TWI303646B - Polyester and polyamide compositions of low residual aldehyde content - Google Patents

Info

Publication number

TWI303646B

TWI303646B TW091123048A TW91123048A TWI303646B TW I303646 B TWI303646 B TW I303646B TW 091123048 A TW091123048 A TW 091123048A TW 91123048 A TW91123048 A TW 91123048A TW I303646 B TWI303646 B TW I303646B

Authority

TW

Taiwan

Prior art keywords

group

alkyl

substituted

phenyl

unsubstituted

Prior art date

2001-10-09

Links

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• 239000000203 mixture Substances 0.000 title claims abstract description 118
• 239000004952 Polyamide Substances 0.000 title claims abstract description 38
• 229920002647 polyamide Polymers 0.000 title claims abstract description 38
• 229920006149 polyester-amide block copolymer Polymers 0.000 title claims abstract description 21
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims 15
• -1 poly(ethylene terephthalate) Polymers 0.000 claims abstract description 300
• 229920000139 polyethylene terephthalate Polymers 0.000 claims abstract description 135
• 239000005020 polyethylene terephthalate Substances 0.000 claims abstract description 135
• 150000001875 compounds Chemical class 0.000 claims abstract description 113
• 229920000728 polyester Polymers 0.000 claims abstract description 76
• 239000003381 stabilizer Substances 0.000 claims abstract description 27
• 239000000835 fiber Substances 0.000 claims abstract description 21
• 125000000217 alkyl group Chemical group 0.000 claims description 94
• 239000002585 base Substances 0.000 claims description 77
• 229920000768 polyamine Polymers 0.000 claims description 67
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 65
• 239000001301 oxygen Substances 0.000 claims description 64
• 229910052760 oxygen Inorganic materials 0.000 claims description 64
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 63
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• 229910052717 sulfur Inorganic materials 0.000 claims description 60
• 239000011593 sulfur Substances 0.000 claims description 60
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 58
• 239000001257 hydrogen Substances 0.000 claims description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims description 53
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 50
• 238000000034 method Methods 0.000 claims description 39
• 150000001412 amines Chemical class 0.000 claims description 38
• 125000004432 carbon atom Chemical group C* 0.000 claims description 38
• 230000015572 biosynthetic process Effects 0.000 claims description 34
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 33
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 31
• 230000000087 stabilizing effect Effects 0.000 claims description 30
• 238000010128 melt processing Methods 0.000 claims description 28
• 150000002431 hydrogen Chemical class 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 239000000356 contaminant Substances 0.000 claims description 25
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 24
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 21
• 238000002360 preparation method Methods 0.000 claims description 21
• 229920000642 polymer Polymers 0.000 claims description 20
• 239000000049 pigment Substances 0.000 claims description 19
• 150000003077 polyols Chemical class 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 229920005862 polyol Polymers 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000002947 alkylene group Chemical group 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 239000000975 dye Substances 0.000 claims description 16
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 229920001577 copolymer Polymers 0.000 claims description 14
• 230000008569 process Effects 0.000 claims description 14
• 230000006641 stabilisation Effects 0.000 claims description 14
• 238000011105 stabilization Methods 0.000 claims description 14
• 238000006243 chemical reaction Methods 0.000 claims description 13
• 150000002148 esters Chemical class 0.000 claims description 13
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 13
• 125000003277 amino group Chemical group 0.000 claims description 12
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 12
• 150000002009 diols Chemical class 0.000 claims description 11
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 10
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
• ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 9
• 239000011737 fluorine Substances 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 239000007789 gas Substances 0.000 claims description 9
• 238000002844 melting Methods 0.000 claims description 9
• 230000008018 melting Effects 0.000 claims description 9
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 238000004383 yellowing Methods 0.000 claims description 8
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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 7
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
• SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 7
• 229920003023 plastic Polymers 0.000 claims description 7
• 239000004033 plastic Substances 0.000 claims description 7
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 6
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
• 239000004305 biphenyl Substances 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 239000000460 chlorine Substances 0.000 claims description 6
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 229910052751 metal Inorganic materials 0.000 claims description 6
• 239000002184 metal Substances 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical group NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 5
• 125000005605 benzo group Chemical group 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 5
• 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
• 238000012545 processing Methods 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
• TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
• 239000005977 Ethylene Substances 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 235000010290 biphenyl Nutrition 0.000 claims description 4
• 150000001768 cations Chemical class 0.000 claims description 4
• RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical group N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000005010 perfluoroalkyl group Chemical group 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
• 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 4
• 150000003254 radicals Chemical class 0.000 claims description 4
• 239000003760 tallow Substances 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
• WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 3
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000001589 carboacyl group Chemical group 0.000 claims description 3
• 150000001924 cycloalkanes Chemical class 0.000 claims description 3
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 150000005690 diesters Chemical class 0.000 claims description 3
• 230000032050 esterification Effects 0.000 claims description 3
• 238000005886 esterification reaction Methods 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 150000002443 hydroxylamines Chemical class 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 230000003647 oxidation Effects 0.000 claims description 3
• 238000007254 oxidation reaction Methods 0.000 claims description 3
• 125000005561 phenanthryl group Chemical group 0.000 claims description 3
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 3
• 229950000688 phenothiazine Drugs 0.000 claims description 3
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 2
• CAPNUXMLPONECZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-2-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=C(O)C(C(C)(C)C)=C1 CAPNUXMLPONECZ-UHFFFAOYSA-N 0.000 claims description 2
• 239000004215 Carbon black (E152) Substances 0.000 claims description 2
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• 229930195733 hydrocarbon Natural products 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
• 239000000178 monomer Substances 0.000 claims description 2
• HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 2
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
• 125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
• 229920002401 polyacrylamide Polymers 0.000 claims description 2
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• 238000005809 transesterification reaction Methods 0.000 claims description 2
• 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• NYNRDINGKLPEGU-UHFFFAOYSA-N 2,4-bis[(dimethylamino)methyl]-6-methylphenol Chemical compound CN(C)CC1=CC(C)=C(O)C(CN(C)C)=C1 NYNRDINGKLPEGU-UHFFFAOYSA-N 0.000 claims 1
• CGBAAHJKWUIALT-UHFFFAOYSA-N 2,4-ditert-butyl-6-(methoxymethyl)phenol Chemical compound COCC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O CGBAAHJKWUIALT-UHFFFAOYSA-N 0.000 claims 1
• KKHZJNRQSWMVFJ-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound CN(C)CC1=C(O)C=CC(=C1)C(C)(C)C1=CC=C(C=C1)O KKHZJNRQSWMVFJ-UHFFFAOYSA-N 0.000 claims 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
• 239000003513 alkali Substances 0.000 claims 1
• 125000005236 alkanoylamino group Chemical group 0.000 claims 1
• 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
• 229910000071 diazene Inorganic materials 0.000 claims 1
• QEHLSPSXOPFMDI-UHFFFAOYSA-N hydrazinylmethanethiol Chemical compound NNCS QEHLSPSXOPFMDI-UHFFFAOYSA-N 0.000 claims 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
• 125000005641 methacryl group Chemical group 0.000 claims 1
• SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims 1
• 150000004032 porphyrins Chemical class 0.000 claims 1
• YYMWVZQRBNARFZ-UHFFFAOYSA-M sodium;2-[2,3-bis(sulfanyl)propoxy]ethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCOCC(S)CS YYMWVZQRBNARFZ-UHFFFAOYSA-M 0.000 claims 1
• 150000003573 thiols Chemical class 0.000 claims 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract description 233
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 28
• 238000001125 extrusion Methods 0.000 abstract description 21
• 238000004519 manufacturing process Methods 0.000 abstract description 12
• 235000013305 food Nutrition 0.000 abstract description 9
• 235000013361 beverage Nutrition 0.000 abstract description 7
• 239000000463 material Substances 0.000 abstract description 2
• 239000000654 additive Substances 0.000 description 62
• 230000000996 additive effect Effects 0.000 description 51
• XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
• 239000010408 film Substances 0.000 description 36
• 239000010410 layer Substances 0.000 description 34
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• 239000000243 solution Substances 0.000 description 32
• 239000000047 product Substances 0.000 description 28
• 150000001299 aldehydes Chemical class 0.000 description 25
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 238000010438 heat treatment Methods 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
• 235000019439 ethyl acetate Nutrition 0.000 description 21
• 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
• 101150041968 CDC13 gene Proteins 0.000 description 17
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 16
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
• 230000002829 reductive effect Effects 0.000 description 15
• 238000009472 formulation Methods 0.000 description 14
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 14
• 238000010992 reflux Methods 0.000 description 14
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 13
• 239000007983 Tris buffer Substances 0.000 description 13
• 230000009467 reduction Effects 0.000 description 13
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 12
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
• 238000005481 NMR spectroscopy Methods 0.000 description 11
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 11
• 239000012964 benzotriazole Substances 0.000 description 11
• 239000002904 solvent Substances 0.000 description 11
• 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 10
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 10
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 10
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 10
• 239000010949 copper Substances 0.000 description 10
• 238000005259 measurement Methods 0.000 description 10
• 229960003742 phenol Drugs 0.000 description 10
• 239000000600 sorbitol Substances 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• 125000003118 aryl group Chemical group 0.000 description 7
• 150000001721 carbon Chemical group 0.000 description 7
• 239000013078 crystal Substances 0.000 description 7
• 239000004744 fabric Substances 0.000 description 7
• 239000008098 formaldehyde solution Substances 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 229920005989 resin Polymers 0.000 description 7
• 239000011347 resin Substances 0.000 description 7
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
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