CN1104451C - 致密或多孔聚氨酯弹性体的生产方法及适合于此目的的异氰酸酯预聚物 - Google Patents
致密或多孔聚氨酯弹性体的生产方法及适合于此目的的异氰酸酯预聚物 Download PDFInfo
- Publication number
- CN1104451C CN1104451C CN97196259A CN97196259A CN1104451C CN 1104451 C CN1104451 C CN 1104451C CN 97196259 A CN97196259 A CN 97196259A CN 97196259 A CN97196259 A CN 97196259A CN 1104451 C CN1104451 C CN 1104451C
- Authority
- CN
- China
- Prior art keywords
- vulcabond
- isocyanate group
- prepolymer
- hydroxyl
- diisocyanate
- 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.)
- Expired - Fee Related
Links
- 239000012948 isocyanate Substances 0.000 title claims abstract description 25
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 23
- 229920003225 polyurethane elastomer Polymers 0.000 title claims abstract description 8
- 230000001413 cellular effect Effects 0.000 title abstract description 3
- 238000004519 manufacturing process Methods 0.000 title description 21
- 238000000034 method Methods 0.000 claims abstract description 53
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 239000000654 additive Substances 0.000 claims abstract description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 69
- -1 polyoxy Polymers 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 59
- 239000003795 chemical substances by application Substances 0.000 claims description 55
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 46
- 229920005862 polyol Polymers 0.000 claims description 40
- 150000003077 polyols Chemical class 0.000 claims description 40
- 239000004970 Chain extender Substances 0.000 claims description 32
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000003368 amide group Chemical group 0.000 claims description 12
- 229920005906 polyester polyol Polymers 0.000 claims description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 229920000515 polycarbonate Polymers 0.000 claims description 9
- 239000004417 polycarbonate Substances 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- GVEDOIATHPCYGS-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)benzene Chemical group CC1=CC=CC(C=2C=C(C)C=CC=2)=C1 GVEDOIATHPCYGS-UHFFFAOYSA-N 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims 1
- 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 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 4
- 229920001971 elastomer Polymers 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- 239000000806 elastomer Substances 0.000 abstract description 2
- 239000004088 foaming agent Substances 0.000 abstract description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 abstract 1
- KAEIHZNNPOMFSS-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1CCC1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1CCC1=CC=CC=C1 KAEIHZNNPOMFSS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 description 70
- 230000000052 comparative effect Effects 0.000 description 23
- 239000000047 product Substances 0.000 description 21
- 150000001721 carbon Chemical group 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 15
- 230000003068 static effect Effects 0.000 description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000013016 damping Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 7
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 7
- 238000000280 densification Methods 0.000 description 7
- 230000002349 favourable effect Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 238000013461 design Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 239000001361 adipic acid Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 239000003063 flame retardant Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- 238000006068 polycondensation reaction Methods 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-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
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 238000009998 heat setting Methods 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- 229940051250 hexylene glycol Drugs 0.000 description 3
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 3
- 239000012766 organic filler Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000012763 reinforcing filler Substances 0.000 description 3
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-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
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- 239000004114 Ammonium polyphosphate Substances 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000063973 Mattia Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 2
- 229920001276 ammonium polyphosphate Polymers 0.000 description 2
- 150000003863 ammonium salts 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
- 239000012298 atmosphere Substances 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- DGXRZJSPDXZJFG-UHFFFAOYSA-N docosanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCCCCCC(O)=O DGXRZJSPDXZJFG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000012764 mineral filler Substances 0.000 description 2
- QATBRNFTOCXULG-UHFFFAOYSA-N n'-[2-(methylamino)ethyl]ethane-1,2-diamine Chemical compound CNCCNCCN QATBRNFTOCXULG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 2
- 229960004418 trolamine Drugs 0.000 description 2
- 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
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- IHHUGFJSEJSCGE-UHFFFAOYSA-N 1-isocyanato-2-phenylbenzene Chemical group O=C=NC1=CC=CC=C1C1=CC=CC=C1 IHHUGFJSEJSCGE-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
