NL9300865A - 3-(carboxymethoxyfenyl)-benzofuran-2-on derivaten als stabilisatoren. - Google Patents

3-(carboxymethoxyfenyl)-benzofuran-2-on derivaten als stabilisatoren. Download PDF

Info

Publication number: NL9300865A
Authority: NL; Netherlands
Prior art keywords: alkyl; hydrogen; alkoxy; formula; tert
Prior art date: 1992-05-22

Application number

NL9300865A

Other languages

English (en)

Dutch (nl)

Original Assignee

Ciba Geigy

Priority date (The priority date 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 date listed.)

1992-05-22

Filing date

1993-05-18

Publication date

1993-12-16

1993-05-18 Application filed by Ciba Geigy filed Critical Ciba Geigy

1993-12-16 Publication of NL9300865A publication Critical patent/NL9300865A/nl

Links

239000003381 stabilizer Substances 0.000 title claims description 14
BUPAPANYJUHHIE-UHFFFAOYSA-N 2-[2-(2-oxo-3h-1-benzofuran-3-yl)phenoxy]acetic acid Chemical class OC(=O)COC1=CC=CC=C1C1C2=CC=CC=C2OC1=O BUPAPANYJUHHIE-UHFFFAOYSA-N 0.000 title description 4
-1 cyclohexylidene ring Chemical group 0.000 claims description 157
239000001257 hydrogen Substances 0.000 claims description 108
229910052739 hydrogen Inorganic materials 0.000 claims description 108
125000000217 alkyl group Chemical group 0.000 claims description 82
150000001875 compounds Chemical class 0.000 claims description 67
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 60
239000000203 mixture Substances 0.000 claims description 47
125000003545 alkoxy group Chemical group 0.000 claims description 44
150000002431 hydrogen Chemical class 0.000 claims description 42
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 23
150000001335 aliphatic alkanes Chemical class 0.000 claims description 21
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
239000001301 oxygen Substances 0.000 claims description 16
229910052760 oxygen Inorganic materials 0.000 claims description 16
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 16
239000011593 sulfur Substances 0.000 claims description 16
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 12
229910052751 metal Inorganic materials 0.000 claims description 12
239000011368 organic material Substances 0.000 claims description 12
239000002184 metal Substances 0.000 claims description 11
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
125000004423 acyloxy group Chemical group 0.000 claims description 8
230000015556 catabolic process Effects 0.000 claims description 8
241000546339 Trioxys Species 0.000 claims description 7
238000006731 degradation reaction Methods 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
230000001590 oxidative effect Effects 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 6
125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 5
230000000087 stabilizing effect Effects 0.000 claims description 5
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 4
125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 4
125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 4
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 3
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
229920001059 synthetic polymer Polymers 0.000 claims 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 claims 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 31
229920001577 copolymer Polymers 0.000 description 30
229920000642 polymer Polymers 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 15
150000002148 esters Chemical class 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000004743 Polypropylene Substances 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
0 CC1C(C2)C2*CC1 Chemical compound CC1C(C2)C2*CC1 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
239000004952 Polyamide Substances 0.000 description 10
239000002253 acid Substances 0.000 description 10
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 10
229920002647 polyamide Polymers 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 9
229920001684 low density polyethylene Polymers 0.000 description 9
239000004702 low-density polyethylene Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000005062 Polybutadiene Substances 0.000 description 8
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 8
229920002857 polybutadiene Polymers 0.000 description 8
229920001155 polypropylene Polymers 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
ISWSIWMERMANOR-UHFFFAOYSA-N 2-[4-(carboxymethoxy)phenyl]-2-hydroxyacetic acid Chemical class OC(=O)C(O)C1=CC=C(OCC(O)=O)C=C1 ISWSIWMERMANOR-UHFFFAOYSA-N 0.000 description 7
239000004698 Polyethylene Substances 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
229920000573 polyethylene Polymers 0.000 description 7
229920000098 polyolefin Polymers 0.000 description 7
229920006324 polyoxymethylene Polymers 0.000 description 7
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
239000000654 additive Substances 0.000 description 6
KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000000463 material Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000004417 polycarbonate Substances 0.000 description 6
229920000915 polyvinyl chloride Polymers 0.000 description 6
239000004800 polyvinyl chloride Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
229920002943 EPDM rubber Polymers 0.000 description 5
229920000877 Melamine resin Polymers 0.000 description 5
239000004721 Polyphenylene oxide Substances 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
150000001993 dienes Chemical class 0.000 description 5
ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 5
229920001903 high density polyethylene Polymers 0.000 description 5
239000004700 high-density polyethylene Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
229920000728 polyester Polymers 0.000 description 5
239000002904 solvent Substances 0.000 description 5
150000005846 sugar alcohols Polymers 0.000 description 5
ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
150000001252 acrylic acid derivatives Chemical class 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
239000011575 calcium Substances 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
229920001971 elastomer Polymers 0.000 description 4
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
239000000155 melt Substances 0.000 description 4
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
150000002815 nickel Chemical class 0.000 description 4
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
229920000570 polyether Polymers 0.000 description 4
229920006380 polyphenylene oxide Polymers 0.000 description 4
239000004814 polyurethane Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
230000006641 stabilisation Effects 0.000 description 4
238000011105 stabilization Methods 0.000 description 4
229920001169 thermoplastic Polymers 0.000 description 4
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 3
IEUQSYIPXJRBDP-UHFFFAOYSA-N 2-[4-(5-methyl-2-oxo-3h-1-benzofuran-3-yl)phenoxy]acetic acid Chemical compound C12=CC(C)=CC=C2OC(=O)C1C1=CC=C(OCC(O)=O)C=C1 IEUQSYIPXJRBDP-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
229920002396 Polyurea Polymers 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000003446 ligand Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
150000005673 monoalkenes Chemical class 0.000 description 3
239000000178 monomer Substances 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
229960004063 propylene glycol Drugs 0.000 description 3
235000013772 propylene glycol Nutrition 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229920000638 styrene acrylonitrile Polymers 0.000 description 3
239000004416 thermosoftening plastic Substances 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 2
BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 2
MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 2
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
229920002292 Nylon 6 Polymers 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920002367 Polyisobutene Polymers 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
CDJJKTLOZJAGIZ-UHFFFAOYSA-N Tolylacetate Chemical compound CC(=O)OC1=CC=C(C)C=C1 CDJJKTLOZJAGIZ-UHFFFAOYSA-N 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
229920001807 Urea-formaldehyde Polymers 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229920000800 acrylic rubber Polymers 0.000 description 2
230000009471 action Effects 0.000 description 2
239000012190 activator Substances 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
229920000180 alkyd Polymers 0.000 description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000001273 butane Substances 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
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 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
230000009849 deactivation Effects 0.000 description 2
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239000005061 synthetic rubber Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
230000008646 thermal stress Effects 0.000 description 1
229920002803 thermoplastic polyurethane Polymers 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
HXJNZPXGMGELDP-UHFFFAOYSA-J tin(4+);tetrabenzoate Chemical compound [Sn+4].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HXJNZPXGMGELDP-UHFFFAOYSA-J 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
150000003918 triazines Chemical class 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
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
125000005591 trimellitate group Chemical group 0.000 description 1
CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920006337 unsaturated polyester resin Polymers 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
229920001866 very low density polyethylene Polymers 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
- C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered 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
- C08K5/20—Carboxylic acid amides
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5373—Esters of phosphonic acids containing heterocyclic rings not representing cyclic esters of phosphonic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Polymers & Plastics (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Compositions Of Macromolecular Compounds (AREA)
Furan Compounds (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)
Cosmetics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL9300865A 1992-05-22 1993-05-18 3-(carboxymethoxyfenyl)-benzofuran-2-on derivaten als stabilisatoren. NL9300865A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH165392		1992-05-22
CH165392		1992-05-22

Publications (1)

Publication Number	Publication Date
NL9300865A true NL9300865A (nl)	1993-12-16

Family

ID=4215496

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL9300865A NL9300865A (nl)	1992-05-22	1993-05-18	3-(carboxymethoxyfenyl)-benzofuran-2-on derivaten als stabilisatoren.

Country Status (13)

Country	Link
US (1)	US5356966A (cs)
JP (1)	JP3250056B2 (cs)
KR (1)	KR100286116B1 (cs)
BE (1)	BE1006568A3 (cs)
CA (1)	CA2096485A1 (cs)
CZ (1)	CZ290103B6 (cs)
DE (1)	DE4316622A1 (cs)
FR (1)	FR2691469B1 (cs)
GB (1)	GB2267490B (cs)
IT (1)	IT1264451B1 (cs)
NL (1)	NL9300865A (cs)
SK (1)	SK280041B6 (cs)
TW (1)	TW254956B (cs)

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1993
- 1993-05-11 GB GB9309641A patent/GB2267490B/en not_active Expired - Fee Related
- 1993-05-14 KR KR1019930008245A patent/KR100286116B1/ko not_active IP Right Cessation
- 1993-05-14 IT IT93MI000989A patent/IT1264451B1/it active IP Right Grant
- 1993-05-17 US US08/115,119 patent/US5356966A/en not_active Expired - Fee Related
- 1993-05-17 CZ CZ1993918A patent/CZ290103B6/cs not_active IP Right Cessation
- 1993-05-17 SK SK494-93A patent/SK280041B6/sk unknown
- 1993-05-18 BE BE9300512A patent/BE1006568A3/fr not_active IP Right Cessation
- 1993-05-18 FR FR9305959A patent/FR2691469B1/fr not_active Expired - Fee Related
- 1993-05-18 NL NL9300865A patent/NL9300865A/nl not_active Application Discontinuation
- 1993-05-18 CA CA002096485A patent/CA2096485A1/en not_active Abandoned
- 1993-05-18 DE DE4316622A patent/DE4316622A1/de not_active Ceased
- 1993-05-19 JP JP14021993A patent/JP3250056B2/ja not_active Expired - Fee Related
- 1993-05-27 TW TW082103583A patent/TW254956B/zh active

Also Published As

Publication number	Publication date
CA2096485A1 (en)	1993-11-23
SK280041B6 (sk)	1999-07-12
JP3250056B2 (ja)	2002-01-28
ITMI930989A0 (it)	1993-05-14
IT1264451B1 (it)	1996-09-23
JPH0641110A (ja)	1994-02-15
US5356966A (en)	1994-10-18
FR2691469B1 (fr)	1995-02-24
SK49493A3 (en)	1994-05-11
GB2267490A (en)	1993-12-08
CZ91893A3 (en)	1993-12-15
KR100286116B1 (ko)	2001-04-16
CZ290103B6 (cs)	2002-05-15
GB9309641D0 (en)	1993-06-23
GB2267490B (en)	1995-08-09
DE4316622A1 (de)	1993-11-25
TW254956B (cs)	1995-08-21
ITMI930989A1 (it)	1994-11-14
KR940005734A (ko)	1994-03-22
FR2691469A1 (fr)	1993-11-26
BE1006568A3 (fr)	1994-10-18

Publication	Publication Date	Title
NL9300865A (nl)	1993-12-16	3-(carboxymethoxyfenyl)-benzofuran-2-on derivaten als stabilisatoren.
EP0589839B1 (de)	2000-05-10	3-(Dihydrobenzofuran-5-yl)benzofuran-2-one als Stabilisatoren
EP0591102B1 (de)	2000-10-18	3-(2-Acyloxyethoxyphenyl)benzofuran-2-one als Stabilisatoren
US5216052A (en)	1993-06-01	Bisbenzofuran-2-ones
EP0644190B1 (de)	1999-03-17	Benzofuran-2-one als Stabilisatoren
NL9300801A (nl)	1993-12-16	3-(acyloxyfenyl)benzofuran-2-on als stabilisatoren.
DE4220992A1 (de)	1993-01-07	Thiomethylierte benzofuran-2-one
DE4316876A1 (de)	1993-11-25	3-(Alkoxyphenyl)benzofuran-2-one als Stabilisatoren
US5473003A (en)	1995-12-05	Alkanediphenols
EP0601973B1 (de)	1999-10-13	Oligomere HALS-Phosphite und HALS-Phosphonite als Stabilisatoren
EP0594539B1 (de)	1997-05-02	Phenylphosphite als Stabilisatoren für organische Materialien
NL9201446A (nl)	1993-03-01	N-gemethyleerd bis-4-piperidylfosfiet.
EP0608198A1 (de)	1994-07-27	Cyclische Diphenylacetonitrile als Stabilisatoren
DE19513585A1 (de)	1995-10-19	HALS-Phosphite und HALS-Phophoramide als Stabilisatoren
EP0553059B1 (de)	1996-10-09	Neue Cycloalkyliden-bisphenol-phosphite
EP0707035A1 (de)	1996-04-17	HALS-Phosporinane als Stabilisatoren
US20020115855A1 (en)	2002-08-22	Process for the preparation of 3-aryl-benzofuran-2-ones
EP0545861B1 (de)	1995-12-27	Diphenylessigsäurederivate als Stabilisatoren für organisches Material
EP0850946A1 (de)	1998-07-01	Cyclische Phosphinsäurederivate als Stabilisatoren
DE19513543A1 (de)	1995-10-19	HALS-Phosphite als Stabilisatoren
DE19513541A1 (de)	1995-10-19	Monomere und Oligomere Bisphenyl-HALS-Phosphite als Stabilisatoren
NL9102152A (nl)	1992-07-16	Gesubstitueerde dibenzo(d,g)(1,3,2)dioxafosfocinen.

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1996-06-03	BV	The patent application has lapsed