GB2368063A - 3-Aryl-5-substituted-3H-benzofuran-2-one derivatives and their use as stabilizers of organic material against degradation by light, oxygen or heat - Google Patents
3-Aryl-5-substituted-3H-benzofuran-2-one derivatives and their use as stabilizers of organic material against degradation by light, oxygen or heat Download PDFInfo
- Publication number
- GB2368063A GB2368063A GB0105372A GB0105372A GB2368063A GB 2368063 A GB2368063 A GB 2368063A GB 0105372 A GB0105372 A GB 0105372A GB 0105372 A GB0105372 A GB 0105372A GB 2368063 A GB2368063 A GB 2368063A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- substituted
- c4alkyl
- oxygen
- phenylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 239000001301 oxygen Substances 0.000 title claims abstract description 23
- 239000011368 organic material Substances 0.000 title claims abstract description 14
- 239000003381 stabilizer Substances 0.000 title claims abstract description 9
- 230000015556 catabolic process Effects 0.000 title abstract description 5
- 238000006731 degradation reaction Methods 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 150000003254 radicals Chemical class 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000002402 hexoses Chemical class 0.000 claims description 12
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims 4
- 230000006866 deterioration Effects 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 230000000087 stabilizing effect Effects 0.000 claims 2
- 102100025597 Caspase-4 Human genes 0.000 claims 1
- 101100273284 Homo sapiens CASP4 gene Proteins 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- CBCIHIVRDWLAME-UHFFFAOYSA-N hexanitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O CBCIHIVRDWLAME-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 239000000654 additive Substances 0.000 abstract description 3
- 239000003963 antioxidant agent Substances 0.000 abstract description 3
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- -1 silver halide Chemical class 0.000 description 104
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 229940093499 ethyl acetate Drugs 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000004956 cyclohexylene group Chemical group 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000005236 alkanoylamino group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000004977 cycloheptylene group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004978 cyclooctylene group Chemical group 0.000 description 2
- 125000004979 cyclopentylene group Chemical group 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- MCSKRVKAXABJLX-UHFFFAOYSA-N pyrazolo[3,4-d]triazole Chemical compound N1=NN=C2N=NC=C21 MCSKRVKAXABJLX-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JUXXUMCETXNMIJ-UHFFFAOYSA-N 2,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=CC(C(C)(C)CC)=C1O JUXXUMCETXNMIJ-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005975 2-phenylethyloxy group Chemical group 0.000 description 1
- XPEZANRRNFUCFO-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-3h-1-benzofuran-2-one Chemical class OC1=CC=CC=C1C1C2=CC=CC=C2OC1=O XPEZANRRNFUCFO-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- GIXLHWMKKXPOFH-UHFFFAOYSA-N 3-hydroxy-5,7-bis(2-methylbutan-2-yl)-3h-1-benzofuran-2-one Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC2=C1OC(=O)C2O GIXLHWMKKXPOFH-UHFFFAOYSA-N 0.000 description 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BSXOSQBMEPSIHD-UHFFFAOYSA-N 5,7-bis(2-methylbutan-2-yl)-3-(4-propan-2-ylphenyl)-3h-1-benzofuran-2-one Chemical compound O=C1OC=2C(C(C)(C)CC)=CC(C(C)(C)CC)=CC=2C1C1=CC=C(C(C)C)C=C1 BSXOSQBMEPSIHD-UHFFFAOYSA-N 0.000 description 1
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 1
- XVZXOLOFWKSDSR-UHFFFAOYSA-N Cc1cc(C)c([C]=O)c(C)c1 Chemical group Cc1cc(C)c([C]=O)c(C)c1 XVZXOLOFWKSDSR-UHFFFAOYSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 125000001124 arachidoyl group Chemical group O=C([*])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
- 125000001204 arachidyl 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])[H] 0.000 description 1
- 125000003910 behenoyl group Chemical group O=C([*])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
- 125000002511 behenyl 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])[H] 0.000 description 1
- 125000001231 benzoyloxy group Chemical class C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000006640 cycloheptyl carbonyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 125000003074 decanoyl group Chemical group [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(*)=O 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- SZZWLAZADBEDQP-UHFFFAOYSA-N dimethylcyclopentylene Natural products CC1=C(C)CCC1 SZZWLAZADBEDQP-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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
- 239000007788 liquid Substances 0.000 description 1
- JESHZQPNPCJVNG-UHFFFAOYSA-L magnesium;sulfite Chemical compound [Mg+2].[O-]S([O-])=O JESHZQPNPCJVNG-UHFFFAOYSA-L 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- TVUZOWCUYWPFPN-UHFFFAOYSA-N methyl 3-(3-tert-butyl-4-hydroxyphenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(O)C(C(C)(C)C)=C1 TVUZOWCUYWPFPN-UHFFFAOYSA-N 0.000 description 1
- CHJFKMCTASXKEY-UHFFFAOYSA-N methyl 3-(7-tert-butyl-3-hydroxy-2-oxo-3h-1-benzofuran-5-yl)propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC2=C1OC(=O)C2O CHJFKMCTASXKEY-UHFFFAOYSA-N 0.000 description 1
- XIVWCAGXGKJGHC-UHFFFAOYSA-N methyl 5-(3-hydroxy-2-oxo-7-propan-2-yl-3h-1-benzofuran-5-yl)-5-methylhexanoate Chemical compound CC(C)C1=CC(C(C)(C)CCCC(=O)OC)=CC2=C1OC(=O)C2O XIVWCAGXGKJGHC-UHFFFAOYSA-N 0.000 description 1
- YMFAHAMEGVLUCR-UHFFFAOYSA-N methyl 5-(4-hydroxy-3-propan-2-ylphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC=C(O)C(C(C)C)=C1 YMFAHAMEGVLUCR-UHFFFAOYSA-N 0.000 description 1
- DPSHXDQTKIRAKO-UHFFFAOYSA-N methyl 5-[2,3-dimethyl-5-(2-oxo-7-propan-2-yl-3h-1-benzofuran-3-yl)phenyl]-5-methylhexanoate Chemical compound CC1=C(C)C(C(C)(C)CCCC(=O)OC)=CC(C2C3=C(C(=CC=C3)C(C)C)OC2=O)=C1 DPSHXDQTKIRAKO-UHFFFAOYSA-N 0.000 description 1
