CN107075078B - 用于制备聚氨酯弹性体和热塑性聚氨酯的聚酯改性的聚丁二烯醇 - Google Patents
用于制备聚氨酯弹性体和热塑性聚氨酯的聚酯改性的聚丁二烯醇 Download PDFInfo
- Publication number
- CN107075078B CN107075078B CN201580056393.0A CN201580056393A CN107075078B CN 107075078 B CN107075078 B CN 107075078B CN 201580056393 A CN201580056393 A CN 201580056393A CN 107075078 B CN107075078 B CN 107075078B
- Authority
- CN
- China
- Prior art keywords
- weight
- parts
- component
- optionally
- polyurethane
- 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.)
- Active
Links
- 229920002857 polybutadiene Polymers 0.000 title claims abstract description 39
- 239000005062 Polybutadiene Substances 0.000 title claims abstract description 38
- 150000001298 alcohols Chemical class 0.000 title abstract description 19
- 229920003225 polyurethane elastomer Polymers 0.000 title description 34
- 239000004433 Thermoplastic polyurethane Substances 0.000 title description 20
- 229920002803 thermoplastic polyurethane Polymers 0.000 title description 20
- 238000004519 manufacturing process Methods 0.000 title description 7
- 239000004814 polyurethane Substances 0.000 claims abstract description 29
- 229920002635 polyurethane Polymers 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 239000004970 Chain extender Substances 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000004604 Blowing Agent Substances 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 229920001400 block copolymer Polymers 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 150000002009 diols Chemical class 0.000 claims abstract description 12
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 12
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 12
- 229920000642 polymer Polymers 0.000 claims abstract description 8
- 239000000654 additive Substances 0.000 claims abstract description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000003077 polyols Chemical class 0.000 claims description 91
- 229920005862 polyol Polymers 0.000 claims description 90
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 30
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 24
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical group O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
- -1 cyclic ester Chemical class 0.000 claims description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 13
- 229960004063 propylene glycol Drugs 0.000 claims description 8
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 6
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 3
- 239000004971 Cross linker Substances 0.000 abstract description 9
- 150000004072 triols Chemical class 0.000 abstract description 5
- 125000004122 cyclic group Chemical group 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 description 26
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 16
- 239000012948 isocyanate Substances 0.000 description 14
- 150000002513 isocyanates Chemical class 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000004721 Polyphenylene oxide Substances 0.000 description 11
- 239000006260 foam Substances 0.000 description 11
- 229920000570 polyether Polymers 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 229920001971 elastomer Polymers 0.000 description 10
- 239000000806 elastomer Substances 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 229920005906 polyester polyol Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 229940113120 dipropylene glycol Drugs 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000008961 swelling Effects 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 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 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 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 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 238000006735 epoxidation reaction Methods 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229920001610 polycaprolactone Polymers 0.000 description 4
- 239000004632 polycaprolactone Substances 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- 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
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000012766 organic filler Substances 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
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- 229940043375 1,5-pentanediol Drugs 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical class [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 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
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical class [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 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
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- 239000012972 dimethylethanolamine Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000004872 foam stabilizing agent Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical class NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 229920002725 thermoplastic elastomer Polymers 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 1
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 1
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
- DMUPYMORYHFFCT-UHFFFAOYSA-N 1,2,3,3,3-pentafluoroprop-1-ene Chemical compound FC=C(F)C(F)(F)F DMUPYMORYHFFCT-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- ZFDWWDZLRKHULH-UHFFFAOYSA-N 1,2-dimethyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C ZFDWWDZLRKHULH-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- FCQPNTOQFPJCMF-UHFFFAOYSA-N 1,3-bis[3-(dimethylamino)propyl]urea Chemical compound CN(C)CCCNC(=O)NCCCN(C)C FCQPNTOQFPJCMF-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- AXKZIDYFAMKWSA-UHFFFAOYSA-N 1,6-dioxacyclododecane-7,12-dione Chemical compound O=C1CCCCC(=O)OCCCCO1 AXKZIDYFAMKWSA-UHFFFAOYSA-N 0.000 description 1
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical class C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-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
- GEEGPFGTMRWCID-UHFFFAOYSA-N 1-n,1-n,1-n',1-n'-tetramethylbutane-1,1-diamine Chemical compound CCCC(N(C)C)N(C)C GEEGPFGTMRWCID-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical class NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- CVFRFSNPBJUQMG-UHFFFAOYSA-N 2,3-bis(2-hydroxyethyl)benzene-1,4-diol Chemical compound OCCC1=C(O)C=CC(O)=C1CCO CVFRFSNPBJUQMG-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- RZEWIYUUNKCGKA-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanol;octadecanoic acid Chemical compound OCCNCCO.CCCCCCCCCCCCCCCCCC(O)=O RZEWIYUUNKCGKA-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- BZGBTLYQQQASEF-UHFFFAOYSA-N 3-dodecylbenzene-1,2-disulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC(S(O)(=O)=O)=C1S(O)(=O)=O BZGBTLYQQQASEF-UHFFFAOYSA-N 0.000 description 1
- BRKHZWFIIVVNTA-UHFFFAOYSA-N 4-cyclohexylmorpholine Chemical compound C1CCCCC1N1CCOCC1 BRKHZWFIIVVNTA-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- FTXUQEKXCJSWMO-UHFFFAOYSA-N Nonanolactone Chemical compound O=C1CCCCCCCCO1 FTXUQEKXCJSWMO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical class O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- BZEZSORUWZUMNU-UHFFFAOYSA-N [Li]CCCC[Li] Chemical compound [Li]CCCC[Li] BZEZSORUWZUMNU-UHFFFAOYSA-N 0.000 description 1
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000002862 amidating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052612 amphibole Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 229910052898 antigorite Inorganic materials 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
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- NUMHJBONQMZPBW-UHFFFAOYSA-K bis(2-ethylhexanoyloxy)bismuthanyl 2-ethylhexanoate Chemical compound [Bi+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O NUMHJBONQMZPBW-UHFFFAOYSA-K 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- FNYKAWJEEWSNEH-UHFFFAOYSA-K bismuth;3,3,5,5-tetramethylhexanoate Chemical compound [Bi+3].CC(C)(C)CC(C)(C)CC([O-])=O.CC(C)(C)CC(C)(C)CC([O-])=O.CC(C)(C)CC(C)(C)CC([O-])=O FNYKAWJEEWSNEH-UHFFFAOYSA-K 0.000 description 1
- ZZUFUNZTPNRBID-UHFFFAOYSA-K bismuth;octanoate Chemical compound [Bi+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O ZZUFUNZTPNRBID-UHFFFAOYSA-K 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical class CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 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
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- ZHMPXIDAUXCKIQ-UHFFFAOYSA-N cyclohexane-1,2,4-triol Chemical compound OC1CCC(O)C(O)C1 ZHMPXIDAUXCKIQ-UHFFFAOYSA-N 0.000 description 1
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 1
- FSDSKERRNURGGO-UHFFFAOYSA-N cyclohexane-1,3,5-triol Chemical compound OC1CC(O)CC(O)C1 FSDSKERRNURGGO-UHFFFAOYSA-N 0.000 description 1
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- BRWZYZWZBMGMMG-UHFFFAOYSA-J dodecanoate tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O BRWZYZWZBMGMMG-UHFFFAOYSA-J 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- PLONEVHFXDFSLA-UHFFFAOYSA-N ethyl hexanoate;tin(2+) Chemical compound [Sn+2].CCCCCC(=O)OCC PLONEVHFXDFSLA-UHFFFAOYSA-N 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229910052892 hornblende Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001841 imino group Chemical class [H]N=* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- HOKMYEORIPLLGI-KVVVOXFISA-N n-ethylethanamine;(z)-octadec-9-enoic acid Chemical compound CCNCC.CCCCCCCC\C=C/CCCCCCCC(O)=O HOKMYEORIPLLGI-KVVVOXFISA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- ADRDEXBBJTUCND-UHFFFAOYSA-N pyrrolizidine Chemical compound C1CCN2CCCC21 ADRDEXBBJTUCND-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 239000005436 troposphere Substances 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Chemical class 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 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
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6204—Polymers of olefins
- C08G18/6208—Hydrogenated polymers of conjugated dienes
-
- 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
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/4269—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
- 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
- C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
- C08G18/638—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers characterised by the use of compounds having carbon-to-carbon double bonds other than styrene and/or olefinic nitriles
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6511—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38 compounds of group C08G18/3203
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
本发明涉及可通过以下物质的反应获得的聚氨酯：a)多异氰酸酯A，其选自任选改性的4,4'‑甲烷二苯基二异氰酸酯、4,4'‑甲烷二苯基二异氰酸酯的含有更多环的同系物、基于4,4'‑甲烷二苯基二异氰酸酯的含异氰酸酯基团的预聚物以及它们的混合物，b)具有至少两个异氰酸酯反应性氢原子的化合物，其包含b1)聚丁二烯醇与环酯的嵌段共聚物作为组分B1，以及b2)作为低分子量增链剂的二醇和任选的作为交联剂的三醇，分子量为62至500g/mol，作为组分B2，c)任选的具有至少2个对异氰酸酯呈反应性的氢原子的其他聚合化合物C，d)任选的催化剂D，e)任选的水E，f)任选的物理发泡剂F，g)任选的其他助剂和/或添加剂G。
Description
本发明涉及由聚丁二烯醇(polybutadienol)和环酯(例如ε-己内酯)形成的嵌段共聚物用于制备聚氨酯的用途，涉及所述聚氨酯本身，以及涉及一种包含所述嵌段共聚物的多元醇组分。
液体的羟基封端的聚丁二烯(HTPB)众所周知，并在聚氨酯的制备中用作多元醇组分。市售可得的羟基封端聚丁二烯通过1,3-丁二烯的自由基聚合获得，如US 3965140中所述；或通过1,3-丁二烯的离子聚合获得，如DD 160223中所述。用于引发和终止HTPB的制备的试剂特别重要。根据制备过程，获得每个大分子具有不同数目官能团的多元醇。
这些羟基封端的聚丁二烯可用作制备聚氨酯弹性体的多元醇组分。除多元醇组分外，通常还将低分子量二醇增链剂或低分子量三醇交联剂混合来生产聚氨酯弹性体。由HTPB和各种增链剂形成的聚氨酯弹性体已记载在多个出版物中，包括J.App.Pol.Sci.1971，15，2941-2956；Pol.Eng.Sci.1981,21,668-674；J.App.Pol.Sci,2002,85,84-91。然而，HTPB尚未广泛使用，其原因是难处理。这些困难是由于这些多元醇与异氰酸酯和常规增链剂如1,4-丁二醇的混溶性差。所获得的聚氨酯弹性体由于它们的不相容性而具有不足的机械性能。例如，来自Cray Valley(Exton,PA,USA),4880-01/10,“NovelPolybutadiene Diols for ThermoplasticPolyurethanes”的技术公告认为，不可能由Krasol LBH等级、1,4-丁二醇和4,4'-MDI形成热塑性聚氨酯(TPU)。所述原因是原料之间的相容性差。由于这种差的相容性，显然不可能使分子量增长到足够的水平。在这种情况下，该问题通过使用更相容但非典型的TPU增链剂(例如2-乙基-1,3-己二醇)解决。
EP 1 710 263 B1公开了一种可通过以下物质的反应获得的聚氨酯橡胶：
(a)可通过以下物质的反应获得的异氰酸酯预聚物，
(a-1)异氰酸酯与
(a-2)聚二烯醇，与
(b)具有异氰酸酯反应性基团的化合物，
其中在组分(a)和(b)反应期间混合的聚二烯醇总计大于15重量％，基于组分(a)和(b)的总重量计。聚二烯醇(a-2)具有末端OH基团，OH官能度为2.0至2.6且数均分子量为1000g/mol至5000g/mol。组分(b)优选包含：聚醚多元醇(b-1)，其可通过使二官能、三官能或四官能起始分子烷氧基化获得；聚四氢呋喃(b-2)；聚酯多元醇(b-3)；聚丁二烯醇(b-4)；以及增链剂(b-5)。还公开了所述聚氨酯橡胶作为2组分粘合剂的用途。
己内酯(CL)的开环聚合是已知的。将HTPB用作制备嵌段共聚物的引发剂记载在例如Macromolecules,2006,39,711-719和e-Polymers,2009,No.032中。所得的具有结构CL-嵌段-HTPB-嵌段-CL的多元醇组分目前尚不用于常规聚氨酯用途中。EP 0 266 697中描述的用途是作为火箭燃料的粘合剂。
JP 6002341A描述了通过使用聚丁二烯多元醇作为引发剂的内酯的开环聚合。一个实例的特征在于，在Ti(BuO)4作为催化剂存在下使聚丁二烯多元醇与ε-己内酰胺反应。内酯聚合物据称可用于制备聚氨酯弹性体、泡沫、胶粘剂和涂料。
本发明的目的是提供一种用于制备聚氨酯弹性体和热塑性聚氨酯的易于与其他组分相容的聚丁二烯醇基多元醇组分。本发明的目的还在于提供具有非常好的机械性能的聚氨酯弹性体和热塑性聚氨酯。
我们已发现，该目的通过可通过以下物质的反应获得的聚氨酯实现：
a)多异氰酸酯A，选自任选改性的4,4'-甲烷二苯基二异氰酸酯、4,4'-甲烷二苯基二异氰酸酯的更高级核同系物、基于4,4'-甲烷二苯基二异氰酸酯的含异氰酸酯基团的预聚物以及它们的混合物，与
b)具有至少两个异氰酸酯反应性氢原子的化合物，其包含
b1)由聚丁二烯醇和环酯形成的嵌段共聚物，作为组分B1，以及
b2)作为低分子量增链剂的二醇和任选的作为交联剂的三醇，分子量为62至500g/mol，作为组分B2，
c)任选的具有至少2个异氰酸酯反应性氢原子的其他聚合化合物C，
d)任选的催化剂D，
e)任选的水E，
f)任选的物理发泡剂F，
g)任选的其他助剂和/或添加剂G。
本发明的聚氨酯可以是聚氨酯弹性体(PU弹性体)或热塑性弹性体(TPU)，在这种情况下，聚氨酯弹性体也可以是泡沫。
本发明的聚氨酯弹性体至少由多元醇、增链剂和多异氰酸酯形成，条件是多元醇是由聚丁二烯醇和环酯形成的嵌段共聚物。优选的环酯是ε-己内酯、1,6-二氧杂环十二烷-7,12-二酮(CAS777-95-7)和氧杂环癸烷-2-酮(CAS 947-05-7)。
在一个特别优选的实施方案中，环酯是ε-己内酯(CL)。因此，多元醇组分B1是由聚丁二烯醇和ε-己内酯形成的嵌段共聚物并具有结构(CL-嵌段-HTPB-嵌段-CL)。基于CL-嵌段-HTPB-嵌段-CL多元醇的聚氨酯弹性体比基于羟基封端的聚丁二烯且不含聚酯改性剂的聚氨酯弹性体具有更好的机械性能。基于聚酯改性的HTPB(其中ε-己内酯为聚酯改性剂)的聚氨酯还非常疏水，尽管有酯部分但仍表现出非常好的水溶胀值。
制备热塑性弹性体要求聚酯改性的聚丁二烯醇是双官能的。用于制备TPU的合适的聚酯改性聚丁二烯醇B2是基于通过由双官能起始剂(例如1,4-二锂丁烷)开始的阴离子聚合形成的羟基封端的聚丁二烯(HTPB)的那些。羟基封端的聚丁二烯的制备描述于例如DD154609和DD 159775中。
聚氨酯弹性体也可使用具有一定支化度的聚酯改性聚丁二烯醇获得。合适的聚丁二烯醇通过受控自由基聚合或通过阴离子聚合形成，或者是由液体聚丁二烯形成的羟基改性的聚丁二烯，例如可从Synthomer,Essex,UK以商品名
获得的产品。
羟基改性的聚丁二烯可由数均分子量通常为500至10000g/mol、优选750至7500g/mol、更优选1000至5000g/mol且尤其是1000至2000g/mol的非官能化聚丁二烯低聚物获得。一种可能的方法是部分环氧化存在的双键，然后用合适的亲核试剂打开这些环氧化物。聚二烯的环氧化描述在例如Perera,Ind.Eng.Chem.Res.1988,27,2196-2203中。聚丁二烯可以与多羧酸反应得到环氧化产物。所述多羧酸可以直接使用或者由羧酸和过氧化氢原位形成。环氧化可以例如使用甲酸作为最简单的羧酸来进行。
环氧化的聚丁二烯可借助合适的亲核试剂(例如水、醇或胺)转化为羟基官能化聚丁二烯。醇如乙醇和丁醇是优选的。用于该反应的合适的催化剂是强酸如无机酸，如EP0585265B1中所述，例如，如US 5,242,989中所述的三氟化硼或如Li,J.Macromol.Sci,PartA,2013,50,297-301和WO 96/20234中所述的三氟甲磺酸。
与通过阴离子聚合或自由基聚合形成的HTPB不同，后官能化的聚丁二烯醇不是选择性羟基封端的，而是具有沿聚丁二烯骨架无规分布的羟基。
通过阴离子聚合或自由基聚合形成的HTPB或通过环氧化获得的后官能化聚丁二烯醇随后在催化剂存在下通过与环酯(例如ε-己内酯)开环共聚进行聚酯改性。所用的催化剂是钛催化剂如四丁氧基钛，如JP-A60023418中所述。
作为交联剂或增链剂B2，可以使用分子量为62至500g/mol、更优选为62至400g/mol的物质，其中增链剂具有2个异氰酸酯反应性氢原子且交联剂具有3个异氰酸酯反应性氢原子。它们可以单独使用或优选作为混合物使用。优选使用分子量小于500、更优选为62至400且尤其为62至350的二醇和/或三醇。可能的物质包括，例如，具有2至14个、优选2至10个碳原子的脂族、脂环族和/或芳脂族或芳族二醇，例如乙二醇、1,2-丙二醇、2-甲基-1,3-丙二醇、1,3-丙二醇、1,4-丁二醇、1,6-己二醇、1,10-癸二醇和双(2-羟乙基)氢醌、1,2-二羟基环己烷、1,3-二羟基环己烷、1,4-二羟基环己烷、双酚A双(羟乙基醚)、二乙二醇、二丙二醇、三丙二醇；三醇，例如1,2,4-三羟基环己烷、1,3,5-三羟基环己烷、丙三醇和三羟甲基丙烷；二乙醇胺、三乙醇胺；以及基于环氧乙烷和/或1,2-环氧丙烷并以上述二醇和/或三醇作为起始分子的低分子量含羟基的聚环氧烷。特别优选将基于环氧乙烷和/或1,2-环氧丙烷(更优选环氧乙烷)和三官能起始剂(尤其是丙三醇和三羟甲基丙烷)的低分子量含羟基的聚环氧烷用作交联剂B2。特别优选的增链剂B2是乙二醇、1,2-丙二醇、1,3-丙二醇、2-甲基-1,3-丙二醇、1,4-丁二醇、二乙二醇和二丙二醇。
为制备本发明的聚氨酯反应混合物，使有机多异氰酸酯A与包含具有异氰酸酯反应性氢原子的化合物的组分反应，使得NCO基团与全部反应性氢原子的当量比在0.5:1至3.5:1(相当于异氰酸酯指数为50至350)的范围内，优选为0.85:1至1.30:1且更优选在0.9:1至1.15:1的范围内。
用于制备本发明的聚氨酯模制品的任选改性的多异氰酸酯A包括单体4,4'-甲烷二苯基二异氰酸酯和4,4'-甲烷二苯基二异氰酸酯的高级核同系物的4,4'-甲烷二苯基二异氰酸酯混合物(聚合物MDI)。异氰酸酯也可以是改性异氰酸酯，例如通过引入脲二酮基团、氨基甲酸酯基团、异氰脲酸酯基团、碳二亚胺基团、脲基甲酸酯基团且特别是氨基甲酸酯基团。异氰酸酯组分A也可以包含异氰酸酯基团的异氰酸酯预聚物的形式使用。这些多异氰酸酯预聚物可通过将上述多异氰酸酯作为组分A1，例如在30至100℃、优选约80℃的温度下与多元醇A2反应形成预聚物而获得。
基于4,4'-MDI的含异氰酸酯基团的预聚物通过使任选改性的4,4'-MDI和/或其更高级核同系物与多元醇反应获得。
预聚物优选通过使4,4'-MDI与脲酮亚胺改性的MDI和市售可得的基于聚酯的多元醇(例如以己二酸为原料)或基于聚醚的多元醇(例如以环氧乙烷和/或环氧丙烷为原料)反应来制备。
多元醇A2是本领域技术人员已知的，并且记载在例如“Kunststoffhandbuch,Volume 7,Polyurethane”,Carl Hanser Verlag，第3版1993，第3.1章中。优选聚醚醇用作多元醇A2。所述多元醇A2任选地与作为组分A3的常规增链剂或交联剂混合，以制备异氰酸酯预聚物。这种增链剂将在下文中在B2下描述。特别优选用作增链剂的是分子量最高达500的1,4-丁二醇、1,2-丙二醇、1,3-丁二醇、二丙二醇、三丙二醇和/或丙二醇。优选选择有机多异氰酸酯A1与多元醇A2和增链剂A3的比例，使得异氰酸酯预聚物的NCO含量为10至28％，更优选为14至25％。
适合于制备聚氨酯弹性体的由聚丁二烯醇和环酯(优选ε-己内酯)形成的嵌段共聚物B1的数均分子量通常在600至15 000g/mol的范围内，优选在750至10000g/mol的范围内且更优选在1000至7500g/mol的范围内。在ε-己内酯的情况下，其比例通常为5至75重量％，优选为7至60重量％且更优选为10至50重量％。其OH官能度通常为2至5，优选为2至3.5且更优选为2至3。其通常不仅具有端位OH基团，还具有链位OH基团。
适合于制备热塑性聚氨酯的由聚丁二烯醇和环酯(优选ε-己内酯)形成的嵌段共聚物B1的数均分子量通常在600至15 000g/mol的范围内，优选在750至10000g/mol的范围内且更优选在1000至7500g/mol的范围内。其ε-己内酯的比例通常为5至75重量％，优选为7至60重量％且更优选为10至50重量％。其OH官能度通常为1.5至2.2，优选为1.8至2.2且更优选为1.9至2.1。其基本上仅具有端位OH基团。
本发明的聚氨酯通常可通过以下物质的反应获得：
a)10至300重量份、优选30至150重量份的多异氰酸酯A，
b1)100重量份的多元醇组分B1，
b2)2至20重量份、优选4至15重量份的低分子量增链剂或交联剂，分子量为62至500g/mol，作为组分B2，
c)0至100重量份的具有至少2个异氰酸酯反应性氢原子的其他聚合化合物C，
d)0至5重量份的催化剂D，
e)0至3重量份的水E，
f)0至10重量份的物理发泡剂F，
g)0至100重量份的助剂和/或添加剂G。
在本发明的一个实施方案中，聚氨酯为非多孔聚氨酯弹性体。它们可通过在不存在发泡剂E和F的情况下使组分A、B1、B2、任选的C、任选的D和任选的G以上述量反应而获得。
在本发明的另一个实施方案中，聚氨酯是泡沫。它们可通过在作为发泡剂的水E和/或物理发泡剂F存在下使组分A、B1、B2、任选的C、任选的D和任选的G反应而获得。该反应通常在0.1至10重量份、优选0.2至5重量份物理发泡剂存在下和/或在0.05至3.0重量份、优选0.1至1.0重量份水的存在下进行。
本发明还提供一种多元醇组合物，其包含：
b1)100重量份的由聚丁二烯醇和环酯(优选ε-己内酯)形成的嵌段共聚物，作为组分B1，和
b2)2至20重量份、优选4至10重量份的低分子量增链剂或交联剂，分子量为62至500g/mol，作为组分B2。
在一个优选的实施方案中，组分B2包含乙二醇、1,2-丙二醇、1,3-丙二醇、2-甲基-1,3-丙二醇、1,4-丁二醇、二乙二醇和二丙二醇作为低分子量增链剂。在一个特别优选的实施方案中，组分B2由1,4-丁二醇组成。
在一个进一步优选的实施方案中，组分B2的交联剂选自乙氧基化的和/或丙氧基化的丙三醇和三羟甲基丙烷。
本发明还提供一种使用这样的多元醇组分来制备聚氨酯弹性体或热塑性聚氨酯的方法，所述多元醇组分包含由聚丁二烯醇和环酯(优选ε-己内酯)形成的嵌段共聚物，以及分子量为62至500g/mol的低分子量增链剂或交联剂。
具有至少两个异氰酸酯反应性氢原子的合适的其他聚合化合物C的分子量为至少500g/mol。可使用已知用于聚氨酯制备的具有至少两个反应性氢原子且分子量为至少500g/mol的任何化合物。这类化合物例如应具有2至8的官能度和500至12000g/mol的分子量。因此，可使用例如聚醚多胺和/或选自聚醚多元醇、聚酯多元醇或其混合物的多元醇。
优选使用的其他多元醇C是聚醚醇、聚碳酸酯多元醇和/或聚酯醇，它们的分子量为500至12000g/mol、优选为500至6000g/mol、尤其为500至3000g/mol，并且平均官能度优选为2至6、更优选为2至4。作为其他多元醇C，优选仅使用聚醚醇和/或聚酯多元醇。
聚醚醇C根据已知方法制备。例如，其可通过下述方式制备：以碱金属氢氧化物(例如氢氧化钠、氢氧化钾)或碱金属醇盐(例如甲醇钠、乙醇钠、乙醇钾或异丙醇钾)作为催化剂并在至少一种具有2至8个、优选2至6个反应性氢原子的起始分子的存在下，使具有2至4个碳原子的环氧烷烃进行阴离子聚合；或以路易斯酸(如五氯化锑、氟化硼醚化物等)或漂白土作为催化剂进行阳离子聚合。聚醚多元醇可类似地由一种或多种具有2至4个碳原子的环氧烷烃通过双金属氰化物催化作用来制备。叔胺也可以用作催化剂，实例为三乙胺、三丁胺、三甲胺、二甲基乙醇胺、咪唑或二甲基环己胺。对于特殊应用，单官能起始剂也可包含在聚醚结构中。
合适的环氧烷烃包括，例如四氢呋喃、1,3-环氧丙烷、1,2-环氧丁烷、2,3-环氧丁烷、氧化苯乙烯且优选环氧乙烷和1,2-环氧丙烷。环氧烷烃可以单独使用，交替接连使用或作为混合物使用。
有用的起始分子包括，例如：水，脂族和芳族的在烷基部分具有1至4个碳原子的任选N-单烷基取代、N,N-和N,N'-二烷基取代的二胺(如任选单烷基和二烷基取代的乙二胺)，二亚乙基三胺，三亚乙基四胺，1,3-丙二胺，1,3-丁二胺，1,4-丁二胺，1,2-六亚甲基二胺，1,3-六亚甲基二胺，1,4-六亚甲基二胺，1,5-六亚甲基二胺，1,6-六亚甲基二胺，苯二胺，2,3-、2,4-和2,6-甲苯二胺(TDA)，以及4,4'-、2,4'-和2,2'-二氨基二苯基甲烷(MDA)和聚合MDA。有用的起始分子还包括链烷醇胺，例如乙醇胺、N-甲基乙醇胺和N-乙基乙醇胺；二链烷醇胺，例如二乙醇胺、N-甲基二乙醇胺和N-乙基二乙醇胺；三链烷醇胺，例如三乙醇胺；以及氨。优选使用多元醇(polyhydric alcohol)，例如乙二醇、1,2-丙二醇、2,3-丙二醇、二乙二醇、二丙二醇、1,4-丁二醇、1,6-己二醇、丙三醇、三羟甲基丙烷、季戊四醇、山梨糖醇和蔗糖及其混合物。聚醚多元醇可以单独使用或以混合物的形式使用。
有用的其他聚酯醇C包括在聚氨酯化学中常用的聚酯醇。聚酯醇C可例如由具有2至12个碳原子的有机二羧酸、优选具有4至6个碳原子的脂族二羧酸和具有2至12个碳原子、优选2至6个碳原子的多元醇、优选二醇获得。有用的二羧酸包括，例如琥珀酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、癸烷二羧酸、马来酸、富马酸、邻苯二甲酸、间苯二甲酸和对苯二甲酸。在本文中，二羧酸不仅可以单独使用，也可以彼此混合使用。代替游离二羧酸，也可以使用相应的二羧酸衍生物，例如具有1至4个碳原子的醇的二羧酸酯或者二羧酸酐。优选使用琥珀酸、戊二酸和己二酸以数量比为例如(20至35):(35至50):(20至32)重量份的混合物，特别是己二酸。二元醇和多元醇、特别是二元醇的实例是乙二醇、二乙二醇、1,2-丙二醇、1,3-丙二醇、二丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,10-癸二醇、丙三醇和三羟甲基丙烷。优选使用乙二醇、二乙二醇、1,4-丁二醇、1,5-戊二醇和1,6-己二醇。还可以使用由内酯(例如己内酯)或羟基羧酸(例如羟基己酸)形成的聚酯多元醇。
聚酯多元醇可通过使有机(例如芳族且优选脂族)多羧酸和/或其衍生物与多元醇在下述条件下缩聚至所需的酸值(其优选小于10且更优选小于2)来获得，即在不使用催化剂或优选在酯化催化剂的存在下，有利地在惰性气体例如氮气、一氧化碳、氦气、氩气等气氛中，在150至250℃、优选180至220℃的熔体中，任选地在减压条件下。在一个优选的实施方案中，在大气压下，然后在小于500毫巴、优选50至150毫巴的压力下，在上述温度下将酯化混合物缩聚至酸值为80至30、优选40至30。有用的酯化催化剂包括例如金属、金属氧化物或金属盐形式的铁、镉、钴、铅、锌、锑、镁、钛和锡催化剂。然而，缩聚也可以在液相中在稀释剂和/或夹带剂物质(例如苯、甲苯、二甲苯或氯苯)存在下进行，以共沸蒸馏出缩合水。用于形成聚酯多元醇的有机多羧酸和/或其衍生物与多元醇之间的摩尔比有利地在1:1至1.8的范围内，优选在1:1.05至1.2的范围内。
所获得的聚酯多元醇的官能度优选为2至4、尤其是2至3，且数均分子量为480至3000、优选为1000至3000g/mol。
当将催化剂D用于制备聚氨酯时，其优选是化合物，并且对组分B和任选的C的含羟基化合物与有机、任选改性的多异氰酸酯A的反应具有显著加速的作用。实例包括：脒如2,3-二甲基-3,4,5,6-四氢嘧啶；叔胺如三乙胺、三丁胺、二甲基苄胺、N-甲基吗啉、N-乙基吗啉、N-环己基吗啉、N,N,N',N'-四甲基乙二胺、N,N,N',N'-四甲基丁二胺、N,N,N',N'-四甲基己二胺、五甲基二亚乙基三胺、四甲基二氨基乙基醚、双(二甲基氨基丙基)脲、二甲基哌嗪、1,2-二甲基咪唑、1-氮杂双环(3,3,0)辛烷、优选1,4-二氮杂双环(2,2,2)辛烷；和链烷醇胺化合物如三乙醇胺、三异丙醇胺、N-甲基二乙醇胺和N-乙基二乙醇胺及二甲基乙醇胺。还考虑的是有机金属化合物，优选有机锡化合物，例如有机羧酸的锡(II)盐如乙酸锡(II)、辛酸锡(II)、乙基己酸锡(II)和月桂酸锡，和有机羧酸的二烷基锡(IV)盐如二乙酸二丁基锡、二月桂酸二丁基锡、马来酸二丁基锡和二乙酸二辛基锡；以及羧酸铋，例如新癸酸铋(III)、2-乙基己酸铋和辛酸铋；或它们的混合物。有机金属化合物可以单独使用或优选与强碱性胺结合使用。
催化剂或催化剂组合的用量优选为0.001至5重量％且尤其为0.05至2重量％，基于组分B和任选的C的总重量计。
聚氨酯弹性体可以是密度通常大于1000kg/m3的非多孔的致密材料，或者是泡沫。泡沫优选通过下述过程制备：用水(组分E)发泡，水与异氰酸酯基团反应释放出二氧化碳。也可以将所谓的物理发泡剂与水结合使用或者代替水使用。物理发泡剂对原料组分呈惰性，在室温下通常为液体，并在氨基甲酸酯反应的条件下蒸发。其沸点优选低于100℃。
物理发泡剂F通常选自具有至少4个碳原子的烷烃和/或环烷烃、二烷基醚、酯、醇、酮、缩醛、具有1至8个碳原子的氟烷烃和四烷基硅烷。
实例包括丙烷、正丁烷、异丁烷、环丁烷、正戊烷、异戊烷、环戊烷、环己烷、二甲醚、甲基乙基醚、甲基丁基醚、甲酸甲酯、叔丁醇、丙酮，以及在对流层中分解并因此对臭氧层无害的氟烷烃例如三氟甲烷、二氟甲烷、1,1,1,3,3-五氟丁烷、1,1,1,3,3-五氟丙烷、1,1,1,2,3-五氟丙烯、1-氯-3,3,3-三氟丙烯、1,1,1,2-四氟乙烷、二氟乙烷和1,1,1,2,3,3,3-七氟丙烷以及全氟烷烃(例如C3F8、C4F10、C5F12、C6F14和C7F17)。特别优选烃，优选戊烷，特别是环戊烷。所述物理发泡剂可以单独使用或彼此以任何所需的组合使用。
当使用水作为唯一的发泡剂时，水的量优选在0.05至3重量份的范围内，基于多元醇组分B和任选的C计。当使用物理发泡剂时，其量优选在0.1至10重量份的范围内，基于多元醇组分B和任选的C计。
泡沫通常在模具中制备。泡沫密度通常在100至1000kg/m3的范围内。这类泡沫在技术文献中有时被称为微孔泡沫。
用于制备聚氨酯泡沫的反应混合物也可任选地与助剂和/或添加剂E混合。助剂和/或添加剂E的实例包括表面活性物质、泡沫稳定剂、泡孔调节剂、其他脱模剂、填料、染料、颜料、水解控制剂、阻燃剂、气味吸收物质以及抑制真菌和/或抑制细菌的活性物质。
有用的表面活性物质包括例如用于增大原料的均匀化度并且也可适于调节泡孔结构的化合物。实例为乳化剂，例如蓖麻油硫酸酯的钠盐或脂肪酸的钠盐、以及脂肪酸与胺的盐(例如油酸二乙胺、硬脂酸二乙醇胺、蓖麻醇酸二乙醇胺)、磺酸的盐(例如十二烷基苯二磺酸或二萘基甲烷二磺酸的碱金属盐或铵盐)、以及蓖麻油酸的盐；泡沫稳定剂，例如硅氧烷-氧亚烷基互聚物和其他有机聚硅氧烷、乙氧基化烷基酚、乙氧基化脂肪醇、石蜡油、蓖麻油酯或更准确地为蓖麻油酸酯、土耳其红油(Turkey red oil)和花生油；以及泡孔调节剂，例如链烷烃(paraffin)、脂肪醇和二甲基聚硅氧烷。为了改善乳化效果、泡沫的泡孔结构和/或稳定性，还可以使用具有聚氧亚烷基部分和氟烷烃部分作为侧基的低聚丙烯酸酯。表面活性物质的用量通常为0.01至5重量份，基于100重量份的组分B和任选的C计。
有用的其他脱模剂包括例如：脂肪酸酯与多异氰酸酯的反应产物、含氨基的聚硅氧烷与脂肪酸的盐、具有至少8个碳原子的饱和或不饱和(环)脂族羧酸与叔胺的盐；以及，更特别地，内脱模剂，例如通过使以下混合物酯化或酰胺化制备的羧酸酯和/或酰胺：褐煤酸和至少一种具有至少10个碳原子的脂族羧酸与至少双官能的链烷醇胺、分子量为60-400g/mol的多元醇和/或多胺的混合物，如EP153639中所公开的；有机胺、硬脂酸的金属盐、和有机单和/或二羧酸或有机单和/或二羧酸酸酐的混合物，如DE-A-3 607 447中所公开的；或者亚氨基化合物、羧酸的金属盐和任选的羧酸的混合物，如US 4 764 537中所公开的。优选地，本发明的反应混合物不包含任何其他脱模剂。
有用的填料，尤其是增强填料，包括常规的熟知的有机和无机填料、增强剂、增重剂、涂布剂等。具体的实例为无机填料，例如：硅石矿物，如片状硅酸盐，如叶蛇纹石、膨润土、蛇纹石、角闪石(horn blend)，闪石(amphibol)、硅镁石(chrisotile)和滑石；金属氧化物，如高岭土、氧化铝、氧化钛、氧化锌和氧化铁；金属盐，如白垩和重晶石；以及无机颜料，如硫化镉、硫化锌、以及玻璃等。优选使用高岭土(瓷土)、硅酸铝以及硫酸钡和硅酸铝的共沉淀物。也可以添加无机纤维，例如玻璃纤维。有用的有机填料包括例如炭黑、三聚氰胺、松香、环戊二烯基树脂和接枝聚合物以及纤维素纤维、聚酰胺纤维、聚丙烯腈纤维、聚氨酯纤维、基于芳族和/或脂族二羧酸酯的聚酯纤维，尤其是碳纤维。
有机和无机填料可以单独使用或作为混合物使用，并且有利地添加到反应混合物中的量为0.5至50重量％、优选1至40重量％，基于组分A至D的重量计。
由此获得的聚氨酯具有多种可能的用途。主要的使用领域描述在“ThePolyurethanes Book”,Randall和Lee(编辑),Wiley,2010,ISBN978-0-470-85041-1,第19至22章中。
热塑性聚氨酯是这样的可熔融聚氨酯，其在常规热塑处理操作例如挤出、压延和注塑中加工成例如薄膜/片材、软管、电缆护套和用于车辆工业的高价值组件。
微孔聚氨酯弹性体用于例如鞋类以及用于汽车工业的过载弹簧和整体泡沫。
可浇铸聚氨酯弹性体用于例如制造辊、筛、过滤器、工业地板和运动地板。
RIM弹性体用在例如盘和窗口卷边(window beading)中以及用于制造汽车组件，例如挡泥板和扰流板。
聚氨酯弹性体可用于制备弹性体涂料。
聚氨酯弹性体可用于制备弹性体纤维。
聚氨酯弹性体可用于制备胶粘剂。
以下实施例说明本发明。
实施例
表1示出了基于聚丁二烯的可能的多元醇的概述。多元醇4是后官能化的聚丁二烯。表1还列出了纯聚己内酯聚酯(
2200，PerstorpHolding，Perstorp，Sweden)作为多元醇5。
实施例1：多元醇4的制备
在10L圆锥形钢制反应器中，将680g
PM4(来自Synthomer，Essex，UK)溶解在3850g甲苯中并加热至60℃。在加入59.5g的98重量％的甲酸后，将内容物在400rpm下充分混合。过氧化氢以40mL/h的量连续加入，持续7.5小时。然后，将反应混合物用饱和碳酸氢钠溶液洗涤两次，并用饱和氯化钠溶液洗涤一次。有机相用硫酸钠进行干燥，并在60℃下减压除去溶剂。
双键的转化率：6.9％；依照Jung&Kleeberg的环氧值：0.104mol环氧基/100g聚合物；颜色：淡黄色；粘度：0.687Pa·s(40℃)
在6L玻璃反应器中，将520g环氧化的
PM4分散在2080g 1-丙醇中并加热至65℃。在加入1.56mL 10重量％的三氟甲磺酸于1-丙醇中的溶液(100ppm)后，将内容物搅拌6小时。混合物用碳酸氢钠中和，冷却并过滤。将丙醇在最高达95℃下在减压下从滤液中除去。
OH值：52.11；颜色：淡黄色；粘度：1.09Pa·s(40℃)
所用的其他多元醇描述于表1中。
表1：羟基官能化的聚丁二稀
聚酯改性的多元醇组分的制备
将ε-己内酯经由CaH2干燥，然后在130℃下减压蒸馏，在-30℃下在氩气下储存，并在14天内使用。将四丁氧基钛以50体积％溶解在无水甲苯中，并将溶液在氩气下储存。
实施例2：多元醇6至10的制备
将所用的聚丁二烯在95℃下真空干燥20小时，并在使用前储存在氩气下。向250mL玻璃反应器中加入164g多元醇1(157mmol OH基团)和36gε-己内酯(315mmol)并吹入氩气。将组分搅拌均匀，加热至120℃，最后与43μL四丁氧基钛溶液(15ppm钛)混合，然后将反应器密封。在120℃下搅拌2小时后，将产物排出。
表2a中的多元醇7至10以类似于多元醇6的方式制备。初始重量差和相关产物性质总结于表2a中。
表2a：酯改性的多元醇组分的制备
实施例3：多元醇11至13的制备
在5L钢制反应器中，将1367.4g多元醇3(1.28mol OH基团)在100℃下真空干燥3小时，并在氮气条件下与462.7gε-己内酯(4.06mol)混合。将组分在250rpm和150℃下搅拌均匀，然后与0.40ml四丁氧基钛溶液(15ppm钛)混合，并将反应器密封。在150℃下搅拌4小时后，将产物排出。
表2b中的多元醇12和13以类似于多元醇11的方式制备。初始重量差和相关产物性质总结在表2b中。
表2b：酯改性的多元醇组分的制备
聚氨酯弹性体的制备
将多元醇组分和异氰酸酯温度控制至45℃和/或60℃，以加工成聚氨酯。该温度取决于多元醇组分的熔融温度。除了聚丁二烯多元醇之外的多元醇组分包含1,4-丁二醇作为增链剂、汞盐作为催化剂以及消泡剂(Antifoam MSA，来自Dow Corning)。所用的B组分是由相等份的以下物质形成的混合物：市售可得的NCO值为23％的基于4,4'-MDI的预聚物(来自BASF的MP102)和市售可得的脲酮亚胺改性的4,4'-MDI(来自BASF的MM103)。将聚氨酯弹性体配方全部调整到NCO指数为100。一个混合过程包括将组分在来自Hausschild的Speedmixer中以2000rpm混合1分钟。
实施例4：弹性体1至11的制备
以弹性体2的制备为例，称量90.07g多元醇6(多元醇组分的95.2％)作为多元醇组分加入到烧杯中，并加入3.79g 1,4-丁二醇(多元醇组分的4.0％)、0.47g催化剂(多元醇组分的0.5％)和0.28g消泡剂(多元醇组分的0.3％)，温度在45℃(加工温度)控制30分钟。将该组分在Speedmixer中混合2分钟，直到无气泡。然后与异氰酸酯组分在Speedmixer中混合1分钟。将混合物倒入150×200×2mm3的模具中，温度控制在80℃，并用塑料杆将其捋平。30分钟后，将浇注弹性体脱模并使其处于80℃下4小时。将聚氨酯弹性体在23℃和50％相对湿度下储存至少7天，然后进行表征。
弹性体1和3至11以类似于弹性体2的方式获得。基于其他HTPB多元醇获得的弹性体的初始重量差和相关产物性质根据加工温度总结在表3a和3b中。
表3a：在45℃的加工温度下由未改性多元醇制备聚氨酯弹性体
表3b：在60℃的加工温度下由酯改性多元醇制备聚氨酯弹性体
比较实施例1：弹性体12的制备
根据实施例4，由纯聚己内酯多元醇(表1中的多元醇5)形成聚氨酯弹性体，以进行比较。表4总结了该弹性体的配方和机械性能。
表4：在60℃的处理温度下，由纯的聚己内酯生产聚氨酯弹性体
| 名称 | 弹性体12 |
| 多元醇 | 多元醇5 |
| 多元醇中的ε-己内酯[重量％] | 100 |
| 多元醇[％] | 95.6 |
| 丁二醇[％] | 4 |
| 消泡剂[％] | 0.3 |
| 催化剂[％] | 0.1 |
| 肖氏A | 58 |
| 断裂伸长率[％] | 470 |
| 拉伸强度[MPa] | 30 |
| 溶胀度[％] | 1.39 |
所提供的实施例表明，聚丁二烯醇用聚己内酯的嵌段接枝导致机械性能显著改善。尽管用己内酯改性，但聚氨酯弹性体在水中的溶胀度还是非常低。
实施例5：TPU1的制备
将多元醇组分13和异氰酸酯分别控制温度在70℃和45℃，以加工成热塑性聚氨酯(TPU)。除了聚丁二烯多元醇外的多元醇组分包含1,4-丁二醇作为增链剂。所用的异氰酸酯组分是4,4-MDI。将配方调整至NCO指数为100。
混合使用来自Heidolph的顶式搅拌器在220rpm下进行。
所述多元醇组分通过以下过程提供：称量1420.11g多元醇13(多元醇组分的91.27％)、124.48g 1,4-丁二醇(多元醇组分的8.0％)一起加入到桶式容器中，随后在70℃下储存2小时。然后加入444.06g纯4,4'-MDI。将这些组分混合，直至反应混合物达到80℃。然后将物料倒入铝壳中，温度控制在80℃。在总共10分钟后，使TPU处于80℃下15小时。
试样的制备
将获得的TPU切成约15×10cm2大小的片，将其用液氮冷却。将冷却的样品用Condux切碎机粉碎成粒料。将该粒料用于来自ChristmannKunststofftechnik GmbH的Babyplast(模型6/10)上，通过注塑成型(塑化：211℃，十字头室：215℃，模头：210℃，模具：64℃)形成3cm×7cm尺寸的试样。随后切出S2肩棒(shoulder bar)。机械性能总结在表5中。
表5：由酯改性多元醇制备TPU
| 名称 | TPU 1 |
| 多元醇 | 多元醇13 |
| 多元醇中的ε-己内酯[重量％] | 30 |
| 多元醇[％] | 91.27 |
| 丁二醇[％] | 8 |
| 肖氏A | 75 |
| 断裂伸长率[％] | 471.7 |
| 拉伸强度[MPa] | 13.3 |
| 溶胀度[％] | 0.45 |
比较实施例2：由未改性的聚丁二烯二醇制备TPU
类似于实施例5，使用未改性的聚丁二烯二醇(多元醇1)进行实验，得到具有非常低强度的材料。该材料未作进一步处理。
表征
聚丁二烯环氧化中双键的转化通过1H NMR光谱在氘代氯仿中测定。环氧化的聚丁二烯的EP值通过Jung&Kleeberg[Fres.J.Anal.Chem.1962,387]的方法测定。
多元醇的OH值根据DIN 53240-2通过电位滴定测定。
动态剪切粘度用来自TA Instruments的AR-G2流变仪测定。测量在规定温度下在稳态模式下在0.1至1000Hz的剪切频率下采用锥板式几何结构(直径：40mm或60mm，角度：2°)进行。
熔融温度通过DSC测定。将样品以20℃/min的速率从室温加热至150℃。该温度保持3分钟。使温度以10℃/min的速率最终冷却至-120℃，然后在3分钟的延迟时间后以10℃/min的速率加热至220℃。熔点在第二加热阶段测定。将该温度再次保持3分钟，然后最终冷却至室温。
拉伸试验根据DIN 53504在具有光程跟踪的S2肩棒上进行。
肖氏硬度根据DIN 53505测定。
吸水性在约3×4cm2尺寸(切割以适合滑动框架)的PU板上测定。将样品置于100℃水中5小时。最后，将样品轻轻擦干后，由重量差计算出溶胀度。
Claims (5)
1.一种聚氨酯，其可通过以下物质的反应获得：
a)30至150重量份的多异氰酸酯A，选自任选改性的4,4'-甲烷二苯基二异氰酸酯、4,4'-甲烷二苯基二异氰酸酯的更高级核同系物、基于4,4'-甲烷二苯基二异氰酸酯的含异氰酸酯基团的预聚物以及它们的混合物，与
b)具有至少两个异氰酸酯反应性氢原子的化合物，其包含
b1)100重量份的由聚丁二烯醇和环酯形成的嵌段共聚物，作为组分B1，其中环酯为ε-己内酯且其在B1中的比例为10至35重量％，以及
b2)4至15重量份的作为低分子量增链剂的二醇和任选的作为交联剂的三醇，所述二醇和三醇分子量为62至500g/mol，作为组分B2，
c)0至100重量份的具有至少2个异氰酸酯反应性氢原子的其他聚合化合物C，
d)0至5重量份的催化剂D，
e)0至3重量份的水E，
f)0至10重量份的物理发泡剂F，
g)0至100重量份的其他助剂和/或添加剂G。
2.根据权利要求1所述的聚氨酯，其中多元醇组分B1的数均分子量在600至15000g/mol的范围内，OH官能度为2至5。
3.根据权利要求1所述的聚氨酯，其中多元醇组分B1的数均分子量在600至15000g/mol的范围内，OH官能度为1.5至2.2。
4.根据权利要求1所述的聚氨酯，其中组分B2的增链剂选自乙二醇、1,2-丙二醇、1,3-丙二醇、2-甲基-1,3-丙二醇、1,4-丁二醇、二乙二醇和二丙二醇。
5.根据权利要求4所述的聚氨酯，其中组分B2的交联剂选自乙氧基化甘油和/或丙氧基化甘油和三羟甲基丙烷。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14181297 | 2014-08-18 | ||
| EP14181297.4 | 2014-08-18 | ||
| PCT/EP2015/068837 WO2016026807A1 (de) | 2014-08-18 | 2015-08-17 | Polyestermodifizierte polybutadienole zur herstellung von polyurethan-elastomeren und thermoplastischen polyurethanen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107075078A CN107075078A (zh) | 2017-08-18 |
