BRPI0613348A2 - método para aumentar o peso molecular de um polìmero, método para aumentar o peso molecular e prover ramificação num polìmero e polìmero - Google Patents
método para aumentar o peso molecular de um polìmero, método para aumentar o peso molecular e prover ramificação num polìmero e polìmero Download PDFInfo
- Publication number
- BRPI0613348A2 BRPI0613348A2 BRPI0613348-7A BRPI0613348A BRPI0613348A2 BR PI0613348 A2 BRPI0613348 A2 BR PI0613348A2 BR PI0613348 A BRPI0613348 A BR PI0613348A BR PI0613348 A2 BRPI0613348 A2 BR PI0613348A2
- Authority
- BR
- Brazil
- Prior art keywords
- polymer
- functionality
- diol
- aliphatic
- formula
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 229
- 238000000034 method Methods 0.000 title claims abstract description 64
- 150000002009 diols Chemical class 0.000 claims abstract description 91
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 80
- -1 bis amide diol Chemical class 0.000 claims abstract description 54
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000006482 condensation reaction Methods 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 54
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 26
- 229920005862 polyol Polymers 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 150000003077 polyols Chemical class 0.000 claims description 23
- 125000002723 alicyclic group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000003153 chemical reaction reagent Substances 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- 239000004952 Polyamide Substances 0.000 claims description 15
- 229920002647 polyamide Polymers 0.000 claims description 15
- 238000009835 boiling Methods 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 8
- 150000005690 diesters Chemical class 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 4
- 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 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- 235000010469 Glycine max Nutrition 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004420 diamide group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims 3
- 229930182470 glycoside Natural products 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- 239000001361 adipic acid Substances 0.000 claims 2
- 235000011037 adipic acid Nutrition 0.000 claims 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims 2
- 229920000570 polyether Polymers 0.000 claims 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 1
- 101001026556 Xenopus laevis Histone H1.0-B Proteins 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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 10
- 239000007787 solid Substances 0.000 description 9
- 229920001400 block copolymer Polymers 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 238000013019 agitation Methods 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 229910000410 antimony oxide Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000002902 bimodal effect Effects 0.000 description 3
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- VTEGNKILKBWMBC-UHFFFAOYSA-L calcium diacetate hydrochloride Chemical compound Cl.[Ca+2].CC([O-])=O.CC([O-])=O VTEGNKILKBWMBC-UHFFFAOYSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229940014772 dimethyl sebacate Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 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
- 210000003739 neck Anatomy 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000909 polytetrahydrofuran 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
- 238000007056 transamidation reaction Methods 0.000 description 2
- 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
- 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
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 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
- 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 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
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- QMKYBPDZANOJGF-UHFFFAOYSA-K benzene-1,3,5-tricarboxylate(3-) Chemical compound [O-]C(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-K 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- XQKKWWCELHKGKB-UHFFFAOYSA-L calcium acetate monohydrate Chemical compound O.[Ca+2].CC([O-])=O.CC([O-])=O XQKKWWCELHKGKB-UHFFFAOYSA-L 0.000 description 1
- 229940067460 calcium acetate monohydrate Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 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
- 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
- 229950010286 diolamine Drugs 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003999 initiator Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229940089513 pentadecalactone Drugs 0.000 description 1
- 238000005191 phase separation Methods 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
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920001279 poly(ester amides) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 125000001302 tertiary amino group 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
- 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 1
- 238000005292 vacuum distillation Methods 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 (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0613348A2 true BRPI0613348A2 (pt) | 2011-01-04 |
Family
ID=38459395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0613348-7A BRPI0613348A2 (pt) | 2005-06-16 | 2006-06-14 | método para aumentar o peso molecular de um polìmero, método para aumentar o peso molecular e prover ramificação num polìmero e polìmero |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8080617B2 (enExample) |
| EP (1) | EP1910444A2 (enExample) |
| JP (1) | JP5107908B2 (enExample) |
| CN (2) | CN101198640B (enExample) |
| BR (1) | BRPI0613348A2 (enExample) |
| WO (1) | WO2007099397A2 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080044274A (ko) * | 2005-09-08 | 2008-05-20 | 다우 글로벌 테크놀로지스 인크. | 폴리에스테르-아미드계 핫 멜트 접착제 |
| EP2137235A1 (en) * | 2007-03-14 | 2009-12-30 | Dow Global Technologies Inc. | Copolyesteramides with decreased perfection of the amide sequence |
| EP2155934A2 (en) | 2007-05-30 | 2010-02-24 | Dow Global Technologies Inc. | High-output solvent-based electrospinning |
| WO2009110472A1 (ja) * | 2008-03-04 | 2009-09-11 | 三井化学株式会社 | ポリエステル系樹脂、その製造方法およびその用途 |
| WO2009134824A2 (en) * | 2008-05-02 | 2009-11-05 | Dow Global Technologies Inc. | Copolymers with amorphous polyamide segments |
| WO2010019649A2 (en) * | 2008-08-13 | 2010-02-18 | Dow Global Technologies Inc. | Active polymer compositions |
| 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 |
| WO2010019650A1 (en) | 2008-08-13 | 2010-02-18 | Dow Global Technologies Inc. | Process for producing micron and submicron fibers and nonwoven webs by melt blowing |
| US20100041804A1 (en) * | 2008-08-13 | 2010-02-18 | Brands Gerrit J | Fabricating fibers |
| WO2010065350A1 (en) * | 2008-11-25 | 2010-06-10 | Dow Global Technologies Inc. | Extruding molecularly self-assembling organic polymers |
| US8268042B2 (en) * | 2008-11-25 | 2012-09-18 | Dow Global Technologies Llc | Polymer inorganic clay composites |
| BRPI0916073A2 (pt) | 2008-11-25 | 2015-11-10 | Dow Global Technologies Llc | compósito de carga com afinidade por ligação pi/polímero, processo para preparar um compósito de carga com afinidade por ligação pi/polímero, artigo, e processo para separar um gás de uma mistura gasosa |
| US8784988B2 (en) | 2008-11-25 | 2014-07-22 | Dow Global Technologies Llc | Polymer inorganic-particulate composite fibers |
| US20100129641A1 (en) * | 2008-11-25 | 2010-05-27 | Lopez Leonardo C | Polymer carbon composites |
| US8609751B2 (en) * | 2008-11-25 | 2013-12-17 | Dow Global Technologies Llc | Polymer microfiller composites |
| US8440297B2 (en) * | 2008-11-25 | 2013-05-14 | Dow Global Technologies Llc | Polymer organoclay composites |
| BR112012015306A2 (pt) * | 2009-12-22 | 2016-03-15 | Dow Global Technologies Llc | poli (bisoxalamida), processo para preparar uma poli (bisoxalamida) e artigo |
| CA2789563A1 (en) | 2010-02-12 | 2011-08-18 | Scott T. Matteucci | Metal organic framework filled polymer based membranes |
| JP2013519377A (ja) | 2010-02-12 | 2013-05-30 | ダウ グローバル テクノロジーズ エルエルシー | 食品梱包用途における自己集合性ポリマー膜 |
| CA2789627A1 (en) * | 2010-02-12 | 2011-08-18 | Scott T. Matteucci | Separation of acidic constituents by self assembling polymer membranes |
| 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 |
| US9108168B2 (en) * | 2010-12-20 | 2015-08-18 | Dow Global Technologies Llc | Crosslinked silane-modified molecularly self-assembling material |
| AU2011349383A1 (en) | 2010-12-20 | 2013-06-27 | Dow Global Technologies Llc | Reactive functional group-modified molecularly self-assembling material |
| WO2013043807A1 (en) | 2011-09-21 | 2013-03-28 | Dow Global Technologies Llc | Azide crosslinked and physically crosslinked polymers for membrane separation |
| US9169367B2 (en) | 2012-09-20 | 2015-10-27 | 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 |
| EA201791685A1 (ru) | 2015-01-27 | 2018-01-31 | Дау Глоубл Текнолоджиз Ллк | Отделение азота от газообразного углеводорода с использованием пиролизованной сульфированной макропористой ионообменной смолы |
| WO2016122843A2 (en) | 2015-01-27 | 2016-08-04 | Dow Global Technologies Llc | Separation of hydrocarbons using regenerable macroporous alkylene-bridged adsorbent |
| EP3743475A1 (en) | 2018-01-23 | 2020-12-02 | Eastman Chemical Company | Novel polyesteramides, processes for the preparation thereof, and polyesteramide compositions |
| 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 |
| JP2003510433A (ja) | 1999-09-30 | 2003-03-18 | イソティス エヌ．ブイ． | ポリ（エーテルエステルアミド）コポリマー及びポリ（エーテルエステルウレタン）コポリマー |
| AU4885002A (en) * | 2001-07-03 | 2003-01-09 | Rohm And Haas Company | Composition method of making and method of using adhesive composition |
| US20050234215A1 (en) | 2002-02-21 | 2005-10-20 | Gaymans Reinoud J | Segmented copoymer containing amide segments |
| EP1553122A1 (en) * | 2004-01-08 | 2005-07-13 | DSM IP Assets B.V. | Process for preparing a high molecular polycondensate |
| KR20080044274A (ko) | 2005-09-08 | 2008-05-20 | 다우 글로벌 테크놀로지스 인크. | 폴리에스테르-아미드계 핫 멜트 접착제 |
| JP2010518273A (ja) | 2007-02-14 | 2010-05-27 | ダウ グローバル テクノロジーズ インコーポレイティド | 無溶剤静電紡糸によるポリマーまたはオリゴマー繊維 |
| EP2137235A1 (en) | 2007-03-14 | 2009-12-30 | 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 |
| EP2155934A2 (en) | 2007-05-30 | 2010-02-24 | Dow Global Technologies Inc. | High-output solvent-based electrospinning |
| US8609751B2 (en) | 2008-11-25 | 2013-12-17 | Dow Global Technologies Llc | Polymer microfiller composites |
-
2006
- 2006-06-14 US US11/917,164 patent/US8080617B2/en not_active Expired - Fee Related
- 2006-06-14 EP EP06842395A patent/EP1910444A2/en not_active Withdrawn
- 2006-06-14 BR BRPI0613348-7A patent/BRPI0613348A2/pt not_active IP Right Cessation
- 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
- 2006-06-14 CN CN2011101124811A patent/CN102212192A/zh active Pending
- 2006-06-14 JP JP2008516456A patent/JP5107908B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101198640A (zh) | 2008-06-11 |
| WO2007099397A3 (en) | 2007-11-29 |
| JP5107908B2 (ja) | 2012-12-26 |
| CN102212192A (zh) | 2011-10-12 |
| WO2007099397A2 (en) | 2007-09-07 |
| EP1910444A2 (en) | 2008-04-16 |
| JP2008544012A (ja) | 2008-12-04 |
| US8080617B2 (en) | 2011-12-20 |
| US20080214743A1 (en) | 2008-09-04 |
| CN101198640B (zh) | 2012-05-16 |
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 | |
| Kricheldorf et al. | Polylactones, 22 ABA triblock copolymers of L‐lactide and poly (ethylene glycol) | |
| US8450447B2 (en) | Copolyesteramides with decreased perfection of the amide sequence | |
| Niesten et al. | Synthesis and properties of segmented copolymers having aramid units of uniform length | |
| EP1367080A1 (en) | Hyperbranched poly(hydroxycarboxylic acid) polymers | |
| CN113683763B (zh) | 一种半芳香族聚酯及其制备方法和应用 | |
| Stapert et al. | Environmentally degradable aliphatic poly (ester‐amide) s based on short, symmetrical and uniform bisamide‐diol blocks, 1. Synthesis and interchange reactions | |
| BRPI0617034A2 (pt) | 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 | |
| Yu et al. | Facile preparation of stereochemistry-controllable biobased poly (butylene maleate-co-butylene fumarate) unsaturated copolyesters: a chemoselective polymer platform for versatile functionalization via aza-Michael addition | |
| WO2016062578A1 (en) | A process for preparing polylysines | |
| BG61520B2 (bg) | Биоразграждащ се полимер и метод за получаването му | |
| ES2876266T5 (en) | Aliphatic-aromatic polyesters having an increased white level index | |
| CN111019126A (zh) | 一种聚酯酰胺及其制备方法 | |
| Han et al. | Preparation and characterization of high molecular weight poly (butylene succinate) | |
| Gong et al. | Biodegradable comb-dendritic tri-block copolymers consisting of poly (ethylene glycol) and poly (l-lactide): synthesis, characterizations, and regulation of surface morphology and cell responses | |
| ES2298189T3 (es) | Copolimero multibloque de polieter. | |
| AU603393B2 (en) | Elastomers | |
| NL2015266B1 (en) | Poly(alkylene furandicarboxylate)-comprising polyester. | |
| CN114195998A (zh) | 一种连续化缩聚制备高强度聚乙醇酸的工艺 | |
| JP2008214366A (ja) | 膜モジュールのシール材用注型ポリウレタン樹脂形成性組成物 | |
| CN104540917A (zh) | 生物可降解的无衬垫黏着胶带及标签 | |
| Bera et al. | Block/segmented polymers. A new method of synthesis of copoly (amide‐ester)‐ester polymer | |
| JPH09110971A (ja) | 脂肪族ポリエステル共重合体の製造法 | |
| Crisci et al. | Hydrophilic Poly (ether‐ester) s and Poly (ether‐ester‐amide) s Derived from Poly (ε‐caprolactone) and COCl Terminated PEG Macromers | |
| JPH0757801B2 (ja) | 新規ポリエ−テル・エステル・アミド・ブロック・コポリマ− |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE AS 5A E 6A ANUIDADES. |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: REFERENTE AO DESPACHO 8.6 PUBLICADO NA RPI 2161 DE 05/06/2012. |