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- YRTNMMLRBJMGJJ-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;hexanedioic acid Chemical compound OCC(C)(C)CO.OC(=O)CCCCC(O)=O YRTNMMLRBJMGJJ-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical group 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
- YZGMIRBFYCQNRH-UHFFFAOYSA-N 2-(2-hydroxyethyl)benzene-1,3-diol Chemical compound OCCC1=C(O)C=CC=C1O YZGMIRBFYCQNRH-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
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- IIVBUJGYWCCLNG-UHFFFAOYSA-N 3-(dimethylamino)propylurea Chemical compound CN(C)CCCNC(N)=O IIVBUJGYWCCLNG-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- KZTROCYBPMKGAW-UHFFFAOYSA-N 4-[[4-amino-3,5-di(propan-2-yl)phenyl]methyl]-2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=C(N)C(C(C)C)=CC(CC=2C=C(C(N)=C(C(C)C)C=2)C(C)C)=C1 KZTROCYBPMKGAW-UHFFFAOYSA-N 0.000 description 1
- NHFKECPTBZZFBC-UHFFFAOYSA-N 4-amino-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1N NHFKECPTBZZFBC-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
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-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
- 241001076960 Argon Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 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
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- BFTPDHXRJZETQI-UHFFFAOYSA-N N=C=N.C(C)(C)C1=C(C(=CC=C1)C(C)C)C1=C(C=CC=C1C(C)C)C(C)C Chemical compound N=C=N.C(C)(C)C1=C(C(=CC=C1)C(C)C)C1=C(C=CC=C1C(C)C)C(C)C BFTPDHXRJZETQI-UHFFFAOYSA-N 0.000 description 1
- JHXVRRJXCDAINK-UHFFFAOYSA-N NC(=O)N.N#CC#N Chemical compound NC(=O)N.N#CC#N JHXVRRJXCDAINK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 1
- GWFGDXZQZYMSMJ-UHFFFAOYSA-N Octadecansaeure-heptadecylester Natural products CCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC GWFGDXZQZYMSMJ-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 240000000528 Ricinus communis Species 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
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-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
- NXOIWSPUTXWQSM-UHFFFAOYSA-N [Na].C1(=CC=CC=C1)P(O)=O Chemical compound [Na].C1(=CC=CC=C1)P(O)=O NXOIWSPUTXWQSM-UHFFFAOYSA-N 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
- IKWTVSLWAPBBKU-UHFFFAOYSA-N a1010_sial Chemical compound O=[As]O[As]=O IKWTVSLWAPBBKU-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 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 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000002947 alkylene 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
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
- 229910052612 amphibole Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000013876 argon Nutrition 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 229960002594 arsenic trioxide Drugs 0.000 description 1
- GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000001273 butane Substances 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
- JLATXDOZXBEBJX-UHFFFAOYSA-N cadmium(2+);selenium(2-);sulfide Chemical compound [S-2].[Se-2].[Cd+2].[Cd+2] JLATXDOZXBEBJX-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 229960001777 castor oil Drugs 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052620 chrysotile Inorganic materials 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
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 150000001941 cyclopentenes Chemical class 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 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
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 238000004821 distillation Methods 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
- 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
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- KKTHRZMKMWBNQQ-UHFFFAOYSA-N ethene;phosphoric acid Chemical compound C=C.OP(O)(O)=O KKTHRZMKMWBNQQ-UHFFFAOYSA-N 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- 229960005082 etohexadiol Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 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 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000002650 habitual effect Effects 0.000 description 1
- UKACHOXRXFQJFN-UHFFFAOYSA-N heptafluoropropane Chemical compound FC(F)C(F)(F)C(F)(F)F UKACHOXRXFQJFN-UHFFFAOYSA-N 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 229910052892 hornblende Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 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
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000000206 moulding compound Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- KMJFBHAJTOLWGZ-UHFFFAOYSA-N n,n-dimethyl-1-(4-methylpiperazin-1-yl)methanamine Chemical compound CN(C)CN1CCN(C)CC1 KMJFBHAJTOLWGZ-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
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-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
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- ADRDEXBBJTUCND-UHFFFAOYSA-N pyrrolizidine Chemical compound C1CCN2CCCC21 ADRDEXBBJTUCND-UHFFFAOYSA-N 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009705 shock consolidation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
- 150000003606 tin compounds Chemical class 0.000 description 1
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical class [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 239000012745 toughening agent Substances 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
