ES2642859T3 - Poliesteroles para la producción de espumas rígidas de poliuretano - Google Patents
Poliesteroles para la producción de espumas rígidas de poliuretano Download PDFInfo
- Publication number
- ES2642859T3 ES2642859T3 ES13725379.5T ES13725379T ES2642859T3 ES 2642859 T3 ES2642859 T3 ES 2642859T3 ES 13725379 T ES13725379 T ES 13725379T ES 2642859 T3 ES2642859 T3 ES 2642859T3
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- Spain
- Prior art keywords
- polyester
- weight
- component
- polyol
- mol
- 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.)
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- 238000004519 manufacturing process Methods 0.000 title claims description 29
- 229920005830 Polyurethane Foam Polymers 0.000 title claims description 27
- 239000011496 polyurethane foam Substances 0.000 title claims description 25
- 229920005862 polyol Polymers 0.000 claims description 63
- 150000003077 polyols Chemical class 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 52
- 229920000728 polyester Polymers 0.000 claims description 46
- -1 polyethylene terephthalate Polymers 0.000 claims description 45
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 43
- 229920000570 polyether Polymers 0.000 claims description 43
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 42
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 38
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 35
- 239000003380 propellant Substances 0.000 claims description 31
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 30
- 229920005906 polyester polyol Polymers 0.000 claims description 30
- 239000006260 foam Substances 0.000 claims description 27
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 22
- 239000005056 polyisocyanate Substances 0.000 claims description 22
- 229920001228 polyisocyanate Polymers 0.000 claims description 22
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 20
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 16
- 235000011187 glycerol Nutrition 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 14
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
- 239000000194 fatty acid Substances 0.000 claims description 14
- 229930195729 fatty acid Natural products 0.000 claims description 14
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 13
- 150000002009 diols Chemical class 0.000 claims description 13
- 239000003063 flame retardant Substances 0.000 claims description 13
- 150000004665 fatty acids Chemical class 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 10
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 10
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 9
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- 239000012757 flame retardant agent Substances 0.000 claims description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 8
- 239000011495 polyisocyanurate Substances 0.000 claims description 8
- 229920000582 polyisocyanurate Polymers 0.000 claims description 8
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- WEHZNZTWKUYVIY-UHFFFAOYSA-N 3-oxabicyclo[3.2.2]nona-1(7),5,8-triene-2,4-dione Chemical class O=C1OC(=O)C2=CC=C1C=C2 WEHZNZTWKUYVIY-UHFFFAOYSA-N 0.000 claims description 4
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 4
- 239000003760 tallow Substances 0.000 claims description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 70
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 42
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 32
- 239000012948 isocyanate Substances 0.000 description 29
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 27
- 150000002513 isocyanates Chemical class 0.000 description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 230000032050 esterification Effects 0.000 description 12
- 238000005886 esterification reaction Methods 0.000 description 12
- 239000004814 polyurethane Substances 0.000 description 12
- 229920002635 polyurethane Polymers 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 9
- 230000007547 defect Effects 0.000 description 9
- 238000011161 development Methods 0.000 description 9
- 235000019253 formic acid Nutrition 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 7
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000779 smoke Substances 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- GTRSAMFYSUBAGN-UHFFFAOYSA-N tris(2-chloropropyl) phosphate Chemical compound CC(Cl)COP(=O)(OCC(C)Cl)OCC(C)Cl GTRSAMFYSUBAGN-UHFFFAOYSA-N 0.000 description 6
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 229930006000 Sucrose Natural products 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 229960002887 deanol Drugs 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 229960004793 sucrose Drugs 0.000 description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
- 230000000007 visual effect Effects 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000012972 dimethylethanolamine Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 239000011133 lead Substances 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- YWDFOLFVOVCBIU-UHFFFAOYSA-N 1-dimethoxyphosphorylpropane Chemical compound CCCP(=O)(OC)OC YWDFOLFVOVCBIU-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
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- 210000004027 cell Anatomy 0.000 description 3
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- 230000000052 comparative effect Effects 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
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- 235000011056 potassium acetate Nutrition 0.000 description 3
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 3
- 229960003656 ricinoleic acid Drugs 0.000 description 3
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- 238000005809 transesterification reaction Methods 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
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- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
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- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 2
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- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
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- 229910052783 alkali metal Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
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- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
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| US9475220B2 (en) | 2013-02-13 | 2016-10-25 | Basf Se | Process for producing composite elements |
| CN106554488A (zh) * | 2016-06-28 | 2017-04-05 | 宁夏海诚电化信息科技有限公司 | 一种聚酯多元醇生产工艺 |
| DK3574033T3 (da) | 2017-01-25 | 2021-03-22 | Basf Se | Kuldefleksibel polyurethanformulering |
| EP3581599A1 (de) * | 2018-06-15 | 2019-12-18 | Covestro Deutschland AG | Thiocarbonat-haltige pur/pir-hartschäume und daraus erhaltene polyurethane |
| CA3109540A1 (en) * | 2018-08-16 | 2020-02-20 | Basf Se | Environmentally friendly driven polyurethane spray foam systems |
| CN110387032B (zh) * | 2019-07-25 | 2021-07-23 | 万华化学集团股份有限公司 | 一种聚醚酯多元醇、其制备方法及其制备的聚氨酯弹性体 |
| CN116410434B (zh) * | 2023-02-27 | 2024-08-06 | 廊坊华宇创新科技有限公司 | 一种聚氨酯硬泡组合聚酯、制备方法及应用 |
| FR3160410A1 (fr) * | 2024-03-20 | 2025-09-26 | Bostik Sa | Composition de polyuréthane |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1003714B (de) | 1956-01-25 | 1957-03-07 | Glanzstoff Ag | Verfahren zum Abbau von Polyaethylenterephthalat zu Terephthalsaeuredimethylester |
| US5051528A (en) | 1990-04-24 | 1991-09-24 | Eastman Kodak Company | Recovery process for ethylene glycol and dimethylterephthalate |
| AR017610A1 (es) * | 1997-11-13 | 2001-09-12 | Dow Chemical Co | Procedimiento para preparar polieterespolioles utilizando imidazoles como catalizadores |
| ATE257162T1 (de) | 1998-02-23 | 2004-01-15 | Stepan Co | Niedrigviskose polyesterpolyole und verfahren zu ihrer herstellung |
| JP4796401B2 (ja) * | 2005-11-30 | 2011-10-19 | Ｊｘ日鉱日石エネルギー株式会社 | 流動接触分解を用いたバイオマスの処理方法 |
| WO2007111834A2 (en) * | 2006-03-23 | 2007-10-04 | Dow Global Technologies Inc. | Natural oil based polyols with intrinsic surpactancy for polyurethane foaming |
| SI2340269T1 (sl) * | 2008-10-15 | 2013-01-31 | Basf Se | Poliesterski polioli na bazi terefthalične kisline |
| CA2819569C (en) * | 2010-12-02 | 2020-01-14 | Basf Se | Polyester polyols based on aromatic dicarboxylic acids |
| EP2492297A1 (de) * | 2011-02-23 | 2012-08-29 | Basf Se | Polyesterpolyole auf Basis aromatischer Dicarbonsäuren und daraus hergestellte Polyurethanhartschäume |
-
2013
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- 2013-05-28 MX MX2014014626A patent/MX369139B/es active IP Right Grant
- 2013-05-28 CA CA2874910A patent/CA2874910C/en active Active
- 2013-05-28 PT PT137253795T patent/PT2855557T/pt unknown
- 2013-05-28 JP JP2015514459A patent/JP6265977B2/ja not_active Expired - Fee Related
- 2013-05-28 AU AU2013269763A patent/AU2013269763B2/en not_active Ceased
- 2013-05-28 WO PCT/EP2013/060947 patent/WO2013178623A1/de not_active Ceased
- 2013-05-28 RU RU2014153659A patent/RU2643135C2/ru active
- 2013-05-28 KR KR1020147036834A patent/KR102101755B1/ko active Active
- 2013-05-28 CN CN201380040149.6A patent/CN104736599A/zh active Pending
- 2013-05-28 ES ES13725379.5T patent/ES2642859T3/es active Active
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- 2013-05-28 PL PL13725379T patent/PL2855557T3/pl unknown
- 2013-05-28 BR BR112014029715-0A patent/BR112014029715B1/pt active IP Right Grant
- 2013-05-28 HU HUE13725379A patent/HUE036775T2/hu unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| CN104736599A (zh) | 2015-06-24 |
| EP2855557B1 (de) | 2017-07-12 |
| PL2855557T3 (pl) | 2018-01-31 |
| WO2013178623A1 (de) | 2013-12-05 |
| HUE036775T2 (hu) | 2018-07-30 |
| AU2013269763A1 (en) | 2014-12-18 |
| KR20150027153A (ko) | 2015-03-11 |
| BR112014029715B1 (pt) | 2021-02-23 |
| RU2643135C2 (ru) | 2018-01-31 |
| CA2874910C (en) | 2020-08-25 |
| MX369139B (es) | 2019-10-30 |
| RU2014153659A (ru) | 2016-07-27 |
| MX2014014626A (es) | 2015-08-06 |
| EP2855557A1 (de) | 2015-04-08 |
| JP6265977B2 (ja) | 2018-01-24 |
| CA2874910A1 (en) | 2013-12-05 |
| KR102101755B1 (ko) | 2020-04-20 |
| PT2855557T (pt) | 2017-10-13 |
| AU2013269763B2 (en) | 2016-05-12 |
| JP2015523431A (ja) | 2015-08-13 |
| BR112014029715A2 (pt) | 2019-07-30 |
| ZA201409465B (en) | 2017-05-31 |
| RS56449B1 (sr) | 2018-01-31 |
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