-hydroxyphenyl)-5-chloro-benzotriazole, 2-(3′-tert-butyl- 2′-hydroxy-5′-methylphenyl)-5-chloro-benzotriazole, 2-(3′-sec-butyl-5′-tert-butyl-2′-hydroxyphenyl)benzotriazole, 2-(2′-hydroxy-4′-
- esters of substituted and unsubstituted benzoic acids as for example 4-tertbutyl-phenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis(4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate.
- Nickel compounds for example nickel complexes of 2,2′-thio-bis-[4-(1,1,3,3-tetramethylbutyl) phenol], such as the 1:1 or 1:2 complex, with or without additional ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibutyldithiocarbamate, nickel salts of the monoalkyl esters, e.g. the methyl or ethyl ester, of 4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid, nickel complexes of ketoximes, e.g. of 2-hydroxy-4-methylphenyl undecylketoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additional ligands.
- additional ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibutyldithiocarba
- Sterically hindered amines for example bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, linear or cyclic condensates of N,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octyla
- n or n′ is mainly from the range 3-5; or mixtures of these compounds.
- Oxamides for example 4,4′-dioctyloxyoxanilide, 2,2′-diethoxyoxanilide, 2,2′-dioctyloxy-5,5′-di-tert-butoxanilide, 2,2′-didodecyloxy-5,5′-di-tert-butoxanilide, 2-ethoxy-2′-ethyloxanilide, N,N′-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2-ethoxanilide and its mixture with 2-ethoxy-2′-ethyl-5,4′-di-tert-butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides and mixtures of o- and p-ethoxy-disubstituted oxanilides.
- Metal deactivators for example N,N′-diphenyloxamide, N-salicylal-N′-salicyloyl hydrazine, N,N′-bis(salicyloyl) hydrazine, N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazine, 3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide, N,N′-diacetyladipoyl dihydrazide, N,N′-bis(salicyl-oyl)oxalyl dihydrazide, N,N′-bis(salicyloyl)thiopropionyl dihydrazide.
- Phosphites and Phosphonites for example triphenyl phosphite, diphenyl alkyl phosphites, phenyl dialkyl phosphites, tris(nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl) phosphite, diisodecyl pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)-pentaerythritol diphosphite, diisodecyloxypentaerythritol diphosphite, diis
- Hydroxylamines for example, N,N-dibenzylhydroxylamine, N,N-diethylhydroxylamine, N,N-dioctylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-ditetradecylhydroxylamine, N,N-dihexadecylhydroxylamine, N,N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecylhydrox-ylamine, N-heptadecyl-N-octadecylhydroxylamine, N,N-dialkylhydroxylamine derived from hydrogenated tallow amine.
- Nitrones for example, N-benzyl-alpha-phenyl-nitrone, N-ethyl-alpha-methyl-nitrone, N-octyl-alpha-heptyl-nitrone, N-lauryl-alpha-undecyl-nitrone, N-tetradecyl-alpha-tridcyl-nitrone, N-hexadecyl-alpha-pentadecyl-nitrone, N-octadecyl-alpha-heptadecyl-nitrone, N-hexadecyl-alpha-heptadecyl-nitrone, N-ocatadecyl-alpha-pentadecyl-nitrone, N-heptadecyl-alpha-hepta-decyl-nitrone, N-octadecyl-alpha-hexadecyl-nitrone, N-
- Thiosyneraists for example, dilauryl thiodipropionate or distearyl thiodipropionate.
- Peroxide scavengers for example esters of ⁇ -thiodipropionic acid, for example the lauryl, stearyl, myristyl or tridecyl esters, mercaptobenzimidazole or the zinc salt of 2-mercapto-benzimidazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritol tetrakis( ⁇ -dodecylmercapto) propionate.
- esters of ⁇ -thiodipropionic acid for example the lauryl, stearyl, myristyl or tridecyl esters
- mercaptobenzimidazole or the zinc salt of 2-mercapto-benzimidazole zinc dibutyldithiocarbamate
- dioctadecyl disulfide pentaerythritol tetrakis( ⁇ -dodecyl
- Polyamide stabilisers for example, copper salts in combination with iodides and/or phosphorus compounds and salts of divalent manganese.
- Basic co-stabilisers for example, melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids for example calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate, antimony pyrocatecholate or zink pyrocatecholate.
- Basic co-stabilisers for example, melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids for example calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium
- Nucleating agents for example, inorganic substances such as talcum, metal oxides such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of, preferably, alkaline earth metals; organic compounds such as mono- or polycarboxylic acids and the salts thereof, e.g. 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymeric compounds such as ionic copolymers (ionomers).
- inorganic substances such as talcum, metal oxides such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of, preferably, alkaline earth metals
- organic compounds such as mono- or polycarboxylic acids and the salts thereof, e.g. 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate
- polymeric compounds such as ionic copolymers (ionomers
- Fillers and reinforcing agents for example, calcium carbonate, silicates, glass fibres, glass bulbs, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood flour and flours or fibers of other natural products, synthetic fibers.
- additives for example, oxygen absorbers, plasticisers, lubricants, emulsifiers, pigments, rheology additives, catalysts, flow-control agents, optical brighteners, flameproofing agents, antistatic agents and blowing agents.
- the nature and amount of the further stabilizers added are determined by the nature of the substrate to be stabilized and its intended use; in many cases from 0.01 to 5% by weight is used, based on the polymer to be stabilized.
- sterically hindered amines such as for example mentioned under item 2.6 are additionally present.
- a metal oxide or hydroxide such as ZnO, MgO or Mg(OH) 2 and/or a hydrotalcite.
- polyolefines further contain a metal carboxylate such as Ca— or Zn—stearate.
- additives of the invention and optional further components may be added to the polymer material individually or mixed with one another. If desired, the individual components can be mixed with one another before incorporation into the polymer for example by dry blending, compaction or in the melt.
- additives of the invention and optional further components into the polymer are carried out by known methods such as dry blending in the form of a powder, or wet mixing in the form of solutions, dispersions or suspensions for example in an inert solvent, water or oil.
- the additives of the invention and optional further additives may be incorporated, for example, before or after molding or also by applying the dissolved or dispersed additve or additive mixture to the polymer material, with or without subsequent evaporation of the solvent or the suspension/dispersion agent. They may be added directly into the processing apparatus (e.g. extruders, internal mixers, etc), e.g. as a dry mixture or powder or as solution or dispersion or suspension or melt.
- the incorporation can be carried out in any heatable container equipped with a stirrer, e.g. in a closed apparatus such as a kneader, mixer or stirred vessel.
- a stirrer e.g. in a closed apparatus such as a kneader, mixer or stirred vessel.
- the incorporation is preferably carried out in an extruder or in a kneader. It is immaterial whether processing takes place in an inert atmosphere or in the presence of oxygen.
- the addition of the additive or additive blend to the polymer can be carried out in all customary mixing machines in which the polymer is melted and mixed with the additives. Suitable machines are known to those skilled in the art. They are predominantly mixers, kneaders and extruders.
- the process is preferably carried out in an extruder by introducing the additive during processing.
- Particularly preferred processing machines are single-screw extruders, contrarotating and corotating twin-screw extruders, planetary-gear extruders, ring extruders or cokneaders. It is also possible to use processing machines provided with at least one gas removal compartment to which a vacuum can be applied.
- the screw length is 1 - 60 screw diameters, preferably 35-48 screw diameters.
- the rotational speed of the screw is preferably 10 - 600 rotations per minute (rpm), very particularly preferably 25-300 rpm.
- the maximum throughput is dependent on the screw diameter, the rotational speed and the driving force.
- the process of the present invention can also be carried out at a level lower than maximum throughput by varying the parameters mentioned or employing weighing machines delivering dosage amounts.
- additives of the invention and optional further additives can also be sprayed onto the polymer material. They are able to dilute other additives (for example the conventional additives indicated above) or their melts so that they can be sprayed also together with these additives onto the material. Addition by spraying during the deactivation of the polymerization catalysts is particularly advantageous; in this case, the steam evolved may be used for deactivation of the catalyst. In the case of spherically polymerized polyolefins it may, for example, be advantageous to apply the additives of the invention, optionally together with other additives, by spraying.
