JP5107908B2 - 脂肪族ポリエステルアミド組成物およびその製法 - Google Patents
脂肪族ポリエステルアミド組成物およびその製法 Download PDFInfo
- Publication number
- JP5107908B2 JP5107908B2 JP2008516456A JP2008516456A JP5107908B2 JP 5107908 B2 JP5107908 B2 JP 5107908B2 JP 2008516456 A JP2008516456 A JP 2008516456A JP 2008516456 A JP2008516456 A JP 2008516456A JP 5107908 B2 JP5107908 B2 JP 5107908B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- diol
- residue
- molecular weight
- dicarboxylic acid
- 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 - Fee Related
Links
- 125000001931 aliphatic group Chemical group 0.000 title claims description 61
- 238000000034 method Methods 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 title description 30
- 229920006149 polyester-amide block copolymer Polymers 0.000 title description 8
- 229920000642 polymer Polymers 0.000 claims description 142
- 150000002009 diols Chemical class 0.000 claims description 65
- -1 bisamide diol Chemical class 0.000 claims description 52
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 11
- 150000007519 polyprotic acids Polymers 0.000 claims description 10
- 229920005862 polyol Polymers 0.000 claims description 9
- 150000003077 polyols Chemical class 0.000 claims description 9
- 238000006482 condensation reaction Methods 0.000 claims description 8
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 44
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 21
- 239000002253 acid Substances 0.000 description 19
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 13
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 125000002723 alicyclic group Chemical group 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- 229920001400 block copolymer Polymers 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- KPVDACWQNCRKTG-UHFFFAOYSA-N aristolactam ii Chemical compound C=1C(C(=O)N2)=C3C2=CC2=CC=CC=C2C3=C2OCOC2=1 KPVDACWQNCRKTG-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 150000001408 amides Chemical group 0.000 description 3
- 229910000410 antimony oxide Inorganic materials 0.000 description 3
- 230000002902 bimodal effect Effects 0.000 description 3
- XQKKWWCELHKGKB-UHFFFAOYSA-L calcium acetate monohydrate Chemical compound O.[Ca+2].CC([O-])=O.CC([O-])=O XQKKWWCELHKGKB-UHFFFAOYSA-L 0.000 description 3
- 229940067460 calcium acetate monohydrate Drugs 0.000 description 3
- 238000000748 compression moulding Methods 0.000 description 3
- 229920006039 crystalline polyamide Polymers 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 229940014772 dimethyl sebacate Drugs 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- RGCHNYAILFZUPL-UHFFFAOYSA-N trimethyl benzene-1,3,5-tricarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(C(=O)OC)=C1 RGCHNYAILFZUPL-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
- RGCVYEOTYJCNOS-UHFFFAOYSA-N (4-cyano-2-methylphenyl)boronic acid Chemical compound CC1=CC(C#N)=CC=C1B(O)O RGCVYEOTYJCNOS-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- CFFICXVGSURQOO-UHFFFAOYSA-N 6-hydroxy-n-[2-(6-hydroxyhexanoylamino)ethyl]hexanamide Chemical compound OCCCCCC(=O)NCCNC(=O)CCCCCO CFFICXVGSURQOO-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- DRUKNYVQGHETPO-UHFFFAOYSA-N Nonanedioic acid dimethyl ester Natural products COC(=O)CCCCCCCC(=O)OC DRUKNYVQGHETPO-UHFFFAOYSA-N 0.000 description 1
- 241000746090 Passadena Species 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 101001026556 Xenopus laevis Histone H1.0-B Proteins 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid group Chemical group C(CCCCC(=O)O)(=O)O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N azelaic acid group Chemical group C(CCCCCCCC(=O)O)(=O)O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- QYMFNZIUDRQRSA-UHFFFAOYSA-N dimethyl butanedioate;dimethyl hexanedioate;dimethyl pentanedioate Chemical compound COC(=O)CCC(=O)OC.COC(=O)CCCC(=O)OC.COC(=O)CCCCC(=O)OC QYMFNZIUDRQRSA-UHFFFAOYSA-N 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid group Chemical group C(CCCC(=O)O)(=O)O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- JAUOHGIBLLRESW-UHFFFAOYSA-N methyl 6-[4-[(6-methoxy-6-oxohexanoyl)amino]butylamino]-6-oxohexanoate Chemical compound COC(=O)CCCCC(=O)NCCCCNC(=O)CCCCC(=O)OC JAUOHGIBLLRESW-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229940089513 pentadecalactone Drugs 0.000 description 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid group Chemical group C(CCCCCCCCC(=O)O)(=O)O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000004246 zinc acetate Substances 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
- C08G69/44—Polyester-amides
-
- 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
- C08G69/46—Post-polymerisation treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69097105P | 2005-06-16 | 2005-06-16 | |
| US60/690,971 | 2005-06-16 | ||
| PCT/IB2006/004005 WO2007099397A2 (en) | 2005-06-16 | 2006-06-14 | Aliphatic polyester-amide compositions and a process for producing the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008544012A JP2008544012A (ja) | 2008-12-04 |
| JP2008544012A5 JP2008544012A5 (https=) | 2009-07-09 |
| JP5107908B2 true JP5107908B2 (ja) | 2012-12-26 |
Family
ID=38459395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008516456A Expired - Fee Related JP5107908B2 (ja) | 2005-06-16 | 2006-06-14 | 脂肪族ポリエステルアミド組成物およびその製法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8080617B2 (https=) |
| EP (1) | EP1910444A2 (https=) |
| JP (1) | JP5107908B2 (https=) |
| CN (2) | CN102212192A (https=) |
| BR (1) | BRPI0613348A2 (https=) |
| WO (1) | WO2007099397A2 (https=) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0617034A2 (pt) * | 2005-09-08 | 2011-07-19 | Dow Global Technologies Inc | uso de um polìmero termoplástico de poliéster/amida numa formulação de adesivo hot melt, método para aplicar um adesivo hot melt, método para ligar um primeiro substrato a um segundo substrato, artigo tecido ou não tecido, caixa, caixa de papelão ou bandeja, livro, e melhoramento em artigo |
| WO2008112833A1 (en) * | 2007-03-14 | 2008-09-18 | Dow Global Technologies Inc. | Copolyesteramides with decreased perfection of the amide sequence |
| US8584871B2 (en) | 2007-05-30 | 2013-11-19 | Dow Global Technologies Llc | High-output solvent-based electrospinning |
| KR101284931B1 (ko) * | 2008-03-04 | 2013-07-10 | 미쓰이 가가쿠 가부시키가이샤 | 폴리에스터계 수지, 그의 제조방법 및 그의 용도 |
| WO2009134824A2 (en) * | 2008-05-02 | 2009-11-05 | Dow Global Technologies Inc. | Copolymers with amorphous polyamide segments |
| US8365925B2 (en) | 2008-08-13 | 2013-02-05 | Dow Global Technologies Llc | Filter medium |
| US20100041857A1 (en) * | 2008-08-13 | 2010-02-18 | Harris William J | Insitu synthesis of ester-amide-containing molecules |
| US8206484B2 (en) | 2008-08-13 | 2012-06-26 | Dow Global Technologies Llc | Process for producing micron and submicron fibers and nonwoven webs by melt blowing |
| US8524796B2 (en) | 2008-08-13 | 2013-09-03 | Dow Global Technologies Llc | Active polymer compositions |
| WO2010019647A2 (en) * | 2008-08-13 | 2010-02-18 | Dow Global Technologies Inc. | Fabricating fibers |
| US8784988B2 (en) | 2008-11-25 | 2014-07-22 | Dow Global Technologies Llc | Polymer inorganic-particulate composite fibers |
| US8609751B2 (en) * | 2008-11-25 | 2013-12-17 | Dow Global Technologies Llc | Polymer microfiller composites |
| US8268042B2 (en) * | 2008-11-25 | 2012-09-18 | Dow Global Technologies Llc | Polymer inorganic clay composites |
| US20100129641A1 (en) * | 2008-11-25 | 2010-05-27 | Lopez Leonardo C | Polymer carbon composites |
| CN102223943B (zh) * | 2008-11-25 | 2014-06-04 | 陶氏环球技术有限责任公司 | 聚合物亲π键填料复合材料 |
| US20100127434A1 (en) * | 2008-11-25 | 2010-05-27 | Rene Broos | Extruding organic polymers |
| US8440297B2 (en) * | 2008-11-25 | 2013-05-14 | Dow Global Technologies Llc | Polymer organoclay composites |
| EP2516507A1 (en) * | 2009-12-22 | 2012-10-31 | Dow Global Technologies LLC | Poly(bisoxalamides) |
| US20130133515A1 (en) * | 2010-02-12 | 2013-05-30 | Dow Global Technologies Llc | Separation of Acidic Constituents by Self Assembling Polymer Membranes |
| BR112012020071A2 (pt) | 2010-02-12 | 2015-09-01 | Dow Global Technologies Inc | Método para embalar um produto alimentício |
| CN103068474A (zh) | 2010-02-12 | 2013-04-24 | 陶氏环球技术有限责任公司 | 金属有机骨架填充的聚合物膜 |
| CN102234373A (zh) * | 2010-04-30 | 2011-11-09 | 北京化工大学 | 扩链制备可生物降解聚酯酰胺的方法 |
| CN102234372B (zh) * | 2010-04-30 | 2012-08-29 | 北京化工大学 | 嵌段可生物降解聚酰胺酯的制备方法 |
| CN103298853B (zh) | 2010-12-20 | 2015-06-24 | 陶氏环球技术有限责任公司 | 反应性官能团改性分子自组装材料 |
| CA2821731A1 (en) | 2010-12-20 | 2012-06-28 | Dow Global Technologies Llc | Crosslinked silane-modified molecularly self-assembling material |
| CN104220527B (zh) | 2011-09-21 | 2016-08-24 | 陶氏环球技术有限责任公司 | 用于膜分离的叠氮交联和物理交联的聚合物 |
| CA2884012C (en) | 2012-09-20 | 2020-09-01 | Dow Global Technologies Llc | Radiation cured membranes derived from polymers that are co-reactive with azide crosslinking agent(s) |
| US9371431B2 (en) | 2014-07-02 | 2016-06-21 | International Business Machines Corporation | Poly(ether sulfone)s and poly(ether amide sulfone)s and methods of their preparation |
| US9908079B2 (en) | 2015-01-27 | 2018-03-06 | Dow Global Technologies Llc | Separation of hydrocarbons using regenerable macroporous alkylene-bridged adsorbent |
| EA201791685A1 (ru) | 2015-01-27 | 2018-01-31 | Дау Глоубл Текнолоджиз Ллк | Отделение азота от газообразного углеводорода с использованием пиролизованной сульфированной макропористой ионообменной смолы |
| CN111630122B (zh) | 2018-01-23 | 2023-07-28 | 伊士曼化工公司 | 新型聚酯酰胺、其制备方法以及聚酯酰胺组合物 |
| US12331439B2 (en) | 2021-12-21 | 2025-06-17 | Uncaged Innovations Inc | Plant protein based imitation leather material and methods of making same |
| CN114752059B (zh) * | 2022-04-19 | 2023-06-16 | 西北大学 | 一种高分子量脂肪族聚酯酰胺的制备方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3025323A (en) * | 1957-01-18 | 1962-03-13 | Union Carbide Corp | Amide diols and their esters |
| GB1281752A (en) * | 1969-06-05 | 1972-07-12 | Ici Ltd | Unsaturated polyesteramides and their production |
| US4209607A (en) * | 1978-05-12 | 1980-06-24 | Ethicon, Inc. | Polyesteramides derived from bis-oxamidodiols and dicarboxylic acids |
| JPS62285920A (ja) * | 1986-06-04 | 1987-12-11 | Mitsui Petrochem Ind Ltd | 改質されたポリアミド系エラストマ−および製法 |
| DE19500757A1 (de) * | 1995-01-13 | 1996-07-18 | Basf Ag | Biologisch abbaubare Polymere, Verfahren zu deren Herstellung sowie deren Verwendung zur Herstellung bioabbaubarer Formkörper |
| US5962023A (en) * | 1995-03-06 | 1999-10-05 | Ethicon, Inc. | Hydrogels containing absorbable polyoxaamides |
| NL1003459C2 (nl) * | 1996-06-28 | 1998-01-07 | Univ Twente | Copoly(ester-amides) en copoly(ester-urethanen). |
| DE19800698A1 (de) * | 1998-01-10 | 1999-07-15 | Bayer Ag | Biologisch abbaubare Polyesteramide mit blockartig aufgebauten Polyester- und Polyamid-Segmenten |
| WO2001023457A1 (en) * | 1999-09-30 | 2001-04-05 | Iso Tis N.V. | Poly (ether ester amide) and poly (ether ester urethane) copolymers |
| AU4885002A (en) * | 2001-07-03 | 2003-01-09 | Rohm And Haas Company | Composition method of making and method of using adhesive composition |
| EP1476490A1 (en) | 2002-02-21 | 2004-11-17 | Universiteit Twente | Segmented copolymer containing amide segments |
| EP1553122A1 (en) * | 2004-01-08 | 2005-07-13 | DSM IP Assets B.V. | Process for preparing a high molecular polycondensate |
| BRPI0617034A2 (pt) * | 2005-09-08 | 2011-07-19 | Dow Global Technologies Inc | uso de um polìmero termoplástico de poliéster/amida numa formulação de adesivo hot melt, método para aplicar um adesivo hot melt, método para ligar um primeiro substrato a um segundo substrato, artigo tecido ou não tecido, caixa, caixa de papelão ou bandeja, livro, e melhoramento em artigo |
| US20100064647A1 (en) | 2007-02-14 | 2010-03-18 | Brands Gerrit J | Polymer or oligomer fibers by solvent-free electrospinning |
| WO2008112833A1 (en) | 2007-03-14 | 2008-09-18 | Dow Global Technologies Inc. | Copolyesteramides with decreased perfection of the amide sequence |
| US9150763B2 (en) | 2007-03-14 | 2015-10-06 | Dow Global Technologies Llc | Adhesive polymers for forming laminate structures |
| US8584871B2 (en) | 2007-05-30 | 2013-11-19 | Dow Global Technologies Llc | High-output solvent-based electrospinning |
| US8609751B2 (en) * | 2008-11-25 | 2013-12-17 | Dow Global Technologies Llc | Polymer microfiller composites |
-
2006
- 2006-06-14 BR BRPI0613348-7A patent/BRPI0613348A2/pt not_active IP Right Cessation
- 2006-06-14 EP EP06842395A patent/EP1910444A2/en not_active Withdrawn
- 2006-06-14 US US11/917,164 patent/US8080617B2/en not_active Expired - Fee Related
- 2006-06-14 CN CN2011101124811A patent/CN102212192A/zh active Pending
- 2006-06-14 JP JP2008516456A patent/JP5107908B2/ja not_active Expired - Fee Related
- 2006-06-14 WO PCT/IB2006/004005 patent/WO2007099397A2/en not_active Ceased
- 2006-06-14 CN CN200680021463XA patent/CN101198640B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101198640A (zh) | 2008-06-11 |
| CN102212192A (zh) | 2011-10-12 |
| BRPI0613348A2 (pt) | 2011-01-04 |
| US8080617B2 (en) | 2011-12-20 |
| US20080214743A1 (en) | 2008-09-04 |
| CN101198640B (zh) | 2012-05-16 |
| WO2007099397A2 (en) | 2007-09-07 |
| JP2008544012A (ja) | 2008-12-04 |
| WO2007099397A3 (en) | 2007-11-29 |
| EP1910444A2 (en) | 2008-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5107908B2 (ja) | 脂肪族ポリエステルアミド組成物およびその製法 | |
| US8450447B2 (en) | Copolyesteramides with decreased perfection of the amide sequence | |
| JP4009317B2 (ja) | 酵素的合成 | |
| US4864014A (en) | Polyester amides and polyether thioether ester amides and process for preparing them | |
| JP3241505B2 (ja) | 生分解性光学活性コポリマー及びその製造方法 | |
| US20100041857A1 (en) | Insitu synthesis of ester-amide-containing molecules | |
| CN111019126A (zh) | 一种聚酯酰胺及其制备方法 | |
| JP2001504545A (ja) | 改質１，３−プロパンジオールベースポリエステル | |
| CN102869698A (zh) | 由可再生资源制备的聚合物 | |
| JP4706808B2 (ja) | 脂肪族ポリエステルカーボネートの製造方法 | |
| JP3092233B2 (ja) | 液晶性ポリエステルアミド | |
| AU603393B2 (en) | Elastomers | |
| CN104540917A (zh) | 生物可降解的无衬垫黏着胶带及标签 | |
| EP1907438A2 (en) | N-hydroxyalkyltrimellitimide esters and bis-(trimellitimide) esters and method of making | |
| JP4784004B2 (ja) | 脂肪族ポリエステルカーボネートの製造方法 | |
| JP4431846B2 (ja) | 脂肪族ポリエステルの製造方法 | |
| Bera et al. | Block/segmented polymers. A new method of synthesis of copoly (amide‐ester)‐ester polymer | |
| JPH0621164B2 (ja) | ポリアミドエラストマ−の製法 | |
| JP2003002963A (ja) | 脂肪族ポリエステルの製造方法 | |
| US8269025B2 (en) | Purification of p-dioxanone | |
| JPS61247732A (ja) | ポリアミドエラストマ−の製造方法 | |
| Kricheldorf et al. | Polymers of carbonic acid—7. Synthesis and characterization of aliphatic polyallophanates | |
| JPH1135679A (ja) | 生分解性ポリラクトンエステルアミド及びその製造法 | |
| JPH0827269A (ja) | 生分解性ポリ（エステル−アミド）およびその製造方法 | |
| JPS63227613A (ja) | 低硬度ポリアミドエラストマ−の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090522 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20090522 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111115 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120210 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120904 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20121004 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20151012 Year of fee payment: 3 |
|
| LAPS | Cancellation because of no payment of annual fees |