- JFYAIHIJURBEBA-UHFFFAOYSA-N methyl 5-[3-(2,3-dimethylphenyl)-2-oxo-7-propan-2-yl-3h-1-benzofuran-5-yl]-5-methylhexanoate Chemical compound O=C1OC=2C(C(C)C)=CC(C(C)(C)CCCC(=O)OC)=CC=2C1C1=CC=CC(C)=C1C JFYAIHIJURBEBA-UHFFFAOYSA-N 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])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
- 125000001421 myristyl 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])[H] 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical class 0.000 description 1
- 125000001402 nonanoyl group Chemical group O=C([*])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
- 125000001400 nonyl 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])[H] 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- VNFLOVICVCYCIH-UHFFFAOYSA-N octyl 2-(3-tert-butyl-4-hydroxyphenoxy)propanoate Chemical compound CCCCCCCCOC(=O)C(C)OC1=CC=C(O)C(C(C)(C)C)=C1 VNFLOVICVCYCIH-UHFFFAOYSA-N 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([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])[H] 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])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
- 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
- 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940095050 propylene Drugs 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 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
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920005613 synthetic organic polymer Polymers 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])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
- 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
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/392—Additives
- G03C7/39208—Organic compounds
- G03C7/3924—Heterocyclic
- G03C7/39268—Heterocyclic the nucleus containing only oxygen as hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Novel compounds of the formula V or VI <EMI ID=1.1 HE=86 WI=96 LX=599 LY=647 TI=CF> <PC>wherein<BR> R<SB>4</SB> is -(CH<SB>2</SB>)<SB>s</SB>-COR'<SB>15</SB> or -CH(CH<SB>3</SB>)-COR<SB>15</SB> or -C<SB>t</SB>H<SB>2t</SB>-COR<SB>15</SB>, wherein C<SB>t</SB>H<SB>2t</SB> is a straight chain or branched alkylene moiety; or R<SB>4</SB> is -O-(C<SB>v</SB>H<SB>2v</SB>)-COR<SB>15</SB>; -O-(CH<SB>2</SB>)<SB>q</SB>-OR<SB>32</SB>;<BR> -OCH<SB>2</SB>-CH(OH)-CH<SB>2</SB>-R<SB>15</SB>; or -OCH<SB>2</SB>-CH(OH)-CH<SB>2</SB>-OR<SB>32</SB>;<BR> R'<SB>7</SB> is C<SB>1</SB>-C<SB>4</SB>alkyl and R'<SB>8</SB> is hydrogen or C<SB>1</SB>-C<SB>4</SB>alkyl; and the remaining residues are as defined in claim 1 (and further remaining residues are as defined in GB 2343007), can be used as additives, for example as dye stabilizer, as scavengers for oxidised developers, or as an antioxidant or stabilizer for organic materials against degradation by light, oxygen and/or heat.
Description
Colour Photographic Material
The present invention relates to colour photographic material comprising a certain lactone (benzofuran-2-one) type compound, to the use of this compound as an additive to photographic material, especially as scavenger for the oxidised form of the developer (Doxscavenger), to some new compounds of the benzofuran-2-one class, and their use as stabilisers for organic material against oxidative, thermal and/or light-induced degradation.
It is well known that one of the problems associated with colour photography is the diffusion of the oxidised colour developer away from the light sensitive silver halide emulsion layer in which it is formed into another silver halide emulsion layer, which can result in the formation of unwanted dyes at undesired places. For instance, while being generated in the green sensitive layer and forming a magenta dye through a coupling reaction with the incorporated magenta coupler, the oxidised developer can also diffuse to the red sensitive layer thereby producing unwanted cyan dye or to the blue sensitive layer thereby producing unwanted yellow dye. This kind of colour formation in the wrong layers will damage the colour balance of the photographic image and thus result in poor colour reproduction. One way of circumventing this problem is to incorporate oxidised developer scavengers in interlayers between the light sensitive silver halide emulsion layers. These scavengers should have additional properties such as low tendency to migrate, good stability towards aerial oxidation and high solublity in photographic oils.
Several classes of compounds that are useful as scavengers for oxidised developers are known in literature, e. g. specific derivatives of hydroquinone (EP-A-560198), or compounds of the classes sulphonamidophenol, gallic acid, resorcinol, catechol, aminophenol or aminonaphthol ; or natural antioxidants such as vitamin E or vitamin C.
Some compounds of the class benzofuran-2-one are described in US-4611016 or US5814692 and publications cited therein. Photographic material containing a certain type of benzofuran-2-one is mentioned in US-3615521 (use as precursor of photographic developing agent) and in US-4366240 (hydroxy substituted compounds as electron donor precursors for reducible colour providing compounds). EP-A-871066 mentions the use of a symmetrically substituted 3- (2-hydroxyphenyl)-benzofuran-2-one in the interlayer of a colour photographic material.
It has now been found that certain compounds of the 3-aryl-benzofuran-2-one class are especially useful as additives to photographic material. They are effective in a number of applications and find utility, for example, as scavengers for the oxidised developer (also termed hereafter Dox scavengers), as dye stabilisera, as antioxidants or as antifoggants.
Liquid compounds of the below formula I can also be used as a photographic oil. These compounds are especially stable towards aerial oxidation, diffusion fast and also exhibit a good solubility in high boiling photographic oils. They are well suited for use in photographic elements containing pyrazolotriazole couplers as magenta dye providing compounds, since they are harmless to the light fastness of magenta images obtained from such pyrazolotriazole couplers.
This invention pertains to a compound of the formula V or VI
wherein
R4 is- (CH2) s-COR'1g or-CH (CH3)-COR15 or -CtH2t-COR15, wherein CtH2t is a straight chain or branched alkylene moiety ; or R4 is -O-("CvH2v)-COR15; -O-(CH2) q-OR32;
-OCH2-CH (OH)-CH2-R, 5 ; or-OCH2-CH (OH)-CH2-OR32 ; R'7 is C1-C4alkyl and R'8 is hydrogen or Ci4alkyl ;
R, 5 is hydroxy ;-o'- -M ; Ci-C2oalkoxy ; C3-C2oalkoxy interrupted by 0 and/or roxy ; I-0 r
substituted by a radical selected from OH, phenoxy, C7-C5a) ky) phenoxy, Cy
R24 C, salkoxyphenoxy ; or R,g is Cs-Ci2cycloalkoxy ; C7-Cphenylalkoxy ; phenoxy ;-N ; R25 R25
or a group of formula Tilla or Ifb ; R'15 is C3-C20alkoxy interrupted by 0 and/or substituted by a radical selected from OH, phenoxy, CT-Cisafkytphenoxy, C7-C1salkoxyphenoxy ; or R15 is Cs-Ccyctoatkoxy ; C7 C17phenylalkoxy ; phenoxy; or a group of formula Ila or Iflb ;
R32 is C1-C18-alkanoyl ; Ci-Cgaikanoy) substituted by phenyl or C7-Ci5alkylphenyl ; C3 C18alkenoyl ; cyclohexylcarbonyl ; or naphthylcarbonyl ;
L is a linking group of valency (k+1) and
L is as a divalent group -O-; Q-C2-C12alkylene-Q; -O-CH2(OH)-CH2-O-; -Q-C2-C12alkylene-Q-CO-CvH2v-O-; -O-C2-C12alkylene-O-CH2-CH(OH)-CH2-O-; Q-interrupted
Q-C4-C12alkylene-Q ; Q-phenylene-Q or Q-phenylene-D-phenylene-Q with D being Ci- C4alkylene, O, S, SO or S02 ;
L as a trivalent group is Q-capped C3-C12 alkenetriyl, a trivalent residue of a hexose or a hexitol, or a group (-O-CH2)3C-CH2OH; -Q-CaH2a-N(CbH2b-Q-)-CcH2c-Q-;
- Q-C3-C12alkanetriyl (-Q-CO-CvH2v-O-) 2 ; - 0-C3-C12alkanetriyl (-O-CH2-CH (OH)-CH2-O-) 2 ; and L as a tetravalent group is a tetravalent residue of a hexose or a hexitol ; - Q-C4-C12alkanetetryl (-Q-CO-CvH2v-O-) 3 ; - 0-C4-C12alkanetetryl (-0-CH2-CH (OH)-CH2-O-) 3 ; Q-capped C4-C12alkanetetryl ; a group
v is 1,2, 3,4, 5,6, 7 or 8, preferably 1 or 2;
Q is oxygen or-NH-,
Z is a linking group of valency (k+1) and is as a divalent group C2-C12alkylene, Q-interrupted
C4-C12alkylene, phenylene or phenylene-D-phenylene with D being Ci4alkylene, 0, S, SO or 802 ; Z as a trivalent group is C3-Calkanetriyi, a trivalent residue of a hexose or a hexitol, a group (-CH2) aC-CH20H, or a group-CaH2a-N (CbH2b-)-CcH2c. ; and
Z as a tetravalent group is a tetravalent residue of a hexose or a hexitol, C4-C12alkanetetryl,
a, b, c and k independently are 1,2 or 3, m is 0 or a number from the range 1-12, preferably 1-6, s is 1 or 2, and t is a number from the range 3-12, preferably 3-6; and all other residues are as defined for formula I if n is 1.
Preferred are compounds of formula V, wherein R3 and R5 are Hand R2 is C1-C8alkyl, especially tert. butyl or tert. pentyl. Where Rig or R'15 contains a group of formula ilia or Illb (di-, tri-or tetrameric benzofuranones of formula V), those compounds having symmetrical linking moieties are preferred.
Preferred compounds of the formula V) are those wherein R'7 is methyl or isopropyl and R'8 is hydrogen or methyl.
Compounds of the formulae V and VI are useful as stabilisers for organic material against degradation by light, oxygen and/or heat. Application of these compounds and methods of stabilising are generally as described in GB-A-2322861; examples for organic material which can be stabilized are listed, for example, in GB-A-2319523 from page 15, line 11, until page 20, line 25; possible costabilizers are as listed, for example, in GB-A-2319523 from page 21, line 16, until page 32, bottom line. Examples for organic materials which can be stabilized as well as methods of stabilization are also listed in US-5668200, from column 8, line 18, to column 11, line 25, and from column 18, line 29, to column 22, line 53, and additionally in column 25, lines 29-67; possible costabilizers and their dosage are as listed in US-5668200, column 11, line 51, to column 18, line 28, and column 22, line 54, to column 25, line 28, and in column 26, lines 9-15; these passages of US-5668200 are hereby incorporated by reference. Compounds of the formula V or V) are used for this application preferably in an amount of 0.0005 to 5%, especially 0.01 to 1%, based on the weight of the organic material to be stabilised. The invention also pertains to a composition comprising (a) an organic material which may be subject to degradation by light, oxygen and/or heat, and (b) as stabilizer against these harmful effects a compound of the formula V and/or VI. Most preferred organic materials to be stabilized are synthetic organic polymers and organic dyes, especially thermoplastic polymers such as polyolefin, photographic or materials or coating materials.
Halogen is typically chloro, bromo or iodo. Chloro is preferred.
Alkanol of up to 25 carbon atoms is a branched or unbranched radical, typically formyl, ace
tyl, propionyl, butanoyl, pentanoyl, hexanoyl, heptanoyl, octanoyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl, tridecanoyl, tetradecanoyl, pentadecanoyl, hexadecanoyl, heptadecano yl, octadecanoyl, eicosanoyl or docosanoyl. Alkanol of 2 to 18, in particular of 2 to 12, e. g. of 2 to 6, carbon atoms is preferred. Acetyl is particularly preferred. C2-C2sAtkanoyl which is
substituted by a di (Ci-C6alkyl) phosphonate group is typica) ! y (CH3CH20) 2POCH2CO-, (CH30) 2POCHzCO-, (CH3CH2CH2CH20) 2POCH2CO-, (CH3CH20) 2POCH2CH2CO-, (CH30) 2POCH2CH2CO-, (CH3CH2CH2CH20) 2POCH2CH2CO-, (CH3CH20) 2PO (CH2) 4CO-, (CH3CH20) 2PO (CH2) aCO-or (CH3CH20) 2PO (CH2) 17CO-. C3-C2sAlkanoyi which is interrupted
by oxygen, sulfur or N-R14 is typically CH3-O-CH2CO-, CH3-S-CH2CO-,
CH3-NH-CH2CO-, CH3-N (CH3)-CH2CO-, CH3-O-CH2CH2-O-CH2CO-, CH3- (O-CH2CH2-) 20-CH2CO-, CH3- (O-CH2CH2-)aO-CH2CO-or CHsO-CH2CH2-)O-CH2CO-. Alkanoyloxy is oxygen-capped alkanol ; preferences are mainly as can be derived from alkanol above.