- the additives of the invention and optional further additives can also be added to the polymer in the form of a masterbatch (“concentrate”) which contains the components in a concentration of, for example, about 1% to about 40% and preferably 2% to about 20% by weight incorporated in a polymer.
- concentration a masterbatch
- the polymer must not be necessarily of identical structure than the polymer where the additives are added finally.
- the polymer can be used in the form of powder, granules, solutions, suspensions or in the form of latices.
- Incorporation can take place prior to or during the shaping operation, or by applying the dissolved or dispersed compound to the polymer, with or without subsequent evaporation of the solvent. In the case of elastomers, these can also be stabilized as latices.
- a further possibility for incorporating the additives of the invention into polymers is to add them before, during or directly after the polymerization of the corresponding monomers or prior to crosslinking. In this context the additive of the invention can be added as it is or else in encapsulated form (for example in waxes, oils or polymers).
- the plastic container or film or sheet is a multilayer construction of between 2 and 7 polymer layers containing a compound of formula (I), (II) or (Ib) or a mixture thereof in at least 1 layer.
- a polymer composition of the invention containing a relatively large amount of the compatible hydroxyphenyltriazine stabilizer, for example 1-15% by weight, is applied in a thin layer (e.g. 5-100 ⁇ ) to a shaped article made from a polymer containing little or no stabilizer of the invention.
- Application can be made at the same time as the shaping of the base article, for example by coextrusion.
- application can be made to the base article after it has been shaped, for example by lamination with a film or by coating with a solution.
- the external layer or layers of the finished article has or have the function of a UV filter which protects the interior of the article and/or inner layer(s) against UV light.
- Still a further subject of the invention is the use of a compound of formula (I), (II) or (Ib) or a mixture thereof which is incorporated into a plastic container or film or sheet, for content protection of greenhouses or packaged foodstuffs, beverages, pharmaceuticals, cosmetics or personal care products.
- % w/w percent by weight l liter; m.p. melting point or range; PP polypropylene; LDPE low density polyethylene; DSC differential scan calorimetry; NMR nuclear magnetic resonance (of 1 H, if not otherwise indicated); ⁇ at ⁇ max molar extinction coefficient (l ⁇ mol ⁇ 1 cm ⁇ 1 ) at long wavelength UV absorption maximum; Mn number average of molecular mass (g/mol) as determined by GPC; GPC gel permeation chromatography; PDI polydispersity (ratio of mass and number average of molecular weight).
- the molecular weight parameters (Mn, Mw, PDI) are determined by GPC (Gel Permeation Chromatography).
- GPC Gel Permeation Chromatography
- the GPC measurements are carried out on a Perkin Elmer LC 50 liquid chromatograph equipped with a reflective index Perkin Elmer LC 30 and the data are calculated by using a Perkin Elmer software (TurboSEC). All GPC measurements are carried out by using 0.02 M di-ethanol-amine solution in chromatographic grade tetrahydrofuran (THF) as solvent at 45° C.
- THF chromatographic grade tetrahydrofuran
- the columns used are PLGEL (Polymer Laboratories) 300 mm ⁇ 7.5 mm, stationary phase 3 mm Mixed E, supplied by Polymer Laboratories.
- Polystyrene standards are used for the calibration curve. Visual melting points and melting ranges are measured by using a Gallenkamp equipment. The extinction coefficients (e) are calculated by recording the UV spectra of the products in methylene chloride or toluene solutions on a Perkin Elmer Lambda 2S spectrophotometer.
- ⁇ at maximum ⁇ is 52400 Imol ⁇ 1 cm ⁇ 1 .
- ⁇ at maximum ⁇ is 414000 Imol ⁇ 1 cm ⁇ 1 .
- intermediate 3 a is isolated as a yellow powder (mp 216°).
- ⁇ at maximum ⁇ is 42000 Imol ⁇ 1 cm ⁇ 1 .
- ⁇ at maximum ⁇ is 78700 Imol ⁇ 1 cm ⁇ 1 .
- ⁇ at maximum ⁇ is 38900 Imol ⁇ 1 cm 1 .
- ⁇ at ⁇ is 412001 mol ⁇ 1 cm 1 .
