DE2115072A1 - Herstellung von Mischpolyestern auf Caprolacton-Basis - Google Patents
Herstellung von Mischpolyestern auf Caprolacton-BasisInfo
- Publication number
- DE2115072A1 DE2115072A1 DE19712115072 DE2115072A DE2115072A1 DE 2115072 A1 DE2115072 A1 DE 2115072A1 DE 19712115072 DE19712115072 DE 19712115072 DE 2115072 A DE2115072 A DE 2115072A DE 2115072 A1 DE2115072 A1 DE 2115072A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- caprolactone
- antimony
- polyester
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920000728 polyester Polymers 0.000 title claims description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 title description 21
- 238000000034 method Methods 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229920005862 polyol Polymers 0.000 claims description 12
- -1 alkyl radical Chemical class 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 claims description 3
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 239000001361 adipic acid Substances 0.000 description 12
- 235000011037 adipic acid Nutrition 0.000 description 12
- 230000032050 esterification Effects 0.000 description 11
- 238000005886 esterification reaction Methods 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- ITFDYXKCBZEBDG-UHFFFAOYSA-N 2-(1-methylpyrrol-2-yl)ethanamine Chemical compound CN1C=CC=C1CCN ITFDYXKCBZEBDG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Inorganic materials O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000012694 Lactone Polymerization Methods 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QZRSVBDWRWTHMT-UHFFFAOYSA-M silver;3-carboxy-3,5-dihydroxy-5-oxopentanoate Chemical compound [Ag+].OC(=O)CC(O)(C([O-])=O)CC(O)=O QZRSVBDWRWTHMT-UHFFFAOYSA-M 0.000 description 2
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical group C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- GBURUDXSBYGPBL-UHFFFAOYSA-N 2,2,3-trimethylhexanedioic acid Chemical compound OC(=O)C(C)(C)C(C)CCC(O)=O GBURUDXSBYGPBL-UHFFFAOYSA-N 0.000 description 1
- LFQSIOGYPMEIGZ-UHFFFAOYSA-N 2-heptyldodecanedioic acid Chemical compound CCCCCCCC(C(O)=O)CCCCCCCCCC(O)=O LFQSIOGYPMEIGZ-UHFFFAOYSA-N 0.000 description 1
- DBBJDJNEABXOIX-UHFFFAOYSA-N 3-ethyloxepan-2-one Chemical compound CCC1CCCCOC1=O DBBJDJNEABXOIX-UHFFFAOYSA-N 0.000 description 1
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 1
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 1
- 241000033695 Sige Species 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
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 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
- 238000001914 filtration Methods 0.000 description 1
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229940113165 trimethylolpropane Drugs 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4286—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones prepared from a combination of hydroxycarboxylic acids and/or lactones with polycarboxylic acids or ester forming derivatives thereof 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
-
- 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
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712115072 DE2115072A1 (de) | 1971-03-29 | 1971-03-29 | Herstellung von Mischpolyestern auf Caprolacton-Basis |
| DE19712123969 DE2123969A1 (de) | 1971-03-29 | 1971-05-14 | Herstellung von Mischpolyestern auf Caprolacton-Basis |
| DE19712135307 DE2135307A1 (de) | 1971-03-29 | 1971-07-15 | Herstellung von mischpolyestern auf caprolacton-basis |
| IT2234172A IT950727B (it) | 1971-03-29 | 1972-03-24 | Preparazione di poliesteri misti a base di caprolattone |
| FR7210856A FR2132139B1 (show.php) | 1971-03-29 | 1972-03-28 | |
| NL7204281A NL7204281A (show.php) | 1971-03-29 | 1972-03-29 | |
| GB1480772A GB1376353A (en) | 1971-03-29 | 1972-03-29 | Manufacture of copolyesters base on caprolactones |
| BE781391A BE781391A (fr) | 1971-03-29 | 1972-03-29 | Polyesters mixtes a base de caprolactones |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712115072 DE2115072A1 (de) | 1971-03-29 | 1971-03-29 | Herstellung von Mischpolyestern auf Caprolacton-Basis |
| DE19712123969 DE2123969A1 (de) | 1971-03-29 | 1971-05-14 | Herstellung von Mischpolyestern auf Caprolacton-Basis |
| DE19712135307 DE2135307A1 (de) | 1971-03-29 | 1971-07-15 | Herstellung von mischpolyestern auf caprolacton-basis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2115072A1 true DE2115072A1 (de) | 1972-10-05 |
Family
ID=27183310
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712115072 Pending DE2115072A1 (de) | 1971-03-29 | 1971-03-29 | Herstellung von Mischpolyestern auf Caprolacton-Basis |
| DE19712123969 Pending DE2123969A1 (de) | 1971-03-29 | 1971-05-14 | Herstellung von Mischpolyestern auf Caprolacton-Basis |
| DE19712135307 Pending DE2135307A1 (de) | 1971-03-29 | 1971-07-15 | Herstellung von mischpolyestern auf caprolacton-basis |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712123969 Pending DE2123969A1 (de) | 1971-03-29 | 1971-05-14 | Herstellung von Mischpolyestern auf Caprolacton-Basis |
| DE19712135307 Pending DE2135307A1 (de) | 1971-03-29 | 1971-07-15 | Herstellung von mischpolyestern auf caprolacton-basis |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE781391A (show.php) |
| DE (3) | DE2115072A1 (show.php) |
| FR (1) | FR2132139B1 (show.php) |
| GB (1) | GB1376353A (show.php) |
| IT (1) | IT950727B (show.php) |
| NL (1) | NL7204281A (show.php) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2723656A1 (de) * | 1976-05-26 | 1977-12-01 | Union Carbide Corp | Polycaprolacton-derivate und ueberzugskompositionen |
| CN102648223A (zh) * | 2009-08-21 | 2012-08-22 | 科聚亚公司 | 共聚酯多元醇、预聚物以及由其形成的聚氨酯弹性体和制备它们的方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2123466B1 (es) * | 1997-06-11 | 1999-11-16 | Merquinsa Mercados Quimicos S | Termoplastico de poliuretano y procedimiento para su obtencion. |
| DE102006048288A1 (de) | 2006-10-12 | 2008-04-17 | Bayer Materialscience Ag | Polyesterpolyole, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US20160208135A1 (en) * | 2013-08-28 | 2016-07-21 | Basf Coatings Gmbh | Dimer fatty acid/polyesterdiol reaction product and use thereof in coating materials |
| GB201317113D0 (en) * | 2013-09-26 | 2013-11-06 | Croda Int Plc | A co-polymer polyol |
| GB201402580D0 (en) * | 2014-02-14 | 2014-04-02 | Croda Int Plc | Polyurethane elastomers |
| GB201402585D0 (en) * | 2014-02-14 | 2014-04-02 | Croda Int Plc | Polyurethane dispersions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1076877A (en) * | 1964-06-03 | 1967-07-26 | Asahi Chemical Ind | Method for producing linear copolyesters |
-
1971
- 1971-03-29 DE DE19712115072 patent/DE2115072A1/de active Pending
- 1971-05-14 DE DE19712123969 patent/DE2123969A1/de active Pending
- 1971-07-15 DE DE19712135307 patent/DE2135307A1/de active Pending
-
1972
- 1972-03-24 IT IT2234172A patent/IT950727B/it active
- 1972-03-28 FR FR7210856A patent/FR2132139B1/fr not_active Expired
- 1972-03-29 NL NL7204281A patent/NL7204281A/xx unknown
- 1972-03-29 BE BE781391A patent/BE781391A/xx unknown
- 1972-03-29 GB GB1480772A patent/GB1376353A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2723656A1 (de) * | 1976-05-26 | 1977-12-01 | Union Carbide Corp | Polycaprolacton-derivate und ueberzugskompositionen |
| CN102648223A (zh) * | 2009-08-21 | 2012-08-22 | 科聚亚公司 | 共聚酯多元醇、预聚物以及由其形成的聚氨酯弹性体和制备它们的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2123969A1 (de) | 1972-11-16 |
| BE781391A (fr) | 1972-09-29 |
| IT950727B (it) | 1973-06-20 |
| NL7204281A (show.php) | 1972-10-03 |
| FR2132139B1 (show.php) | 1977-08-19 |
| GB1376353A (en) | 1974-12-04 |
| FR2132139A1 (show.php) | 1972-11-17 |
| DE2135307A1 (de) | 1973-01-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |