DE69926518T2 - Neopentylglycol enthaltende polyester und daraus hergestellte fasern - Google Patents
Neopentylglycol enthaltende polyester und daraus hergestellte fasern Download PDFInfo
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- DE69926518T2 DE69926518T2 DE69926518T DE69926518T DE69926518T2 DE 69926518 T2 DE69926518 T2 DE 69926518T2 DE 69926518 T DE69926518 T DE 69926518T DE 69926518 T DE69926518 T DE 69926518T DE 69926518 T2 DE69926518 T2 DE 69926518T2
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- Germany
- Prior art keywords
- polyester
- fiber
- dicarboxylic acid
- component
- ppm
- 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.)
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- 229920000728 polyester Polymers 0.000 title claims description 175
- 239000000835 fiber Substances 0.000 title claims description 170
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 126
- 239000011230 binding agent Substances 0.000 claims description 78
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 74
- 239000000463 material Substances 0.000 claims description 52
- -1 amine compound Chemical class 0.000 claims description 43
- 230000003197 catalytic effect Effects 0.000 claims description 43
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 42
- 239000003054 catalyst Substances 0.000 claims description 40
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 38
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 30
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 16
- 229910052787 antimony Inorganic materials 0.000 claims description 13
- 229910052719 titanium Inorganic materials 0.000 claims description 13
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 12
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 12
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 12
- 150000008064 anhydrides Chemical class 0.000 claims description 10
- 239000000155 melt Substances 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 7
- 229920000098 polyolefin Polymers 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001414 amino alcohols Chemical class 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 5
- 150000003951 lactams Chemical class 0.000 claims description 5
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 5
- 229920001123 polycyclohexylenedimethylene terephthalate Polymers 0.000 claims description 5
- 229920002215 polytrimethylene terephthalate Polymers 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 4
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000002318 adhesion promoter Substances 0.000 claims description 2
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
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- 229920001634 Copolyester Polymers 0.000 description 39
- 238000000034 method Methods 0.000 description 26
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- 238000006243 chemical reaction Methods 0.000 description 24
- 229910017052 cobalt Inorganic materials 0.000 description 17
- 239000010941 cobalt Substances 0.000 description 17
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- 239000000047 product Substances 0.000 description 15
- 239000003086 colorant Substances 0.000 description 13
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- 239000004744 fabric Substances 0.000 description 11
- 239000011572 manganese Substances 0.000 description 11
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- 239000000654 additive Substances 0.000 description 9
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- 229910052748 manganese Inorganic materials 0.000 description 9
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 238000006068 polycondensation reaction Methods 0.000 description 8
- 239000002131 composite material Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 6
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
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- 229920006149 polyester-amide block copolymer Polymers 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- WWDKVICMJWBJKJ-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanol Chemical compound NCC1CCC(CO)CC1 WWDKVICMJWBJKJ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 229910052733 gallium Inorganic materials 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
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- 238000010924 continuous production Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 238000002074 melt spinning Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
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- 238000004458 analytical method Methods 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
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- 239000003795 chemical substances by application Substances 0.000 description 2
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
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- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- CHPZKNULDCNCBW-UHFFFAOYSA-N gallium nitrate Chemical compound [Ga+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CHPZKNULDCNCBW-UHFFFAOYSA-N 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 229940071125 manganese acetate Drugs 0.000 description 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
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- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
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- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 1
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 description 1
- GZZLQUBMUXEOBE-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diol Chemical compound OCCC(C)CC(C)(C)CO GZZLQUBMUXEOBE-UHFFFAOYSA-N 0.000 description 1
- WAXJSQREIWGYCB-UHFFFAOYSA-N 2-[4-(carboxymethyl)cyclohexyl]acetic acid Chemical compound OC(=O)CC1CCC(CC(O)=O)CC1 WAXJSQREIWGYCB-UHFFFAOYSA-N 0.000 description 1
- FOUQLSBYBRTDKN-UHFFFAOYSA-L 2-carboxyphenolate;cobalt(2+) Chemical compound [Co+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O FOUQLSBYBRTDKN-UHFFFAOYSA-L 0.000 description 1
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- MAOLOOKBPBABJE-UHFFFAOYSA-N 3-methylnonane-4,6-diol Chemical compound CCCC(O)CC(O)C(C)CC MAOLOOKBPBABJE-UHFFFAOYSA-N 0.000 description 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
- AHVVJFRSQDUYTL-UHFFFAOYSA-N 5,5-dimethylheptane-1,3-diol Chemical compound CCC(C)(C)CC(O)CCO AHVVJFRSQDUYTL-UHFFFAOYSA-N 0.000 description 1
- DQVNHMINOIEYOW-UHFFFAOYSA-N 5-ethylheptane-1,3-diol Chemical compound CCC(CC)CC(O)CCO DQVNHMINOIEYOW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
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- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical group OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 description 1
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- 238000010923 batch production Methods 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- UNRVMLDKEXPNDG-UHFFFAOYSA-N butanedioic acid;manganese Chemical compound [Mn].OC(=O)CCC(O)=O UNRVMLDKEXPNDG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
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- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- AJNVQOSZGJRYEI-UHFFFAOYSA-N digallium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Ga+3].[Ga+3] AJNVQOSZGJRYEI-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
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- 238000009472 formulation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229940044658 gallium nitrate Drugs 0.000 description 1
- 229910001195 gallium oxide Inorganic materials 0.000 description 1
- HZXMRANICFIONG-UHFFFAOYSA-N gallium phosphide Chemical compound [Ga]#P HZXMRANICFIONG-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
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- 229910052745 lead Inorganic materials 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- YIHQSMBNBPAEJC-UHFFFAOYSA-L manganese(2+);dibenzoate;tetrahydrate Chemical compound O.O.O.O.[Mn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YIHQSMBNBPAEJC-UHFFFAOYSA-L 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 239000002184 metal Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 238000010791 quenching Methods 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
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- 239000011541 reaction mixture Substances 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- JXJTWJYTKGINRZ-UHFFFAOYSA-J silicon(4+);tetraacetate Chemical compound [Si+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O JXJTWJYTKGINRZ-UHFFFAOYSA-J 0.000 description 1
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- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- VQNBUJAEBQLLKU-UHFFFAOYSA-H tricalcium;diphosphate;hydrate Chemical compound O.[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VQNBUJAEBQLLKU-UHFFFAOYSA-H 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910000634 wood's metal Inorganic materials 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- AGFGXVAAIXIOFZ-UHFFFAOYSA-L zinc;butanedioate Chemical compound [Zn+2].[O-]C(=O)CCC([O-])=O AGFGXVAAIXIOFZ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
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- D04H1/43825—Composite fibres
- D04H1/43832—Composite fibres side-by-side
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
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- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
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- D01F6/92—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyesters
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- D01F8/04—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers
- D01F8/14—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers with at least one polyester as constituent
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- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/42—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties characterised by the use of certain kinds of fibres insofar as this use has no preponderant influence on the consolidation of the fleece
- D04H1/4326—Condensation or reaction polymers
- D04H1/435—Polyesters
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- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/42—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties characterised by the use of certain kinds of fibres insofar as this use has no preponderant influence on the consolidation of the fleece
- D04H1/4382—Stretched reticular film fibres; Composite fibres; Mixed fibres; Ultrafine fibres; Fibres for artificial leather
- D04H1/43825—Composite fibres
- D04H1/43828—Composite fibres sheath-core
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- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
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- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/42—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties characterised by the use of certain kinds of fibres insofar as this use has no preponderant influence on the consolidation of the fleece
- D04H1/4382—Stretched reticular film fibres; Composite fibres; Mixed fibres; Ultrafine fibres; Fibres for artificial leather
- D04H1/43835—Mixed fibres, e.g. at least two chemically different fibres or fibre blends
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/02—Cellulose; Modified cellulose
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Mechanical Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Artificial Filaments (AREA)
- Multicomponent Fibers (AREA)
- Nonwoven Fabrics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyamides (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US143437 | 1998-08-28 | ||
| US09/143,437 US6197856B1 (en) | 1997-08-28 | 1998-08-28 | Copolymer binder fibers |
| US09/187,004 US6132868A (en) | 1997-11-06 | 1998-11-06 | Copolyester binder fibers |
| US187004 | 1998-11-06 | ||
| PCT/US1999/017828 WO2000012791A1 (en) | 1998-08-28 | 1999-08-06 | Polyesters containing neopentyl glycol and fibers formed therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69926518D1 DE69926518D1 (de) | 2005-09-08 |
| DE69926518T2 true DE69926518T2 (de) | 2006-01-05 |
Family
ID=26841030
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69926518T Expired - Fee Related DE69926518T2 (de) | 1998-08-28 | 1999-08-06 | Neopentylglycol enthaltende polyester und daraus hergestellte fasern |
| DE69921487T Expired - Fee Related DE69921487T2 (de) | 1998-08-28 | 1999-08-06 | Copolyester-binderfasern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69921487T Expired - Fee Related DE69921487T2 (de) | 1998-08-28 | 1999-08-06 | Copolyester-binderfasern |
Country Status (7)
| Country | Link |
|---|---|
| EP (2) | EP1108075B1 (enExample) |
| JP (2) | JP2002523646A (enExample) |
| CN (2) | CN1324415A (enExample) |
| BR (2) | BR9913205A (enExample) |
| DE (2) | DE69926518T2 (enExample) |
| MX (2) | MXPA01002107A (enExample) |
| WO (2) | WO2000012791A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6495656B1 (en) * | 1990-11-30 | 2002-12-17 | Eastman Chemical Company | Copolyesters and fibrous materials formed therefrom |
| US6497950B1 (en) | 1999-08-06 | 2002-12-24 | Eastman Chemical Company | Polyesters having a controlled melting point and fibers formed therefrom |
| US7994078B2 (en) | 2002-12-23 | 2011-08-09 | Kimberly-Clark Worldwide, Inc. | High strength nonwoven web from a biodegradable aliphatic polyester |
| US7892993B2 (en) * | 2003-06-19 | 2011-02-22 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
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| US20050148261A1 (en) * | 2003-12-30 | 2005-07-07 | Kimberly-Clark Worldwide, Inc. | Nonwoven webs having reduced lint and slough |
| CN100432118C (zh) * | 2006-03-22 | 2008-11-12 | 南昌大学 | 原位酯交换低聚乳酸合成可降解性芳香/脂肪共聚酯的方法 |
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| EP2677001A4 (en) | 2011-02-18 | 2016-10-19 | Midori Anzen Co Ltd | TRANSPARENT RESIN COMPOSITION WITH GOOD CHEMICAL RESISTANCE, DURABILITY AND STABILITY UNDER NATURAL AMBIENT CONDITIONS, IN MORE DIFFICULT NATURAL AMBIENT CONDITIONS, AND IN SIMILAR OR DIFFICULT CONDITIONS OF USE, AND PRODUCT USING THE SAME |
| JP5735844B2 (ja) * | 2011-04-07 | 2015-06-17 | 株式会社クラレ | 染色性に優れたカチオン可染ポリエステル繊維および繊維集合体 |
| CN104499084B (zh) * | 2014-12-31 | 2016-11-30 | 江苏恒力化纤股份有限公司 | 一种高上染率聚酯纤维fdy丝及其制备方法 |
| KR102471008B1 (ko) * | 2016-03-04 | 2022-11-24 | 도레이첨단소재 주식회사 | 안티몬 비용출 심초형 복합섬유 및 이를 포함하는 안티몬 비용출 트리코트 여과직물 |
| FR3063080B1 (fr) * | 2017-02-23 | 2021-04-30 | Bostik Sa | Composition comprenant un polyester et film adhesif activable a basse temperature |
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| EP3466385B1 (en) | 2017-10-06 | 2020-05-27 | The Procter & Gamble Company | Absorbent article or wipe comprising a nonwoven material with bicomponent fibers comprising antimony-free polyethylene terephthalate |
| CN109111587B (zh) * | 2018-08-20 | 2023-05-26 | 浙江汇锋智造科技有限公司 | 阻燃抗腐蚀环境工程用高分子膜材的制备方法及其装置 |
| TWI682945B (zh) | 2018-09-20 | 2020-01-21 | 遠東新世紀股份有限公司 | 用於製備低熔點共聚酯纖維的樹脂、低熔點共聚酯纖維及其製備方法 |
| WO2021011256A1 (en) * | 2019-07-15 | 2021-01-21 | Primaloft, Inc. | Recycled polyester binder fiber |
| JP7419540B2 (ja) * | 2019-12-27 | 2024-01-22 | トーレ・アドバンスド・マテリアルズ・コリア・インコーポレーテッド | 自動車内装材用繊維集合体及びこれを含む自動車内装材 |
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| TWI803790B (zh) * | 2020-11-24 | 2023-06-01 | 遠東新世紀股份有限公司 | 鞘芯型熱黏合纖維及不織布 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| BE592181A (enExample) * | 1955-12-22 | |||
| GB977104A (en) * | 1960-02-17 | 1964-12-02 | Hoechst Ag | Process for the manufacture of linear, aromatic fibre-forming polyesters |
| NL284670A (enExample) * | 1961-10-24 | |||
| GB1528601A (en) * | 1975-09-24 | 1978-10-18 | Ici Ltd | Preparation of linear polyesteramides |
| JPS6036565A (ja) * | 1983-08-09 | 1985-02-25 | Asahi Glass Co Ltd | 被覆用硬化性樹脂組成物 |
| JPS63203818A (ja) * | 1987-02-12 | 1988-08-23 | Nippon Ester Co Ltd | ホツトメルト型バインダ−繊維 |
| JPH055212A (ja) * | 1991-06-24 | 1993-01-14 | Toray Ind Inc | ポリエステル繊維の製法 |
| TW381104B (en) * | 1996-02-20 | 2000-02-01 | Eastman Chem Co | Process for preparing copolyesters of terephthalic acid, ethylene glycol, and 1,4-cyclohexanedimethanol |
| JP2001514336A (ja) * | 1997-08-28 | 2001-09-11 | イーストマン ケミカル カンパニー | 改良されたコポリマーバインダー繊維 |
| WO1999024648A1 (en) * | 1997-11-06 | 1999-05-20 | Eastman Chemical Company | Copolyester binder fibers |
-
1999
- 1999-08-06 WO PCT/US1999/017828 patent/WO2000012791A1/en not_active Ceased
- 1999-08-06 MX MXPA01002107A patent/MXPA01002107A/es unknown
- 1999-08-06 BR BR9913205-2A patent/BR9913205A/pt not_active IP Right Cessation
- 1999-08-06 WO PCT/US1999/017830 patent/WO2000012792A1/en not_active Ceased
- 1999-08-06 MX MXPA01001886A patent/MXPA01001886A/es unknown
- 1999-08-06 BR BR9913206-0A patent/BR9913206A/pt not_active Application Discontinuation
- 1999-08-06 EP EP19990939047 patent/EP1108075B1/en not_active Expired - Lifetime
- 1999-08-06 EP EP99940922A patent/EP1115925B1/en not_active Expired - Lifetime
- 1999-08-06 CN CN99812603A patent/CN1324415A/zh active Pending
- 1999-08-06 CN CNB998126012A patent/CN1167836C/zh not_active Expired - Fee Related
- 1999-08-06 DE DE69926518T patent/DE69926518T2/de not_active Expired - Fee Related
- 1999-08-06 DE DE69921487T patent/DE69921487T2/de not_active Expired - Fee Related
- 1999-08-06 JP JP2000567769A patent/JP2002523646A/ja active Pending
- 1999-08-06 JP JP2000567770A patent/JP2002523647A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE69926518D1 (de) | 2005-09-08 |
| BR9913206A (pt) | 2001-05-22 |
| EP1108075A1 (en) | 2001-06-20 |
| MXPA01002107A (es) | 2002-08-20 |
| DE69921487T2 (de) | 2005-02-24 |
| EP1115925A1 (en) | 2001-07-18 |
| JP2002523647A (ja) | 2002-07-30 |
| JP2002523646A (ja) | 2002-07-30 |
| EP1115925B1 (en) | 2005-08-03 |
| WO2000012791A1 (en) | 2000-03-09 |
| EP1108075B1 (en) | 2004-10-27 |
| BR9913205A (pt) | 2001-05-22 |
| CN1330735A (zh) | 2002-01-09 |
| MXPA01001886A (es) | 2002-04-24 |
| CN1167836C (zh) | 2004-09-22 |
| CN1324415A (zh) | 2001-11-28 |
| DE69921487D1 (de) | 2004-12-02 |
| WO2000012792A1 (en) | 2000-03-09 |
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