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- CWBIFDGMOSWLRQ-UHFFFAOYSA-N trimagnesium;hydroxy(trioxido)silane;hydrate Chemical compound O.[Mg+2].[Mg+2].[Mg+2].O[Si]([O-])([O-])[O-].O[Si]([O-])([O-])[O-] CWBIFDGMOSWLRQ-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- 239000005436 troposphere Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/14—Powdering or granulating by precipitation from solutions
-
- 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
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
-
- 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
- C08G18/48—Polyethers
- C08G18/4891—Polyethers modified with higher fatty oils or their acids or by resin acids
-
- 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
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
-
- 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
-
- 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
- C08G18/7607—Compounds of C08G18/7614 and of C08G18/7657
-
- 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
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/0066—≥ 150kg/m3
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
-
- 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
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
本发明涉及致密并优选是多孔聚氨酯弹性体的生产,其方法是将a)和b)(如需要)与c)在存在或不存在d),e)和f)情况下进行反应:a)高分子量的多羟基化合物;b)低分子量的扩链剂和/或交联剂;c)苯-1,4-二异氰酸酯(p-PDI)和至少一种另外的选自甲苯二异氰酸酯、二苯甲烷二异氰酸酯、3,3’-二甲联苯二异氰酸酯、1,2-二苯乙烷二异氰酸酯的芳族二异氰酸酯和/或4-12个碳原子的脂族二异氰酸酯和/或6-18个碳原子的环脂二异氰酸酯;其中构成组分a)、c)和b)(如使用)优选用预聚物法进行反应,d)催化剂;e)发泡剂和f)添加剂。也叙述了适合于此目的的异氰酸酯预聚物。
Description
本发明涉及生产致密和优选是多孔的聚氨酯弹性体(文中也缩写为PU弹性体)的方法。
从一些专利和文献出版物可知,致密或多孔(例如微孔)PU弹性体的生产早已为人们所知。
它们的工业重要性决定于其好的机械性能与便宜的加工方法的结合。使用不同比率的不同化学构成组分可以生产加工性能和机械性能区别很大的可热塑加工或交联的致密或多孔PU弹性体。PU弹性体,其性能和应用的概述可见于例如Kunststoff-Handbuch(塑料手册),卷.7,聚氨酯,第1版,1966,R.Vieweg博士和A.Hochtlen博士编;第2版,1983,G.Oertel博士编;和第3版,1993,G.W.Becker教授和D.Braun教授编(Carl-Hanser-Verlag,Munich,Vienna)。
与能以类似方式使用的橡胶类型相比,微孔PU弹性体具有显著提高的阻尼性和优良的体积压缩性,因而它们用作摇摆振动和冲击阻尼体系的组分,特别是在汽车工业里。对于生产微孔PU弹性体,1,5-NDI和分子量为2000的聚(己二酸乙二醇酯)的反应产物(以异氰酸酯预聚物的形式与含活化剂的脂肪酸磺酸酯水溶液反应)被证明是有用的(Kunststoff-Handbuch,Vol.7,Polyurethane,1st Ed.,pp.270ff.):
由于这种基础配方得到阻尼特性和静、动态性能参数均很好的微孔PU弹性体,现有技术只公开了旨在以较易处理和较便宜的二异氰酸酯取代给予良好弹性体性能的1,5-NDI的很少的努力(尽管由于其高熔点而难于处理),因为这导致机械性能明显的变差。基于1,5-NDI和基于4,4’-MDI的一般的致密PU弹性体和特别是微孔PU弹性体情况下之间的特性差别示于Journal of Elastomers and Plastics〔弹性体和塑料杂志〕,Vol.21,(1989),pp100-121。基于4,4’-MDI的微孔PU弹性体的重要缺点是,随着材料加热增强和动态负荷下的固结值(Setzbetrag)明显增加,阻尼程度明显较高,与基于1,5-NDI的PU弹性体相比最终导致材料的迅速磨损。
尽管有这些已知的缺点,仍然做了以熔点较低和较便宜的4,4’-MDI取代1,5-NDI以生产微孔PU弹性体的尝试。但这些尝试都局限在使用新的原料组分,特别是高分子量的多羟基化合物,用这种化合物,微孔PU弹性体的某些机械性能得到了改进。
EP-A-0 496 204(US-A 5 173 518)公开了一种生产多孔PU弹性体的方法,是用含平均分子量150-500的缩合形式的聚氧四亚甲基二醇基团的聚醚型聚碳酸酯二醇作为高分子量的多羟基化合物进行的。这样就改进了机械性能,特别是其断裂伸长,甚至是在相对低的温度下。但在按DIN 53572法于70℃下进行的静态残余压缩变形中未发现有明显改进,已知这是与动态固结值有联系的。甚至在使用1,5-NDI作为多异氰酸酯时,仅得到平均静态残余压缩变形。
EP-B-0 243 832(US-A-4 798 851)叙述了作为发泡剂的水存在或不存在的情况下使用基于4,4’-MDI的假预聚物生产有弹性的致密或多孔PU或PU-聚脲模制体,该文献用短链聚氧四亚甲基二醇和脂族二元羧酸含羟基的缩聚物作为高分子量的多羟基化合物,其发明目的是得到能迅速用泵计量的含酯基的多羟基化合物以生产机械和水解性能得到改进的多孔或致密PU弹性体。有关通常作为防震材料特征的静态或动态负荷下永久形变程度的详细资料未见公开。
DE-A-36 13 961(US-A-4 647 596)叙述了基于4,4’-MDI的微孔PU弹性体,由于高分子量的多羟基化合物的限定组成(包括聚四氢呋喃和ε-己内酯的共聚物),它具有静态强度与动态应力很好协调的机械性能。尽管生产多羟基化合物使用较贵的原料,但所得性能在测试值“产品耐久性、抗弯强度(De Mattia法)和永久形变(50%压缩)”方面的增加似乎相对较小。例如,使用该发明的教导时,所测得的残余压缩变形值(直接与在实用上重要的动态固结参数有关)仅显示有微小的改进。
此外,所用的测试标准“产品耐久性和De Mattia法抗弯强度”似乎不完全适合动态性能的评价,因为在部分性能改进的情况下它们不能满意地显示基于4,4’-MDI和1,5-NDI的聚氨酯弹性体之间的实际性能差别。因此,基于1,5-NDI的实例比基于4,4’-MDI的实例没有展示出较高的性能水平。
PU弹性体的分步生产也是已知的。按照DE-A-25 47 864(US-A-4 191 818)用主要是线型的高分子量的二羟基化合物与不足量的二异氰酸酯反应,得到含端羟基的加合物,接着将此加合物与过量的对称芳族二异氰酸酯反应并以烷二醇或二(亚烷基二醇)的对苯二甲酸酯作为扩链剂能够生产耐热的PU弹性体。如欲用此法生产多孔PU弹性体,也可加入水,必要时与烷二醇和/或二(亚烷基二醇)的对苯二甲酸酯结合使用以作为扩链剂。
多孔PU弹性体也可用DE-A-2 940 856(US-A-4 334033)所述方法进行生产。按照此方法,高分子量的多羟基化合物和(如果必要)扩链剂按OH基/NCO基之比为1.2∶1-2∶1的比例与一有机二异氰酸酯反应得到含羟基的预聚物。将其分为重量比约为80-20∶20-80的组分(I)和组分(II)。组分(I)按1∶2.5-12的OH/NCO比与1,5-NDI进行反应,得到含NCO基的NDI-聚氨酯加合物;组分(II)与扩链剂、水和添加剂混合,得到混合物(II)。最后将NDI-聚氨酯加合物与混合物(II)反应,得到致密或多孔PU弹性体。此方法能使构成组分准确计量并快而充分的混合。PU弹性体是均匀的,并且整个模制件有均匀的机械性能。
本发明的目的是提供一生产致密或优选是微孔PU弹性体的方法,其中昂贵的1,5-NDI至少可以部分地被较易处理和价格较低的有机二异氰酸酯或二异氰酸酯混合物所代替。尽管有其它有机二异氰酸酯伴随使用,所生产的PU弹性体的机械性能也有所改进或至少与基于1,5-NDI的弹性体基本相当。不论采用何种类型的高分子量的多羟基化合物,微孔PU弹性体明显地具有改进的静态和机械性能,特别是残余压缩变形和动态固结值(与基于4,4’-MDI的弹性体比较),因此它们能够用来特别是生产摇摆振动和冲击阻尼体系。
现已发现,此目的的完成是用一种生产致密或多孔、优选是微孔PU弹性体的方法,该方法是在d)、e)和f)存在或不存在下将a)和b)(如需要)与c)进行反应:
a)高分子量的多羟基化合物;
b)低分子量扩链剂和/或交联剂;
c)有机多异氰酸酯;
d)催化剂;
e)发泡剂;
f)添加剂,其中所用的有机多异氰酸酯是苯-1,4-二异氰酸酯(p-PDI)和至少一种另外的选自甲苯二异氰酸酯、二苯甲烷二异氰酸酯、3,3’-二甲基联苯二异氰酸酯、1,2-二苯乙烷二异氰酸酯的芳族二异氰酸酯,和/或4-12个碳原子的脂族二异氰酸酯和/或6-18个碳原子的环脂族二异氰酸酯。
按照优选使用的生产方式按预聚物法制备PU弹性体,其中有利的是由高分子量的多羟基化合物a)和至少一种选自甲苯二异氰酸酯(TDI)、MDI、3,3’-二甲联苯二异氰酸酯(TODI)、1,2-二苯基乙烷二异氰酸酯(DIBDI)中的芳族二异氰酸酯、优选是4,4’-MDI和/或六亚甲基-1,6-二异氰酸酯(HDI)和/或1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷(IPDI)制备含氨基甲酸酯和异氰酸酯基的加聚产物,然后将此加聚产物与p-PDI反应(一步反应或分成几份进行反应)以转化成含异氰酸酯基的预聚物。从这种含异氰酸酯基的预聚物,将其与水或水和(如需要)低分子量扩链剂和/或交联剂b)和/或高分子量的多羟基化合物a)的混合物反应,即能生产微孔PU弹性体。
本发明也提供含异氰酸酯基且-NCO含量为3.3-10wt%、优选3.5-9.0wt%的预聚物,其制备是将至少一种高分子量的多羟基化合物a)或a)和至少一种低分子量扩链剂和/或交联剂b)的混合物与至少一种芳族二异氰酸酯和/或HDI和/或IPDI反应以得到含氨基甲酸酯和异氰酸酯基且-NCO含量优选为0.05-8wt%、更优选1.2-7.5wt%的加聚产物。其中芳族二异氰酸酯选自TDI、MDI、TODI、DIBDI,优选4,4’-MDI。然后将此加聚产物与p-PDI反应,p-PDI可被引入反应混合物中与加聚产物进行一步反应或者优选是将其分成数份与加聚产物进行反应。
微孔PU弹性体具有优良的静态和动态性能。由于它们的比阻尼特性和能长期使用的性能,它们特别用于振动和冲击阻尼体系。
由于基于p-PDI的PU弹性体中含有脲和/或氨基甲酸酯基的刚性链段的结晶能力在很大程度上被伴随使用的结晶不好的二异氰酸酯所破坏(例如价廉的其结构成角度的4,4’-MDI),本技术领域的技术熟练者会设想到所得到的PU弹性体比基于芳族二异氰酸酯的弹性体的静态和动态性能更差。
因此,由含p-PDI的芳族、脂族和/或环脂族二异氰酸酯的混合物生产的微孔PU弹性体具有几乎能与仅由p-PDI生产的弹性体相比的好机械性能并且其静态机械性能,特别是残余压缩变形和动态固结值与基于4,4’-MDI的微孔PU弹性体相比有明显提高是不可预见的。因此由本发明方法生产的微孔PU弹性体比基于1,5-NDI的PU弹性体便宜,并且由于其静态机械性能好,它们在生产摇摆振动和冲击阻尼体系中是非常有用的。另外,反应混合物的处理和加工较简单。
下面叙述有关生产致密或优选是多孔(例如微孔)PU弹性体的原料a)-f)和本发明的方法:
a)适合的高分子量多羟基化合物优选具有官能度3或优选2和分子量500-6000、优选800-3500、特别是1000-3300,并优选包括含羟基的聚合物,例如诸如聚甲醛以及特别是水不溶性缩甲醛(例如聚丁二醇缩甲醛和聚己二醇缩甲醛)之类的聚缩醛;诸如聚氧亚丁基二醇、聚氧亚丁基-聚氧亚乙基二醇、聚氧亚丁基-聚氧亚丙基二醇、聚氧亚丁基-聚氧亚丙基-聚氧亚乙基二醇、聚氧亚丙基多元醇和聚氧亚丙基-聚氧亚乙基多元醇之类的聚氧亚烷基多元醇;以及聚酯型多元醇,例如由有机二羧酸和/或二羧酸衍生物和二元至三元醇和/或二亚烷基二醇制备的、由羟基羧酸和内酯制备的聚酯多元醇以及含羟基的聚碳酸酯。
己被发现是非常有用并因此是优选使用的高分子量的多羟基化合物是分子量>800-3500、优选1000-3300的二官能多羟基化合物,并选自聚酯多元醇、含羟基的聚碳酸酯和聚氧亚丁基二醇。高分子量的多羟基化合物可以单独使用或作为混合物使用。
适合的聚氧亚烷基多元醇可用已知方法来制备,例如从亚烷基中有2-4个碳原子的一种或多种环氧烷烃以碱金属氢氧化物(诸如氢氧化钠或钾)或碱金属的醇盐(诸如甲醇钠、乙醇钠或钾或异丙醇钾)为催化剂并加入含2或3个、优选是2个结合形式的活性氢原子的至少一种引发剂分子用阴离子聚合法制备;或用路易斯酸(诸如五氯化锑、三氟化硼醚合物等)或漂白土作为催化剂用阳离子聚合法制备。
适合的环氧烷烃是,例如,1,3-环氧丙烷、1,2-或2,3-环氧丁烷,优选环氧乙烷和1,2-环氧丙烷,特别优选四氢呋喃。环氧烷烃可以单独使用、连续交替使用或作为混合物使用。适合的引发剂分子的例子是,水,有机二元羧酸(诸如琥珀酸、己二酸、邻苯二甲酸和对苯二甲酸),烷基上有1-4个碳原子的脂族和芳族N-单烷基化和N,N’-二烷基化二胺(例如单烷基化或二烷基化乙二胺、1,3-丙二胺、1,3-或1,4-丁二胺、1,2-、1,3-、1,4-、1,5-和1,6-六亚甲基二胺),烷醇胺(诸如乙醇胺、N-甲基乙醇胺和N-乙基乙醇胺),二烷醇胺(诸如二乙醇胺、N-甲基二乙醇胺和N-乙基二乙醇胺),以及三烷醇胺(诸如三乙醇胺)和氨。优选使用的是二元和/或三元醇,例如2-12个碳原子优选2-4个碳原子的烷二醇(例如乙二醇、1,2-和1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、丙三醇和三羟甲基丙烷)以及一缩二烷二醇(诸如二甘醇和一缩二丙二醇)。
至于聚氧亚烷基二醇,优选使用的是分子量500-3000、优选650-2300的聚氧亚丁基二醇(聚氧四亚甲基二醇)。
多羟基化合物a)优选使用聚酯型多元醇,例如可以从2-12个、优选4-6个碳原子的烷烃二羧酸和/或芳族二羧酸和多元醇(优选2-12个碳原子的烷二醇,并优选2-6个碳原子)和/或一缩二烷二醇制备。适合的烷烃二羧酸的实例是琥珀酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸和癸烷二羧酸。适合的芳族二羧酸是,例如邻苯二甲酸、间苯二甲酸和对苯二甲酸。烷烃二羧酸可以单独使用或相互混合使用。也可以用相应的二羧酸衍生物(诸如1-4个碳原子的醇的二羧酸单酯或二酯或二羧酸酐)代替游离的二羧酸。优选使用的是琥珀酸、戊二酸和己二酸以例如20-35∶35-50∶20-32重量比的二羧酸混合物,特别是己二酸。二元醇和多元醇、特别是烷烃二醇和一缩二烷二醇的实例是乙二醇、二甘醇、1,2-或1,3-丙二醇、一缩二丙二醇、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、二甘醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇或至少所述两种二醇的混合物,特别是1,4-丁二醇、1,5-戊二醇和1,6-己二醇的混合物。也可以使用衍生自内酯(例如ε-己内酯)或羟基羧酸(例如ω-羟基己酸)的聚酯型多元醇。
聚酯型多元醇的制备是在无催化剂存在下或优选是在酯化催化剂存在下、有利的是在诸如氮、氦、氩等惰性气体的气氛中,于150-250℃(优选180-220℃)下的熔融态、任选的在减压下将芳族和/或脂族二羧酸并优选是烷二酸和/或衍生物与多元醇缩聚至所要求的酸值,该酸值低于10是有利的,优选低于2。根据一最佳具体实施方案,酯化混合物在上述温度于大气压下并相继在低于500mbar(优选50-150mbar)的压力下缩聚至酸值为80-30,优选40-30。适合的酯化催化剂例如是铁、镉、钴、铅、锌、锑、镁、钛和锡催化剂,以其金属、金属氧化物或金属盐的形式。但缩聚也可在液相中在稀释剂和/或共沸剂(诸如苯、甲苯、二甲苯或氯代苯)存在下进行,以共沸蒸馏出缩合水。
制备聚酯型多元醇时,有机多元羧酸和/或衍生物与多元醇有利地以1∶1-1.8、优选1∶1.05-1.2的摩尔比进行缩聚。
优选使用的聚酯型多元醇是诸如聚乙二醇己二酸酯、聚(1,4-丁二醇己二酸酯)、聚(乙二醇-1,4-丁二醇己二酸酯)、聚(1,6-己二醇-新戊二醇己二酸酯)和聚(1,6-己二醇-1,4-丁二醇己二酸酯)之类的聚烷二醇己二酸酯和聚己内酯。
可提及的其它适合的聚酯型多元醇有含羟基的聚碳酸酯。其制备例如可用上述的烷二醇(特别是1,4-丁二醇和/或1,6-己二醇)和/或一缩二烷二醇(诸如二甘醇、一缩二丙二醇和一缩二丁二醇)与碳酸二烷酯或二芳酯(例如碳酸二苯酯)或光气进行反应。
优选使用的含羟基的聚碳酸酯是聚醚型聚碳酸酯二醇,其制备可用a1)或a2)与光气、碳酸二苯酯或有C1-4烷基的碳酸二烷酯进行缩聚反应:
a1)分子量为150-500的聚氧亚丁基二醇,
a2)包括i)和ii)的混合物:
i)至少10mol%、优选50-95mol%的分子量为150-500的聚氧亚丁基二醇(a1),
ii)低于90mol%、优选5-50mol%的至少一种异于(a1)并且分子量为150-2000的聚氧亚烷基二醇、至少一种一缩二烷二醇、至少一种线形或支化的2-12个碳原子的烷二醇以及至少一种5-15个碳原子的环状烷二醇或它们的混合物。
b)用本发明方法生产致密或优选是多孔PU弹性体时,除高分子量多羟基化合物a)外,还可使用低分子量二官能扩链剂b),低分子量优选三官能或四官能交联剂b)或扩链剂和交联剂的混合物。
这种扩链剂和交联剂b)是用以改良PU弹性体的机械性能,特别是硬度的。适合的扩链剂(诸如烷二醇、一缩二烷二醇和聚氧亚烷基二醇)和交联剂(例如三元或四元醇和官能度为3-4的低聚聚氧亚烷基多元醇)的分子量通常低于800,优选18-400,特别是60-300。优选使用的扩链剂是2-12个碳原子、优选2、4或6个碳原子的烷二醇(例如乙二醇、1,3-丙二醇、1,5-戊二醇、1,6-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇、1,10-癸二醇,特别是1,4-丁二醇)和4-8个碳原子的一缩二烷二醇(例如二甘醇和一缩二丙二醇)以及聚氧亚烷基二醇。然而,适合的扩链剂还包括通常不多于12个碳原子的有支链的和/或不饱和的烷二醇(例如1,2-丙二醇、2-甲基丙烷-1,3-二醇、2,2-二甲基丙烷-1,3-二醇、2-丁基-2-乙基丙烷-1,3-二醇、丁-2-烯-1,4-二醇和丁-2-炔-1,4-二醇),有2-4个碳原子的二醇与对苯二甲酸的二酯(例如对苯二甲酸二(乙二醇)酯或对苯二甲酸二(1,4-丁二醇)酯),氢醌或间苯二酚的羟亚烷基醚(例如1,4-二(β-羟乙基)氢醌或1,3-二(β-羟乙基)间苯二酚),2-12个碳原子的烷醇胺(例如乙醇胺、2-氨基丙醇和3-氨基-2,2-二甲基丙醇),诸如N-甲基二乙醇胺和N-乙基二乙醇胺之类的N-烷基二烷醇胺,2-15个碳原子的(环)脂二胺(例如乙二胺、1,2-或1,3-丙二胺、1,4-丁二胺和1,6-己二胺、异佛尔酮二胺、1,4-环己二胺和4,4’-二氨基二环己基甲烷),N-烷基烷二胺和N,N’-二烷基烷二胺(诸如N-甲基丙邻二胺和N,N’-二甲基乙二胺)和芳族二胺(诸如亚甲基二(4-氨基-3-苯甲酸甲酯)、1,2-双(2-氨基苯硫基)乙烷、二(对氨基苯甲酸)丙二醇酯、2,4-和2,6-甲苯二胺、3,5-二乙基-2,4-和2,6-甲苯二胺、4,4’-二氨基二苯甲烷、3,3’-二氯-4,4’-二氨基二苯甲烷和主要为邻位二烷基、三烷基和/或四烷基取代的4,4’-二氨基二苯甲烷,诸如3,3’-二异丙基-和3,3’,5,5’-四异丙基-4,4’-二氨基二苯甲烷。
有利于生产PU铸塑弹性体的至少三官能的交联剂的实例是:三官能和四官能醇(诸如丙三醇、三羟甲基丙烷、季戊四醇和三羟基环己烷)和四羟烷基烷二胺(诸如四(2-羟乙基)乙二胺或四(2-羟丙基)乙二胺)以及3-4官能度的低聚聚氧亚烷基多元醇。
适合于本发明的扩链剂和交联剂b)可以单独使用或以混合物的形式使用。使用扩链剂和交联剂混合物也是可以的。
构成组分a)和b)的混合比可在相对宽的范围内改变以调整PU弹性体的硬度,随着PU弹性体中的二官能扩链剂和至少是三官能交联剂的含量的增加其硬度有所增加。
根据所要求的硬度,构成组分a)和b)的需要量可用简单方法由实验来决定,对于生产硬质PU弹性体来说,有利的扩链剂和/或交联剂b)的用量是基于高分子量的多羟基化合物a)的5-50wt%,优选使用30-50wt%。
c)按照本发明,致密并优选是微孔PU弹性体是用两种有机多异氰酸酯生产的,其中的一种是p-PDI。可使用的不同于p-PDI的芳族二异氰酸酯是甲苯二异氰酸酯(例如2,4-和2,6-TDI和商品混合物)、二苯甲烷二异氰酸酯(例如2,4’-、2,2’-并优选4,4’-MDI和至少两种所说MDI异构体的混合物)、3,3’-二甲基联苯二异氰酸酯(例如3,3’-二甲基-4,4’-二异氰酸根合联苯(TODI))、1,2-二苯乙烷二异氰酸酯(例如2,4’-,2,2’-并优选4,4’-DIBDI和至少两种所说DIBDI异构体的混合物)。由于好的加工性和弹性体可以达到的很好的机械性能,特别优选使用4,4’-MDI与p-PDI组合以生产致密的并优选是微孔PU弹性体。ρ-PDI与选自TDI、MDI、TODI和DIBDI的芳族二异氰酸酯的摩尔比可在大范围内改变而不明显改变静态和动态性能,例如ρ-PDI与芳族二异氰酸酯的摩尔比为1∶0.1-1∶10,优选1∶0.11-1∶9,特别优选1∶1-1∶4。当用p-PDI和4,4’- MDI这一优选组合时,有利的ρ-PDI与4,4’-MDI的摩尔比范围在1∶0.1-1∶10,优选1∶0.11-1∶9,特别优选1∶1-1∶4。如果需要,芳族二异氰酸酯可以单独熔融然后混合或混合后熔融在一起,并作为熔融体以生产PU弹性体;或者可将固体二异氰酸酯加入其它二异氰酸酯熔融体中并将其熔化并溶于其中。按照最后一个变体方法,固体p-PDI(熔点94℃)通常是被加入4,4’-MDI熔融体中并在熔融时溶解。
也可以用在支化链或优选是线形亚烷基中有4-12个碳原子(优选是4-6个碳原子)的脂族二异氰酸酯和/或在未取代或烷基取代的环亚烷基中有6-18个(优选6-10个)碳原子的环脂二异氰酸酯代替芳族二异氰酸酯或与其相混合以生产致密并优选是多孔PU弹性体。可述及的脂族二异氰酸酯的实例是十二烷-1,12-二异氰酸酯、2-乙基丁烷-1,4-二异氰酸酯、2-甲基戊烷-1,5-二异氰酸酯、丁烷-1,4-二异氰酸酯以及优选的六亚甲基-1,6-二异氰酸酯(HDI)。适合的环脂二异氰酸酯实例是环己烷-1,3-和1,4-二异氰酸酯、六氢甲苯-2,4-和2,6-二异氰酸酯、二环己基甲烷-4,4’-、2,4’-和2,2’-二异氰酸酯以及优选的1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷(异佛尔酮二异氰酸酯,IPDI)。
但优选的实施方案中有机多异氰酸酯(c)是以含异氰酸酯基的预聚物形式使用的。其制备是,例如将含p-PDI的二异氰酸酯熔融体与至少一种高分子量的多羟基化合物a)或a)与至少一种低分子量扩链剂和/或至少一种交联剂b)的混合物进行反应,或是用含p-PDI的二异氰酸酯熔融体与至少一种高分子量的多羟基化合物a)反应然后接着再与至少一种扩链剂和/或交联剂反应的分步反应。
但是优选使用的是含异氰酸酯基的预聚物而且其制备是将部分或全部量的至少一种高分子量的多羟基化合物a)或a)与至少一种低分子量扩链剂和/或交联剂b)的部分或全部量的混合物与至少一种选自TDI、MDI、TODI和DIBDI的芳族二异氰酸酯(优选与4,4’-MDI)和/或HDI和/或IPDI进行反应,以得到含氨基甲酸酯基(优选氨基甲酸酯和异氰酸酯基)并且-NCO含量为0.05-8.0wt%(优选1.2-7.5wt%)的加聚产物,然后将此加聚产物与ρ-PDI反应以得到含异氰酸酯基的预聚物。
