TW201000508A - Thermoset polyurethanes - Google Patents
Thermoset polyurethanes Download PDFInfo
- Publication number
- TW201000508A TW201000508A TW098116888A TW98116888A TW201000508A TW 201000508 A TW201000508 A TW 201000508A TW 098116888 A TW098116888 A TW 098116888A TW 98116888 A TW98116888 A TW 98116888A TW 201000508 A TW201000508 A TW 201000508A
- Authority
- TW
- Taiwan
- Prior art keywords
- polyisocyanate
- adduct
- composition
- isocyanate
- weight
- Prior art date
Links
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 42
- 239000004814 polyurethane Substances 0.000 title claims abstract description 41
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 26
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 73
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 73
- -1 aromatic diol Chemical class 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 66
- 229920000768 polyamine Polymers 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 150000001412 amines Chemical class 0.000 claims description 32
- 239000011368 organic material Substances 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 239000006260 foam Substances 0.000 claims description 23
- 239000012948 isocyanate Substances 0.000 claims description 22
- 229920005862 polyol Polymers 0.000 claims description 22
- 150000003077 polyols Chemical class 0.000 claims description 22
- 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 22
- 150000002513 isocyanates Chemical class 0.000 claims description 20
- 239000004970 Chain extender Substances 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
- 125000001033 ether group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- 125000005442 diisocyanate group Chemical group 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052797 bismuth Inorganic materials 0.000 claims description 8
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000002009 diols Chemical class 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 239000011733 molybdenum Substances 0.000 claims description 5
- 229920000582 polyisocyanurate Polymers 0.000 claims description 5
- 239000011495 polyisocyanurate Substances 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 125000002524 organometallic group Chemical group 0.000 claims description 4
- 229920006389 polyphenyl polymer Polymers 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- 229920002396 Polyurea Polymers 0.000 claims description 2
- LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical class C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 claims description 2
- 238000005266 casting Methods 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001983 dialkylethers Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000004616 structural foam Substances 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 4
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- HSTCJLDQVIIDKF-UHFFFAOYSA-N 1-phenyldecylbenzene Chemical compound C=1C=CC=CC=1C(CCCCCCCCC)C1=CC=CC=C1 HSTCJLDQVIIDKF-UHFFFAOYSA-N 0.000 claims 1
- 229910000831 Steel Inorganic materials 0.000 claims 1
- 239000011247 coating layer Substances 0.000 claims 1
- VLWBWEUXNYUQKJ-UHFFFAOYSA-N cobalt ruthenium Chemical compound [Co].[Ru] VLWBWEUXNYUQKJ-UHFFFAOYSA-N 0.000 claims 1
- 229910000071 diazene Inorganic materials 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- ONMKQWPCMAOKQN-UHFFFAOYSA-N phthalic acid;urea Chemical compound NC(N)=O.OC(=O)C1=CC=CC=C1C(O)=O ONMKQWPCMAOKQN-UHFFFAOYSA-N 0.000 claims 1
- 239000010959 steel Substances 0.000 claims 1
- 239000003822 epoxy resin Substances 0.000 abstract description 48
- 229920000647 polyepoxide Polymers 0.000 abstract description 48
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 46
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 41
- 239000000047 product Substances 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000000376 reactant Substances 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
- 239000011521 glass Substances 0.000 description 31
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 26
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 24
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 23
- 238000000034 method Methods 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 16
- 239000012299 nitrogen atmosphere Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 229920001223 polyethylene glycol Polymers 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 238000004448 titration Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 12
- 239000008367 deionised water Substances 0.000 description 12
- 229910021641 deionized water Inorganic materials 0.000 description 12
- 239000012975 dibutyltin dilaurate Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- 238000005516 engineering process Methods 0.000 description 10
- 238000012937 correction Methods 0.000 description 9
- 238000006735 epoxidation reaction Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000004364 calculation method Methods 0.000 description 8
- 238000002390 rotary evaporation Methods 0.000 description 8
- 239000002841 Lewis acid Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 150000007517 lewis acids Chemical class 0.000 description 7
- 239000011572 manganese Substances 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- 239000004604 Blowing Agent Substances 0.000 description 6
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000003109 Karl Fischer titration Methods 0.000 description 5
- CJYXWRJSNYKHFN-UHFFFAOYSA-N N=C=O.N=C=O.C1=CNC2=CC=CC=C12 Chemical compound N=C=O.N=C=O.C1=CNC2=CC=CC=C12 CJYXWRJSNYKHFN-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 239000008267 milk Substances 0.000 description 4
- 235000013336 milk Nutrition 0.000 description 4
- 210000004080 milk Anatomy 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
- 230000009257 reactivity Effects 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNNXXFFLRWCPBC-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C1=CC=CC=C1 DNNXXFFLRWCPBC-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 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
- LUSFFPXRDZKBMF-OCAPTIKFSA-N [(1s,3r)-3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@H]1CCC[C@@H](CO)C1 LUSFFPXRDZKBMF-OCAPTIKFSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000004880 explosion Methods 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 239000004088 foaming agent Substances 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 229910052746 lanthanum Inorganic materials 0.000 description 3
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000005498 phthalate group Chemical group 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 3
- 238000004457 water analysis Methods 0.000 description 3
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical compound NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- ZKEKKQBGGZMVCG-UHFFFAOYSA-N CN(C)CCCCCCCCCC.NN Chemical compound CN(C)CCCCCCCCCC.NN ZKEKKQBGGZMVCG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 2
- LUSFFPXRDZKBMF-YUMQZZPRSA-N [(1s,3s)-3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@H]1CCC[C@H](CO)C1 LUSFFPXRDZKBMF-YUMQZZPRSA-N 0.000 description 2
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 description 2
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1477—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5523508P | 2008-05-22 | 2008-05-22 |
Publications (1)
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|---|---|
| TW201000508A true TW201000508A (en) | 2010-01-01 |
Family
ID=40846065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW098116888A TW201000508A (en) | 2008-05-22 | 2009-05-21 | Thermoset polyurethanes |
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|---|---|
| US (1) | US20110054056A1 (enExample) |
| EP (1) | EP2291425A1 (enExample) |
| JP (1) | JP2011521074A (enExample) |
| CN (1) | CN102027034A (enExample) |
| TW (1) | TW201000508A (enExample) |
| WO (1) | WO2009142899A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013538918A (ja) | 2010-09-30 | 2013-10-17 | ダウ グローバル テクノロジーズ エルエルシー | エポキシ樹脂アダクトおよびその熱硬化樹脂 |
| JP5854360B2 (ja) | 2010-09-30 | 2016-02-09 | ブルー キューブ アイピー エルエルシー | 熱硬化性組成物およびその熱硬化物 |
| US8962792B2 (en) | 2010-09-30 | 2015-02-24 | Dow Global Technologies Llc | Process for preparing epoxy resins |
| WO2012044443A1 (en) | 2010-09-30 | 2012-04-05 | Dow Global Technologies Llc | Epoxy resin compositions |
| JP5795804B2 (ja) | 2010-09-30 | 2015-10-14 | ダウ グローバル テクノロジーズ エルエルシー | コーティング組成物 |
| CN108277554A (zh) * | 2017-12-21 | 2018-07-13 | 苏州浩洋聚氨酯科技有限公司 | 一种新型聚氨酯纤维 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3001973A (en) | 1953-05-23 | 1961-09-26 | Bayer Ag | Production of cross-linked plastics |
| BE539937A (enExample) | 1954-07-20 | |||
| DE1027394B (de) | 1956-10-22 | 1958-04-03 | Bayer Ag | Verfahren zur Herstellung von Schaumstoffen |
| GB889050A (en) | 1959-06-12 | 1962-02-07 | Ici Ltd | Process for the manufacture of polyurethanes |
| US3152162A (en) | 1959-07-29 | 1964-10-06 | Bayer Ag | Polyisocyanate-carbodiimide adducts and process for the production thereof |
| NL272185A (enExample) | 1960-12-05 | |||
| GB994890A (en) | 1961-12-18 | 1965-06-10 | Ici Ltd | New organic polyisocyanates and their manufacture |
| US3154522A (en) | 1962-04-20 | 1964-10-27 | Air Prod & Chem | Polyisocyanurate preparation using a triethylene diamine and a tertiary imine co-catalyst |
| US3124605A (en) | 1963-12-05 | 1964-03-10 | Biuret polyisocyanates | |
| DE1222067B (de) | 1964-11-07 | 1966-08-04 | Bayer Ag | Verfahren zur Herstellung von einheitlichen organischen Polyisocyanaten |
| DE1231688B (de) | 1965-04-17 | 1967-01-05 | Bayer Ag | Verfahren zur Herstellung von Isocyanatocarbonsaeureestern polyfunktioneller Hydroxyverbindungen |
| DE1230778B (de) | 1965-05-24 | 1966-12-22 | Bayer Ag | Verfahren zur Herstellung von acylierten Harnstoffpolyisocyanaten |
| US3394164A (en) | 1965-10-24 | 1968-07-23 | Upjohn Co | Stabilized methylenebis-(phenyl isocyanate) compositions |
| US3567763A (en) | 1966-01-06 | 1971-03-02 | Rohm & Haas | Ester polyisocyanates |
| DE2002064C2 (de) | 1970-01-17 | 1983-09-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von flammwidrigen elastischen oder halbelastischen Schaumstoffen |
| US4163815A (en) * | 1977-09-19 | 1979-08-07 | Ford Motor Company | Catalyzed polyisocyanate coating compositions |
| US4167612A (en) * | 1978-06-19 | 1979-09-11 | Wm. T. Burnett & Co., Inc. | Flexible polyurethane foams having low resistance to air flow and method for preparation |
| JPS63213576A (ja) * | 1987-03-02 | 1988-09-06 | Asahi Denka Kogyo Kk | 被覆用樹脂組成物 |
| US5019602A (en) * | 1989-12-12 | 1991-05-28 | Premier Industrial Corporation | Polyurethane foams, compositions to prepare same and process to prepare same |
| US5236995A (en) * | 1991-03-26 | 1993-08-17 | Basf Corporation | Post-extended anionic polyurethane dispersion |
| US5310770A (en) * | 1992-12-30 | 1994-05-10 | Hi-Tek Polymers, Inc. | Water reducible epoxy-amine adducts based on the diglycidyl ether of cyclohexane dimethanol |
| US5591812A (en) * | 1996-01-26 | 1997-01-07 | Air Products And Chemicals, Inc. | Reactive accelerators for amine cured epoxy resins |
| AU2001285810A1 (en) * | 2000-07-11 | 2002-01-21 | Vantico Ag | High functional polymers |
| US6734273B2 (en) * | 2001-02-12 | 2004-05-11 | Noveon Ip Holdings Corp. | High molecular weight thermoplastic polyurethanes made from polyols having high secondary hydroxyl content |
| WO2002068131A1 (en) * | 2001-02-17 | 2002-09-06 | Hehr International Inc. | Polyamine-epoxide adduct and polyurea prepared therefrom |
| JP2006037037A (ja) * | 2004-07-30 | 2006-02-09 | Toyo Ink Mfg Co Ltd | 接着剤組成物 |
| US7425594B2 (en) * | 2005-11-23 | 2008-09-16 | Ppg Industries Ohio, Inc. | Copolymer of glycidyl ester and/or ether with polyol |
| RU2008135693A (ru) * | 2006-02-03 | 2010-03-10 | Дау Глобал Текнолоджиз Инк. (Us) | Мономеры и полимеры на основе 1,3/1,4-циклогександиметанола |
| US8530534B2 (en) * | 2006-05-04 | 2013-09-10 | Air Products And Chemicals, Inc. | Trimerization catalysts from sterically hindered salts |
| BRPI0711003A2 (pt) * | 2006-05-18 | 2011-08-23 | Dow Global Technologies Inc | dispersão de poliuretano aquoso, uso de uma dispersão de poliuretano aquosa e polìmero de poliuretano |
| EP1916269A1 (de) * | 2006-10-24 | 2008-04-30 | Sika Technology AG | Blockierte Polyurethanprepolymere und hitzehärtende Epoxidharzzusammensetzungen |
| JP5506659B2 (ja) * | 2007-03-29 | 2014-05-28 | ルブリゾル アドバンスド マテリアルズ， インコーポレイテッド | １，３−シクロヘキサンジメタノールおよび１，４−シクロヘキサンジメタノールを含む鎖伸長剤の混合物を使用する低ヘイズ熱可塑性ポリウレタン |
| DE602008002592D1 (de) * | 2007-05-21 | 2010-10-28 | Lubrizol Advanced Mat Inc | Harte, aliphatische thermoplastische Polyurethane |
| US8318834B2 (en) * | 2008-05-22 | 2012-11-27 | Dow Global Technologies Llc | Epoxy resin reactive diluent compositions |
| US20110039982A1 (en) * | 2008-05-22 | 2011-02-17 | Hefner Jr Robert E | Epoxy resins and processes for preparing the same |
| WO2009142898A1 (en) * | 2008-05-22 | 2009-11-26 | Dow Global Technologies Inc. | Adducts of epoxy resins and process for preparing the same |
| JP5124534B2 (ja) * | 2009-06-30 | 2013-01-23 | ダンロップスポーツ株式会社 | ゴルフボール |
-
2009
- 2009-05-04 JP JP2011510551A patent/JP2011521074A/ja active Pending
- 2009-05-04 EP EP09751128A patent/EP2291425A1/en not_active Withdrawn
- 2009-05-04 WO PCT/US2009/042644 patent/WO2009142899A1/en not_active Ceased
- 2009-05-04 CN CN2009801170420A patent/CN102027034A/zh active Pending
- 2009-05-04 US US12/989,480 patent/US20110054056A1/en not_active Abandoned
- 2009-05-21 TW TW098116888A patent/TW201000508A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20110054056A1 (en) | 2011-03-03 |
| WO2009142899A1 (en) | 2009-11-26 |
| EP2291425A1 (en) | 2011-03-09 |
| JP2011521074A (ja) | 2011-07-21 |
| CN102027034A (zh) | 2011-04-20 |
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