| CN107075078B true CN107075078B (zh) | 2022-01-04 |
Family
ID=51352465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201580056393.0A Active CN107075078B (zh) | 2014-08-18 | 2015-08-17 | 用于制备聚氨酯弹性体和热塑性聚氨酯的聚酯改性的聚丁二烯醇 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US11066508B2 (zh) |
| EP (1) | EP3183282B1 (zh) |
| JP (1) | JP2017525814A (zh) |
| KR (1) | KR20170043598A (zh) |
| CN (1) | CN107075078B (zh) |
| BR (1) | BR112017003310A2 (zh) |
| WO (1) | WO2016026807A1 (zh) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107109277B (zh) * | 2015-03-19 | 2019-10-25 | 日立江森自控空调有限公司 | 制冷空调用压缩机和制冷空调装置 |
| US10266644B2 (en) * | 2015-04-06 | 2019-04-23 | Nisshinbo Chemical Inc. | Epoxy resin composition |
| EP3433295B1 (de) * | 2016-03-21 | 2020-08-26 | Basf Se | Vernetztes polyurethan |
| EP3243863A1 (de) * | 2016-05-09 | 2017-11-15 | Evonik Degussa GmbH | Verwendung von block-copolymeren in klebstoffen |
| EP3480231A1 (de) | 2017-11-03 | 2019-05-08 | Evonik Degussa GmbH | Reaktivklebstoffe basierend auf block-copolymeren |
| KR102649156B1 (ko) * | 2018-08-02 | 2024-03-20 | 다우 글로벌 테크놀로지스 엘엘씨 | 폴리우레탄 폼에서 알데히드 방출을 감소시키는 방법 |
| EP3653658A1 (en) | 2018-11-16 | 2020-05-20 | Henkel AG & Co. KGaA | Thermoplastic polyurethane |
| EP3898721B1 (en) | 2018-12-19 | 2023-05-03 | Evonik Operations GmbH | Viscosity index improvers based on block copolymers |
| KR20210135584A (ko) | 2019-03-07 | 2021-11-15 | 바스프 에스이 | 카르보디아미드 화학 기반의 접착제 |
| CN110256652A (zh) * | 2019-06-12 | 2019-09-20 | 西安近代化学研究所 | 一种适应温度范围广的高弹性缓冲材料 |
| WO2021050622A1 (en) * | 2019-09-10 | 2021-03-18 | Lubrizol Advanced Materials, Inc. | Thermoplastic polyurethane composition |
| CN111269382B (zh) * | 2020-01-20 | 2021-12-28 | 扬州工业职业技术学院 | 防卷边低凝固速率pu树脂及其制备方法 |
| CN111469365A (zh) * | 2020-03-30 | 2020-07-31 | 广东维杰汽车部件制造有限公司 | 汽车扰流板的反应注射成型工艺 |
| EP3919539A1 (de) * | 2020-06-04 | 2021-12-08 | Evonik Operations GmbH | Herstellung von polyurethanschaum |
| CN114163666A (zh) * | 2021-10-26 | 2022-03-11 | 上海交通大学 | 推进剂用可闭环回收的聚丁二烯弹性体的制备方法及其应用 |
| WO2023247278A1 (de) | 2022-06-22 | 2023-12-28 | Basf Se | Epoxy-terminierte isocyanat-prepolymere und verfahren zu deren herstellung |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023418A (ja) * | 1983-07-20 | 1985-02-06 | Daicel Chem Ind Ltd | 新規なラクトン重合体の製造方法 |
| US4689357A (en) * | 1984-07-30 | 1987-08-25 | Nisshin Spinning Co., Ltd. | Vibration isolator |
| WO2013180006A1 (ja) * | 2012-05-30 | 2013-12-05 | 日本曹達株式会社 | ポリウレタン |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE154609C (zh) | ||||
| DE159775C (de) | 1908-01-23 | 1905-04-27 | Duisberger Maschinenbau-Akt-Ges | Antriebsvorrichtung fuer Rollgaenge |
| NL7217047A (zh) * | 1972-12-15 | 1974-06-18 | ||
| US3965140A (en) | 1973-07-28 | 1976-06-22 | The Yokohama Rubber Co. Ltd. | Process for the preparation of hydroxyl-terminated liquid polymers |
| US4190712A (en) * | 1974-06-21 | 1980-02-26 | Mccord Corporation | Low density energy management urethane foam |
| DD160223A3 (de) | 1975-04-29 | 1983-05-18 | Winfried Ballayer | Verfahren zur herstellung von praepolymeren mit entstaendigen hydroxylgruppen |
| JPS55152720A (en) * | 1979-05-18 | 1980-11-28 | Mitsubishi Chem Ind Ltd | Block copolymer and preparation of the same |
| DE3405875A1 (de) | 1984-02-18 | 1985-08-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von zelligen oder kompakten polyurethan-polyharnstoff-formkoerpern mit verbesserten entformungseigenschaften sowie innere formtrennmittel fuer das polyisocyanat-polyadditionsverfahren |
| DE3607447A1 (de) | 1986-03-07 | 1987-09-10 | Basf Ag | Verfahren zur herstellung von formkoerpern mit einem zelligen kern und einer verdichteten randzone mit verbesserten entformungseigenschaften |
| DE3631842A1 (de) | 1986-09-19 | 1988-03-24 | Basf Ag | Innere formtrennmittel, deren verwendung zur herstellung von formkoerpern nach dem polyisocyanat-polyadditionsverfahren und verfahren zur herstellung der formkoerper |
| JP2760499B2 (ja) | 1986-11-05 | 1998-05-28 | 三菱レイヨン 株式会社 | トナー用樹脂及びその製造法 |
| EP0266973A3 (en) * | 1986-11-06 | 1990-01-10 | Thiokol Corporation | Pcp/htpb block copolymer and propellant binder prepared therefrom |
| JPH0627188B2 (ja) * | 1986-11-07 | 1994-04-13 | 竹本油脂株式会社 | 合成樹脂材料用改質剤 |
| DE3837351C1 (zh) * | 1988-11-03 | 1989-11-23 | Th. Goldschmidt Ag, 4300 Essen, De | |
| US6350330B1 (en) * | 1989-06-07 | 2002-02-26 | Alliant Techsystems Inc. | Poly(butadiene)poly(lactone) thermoplastic block polymers, methods of making, and uncured high energy compositions containing same as binders |
| US5167899A (en) * | 1990-07-07 | 1992-12-01 | The Dow Chemical Company | Process for melt blowing microfibers of rigid polyurethane having hard segments |
| DE4115146A1 (de) | 1991-05-08 | 1992-11-12 | Henkel Kgaa | Verfahren zur herstellung von epoxid-ringoeffnungsprodukten mit einem definierten rest-epoxidsauerstoffgehalt |
| US5242989A (en) | 1992-04-03 | 1993-09-07 | Shell Oil Company | Hydroxyl functional derivatives of epoxidized diene polymers and process for making them |
| WO1995011927A1 (en) * | 1993-10-26 | 1995-05-04 | Lord Corporation | Polyester-modified polydiene/acrylourethane oligomers |
| DE4446877A1 (de) | 1994-12-27 | 1996-07-04 | Henkel Kgaa | Verfahren zur Ringöffnung von Epoxiden |
| US6111049A (en) * | 1996-02-09 | 2000-08-29 | Shell Oil Company | Polyurethanes having improved moisture resistance |
| US6054533A (en) * | 1997-10-15 | 2000-04-25 | The B.F. Goodrich Company | Compatibilized blends of a thermoplastic elastomer and a polyolefin |
| GB9810040D0 (en) | 1998-05-11 | 1998-07-08 | Univ Nottingham | Blood borne tumour markers |
| DE102005015635A1 (de) * | 2005-04-05 | 2006-10-12 | Basf Ag | Polyurethangummi |
| CN100460437C (zh) * | 2006-08-11 | 2009-02-11 | 中国石油天然气集团公司 | 高性能多用途聚氨酯弹性体的合成方法 |
| CN101868487A (zh) * | 2007-09-21 | 2010-10-20 | 陶氏环球技术公司 | 聚氨酯聚合物体系 |
| JP5842315B2 (ja) * | 2008-12-01 | 2016-01-13 | 三菱化学株式会社 | ポリウレタンの製造方法及びそれから得られたポリウレタンの用途 |
| CN103965433B (zh) * | 2014-05-24 | 2016-03-23 | 浙江奥康鞋业股份有限公司 | 鞋底用软质低密度聚氨酯泡沫材料 |
-
2015
- 2015-08-17 BR BR112017003310A patent/BR112017003310A2/pt active Search and Examination
- 2015-08-17 CN CN201580056393.0A patent/CN107075078B/zh active Active
- 2015-08-17 WO PCT/EP2015/068837 patent/WO2016026807A1/de active Application Filing
- 2015-08-17 US US15/504,493 patent/US11066508B2/en active Active
- 2015-08-17 KR KR1020177007305A patent/KR20170043598A/ko not_active Application Discontinuation
- 2015-08-17 JP JP2017510329A patent/JP2017525814A/ja not_active Ceased
- 2015-08-17 EP EP15756586.2A patent/EP3183282B1/de not_active Not-in-force
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023418A (ja) * | 1983-07-20 | 1985-02-06 | Daicel Chem Ind Ltd | 新規なラクトン重合体の製造方法 |
| US4689357A (en) * | 1984-07-30 | 1987-08-25 | Nisshin Spinning Co., Ltd. | Vibration isolator |
| WO2013180006A1 (ja) * | 2012-05-30 | 2013-12-05 | 日本曹達株式会社 | ポリウレタン |
Also Published As
| Publication number | Publication date |
|---|---|
| US11066508B2 (en) | 2021-07-20 |
| US20170240684A1 (en) | 2017-08-24 |
| WO2016026807A1 (de) | 2016-02-25 |
| CN107075078A (zh) | 2017-08-18 |
| KR20170043598A (ko) | 2017-04-21 |
| JP2017525814A (ja) | 2017-09-07 |
| EP3183282B1 (de) | 2018-08-15 |
| BR112017003310A2 (pt) | 2018-01-23 |
| EP3183282A1 (de) | 2017-06-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107075078B (zh) | 用于制备聚氨酯弹性体和热塑性聚氨酯的聚酯改性的聚丁二烯醇 | |
| US10428173B2 (en) | High strength polyurethane foam compositions and methods | |
| CN108779230B (zh) | 交联聚氨酯 | |
| JP5649981B2 (ja) | 粗い気泡のポリウレタンエラストマー | |
| TWI454527B (zh) | 聚胺基甲酸酯樹脂組成物及其成形物 | |
| US20090270582A1 (en) | Hyper-branched polyurethanes method for production and use thereof | |
| JPWO2005116102A1 (ja) | ポリウレタンエラストマーおよびその製造方法 | |
| EP3265495B1 (de) | Polybutadienole zur herstellung von glasartigen polyurethanen | |
| TWI648340B (zh) | 熱塑性聚胺基甲酸酯、其製造及用途 | |
| WO2013138161A1 (en) | Polymer compositions and methods | |
| KR20190126312A (ko) | 우레탄 함유 중합체 히드록실 화합물에 기반한 낮은 블루밍 효과 및 우수한 저온 가요성을 나타내는 폴리우레탄의 제조 방법 | |
| KR20160057617A (ko) | 친환경 폴리우레탄 수지 조성물 | |
| WO2021012985A1 (en) | Polyurethane compositions, products prepared with same and preparation methods thereof | |
| CN111527117A (zh) | 聚氨酯杂化聚合物及其制备方法 | |
| EP4017891B1 (en) | A preparation comprising thermoplastic polyisocyanate polyaddition product, a process for preparing the same and the use thereof | |
| KR20200145584A (ko) | 고탄성연질폴리우레탄폼개발 | |
| WO2022011580A1 (en) | Polyester polyol-polyether polyol blend having higher stability and comparibility, and polyurethane material prepared therefrom |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |