WO2003035735A1 - Low color, low sodium benzoxazinone uv absorbers and process for making same - Google Patents
Low color, low sodium benzoxazinone uv absorbers and process for making same Download PDFInfo
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- WO2003035735A1 WO2003035735A1 PCT/US2002/028869 US0228869W WO03035735A1 WO 2003035735 A1 WO2003035735 A1 WO 2003035735A1 US 0228869 W US0228869 W US 0228869W WO 03035735 A1 WO03035735 A1 WO 03035735A1
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- WIPO (PCT)
- Prior art keywords
- compound
- resins
- less
- anhydride
- agents
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 28
- 239000006096 absorbing agent Substances 0.000 title description 10
- JOJWUJUKJNUQLH-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one;sodium Chemical compound [Na].C1=CC=C2ONC(=O)CC2=C1 JOJWUJUKJNUQLH-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 16
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 16
- 239000011734 sodium Substances 0.000 claims abstract description 16
- 238000001953 recrystallisation Methods 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 claims abstract 5
- -1 phenylene, diphenylene Chemical group 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 150000001266 acyl halides Chemical class 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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- 239000011347 resin Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 7
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- 229920000728 polyester Polymers 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 229920000058 polyacrylate Polymers 0.000 claims description 6
- 229920001470 polyketone Polymers 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
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- 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
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- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 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 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 3
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 claims description 3
- 229920000638 styrene acrylonitrile Polymers 0.000 claims description 3
- 230000000475 sunscreen effect Effects 0.000 claims description 3
- 239000000516 sunscreening agent Substances 0.000 claims description 3
- 229920001169 thermoplastic Polymers 0.000 claims description 3
- 239000004416 thermosoftening plastic Substances 0.000 claims description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 2
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 229920000178 Acrylic resin Polymers 0.000 claims description 2
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- 238000006845 Michael addition reaction Methods 0.000 claims description 2
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 2
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 claims description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 2
- 229920003180 amino resin Polymers 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 235000006708 antioxidants Nutrition 0.000 claims description 2
- 239000002216 antistatic agent Substances 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
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- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 2
- 239000008395 clarifying agent Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229920005669 high impact polystyrene Polymers 0.000 claims description 2
- 150000002443 hydroxylamines Chemical class 0.000 claims description 2
- 239000000976 ink Substances 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
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- 150000004658 ketimines Chemical class 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 239000006078 metal deactivator Substances 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- NZZGQZMNFCTNAM-UHFFFAOYSA-N naphthalene-2,6-dicarbonyl chloride Chemical compound C1=C(C(Cl)=O)C=CC2=CC(C(=O)Cl)=CC=C21 NZZGQZMNFCTNAM-UHFFFAOYSA-N 0.000 claims description 2
- 229920003052 natural elastomer Polymers 0.000 claims description 2
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- 150000002816 nickel compounds Chemical class 0.000 claims description 2
- 239000002667 nucleating agent Substances 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
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- QMRNDFMLWNAFQR-UHFFFAOYSA-N prop-2-enenitrile;prop-2-enoic acid;styrene Chemical compound C=CC#N.OC(=O)C=C.C=CC1=CC=CC=C1 QMRNDFMLWNAFQR-UHFFFAOYSA-N 0.000 claims description 2
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- 230000000996 additive effect Effects 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 abstract description 10
- 238000000746 purification Methods 0.000 abstract description 3
- TXJUTRJFNRYTHH-UHFFFAOYSA-N 1h-3,1-benzoxazine-2,4-dione Chemical compound C1=CC=C2C(=O)OC(=O)NC2=C1 TXJUTRJFNRYTHH-UHFFFAOYSA-N 0.000 description 18
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- BBITXNWQALLODC-UHFFFAOYSA-N 2-[4-(4-oxo-3,1-benzoxazin-2-yl)phenyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C3=CC=C(C=C3)C=3OC(C4=CC=CC=C4N=3)=O)=NC2=C1 BBITXNWQALLODC-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
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- 238000002360 preparation method Methods 0.000 description 6
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- 239000002904 solvent Substances 0.000 description 4
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- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
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- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
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- IDVDCFLVRHMYHZ-UHFFFAOYSA-N n-[4-(4-oxo-3,1-benzoxazin-2-yl)phenyl]benzamide Chemical compound C=1C=C(C=2OC(=O)C3=CC=CC=C3N=2)C=CC=1NC(=O)C1=CC=CC=C1 IDVDCFLVRHMYHZ-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- XKVBZVQCHAXMOF-UHFFFAOYSA-N n-methyl-4-(4-oxo-3,1-benzoxazin-2-yl)-n-phenylbenzamide Chemical compound C=1C=C(C=2OC(=O)C3=CC=CC=C3N=2)C=CC=1C(=O)N(C)C1=CC=CC=C1 XKVBZVQCHAXMOF-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 1
- WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 1
- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
- JAZLVNXWYDFQFE-UHFFFAOYSA-N oxalyl dibromide Chemical compound BrC(=O)C(Br)=O JAZLVNXWYDFQFE-UHFFFAOYSA-N 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-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
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000004079 stearyl 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])[H] 0.000 description 1
- 239000000126 substance Substances 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
- RCRYHUPTBJZEQS-UHFFFAOYSA-N tetradecanoyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCC RCRYHUPTBJZEQS-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- C08K5/357—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02778247A EP1438352B1 (en) | 2001-10-22 | 2002-09-12 | Low color, low sodium benzoxazinone uv absorbers and process for making same |
DE60236528T DE60236528D1 (en) | 2001-10-22 | 2002-09-12 | LOW-TINTED SODIUM ARM BENZOXAZINONE UV ABSORBERS AND METHOD OF PREPARING THEM |
JP2003538247A JP2005507006A (en) | 2001-10-22 | 2002-09-12 | Low color, low sodium benzoxazinone UV absorbers and their preparation |
AT02778247T ATE469189T1 (en) | 2001-10-22 | 2002-09-12 | LOW COLORED LOW SODIUM BENZOXAZINONE UV ABSORBERS AND METHOD FOR THE PRODUCTION THEREOF |
HU0401817A HU230474B1 (en) | 2001-10-22 | 2002-09-12 | Low color, low sodium benzoxazinone uv absorbers and process for making same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US33108801P | 2001-10-22 | 2001-10-22 | |
US60/331,088 | 2001-10-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003035735A1 true WO2003035735A1 (en) | 2003-05-01 |
Family
ID=23292575
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2002/028869 WO2003035735A1 (en) | 2001-10-22 | 2002-09-12 | Low color, low sodium benzoxazinone uv absorbers and process for making same |
Country Status (8)
Country | Link |
---|---|
US (1) | US6774232B2 (en) |
EP (1) | EP1438352B1 (en) |
JP (2) | JP2005507006A (en) |
AT (1) | ATE469189T1 (en) |
DE (1) | DE60236528D1 (en) |
HU (1) | HU230474B1 (en) |
TW (1) | TW583242B (en) |
WO (1) | WO2003035735A1 (en) |
Cited By (8)
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JP2006124416A (en) * | 2004-10-26 | 2006-05-18 | Teijin Chem Ltd | Light-diffusing resin composition and its manufacturing method |
JP2006124600A (en) * | 2004-11-01 | 2006-05-18 | Teijin Chem Ltd | Highly light-reflecting polycarbonate resin composition and method for producing the same |
JP2006182980A (en) * | 2004-12-28 | 2006-07-13 | Unitika Ltd | Polyarylate resin composition and molded article comprising the same |
US7148313B2 (en) | 2004-03-26 | 2006-12-12 | Teijin Chemicals, Ltd. | Polycarbonate resin composition and molded articles thereof |
WO2011064897A1 (en) | 2009-11-26 | 2011-06-03 | 帝人化成株式会社 | Bis-benzoxazinone compound |
WO2011093478A1 (en) | 2010-01-27 | 2011-08-04 | 帝人株式会社 | Film |
US9550885B2 (en) | 2011-02-18 | 2017-01-24 | Midori Anzen Co., Ltd. | Transparent resin composition having good chemical resistance, durability and stability under natural environmental conditions, harsher natural environmental conditions, and similar or harsher usage conditions, and product using same |
CN110437171A (en) * | 2019-07-02 | 2019-11-12 | 江苏丹霞新材料有限公司 | The preparation method of double benzoxazinone ultraviolet absorbing agents |
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KR100583387B1 (en) * | 2001-11-20 | 2006-05-25 | 다케모토 유시 가부시키 가이샤 | Ultraviolet radiation absorbents for thermoplastic polymers and methods of producing same |
US7157547B2 (en) * | 2003-11-13 | 2007-01-02 | Eastman Chemical Company | Ultraviolet blocking composition for protection of package or container contents |
US7192471B2 (en) * | 2004-09-24 | 2007-03-20 | Honeywell International Inc. | Aryl-ureido benzoxazinone compounds |
US20060089433A1 (en) * | 2004-10-21 | 2006-04-27 | Palram Industries (1990) Ltd. | Ultraviolet protected polyethersulfones |
DE602006010315D1 (en) * | 2006-01-05 | 2009-12-24 | Temsa Internat Inc | Process for the preparation of a benzoxazinone |
WO2007083290A2 (en) * | 2006-01-18 | 2007-07-26 | Palram Industries (1990) Ltd. | Ultraviolet protected polyethersulfones |
US7879846B2 (en) | 2006-09-21 | 2011-02-01 | Kyorin Pharmaceutical Co.., Ltd. | Serine hydrolase inhibitors |
JP4954700B2 (en) * | 2006-12-29 | 2012-06-20 | 株式会社日本触媒 | Thermoplastic resin composition and extruded film or sheet |
EP1972624A1 (en) * | 2007-03-23 | 2008-09-24 | Clariant International Ltd. | Benzoxazinones and their use as ultraviolet light absorbers |
JP5276878B2 (en) * | 2007-09-27 | 2013-08-28 | 富士フイルム株式会社 | Method for producing benzoxazinone compound |
JP5129597B2 (en) * | 2008-02-07 | 2013-01-30 | 富士フイルム株式会社 | Ultraviolet absorber, condensed ring compound and method for producing the same |
JP2010132846A (en) * | 2008-03-30 | 2010-06-17 | Fujifilm Corp | Resin molded product and polymer film |
JP5591453B2 (en) * | 2008-03-31 | 2014-09-17 | 富士フイルム株式会社 | Ultraviolet absorber and polymer composition containing the same |
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JP6026946B2 (en) | 2013-04-19 | 2016-11-16 | 出光興産株式会社 | Polycarbonate resin composition and molded article |
AU2015349771C1 (en) | 2014-11-20 | 2020-06-11 | Cytec Industries Inc. | Stabilizer compositions and methods for using same for protecting organic materials from UV light and thermal degradation |
US10590240B2 (en) | 2015-06-30 | 2020-03-17 | Sabic Global Technologies B.V. | Thermoplastic composition with balanced chemical resistance and impact properties |
US20170002177A1 (en) * | 2015-06-30 | 2017-01-05 | Sabic Global Technologies B.V. | Uv-stabilized polysulfones-v4 |
JP6027211B2 (en) * | 2015-11-10 | 2016-11-16 | 出光興産株式会社 | Polycarbonate resin composition and molded article |
EP4251689A1 (en) | 2020-11-27 | 2023-10-04 | Cytec Industries, Inc. | Compositions and methods for protecting organic polymeric materials from discoloration due to exposure to uv-c light |
WO2023278282A1 (en) | 2021-06-29 | 2023-01-05 | Cytec Industries Inc. | Compositions and methods for protecting coatings from the deleterious effects of exposure to uv-c light |
WO2023129464A1 (en) | 2022-01-01 | 2023-07-06 | Cytec Industries Inc. | Polymer compositions having densification accelerators and rotational molding processes for making hollow articles therefrom |
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US4446262A (en) * | 1981-06-19 | 1984-05-01 | Teijin Limited | Protection from ultraviolet light by use of novel ultraviolet absorber |
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WO1998019862A1 (en) * | 1996-11-04 | 1998-05-14 | Eastman Chemical Company | Uv stabilized multi-layer structures with detectable uv protective layers and a method of detection |
WO1999048878A1 (en) * | 1998-03-24 | 1999-09-30 | Novo Nordisk A/S | Heterocyclic compounds regulating clotting |
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JPS6211744A (en) * | 1986-07-28 | 1987-01-20 | Teijin Ltd | Protection from ultraviolet ray using novel ultraviolet absorber |
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-
2002
- 2002-07-31 US US10/209,436 patent/US6774232B2/en not_active Expired - Lifetime
- 2002-09-12 EP EP02778247A patent/EP1438352B1/en not_active Expired - Lifetime
- 2002-09-12 JP JP2003538247A patent/JP2005507006A/en not_active Withdrawn
- 2002-09-12 HU HU0401817A patent/HU230474B1/en unknown
- 2002-09-12 DE DE60236528T patent/DE60236528D1/en not_active Expired - Lifetime
- 2002-09-12 AT AT02778247T patent/ATE469189T1/en not_active IP Right Cessation
- 2002-09-12 WO PCT/US2002/028869 patent/WO2003035735A1/en active Application Filing
- 2002-09-27 TW TW091122352A patent/TW583242B/en not_active IP Right Cessation
-
2010
- 2010-04-02 JP JP2010086335A patent/JP5352515B2/en not_active Expired - Fee Related
Patent Citations (9)
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US3887550A (en) * | 1969-11-20 | 1975-06-03 | Sherwin Williams Co | Method for producing heterocyclic acid anhydrides |
US3989698A (en) * | 1975-02-20 | 1976-11-02 | The Sherwin-Williams Company | Process for preparing benzoxazines |
US4446262A (en) * | 1981-06-19 | 1984-05-01 | Teijin Limited | Protection from ultraviolet light by use of novel ultraviolet absorber |
EP0315138A1 (en) * | 1987-11-05 | 1989-05-10 | Hoechst Aktiengesellschaft | Process for the preparation of 6-chloroisatoic anhydride |
DE4101380A1 (en) * | 1991-01-18 | 1992-07-23 | Basf Ag | PROCESS FOR THE PREPARATION OF 4H-3,1-BENZOXAZINE-4-ONEN |
WO1993022300A1 (en) * | 1992-04-23 | 1993-11-11 | Bp Chemicals Limited | Process for the production of 2-phenyl-benzoxazin-4-one |
EP0781767A1 (en) * | 1995-12-26 | 1997-07-02 | Sumitomo Chemical Company, Limited | Process for producing isatoic anhydrides |
WO1998019862A1 (en) * | 1996-11-04 | 1998-05-14 | Eastman Chemical Company | Uv stabilized multi-layer structures with detectable uv protective layers and a method of detection |
WO1999048878A1 (en) * | 1998-03-24 | 1999-09-30 | Novo Nordisk A/S | Heterocyclic compounds regulating clotting |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7148313B2 (en) | 2004-03-26 | 2006-12-12 | Teijin Chemicals, Ltd. | Polycarbonate resin composition and molded articles thereof |
JP2006124416A (en) * | 2004-10-26 | 2006-05-18 | Teijin Chem Ltd | Light-diffusing resin composition and its manufacturing method |
JP2006124600A (en) * | 2004-11-01 | 2006-05-18 | Teijin Chem Ltd | Highly light-reflecting polycarbonate resin composition and method for producing the same |
JP2006182980A (en) * | 2004-12-28 | 2006-07-13 | Unitika Ltd | Polyarylate resin composition and molded article comprising the same |
WO2011064897A1 (en) | 2009-11-26 | 2011-06-03 | 帝人化成株式会社 | Bis-benzoxazinone compound |
EP2505585A1 (en) * | 2009-11-26 | 2012-10-03 | Teijin Chemicals, Ltd. | Bis-benzoxazinone compound |
EP2505585A4 (en) * | 2009-11-26 | 2012-10-24 | Teijin Chemicals Ltd | Bis-benzoxazinone compound |
EP3056488A1 (en) | 2009-11-26 | 2016-08-17 | Teijin Chemicals, Ltd. | Bisbenzoxazinone compound |
WO2011093478A1 (en) | 2010-01-27 | 2011-08-04 | 帝人株式会社 | Film |
US9550885B2 (en) | 2011-02-18 | 2017-01-24 | Midori Anzen Co., Ltd. | Transparent resin composition having good chemical resistance, durability and stability under natural environmental conditions, harsher natural environmental conditions, and similar or harsher usage conditions, and product using same |
CN110437171A (en) * | 2019-07-02 | 2019-11-12 | 江苏丹霞新材料有限公司 | The preparation method of double benzoxazinone ultraviolet absorbing agents |
CN110437171B (en) * | 2019-07-02 | 2021-11-09 | 江苏丹霞新材料有限公司 | Preparation method of bis-benzoxazinone ultraviolet absorbent |
Also Published As
Publication number | Publication date |
---|---|
ATE469189T1 (en) | 2010-06-15 |
EP1438352B1 (en) | 2010-05-26 |
HU230474B1 (en) | 2016-07-28 |
EP1438352A1 (en) | 2004-07-21 |
DE60236528D1 (en) | 2010-07-08 |
US20030096889A1 (en) | 2003-05-22 |
JP2010189408A (en) | 2010-09-02 |
JP5352515B2 (en) | 2013-11-27 |
JP2005507006A (en) | 2005-03-10 |
TW583242B (en) | 2004-04-11 |
US6774232B2 (en) | 2004-08-10 |
HUP0401817A2 (en) | 2005-03-29 |
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Legal Events
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