制备含氨基甲酸酯和异氰酸酯基的加聚产物时,有利的构成组分a)、b)(如需要)和c)的用量是:a)或a)+b)的羟基与芳族二异氰酸酯TDI、MDI、TODI、DIBDI(优选4,4’-MDI)和/或HDI和/或IPDI的异氰酸酯基的当量比为1∶(大于1-6),优选1∶1.01-4。含氨基甲酸酯和异氰酸酯基的加聚产物然后与p-PDI反应转变为含异氰酸酯基的预聚物,反应中ρ-PDI能在一步法或优选是分份地在多步(优选2步)法中反应的用量应使a)或a)+b)的羟基与p-PDI的异氰酸酯基的当量比为1∶0.02-6,优选1∶0.1-5,特别优选1∶0.2-3。
如已述及,a)和b)的混合物能用来制备含异氰酸酯基的预聚物。但按照本发明的一个最佳具体实施方案,含异氰酸酯基的预聚物是只用高分子量的多羟基化合物a)与多异氰酸酯c)(优选与4,4’-MDI和ρ-PDI)反应制备的。用于此目的的特别适合的多羟基化合物是分子量为500-6000、优选>800-3500、特别优选1000-3300的二官能多羟基化合物,并选自聚酯型多元醇、含羟基的聚碳酸酯和聚氧四亚甲基二醇。
当用4,4’-MDI和ρ-PDI作为芳族二异氰酸酯时,发现采用a)+b)的羟基(优选是只用a))∶4,4’-MDI的-NCO基∶p-PDI的-NCO基为1∶(大于1-6)∶0.02-6的当量比时是有用的。
能用于本发明并优选是用上述变体方法制备的含异氰酸酯基的预聚物的优选的异氰酸酯含量为3.3-10wt%、优选3.5-9wt%,基于它们的总重量计算。
制备含异氰酸酯基的预聚物时,高分子量多羟基化合物a)或a)和低分子量扩链剂和/或交联剂b)的混合物与有机多异氰酸酯c)的反应可在例如80-160℃、优选90-150℃的温度下以含p-PDI的芳族二异氰酸酯混合物的形式或优选是用分步法进行,首先使用选自TDI、MDI、TODI、DIBDI(优选4,4’-MDI)的至少一种芳族二异氰酸酯,随后再加入p-PDI。
因此,例如可将全量或部分量(如需要)的ρ-PDI溶于加热至例如110℃的芳族二异氰酸酯(优选4,4’-MDI),然后将加热至例如125℃的多羟基化合物a)和扩链剂和/或交联剂b)(如需要)加入二异氰酸酯混合物。在混合物经过最高反应温度(通常在130-150℃范围)以后在冷却阶段(例如90-130℃)加入任何剩余量的ρ-PDI并反应。
根据优选采用的另一变体方法,可将组分a)或a)+b)的混合物加热至例如140℃,并在此温度下加入芳族二异氰酸酯,优选加热至50℃的全部量的4,4’-MDI。在加入4,4’-MDI后,立刻加入所有的ρ-PDI或分批加入部分ρ-PDI。业已发现,在加入4,4’-MDI后立即加入部分量的ρ-PDI并将其它各部分量在冷却阶段加入反应混合物是有利的。
异氰酸酯含量达到理论计算值后,终止反应。反应时间通常要求10-200分钟,优选15-150分钟。
含异氰酸酯基的预聚物可在催化剂存在下制备,但也可在无催化剂存在下制备,并将它们掺入反应混合物以生产PU弹性体。
d)关于催化剂d),有利的是使用能大大加速组分a)的含羟基化合物和b)(如需要)与多异氰酸酯c)反应的化合物。适合的催化剂是有机金属化合物,优选有机锡化合物,诸如有机羧酸的锡(II)盐(例如乙酸锡(II)、辛酸锡(II)、乙基己酸锡(II)和月桂酸锡(II))和有机羧酸二烷基锡(IV)盐(例如二乙酸二丁锡、二月桂酸二丁锡、马来酸二丁锡和二乙酸二辛锡)。有机金属化合物是单独使用的或优选是与强碱性胺结合使用。可以述及的实例是脒类,诸如2,3-二甲基-3,4,5,6-四氢嘧啶;叔胺诸如三乙胺、三丁胺、二甲基苄基胺、N-甲基吗啉、N-乙基吗啉、N-环己基吗啉;N,N,N’,N’-四烷基烷二胺诸如N,N,N’,N’-四甲基乙二胺、N,N,N’,N’-四甲基丁二胺或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(二甲氨丙基)脲;1,4-二甲基哌嗪、1,2-二甲基咪唑;1-氮杂双环〔3.3.0〕辛烷和优选的1,4-二氮杂双环〔2.2.2〕辛烷和烷醇胺化合物(诸如三乙醇胺、三异丙醇胺、N-甲基二乙醇胺和N-乙基二乙醇胺和二甲基乙醇胺),优选使用的催化剂或催化剂组合的量为0.001-3wt%、特别是0.01-1.0wt%,基于构成组分a)、c)和(如使用)b)的重量计算。
e)诸如PU铸塑弹性体之类的致密PU弹性体可用本发明方法在无湿气和物理或化学作用的发泡剂存在下进行生产,但此方法优选用于生产多孔、特别是微孔PU弹性体。用于此目的的发泡剂(e)是水,它能就地与有机多异氰酸酯并优选是含异氰酸酯基的预聚物a)反应形成二氧化碳和氨基,它们再进一步与异氰酸酯预聚物反应而产生脲基,因而起着扩链剂作用。
由于构成组分a)和b)(如使用)因其制备和/或化学组成可含水,在许多情况中是不需要在构成组分a)和b)(如使用)里或反应混合物里另外加入水。但如果必须在聚氨酯配方中另外加水以达到所要求的松密度的话,通常采用的量是0.001-3.0wt%,优选0.01-2.0wt%,特别是0.2-1.2wt%,基于构成组分a)-c)的重量计算。
也可使用低沸点液体化合物(它们在加聚反应放热作用下蒸发且在大气压下的沸点有利的是-40-120℃范围、优选10-90℃范围)或使用气体作为物理作用或化学作用的发泡剂代替水或优选与水结合作为发泡剂e)。
适合于作为发泡剂的上述类型的液体和气体可选自例如下列的化合物:烷烃(诸如丙烷、正-和异-丁烷、正-和异-戊烷并优选工业戊烷混合物),环烷烃和环烯烃(诸如环丁烷、环戊烯、环己烯并优选环戊烷和/或环己烷),二烷基醚(诸如甲醚、甲***或***、叔丁甲醚),环烷基醚(诸如呋喃),酮(诸如丙酮、甲乙酮),缩醛和/或缩酮(诸如甲醛缩二甲醇、1,3-二氧戊环和丙酮缩二甲醇),羧酸酯(诸如乙酸乙酯、甲酸甲酯和乙烯-丙烯酸叔丁酯),叔醇(诸如叔丁醇),在对流层中能降解因而不损害臭氧层的氟代烷烃(例如三氟甲烷、二氟甲烷、二氟乙烷、四氟乙烷和七氟丙烷)、氯代烷烃(诸如2-氯代丙烷)和诸如氮、一氧化碳之类的气体和诸如氦、氖和氪之类的稀有气体以及化学作用类似水的发泡剂(例如,诸如甲酸、乙酸和丙酸之类的羧酸)。
在对-NCO基呈惰性的并适于作为发泡剂e)的液体中,优选使用的是4-8碳原子的烷烃、4-6碳原子的环烷烃或由烷烃和环烷烃组成的大气压沸点为-40~50℃的混合物。特别优选使用的是C5-(环)烷烃,诸如正戊烷、异戊烷和环戊烷以及它们的工业混合物。
其它适合的发泡剂是能热分解的盐类,例如碳酸氢铵、氨基甲酸铵和/或有机羧酸的铵盐(例如丙二酸、硼酸、甲酸或乙酸的单铵盐)。
固体发泡剂、低沸点液体发泡剂和气体发泡剂单独使用或以混合物形式(例如作为液体混合物、气体混合物或气/液混合物)使用时的最适合的用量决定于要达到的密度和水的用量。该要求量能够容易地用简单的试验来决定。基于构成组分a)、c)和b)(如使用)的重量计算,0.5-35重量份、优选2-15重量份的固体量;1-30重量份、优选3-18重量份的液体量;和/或0.01-80重量份、优选10-35重量份的气体量通常得到了满意的结果。载负气体例如空气、二氧化碳、氮和/或氦可以通过高分子量的扩链剂和/或交联剂b)或通过多异氰酸酯c)或通过a)和c)和b)(如使用)来实施。
不被使用的发泡剂是全卤代的氯氟烃,如己指出。
f)如果需要,可将添加剂f)掺入反应混合物以生产致密并优选是多孔PU弹性体。可述及的实例是表面活性物质、泡沫稳定剂、孔穴调节剂、填料、阻燃剂、成核剂、氧化抑制剂、稳定剂、润滑剂和脱模剂、染料和颜料。
可能的表面活性物质是,例如有助于原料匀化的化合物,也可以是适合于调节孔穴结构的化合物。可述及的实例是诸如蓖麻油硫酸或脂肪酸钠盐之类的乳化剂,也可以是脂肪酸胺盐(例如油酸二乙胺、硬脂酸二乙醇胺、蓖麻油酸二乙醇胺)、磺酸盐(例如十二烷基苯-或二萘基甲烷二磺酸和蓖麻油酸的碱金属盐或铵盐);泡沫稳定剂,诸如硅氧烷-氧化亚烷基共聚物和其它有机聚硅氧烷、乙氧基化烷基酚、乙氧基化脂肪醇、石蜡油、蓖麻油酯或蓖麻油酸酯、土耳其红油和花生油;以及孔穴调节剂,诸如石蜡烃、脂肪醇和二甲基聚硅氧烷。有聚氧亚烷基和氟代烷烃基侧基的低聚聚丙烯酸酯也是适合于改进乳化作用、孔穴结构和/或其稳定性的。表面活性物质的通常用量为0.01-5重量份,基于100重量份高分子量的多羟基化合物a)计算。
在本发明的目的中,填料、特别是增强填料是惯用的本身是已知的有机和无机填料、增强剂和增重剂。具体实例是:诸如硅质矿物之类的无机填料,例如片状硅酸盐(诸如叶蛇纹石、蛇纹石、角闪石、闪石、纤蛇纹石、滑石);金属氧化物(诸如高岭土、氧化铝、硅酸铝、氧化钛和氧化铁);金属盐(诸如白垩、重晶石)和无机颜料(诸如硫化镉、硫化锌)以及玻璃粒子。适合的有机填料是:例如炭黑、三聚氰胺、膨胀石墨、松香、环戊二烯基树脂和接枝聚合物。
优选使用的增强填料是纤维,例如碳纤维或特别是玻璃纤维,特别是在要求高抗热变形或很高的刚韧性时。纤维可用偶联剂和/或上胶剂涂敷。适合的玻璃纤维增强填料也使用玻璃纺织物、玻璃垫、玻璃非纺织物和/或优选是玻璃纤维纱或直径5-200μm、优选6-15μm的低碱E玻璃的切断纤维,在掺入模塑组合物后一般具有的平均纤维长度为0.05-1 mm,优选0.1-0.5mm。
无机和有机填料可以单独使用或作为混合物使用,通常掺入反应混合物中的量为0.5-50wt%,优选1-30wt%,基于构成组分a)-c)的重量计算。
适合的阻燃剂是,例如磷酸三甲苯酯、磷酸三(2-氯乙酯)、磷酸三(2-氯丙酯)、磷酸三(1,3-二氯丙酯)、磷酸三(2,3-二溴丙酯)和亚乙基二磷酸四(2-氯乙酯)。
除上述卤代磷酸酯外,也可以使用无机阻燃剂,诸如红磷、水合氧化铝、三氧化锑、三氧化二砷、多磷酸铵和硫酸钙或氰脲酸衍生物,诸如三聚氰胺或至少两种阻燃剂的混合物,例如多磷酸铵和三聚氰胺混合物以及(如需要)用淀粉和/或膨胀石墨以使按本发明的PU弹性体阻燃。一般说来,每100重量份构成组分a)-c)使用5-50重量份、优选5-25重量份的所述阻燃剂或混合物被发现是有利的。
可以使用的成核剂是,例如滑石、氟化钙、苯次膦酸钠、氧化铝和分得很细的聚四氟乙烯,其量达5wt%,基于构成组分a)-c)总重计算。
可以加入本发明PU弹性体的适合氧化抑制剂和热稳定剂是,例如周期表第I族金属的卤化物,例如卤化钠、钾、锂(需要时与卤化铜(I)结合使用,例如氯化铜、溴化铜或碘化铜);位阻酚;氢醌以及这些组的取代化合物和它们的混合物,它们的使用浓度优选达1wt%,基于构成组分a)-c)的重量计算。
UV稳定剂的实例是各种取代的间苯二酚、水杨酸酯、苯并***和二苯酮以及位阻胺,它们的用量一般达2.0wt%,基于构成组分a)-c)的重量计算。
一般同样以基于构成组分a)-c)的重量计算以达1wt%的量加入的润滑剂和脱模剂是硬脂酸、十八烷醇、硬脂酸酯和硬脂酰胺,以及季戊四醇的脂肪酸酯。
还可以加入有机染料,诸如苯胺黑或颜料,诸如二氧化钛、硫化镉、硫化镉·硒化镉、酞菁、群青或炭黑。
上述其它惯用助剂和添加剂的详细情况可见于专业文献中,例如J.H.Saunders和K.C.Frisch专著,“High Polymers〔高聚物〕”,Vol.XVI,Polyurethane〔聚氨酯〕,Part 1和2,Interscience Publishers1962 or 1964;或Kunststoff-Handbuch,Polyurethane〔塑料手册,聚氨酯〕,Vol.VII,Carl-Hanser-Verlag,Munich,Vienna,1st,2nd or 3rdEd.,1966,1983和1993。
生产致密或优选是多孔PU弹性体时,高分子量多羟基化合物a)、(如需要)低分子量扩链剂和/或交联剂b)和(如需要)化学作用的发泡剂(优选水)和有机多异氰酸酯c)或者优选是含异氰酸酯基并由a)、b)和c)或优选是由a)和c)制备的预聚物和扩链剂和/或交联剂b),部分量a)和b)的混合物,部分量a)、b)和水的混合物或优选是b)和水的混合物或水可在催化剂d)、物理作用发泡剂e)和添加剂f)存在或不存在下进行反应,其量应使多异氰酸酯c)或含异氰酸酯基的预聚物的-NCO基与组分a)和(如使用)组分b)和任何化学作用发泡剂的活性氢之和的当量比为0.8-1.2∶1,优选0.95-1.15∶1,特别优选1.00-1.05∶1。
致密或优选是多孔PU弹性体可借助于已知的混合设备用文献中叙述的方法进行生产,例如使用一步法或优选是预聚物法。
生产致密PU弹性体时,原料组分可在无发泡剂e)存在下均匀地混合,温度通常为80-160℃,优选110-150℃,然后可将反应混合物加入加热或不加热的敞模中并使其固化。形成多孔PU弹性体时,构成组分可用同样的方法在发泡剂(优选水)存在下混合,并加入加热或不加热的模中。装填后,将模闭合并让反应混合物以例如1.1-8,优选1.2-6、特别优选2-4的密实度发泡以形成模制件。一经模制件具有足够的强度便从模中取出。脱模时间特别决定于模温、模的形状和反应混合物的反应活性,并通常是在10-60分钟范围。
用本发明方法生产的致密PU弹性体(无填料)具有的密度为1.0-1.4g/cm3,优选1.1-1.25g/cm3;有填料的产品通常的密度大于1.2g/cm3。多孔PU弹性体的密度为0.2-1.1g/cm3,优选0.35-0.80g/cm3。
用本发明方法生产的PU弹性体用于生产模制件,优选是机器结构和车辆组件。多孔PU弹性体特别适合于生产阻尼和弹性元件,例如车辆、优选是机动车辆,缓冲器和覆盖层。
实施例
对比实施例I
a)基于1,5-NDI的含异氰酸酯基预聚物的制备
将1000重量份(0.5mol)平均分子量为2000(由实验测定的羟基数计算)的聚(乙二醇(0.5mol)-1,4-丁二醇(0.5mol)己二酸酯(1mol)加热至140℃并在此温度下与240重量份(1.14mol)固体1,5-NDI混合并反应,同时剧烈搅拌。
由上述反应得到-NCO含量为4.32wt%、粘度(90℃)为2800mPa·s(用Haake公司的旋转粘度计测定,下列对比实施例和实施例中的粘度均用此方法测定)的预聚物。
b)多孔模制件的生产
交联剂组分包括下列成分:20.7重量份2,2’,6,6’-四异丙基联苯碳化二亚胺,2.9重量份平均含9个氧亚乙基单元的乙氧基化油酸和蓖麻油酸的混合物,3.8重量份C9-15烷基的正构烷基苯磺酸单乙醇胺盐,36.3重量份硫酸化蓖麻油钠盐,36.3重量份水和0.03重量份30wt%五甲基二亚乙基三胺和70wt%
N-甲基-N’-(二甲基氨基甲基)哌嗪的混合物。
将按对比实施例Ia所述制备并加热至90℃的100重量份异氰酸酯预聚物与2.4重量份交联剂组分剧烈搅拌约8秒钟,然后将反应混合物导入一加热至80℃的可封闭的金属模中,封闭模具并让反应混合物固化。25分钟后从模中取出微孔模制件并在110℃下加热16小时以进一步热固化。
对比实施例II
a)基于4,4’-MDI的含异氰酸酯基预聚物的制备
重复对比实施例Ia的步骤,但以加热至50℃的380重量份(1.52mol)的4,4’-MDI代替1,5-NDI。
如此得到了-NCO含量为6.19wt%、粘度(90℃)为1600mPa·s(用旋转粘度计测定)的预聚物。
b)多孔测试板的生产
将100重量份对比实施例IIa中所述的预聚物和3.42重量份对比实施例Ib中所述的交联剂组分用对比实施例I的方法进行反应并将反应混合物模塑成测试板。反应混合物不能被加工成动态测试用的测试弹性体。
对比实施例III
a)基于4,4’-MDI的含异氰酸酯基预聚物的制备
将1000重量份对比实施例I中所述的聚(乙二醇-1,4-丁二醇己二酸酯)和3重量份三羟甲基丙烷的混合物与380重量份(1.52mol)加热至50℃的4,4’-MDI用对比实施例II的方法进行反应。
此反应得到-NCO含量为5.80wt%、粘度(90℃)为1750mPa·s(用旋转粘度计测定)的预聚物。
b)多孔模制件的生产
用类似于对比实施例I的方法从对比实施例IIIa中所述的100重量份预聚物和对比实施例Ib中所述的3.1重量份交联剂组分生产模制件。
对比实施例IV
a)基于p-PDI的含异氰酸酯基预聚物的制备
将1000重量份(0.5mol)平均分子量为2000(由实验测定的羟基数计算)的聚(乙二醇(0.5mol)-1,4-丁二醇(0.5mol)己二酸酯(1mol)加热到100℃并在此温度下与183重量份(1.14mol)的固体p-PDI混合并反应,同时剧烈搅拌。
此反应得到-NCO基含量为4.40wt%、粘度(80℃)为2900mPa·s(用旋转粘度计测定)的预聚物。
b)多孔模制件的生产
用类似于对比实施例I的方法用100重量份对比实施例IVa所述的预聚物和2.43重量份对比实施例Ib所述的交联剂组分生产模制件,但要将对比实施例IVa的异氰酸酯预聚物加热到80℃。仅在60分钟后从模中取出模制件并于110℃加热16小时,以进一步热固化。
实施例1
a)基于4,4’-MDI/p-PDI的含异氰酸酯基预聚物的制备
将平均分子量2000(由实验测定的羟基值计算)的聚(乙二醇(0.5mol)-1,4-丁二醇(0.5mol)己二酸酯(1mol))100重量份(0.5mol)加热至130℃,在剧烈搅拌下加入174重量份(0.696mol)加热至50℃的4,4’-MDI并接着立刻加入55.75重量份(0.348mol)固体p-PDI。反应约15分钟后得到NCO含量为3.7wt%的含氨基甲酸酯和异氰酸酯基的加聚产物。此反应产物在97℃下与另外55.75重量份(0.348mol)固体p-PDI反应,并在约30分钟的时间搅拌冷却至80℃。
由此得到了NCO含量为5.77wt%、粘度(80℃)为3000mPa·s(用旋转粘度计测定)的预聚物。
b)多孔模制件的生产
将按实施例1a制备的并加热至80℃的100重量份基于4,4’-MDI/p-PDI的异氰酸酯预聚物在剧烈搅拌下与对比实施例Ib制备的3.21重量份交联剂组分混合。
在搅拌约8秒钟后,将反应混合物导入可封闭的加热至80℃的金属模中,将模闭合让反应混合物固化。在60分钟后,取出微孔模制件并在110℃下加热16小时以进一步热固化。
实施例2
a)基于4,4’-MDI/p-PDI的含异氰酸酯基预聚物的制备
重复实施例1所述方法但先将1000重量份(0.5mol)聚(乙二醇-1,4-丁二醇己二酸酯)与174重量份(0.696mol)4,4’-MDI混合并接着立刻与111.5重量份(0.696mol)p-PDI混合。
在130-90℃温度范围内反应60分钟后,得到了-NCO含量为5.70wt%、粘度(80℃)为3000mPa·s(用旋转粘度计测定)的预聚物。
b)多孔模制件的生产
多孔模制件是用实施例2a所述预聚物和类似于实施例1b的方法生产的。
根据对比实施例Ib-IVb和实施例1和2所述生产的多孔模制件用来测定微孔PU弹性体的静态和动态机械性能。
测定的静态机械性能是拉伸强度(按DIN53571)、断裂伸长(按DIN 53 571)、抗扯性(按DIN 53 515)和用DIN 53 572的修改方法测定的80℃下的残余压缩变形(使用18mm高的隔片和基面积为40×40mm、高30±1mm的测试样品)。按下列公式计算残余压缩变形(CS): 式中H0为测试样品原高(mm),
H1为测试样品变形态高度(mm),
H2为测试样品减压后高度(mm)
所测定的动态机械性能是最大力时的位移增加(WZ)和固结性(SB)(图)。用于测定固结性的模制件是一筒状测试弹性体,有三个颈形收缩,高为100mm,外径50mm,内径10mm。将弹性体处于6KN力和1.2Hz频率的100000负荷周期后,以弹性体的初始高度和最后高度差测定SB并以百分数记录。固结性是多孔PU弹性体在长期振动试验过程中的永久变形量度。固结性越低,材料的动态性能越好。
动态测试后的测定固结性的高度HR是在记录弹性体的特性曲线后测定的:H0为初始高度;模制件用最大应力(特性曲线的最大力)预压缩3倍,然后在第4周期记录特性曲线(压缩速率为V=50mm/min)。10分钟后测定H1-记录特性曲线后组件的高度。此后才开始动态测试。
HR=在23℃/50%相对大气湿度动态测试结束后贮存24小时后的动态测试后测定的最后高度。然而,动态测试后测定永久固结性用的参考点(=初始高度)为H0-弹性体在完全“新”的条件下没有任何压缩的高度。
动态测试是在23℃/50%相对空气湿度下无附加冷却的有空调设备的室内进行的。现将在测试样品上测定的机械性能总结于下表中。
表
按对比实施例I-IV和实施例1和2所述制备的多孔PU弹性体的静态和动态机械性能
实施例对比实施例 | I | II | III | IV | 1 | 2 |
异氰酸酯预聚物的基础二异氰酸酯 | NDI | MDI | MDI | p-PDI | MDI/p-PDI | MDI/p-PDI |
NCO含量[%] | 4.32 | 6.19 | 5.8 | 4.40 | 5.77 | 5.70 |
粘度(90℃)[mPa·s] | 2800 | 1600 | 1750 | 2900(80℃) | 3000(80℃) | 3000(80℃) |
静态机械性能 | ||||||
残余压缩变形[80℃,%] | 20 | 43 | 20 | 17 | 20 | 22 |
拉伸强度[N/mm2] | 3.6 | 4.5 | 4.3 | 4.1 | 4.5 | 4.6 |
伸长率[%] | 350 | 510 | 460 | 630 | 600 | 610 |
抗扯强度[N/mm] | 16.2 | 19.9 | 17.3 | 17.4 | 17.5 | 17.3 |
动态机械性能 | ||||||
固结性[%] | 8 | - | 16-18 | 6.2-7.2 | 12 | 11.7 |
位移增加[mm] | 1.4-2.1 | - | 5.0-5.7 | 1.8-2.1 | 3.0 | 2.9 |
Claims (13)
1.一种生产聚氨酯弹性体的方法,该方法是在d)、e)和f)存在或不存在下将a)和有或无b)与c)进行反应:
a)官能度为2-3和分子量为800-6000的多羟基化合物;
b)分子量达800的扩链剂和/或交联剂;
c)有机多异氰酸酯;
d)催化剂;
e)含水的发泡剂;
f)添加剂,其中所用的有机多异氰酸酯是苯-1,4-二异氰酸酯(p-PDI)和至少一种另外的选自甲苯二异氰酸酯、二苯甲烷二异氰酸酯、3,3’-二甲基联苯二异氰酸酯、1,2-二苯乙烷二异氰酸酯的芳族二异氰酸酯,和/或4-12个碳原子的脂族二异氰酸酯和/或6-18个碳原子的环脂族二异氰酸酯,其中由另外的芳族和/或脂族和/或环脂族二异氰酸酯和组分a)或a)与b)的混合物以a)或a)和b)的羟基1∶大于1-6的当量比制备含氨基甲酸酯基和异氰酸酯基的加聚产物,此产物与1,4-苯基二异氰酸酯以a)或a)和b)的羟基1∶0.02-6的当量比转化成含异氰酸酯基的预聚物,此预聚物与剩余量的a)和/或水反应形成聚氨酯弹性体。
2.权利要求1所述的方法,其中多羟基化合物a)是二官能的并具有分子量为800-3500并选自聚酯型多元醇、含羟基的聚碳酸酯和聚氧亚丁基二醇。
3.权利要求1所述的方法,其中扩链剂具有达800的分子量并选自烷二醇、一缩二烷二醇和聚氧亚烷基二醇,交联剂具有达800的分子量并选自三元或四元醇和官能度为3-4的低聚聚氧亚烷基多元醇。
4.权利要求1至3之一所述的方法,其中所用的有机多异氰酸酯c)是包括苯-1,4-二异氰酸酯(p-PDI)和至少一种另外的选自甲苯二异氰酸酯、二苯甲烷二异氰酸酯、3,3’-二甲基联苯二异氰酸酯、1,2-二苯基乙烷二异氰酸酯、和/或六亚甲基-1,6-二异氰酸酯和/或1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷的二异氰酸酯的可流动混合物。
5.权利要求1至3之一所述的方法,其中有机多异氰酸酯c)是以含异氰酸酯基的预聚物形式使用的,预聚物的制备是将多羟基化合物a)或a)和扩链剂和/或交联剂b)的混合物与选自甲苯二异氰酸酯、二苯甲烷二异氰酸酯、3,3’-二甲基联苯二异氰酸酯、1,2-二苯乙烷二异氰酸酯的芳族二异氰酸酯、和/或六亚甲基-1,6-二异氰酸酯和/或1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷以a)的羟基或a)和b)的羟基对有机二异氰酸酯的异氰酸酯基的当量比1∶大于1-6进行反应得到含氨基甲酸酯和异氰酸酯基的加聚产物,并将此加聚产物与苯-1,4-二异氰酸酯(p-PDI)以a)的羟基或a)和b)的羟基对苯-1,4-二异氰酸酯的异氰酸酯基的当量比1∶0.02-6进行反应以形成含异氰酸酯基的预聚物。
6.权利要求1至3之一所述的方法,其中有机多异氰酸酯c)是以含异氰酸酯基的预聚物形式使用的,预聚物的制备是将多羟基化合物a)或a)和扩链剂和/或交联剂b)的混合物与二苯甲烷-4,4’-二异氰酸酯以羟基对异氰酸酯基当量比1∶大于1-6进行反应以得到含氨基甲酸酯和异氰酸酯基的加聚产物,再将此加聚产物与苯-1,4-二异氰酸酯(p-PDI)以a)的羟基或a)和b)的羟基对苯-1,4-二异氰酸酯的异氰酸酯基当量比1∶0.02-6进行反应形成含异氰酸酯基的预聚物。
7.权利要求1至3任一项所述的方法,其中该聚氨酯弹性体是多孔的和发泡剂d)选自4-8个碳原子的烷烃,4-6个碳原子的环烷烃和水。
8.权利要求1至3之一所述的方法,其中该聚氨酯弹性体是多孔的和其密度为0.2-1.1g/l。
9.一种含异氰酸酯基的预聚物,该预聚物的-NCO含量为3.3-10wt %且其制备是将至少一种多羟基化合物a)或a)和扩链剂和/或交联剂b)的混合物与至少一种选自甲苯二异氰酸酯、二苯甲烷二异氰酸酯、3,3’-二甲基联苯二异氰酸酯、1,2-二苯乙烷二异氰酸酯的芳族二异氰酸酯、和/或六亚甲基-1,6-二异氰酸酯和/或1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷进行反应以得到含氨基甲酸酯和异氰酸酯基的加聚产物,其-NCO含量为0.05-8wt%,再将此加聚产物与苯-1,4-二异氰酸酯(p-PDI)反应以形成含异氰酸酯基的预聚物。
10.权利要求9所述的含异氰酸酯基的预聚物,其中a)的羟基或a)和b)的羟基对选自甲苯二异氰酸酯、二苯甲烷二异氰酸酯、3,3’-二甲基联苯二异氰酸酯、1,2-二苯乙烷二异氰酸酯的芳族二异氰酸酯、和/或六亚甲基-1,6-二异氰酸酯和/或1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷的-NCO基对苯-1,4-二异氰酸酯(p-PDI)的-NCO基的当量比为1∶大于1-6∶0.02-6。
11.一种含异氰酸酯基的预聚物,该预聚物的-NCO含量为3.3-10wt %并且其制备是将至少一种多羟基化合物a)或a)和扩链剂和/或交联剂b)的混合物与二苯甲烷-4,4’-二异氰酸酯进行反应以得到含氨基甲酸酯和异氰酸酯基的加聚产物,其-NCO含量为0.05-8wt%,再将此加聚产物与苯-1,4-二异氰酸酯(p-PDI)反应以得到含异氰酸酯基的预聚物。
12.一种含异氰酸酯基的预聚物,该预聚物的-NCO含量为3.3-10wt %并且其制备是将分子量>800-3500并选自聚酯型多元醇、含羟基的聚碳酸酯和聚氧四亚甲基二醇的二官能多羟基化合物与二苯甲烷-4,4’-二异氰酸酯反应以得到含氨基甲酸酯和异氰酸酯基的加聚产物,再将此加聚产物与苯-1,4-二异氰酸酯(p-PDI)反应以得到含异氰酸酯基的预聚物。
13.权利要求11或12所述的含异氰酸酯基的预聚物,其中a)的羟基或a)和b)的羟基对二苯甲烷-4,4’-二异氰酸酯的NCO基对苯-1,4-二异氰酸酯的NCO基的当量比为1∶大于1-6∶0.02-6。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19627907A DE19627907A1 (de) | 1996-07-11 | 1996-07-11 | Verfahren zur Herstellung von kompakten oder zelligen Polyurethan-Elastomeren und hierfür geeignete Isocyanatprepolymere |
DE19627907.0 | 1996-07-11 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1225104A CN1225104A (zh) | 1999-08-04 |
CN1104451C true CN1104451C (zh) | 2003-04-02 |
Family
ID=7799516
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN97196259A Expired - Fee Related CN1104451C (zh) | 1996-07-11 | 1997-06-30 | 致密或多孔聚氨酯弹性体的生产方法及适合于此目的的异氰酸酯预聚物 |
Country Status (18)
Country | Link |
---|---|
US (1) | US6197839B1 (zh) |
EP (1) | EP0910596B1 (zh) |
JP (1) | JP2000514484A (zh) |
KR (1) | KR20000023685A (zh) |
CN (1) | CN1104451C (zh) |
AR (1) | AR013597A1 (zh) |
AT (1) | ATE217016T1 (zh) |
AU (1) | AU728982B2 (zh) |
BR (1) | BR9710233A (zh) |
CA (1) | CA2259934A1 (zh) |
CZ (1) | CZ7699A3 (zh) |
DE (2) | DE19627907A1 (zh) |
EA (1) | EA003631B1 (zh) |
ES (1) | ES2176754T3 (zh) |
PL (1) | PL331073A1 (zh) |
TR (1) | TR199900026T2 (zh) |
WO (1) | WO1998002476A1 (zh) |
ZA (1) | ZA976127B (zh) |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6713151B1 (en) | 1998-06-24 | 2004-03-30 | Honeywell International Inc. | Compliant fibrous thermal interface |
US6784219B2 (en) | 1999-01-30 | 2004-08-31 | Bayer Aktiengesellschaft | Polyurethane cast elastomers based on durene diisocyanate |
DE50004222D1 (de) * | 1999-07-02 | 2003-12-04 | Rhein Chemie Rheinau Gmbh | Katalysator-System für die NCO/OH-Reaktion (Polyurethanbildung) |
KR20010054080A (ko) * | 1999-12-03 | 2001-07-02 | 조형래 | 고탄성 발포우레탄수지의 제조방법 |
USH2233H1 (en) * | 2000-08-07 | 2009-11-03 | Air Products And Chemicals, Inc. | Catalysts which stabilize hydrofluorocarbon blowing agents in polyurethane foam compositions |
JP3683526B2 (ja) * | 2000-12-20 | 2005-08-17 | 匡 永井 | ポリウレタン多孔質体及びその製造方法 |
WO2002081537A1 (de) * | 2001-04-06 | 2002-10-17 | Basf Aktiengesellschaft | Zellige polyisocyanat-polyadditionsprodukte |
US6777533B2 (en) | 2001-12-21 | 2004-08-17 | Basf Corporation | Production of polyetherols using aluminum phosphonate catalysts |
US20060183882A1 (en) * | 2001-12-21 | 2006-08-17 | Dexheimer Edward M | Continuous process for preparation of polyether polyols |
US6919486B2 (en) * | 2001-12-21 | 2005-07-19 | Basf Corporation | Polyetherols produced using aluminium phosphonate catalysts |
US20060281894A1 (en) * | 2005-06-13 | 2006-12-14 | Basf Corporation. | Method of forming polyetherols in the presence of aluminum phosphate catalysts |
US6706844B2 (en) | 2001-12-21 | 2004-03-16 | Basf Corporation | Polyurethane products produced from aluminum phosphonate catalyzed polyetherols |
US7226988B1 (en) | 2001-12-21 | 2007-06-05 | Basf Corporation | Method of forming polyetherols in the presence of carboxy-modified aluminum-based catalysts |
US20040154718A1 (en) * | 2003-02-06 | 2004-08-12 | Doesburg Van I. | Polyurethane filled tire and method of making same |
DE102005003057A1 (de) * | 2005-01-22 | 2006-07-27 | Henkel Kgaa | Spritzbare, niedrigviskose Kautschuk-Dämpfungsmassen |
US20060281892A1 (en) * | 2005-06-14 | 2006-12-14 | Basf Corporation | Polyurethane products including aluminum phosphates |
DE102006030391A1 (de) * | 2006-07-01 | 2008-01-10 | Bayer Materialscience Ag | Geschäumte und massive Polyurethanelastomere auf Basis von 1,5-Naphthalindiisocyanat, Verfahren zu ihrer Herstellung und ihre Verwendung |
JP5211452B2 (ja) * | 2006-08-29 | 2013-06-12 | Nok株式会社 | 発泡ポリウレタンエラストマーの製造方法 |
DE102008051882A1 (de) | 2008-10-16 | 2010-04-29 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyetheresterpolyolen |
CN101942786B (zh) * | 2010-08-25 | 2012-06-27 | 北京科聚化工新材料有限公司 | 一种铁轨垫板及其制备方法 |
JP5609460B2 (ja) * | 2010-09-14 | 2014-10-22 | Nok株式会社 | 熱可塑性ポリウレタンエラストマーの製造法 |
US20140329985A1 (en) | 2010-12-20 | 2014-11-06 | Klaus Lorenz | Method for producing polyether ester polyols |
JP2012214779A (ja) * | 2011-03-30 | 2012-11-08 | Asahi Glass Co Ltd | 軟質ポリウレタンフォームの製造方法およびシート |
JP5969252B2 (ja) * | 2012-04-04 | 2016-08-17 | 東洋ゴム工業株式会社 | 硬質ポリウレタンフォームパネル |
CN103788332B (zh) * | 2012-11-02 | 2016-03-30 | 上海凯众材料科技股份有限公司 | Ndi改性mdi基聚氨酯微孔弹性体的制备方法 |
JP6159036B1 (ja) * | 2015-08-18 | 2017-07-05 | 三井化学株式会社 | 発泡ポリウレタン材料、成形品、および、発泡ポリウレタン材料の製造方法 |
EP3741788A1 (de) | 2019-05-24 | 2020-11-25 | Covestro Deutschland AG | Verfahren zur herstellung von polyoxyalkylenpolyol-mischungen |
EP3838963A1 (de) | 2019-12-17 | 2021-06-23 | Covestro Deutschland AG | Verfahren zur herstellung von polyoxyalkylenpolyesterpolyolen |
