JP2005501140A - ポリアミン及びそれを用いて製造された重合体 - Google Patents
ポリアミン及びそれを用いて製造された重合体 Download PDFInfo
- Publication number
- JP2005501140A JP2005501140A JP2003523198A JP2003523198A JP2005501140A JP 2005501140 A JP2005501140 A JP 2005501140A JP 2003523198 A JP2003523198 A JP 2003523198A JP 2003523198 A JP2003523198 A JP 2003523198A JP 2005501140 A JP2005501140 A JP 2005501140A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- acid
- polyamine
- salt
- nylon
- 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.)
- Pending
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 153
- 229920000768 polyamine Polymers 0.000 title claims abstract description 43
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000002253 acid Substances 0.000 claims abstract description 28
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 74
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 19
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 16
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 16
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 10
- 235000011037 adipic acid Nutrition 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 239000001361 adipic acid Substances 0.000 claims description 7
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 5
- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 claims description 5
- 229940005657 pyrophosphoric acid Drugs 0.000 claims description 5
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 claims description 3
- JGJWEXOAAXEJMW-UHFFFAOYSA-N dimethyl naphthalene-1,2-dicarboxylate Chemical compound C1=CC=CC2=C(C(=O)OC)C(C(=O)OC)=CC=C21 JGJWEXOAAXEJMW-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 abstract description 28
- 239000000126 substance Substances 0.000 abstract description 8
- 239000000654 additive Substances 0.000 description 71
- 229920000728 polyester Polymers 0.000 description 59
- 230000000996 additive effect Effects 0.000 description 57
- 239000000835 fiber Substances 0.000 description 40
- 229920001778 nylon Polymers 0.000 description 39
- 239000004677 Nylon Substances 0.000 description 34
- -1 nitrogen-containing compound Chemical class 0.000 description 20
- 239000010408 film Substances 0.000 description 16
- 150000003512 tertiary amines Chemical group 0.000 description 16
- 239000004744 fabric Substances 0.000 description 11
- 239000004952 Polyamide Substances 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- 239000000980 acid dye Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229920001634 Copolyester Polymers 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 description 8
- 239000005020 polyethylene terephthalate Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229920002302 Nylon 6,6 Polymers 0.000 description 7
- 229960000250 adipic acid Drugs 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229920002292 Nylon 6 Polymers 0.000 description 6
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- RRKCJFKGMOIPIX-UHFFFAOYSA-N 4-[4-[3-cyanopropyl(methyl)amino]butyl-methylamino]butanenitrile Chemical compound N#CCCCN(C)CCCCN(C)CCCC#N RRKCJFKGMOIPIX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 125000004193 piperazinyl group Chemical group 0.000 description 3
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 229920003189 Nylon 4,6 Polymers 0.000 description 2
- 229920000305 Nylon 6,10 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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003086 colorant Substances 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
- 239000002270 dispersing agent Substances 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920000874 polytetramethylene terephthalate Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000002904 solvent Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-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
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-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
- CQPGDDAKTTWVDD-UHFFFAOYSA-N 4-bromobutanenitrile Chemical compound BrCCCC#N CQPGDDAKTTWVDD-UHFFFAOYSA-N 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- 102100025991 Betaine-homocysteine S-methyltransferase 1 Human genes 0.000 description 1
- 0 CC(C)N*(C)(C)*=O Chemical compound CC(C)N*(C)(C)*=O 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 101000933413 Homo sapiens Betaine-homocysteine S-methyltransferase 1 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 239000005083 Zinc sulfide Substances 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
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product 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
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 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
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000002009 diols Chemical class 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
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- CZPRYVBLOUZRGD-UHFFFAOYSA-N n,n'-dimethylbutane-1,4-diamine Chemical compound CNCCCCNC CZPRYVBLOUZRGD-UHFFFAOYSA-N 0.000 description 1
- 125000005487 naphthalate group Chemical group 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
- 125000004957 naphthylene group Chemical group 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
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Chemical group 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229920006126 semicrystalline polymer Polymers 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
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000005891 transamination reaction Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/14—Amines containing amino groups bound to at least two aminoalkyl groups, e.g. diethylenetriamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Artificial Filaments (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyamides (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/938,696 US6713653B2 (en) | 2001-08-24 | 2001-08-24 | Polyamines and polymers made therewith |
| PCT/US2002/026875 WO2003018533A2 (en) | 2001-08-24 | 2002-08-23 | Polyamines and polymers made therewith |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005501140A true JP2005501140A (ja) | 2005-01-13 |
| JP2005501140A5 JP2005501140A5 (https=) | 2006-01-05 |
Family
ID=25471816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003523198A Pending JP2005501140A (ja) | 2001-08-24 | 2002-08-23 | ポリアミン及びそれを用いて製造された重合体 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6713653B2 (https=) |
| EP (1) | EP1419136B1 (https=) |
| JP (1) | JP2005501140A (https=) |
| AT (1) | ATE403640T1 (https=) |
| AU (1) | AU2002331700A1 (https=) |
| CA (1) | CA2451013A1 (https=) |
| DE (1) | DE60228095D1 (https=) |
| ES (1) | ES2309198T3 (https=) |
| WO (1) | WO2003018533A2 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL146126A0 (en) * | 1999-04-30 | 2002-07-25 | Slil Biomedical Corp | Novel polyamine analog conjugates and quinone conjugates as therapies for cancers and prostate diseases |
| DE60029944T2 (de) * | 1999-04-30 | 2007-04-05 | Cellgate, Inc., Redwood City | Polyamine und ihre therapeutische verwendung |
| US7312244B2 (en) * | 1999-04-30 | 2007-12-25 | Cellgate, Inc. | Polyamine analog-amino acid conjugates useful as anticancer agents |
| US6723799B2 (en) * | 2001-08-24 | 2004-04-20 | E I. Du Pont De Nemours And Company | Acid-dyeable polymer compositions |
| US20030130356A1 (en) * | 2001-10-16 | 2003-07-10 | Slil Biomedical Corporation | Oligoamine compounds and derivatives thereof for cancer therapy |
| US7357985B2 (en) * | 2005-09-19 | 2008-04-15 | E.I. Du Pont De Nemours And Company | High crimp bicomponent fibers |
| US7666274B2 (en) * | 2006-08-01 | 2010-02-23 | International Paper Company | Durable paper |
| WO2009014857A1 (en) * | 2007-06-28 | 2009-01-29 | The Trustees Of The University Of Pennsylvania | Polyamide composites having flexible spacers |
Family Cites Families (22)
| 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 |
| US3553290A (en) | 1968-04-10 | 1971-01-05 | Du Pont | Spandex fibers stabilized with condensates of substituted phenols and divinyl benzenes |
| 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 |
| JPS5115866B2 (https=) | 1972-02-22 | 1976-05-20 | ||
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| JPH0819351B2 (ja) | 1988-06-09 | 1996-02-28 | サカタインクス株式会社 | 顔料分散剤及びそれを用いたオフセット印刷インキ組成物 |
| 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. |
| JPH05105754A (ja) | 1991-08-30 | 1993-04-27 | Yoshio Imai | 芳香族ポリアミド |
| JP3294385B2 (ja) | 1993-07-06 | 2002-06-24 | 帝人株式会社 | 改質ポリエステルの製造方法 |
| US5393849A (en) | 1993-10-19 | 1995-02-28 | Georgia-Pacific Resins, Inc. | Curable polyester/polyamino compositions |
| US6331262B1 (en) * | 1998-10-02 | 2001-12-18 | University Of Kentucky Research Foundation | Method of solubilizing shortened single-walled carbon nanotubes in organic solutions |
| US6331264B1 (en) | 1999-03-31 | 2001-12-18 | E. I. Du Pont De Nemours And Company | Low emission polymer compositions |
| US6277289B1 (en) | 1999-07-01 | 2001-08-21 | E. I. Du Pont De Nemours And Company | Treatment of aqueous aldehyde waste streams |
| DE19947716A1 (de) | 1999-10-05 | 2001-06-28 | Int Ges Fuer Elektrophysiologi | Verfahren und Gerät zur qualitativen und quantitativen Bewertung von Akupunkturpunkten |
| US6576340B1 (en) | 1999-11-12 | 2003-06-10 | E. I. Du Pont De Nemours And Company | Acid dyeable polyester compositions |
-
2001
- 2001-08-24 US US09/938,696 patent/US6713653B2/en not_active Expired - Fee Related
-
2002
- 2002-08-23 JP JP2003523198A patent/JP2005501140A/ja active Pending
- 2002-08-23 AT AT02768680T patent/ATE403640T1/de not_active IP Right Cessation
- 2002-08-23 AU AU2002331700A patent/AU2002331700A1/en not_active Abandoned
- 2002-08-23 WO PCT/US2002/026875 patent/WO2003018533A2/en not_active Ceased
- 2002-08-23 EP EP02768680A patent/EP1419136B1/en not_active Expired - Lifetime
- 2002-08-23 CA CA002451013A patent/CA2451013A1/en not_active Abandoned
- 2002-08-23 ES ES02768680T patent/ES2309198T3/es not_active Expired - Lifetime
- 2002-08-23 DE DE60228095T patent/DE60228095D1/de not_active Expired - Lifetime
-
2003
- 2003-06-06 US US10/455,883 patent/US6812325B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2309198T3 (es) | 2008-12-16 |
| ATE403640T1 (de) | 2008-08-15 |
| EP1419136A2 (en) | 2004-05-19 |
| US20030208031A1 (en) | 2003-11-06 |
| US20030045674A1 (en) | 2003-03-06 |
| HK1064083A1 (en) | 2005-01-21 |
| US6812325B2 (en) | 2004-11-02 |
| WO2003018533A2 (en) | 2003-03-06 |
| CA2451013A1 (en) | 2003-03-06 |
| AU2002331700A1 (en) | 2003-03-10 |
| US6713653B2 (en) | 2004-03-30 |
| WO2003018533A3 (en) | 2003-07-24 |
| DE60228095D1 (de) | 2008-09-18 |
| EP1419136B1 (en) | 2008-08-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4279140B2 (ja) | 酸染色可能なポリマー組成物 | |
| KR100730276B1 (ko) | 산성 염색성 폴리에스테르 조성물 | |
| TW200533703A (en) | Composition stabilized with respect to light and/or heat | |
| CN103097434B (zh) | 生物基三元共聚物及其制备方法 | |
| US6812325B2 (en) | Polyamines and polymers made therewith | |
| US8058326B2 (en) | Fluorescent poly(alkylene terephthalate) compositions | |
| TWI222476B (en) | Process for manufacturing yarns, fibres and filaments | |
| WO1995033088A1 (en) | Polyhexamethyleneadipamide fiber and process for producing the fiber | |
| HK1064083B (en) | Polyamines and polymers made therewith |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050722 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050722 |
|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20060626 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20080131 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080208 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080508 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20080515 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080609 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20080616 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080708 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090210 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20090717 |