TW492984B - Isocyanate-terminated prepolymers or quasiprepolymers, polyurethane elastomers, and methods of increasing the physical properties of chain-extended polyurethane elastomers - Google Patents
Isocyanate-terminated prepolymers or quasiprepolymers, polyurethane elastomers, and methods of increasing the physical properties of chain-extended polyurethane elastomers Download PDFInfo
- Publication number
- TW492984B TW492984B TW085115787A TW85115787A TW492984B TW 492984 B TW492984 B TW 492984B TW 085115787 A TW085115787 A TW 085115787A TW 85115787 A TW85115787 A TW 85115787A TW 492984 B TW492984 B TW 492984B
- Authority
- TW
- Taiwan
- Prior art keywords
- prepolymer
- polyol
- isocyanate
- weight
- glycol
- Prior art date
Links
- 229920003225 polyurethane elastomer Polymers 0.000 title claims abstract description 18
- 230000000704 physical effect Effects 0.000 title abstract description 10
- 238000000034 method Methods 0.000 title abstract description 8
- 229920005862 polyol Polymers 0.000 claims abstract description 106
- 150000003077 polyols Chemical class 0.000 claims abstract description 106
- -1 polyoxypropylene Polymers 0.000 claims abstract description 53
- 229920001451 polypropylene glycol Polymers 0.000 claims abstract description 46
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 55
- 229920001971 elastomer Polymers 0.000 claims description 51
- 239000000806 elastomer Substances 0.000 claims description 51
- 239000012948 isocyanate Substances 0.000 claims description 41
- 150000002513 isocyanates Chemical class 0.000 claims description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 28
- 150000002009 diols Chemical class 0.000 claims description 25
- 238000011049 filling Methods 0.000 claims description 25
- 239000004970 Chain extender Substances 0.000 claims description 19
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- 239000005056 polyisocyanate Substances 0.000 claims description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 8
- 229920001610 polycaprolactone Polymers 0.000 claims description 7
- 239000004632 polycaprolactone Substances 0.000 claims description 7
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- 150000004984 aromatic diamines Chemical group 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006353 oxyethylene group Chemical group 0.000 claims description 2
- 125000003827 glycol group Chemical group 0.000 claims 1
- 238000009434 installation Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000005702 oxyalkylene group Chemical group 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 abstract description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 1
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 229920005906 polyester polyol Polymers 0.000 description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 230000002079 cooperative effect Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 241000894007 species Species 0.000 description 8
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 3
- VDJBIPLKIGSVRG-UHFFFAOYSA-N 3-chloro-2,6-diethylaniline Chemical compound CCC1=CC=C(Cl)C(CC)=C1N VDJBIPLKIGSVRG-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- IZLAVFWQHMDDGK-UHFFFAOYSA-N gold(1+);cyanide Chemical compound [Au+].N#[C-] IZLAVFWQHMDDGK-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 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 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- CDCFKVCOZYCTBR-UHFFFAOYSA-J osmium(4+);tetrahydroxide Chemical class [OH-].[OH-].[OH-].[OH-].[Os+4] CDCFKVCOZYCTBR-UHFFFAOYSA-J 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- BJZYYSAMLOBSDY-QMMMGPOBSA-N (2s)-2-butoxybutan-1-ol Chemical compound CCCCO[C@@H](CC)CO BJZYYSAMLOBSDY-QMMMGPOBSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical class O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- AXKZIDYFAMKWSA-UHFFFAOYSA-N 1,6-dioxacyclododecane-7,12-dione Chemical compound O=C1CCCCC(=O)OCCCCO1 AXKZIDYFAMKWSA-UHFFFAOYSA-N 0.000 description 1
- PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical class C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 description 1
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
- SMZFUMFLNCWTFX-UHFFFAOYSA-N 1-methylidene-2H-pyrene Chemical compound C=C1CC=C2C=CC3=CC=CC4=CC=C1C2=C34 SMZFUMFLNCWTFX-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- OQDDFOFVIFIUME-UHFFFAOYSA-N 2-(2-hydroxyethyl)benzene-1,4-diol Chemical compound OCCC1=CC(O)=CC=C1O OQDDFOFVIFIUME-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 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
- NKFIBMOQAPEKNZ-UHFFFAOYSA-N 5-amino-1h-indole-2-carboxylic acid Chemical compound NC1=CC=C2NC(C(O)=O)=CC2=C1 NKFIBMOQAPEKNZ-UHFFFAOYSA-N 0.000 description 1
- BTQLWKNIJDKIAB-UHFFFAOYSA-N 6-methylidene-n-phenylcyclohexa-2,4-dien-1-amine Chemical class C=C1C=CC=CC1NC1=CC=CC=C1 BTQLWKNIJDKIAB-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- WOFVPNPAVMKHCX-UHFFFAOYSA-N N#C[Au](C#N)C#N Chemical class N#C[Au](C#N)C#N WOFVPNPAVMKHCX-UHFFFAOYSA-N 0.000 description 1
- 229920000562 Poly(ethylene adipate) Polymers 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- BQODPTQLXVVEJG-UHFFFAOYSA-N [O].C=C Chemical group [O].C=C BQODPTQLXVVEJG-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
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920003054 adipate polyester Polymers 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000013627 low molecular weight specie Chemical group 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 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
- 229940098465 tincture Drugs 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 150000004998 toluenediamines Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4866—Polyethers having a low unsaturation value
-
- 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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- 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
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4808—Mixtures of two or more polyetherdiols
-
- 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
- C08G2250/00—Compositions for preparing crystalline polymers
Landscapes
- 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 |
|---|---|---|---|
| US08/577,959 US5648447A (en) | 1995-12-22 | 1995-12-22 | Elastomeric polyurethanes with improved properties based on crystallizable polyols in combination with low monol polyoxpropylene polyols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW492984B true TW492984B (en) | 2002-07-01 |
Family
ID=24310863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW085115787A TW492984B (en) | 1995-12-22 | 1996-12-20 | Isocyanate-terminated prepolymers or quasiprepolymers, polyurethane elastomers, and methods of increasing the physical properties of chain-extended polyurethane elastomers |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5648447A (enExample) |
| EP (1) | EP0868455B1 (enExample) |
| JP (1) | JP2001500167A (enExample) |
| CN (1) | CN1112392C (enExample) |
| AR (1) | AR005180A1 (enExample) |
| AU (1) | AU1144897A (enExample) |
| BR (1) | BR9612112A (enExample) |
| CA (1) | CA2241268A1 (enExample) |
| DE (1) | DE69608309T2 (enExample) |
| ES (1) | ES2146033T3 (enExample) |
| TW (1) | TW492984B (enExample) |
| WO (1) | WO1997023531A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI480123B (zh) * | 2009-07-24 | 2015-04-11 | 羅門哈斯電子材料Ｃｍｐ控股公司 | 多功能研磨墊 |
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|---|---|---|---|---|
| US5670601A (en) * | 1995-06-15 | 1997-09-23 | Arco Chemical Technology, L.P. | Polyurethane elastomers having improved green strength and demold time and polyoxyalkylene polyols suitable for their preparation |
| US5700847A (en) * | 1995-12-04 | 1997-12-23 | Arco Chemical Technology, L.P. | Molded polyurethane foam with enhanced physical properties |
| US6258917B1 (en) * | 1996-05-21 | 2001-07-10 | Simula, Inc. | Extrudable thermoplastic elastomeric urea-extended polyurethane |
| US5856372A (en) * | 1996-05-23 | 1999-01-05 | Arco Chemical Technology, L.P. | Microcellular elastomers with improved processability and properties |
| US6040413A (en) * | 1996-07-10 | 2000-03-21 | Basf Corporation | Composition of polytetramethylene ether glycols and polyoxy alkylene polyether polyols having a low degree of unsaturation |
| US5723563A (en) * | 1996-10-11 | 1998-03-03 | Arco Chemical Technology, L.P. | Spandex elastomers |
| US5708118A (en) * | 1996-10-11 | 1998-01-13 | Arco Chemical Technology, L.P. | Spandex elastomers |
| CN1123587C (zh) | 1997-12-05 | 2003-10-08 | 拜尔公司 | 聚氨酯和聚氨酯/脲热固化和湿固化的弹性体 |
| KR100637640B1 (ko) * | 1999-03-17 | 2006-10-23 | 아사히 가라스 가부시키가이샤 | 폴리우레탄계/폴리우레탄우레아계 수지 및 그의 제조 방법 |
| DE19918726C2 (de) | 1999-04-24 | 2002-04-11 | Bayer Ag | Offenzellige Polyurethanhartschaumstoffe |
| US6344494B1 (en) | 2000-05-24 | 2002-02-05 | Basf Corporation | Use of low unsaturated polyether polyols in slabstock foam applications |
| US6201035B1 (en) | 2000-05-24 | 2001-03-13 | Basf Corporation | Use of low unsaturated polyether polyols in high resilience slabstock foam applications |
| IT1318961B1 (it) | 2000-10-03 | 2003-09-19 | Erminio Rossini S P A Ora Ross | Manica perfezionata per cilindro sussidiario di una macchina da stampaindiretta o "offset". |
| CN1639221A (zh) * | 2002-03-07 | 2005-07-13 | 旭硝子株式会社 | 热固化性聚氨酯弹性体组合物、聚氨酯弹性体及其制造方法 |
| US6824703B2 (en) * | 2002-03-08 | 2004-11-30 | Bayer Materialscience Llc | Polyurethane elastomers having improved physical properties and a process for the production thereof |
| US7511111B2 (en) * | 2002-03-08 | 2009-03-31 | Bayer Materialscience Llc | Polyurethane elastomers having improved physical properties and a process for the production thereof |
| US6903179B2 (en) * | 2002-05-30 | 2005-06-07 | Bayer Materialscience Llc | Polyurethane/ureas useful for the production of spandex and a process for their production |
| JP4605012B2 (ja) * | 2003-07-24 | 2011-01-05 | 旭硝子株式会社 | ポリウレタン樹脂およびその製造方法 |
| US20050037194A1 (en) * | 2003-08-15 | 2005-02-17 | Kimberly-Clark Worldwide, Inc. | Thermoplastic polymers with thermally reversible and non-reversible linkages, and articles using same |
| DE102004015985A1 (de) * | 2004-04-01 | 2005-10-20 | Bayer Materialscience Ag | Verfärbungsstabile Polyetherallophanate |
| WO2006047434A1 (en) * | 2004-10-25 | 2006-05-04 | Dow Global Technologies, Inc. | Prepolymers made from hydroxmethyl-containing polyester polyols derived from fatty acids |
| DE102005011784A1 (de) * | 2005-03-11 | 2006-09-14 | Basf Ag | Prepolymere und daraus hergestellte zellige Polyisocyanat-Polyadditionsprodukte |
| 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 |
| EP2132250A1 (en) * | 2007-03-29 | 2009-12-16 | Lubrizol Advanced Materials, Inc. | Thermoplastic polyurethane prepared using a mixture of polyester diol and poly ( propylene oxide) diol |
| US20090193991A1 (en) | 2008-02-04 | 2009-08-06 | Felice Rossini | Blanket sleeve and cylinder and method of making same |
| US20100307356A1 (en) * | 2008-02-04 | 2010-12-09 | Felice Rossini | Bridged sleeve/cylinder and method of making same for web offset printing machines |
| CN101857670B (zh) * | 2009-04-10 | 2013-04-03 | 拜耳材料科技(中国)有限公司 | 聚氨酯微孔弹性体及其制备方法和应用 |
| JP6098379B2 (ja) * | 2013-06-05 | 2017-03-22 | 富士ゼロックス株式会社 | クリーニングブレード、クリーニング装置、プロセスカートリッジ、および画像形成装置 |
| KR102243100B1 (ko) | 2013-08-26 | 2021-04-22 | 헌츠만 페트로케미칼 엘엘씨 | 아민 촉매 내의 알데하이드의 감소 |
| JP6509236B2 (ja) | 2013-10-01 | 2019-05-08 | ハンツマン ペトロケミカル エルエルシーＨｕｎｔｓｍａｎ Ｐｅｔｒｏｃｈｅｍｉｃａｌ ＬＬＣ | アミン触媒中のアルデヒドの減少 |
| EP3052568B1 (en) | 2013-10-04 | 2020-05-06 | Luna Innovations Incorporated | Fluid resistant, high performance reactive hot melt sealant and/or adhesive compositions |
| EP3077439B1 (en) | 2013-12-02 | 2020-04-29 | Dow Global Technologies LLC | Storage stable polyol composition for polyurethane elastomers |
| WO2015200408A1 (en) | 2014-06-27 | 2015-12-30 | Huntsman Petrochemical Llc | Pyrrolidine-based catalysts for use in polyurethane materials |
| US10766994B2 (en) | 2014-12-31 | 2020-09-08 | Huntsman Petrochemical Llc | Reduction of aldehydes in amine catalysts |
| WO2019209348A1 (en) | 2018-04-28 | 2019-10-31 | Liang Wang | Polyurethane elastomer with high ultimate elongation |
| WO2021194766A1 (en) | 2020-03-27 | 2021-09-30 | Huntsman Petrochemical Llc | Acid-blocked alkylaminopyridine catalysts for polyurethane foam |
| BR112023002689A2 (pt) | 2020-08-14 | 2023-03-14 | Huntsman Int Llc | Formulação de poliuretano, método para produzir um material de poliuretano, e, material de poliuretano |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980606A (en) * | 1975-02-24 | 1976-09-14 | The Firestone Tire & Rubber Company | Polyurethane elastomers having prolonged flex life and tires made therefrom |
| HU207744B (en) * | 1989-03-17 | 1993-05-28 | Lonza Ag | Chain-extending composition for producing moulded polyurethane |
| JP2619109B2 (ja) * | 1989-05-09 | 1997-06-11 | 旭硝子株式会社 | 柔軟性にすぐれたポリウレタン系硬化性組成物 |
| US5136010A (en) * | 1990-09-28 | 1992-08-04 | Olin Corporation | Polyurethane elastomers and polyurea elastomers made using high functionality, low unsaturation level polyols prepared with double metal cyanide catalysts |
| US5185420A (en) * | 1990-11-02 | 1993-02-09 | Olin Corporation | Thermoplastic polyurethane elastomers and polyurea elastomers made using low unsaturation level polyols prepared with double metal cyanide catalysts |
| CN1076933A (zh) * | 1992-03-31 | 1993-10-06 | 宋兆生 | 高回弹低密度模塑聚氨酯泡沫的制备方法 |
| EP0643733A4 (en) * | 1992-06-04 | 1996-04-03 | Olin Corp | HARD THERMOPLASTIC POLYURETHANE ELASTOMERS. |
| CA2095876A1 (en) * | 1992-06-05 | 1993-12-06 | Nigel Barksby | Isocyante-terminated prepolymers derived from polyether polyol mixtures having low monol content and their use in polyurethanes |
| US5470813A (en) * | 1993-11-23 | 1995-11-28 | Arco Chemical Technology, L.P. | Double metal cyanide complex catalysts |
-
1995
- 1995-12-22 US US08/577,959 patent/US5648447A/en not_active Expired - Fee Related
-
1996
- 1996-12-04 JP JP09523661A patent/JP2001500167A/ja not_active Ceased
- 1996-12-04 EP EP96942861A patent/EP0868455B1/en not_active Expired - Lifetime
- 1996-12-04 ES ES96942861T patent/ES2146033T3/es not_active Expired - Lifetime
- 1996-12-04 CA CA002241268A patent/CA2241268A1/en not_active Abandoned
- 1996-12-04 CN CN96199179A patent/CN1112392C/zh not_active Expired - Fee Related
- 1996-12-04 BR BR9612112A patent/BR9612112A/pt not_active Application Discontinuation
- 1996-12-04 DE DE69608309T patent/DE69608309T2/de not_active Expired - Fee Related
- 1996-12-04 WO PCT/US1996/019235 patent/WO1997023531A1/en not_active Ceased
- 1996-12-04 AU AU11448/97A patent/AU1144897A/en not_active Abandoned
- 1996-12-20 TW TW085115787A patent/TW492984B/zh not_active IP Right Cessation
- 1996-12-20 AR ARP960105825A patent/AR005180A1/es unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI480123B (zh) * | 2009-07-24 | 2015-04-11 | 羅門哈斯電子材料Ｃｍｐ控股公司 | 多功能研磨墊 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001500167A (ja) | 2001-01-09 |
| ES2146033T3 (es) | 2000-07-16 |
| AR005180A1 (es) | 1999-04-14 |
| AU1144897A (en) | 1997-07-17 |
| CA2241268A1 (en) | 1997-07-03 |
| DE69608309D1 (de) | 2000-06-15 |
| US5648447A (en) | 1997-07-15 |
| EP0868455B1 (en) | 2000-05-10 |
| CN1112392C (zh) | 2003-06-25 |
| DE69608309T2 (de) | 2000-10-19 |
| EP0868455A1 (en) | 1998-10-07 |
| WO1997023531A1 (en) | 1997-07-03 |
| BR9612112A (pt) | 1999-06-15 |
| CN1205713A (zh) | 1999-01-20 |
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| GD4A | Issue of patent certificate for granted invention patent | ||
| MM4A | Annulment or lapse of patent due to non-payment of fees |