WO2022096390A1 (de) | 2020-11-06 | 2022-05-12 | Covestro Deutschland Ag | Verfahren zur herstellung eines polyol-gemisches |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4191818A (en) * | 1975-10-25 | 1980-03-04 | Basf Wyandotte Corporation | Process for preparing heat-resistant polyurethane elastomers having no secondary softening range |
GB2118955A (en) * | 1982-04-23 | 1983-11-09 | Teroson Gmbh | Polyurethanes |
EP0316150A2 (en) * | 1987-11-11 | 1989-05-17 | Nippon Polyurethane Industry Co. Ltd. | Thermosetting urethane elastomer |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB118955A (en) | 1917-12-03 | 1918-09-19 | John Edwin Gwynn | Improvements in Deflecting Plates for use in the Smoke Boxes of Locomotives. |
DE19538330A1 (de) * | 1995-10-14 | 1997-04-17 | Basf Ag | Verfahren zur Herstellung von kompakten oder zelligen Polyurethan-Elastomeren auf Basis von 3,3'-Dimethyl-diphenyl-4,4'-diisocyanat enthaltenden Polyisocyanatmischungen und hierfür geeignete Isocyanatpräpolymere |
-
1996
- 1996-07-11 DE DE19627907A patent/DE19627907A1/de not_active Withdrawn
-
1997
- 1997-06-30 EP EP97930440A patent/EP0910596B1/de not_active Expired - Lifetime
- 1997-06-30 US US09/214,730 patent/US6197839B1/en not_active Expired - Fee Related
- 1997-06-30 WO PCT/EP1997/003396 patent/WO1998002476A1/de not_active Application Discontinuation
- 1997-06-30 AU AU34390/97A patent/AU728982B2/en not_active Ceased
- 1997-06-30 AT AT97930440T patent/ATE217016T1/de not_active IP Right Cessation
- 1997-06-30 BR BR9710233A patent/BR9710233A/pt not_active Application Discontinuation
- 1997-06-30 EA EA199900024A patent/EA003631B1/ru not_active IP Right Cessation
- 1997-06-30 ES ES97930440T patent/ES2176754T3/es not_active Expired - Lifetime
- 1997-06-30 CA CA002259934A patent/CA2259934A1/en not_active Abandoned
- 1997-06-30 PL PL97331073A patent/PL331073A1/xx unknown
- 1997-06-30 CN CN97196259A patent/CN1104451C/zh not_active Expired - Fee Related
- 1997-06-30 DE DE59707166T patent/DE59707166D1/de not_active Expired - Lifetime
- 1997-06-30 JP JP10505548A patent/JP2000514484A/ja active Pending
- 1997-06-30 TR TR1999/00026T patent/TR199900026T2/xx unknown
- 1997-06-30 CZ CZ9976A patent/CZ7699A3/cs unknown
- 1997-07-10 ZA ZA976127A patent/ZA976127B/xx unknown
- 1997-07-11 AR ARP970103087A patent/AR013597A1/es unknown
-
1999
- 1999-01-09 KR KR1019997000142A patent/KR20000023685A/ko not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4191818A (en) * | 1975-10-25 | 1980-03-04 | Basf Wyandotte Corporation | Process for preparing heat-resistant polyurethane elastomers having no secondary softening range |
GB2118955A (en) * | 1982-04-23 | 1983-11-09 | Teroson Gmbh | Polyurethanes |
EP0316150A2 (en) * | 1987-11-11 | 1989-05-17 | Nippon Polyurethane Industry Co. Ltd. | Thermosetting urethane elastomer |
Also Published As
Publication number | Publication date |
---|---|
TR199900026T2 (xx) | 1999-03-22 |
EA199900024A1 (ru) | 1999-06-24 |
CN1225104A (zh) | 1999-08-04 |
KR20000023685A (ko) | 2000-04-25 |
AU728982B2 (en) | 2001-01-25 |
ZA976127B (en) | 1999-01-11 |
EP0910596A1 (de) | 1999-04-28 |
CZ7699A3 (cs) | 1999-07-14 |
DE19627907A1 (de) | 1998-01-15 |
AU3439097A (en) | 1998-02-09 |
BR9710233A (pt) | 1999-08-10 |
EA003631B1 (ru) | 2003-08-28 |
AR013597A1 (es) | 2001-01-10 |
US6197839B1 (en) | 2001-03-06 |
ES2176754T3 (es) | 2002-12-01 |
DE59707166D1 (de) | 2002-06-06 |
EP0910596B1 (de) | 2002-05-02 |
PL331073A1 (en) | 1999-06-21 |
CA2259934A1 (en) | 1998-01-22 |
JP2000514484A (ja) | 2000-10-31 |
WO1998002476A1 (de) | 1998-01-22 |
ATE217016T1 (de) | 2002-05-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1104451C (zh) | 致密或多孔聚氨酯弹性体的生产方法及适合于此目的的异氰酸酯预聚物 | |
CN1154679C (zh) | 致密或多孔聚氨酯弹性体的生产方法及适合于此目的的异氰酸酯预聚物 | |
CN1099431C (zh) | 基于多异氰酸酯混合物的致密或多孔聚氨酯弹性体的生产方法及异氰酸酯预聚物 | |
AU766760B2 (en) | Improved cellular or elastomeric plastic material | |
CN1070506C (zh) | 聚氨酯泡沫的制备方法 | |
US5143945A (en) | Carboxylic acid modified carbon dioxide co-blown polyurethane-polyisocyanurate foams | |
CN101668787B (zh) | 软质聚氨酯泡沫用多异氰酸酯组合物以及使用该组合物制造软质聚氨酯泡沫的方法 | |
CN1241965C (zh) | 多孔聚异氰酸酯聚加合物 | |
EP0409199A2 (en) | Rigid polyurethanepolyisocyanurate foams and process for preparing the same | |
CN1226337C (zh) | 一种含碳化二亚胺的混合物和一种聚氨酯的制备方法 | |
CN1212971A (zh) | 生产具有低导热性的硬质聚氨酯泡沫 | |
CN1759129A (zh) | 低胺排放的聚氨酯泡沫塑料 | |
CN1173508A (zh) | 有改进的固化性的聚氨酯的制备方法 | |
CN1478111A (zh) | 改进聚氨酯泡沫体性能的方法 | |
US4136241A (en) | Flexible polyurethane foams based upon the use of a soluble amine salt as crosslinking agent | |
CN1050726A (zh) | 多元醇、聚氨酯树脂及其应用 | |
CN1074009C (zh) | 储存稳定、含阻燃剂的多元醇成分 | |
JP2002356535A (ja) | 硬質ポリウレタンフォーム用ポリイソシアネート組成物、及びそれを用いた硬質ポリウレタンフォームの製造方法 | |
US5756636A (en) | Isocyanate prepolymers produced from toluene diisocyanate residue dissolved in toluene diisocyanate | |
CN1204346A (zh) | 制备任选含有增强材料、由多异氰酸酯聚合加成产物和内脱模剂的自脱模的致密或多孔模塑 | |
JP4495296B2 (ja) | ポリウレタンフォーム | |
JPH02250884A (ja) | ウレタンフォーム、その製造方法及びアルコキシレート四級アンモニウムホウ酸エステル塩の製造方法 | |
CN110272529A (zh) | 聚氨酯块状泡沫形成用组合物、聚氨酯块状泡沫、及其制造方法 | |
MXPA98002856A (en) | Production of compact or cellular polyurethane elastomers based on polynocyanate mixtures, containing 3,3'-dimethylphyenyl 4,4'-diisocyanate and isocyanate prepolimers, suitable for this proposal | |
JP2002356532A (ja) | 硬質ポリウレタンフォーム用ポリイソシアネート組成物、及びそれを用いた硬質ポリウレタンフォームの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C19 | Lapse of patent right due to non-payment of the annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |