NO329458B1 - Fremgangsmate for fremstilling av bionedbrytbare alifatiske polyestere, og slike polyestere - Google Patents

Fremgangsmate for fremstilling av bionedbrytbare alifatiske polyestere, og slike polyestere Download PDF

Info

Publication number: NO329458B1
Authority: NO; Norway
Prior art keywords: acid; catalyst; mol; polyester; aliphatic
Prior art date: 1999-03-15

Application number

NO20014456A

Other languages

English (en)

Norwegian (no)

Other versions

NO20014456L (no

NO20014456D0 (no

Inventor

Marco Foa'

Fernanda Farachi

Tiziana Milizia

Original Assignee

Mini Ricerca Scient Tecnolog

Priority date (The priority date 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 date listed.)

1999-03-15

Filing date

2001-09-14

Publication date

2010-10-25

2001-09-14 Application filed by Mini Ricerca Scient Tecnolog filed Critical Mini Ricerca Scient Tecnolog

2001-09-14 Publication of NO20014456L publication Critical patent/NO20014456L/no

2001-09-14 Publication of NO20014456D0 publication Critical patent/NO20014456D0/no

2010-10-25 Publication of NO329458B1 publication Critical patent/NO329458B1/no

Links

229920003232 aliphatic polyester Polymers 0.000 title claims abstract description 16
238000000034 method Methods 0.000 title claims description 44
229920000728 polyester Polymers 0.000 title claims description 25
230000008569 process Effects 0.000 title claims description 13
-1 aliphatic dicarboxylic acids Chemical class 0.000 claims abstract description 26
239000002253 acid Substances 0.000 claims abstract description 15
150000005690 diesters Chemical class 0.000 claims abstract description 7
150000007513 acids Chemical class 0.000 claims abstract description 5
WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims abstract description 3
229960003656 ricinoleic acid Drugs 0.000 claims abstract description 3
FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims abstract description 3
239000003054 catalyst Substances 0.000 claims description 29
238000004519 manufacturing process Methods 0.000 claims description 15
230000032050 esterification Effects 0.000 claims description 14
238000005886 esterification reaction Methods 0.000 claims description 14
NPAIMXWXWPJRES-UHFFFAOYSA-N butyltin(3+) Chemical compound CCCC[Sn+3] NPAIMXWXWPJRES-UHFFFAOYSA-N 0.000 claims description 11
238000005809 transesterification reaction Methods 0.000 claims description 11
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 7
238000012360 testing method Methods 0.000 claims description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
239000003377 acid catalyst Substances 0.000 claims description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
KDMSVYIHKLZKET-UHFFFAOYSA-N 8-hydroxyoctanoic acid Chemical compound OCCCCCCCC(O)=O KDMSVYIHKLZKET-UHFFFAOYSA-N 0.000 claims description 4
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
239000000155 melt Substances 0.000 claims description 4
238000009264 composting Methods 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
VACHUYIREGFMSP-UHFFFAOYSA-N (+)-threo-9,10-Dihydroxy-octadecansaeure Natural products CCCCCCCCC(O)C(O)CCCCCCCC(O)=O VACHUYIREGFMSP-UHFFFAOYSA-N 0.000 claims description 2
JPFGKGZYCXLEGQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-5-methylpyrazole-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C(C)=C(C(O)=O)C=N1 JPFGKGZYCXLEGQ-UHFFFAOYSA-N 0.000 claims description 2
NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 claims description 2
JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 claims description 2
PNAJBOZYCFSQDJ-UHFFFAOYSA-N 7-hydroxyheptanoic acid Chemical compound OCCCCCCC(O)=O PNAJBOZYCFSQDJ-UHFFFAOYSA-N 0.000 claims description 2
VACHUYIREGFMSP-SJORKVTESA-N 9,10-Dihydroxystearic acid Natural products CCCCCCCC[C@@H](O)[C@@H](O)CCCCCCCC(O)=O VACHUYIREGFMSP-SJORKVTESA-N 0.000 claims description 2
UGUYQBMBIJFNRM-OQFOIZHKSA-N [(z)-but-2-en-2-yl]benzene Chemical compound C\C=C(\C)C1=CC=CC=C1 UGUYQBMBIJFNRM-OQFOIZHKSA-N 0.000 claims description 2
125000002015 acyclic group Chemical group 0.000 claims description 2
150000001261 hydroxy acids Chemical class 0.000 claims description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
239000004310 lactic acid Substances 0.000 claims description 2
235000014655 lactic acid Nutrition 0.000 claims description 2
229920001281 polyalkylene Polymers 0.000 claims description 2
SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims 1
229940116351 sebacate Drugs 0.000 claims 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims 1
229920001577 copolymer Polymers 0.000 abstract description 2
229920000642 polymer Polymers 0.000 description 24
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 16
229910052757 nitrogen Inorganic materials 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
238000006116 polymerization reaction Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 5
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
239000010408 film Substances 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
235000013410 fast food Nutrition 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000004970 Chain extender Substances 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
239000001639 calcium acetate Substances 0.000 description 2
235000011092 calcium acetate Nutrition 0.000 description 2
229960005147 calcium acetate Drugs 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000002131 composite material Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
150000001991 dicarboxylic acids Chemical class 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000011888 foil Substances 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
238000004806 packaging method and process Methods 0.000 description 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000002861 polymer material Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
239000004753 textile Substances 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical compound CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
FVHVHJZQCPCEQG-UHFFFAOYSA-N CCCCCC(O)O.CCCCC(O)CO Chemical compound CCCCCC(O)O.CCCCC(O)CO FVHVHJZQCPCEQG-UHFFFAOYSA-N 0.000 description 1
SVGSGCAXNRHRII-UHFFFAOYSA-K CCCC[Sn](O)(O)O Chemical compound CCCC[Sn](O)(O)O SVGSGCAXNRHRII-UHFFFAOYSA-K 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
229920001634 Copolyester Polymers 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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 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
125000005595 acetylacetonate group Chemical group 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229920000229 biodegradable polyester Polymers 0.000 description 1
239000004622 biodegradable polyester Substances 0.000 description 1
239000004621 biodegradable polymer Substances 0.000 description 1
229920002988 biodegradable polymer Polymers 0.000 description 1
238000006065 biodegradation reaction Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 1
FAOSYNUKPVJLNZ-UHFFFAOYSA-N butylstannane Chemical compound CCCC[SnH3] FAOSYNUKPVJLNZ-UHFFFAOYSA-N 0.000 description 1
LUZSPGQEISANPO-UHFFFAOYSA-N butyltin Chemical compound CCCC[Sn] LUZSPGQEISANPO-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
235000013351 cheese Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
238000007765 extrusion coating Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
235000012055 fruits and vegetables Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
230000036541 health Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000005259 measurement Methods 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
239000011104 metalized film Substances 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
239000010815 organic waste Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
238000010094 polymer processing Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
229920006300 shrink film Polymers 0.000 description 1
239000002356 single layer Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
229920006302 stretch film Polymers 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
DPUOLQHDNGRHBS-MDZDMXLPSA-N trans-Brassidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-MDZDMXLPSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
235000013618 yogurt Nutrition 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyesters Or Polycarbonates (AREA)
Biological Depolymerization Polymers (AREA)
Wrappers (AREA)
Manufacture Of Macromolecular Shaped Articles (AREA)
Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Compositions Of Macromolecular Compounds (AREA)
Artificial Filaments (AREA)

NO20014456A 1999-03-15 2001-09-14 Fremgangsmate for fremstilling av bionedbrytbare alifatiske polyestere, og slike polyestere NO329458B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT1999TO000198A IT1307022B1 (it)	1999-03-15	1999-03-15	Processo semplificato per l'ottenimento di poliesteri alifaticibiodegradabili.
PCT/EP2000/002305 WO2000055236A1 (en)	1999-03-15	2000-03-15	A simplified method of producing biodegradable aliphatic polyesters

Publications (3)

Publication Number	Publication Date
NO20014456L NO20014456L (no)	2001-09-14
NO20014456D0 NO20014456D0 (no)	2001-09-14
NO329458B1 true NO329458B1 (no)	2010-10-25

Family

ID=11417618

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20014456A NO329458B1 (no)	1999-03-15	2001-09-14	Fremgangsmate for fremstilling av bionedbrytbare alifatiske polyestere, og slike polyestere

Country Status (11)

Country	Link
US (1)	US6562939B1 (de)
EP (2)	EP1165650A1 (de)
JP (1)	JP2002539309A (de)
AT (1)	ATE375374T1 (de)
AU (1)	AU756070B2 (de)
CA (1)	CA2365485C (de)
DE (1)	DE60036737T2 (de)
ES (1)	ES2294428T3 (de)
IT (1)	IT1307022B1 (de)
NO (1)	NO329458B1 (de)
WO (1)	WO2000055236A1 (de)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ITTO20010058A1 (it)	2001-01-25	2002-07-25	Novamont Spa	Miscele ternarie di poliesteri biodegradabili e prodotti da queste ottenuti.
ITMI20020867A1 (it) *	2002-04-22	2003-10-22	Novamont Spa	Copoliesteri termoplastici saturi/insaturi biodegradabili
ITMI20020864A1 (it)	2002-04-22	2003-10-22	Novamont Spa	Copolimeri a blocchi amorfo-cristallini
ITMI20020866A1 (it) *	2002-04-22	2003-10-22	Novamont Spa	Copoliesteri termoplastici saturi/insaturi biodegradabili
ITMI20020865A1 (it) *	2002-04-22	2003-10-22	Novamont Spa	Poliesteri biodegradabili ottenuti mediante estrusione reattiva
US20060286138A1 (en) *	2003-04-10	2006-12-21	Malshe Vinod C	Novel biodegradable aliphatic polyesters and pharmaceutical compositions and applications thereof
JP4635475B2 (ja) *	2003-05-21	2011-02-23	三菱化学株式会社	脂肪族ポリエステル及びその製造方法
US20070082982A1 (en) *	2005-10-11	2007-04-12	The Procter & Gamble Company	Water stable compositions and articles comprising starch and methods of making the same
US9091004B2 (en) *	2006-07-14	2015-07-28	Kimberly-Clark Worldwide, Inc.	Biodegradable polylactic acid for use in nonwoven webs
EP2044251B1 (de) *	2006-07-14	2019-10-02	NatureWorks LLC	Biologisch abbaubarer aliphatischer polyester zur verwendung in vliesstoffen
MX2009000526A (es) *	2006-07-14	2009-01-27	Kimberly Clark Co	Copoliester alifatico-aromatico biodegradable para usarse en telas no tejidas.
US8729176B2 (en)	2006-09-06	2014-05-20	Keio University	Polyricinoleate composition and process for producing the same
EP2064261A1 (de) *	2006-12-15	2009-06-03	Kimberly-Clark Worldwide, Inc.	Biologisch abbaubare polymilchsäuren zur verwendung bei der bildung von fasern
WO2008073099A1 (en) *	2006-12-15	2008-06-19	Kimberly-Clark Worldwide, Inc.	Biodegradable polyesters for use in forming fibers
EP2109531B1 (de)	2007-02-14	2020-07-15	Netafim Ltd.	Biologisch abbaubare bewässerungsleitung
WO2009024836A1 (en) *	2007-08-22	2009-02-26	Kimberly-Clark Worldwide, Inc.	Multicomponent biodegradable filaments and nonwoven webs formed therefrom
US20100323575A1 (en) *	2007-12-13	2010-12-23	Aimin He	Biodegradable fibers formed from a thermoplastic composition containing polylactic acid and a polyether copolymer
KR101526636B1 (ko) *	2008-05-30	2015-06-05	킴벌리-클라크 월드와이드, 인크.	폴리락트산 섬유
US8461262B2 (en)	2010-12-07	2013-06-11	Kimberly-Clark Worldwide, Inc.	Polylactic acid fibers
IT1403272B1 (it) *	2010-12-20	2013-10-17	Novamont Spa	Strutture oligomeriche complesse
ITMI20121067A1 (it) *	2012-06-19	2013-12-20	Novamont Spa	Derivati vegetali come oli estensori e biofiller in composizioni elastomeriche.
KR20140031011A (ko) *	2012-09-04	2014-03-12	삼성정밀화학 주식회사	생분해성 지방족 폴리에스테르의 연속 제조방법
KR101992391B1 (ko) *	2012-09-04	2019-09-30	(주)새한폴리머	생분해성 지방족/방향족 폴리에스테르 공중합체의 연속 제조방법
CN103243413B (zh) *	2013-04-24	2014-11-05	浙江理工大学	一种可完全生物降解脂肪族共聚酯短纤维的制备方法
JP6538087B2 (ja) *	2014-05-30	2019-07-03	ザ・セカント・グループ・エルエルシー	ポリマー材料の水媒介製造
JP6619011B2 (ja) *	2015-08-31	2019-12-11	三井化学株式会社	共重合体および潤滑油組成物
EP3600465A1 (de)	2017-03-31	2020-02-05	The Secant Group, LLC	Gehärtete biologisch abbaubare mikropartikel sowie gerüste und verfahren zur herstellung und verwendung davon
US10822450B2 (en)	2017-07-11	2020-11-03	The Secant Group Llc	Poly(glycerol sebacate)-interleukin inhibitor copolymers and methods of making and use
KR102621249B1 (ko) *	2020-08-19	2024-01-08	효성티앤씨 주식회사	폴리에스터 원사 및 그의 제조방법
CN118996663B (zh) *	2024-09-26	2025-07-11	江苏轩达高分子材料有限公司	一种生物基聚酯记忆纤维及其制备方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS55142024A (en) *	1979-04-23	1980-11-06	Toray Ind Inc	Production of polyester
JPS6119628A (ja) *	1984-07-05	1986-01-28	Mitsubishi Kasei Vinyl Co	ポリエステルの製法
US4554343A (en)	1984-11-23	1985-11-19	Eastman Kodak Company	Process for the production of high molecular weight polyester
US4970288A (en)	1989-09-22	1990-11-13	Atochem North America, Inc.	Non-toxic polyester compositions made with organotin esterification catalysts
US5306787A (en)	1990-11-26	1994-04-26	Showa Highpolymer Co., Ltd.	Method for producing saturated polyester
US5166310A (en)	1991-08-27	1992-11-24	The Dow Chemical Company	Preparation of polyesters with tin catalyst
JP3179177B2 (ja)	1992-04-10	2001-06-25	昭和高分子株式会社	ウレタン結合を含む脂肪族ポリエステル
KR0120326B1 (ko)	1992-12-24	1997-10-22	김준웅	열가소성 생분해성 지방족 폴리에스테르 및 그 제조방법
US5401796A (en)	1993-04-02	1995-03-28	Mitsui Toatsu Chemicals, Inc.	Aliphatic polyester and preparation process thereof
EP0703260A1 (de)	1994-09-21	1996-03-27	Tonen Corporation	Aliphatischer Polyester und Verfahren zu seiner Herstellung
AU694832B2 (en) *	1994-12-21	1998-07-30	Showa Denko Kabushiki Kaisha	Aliphatic polyester resin and process for producing the same
JPH0959359A (ja) *	1995-06-13	1997-03-04	Toray Ind Inc	ポリエステル重合体およびその製造方法
JP3888693B2 (ja)	1995-10-13	2007-03-07	ユニ・チャーム株式会社	ウェットワイプス

1999
- 1999-03-15 IT IT1999TO000198A patent/IT1307022B1/it active
2000
- 2000-03-15 EP EP00910841A patent/EP1165650A1/de not_active Ceased
- 2000-03-15 US US09/936,598 patent/US6562939B1/en not_active Expired - Fee Related
- 2000-03-15 EP EP04077835A patent/EP1512709B1/de not_active Expired - Lifetime
- 2000-03-15 WO PCT/EP2000/002305 patent/WO2000055236A1/en not_active Ceased
- 2000-03-15 DE DE60036737T patent/DE60036737T2/de not_active Expired - Lifetime
- 2000-03-15 ES ES04077835T patent/ES2294428T3/es not_active Expired - Lifetime
- 2000-03-15 AU AU32899/00A patent/AU756070B2/en not_active Ceased
- 2000-03-15 AT AT04077835T patent/ATE375374T1/de not_active IP Right Cessation
- 2000-03-15 CA CA002365485A patent/CA2365485C/en not_active Expired - Fee Related
- 2000-03-15 JP JP2000605661A patent/JP2002539309A/ja active Pending
2001
- 2001-09-14 NO NO20014456A patent/NO329458B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
ES2294428T3 (es)	2008-04-01
DE60036737T2 (de)	2008-07-17
US6562939B1 (en)	2003-05-13
EP1512709A2 (de)	2005-03-09
IT1307022B1 (it)	2001-10-23
DE60036737D1 (de)	2007-11-22
CA2365485C (en)	2010-02-02
WO2000055236A1 (en)	2000-09-21
EP1165650A1 (de)	2002-01-02
JP2002539309A (ja)	2002-11-19
NO20014456L (no)	2001-09-14
CA2365485A1 (en)	2000-09-21
ATE375374T1 (de)	2007-10-15
NO20014456D0 (no)	2001-09-14
EP1512709B1 (de)	2007-10-10
EP1512709A3 (de)	2005-03-23
AU756070B2 (en)	2003-01-02
ITTO990198A1 (it)	2000-09-15
AU3289900A (en)	2000-10-04

Legal Events

Date	Code	Title	Description
2011-10-24	MM1K	Lapsed by not paying the annual fees

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