Alkenyl of 3 to 25 carbon atoms is a branched or unbranched radical, typically propenoyl, 2butenoyl, 3-butenoyl, isobutenoyl, n-2, 4-pentadienoyl, 3-methyl-2-butenoyl, n-2-octenoyl, n2-dodecenoyl, isododecenoyl, oleoyl, n-2-octadecenoyl or n-4-octadecenoyl. Alkenyl of 3 to 18, preferably of 3 to 12, e. g. of 3 to 6, most preferably of 3 to 4, carbon atoms is preferred.
C3-C2sAikenoyl which is interrupted by oxygen, sulfur or N-R14 is typically
CH3OCH2CH2CH=CHCO-or CH3OCH2CH2OCH=CHCO-.
Alkenoyloxy is oxygen-capped alkenyl ; preferences are mainly as can be derived from alkenyl above.
C6-CgCydoalkylcarbonyl is typically cyclohexylcarbonyl, cycloheptylcarbonyl or cyclooctylcafbony\. Cyclohexylcarbonyl is preferred. Cg-CgCycloalkyicarbonyloxy is oxygen-capped cycloalkylcarbonoyl ; preferences are analogous.
C1-C12Alkyl-substituted benzoyl which preferably carries 1 to 3, more preferably 1 or 2, alkyl groups is typically o-, m-or p-methylbenzoyl, 2, 3-dimethylbenzoyl, 2, 4-dimethylbenzoyl, 2, 5dimethylbenzoyl, 2, 6-dimethylbenzoyl, 3, 4-dimethylbenzoyl, 3,5-dimethylbenzoyl, 2-methyl-6 ethylbenzoyl, 4-tert-butylbenzoyl, 2-ethylbenzoyl, 2,4, 6-trimethylbenzoyl, 2, 6-dimethyl-4-tert- butylbenzoyl or 3, 5-di-tert-butylbenzoyl. Preferred substituents are CrCga ! kyt, in particular
C1-C4alkyl, C1-Ci2Alkyl-substituted benzoyloxy which preferably carries 1 to 3, more preferably 1 or 2,
alkyl groups is typically o-, m-or p-methylbenzoyloxy, 2, 3-dimethylbenzoyloxy, 2, 4-dimethylbenzoyloxy, 2, S-dimethylbenzoyloxy, 2, 6-dimethylbenzoyloxy, 3, 4-dimethylbenzoyloxy, 3, 5dimethylbenzoyloxy, 2-methyl-6-ethylbenzoyloxy, 4-tert-butylbenzoyloxy, 2-ethylbenzoyloxy, 2, 4, 6-trimethylbenzoyloxy, 2, 6-dimethyl-4-tert-butylbenzoyloxy or 3, 5-di-tert-butylbenzoyloxy.
Preferred substituents are Ci-Cgaiky), in particular C1-C4alky\. Alkyl of up to 25 carbon atoms is a branched or unbranched radical, such as methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1methylpentyl, 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-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl or docosyl. One of the preferred meanings of R2 and R4 is, for example, Cl-C, 8alkyl. A particularly preferred meaning of R4 is CrC4alkyL One of R2 and R4 is preferably a branched radical ; especially preferred are both R2 and R4 branched radicals.
Alkenyl of 3 to 25 carbon atoms is a branched or unbranched radical, such as propenyl, 2butenyl, 3-butenyl, isobutenyl, n-2, 4-pentadienyl, 3-methyl-2-butenyl, n-2-octenyl, n-2-dodecenyl, isododecenyl, oleyl, n-2-octadecenyl or n-4-octadecenyl. Alkenyl of 3 to 18, preferably of 3 to 12, e. g. of 3 to 6, in particular of 3 to 4, carbon atoms is preferred.
Alkenyloxy is oxygen capped alkenyl ; preferences are analogous.
Alkynyl of 3 to 25 carbon atoms is a branched or unbranched radical, such as propynyl (-CH2 CECH), 2-butynyl, 3-butynyl, n-2-octynyl, or n-2-dodecynyl. Alkynyl of 3 to 18, preferably of 3 to 12, e. g. of 3 to 6, in particular of 3 to 4 carbon atoms is preferred.
Preferences for alkynyloxy (oxygen capped alkynyl) are analogous.
C2-C25AIkyl which is interrupted by oxygen, sulfur or 1\ N-Rl4 is typically
CH3-O-CH2-, CH3-S-CH2-, CH3-NH-CH2-, CH3-N (CH3)-CH2-, CH3-O-CH2CH2-O-CH2-, CH3- (O-CH2CH2-) 2-0-CH2-, CH3- (O-CH2CH2-) 30-CH2- or CH3- (O-CH2CH2-) 40-CH2-.
C7-CgPhenylalkyl is typically benzyl, a-methylbenzyl, a, a-dimethylbenzyl or 2-phenylethyl.
Benzyl and a, a-dimethylbenzyl are preferred.
C7-CgPhenylalkyl which is unsubstituted or substituted at the phenyl moiety by 1 to 3 Ci-C4- alkyl is typically benzyl, a-methylbenzyl, a, a-dimethylbenzyl, 2-phenylethyl, 2-methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, 2, 4-dimethylbenzyl, 2, 6-dimethylbenzyl or 4-tert-butylbenzyl.
Benzyl is preferred.
Cy-C2sPhenylalkyl which is interrupted by oxygen, sulfur or N-R and which is unsub
stituted or substituted at the phenyl moiety by 1 to 3 C-C4alkyl is a branched or unbranched radical, such as phenoxymethyl, 2-methylphenoxymethyl, 3-methyl-phenoxymethyl, 4-me thylphenoxymethyl, 2, 4-di methylphenoxym ethyl, 2, 3-dimethylphenoxymethyl, phenylthiome- thy !, N-methyl-N-phenyl-methyl, N-ethyl-N-phenylmethyl, 4-tert-butylphenoxymethyl, 4-tert butylphenoxyethoxymethyl, 2, 4-di-tert-butylphenoxymethyl, 2, 4-di-tert-butylphenoxyethoxymethyl, phenoxyethoxyethoxyethoxymethyl, benzyloxymethyl, benzyloxyethoxymethyl, N
benzyl-N-ethylmethyl or N-benzyl-N-isopropylmethyl.
C7-C9Phenylalkoxy is typically benzyloxy, a-methylbenzyloxy, a, a-dimethylbenzyloxy or 2 phenylethoxy. Benzyloxy is preferred.
C1-C4Alkyl-substituted phenyl which preferably contains 1 to 3, in particular 1 or 2, alkyl groups is typically o-, m-or p-methylphenyl, 2, 3-dimethylphenyl, 2, 4-dimethylphenyl, 2,5-dimethylphenyl, 2, 6-dimethylphenyl, 3, 4-dimethylphenyl, 3, 5-dimethylphenyl, 2-methyl-6-ethyl- phenyl, 4-tert-butylphenyl, 2-ethylphenyl or 2, 6-diethylphenyl.
CrC4Alkyl-substituted phenoxy which preferably contains 1 to 3, in particular 1 or 2, alkyl
groups is typically o-, m-or p-methylphenoxy, 2, 3-dimethylphenoxy, 2, 4-dimethylphenoxy, 2, 5-dimethylphenoxy, 2, 6-dimethylphenoxy, 3, 4-dimethylphenoxy, 3, 5-dimethylphenoxy, 2methyl-6-ethylphenoxy, 4-tert-butylphenoxy, 2-ethylphenoxy or 2, 6-diethytphenoxy.
Unsubstituted or C1-C4alkyl-substituted Cs-Cgcycloalkyl is, for example, cyclopentyl, methyl cyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethyl- cyclohexyl, tert-butylcyclohexyl, cycloheptyl or cyclooctyl. Cyclohexyl and tert-butylcyclohexyl are preferred.
Unsubstituted or C1-C4alkyl-substituted C5-C8cycloalkoxy is, for example, cyclopentoxy, me
thylcyclopentoxy, dimethylcyclopentoxy, cyclohexoxy, methylcyclohexoxy, dimethylcyclohex oxy, trimethylcyclohexoxy, tert-butylcyclohexoxy, cycloheptoxy or cyclooctoxy. Cyclohexoxy and tert-butylcyclohexoxy are preferred.
Alkoxy of up to 25 carbon atoms is a branched or unbranched radical, such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, tetradecyloxy, hexadecyloxy or octadecyloxy. Alkoxy of 1 to 12, in particular of 1 to 8, e. g. of 1 to 6, carbon atoms is preferred.
Cs-CzsAikoxy which is interrupted by oxygen, sulfur or N-R14 is typically
CH3-O-CH2CH2O-, CH3-S-CH2CH2O-, CH3-NH-CH2CH2O-, CH3-N (CH3)-CH2CH20-, CH3-0-CH2CH2-0-CH2CH20-, CH3- (O-CH2CH2-) 20-CH2CH20-, CH3- (0-CH2CH2-) 30-CH2CH20-or CH3- (O-CH2CH2-) 40-CH2CH20-.
Alkylthio of up to 25 carbon atoms is a branched or unbranched radical, such as methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, pentylthio, isopentylthio, hexylthio, heptylthio, octylthio, decylthio, tetradecylthio, hexadecylthio or octadecylthio. Alkylthio of 1 to 12, in particular of 1 to 8, e. g. of 1 to 6 carbon atoms is preferred.
Alkylamino of up to 4 carbon atoms is a branched or unbranched radical, such as methyl amino, ethylamino, propylamino, isopropylamino, n-butylamino, isobutylamino or tert-butyl- amino.
Di (C1-C4alkyl) amino also means that the two radicals are independently of the other bran
ched or unbranched, such as dimethylamin, methylethylamino, diethylamino, methyl-n-propylamino, methylisopropylamino, methyl-n-butylamino, methylisobutylamino, ethylisopropylamino, ethyl-n-butylamino, ethylisobutylamino, ethyl-tert-butylamino, diethylamino, diisopro pylamino, isopropyl-n-butylamino, isopropylisobutylamino, di-n-butylamino or di-isobutyl- amino.
Alkanoylamino of up to 25 carbon atoms is a branched or unbranched radical, such as formylamino, acetylamino, propionylamino, butanoylamino, pentanoylamino, hexanoylamino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino, undecanoylamino, dodecanoylamino, tridecanoylamino, tetradecanoylamino, pentadecanoylamino, hexadecanoylamino, heptadecanoylamino, octadecanoyamino, eicosanoylamino or docsanoylamino.
Alkanoylamino of 2 to 18, in particular of 2 to 12, e. g. of 2 to 6, carbon atoms is preferred.
C1-ClsAlkylene is a branched or unbranched radical, such as methylene, ethylene, propy lene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octa
methylene, decamethylene, dodecamethylene or octadecamethylene. C1-Ci2Alkylene and, in particular, Ci-Csalkylene are preferred.
A C1-C4Alkyl-substituted C5-C12cycloalkylene ring which preferably contains 1 to 3, in particular 1 or 2, branched or unbranched alkyl groups is typically cyclopentylene, methylcyclo- pentylene, dimethylcyclopentylene, cyclohexylene, methylcyclohexylene, dimethylcyclohexy-
lene, trimethylcyclohexylene, tert-butylcyclohexylene, cycloheptylene, cyclooctylene or cyclodecylene. Cyclohexylen and tert-butylcyclohexylene are preferred.
C2-CisAlkylene which is interrupted by oxygen, sulfur or N-R is, for example,
- CH2-0-CH2-,-CH2-S-CH2-,-CH2-NH-CH2-,-CH2-N (CH3)-CH2-,-CH2-O-CH2CH2-O-CH2-, -CH2- (O-CH2CH2-) 20-CH2-,-CH2- (O-CH2CH2-) 30-CH2-,-CH2- (O-CH2CH2-) 40-CH2- or - Cn2Cn2-S-Cn2Cn2''' C2-C18Alkenylene is typically vinylene, methylvinylene, octenylethylene or dodecenylethylene.
C2-CaAlkenylene is preferred.
Alkylidene of 2 to 20 carbon atoms is, for example, ethylidene, propylidene, butylidene, pentylidene, 4-methylpentylidene, heptylidene, nonylidene, tridecylidene, nonadecylidene, 1-methylethylidene, 1-ethylpropylidene or 1-ethylpentylidene. C2-C8Alkylidene is preferred.
Phenylalkylidene of 7 to 20 carbon atoms is typically benzylidene, 2-ph enyl ethyl iden e or 1 phenyl-2-hexylidene. C7-CgPhenylalkylidene is preferred.
C5-C8Cycloalkylene is a saturated hydrocarbon group having two free valencies and at least one ring unit and is typically cyclopentylene, cyclohexylene, cycloheptylene or cyclooctylene.
Cyclohexylene is preferred.
C7-C8Bicycloalkylene is typically bicycloheptylene or bicyclooctylene.
Unsubstituted or C1-C4alkyl-substituted phenylene or naphthylene is typically 1,2-, 1,3-, 1,4phenylene, 1,2-, 1,3-, 1,4-, 1,6-, 1,7-, 2, 6- 2, 7-naphthylene. 1, 4-Phenylene is preferred.
A Ci-C4alkyl-substituted C5-C8cycloalkylidene ring which preferably contains 1 to 3, in parti cular 1 or 2, branched or unbranched alkyl groups is typically cyclopentylidene, methylcyclo
pentylidene, dimethylcyclopentylidene, cyclohexylidene, methylcyclohexylidene, dimethylcyclohexylidene, trimethyfcyclohexylidene, tert-butylcyclohexylidene, cycloheptylidene or cyclooctylidene. Cyclohexyliden and tert-butylcyclohexylidene are preferred.
A mono-, di-or tri-valent metal cation is preferably an alkali metal cation, alkaline earth metal cation or aluminium cation, typically Na+, K+, Mg++, Ca++ or Al+++.
Compounds of the formula V and V) can be obtained in analogy to methods known in the art, e. g. as described in US-5814692 or publications cited therein.
Examples for compounds of the formula V or VI of the invention are :
Compound 19 :
Compound 20 :
Compound 22 :
Compound 23 a) :
Compound 26 a) :
Compound 29 :
Compound 30 :
Compound 31 :
Compound 32 :
These products may additionally contain minor amounts of other structural isomers in accordance with the substitution at the phenyl ring in 3-position of the benzofuran-2-one.
The synthetic methods used for the preparation of the benzofuran-2-ones shown above are described e. g. in US Patents Nos. 5,607, 624 and 5,814, 692. Examples for the synthesis of some new compounds among the above are given below from example 8 onwards.
Percentages given in the following examples are by weight if not otherwise indicated. Room temperature denotes a temperature in the range 20-25OC.
Frequent abbreviations used are:
TCP tricresyl phosphate;
RH relative humidity; m. p. melting point or range;
NMR nuclear magnetic resonance of'H.
Synthesis of new compounds
Example 8: 5, 7-Di-tert-pentyl-3 (4-isopropylphenyl)-3H-benzofuran-2-one (compound No. 26) a) 2, 6-Di-tert-pentylphenol (161.4 g), glyoxylic acid (122.3 g of the 50% b. w. solution in water) and 1.3 g of p-toluene sulphonic acid are heated in 500 ml of ethylenechloride under nitrogen at reflux temperature in an apparatus designed for the removal of water.
After 3.5 hours the reaction mixture is cooled to room temperature, washed 3 times with
25 mi water, dried over magnesium sulphite and evaporated under reduced pressure to give 214.3 g of: 5, 7-di-tert-pentyl-3-hydroxy-3H-benzofuran-2-one as an orange coloured oil. b) 29.6 g of the product obtained under (a) are heated together with cumane (150 mi) and an acid earth catalyst (Fulcat 22 B, supplied by Laport, GB) under nitrogen to reflux.
After 2 hours, the reaction mixture is filtered hot. Evaporation of the filtrate gives 35.1 g of raw product, which is subjected to chromatography on silica gel using hexane/ethyl acetate (4: 1) as eluant. 26.7 g of the title product (compound No. 26) are obtained as an orange coloured oil. NMR (CDCI3) 3-H: 5.29 ppm.
Example 9: Preparation of 7-isopropyl-5- (4-methoxycarbonyl-1, 1-dimethylbutyl)-3, 4 dimethylphenyl-3H-benzofuran-2-one (compound No. 23) a) 5-Methyl-5- (4-hydroxy-3-isopropyl phenyl)-hexanoic acid methyl ester (10. 0 g), glyoxylic acid (6.4 g of the 50 % solution in water) and p-toluene sulphonic acid (40 mg) are heated in 40 ml of ethylene chloride under nitrogen at reflux in an apparatus designed for the removal of water. After 5 hours the reaction mixture is cooled to room temperature,
washed two times with 25 ml water, dried over magnesium sulphate and evaporated under reduced pressure to give 13 g of 7-isopropyl-5- (4-methoxycarbonyl-1, 1 dimethylbutyl)-3-hydroxy-3H-benzofuran-2-one as a yellow oil. b) 13 g of the above product (a), o-xylene (50 ml) are heated together with an acid earth catalyst (see example 8b) under nitrogen at reflux for 2.5 hours. The reaction mixture is filtered hot and the filtrate evaporated to give 16.6 g of a yellow oil. This is chromatographed over silica gel using hexane/ethylacetate 20: 5 as eluant. 10.4 g of the
mixture of the 2 isomers 7-isopropyl-5- (4-methoxycarbonyl-1, 1-dimethylbutyl)-3, 4dimethytphenyl-3H-benzofuran-2-one and 7-isopropyl-5- (4-methoxycarbonyl-1, 1 dimethylbutyl)-3- (2, 3-dimethylphenyl)-3H-benzofuran-2-one as a slightly brown resin is obtained. NMR (CDCI3) 3-H: 4.80 ppm.
Example 10 : Preparation of 7-lsopropyl-5- (4-methoxycarbonyl-1, 1-dimethylbutyl)-3- (2. 5-dimethylphenyl)-3H-benzofuran-2-one (compound No. 22) The product obtained in example 9a (14.35 g), p-xylene (50 ml) and an acid earth catalyst (see example 8b) are treated as described in example 9b to give 9.52 g of the title product (compound No. 22) as a slightly orange resin. NMR (CDCI3) 3-H: 5.05 ppm.
Example 11: Preparation of compound No. 19 a) 3- (7-. tert.-Butyl-2-oxo-3-phenyl-2, 3-dihydro-benzofuran-5-yl)-propionic acid
122.3 g (0.55 mol) 3- (3-tert.-butyl-4-hydroxy-phenyl)-propionic acid (CAS Nr. 107551-67
7) and 92.1 g (0.61 mol) mandelic acid are melted together and then stirred under nitrogen at 200 Oc during 4 h. The mixture is then cooled to room temperature, dissolved in toluene and chromatographed on silica gel with dichloromethane-ethyl acetate (3: 1) to afford 103 g of the title compound as a pale yellow resin. 1H-NMR (100 MHz, CDCts) : 7.4
6.9 m (7 ArH), 4.83 s (1 H), 3.00-2. 54 m (4H), 1.42 s (t-Bu).
23.7 b) 23.7 g (0.07 mol) of the product from example 11 a, 4.2 g (0.035 mol) 1, 6-hexanediol and 0.3 g p-toluene sus phonic acid are refluxed in 250 ml of xylene under Dean-Stark water separator during 6 h. The mixture is then cooled to room temperature, washed with water, dried with MgSO4 and evaporated under vacuum. Chromatography of the residue on silica gel with dichloromethane-hexane (19: 1) affords the 14.8 g of the compound No.
19 as a pale yellow oil.'H-NMR (100 MHz, CDCb) : 7.4-6. 9 m (14 ArH), 4.82 s (2H), 4.08
3.96 m (4H), 2.98-2. 51 m (8H), 1.61-1. 26 m (4H), 1.42 s (t-Bu).
Example 12: Preparation of 7-tert. butyl-5- (2-methoxycarbonylethyl)-3- (2, 5-dimethyiphenyl)- 3H-benzofuran-2-one (compound No. 24) a) 3- (4-hydroxy-3-tert. butylphenyl) propionic acid methyl ester (10.0 g), glyoxylic acid (7.4 g of the 50 % solution in water) and p-toluene sulphonic acid (40 mg) are heated in 40 mi ethylene chloride under nitrogen at reflux for 3 hours distilling off all water present and formed during the reaction. The reaction mixture is washed with water, dried over magnesium sulphate and evaporated under reduced pressure to give 13.0 g of 7 tert. butyl-5- (2-methoxycarbonylethyl)-3-hydroxy-3H-benzofuran-2-one. b) b) 13 g of the product from the above example 12a, 50 ml of p-xylene and and an acid earth catalyst (see example 8b) are heated under nitrogen at reflux for 2.5 hours. The reaction mixture is filtered hot and the filtrate evaporated under reduced pressure to give
17.0 g of an orange oil. This is purified by column chromatography over 350 g silica gel using hexane/ethylacetate 4: 1 as eluant to give the title product, which solidifies after two days. Recrystallization from hexane gives a colourless solid, mp 800. NMR (CDCI3) 3
H: 4.98 ppm.
Example 13: Preparation of compound No. 29 a) 2.40 g 2- (3-tert. Butyl-4-hydroxyphenoxy)-acetic acid methyl ester is heated 8hrs. in 100ml toluene at reflux with 0.34g pentaerythritol in the pesence of 0. 1 g p toluenesulphonic acid. The resulting methanol is distilled off using a Hickmann apparatus.
The reaction mixture is cooled to room teperature, washed with water, dried over magnesium sulphate and evaporated under reduced pressure. The residue (2,24g) is treated with glyoxylic acid (1.62g of the 50% solution in water) and p. toluene sulphonic acid (0. 1 g) and heated in 20ml. ethylene chloride under nitrogen at reflux for 3.5hrs., distilling off all water present and formed during the reaction. The reaction mixture is washed wth water, dried over magnesium sulphate and evaporated under reduced pressure to give 2.80g of compound X of the formula :
b) 2. 8g Of the above compound X, 25mi. of cymene and an acid earth catalyst (see example
8b) are heated under nitrogen at reflux for 4hrs. The reaction mixture is filtered hot and the filtrate evaporated under reduced pressure to give 3.50g of impure product. This is purified by column chromatography over 160g silica gel using hexane/ethyl acetate 4: 1 as eluant to give purified compound No. 29 as a colourless resin.
Example 14 : Preparation of compound No. 30 a) 3. 50g 2- (3-tert-Butyl-4-hydroxyphenoxy)-propionic acid octyl ester is heated 3hrs. under nitrogen with glyoxylic acid (1. 62g of the 50% solution in water) and p-toluene sulphonic acid (0. 1 g) in 20ml ethylene chloride at reflux, distilling off the water present and formed during the reaction. The reaction mixture is washed with water, dried over magnesium sulphate and evaporated under reduced pressure to give 4. 05g of the below intermediate Xil as a colouriess oil :
b) 4. 05g of the above intermediate XII, 25mLcymene and an acid catalyst (see example 8b) are heated under nitrogen at reflux for 3 hrs. The reaction mixture is filtered hot and the filtrate evaporated under reduced pressure to give 4. 91 g of the title product X ! H. This is purified by column chromatography using 150g silica gel and hexane/ethyl acetate 4: 1 as eluant to give purified compound No. 30 as a colourless oil.
Example 15: Preparation of compound No. 31 a) 3.00g 1-Butoxy-2-hydroxy-3- (3-tert. butyl-4-hydroxyphenoxy)-propane is treated with glyoxylic acid (1. 62g of a 50% solution in water) and p-toluene sulphonic acid (0. 1 g) and heated in 20ml ethylene chloride under nitrogen at reflux for 2.5 hrs. , distilling off all the water present and formed during the reaction. The reaction mixture is washed with water, dried over magnesium sulphate and evaporated under reduced pressure to give 3.62 g of crude intermediate XIV :
b) This was heated under nitrogen with an acid catalyst (see example 8b) in 25ml refluxing tert. butylbenzene for 2.5hrs. The reaction mixture is filtered hot and the filtrate evaporated under reduced pressure. The residue is purified by column chromatography over 150g silica gel using hexane/ethylacetate 4: 1 as eluant to give compound No. 31 as a colourless oil.
Example 16: Preparation of compound No. 32
Proceeding as in example 15, but using 2. 92g of compound XVI of formula
in step (a) instead of 1-butoxy-2-hydroxy-3- (3-tert. butyl-4-hydroxyphenoxy)-propane one obtains compound No. 32 as a slightly yellow resin.
