ES2278068T3 - Composiciones de poliester y poliamida de bajo contenido de aldehido residual. - Google Patents
Composiciones de poliester y poliamida de bajo contenido de aldehido residual. Download PDFInfo
- Publication number
- ES2278068T3 ES2278068T3 ES02785142T ES02785142T ES2278068T3 ES 2278068 T3 ES2278068 T3 ES 2278068T3 ES 02785142 T ES02785142 T ES 02785142T ES 02785142 T ES02785142 T ES 02785142T ES 2278068 T3 ES2278068 T3 ES 2278068T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- substituted
- tert
- butyl
- polyester
- Prior art date
- 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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- 239000000203 mixture Substances 0.000 title claims abstract description 105
- 239000004952 Polyamide Substances 0.000 title claims abstract description 96
- 229920002647 polyamide Polymers 0.000 title claims abstract description 96
- 229920000728 polyester Polymers 0.000 title claims abstract description 46
- -1 poly(ethylene terephthalate) Polymers 0.000 claims abstract description 253
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims abstract description 49
- 239000003381 stabilizer Substances 0.000 claims abstract description 37
- 229920000139 polyethylene terephthalate Polymers 0.000 claims abstract description 24
- 239000005020 polyethylene terephthalate Substances 0.000 claims abstract description 24
- 239000000835 fiber Substances 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 118
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 66
- 229910052760 oxygen Inorganic materials 0.000 claims description 66
- 239000001301 oxygen Substances 0.000 claims description 66
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 61
- 229910052717 sulfur Inorganic materials 0.000 claims description 61
- 239000011593 sulfur Substances 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 150000002431 hydrogen Chemical group 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 230000015572 biosynthetic process Effects 0.000 claims description 34
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 33
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 25
- 230000000087 stabilizing effect Effects 0.000 claims description 25
- 238000007499 fusion processing Methods 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 239000000356 contaminant Substances 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 239000000975 dye Substances 0.000 claims description 19
- 150000005846 sugar alcohols Polymers 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 125000004423 acyloxy group Chemical group 0.000 claims description 16
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000000049 pigment Substances 0.000 claims description 16
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 15
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 229920001577 copolymer Polymers 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000001589 carboacyl group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 10
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000004957 naphthylene group Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 125000005605 benzo group Chemical group 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
- 230000004927 fusion Effects 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 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 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 6
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 6
- 238000010309 melting process Methods 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- AHKPOWNNARPEGT-UHFFFAOYSA-N (3,5-ditert-butyl-2-hydroxyphenyl)methyl acetate Chemical compound CC(=O)OCC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O AHKPOWNNARPEGT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 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
- 150000001768 cations Chemical class 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
- 150000004702 methyl esters Chemical class 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
- 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
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 4
- CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical compound C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 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
- 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 229950011260 betanaphthol Drugs 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 3
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000003838 furazanyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 3
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 229920002401 polyacrylamide Polymers 0.000 claims description 3
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 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
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 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
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- CNRSHHSNCNLJCU-UHFFFAOYSA-N 2,4-bis[(dimethylamino)methyl]-3-methylphenol Chemical compound CN(C)CC1=CC=C(O)C(CN(C)C)=C1C CNRSHHSNCNLJCU-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
- 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 2
- 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 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 239000003760 tallow Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920006322 acrylamide copolymer Polymers 0.000 claims 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract description 204
- 238000001125 extrusion Methods 0.000 abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 26
- 235000013305 food Nutrition 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 235000013361 beverage Nutrition 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000654 additive Substances 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 33
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 30
- 230000009467 reduction Effects 0.000 description 30
- 239000002585 base Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- 150000001299 aldehydes Chemical class 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 150000003254 radicals Chemical group 0.000 description 23
- 239000010410 layer Substances 0.000 description 19
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-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
- 239000007787 solid Substances 0.000 description 12
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 229940059574 pentaerithrityl Drugs 0.000 description 9
- 239000000600 sorbitol Substances 0.000 description 9
- 235000010356 sorbitol Nutrition 0.000 description 9
- 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 8
- 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 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
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- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
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- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/02—Homopolymers or copolymers of unsaturated alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/24—Homopolymers or copolymers of amides or imides
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32794401P | 2001-10-09 | 2001-10-09 | |
| US327944P | 2001-10-09 | ||
| US33825301P | 2001-12-06 | 2001-12-06 | |
| US338253P | 2001-12-06 | ||
| US40015802P | 2002-08-01 | 2002-08-01 | |
| US400158P | 2002-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2278068T3 true ES2278068T3 (es) | 2007-08-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02785142T Expired - Lifetime ES2278068T3 (es) | 2001-10-09 | 2002-10-01 | Composiciones de poliester y poliamida de bajo contenido de aldehido residual. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20050176859A1 (enExample) |
| EP (1) | EP1440117B1 (enExample) |
| JP (1) | JP2005504868A (enExample) |
| AT (1) | ATE349488T1 (enExample) |
| AU (1) | AU2002350471A1 (enExample) |
| CA (1) | CA2466240A1 (enExample) |
| DE (1) | DE60217151T2 (enExample) |
| ES (1) | ES2278068T3 (enExample) |
| TW (1) | TWI303646B (enExample) |
| WO (1) | WO2003031507A2 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2454399C (en) * | 2001-08-13 | 2010-01-26 | Ciba Specialty Chemicals Holding Inc. | Polyester compositions of low residual aldehyde content |
| US20040043170A1 (en) * | 2002-06-24 | 2004-03-04 | The Procter & Gamble Company | Food package |
| WO2005040261A1 (en) * | 2003-10-15 | 2005-05-06 | Polyone Corporation | Use of tocopherol to scavenge acetaldehyde in polyethylene terephthalate containers |
| GB0406482D0 (en) * | 2004-03-23 | 2004-04-28 | Colormatrix Europe Ltd | Thermoplastic polymer additive compositions |
| CN102395557A (zh) * | 2008-12-09 | 2012-03-28 | 佛罗里达大学研究基金会公司 | 激酶抑制剂化合物 |
| CN102348761A (zh) | 2009-03-13 | 2012-02-08 | 巴斯夫欧洲公司 | 聚酯和聚酰胺的稳定共混物 |
| KR20120014889A (ko) * | 2009-03-13 | 2012-02-20 | 바스프 에스이 | 폴리에스테르 및 폴리아미드의 안정화된 블렌드 |
| JP5294943B2 (ja) * | 2009-03-30 | 2013-09-18 | シーシーアイ株式会社 | ソリッドタイヤの荷重判定方法 |
| US8779202B2 (en) | 2009-12-04 | 2014-07-15 | Georgetown University | Compositions and methods for the treatment of giardiasis |
| CN102875489B (zh) * | 2012-09-17 | 2015-09-30 | 浙江大学 | 2,6-二叔丁基-4-(苯基-1-哌啶基甲基)-苯酚的制备方法 |
| US9487619B2 (en) | 2014-10-27 | 2016-11-08 | Eastman Chemical Company | Carboxyl functional curable polyesters containing tetra-alkyl cyclobutanediol |
| US9598602B2 (en) * | 2014-11-13 | 2017-03-21 | Eastman Chemical Company | Thermosetting compositions based on phenolic resins and curable poleyester resins made with diketene or beta-ketoacetate containing compounds |
| US9650539B2 (en) | 2014-10-27 | 2017-05-16 | Eastman Chemical Company | Thermosetting compositions based on unsaturated polyesters and phenolic resins |
| US20160340471A1 (en) | 2015-05-19 | 2016-11-24 | Eastman Chemical Company | Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol |
| US20170088665A1 (en) | 2015-09-25 | 2017-03-30 | Eastman Chemical Company | POLYMERS CONTAINING CYCLOBUTANEDIOL AND 2,2 BIS(HYDROXYMETHYL) AlKYLCARBOXYLIC ACID |
| US9988553B2 (en) | 2016-02-22 | 2018-06-05 | Eastman Chemical Company | Thermosetting coating compositions |
| US10011737B2 (en) | 2016-03-23 | 2018-07-03 | Eastman Chemical Company | Curable polyester polyols and their use in thermosetting soft feel coating formulations |
| US11618244B2 (en) | 2017-10-26 | 2023-04-04 | Advansix Resins & Chemicals Llc | Multilayer package structure for ozone scavenging |
| CN109354571A (zh) * | 2018-09-29 | 2019-02-19 | 大连理工大学 | 回收再利用哌啶制备4-苯亚甲基-2,6-二叔丁基-2,5-环己二烯-1-酮的方法 |
| CN109735099A (zh) * | 2018-12-27 | 2019-05-10 | 会通新材料(上海)有限公司 | 一种改善耐光老化特性的聚酰胺56组合物及其应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL98864C (enExample) * | 1956-10-02 | |||
| ZA757702B (en) * | 1975-02-26 | 1976-11-24 | Grace W R & Co | Adjustable sealing device |
| DE2551634C3 (de) * | 1975-11-18 | 1980-07-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten |
| US4361681A (en) * | 1980-11-03 | 1982-11-30 | The Goodyear Tire & Rubber Company | Polyethylene terephthalate having a reduced acetaldehyde generation rate |
| EP0061210B1 (en) * | 1981-03-20 | 1985-01-16 | Akzo N.V. | Coloured polyethylene terephthalate moulding compound, a process for the preparation thereof and a container made therefrom |
| US4837115A (en) * | 1986-07-30 | 1989-06-06 | Toyo Seikan Kaisha, Ltd. | Thermoplastic polyester composition having improved flavor-retaining property and vessel formed therefrom |
| US4873279A (en) * | 1986-12-22 | 1989-10-10 | General Electric Company | Copolyester-carbonate and polyester resin blends exhibiting improved color properties |
| US5258233A (en) * | 1992-04-02 | 1993-11-02 | Eastman Kodak Company | Polyester/polyamide blend having improved flavor retaining property and clarity |
| US5266413A (en) * | 1992-05-18 | 1993-11-30 | Eastman Kodak Company | Copolyester/polyamide blend having improved flavor retaining property and clarity |
| KR940011606A (ko) * | 1992-11-05 | 1994-06-21 | 에른스트 알테르 | α,ω-알칸디페놀, 이를 함유하는 조성물 및 이들의 안정화제로서의 용도 |
| EP0691370A3 (en) * | 1994-07-07 | 1996-07-17 | Mitsubishi Chem Corp | Flame retardant polyester blend |
| US5459224A (en) * | 1994-07-18 | 1995-10-17 | Eastman Chemical Company | Copolyesters having improved weatherability |
| DE19503053B4 (de) * | 1995-02-01 | 2005-08-18 | Zimmer Ag | Verfahren zur direkten Herstellung von Polyester-Verpackungen |
| US5648032A (en) * | 1995-08-01 | 1997-07-15 | Eastman Chemical Company | Process for producing polyester articles having low acetaldehyde content |
| US5650469A (en) * | 1995-10-25 | 1997-07-22 | Eastman Chemical Company | Polyester/polyamide blend having improved flavor retaining property and clarity |
| DE19614067A1 (de) * | 1996-04-09 | 1997-10-16 | Hoechst Ag | Additivmischung mit nukleierender Wirkung für Kunststoffmassen |
| US6042908A (en) * | 1996-08-22 | 2000-03-28 | Eastman Chemical Company | Process for improving the flavor retaining property of polyester/polyamide blend containers for ozonated water |
| BR9911586A (pt) * | 1998-06-25 | 2001-03-20 | Ciba Sc Holding Ag | Processo para preparação de 3-aril-benzenofuranonas |
| GB9909956D0 (en) * | 1999-04-29 | 1999-06-30 | Univ Aston | Thermoplastic moulding compositions and polymer additives |
| ES2270855T3 (es) * | 1999-06-30 | 2007-04-16 | Ciba Specialty Chemicals Holding Inc. | Composiciones de poliester de bajo contenido de aldhehido residual. |
| US6274212B1 (en) * | 2000-02-22 | 2001-08-14 | The Coca-Cola Company | Method to decrease the acetaldehyde content of melt-processed polyesters |
-
2002
- 2002-10-01 EP EP02785142A patent/EP1440117B1/en not_active Expired - Lifetime
- 2002-10-01 AT AT02785142T patent/ATE349488T1/de active
- 2002-10-01 DE DE60217151T patent/DE60217151T2/de not_active Expired - Lifetime
- 2002-10-01 CA CA002466240A patent/CA2466240A1/en not_active Abandoned
- 2002-10-01 JP JP2003534486A patent/JP2005504868A/ja not_active Ceased
- 2002-10-01 US US10/491,598 patent/US20050176859A1/en not_active Abandoned
- 2002-10-01 WO PCT/EP2002/010995 patent/WO2003031507A2/en not_active Ceased
- 2002-10-01 ES ES02785142T patent/ES2278068T3/es not_active Expired - Lifetime
- 2002-10-01 AU AU2002350471A patent/AU2002350471A1/en not_active Abandoned
- 2002-10-07 TW TW091123048A patent/TWI303646B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003031507A3 (en) | 2003-12-11 |
| DE60217151D1 (de) | 2007-02-08 |
| TWI303646B (en) | 2008-12-01 |
| DE60217151T2 (de) | 2007-10-25 |
| EP1440117A2 (en) | 2004-07-28 |
| CA2466240A1 (en) | 2003-04-17 |
| WO2003031507A2 (en) | 2003-04-17 |
| US20050176859A1 (en) | 2005-08-11 |
| JP2005504868A (ja) | 2005-02-17 |
| EP1440117B1 (en) | 2006-12-27 |
| ATE349488T1 (de) | 2007-01-15 |
| AU2002350471A1 (en) | 2003-04-22 |
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