SE523139C2 - Hydroxifenyltriaziner och användning av dessa som stabilisatorer samt kompositioner därav - Google Patents

Info

Publication number

SE523139C2

SE523139C2 SE9701012A SE9701012A SE523139C2 SE 523139 C2 SE523139 C2 SE 523139C2 SE 9701012 A SE9701012 A SE 9701012A SE 9701012 A SE9701012 A SE 9701012A SE 523139 C2 SE523139 C2 SE 523139C2

Authority

SE

Sweden

Prior art keywords

phenyl

alkyl

formula

tert

butyl

Prior art date

1996-03-26

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• 239000000203 mixture Substances 0.000 title claims abstract description 67
• 239000003381 stabilizer Substances 0.000 title claims description 35
• VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical class OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 109
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 17
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
• 239000001301 oxygen Substances 0.000 claims abstract description 17
• 229920005613 synthetic organic polymer Polymers 0.000 claims abstract description 7
• -1 Ca-C8-alkenoxy Chemical group 0.000 claims description 130
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
• 125000000217 alkyl group Chemical group 0.000 claims description 44
• 229910052799 carbon Inorganic materials 0.000 claims description 33
• 238000000034 method Methods 0.000 claims description 27
• 238000000576 coating method Methods 0.000 claims description 26
• 150000001412 amines Chemical class 0.000 claims description 18
• 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 18
• 239000001257 hydrogen Substances 0.000 claims description 17
• 239000011248 coating agent Substances 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 9
• 229920001169 thermoplastic Polymers 0.000 claims description 7
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 6
• 230000000087 stabilizing effect Effects 0.000 claims description 5
• 239000000853 adhesive Substances 0.000 claims description 4
• 230000001070 adhesive effect Effects 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 239000011368 organic material Substances 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims description 3
• 230000009931 harmful effect Effects 0.000 claims description 3
• FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 2
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
• 239000004611 light stabiliser Substances 0.000 claims description 2
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
• 125000005293 bicycloalkoxy group Chemical group 0.000 claims 1
• 230000000254 damaging effect Effects 0.000 abstract 1
• 229910052757 nitrogen Inorganic materials 0.000 description 47
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 43
• 229920001577 copolymer Polymers 0.000 description 32
• 229920000642 polymer Polymers 0.000 description 32
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 30
• 238000012512 characterization method Methods 0.000 description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
• 239000003054 catalyst Substances 0.000 description 21
• 239000010410 layer Substances 0.000 description 20
• 239000011230 binding agent Substances 0.000 description 19
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 18
• 229920005989 resin Polymers 0.000 description 18
• 239000011347 resin Substances 0.000 description 18
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 17
• 239000003973 paint Substances 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
• 229910052751 metal Inorganic materials 0.000 description 15
• 239000002184 metal Substances 0.000 description 15
• 238000004458 analytical method Methods 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 239000004922 lacquer Substances 0.000 description 12
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 12
• 239000004952 Polyamide Substances 0.000 description 11
• 239000002253 acid Substances 0.000 description 11
• 239000008199 coating composition Substances 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• 229920002647 polyamide Polymers 0.000 description 11
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 125000001309 chloro group Chemical group Cl* 0.000 description 10
• 238000002844 melting Methods 0.000 description 10
• 230000008018 melting Effects 0.000 description 10
• 229920000915 polyvinyl chloride Polymers 0.000 description 10
• 239000004800 polyvinyl chloride Substances 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• 229920000877 Melamine resin Polymers 0.000 description 9
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
• 239000005062 Polybutadiene Substances 0.000 description 9
• 239000004743 Polypropylene Substances 0.000 description 9
• 229920001684 low density polyethylene Polymers 0.000 description 9
• 239000004702 low-density polyethylene Substances 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• 229920002857 polybutadiene Polymers 0.000 description 9
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
• 125000003342 alkenyl group Chemical group 0.000 description 8
• 239000012964 benzotriazole Substances 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 125000000753 cycloalkyl group Chemical group 0.000 description 8
• 238000001035 drying Methods 0.000 description 8
• 150000004820 halides Chemical class 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 239000004417 polycarbonate Substances 0.000 description 8
• 239000008096 xylene Substances 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
• 150000001298 alcohols Chemical class 0.000 description 7
• 239000007859 condensation product Substances 0.000 description 7
• 239000012043 crude product Substances 0.000 description 7
• 238000001723 curing Methods 0.000 description 7
• 229920001971 elastomer Polymers 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 238000002156 mixing Methods 0.000 description 7
• 229920000058 polyacrylate Polymers 0.000 description 7
• 229920000728 polyester Polymers 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 150000003839 salts Chemical class 0.000 description 7
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 6
• 239000004925 Acrylic resin Substances 0.000 description 6
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
• 239000004721 Polyphenylene oxide Substances 0.000 description 6
• 239000007983 Tris buffer Substances 0.000 description 6
• 229910052782 aluminium Inorganic materials 0.000 description 6
• 238000004440 column chromatography Methods 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 229920001903 high density polyethylene Polymers 0.000 description 6
• 239000004700 high-density polyethylene Substances 0.000 description 6
• 150000002739 metals Chemical class 0.000 description 6
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
• 150000002989 phenols Chemical class 0.000 description 6
• 239000005056 polyisocyanate Substances 0.000 description 6
• 229920001228 polyisocyanate Polymers 0.000 description 6
• 239000004814 polyurethane Substances 0.000 description 6
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
• 238000002360 preparation method Methods 0.000 description 6
• 230000005855 radiation Effects 0.000 description 6
• 239000000758 substrate Substances 0.000 description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 5
• 241000209094 Oryza Species 0.000 description 5
• 235000007164 Oryza sativa Nutrition 0.000 description 5
• 239000004698 Polyethylene Substances 0.000 description 5
• 239000000654 additive Substances 0.000 description 5
• 125000001931 aliphatic group Chemical group 0.000 description 5
• 125000003545 alkoxy group Chemical group 0.000 description 5
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
• 150000008064 anhydrides Chemical class 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• 239000000460 chlorine Substances 0.000 description 5
• 238000005336 cracking Methods 0.000 description 5
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 5
• 150000002170 ethers Chemical class 0.000 description 5
• 238000010348 incorporation Methods 0.000 description 5
• 239000012948 isocyanate Substances 0.000 description 5
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
• 239000000049 pigment Substances 0.000 description 5
• 229920000647 polyepoxide Polymers 0.000 description 5
• 229920000570 polyether Polymers 0.000 description 5
• 229920000573 polyethylene Polymers 0.000 description 5
• 229920001155 polypropylene Polymers 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 238000001953 recrystallisation Methods 0.000 description 5
• 235000009566 rice Nutrition 0.000 description 5
• 239000007787 solid Substances 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
• ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
• YCNFNXPUWNPXMG-UHFFFAOYSA-N 4-(4,6-diphenyl-1,3,5-triazin-2-yl)benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 YCNFNXPUWNPXMG-UHFFFAOYSA-N 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• 229920002943 EPDM rubber Polymers 0.000 description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 229910019142 PO4 Inorganic materials 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
• 229920000180 alkyd Polymers 0.000 description 4
• 125000003277 amino group Chemical group 0.000 description 4
• FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 4
• 238000009835 boiling Methods 0.000 description 4
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
• 229910052801 chlorine Inorganic materials 0.000 description 4
• MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
• 150000002366 halogen compounds Chemical class 0.000 description 4
• 229930195733 hydrocarbon Natural products 0.000 description 4
• 150000002430 hydrocarbons Chemical class 0.000 description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
• 229910052748 manganese Inorganic materials 0.000 description 4
• 239000011572 manganese Substances 0.000 description 4
• DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
• SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
• 125000003884 phenylalkyl group Chemical group 0.000 description 4
• 229920003023 plastic Polymers 0.000 description 4
• 239000004033 plastic Substances 0.000 description 4
• 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
• 229920001707 polybutylene terephthalate Polymers 0.000 description 4
• 229920006380 polyphenylene oxide Polymers 0.000 description 4
• 229920002635 polyurethane Polymers 0.000 description 4
• 235000013772 propylene glycol Nutrition 0.000 description 4
• GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
• 239000005060 rubber Substances 0.000 description 4
• 230000006641 stabilisation Effects 0.000 description 4
• 238000011105 stabilization Methods 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
• ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
• WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 4
• FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
• RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
• 229940126062 Compound A Drugs 0.000 description 3
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 239000003490 Thiodipropionic acid Substances 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 239000003963 antioxidant agent Substances 0.000 description 3
• 235000006708 antioxidants Nutrition 0.000 description 3
• 150000001991 dicarboxylic acids Chemical class 0.000 description 3
• 150000001993 dienes Chemical class 0.000 description 3
• NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 3
• 239000000806 elastomer Substances 0.000 description 3
• 150000002118 epoxides Chemical class 0.000 description 3
• JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 3
• 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 230000008020 evaporation Effects 0.000 description 3
• 239000000945 filler Substances 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
• 229920000554 ionomer Polymers 0.000 description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• 239000003446 ligand Substances 0.000 description 3
• 239000000178 monomer Substances 0.000 description 3
• FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 3
• 150000002815 nickel Chemical class 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
• 238000006116 polymerization reaction Methods 0.000 description 3
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
• 229910052709 silver Inorganic materials 0.000 description 3
• 239000004332 silver Substances 0.000 description 3
• 239000011343 solid material Substances 0.000 description 3
• 229920001187 thermosetting polymer 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
• 229920002554 vinyl polymer Polymers 0.000 description 3
• 229910052725 zinc Inorganic materials 0.000 description 3
• 239000011701 zinc Substances 0.000 description 3
• 229910052726 zirconium Inorganic materials 0.000 description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
• 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
• ZQMPWXFHAUDENN-UHFFFAOYSA-N 1,2-bis[(2-methylphenyl)amino]ethane Natural products CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZQMPWXFHAUDENN-UHFFFAOYSA-N 0.000 description 2
• BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
• 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
• BUGAMLAPDQMYNZ-UHFFFAOYSA-N 1-(2,4,4-trimethylpentan-2-yl)-10h-phenothiazine Chemical class S1C2=CC=CC=C2NC2=C1C=CC=C2C(C)(C)CC(C)(C)C BUGAMLAPDQMYNZ-UHFFFAOYSA-N 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
• BWJKLDGAAPQXGO-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-octadecoxypiperidine Chemical compound CCCCCCCCCCCCCCCCCCOC1CC(C)(C)NC(C)(C)C1 BWJKLDGAAPQXGO-UHFFFAOYSA-N 0.000 description 2
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