- a mixture of 25 g (0.043 mol) of compound from example A1 part a, 20.9 g (0.103 mol) of dodecanediol, 6.2 g (0.043 mol) of dimethylsuccinate and 0.5 g of p-toluenesulfonic acid (pTSA) in 30 ml of mesitylene is heated up to 160° C. and the distilled mesitylene is discarded. After about 6 hours the mixture is cooled and 200 ml of toluene are added. The organic layer is washed twice with 100 ml of a water solution of sodium carbonate, dried under sodium sulphate and evaporated under reduced pressure.
- pTSA p-toluenesulfonic acid
- ⁇ at max ⁇ is 37071 I mol ⁇ 1 cm ⁇ 1 .
- ⁇ at max ⁇ is 469111 mol ⁇ 1 cm ⁇ 1 .
- ⁇ at max ⁇ is 42473 I mol ⁇ 1 cm ⁇ 1 .
- ⁇ at max ⁇ is 54315 I mol ⁇ 1 cm ⁇ 1 .
- ⁇ at max ⁇ is 53891 I mol ⁇ 1 cm ⁇ 1 .
- a suspension of 20 g (0.05 mole) of 2-(4-methoxyphenyl)-4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazine in 100 ml ethylcellosolve is heated to 70° C.
- 44 g potassium carbonate are added and 40.16 g (0.32 mole) 2-bromoethanol are added dropwise over 2 hrs.
- the mixture is heated for a further 3 hours at 70° C., then filtered hot to remove inorganic salts.
- the filtrate is cooled to 0° C. and allowed to crystallise.
- the solid is filtered off and dried at 60° C.
- a formulation containing 2% by weight of compound 101 is prepared, according to the following procedure: the compound is mixed with milled LLDPE (Dowlex® NG 5056E, Dow Chemical), characterized by a density of 0.919 g/cm 3 and a melt flow index (190° C./2.16 Kg) of 1.1) and extruded at a maximum temperature of 230° C. in a OMC twin-screw extruder. The granules so obtained are blown in a lab-scale Formac blow-extruder at a maximum temperature of 230° C. to give a film of about 50 ⁇ m thickness.
- LLDPE Low Dens® NG 5056E, Dow Chemical
- a UV-Vis spectrum of the film is recorded in the range 200-800 nm by means of a Perkin-Elmer lambda 20 spectrophotometer, equipped with a RSA-PE-20 Labsphere integrating sphere.
- the spectrum so obtained displays a strong absorption in the UV range with a maximum at about 310 nm and a shoulder around 345 nm, while the absorption is negligible in the visible part of the spectrum; the transmittance is 13% in the range 280-400 nm and of 7% in the range 280-390 nm. Transmittance value is 31 % at 380 nm.
- a piece of the film is stored at room temperature inside an envelope and between two pieces of paper.
- the film is periodically inspected visually to verify possible exudation (blooming) of the compound from the bulk of the polymeric matrix. After 1500 hours no visual blooming occurrs.
- Another piece of the film is placed in a forced circulating air oven at 60° C. for the same reason. Again, after 1500 hours no visual blooming occurrs.
- a formulation containing 2% by weight of compound 102 was prepared, according to the procedure described in Example 1.
- the 50 ⁇ m thick film so obtained was subjected to UV-Vis spectrophotometry, as described in Example 1.
- the film displays a strong absorption in the UV range with a maximum at 359 nm, while the absorption is negligible in the visible part of the spectrum; the transmittance is of 9% in the range 280-400 nm and of 5% in the range 280-390 nm. Transmittance value is 6% at 380 nm.
- a formulation containing 1.5% by weight of compound 107 was prepared, according to the procedure described in Example 1.
- the 50 ⁇ m thick film so obtained was subjected to UV-Vis spectrophotometry, as described in Example 1.
- the film displays a strong absorption in the UV range with a maximum at 345 nm, while the absorption is negligible in the visible part of the spectrum; the transmittance is of 11% in the range 280-400 nm and of 7% in the range 280-390 nm. Transmittance value is 15% at 380 nm.
- the films containing the above compounds behave as those examples B1, B2 and B3, both at room temperature and at 60° C. in a forced circulating air oven.
- the films are investigated further as regards the compatibility of the additives therein, in terms of resistance to extraction by lipophilic liquids. To do so, pieces of the films described in this example are dipped into olive oil inside a covered Petri dish and exposed to heat at 60° C. in for 10 days. At the end of this period the films are taken away from the oil, rinsed with n-hexane to remove the oil in exces which could not drip spontaneously from the film, dried and finally subjected to UV spectroscopy, measuring the retained absorption at maxium of the additive. The results are reported in the following table. % retained absorption at Compound maximum 110 95 113 93 114 97 117 97 120 95 121 98
- UV absorbers of the invention show good persistence in the film.
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WO2024181218A1 (ja) * | 2023-03-02 | 2024-09-06 | 信越化学工業株式会社 | トリアジン化合物及びその製造方法 |
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US20060052491A1 (en) * | 2002-10-02 | 2006-03-09 | Adalbert Braig | Synergistic uv absorber combination |
US7332105B2 (en) | 2002-10-02 | 2008-02-19 | Ciba Specialty Chemicals Corporation | Synergistic UV absorber combination |
US20060235116A1 (en) * | 2003-05-26 | 2006-10-19 | Dario Lazzari | Highly compatible and non-migratory polymeric uv-absorber |
US20110089384A1 (en) * | 2003-05-26 | 2011-04-21 | Dario Lazzari | Highly compatible and non-migratory polymeric uv-absorber |
US20060252857A1 (en) * | 2003-05-27 | 2006-11-09 | Schaefer Thomas | Aminoaryl-1-3-5-triazines and their use as uv absorbers |
US20050282995A1 (en) * | 2004-06-16 | 2005-12-22 | Asahi Denka Co., Ltd. | Polyester resin container with improved weatherability |
US7132499B2 (en) * | 2004-06-16 | 2006-11-07 | Asahi Denka Co., Ltd. | Polyester resin container with improved weatherability |
US9062143B2 (en) | 2008-02-08 | 2015-06-23 | Dow Global Technologies Llc | Water-redispersible polymer powder |
US9658363B2 (en) | 2011-04-01 | 2017-05-23 | 3M Innovative Properties Company | Films including triazine-based ultraviolet absorbers |
US10598823B2 (en) | 2011-04-01 | 2020-03-24 | 3M Innovative Properties Company | Films including triazine-based ultraviolet absorbers |
US8366822B2 (en) | 2011-06-20 | 2013-02-05 | Dow Global Technologies Llc | Cementitious tile adhesives and method of applying the same to a tile substrate |
US9951180B2 (en) | 2013-10-02 | 2018-04-24 | Adeka Corporation | Ultraviolet-ray-absorbing polycarbonate |
US11015055B2 (en) | 2016-06-09 | 2021-05-25 | Adeka Corporation | Resin composition |
WO2019244986A1 (ja) | 2018-06-21 | 2019-12-26 | 凸版印刷株式会社 | 保護フィルムおよびシート |
KR20210021541A (ko) | 2018-06-21 | 2021-02-26 | 도판 인사츠 가부시키가이샤 | 보호 필름 및 시트 |
US12031028B2 (en) | 2019-02-01 | 2024-07-09 | Lg Chem, Ltd. | Polyamide resin film and resin laminate using the same |
CN115304753A (zh) * | 2022-10-10 | 2022-11-08 | 广东乔艺塑胶有限公司 | 一种高透明耐化学腐蚀共聚聚酯化妆品包装材料及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
US20080032078A1 (en) | 2008-02-07 |
WO2003004557A1 (en) | 2003-01-16 |
JP4239170B2 (ja) | 2009-03-18 |
AU2002321111B2 (en) | 2006-12-21 |
JP2004533529A (ja) | 2004-11-04 |
US20070161726A1 (en) | 2007-07-12 |
JP2009046496A (ja) | 2009-03-05 |
TW200942523A (en) | 2009-10-16 |
US7294714B2 (en) | 2007-11-13 |
CA2452561A1 (en) | 2003-01-16 |
CN1522275A (zh) | 2004-08-18 |
US7638626B2 (en) | 2009-12-29 |
TWI318208B (en) | 2009-12-11 |
EP1401942A1 (en) | 2004-03-31 |
TWI316513B (en) | 2009-11-01 |
CN1231530C (zh) | 2005-12-14 |
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