BE1006568A3

BE1006568A3 - 3-(carboxymethoxyphenyl) benzofuran-2-ones comme stabilisants.

3-(carboxymethoxyphenyl) benzofuran-2-ones comme stabilisants. Download PDF

Info

Publication number: BE1006568A3
Authority: BE; Belgium
Prior art keywords: group; atom; alkyl group; sep; hydrogen atom
Prior art date: 1992-05-22

Application number

BE9300512A

Other languages

English (en)

French (fr)

Original Assignee

Ciba Geigy Ag

Priority date

1992-05-22

Filing date

1993-05-18

Publication date

1994-10-18

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

1994-10-18 Application granted granted Critical

1994-10-18 Publication of BE1006568A3 publication Critical patent/BE1006568A3/fr

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239000003381 stabilizer Substances 0.000 title claims abstract description 14
-1 carboxymethoxyphenyl Chemical group 0.000 title claims description 125
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 48
125000000217 alkyl group Chemical group 0.000 claims abstract description 45
125000003545 alkoxy group Chemical group 0.000 claims abstract description 43
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 17
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims abstract description 12
125000004423 acyloxy group Chemical group 0.000 claims abstract description 11
125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 10
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 8
125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 5
125000002071 phenylalkoxy group Chemical group 0.000 claims abstract description 5
125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims abstract 3
125000003884 phenylalkyl group Chemical group 0.000 claims abstract 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 107
150000001875 compounds Chemical class 0.000 claims description 68
150000003254 radicals Chemical class 0.000 claims description 59
239000000203 mixture Substances 0.000 claims description 53
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
125000004429 atom Chemical group 0.000 claims description 30
229910052760 oxygen Inorganic materials 0.000 claims description 20
239000001301 oxygen Substances 0.000 claims description 20
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 19
125000004434 sulfur atom Chemical group 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
239000011368 organic material Substances 0.000 claims description 12
125000004432 carbon atom Chemical group C* 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 11
230000015556 catabolic process Effects 0.000 claims description 9
238000006731 degradation reaction Methods 0.000 claims description 9
125000004430 oxygen atom Chemical group O* 0.000 claims description 9
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
230000001590 oxidative effect Effects 0.000 claims description 8
230000006641 stabilisation Effects 0.000 claims description 8
238000011105 stabilization Methods 0.000 claims description 8
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
230000008569 process Effects 0.000 claims description 3
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
229910052707 ruthenium Inorganic materials 0.000 claims description 2
229920001059 synthetic polymer Polymers 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 3
150000001457 metallic cations Chemical class 0.000 claims 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
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 abstract description 5
125000001424 substituent group Chemical group 0.000 abstract 2
229920001577 copolymer Polymers 0.000 description 37
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
229920000642 polymer Polymers 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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
239000004952 Polyamide Substances 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
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
229920002647 polyamide Polymers 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 10
229920002857 polybutadiene Polymers 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
239000005977 Ethylene Substances 0.000 description 9
239000005062 Polybutadiene Substances 0.000 description 9
239000004698 Polyethylene Substances 0.000 description 9
239000002253 acid Substances 0.000 description 9
229920001684 low density polyethylene Polymers 0.000 description 9
239000004702 low-density polyethylene Substances 0.000 description 9
229920000573 polyethylene Polymers 0.000 description 9
229920005989 resin Polymers 0.000 description 9
239000011347 resin Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 8
229920001155 polypropylene Polymers 0.000 description 8
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
238000004821 distillation Methods 0.000 description 7
239000000463 material Substances 0.000 description 7
229920000098 polyolefin Polymers 0.000 description 7
229920006324 polyoxymethylene Polymers 0.000 description 7
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
150000001412 amines Chemical class 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-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
150000005846 sugar alcohols Polymers 0.000 description 6
229920002943 EPDM rubber Polymers 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
150000001993 dienes Chemical class 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
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
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 4
KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
ISWSIWMERMANOR-UHFFFAOYSA-N 2-[4-(carboxymethoxy)phenyl]-2-hydroxyacetic acid Chemical group OC(=O)C(O)C1=CC=C(OCC(O)=O)C=C1 ISWSIWMERMANOR-UHFFFAOYSA-N 0.000 description 4
ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-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
CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
150000001252 acrylic acid derivatives Chemical class 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
229940093476 ethylene glycol Drugs 0.000 description 4
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
229920001903 high density polyethylene Polymers 0.000 description 4
239000004700 high-density polyethylene Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
229940117969 neopentyl glycol Drugs 0.000 description 4
150000002815 nickel Chemical class 0.000 description 4
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
238000006116 polymerization reaction Methods 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
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000002904 solvent Substances 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
229920002554 vinyl polymer Polymers 0.000 description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
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WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 3
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NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
229920000877 Melamine resin Polymers 0.000 description 3
229920002396 Polyurea Polymers 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
125000003118 aryl group Chemical group 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
150000001768 cations Chemical class 0.000 description 3
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239000003480 eluent Substances 0.000 description 3
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001125 extrusion Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
239000003446 ligand Substances 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
150000005673 monoalkenes Chemical class 0.000 description 3
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239000000741 silica gel Substances 0.000 description 3
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238000005507 spraying Methods 0.000 description 3
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 3
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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
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125000004642 (C1-C12) alkoxy group Chemical group 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
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HCILJBJJZALOAL-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-n'-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]propanehydrazide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 HCILJBJJZALOAL-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
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
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