Claims (2)
1 to 3 C1-C4alkyl ; or R20 and R21, together with the linking carbon atoms, form a C5-C12cycloalkylene ring which is unsubstituted or substituted by 1 to 3 C1-C4alkyl ; R14 is hydrogen or Ci-C8alkyl ; R22 is hydrogen or Ci-C4alkyl ; R23 is hydrogen ; C1-C25alkanoyl ; C3-C25alkenoyl ; C3-C25alkanoyl which is interrupted
by oxygen, sulphur or N-R14 ; C2-C25alkanoyl which is substituted by a 14 1
di (Ci-C6alkyl) phosphonate group ; Ce-Cgcydoatkytcarbonyt ; thenoyl ; furoyl ;
benzoyl or C1-C12alkyl-substituted benzoyl ;
with
R26 is hydrogen or C1-C4alkyl ;
R27 is a direct bond; C1-C18alkylene ; C2-C18alkylene which is interrupted by oxygen,
sulphur or'N-R14 ; C2-C18alkenylene ; C2-C20alkylidene ; C7-C20phenyl
alkyliden ; Cs-Cacycloalkylene ; C7-C8bicycloalkylene ; unsubstituted or
C1-C4alkyl-substituted phenylene ; or \ ; o s
R24 R28 ishydroxy,-o'-'-M). Ci-dsatkoxyor-N ; with R24 and R25 are 25
each independently of the other H orCl-Cl8alkyl, R29 is oxygen or-NH- ; R30 is C1-C18alkyl or phenyl ; especially wherein at least 2 of the residues R7, Ra, Rg, Rio. R11 are H;
R'7 is C1-C4alkyl and R'8 is hydrogen or C1-C4alkyl ;
R15 is hydroxy, o'-L M, with M is an r-valent metal cation ; r is 1, 2 or 3 ; and I-r +1 1
C3-C20alkoxy interrupted by 0 and/or substituted by a radical selected from OH, phenoxy, Cy-Cisatkytphenoxy, C7-C15alkoxyphenoxy ; or
R24 R15 is C5-Ci2cyc) oa ! koxy ; Cy-Ci/phenytatkoxy ; phenoxy ;-nez ; with R24 and R25 R25
R25 independently are H or Cl-Clsalkyl ; or R15 is a group offormula Hlb ;
(filb) ; with Ri is a radical of formula 11
(il), wherein R7-11 is as defined above,
R'15 is C3-C2oalkoxy interrupted by 0 and/or substituted by a radical selected from OH, phenoxy, C7-C15alkylphenoxy, C7-Ci5alkoxyphenoxy ; or R'15 is C5-Ci2cydoatkoxy ; Cy-Ci/phenyiatkoxy ; phenoxy ; or a group of formula Ilia or Illb ; R32 is Ci-Cigatkanoy) ; C1-C8alkanoyl substituted by phenyl or C7-Ci5alkylphenyl ; C3-Ci8alkenoyl ; cyclohexylcarbonyl ; or naphthylcarbonyl ; L is a linking group of valency (k+1) and is, as a divalent group, - 0- ; Q-C2-C12alkylene-Q ; - 0-CH2-CH (OH)-CH2-0- ;
- Q-C2-C12alkylene-Q-CO-CvH2v-0- ; - 0-C2-Ci2alkylene-O-CH2-CH (OH)-CH2-0- ; Q-interrupted Q-C4-C12alkylene-Q ; Q-phenylene-Q or Q-phenylene-D-phenylene-Q with D being C1-C4alkylene, 0, S, SO or S02 ; L as a trivalent group, is Q-capped C3-C12alkanetriyl, a trivalent residue of a hexose or a hexitol, or a group (-0-CH2) 3C-CH20H ; - Q-CaH2a-N (CbH2b-Q-)-CcH2c-Q- ; - Q-C3-C12alkanetriyl (-Q-CO-CvH2v-0-) 2 ; - 0-C3-Ci2a) kanetriy) (-0-CH2-CH (OH)-CH2-0-) 2 ; and L as a tetravalent group, is a tetravalent residue of a hexose or a hexitol ; - Q-C4-C12alkanetetryl (-Q-CO-CvH2v-0-) 3 ; - 0-C4-C12alkanetetryl (-0-CH2-CH (OH)-CH2-0-) 3 ; Q-capped C4-C12alkanetetryl ;
Q is oxygen or-NH-,
2. Process for stabilizing an organic material against deterioration by light, oxygen and/or heat, which process comprises incorporating a compound of the formula V and/or VI according to claim 1 as stabilizer into said organic material.
2 is a linking group of valency (k+1) and is as a divalent group C-Calkylene, Qinterrupted C4-C4a ! kylene, phenylene or phenylene D-phenylene with D being 64
C4alkylene, 0, S, SO or SC) 2 ; Z, as a trivalent group, is Cs-Calkanetriyl, a trivalent residue of a hexose or a cw. hexite', a grgup (-..., 20 C o r a g Fe u p Z, as a tetravalent group, is a tetravalent residue of a hexose or a hexitol, C4s ICH2 H2 H2 H2 H2 CH, H2 H2 H2 H2 alkanetetryl, a 9. oF a group
a, b, c and k independently are 1, 2 or 3,
m is 0 or a number from the range 1 12, w yU q is 1,2, 3,4, 5 or 6; s is 1 or 2, and t is a number from the range 3-12, v is 1,2, 3,4, 5, 6, 7 or 8.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98811035 | 1998-10-19 | ||
| EP99810514 | 1999-06-11 | ||
| EP99810612 | 1999-07-09 | ||
| GB9923655A GB2343007B (en) | 1998-10-19 | 1999-10-07 | Colour photographic material |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB0105372D0 GB0105372D0 (en) | 2001-04-18 |
| GB2368063A true GB2368063A (en) | 2002-04-24 |
| GB2368063B GB2368063B (en) | 2002-12-11 |
Family
ID=27443756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0105372A Expired - Fee Related GB2368063B (en) | 1998-10-19 | 1999-10-07 | Colour photographic material |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2368063B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2042562A (en) * | 1979-02-05 | 1980-09-24 | Sandoz Ltd | Stabilising polymers |
-
1999
- 1999-10-07 GB GB0105372A patent/GB2368063B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2042562A (en) * | 1979-02-05 | 1980-09-24 | Sandoz Ltd | Stabilising polymers |
| US4611016A (en) * | 1979-02-05 | 1986-09-09 | Ciba-Geigy Corp. | Benzofuranone or indolinone compounds useful as stabilizers for organic materials |
Non-Patent Citations (1)
| Title |
|---|
| Indian J. Chem., Sect. B, 1980, Vol. 19B(10), pages 891-893 * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2368063B (en) | 2002-12-11 |
| GB0105372D0 (en) | 2001-04-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL194760C (en) | 3-Arylbenzo [b] furan-2-ones and organic materials stabilized with these furanones. | |
| JP3505604B2 (en) | 3- (2-acyloxyethoxyphenyl) benzofuran-2-one for use as a stabilizer | |
| JP3603231B2 (en) | Method for producing 3-arylbenzofuranones | |
| JP3793950B2 (en) | Benzofuran-2-one as a stabilizer | |
| US6417358B1 (en) | Process for the preparation of 3-aryl-benzofuranones | |
| KR100561327B1 (en) | A process for preventing the migration of the oxidised developer in a colour photographic material | |
| GB2368063A (en) | 3-Aryl-5-substituted-3H-benzofuran-2-one derivatives and their use as stabilizers of organic material against degradation by light, oxygen or heat |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20061007 |