DE60217151T2 - Polyester- und polyamidzusammensetzungen mit niedrigem restaldehydgehalt - Google Patents

Info

Publication number

DE60217151T2

DE60217151T2 DE60217151T DE60217151T DE60217151T2 DE 60217151 T2 DE60217151 T2 DE 60217151T2 DE 60217151 T DE60217151 T DE 60217151T DE 60217151 T DE60217151 T DE 60217151T DE 60217151 T2 DE60217151 T2 DE 60217151T2

Authority

DE

Germany

Prior art keywords

alkyl

tert

substituted

butyl

unsubstituted

Prior art date

2001-10-09

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.)

Expired - Lifetime

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• 229920002647 polyamide Polymers 0.000 title claims abstract description 102
• 239000004952 Polyamide Substances 0.000 title claims abstract description 95
• 239000000203 mixture Substances 0.000 title claims abstract description 92
• 229920000728 polyester Polymers 0.000 title claims abstract description 71
• -1 poly(ethylene terephthalate) Polymers 0.000 claims abstract description 208
• 229920000139 polyethylene terephthalate Polymers 0.000 claims abstract description 148
• 239000005020 polyethylene terephthalate Substances 0.000 claims abstract description 148
• 150000001875 compounds Chemical class 0.000 claims abstract description 113
• 239000003381 stabilizer Substances 0.000 claims abstract description 33
• 229920006149 polyester-amide block copolymer Polymers 0.000 claims abstract description 32
• 239000000835 fiber Substances 0.000 claims abstract description 21
• 238000004519 manufacturing process Methods 0.000 claims abstract description 10
• 239000001301 oxygen Substances 0.000 claims description 88
• 229910052760 oxygen Inorganic materials 0.000 claims description 88
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 81
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 68
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• 229910052717 sulfur Inorganic materials 0.000 claims description 62
• 239000011593 sulfur Substances 0.000 claims description 62
• 239000001257 hydrogen Substances 0.000 claims description 58
• 229910052739 hydrogen Inorganic materials 0.000 claims description 58
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
• 125000004432 carbon atom Chemical group C* 0.000 claims description 39
• 150000002431 hydrogen Chemical class 0.000 claims description 36
• 230000015572 biosynthetic process Effects 0.000 claims description 35
• 238000000034 method Methods 0.000 claims description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
• 238000010128 melt processing Methods 0.000 claims description 28
• 230000000087 stabilizing effect Effects 0.000 claims description 28
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 26
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 150000001412 amines Chemical class 0.000 claims description 23
• 229920000642 polymer Polymers 0.000 claims description 23
• 125000002947 alkylene group Chemical group 0.000 claims description 22
• 238000002360 preparation method Methods 0.000 claims description 22
• 230000008569 process Effects 0.000 claims description 22
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 21
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 21
• 150000005690 diesters Chemical class 0.000 claims description 21
• 150000005846 sugar alcohols Polymers 0.000 claims description 20
• 125000001589 carboacyl group Chemical group 0.000 claims description 19
• 229920001577 copolymer Polymers 0.000 claims description 19
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
• 239000012535 impurity Substances 0.000 claims description 18
• 239000000975 dye Substances 0.000 claims description 17
• 239000000049 pigment Substances 0.000 claims description 17
• 125000004423 acyloxy group Chemical group 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 150000002148 esters Chemical class 0.000 claims description 16
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 16
• ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 15
• 125000001153 fluoro group Chemical group F* 0.000 claims description 14
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 14
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 9
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 9
• 125000004957 naphthylene group Chemical group 0.000 claims description 9
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 8
• 125000005605 benzo group Chemical group 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
• 125000001118 alkylidene group Chemical group 0.000 claims description 7
• 150000002009 diols Chemical class 0.000 claims description 7
• 229920003023 plastic Polymers 0.000 claims description 7
• 239000004033 plastic Substances 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 239000004215 Carbon black (E152) Substances 0.000 claims description 6
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 239000011888 foil Substances 0.000 claims description 6
• 125000000743 hydrocarbylene group Chemical group 0.000 claims description 6
• 229910052751 metal Inorganic materials 0.000 claims description 6
• 239000002184 metal Substances 0.000 claims description 6
• 239000000178 monomer Substances 0.000 claims description 6
• AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 claims description 5
• HKFRBBJLBRGTLM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O HKFRBBJLBRGTLM-UHFFFAOYSA-N 0.000 claims description 5
• NOCZUJDWKXXYKK-UHFFFAOYSA-N 2,6-bis[(dimethylamino)methyl]-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CN(C)CC1=CC(C(C)(C)CC(C)(C)C)=CC(CN(C)C)=C1O NOCZUJDWKXXYKK-UHFFFAOYSA-N 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 5
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
• 235000010290 biphenyl Nutrition 0.000 claims description 5
• 239000004305 biphenyl Substances 0.000 claims description 5
• 239000000356 contaminant Substances 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 5
• 229930195733 hydrocarbon Natural products 0.000 claims description 5
• HORBOHJHQGXXOR-UHFFFAOYSA-N n-octadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCCC HORBOHJHQGXXOR-UHFFFAOYSA-N 0.000 claims description 5
• 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
• 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
• 238000004383 yellowing Methods 0.000 claims description 5
• 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 4
• 239000005977 Ethylene Substances 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
• 150000001768 cations Chemical class 0.000 claims description 4
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 4
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
• 125000003838 furazanyl group Chemical group 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• FBJWIRNTQZKOLG-UHFFFAOYSA-N n-octadecyl-n-prop-2-enoxyoctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(OCC=C)CCCCCCCCCCCCCCCCCC FBJWIRNTQZKOLG-UHFFFAOYSA-N 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
• 230000003647 oxidation Effects 0.000 claims description 4
• 238000007254 oxidation reaction Methods 0.000 claims description 4
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
• 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 4
• 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 4
• 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 4
• 125000005561 phenanthryl group Chemical group 0.000 claims description 4
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 4
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 4
• 125000005954 phenoxathiinyl group Chemical group 0.000 claims description 4
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 4
• 125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 4
• 229920002401 polyacrylamide Polymers 0.000 claims description 4
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 4
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 claims description 4
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 4
• 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
• LANZFGLWXMOCID-UHFFFAOYSA-N 1-[[butyl-[(2-hydroxynaphthalen-1-yl)methyl]amino]methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CN(CC=3C4=CC=CC=C4C=CC=3O)CCCC)=C(O)C=CC2=C1 LANZFGLWXMOCID-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• HYWXXZKUIUIDJD-UHFFFAOYSA-N 2,4-ditert-butyl-6-(piperidin-1-ylmethyl)phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(CN2CCCCC2)=C1O HYWXXZKUIUIDJD-UHFFFAOYSA-N 0.000 claims description 3
• RZSKAFZKDDQPHN-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(dibutylamino)methyl]phenol Chemical compound CCCCN(CCCC)CC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O RZSKAFZKDDQPHN-UHFFFAOYSA-N 0.000 claims description 3
• GDVZBXWQGNQDCW-UHFFFAOYSA-N 2,4-ditert-butyl-6-[dimethylamino(phenyl)methyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(N(C)C)C1=CC=CC=C1 GDVZBXWQGNQDCW-UHFFFAOYSA-N 0.000 claims description 3
• ODPQEIZISSLBMQ-UHFFFAOYSA-N 2,4-ditert-butyl-6-[phenyl(piperidin-1-yl)methyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C(N2CCCCC2)C=2C=CC=CC=2)=C1O ODPQEIZISSLBMQ-UHFFFAOYSA-N 0.000 claims description 3
• CKEXYVSMAAJUCU-UHFFFAOYSA-N 2,6-ditert-butyl-4-[phenyl(piperidin-1-yl)methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(N2CCCCC2)C=2C=CC=CC=2)=C1 CKEXYVSMAAJUCU-UHFFFAOYSA-N 0.000 claims description 3
• LHYYOWUBDGZMDK-UHFFFAOYSA-N 2-methyl-4,6-bis(octadecylsulfanylmethyl)phenol Chemical compound CCCCCCCCCCCCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCCCCCCCCCCCC)=C1 LHYYOWUBDGZMDK-UHFFFAOYSA-N 0.000 claims description 3
• LLIYAFSMVQLZQF-UHFFFAOYSA-N 4-[2-[3,5-bis[(dimethylamino)methyl]-4-hydroxyphenyl]propan-2-yl]-2,6-bis[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=C(O)C(CN(C)C)=CC(C(C)(C)C=2C=C(CN(C)C)C(O)=C(CN(C)C)C=2)=C1 LLIYAFSMVQLZQF-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
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
• 150000001298 alcohols Chemical class 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 3
• 239000003086 colorant Substances 0.000 claims description 3
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
• 150000002443 hydroxylamines Chemical class 0.000 claims description 3
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
• GGDPATXHAYEICY-UHFFFAOYSA-N methyl 3-[3-tert-butyl-4-hydroxy-5-[phenyl(piperidin-1-yl)methyl]phenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(C(N2CCCCC2)C=2C=CC=CC=2)=C1O GGDPATXHAYEICY-UHFFFAOYSA-N 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000005493 quinolyl group Chemical group 0.000 claims description 3
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
• 238000005809 transesterification reaction Methods 0.000 claims description 3
• UFBJRCJIWUSVOX-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(cyclohexylamino)methyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(CNC2CCCCC2)=C1O UFBJRCJIWUSVOX-UHFFFAOYSA-N 0.000 claims description 2
• WHXDWNUJDBOXTD-UHFFFAOYSA-N 2,6-ditert-butyl-3-methyl-4-piperidin-1-ylphenol Chemical compound C1=C(C(C)(C)C)C(O)=C(C(C)(C)C)C(C)=C1N1CCCCC1 WHXDWNUJDBOXTD-UHFFFAOYSA-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
• REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 2
• 229950011260 betanaphthol Drugs 0.000 claims description 2
• 230000032050 esterification Effects 0.000 claims description 2
• 238000005886 esterification reaction Methods 0.000 claims description 2
• SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 2
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract description 196
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 24
• 238000001125 extrusion Methods 0.000 abstract description 21
• 235000013305 food Nutrition 0.000 abstract description 9
• 235000013361 beverage Nutrition 0.000 abstract description 3
• 239000000463 material Substances 0.000 abstract description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 71
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
• 239000000654 additive Substances 0.000 description 37
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 33
• 239000000243 solution Substances 0.000 description 31
• 239000010408 film Substances 0.000 description 30
• 239000000047 product Substances 0.000 description 29
• 230000009467 reduction Effects 0.000 description 29
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 26
• 150000001299 aldehydes Chemical class 0.000 description 26
• 239000002585 base Substances 0.000 description 25
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 20
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 19
• 150000003254 radicals Chemical class 0.000 description 18
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 16
• 239000010410 layer Substances 0.000 description 16
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 16
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
• 230000006641 stabilisation Effects 0.000 description 15
• 238000011105 stabilization Methods 0.000 description 15
• 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 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
• 238000005160 1H NMR spectroscopy Methods 0.000 description 13
• 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 12
• 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 12
• 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 12
• 239000007983 Tris buffer Substances 0.000 description 12
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