DE60027751T2 - Mit säuren färbbare polyesterzusammensetzungen - Google Patents
Mit säuren färbbare polyesterzusammensetzungen Download PDFInfo
- Publication number
- DE60027751T2 DE60027751T2 DE60027751T DE60027751T DE60027751T2 DE 60027751 T2 DE60027751 T2 DE 60027751T2 DE 60027751 T DE60027751 T DE 60027751T DE 60027751 T DE60027751 T DE 60027751T DE 60027751 T2 DE60027751 T2 DE 60027751T2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- polyester
- composition
- polyester composition
- polymeric additive
- 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
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 154
- 239000000203 mixture Substances 0.000 title claims abstract description 145
- 239000000654 additive Substances 0.000 claims abstract description 81
- 239000000835 fiber Substances 0.000 claims abstract description 79
- 230000000996 additive effect Effects 0.000 claims abstract description 76
- 239000002253 acid Substances 0.000 claims abstract description 56
- 229920000642 polymer Polymers 0.000 claims abstract description 51
- -1 secondary amine salt Chemical class 0.000 claims abstract description 40
- 229920002647 polyamide Polymers 0.000 claims abstract description 36
- 239000004952 Polyamide Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 26
- 238000004043 dyeing Methods 0.000 claims abstract description 20
- 239000000178 monomer Substances 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 11
- 229920002215 polytrimethylene terephthalate Polymers 0.000 claims description 43
- 150000003335 secondary amines Chemical group 0.000 claims description 39
- 229920001283 Polyalkylene terephthalate Polymers 0.000 claims description 30
- 229920001400 block copolymer Polymers 0.000 claims description 19
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- 229920001281 polyalkylene Polymers 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 claims description 5
- 125000005487 naphthalate group Chemical group 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 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
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 4
- 238000000465 moulding Methods 0.000 claims description 3
- 125000000879 imine group Chemical group 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 50
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 description 43
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 42
- 239000000975 dye Substances 0.000 description 25
- 229920001577 copolymer Polymers 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 18
- 238000009987 spinning Methods 0.000 description 15
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 239000000980 acid dye Substances 0.000 description 11
- 230000000704 physical effect Effects 0.000 description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 9
- 238000013329 compounding Methods 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- 229920001634 Copolyester Polymers 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 239000004753 textile Substances 0.000 description 6
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 238000010186 staining Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-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
- 239000006227 byproduct Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000002788 crimping Methods 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002074 melt spinning Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920000874 polytetramethylene terephthalate Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 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 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- NMYFVWYGKGVPIW-UHFFFAOYSA-N 3,7-dioxabicyclo[7.2.2]trideca-1(11),9,12-triene-2,8-dione Chemical compound O=C1OCCCOC(=O)C2=CC=C1C=C2 NMYFVWYGKGVPIW-UHFFFAOYSA-N 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000004234 Yellow 2G Substances 0.000 description 2
- LIKZXCROQGHXTI-UHFFFAOYSA-M acid blue 25 Chemical compound [Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC1=CC=CC=C1 LIKZXCROQGHXTI-UHFFFAOYSA-M 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 229960000250 adipic acid Drugs 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006085 branching agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- FTZLWXQKVFFWLY-UHFFFAOYSA-L disodium;2,5-dichloro-4-[3-methyl-5-oxo-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FTZLWXQKVFFWLY-UHFFFAOYSA-L 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 2
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 235000019235 yellow 2G Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical group CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- PGGROMGHWHXWJL-UHFFFAOYSA-N 4-(azepane-1-carbonyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)N1CCCCCC1 PGGROMGHWHXWJL-UHFFFAOYSA-N 0.000 description 1
- XEMMSXIXTJAXOT-UHFFFAOYSA-N 6-amino-5-[[2-[cyclohexyl(methyl)sulfamoyl]phenyl]diazenyl]-4-hydroxynaphthalene-2-sulfonic acid Chemical compound CN(C1CCCCC1)S(=O)(=O)C1=C(C=CC=C1)N=NC1=C(N)C=CC2=CC(=CC(O)=C12)S(O)(=O)=O XEMMSXIXTJAXOT-UHFFFAOYSA-N 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- QEIQEORTEYHSJH-UHFFFAOYSA-N Armin Natural products C1=CC(=O)OC2=C(O)C(OCC(CCO)C)=CC=C21 QEIQEORTEYHSJH-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- UMQAIKKJIZYHQC-UHFFFAOYSA-M Milling yellow 3G Chemical compound ClC=1C=CC(=C(C=1)S(=O)(=O)[O-])N1N=C(C(=C1O)N=NC1=CC=C(C=C1)OS(=O)(=O)C1=CC=C(C=C1)C)C.[Na+] UMQAIKKJIZYHQC-UHFFFAOYSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 229920013627 Sorona Polymers 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- ZXGIHDNEIWPDFW-UHFFFAOYSA-M acid red 4 Chemical compound [Na+].COC1=CC=CC=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ZXGIHDNEIWPDFW-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229920006125 amorphous polymer Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- WXLFIFHRGFOVCD-UHFFFAOYSA-L azophloxine Chemical compound [Na+].[Na+].OC1=C2C(NC(=O)C)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1 WXLFIFHRGFOVCD-UHFFFAOYSA-L 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 235000004879 dioscorea Nutrition 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- FPAYXBWMYIMERV-UHFFFAOYSA-L disodium;5-methyl-2-[[4-(4-methyl-2-sulfonatoanilino)-9,10-dioxoanthracen-1-yl]amino]benzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1S([O-])(=O)=O FPAYXBWMYIMERV-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 235000021189 garnishes Nutrition 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 210000001724 microfibril Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000007626 photothermal therapy Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000012739 red 2G Nutrition 0.000 description 1
- 239000004180 red 2G Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- MKWYFZFMAMBPQK-UHFFFAOYSA-J sodium feredetate Chemical compound [Na+].[Fe+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O MKWYFZFMAMBPQK-UHFFFAOYSA-J 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
-
- 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
- C08K5/17—Amines; Quaternary ammonium compounds
-
- 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
-
- 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
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2929—Bicomponent, conjugate, composite or collateral fibers or filaments [i.e., coextruded sheath-core or side-by-side type]
Landscapes
- 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)
- Artificial Filaments (AREA)
- Polyamides (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16537399P | 1999-11-12 | 1999-11-12 | |
| US165373P | 1999-11-12 | ||
| PCT/US2000/030772 WO2001034693A2 (en) | 1999-11-12 | 2000-11-09 | Acid dyeable polyester compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60027751D1 DE60027751D1 (de) | 2006-06-08 |
| DE60027751T2 true DE60027751T2 (de) | 2007-04-05 |
Family
ID=22598625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60027751T Expired - Lifetime DE60027751T2 (de) | 1999-11-12 | 2000-11-09 | Mit säuren färbbare polyesterzusammensetzungen |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US6576340B1 (https=) |
| EP (1) | EP1228132B1 (https=) |
| JP (1) | JP2003514092A (https=) |
| KR (1) | KR100730276B1 (https=) |
| CN (1) | CN1249141C (https=) |
| AT (1) | ATE325160T1 (https=) |
| BR (1) | BR0015470A (https=) |
| CA (1) | CA2386644A1 (https=) |
| DE (1) | DE60027751T2 (https=) |
| MX (1) | MXPA02004726A (https=) |
| WO (1) | WO2001034693A2 (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6287688B1 (en) * | 2000-03-03 | 2001-09-11 | E. I. Du Pont De Nemours And Company | Partially oriented poly(trimethylene terephthalate) yarn |
| WO2001066837A1 (en) | 2000-03-03 | 2001-09-13 | E.I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate) yarn |
| US6723799B2 (en) * | 2001-08-24 | 2004-04-20 | E I. Du Pont De Nemours And Company | Acid-dyeable polymer compositions |
| US6713653B2 (en) * | 2001-08-24 | 2004-03-30 | E. I. Du Pont De Nemours And Company | Polyamines and polymers made therewith |
| US6923925B2 (en) | 2002-06-27 | 2005-08-02 | E. I. Du Pont De Nemours And Company | Process of making poly (trimethylene dicarboxylate) fibers |
| US6921803B2 (en) | 2002-07-11 | 2005-07-26 | E.I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate) fibers, their manufacture and use |
| US6641916B1 (en) * | 2002-11-05 | 2003-11-04 | E. I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate) bicomponent fibers |
| US7578957B2 (en) * | 2002-12-30 | 2009-08-25 | E. I. Du Pont De Nemours And Company | Process of making staple fibers |
| US7005093B2 (en) * | 2003-02-05 | 2006-02-28 | E. I. Du Pont De Nemours And Company | Spin annealed poly(trimethylene terephthalate) yarn |
| US20050147784A1 (en) * | 2004-01-06 | 2005-07-07 | Chang Jing C. | Process for preparing poly(trimethylene terephthalate) fiber |
| US7785507B2 (en) | 2004-04-30 | 2010-08-31 | E. I. Du Pont De Nemours And Company | Spinning poly(trimethylene terephthalate) yarns |
| US20050272336A1 (en) * | 2004-06-04 | 2005-12-08 | Chang Jing C | Polymer compositions with antimicrobial properties |
| US7357985B2 (en) | 2005-09-19 | 2008-04-15 | E.I. Du Pont De Nemours And Company | High crimp bicomponent fibers |
| US8932706B2 (en) * | 2005-10-27 | 2015-01-13 | Multi-Color Corporation | Laminate with a heat-activatable expandable layer |
| EP1991515A4 (en) * | 2006-02-10 | 2013-03-06 | Dupont Tate & Lyle Bio Products Company Llc | BIOLOGICAL SOURCE AND ITS CONJUGATES AS NATURAL AND NON-BREATHING SOLVENTS FOR BIOMASS EXTRACTS, SCENT CONCENTRATES AND OILS |
| US7666274B2 (en) * | 2006-08-01 | 2010-02-23 | International Paper Company | Durable paper |
| US20080135662A1 (en) * | 2006-12-06 | 2008-06-12 | Chang Jing C | Melt-spun elastoester multifilament yarns |
| US20090214837A1 (en) * | 2008-02-21 | 2009-08-27 | Multi-Color Corporation | Insulating Label |
| US8987251B2 (en) | 2008-08-19 | 2015-03-24 | Array Biopharma Inc. | Triazolopyridine compounds as PIM kinase inhibitors |
| US8759430B1 (en) | 2010-06-02 | 2014-06-24 | Aquadye Fibers, Inc. | Acid dyed polyester (PET) or olefin yarns and textile fabrics using such yarns |
| CN101956278B (zh) * | 2010-08-19 | 2012-10-24 | 中国纺织科学研究院 | 一种改性聚酯和羊毛混纺织物及其制备方法 |
| WO2014108914A1 (en) * | 2013-01-08 | 2014-07-17 | Reliance Industries Limited | Polymeric composition and a method for preparation thereof |
| EP3914438B1 (en) * | 2019-01-23 | 2022-11-02 | Golden Lady Company S.p.A. | Method for dyeing a textile article made of modified polyester |
| EP4073301A1 (en) | 2019-12-10 | 2022-10-19 | DuPont Industrial Biosciences USA, LLC | Carpet made from self-bulking ptt-containing bicomponent fibers |
| MX2022013968A (es) | 2020-07-02 | 2022-11-30 | Dupont Ind Biosciences Usa Llc | Metodo para producir fibras bicomponentes y articulos que las comprenden. |
| CN113151928A (zh) * | 2021-06-09 | 2021-07-23 | 江苏鑫博高分子材料有限公司 | 一种聚酰胺/改性聚酯并列复合弹性纤维及其制备方法 |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1107267A (en) | 1963-09-23 | 1968-03-27 | Ici Ltd | Method of improving acid dyeability of fibre-forming polymers |
| US3397161A (en) | 1965-06-30 | 1968-08-13 | Dow Chemical Co | Resinous condensation products of aminopolyamides and halomethyldiphenyl ether |
| GB1281547A (en) * | 1969-06-26 | 1972-07-12 | Ici Ltd | Dyeable polyesters |
| JPS4833421B1 (https=) * | 1970-03-10 | 1973-10-13 | ||
| JPS4841777B1 (https=) * | 1970-03-25 | 1973-12-08 | ||
| CA974340A (en) | 1970-06-25 | 1975-09-09 | Fiber Industries | Acid dyeable polyester |
| JPS4732184A (https=) | 1971-04-01 | 1972-11-14 | ||
| BE785964A (fr) | 1971-07-07 | 1973-01-08 | Monsanto Co | Derives condenses de polyalkylenepolyamines |
| BE789430A (fr) * | 1971-10-15 | 1973-03-29 | Inst Francais Du Petrole | Procede d'isomerisation des hydrocarbures satures a basse temperature |
| JPS5115866B2 (https=) | 1972-02-22 | 1976-05-20 | ||
| DE2341000A1 (de) | 1973-08-14 | 1975-07-03 | Vyzk Ustav Chem Vlaken | Verfahren zur herstellung von farbkonzentraten fuer die faerbung von geformten polyester-produkten |
| US4001189A (en) | 1973-09-17 | 1977-01-04 | E. I. Du Pont De Nemours And Company | Fibers of acid-dyeable polyester having tetramethylpiperidine groups attached through oxyalkalene linkages to ends of polymer chains |
| US3901853A (en) | 1973-09-17 | 1975-08-26 | Du Pont | Acid-dyeable fibers of polyester modified with a tetramethylpiperidine compound having two ester-forming groups |
| US4001190A (en) | 1973-09-17 | 1977-01-04 | E. I. Du Pont De Nemours And Company | Acid-dyeable fibers of polyester modified with tetramethylpiperidine polyether glycols |
| US3932126A (en) | 1973-10-05 | 1976-01-13 | Martin Processing Co., Inc. | Dyeing assistant composition containing organic amines and carboxylic acids for coloring polyester material with acid dyes |
| DE2430626A1 (de) | 1974-06-26 | 1976-01-15 | Hoechst Ag | Verfahren zur herstellung von gefaerbten mehrkomponentfaeden |
| US4145473A (en) | 1975-02-05 | 1979-03-20 | E. I. Du Pont De Nemours And Company | Antistatic filament having a polymeric sheath and a conductive polymeric core |
| US4167541A (en) | 1977-05-12 | 1979-09-11 | Fiber Industries, Inc. | Continuous carrierless dyeable polyesters |
| JPS57193534A (en) | 1981-04-28 | 1982-11-27 | Teijin Ltd | Crimp yarn |
| EP0095712B2 (en) | 1982-05-28 | 1993-06-23 | Asahi Kasei Kogyo Kabushiki Kaisha | Easily dyeable polyethylene terephtalate fibre and process for preparing the same |
| JPH0726008B2 (ja) | 1987-03-31 | 1995-03-22 | 住友化学工業株式会社 | 熱可塑性樹脂組成物の製造法 |
| EP0423504B1 (en) * | 1989-10-18 | 1994-07-06 | General Electric Company | Multilayered structures comprising polycarbonate layers and functionalized polyamide layer |
| FR2660316B1 (fr) | 1990-03-30 | 1994-03-11 | Rhone Poulenc Chimie | Copolyamides semi-aromatiques semi-cristallins obtenus a partir d'acide terephtalique et de melanges comprenant une alkylpentamethylenediamine et de l'hexamethylenediamine. |
| JP3215714B2 (ja) | 1992-04-21 | 2001-10-09 | 株式会社クラレ | 易染性ポリエステル繊維 |
| DE69332819T2 (de) * | 1992-08-28 | 2003-11-13 | Idemitsu Kosan Co | Ladungsinjektionshilfe und sie enhaltende organische elektrolumineszente vorrichtung. |
| JP3295088B2 (ja) * | 1993-09-29 | 2002-06-24 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
| US5393849A (en) | 1993-10-19 | 1995-02-28 | Georgia-Pacific Resins, Inc. | Curable polyester/polyamino compositions |
| CA2183736C (en) | 1994-02-21 | 2001-07-31 | Peter Hirt | Process for dyeing polytrimethylene terephthalate fibres and use of thus dyed fibres |
| EP0681019B1 (en) * | 1994-04-26 | 1999-09-01 | TDK Corporation | Phenylanthracene derivative and organic EL element |
| TW288052B (https=) | 1994-06-30 | 1996-10-11 | Du Pont | |
| JPH0921060A (ja) | 1995-07-06 | 1997-01-21 | Toyobo Co Ltd | ポリエステル織物の製造方法 |
| US6001284A (en) * | 1995-08-04 | 1999-12-14 | Toyo Ink Manufacturing Co., Ltd. | Organoelectroluminescence device material and organoelectroluminescence device for which the material is adapted |
| EP1489206B1 (en) | 1997-08-18 | 2007-02-21 | Asahi Kasei Kabushiki Kaisha | Polyester fiber and fabric using the same |
| DE69828802T2 (de) | 1997-09-03 | 2005-12-22 | Asahi Kasei Kabushiki Kaisha | Polyesterfaser und gewebe daraus |
| JP3790024B2 (ja) | 1997-09-26 | 2006-06-28 | 旭化成せんい株式会社 | 易染性ポリエステル繊維 |
| JPH11172526A (ja) | 1997-11-26 | 1999-06-29 | Asahi Chem Ind Co Ltd | 低熱応力ポリエステル繊維及びその紡糸方法 |
| JP3836234B2 (ja) | 1997-12-02 | 2006-10-25 | 旭化成せんい株式会社 | ポリエステル樹脂組成物及びそれからなる繊維 |
| JP3073953B2 (ja) | 1997-12-26 | 2000-08-07 | 旭化成工業株式会社 | 発色性の優れた織編物 |
| US6140763A (en) * | 1998-07-28 | 2000-10-31 | Eastman Kodak Company | Interfacial electron-injecting layer formed from a doped cathode for organic light-emitting structure |
| JP3249107B2 (ja) | 1998-10-15 | 2002-01-21 | 旭化成株式会社 | ポリトリメチレンテレフタレート繊維 |
| US6680353B1 (en) | 1998-10-30 | 2004-01-20 | Asahi Kasei Kabushiki Kaisha | Polyester resin composition and fiber |
| KR100385783B1 (ko) | 1998-11-16 | 2003-06-02 | 아사히 가세이 가부시키가이샤 | 투웨이 경편지 |
| US6331264B1 (en) | 1999-03-31 | 2001-12-18 | E. I. Du Pont De Nemours And Company | Low emission polymer compositions |
| US6723799B2 (en) * | 2001-08-24 | 2004-04-20 | E I. Du Pont De Nemours And Company | Acid-dyeable polymer compositions |
-
2000
- 2000-11-08 US US09/708,209 patent/US6576340B1/en not_active Expired - Lifetime
- 2000-11-09 CN CNB008166765A patent/CN1249141C/zh not_active Expired - Fee Related
- 2000-11-09 MX MXPA02004726A patent/MXPA02004726A/es active IP Right Grant
- 2000-11-09 CA CA002386644A patent/CA2386644A1/en not_active Abandoned
- 2000-11-09 BR BR0015470-9A patent/BR0015470A/pt active Search and Examination
- 2000-11-09 KR KR1020027006033A patent/KR100730276B1/ko not_active Expired - Fee Related
- 2000-11-09 DE DE60027751T patent/DE60027751T2/de not_active Expired - Lifetime
- 2000-11-09 EP EP00979149A patent/EP1228132B1/en not_active Expired - Lifetime
- 2000-11-09 WO PCT/US2000/030772 patent/WO2001034693A2/en not_active Ceased
- 2000-11-09 JP JP2001537401A patent/JP2003514092A/ja active Pending
- 2000-11-09 AT AT00979149T patent/ATE325160T1/de not_active IP Right Cessation
-
2002
- 2002-03-07 US US10/093,654 patent/US6858702B2/en not_active Expired - Lifetime
- 2002-08-20 US US10/223,962 patent/US20030045651A1/en not_active Abandoned
-
2004
- 2004-08-24 US US10/925,102 patent/US7034088B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20030045651A1 (en) | 2003-03-06 |
| EP1228132B1 (en) | 2006-05-03 |
| ATE325160T1 (de) | 2006-06-15 |
| WO2001034693A3 (en) | 2001-11-22 |
| DE60027751D1 (de) | 2006-06-08 |
| JP2003514092A (ja) | 2003-04-15 |
| KR20020053847A (ko) | 2002-07-05 |
| US20020147298A1 (en) | 2002-10-10 |
| EP1228132A2 (en) | 2002-08-07 |
| WO2001034693A2 (en) | 2001-05-17 |
| CN1433446A (zh) | 2003-07-30 |
| BR0015470A (pt) | 2002-07-09 |
| US20050027049A1 (en) | 2005-02-03 |
| CA2386644A1 (en) | 2001-05-17 |
| US7034088B2 (en) | 2006-04-25 |
| US6858702B2 (en) | 2005-02-22 |
| KR100730276B1 (ko) | 2007-06-19 |
| CN1249141C (zh) | 2006-04-05 |
| MXPA02004726A (es) | 2003-01-28 |
| US6576340B1 (en) | 2003-06-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60027751T2 (de) | Mit säuren färbbare polyesterzusammensetzungen | |
| DE60223553T2 (de) | Mit säurefarbstoffen färbbare polymerzusammensetzungen | |
| DE60114566T2 (de) | Cationisches einfärbbarkeit-modifizierungsmittel zur verwendung mit polyestern und polyamiden | |
| DE2242002B2 (de) | Flammwidrige synthetische lineare polyester sowie deren verwendung | |
| DE2308572C3 (de) | Schmelzspinnbare Polyestermassen und deren Verwendung zur Herstellung von Fasern | |
| US6812325B2 (en) | Polyamines and polymers made therewith | |
| EP0991689B1 (de) | Fadenbildende kettenverzweigte polyester und copolyester | |
| DE2502642C3 (de) | Fäden und Fasern mit erhöhter Anfärbbarkeit und Verfahren zu deren Herstellung | |
| DE69828520T2 (de) | Verfahren zur Herstellung substituierter Polyamide | |
| DE2225282A1 (de) | Neue Zusammensetzungen auf der Basis von Polyestern mit guter Farbaffinität und Verfahren zu deren Herstellung | |
| DE102005037417A1 (de) | Verfahren zur Erhöhung des Molekulargewichts und zur gleichzeitigen Modifizierung von Polyestern und Polyamiden und deren Verwendung | |
| EP0658639A1 (de) | Multifilamentgarne für technische Einsatzgebiete aus Poly-(1,4-bis-methylencyclohexan-terephthalat) und Verfahren zu ihrer Herstellung | |
| DE1669490A1 (de) | Verfahren zur Herstellung von gemischten Faeden | |
| HK1064083B (en) | Polyamines and polymers made therewith | |
| DE2239466A1 (de) | Polyestermasse mit dauerhaften antistatischen eigenschaften |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |