CA2762361A1 - Novel sterically hindered amine light stabilizers - Google Patents

Info

Publication number

CA2762361A1

CA2762361A1 CA2762361A CA2762361A CA2762361A1 CA 2762361 A1 CA2762361 A1 CA 2762361A1 CA 2762361 A CA2762361 A CA 2762361A CA 2762361 A CA2762361 A CA 2762361A CA 2762361 A1 CA2762361 A1 CA 2762361A1

Authority

CA

Canada

Prior art keywords

formula

compound

phenyl

tert

c20alkyl

Prior art date

2009-06-08

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001412 amines Chemical class 0.000 title claims abstract description 27
• 239000004611 light stabiliser Substances 0.000 title claims description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 101
• 230000000087 stabilizing effect Effects 0.000 claims abstract description 8
• 238000000576 coating method Methods 0.000 claims abstract description 6
• 229920001169 thermoplastic Polymers 0.000 claims abstract description 5
• 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 5
• 239000000203 mixture Substances 0.000 claims description 45
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• 238000000034 method Methods 0.000 claims description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 239000002904 solvent Substances 0.000 claims description 13
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 12
• 229910052751 metal Inorganic materials 0.000 claims description 11
• 239000002184 metal Substances 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• 229920000620 organic polymer Polymers 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 239000012948 isocyanate Substances 0.000 claims description 8
• 150000002513 isocyanates Chemical class 0.000 claims description 8
• 150000002576 ketones Chemical class 0.000 claims description 7
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 229910021529 ammonia Inorganic materials 0.000 claims description 5
• 239000003063 flame retardant Substances 0.000 claims description 5
• 239000000463 material Substances 0.000 claims description 5
• 239000002243 precursor Substances 0.000 claims description 5
• 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 4
• 239000003963 antioxidant agent Substances 0.000 claims description 4
• 230000000694 effects Effects 0.000 claims description 4
• 229910044991 metal oxide Inorganic materials 0.000 claims description 4
• 150000004706 metal oxides Chemical class 0.000 claims description 4
• 125000006178 methyl benzyl group Chemical group 0.000 claims description 4
• 239000000049 pigment Substances 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 3
• 239000006096 absorbing agent Substances 0.000 claims description 3
• 125000005442 diisocyanate group Chemical group 0.000 claims description 3
• 125000005594 diketone group Chemical group 0.000 claims description 3
• 150000002443 hydroxylamines Chemical class 0.000 claims description 3
• 239000004014 plasticizer Substances 0.000 claims description 3
• ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 2
• 230000002411 adverse Effects 0.000 claims description 2
• 239000011230 binding agent Substances 0.000 claims description 2
• 239000011248 coating agent Substances 0.000 claims description 2
• 239000000975 dye Substances 0.000 claims description 2
• 150000002903 organophosphorus compounds Chemical class 0.000 claims description 2
• 239000013008 thixotropic agent Substances 0.000 claims description 2
• 229910052727 yttrium Inorganic materials 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
• 229920000642 polymer Polymers 0.000 abstract description 32
• 229910052757 nitrogen Inorganic materials 0.000 abstract description 19
• 239000002253 acid Substances 0.000 abstract description 17
• 239000003381 stabilizer Substances 0.000 abstract description 12
• 238000006467 substitution reaction Methods 0.000 abstract description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
• 238000012545 processing Methods 0.000 abstract description 3
• YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical group CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 abstract description 2
• 150000001336 alkenes Chemical class 0.000 abstract description 2
• 230000002939 deleterious effect Effects 0.000 abstract description 2
• 230000001590 oxidative effect Effects 0.000 abstract description 2
• 230000005855 radiation Effects 0.000 abstract description 2
• -1 spiropiperidine pyrrolidine dione derivatives Chemical class 0.000 description 65
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 52
• 229920001577 copolymer Polymers 0.000 description 42
• 229940044603 styrene Drugs 0.000 description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 16
• 239000005977 Ethylene Substances 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 16
• 239000003054 catalyst Substances 0.000 description 14
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
• 239000004743 Polypropylene Substances 0.000 description 13
• 229910052799 carbon Inorganic materials 0.000 description 13
• 101150041968 CDC13 gene Proteins 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
• 239000004952 Polyamide Substances 0.000 description 11
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical class CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 229920002647 polyamide Polymers 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 150000007513 acids Chemical class 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• 239000011541 reaction mixture Substances 0.000 description 9
• 238000005160 1H NMR spectroscopy Methods 0.000 description 8
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
• 239000005062 Polybutadiene Substances 0.000 description 8
• 125000000217 alkyl group Chemical group 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 229920001684 low density polyethylene Polymers 0.000 description 8
• 239000004702 low-density polyethylene Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 229920002857 polybutadiene Polymers 0.000 description 8
• 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 8
• 229920002554 vinyl polymer Polymers 0.000 description 8
• 230000002378 acidificating effect Effects 0.000 description 7
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
• 125000003118 aryl group Chemical group 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• 239000004700 high-density polyethylene Substances 0.000 description 7
• 239000000178 monomer Substances 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• 230000003750 conditioning effect Effects 0.000 description 6
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
• 229940052303 ethers for general anesthesia Drugs 0.000 description 6
• 229920001903 high density polyethylene Polymers 0.000 description 6
• 239000004417 polycarbonate Substances 0.000 description 6
• 229920000728 polyester Polymers 0.000 description 6
• 229920000098 polyolefin Polymers 0.000 description 6
• 229920001155 polypropylene Polymers 0.000 description 6
• 239000004800 polyvinyl chloride Substances 0.000 description 6
• 229920000915 polyvinyl chloride Polymers 0.000 description 6
• 229910052938 sodium sulfate Inorganic materials 0.000 description 6
• 235000011152 sodium sulphate Nutrition 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
• 229920000877 Melamine resin Polymers 0.000 description 5
• 239000004698 Polyethylene Substances 0.000 description 5
• 239000004721 Polyphenylene oxide Substances 0.000 description 5
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
• 229910052731 fluorine Inorganic materials 0.000 description 5
• 229920001519 homopolymer Polymers 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
• 229920006380 polyphenylene oxide Polymers 0.000 description 5
• 150000005846 sugar alcohols Polymers 0.000 description 5
• KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 5
• 229920001897 terpolymer Polymers 0.000 description 5
• KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
• 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 4
• ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
• MQHNXHVWEZFREI-UHFFFAOYSA-N 1-methoxy-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CON1C(C)(C)CC(=O)CC1(C)C MQHNXHVWEZFREI-UHFFFAOYSA-N 0.000 description 4
• KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
• ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
• RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 4
• CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-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
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
• JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 4
• ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-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
• 239000002585 base Substances 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 229920001971 elastomer Polymers 0.000 description 4
• 150000002170 ethers Chemical class 0.000 description 4
• XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
• 150000002815 nickel Chemical class 0.000 description 4
• 239000012074 organic phase Substances 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
• 229920000573 polyethylene Polymers 0.000 description 4
• 239000004814 polyurethane Substances 0.000 description 4
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
• 229940095050 propylene Drugs 0.000 description 4
• 235000013772 propylene glycol Nutrition 0.000 description 4
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
• 150000003254 radicals Chemical class 0.000 description 4
• 239000007787 solid Substances 0.000 description 4
• 239000000600 sorbitol Substances 0.000 description 4
• YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
• 239000011732 tocopherol Substances 0.000 description 4
• ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
• 229940113165 trimethylolpropane Drugs 0.000 description 4
• LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 4
• MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 3
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
• 229920000089 Cyclic olefin copolymer Polymers 0.000 description 3
• 229920002943 EPDM rubber Polymers 0.000 description 3
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
• 239000004793 Polystyrene Substances 0.000 description 3
• 229920002396 Polyurea Polymers 0.000 description 3
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 239000007983 Tris buffer Substances 0.000 description 3
• BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
• 239000000654 additive Substances 0.000 description 3
• 125000001931 aliphatic group Chemical group 0.000 description 3
• 229920000180 alkyd Polymers 0.000 description 3
• 235000006708 antioxidants Nutrition 0.000 description 3
• 229920001585 atactic polymer Polymers 0.000 description 3
• 239000012964 benzotriazole Substances 0.000 description 3
• 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 3
• MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 238000006555 catalytic reaction Methods 0.000 description 3
• 239000007795 chemical reaction product Substances 0.000 description 3
• 239000003431 cross linking reagent Substances 0.000 description 3
• 125000004122 cyclic group Chemical group 0.000 description 3
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
• 238000010511 deprotection reaction Methods 0.000 description 3
• 150000001991 dicarboxylic acids Chemical class 0.000 description 3
• 238000001035 drying Methods 0.000 description 3
• 239000003822 epoxy resin Substances 0.000 description 3
• HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
• 239000005038 ethylene vinyl acetate Substances 0.000 description 3
• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
• 125000000623 heterocyclic group Chemical group 0.000 description 3
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
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