CS126791A2 - Microporous polyurethane polymers prepared from isocyanate terminated poly (oxytetramethylene) glycol prepolymers and method of their production - Google Patents

Microporous polyurethane polymers prepared from isocyanate terminated poly (oxytetramethylene) glycol prepolymers and method of their production Download PDF

Info

Publication number: CS126791A2
Authority: CS; Czechoslovakia
Prior art keywords: weight; isocyanate; mixture; present; equivalent
Prior art date: 1990-05-04

Application number

CS911267A

Other languages

Czech (cs)

English (en)

Inventor

Stefano Mussini

Original Assignee

Dow Italia

Priority date (The priority date 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 date listed.)

1990-05-04

Filing date

1991-05-02

Publication date

1991-12-17

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=11164746&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CS126791(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1991-05-02 Application filed by Dow Italia filed Critical Dow Italia

1991-12-17 Publication of CS126791A2 publication Critical patent/CS126791A2/cs

Links

229920000642 polymer Polymers 0.000 title claims description 66
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 50
238000000034 method Methods 0.000 title claims description 40
-1 poly (oxytetramethylene) Polymers 0.000 title claims description 31
239000004814 polyurethane Substances 0.000 title claims description 27
229920002635 polyurethane Polymers 0.000 title claims description 27
239000012948 isocyanate Substances 0.000 title claims description 25
150000002513 isocyanates Chemical class 0.000 title claims description 23
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 21
238000004519 manufacturing process Methods 0.000 title claims description 4
239000000203 mixture Substances 0.000 claims description 61
229920005862 polyol Polymers 0.000 claims description 35
150000003077 polyols Chemical class 0.000 claims description 35
239000005056 polyisocyanate Substances 0.000 claims description 31
229920001228 polyisocyanate Polymers 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
239000004604 Blowing Agent Substances 0.000 claims description 20
239000004721 Polyphenylene oxide Substances 0.000 claims description 18
229920000570 polyether Polymers 0.000 claims description 18
239000004970 Chain extender Substances 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 12
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 claims description 11
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 4
150000001718 carbodiimides Chemical class 0.000 claims description 4
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 3
OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 claims description 3
229920006389 polyphenyl polymer Polymers 0.000 claims description 3
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
239000013543 active substance Substances 0.000 claims 1
YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 claims 1
229920001223 polyethylene glycol Polymers 0.000 claims 1
230000001172 regenerating effect Effects 0.000 claims 1
238000002360 preparation method Methods 0.000 description 15
230000000704 physical effect Effects 0.000 description 12
239000003054 catalyst Substances 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
150000002009 diols Chemical class 0.000 description 10
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 10
238000009472 formulation Methods 0.000 description 7
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
229920005906 polyester polyol Polymers 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 6
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
150000002334 glycols Chemical class 0.000 description 5
WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000003999 initiator Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229920001730 Moisture cure polyurethane Polymers 0.000 description 3
229920013701 VORANOL™ Polymers 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
230000009477 glass transition Effects 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
238000002156 mixing Methods 0.000 description 3
125000002524 organometallic group Chemical group 0.000 description 3
229940029284 trichlorofluoromethane Drugs 0.000 description 3
ZXUJWPHOPHHZLR-UHFFFAOYSA-N 1,1,1-trichloro-2-fluoroethane Chemical compound FCC(Cl)(Cl)Cl ZXUJWPHOPHHZLR-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
238000005452 bending Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000012975 dibutyltin dilaurate Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
150000002894 organic compounds Chemical group 0.000 description 2
239000000049 pigment Substances 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229920000098 polyolefin Polymers 0.000 description 2
235000013772 propylene glycol Nutrition 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
150000004072 triols Chemical class 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
FQAMAOOEZDRHHB-UHFFFAOYSA-N 1,2,2-trichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)C(Cl)Cl FQAMAOOEZDRHHB-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-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
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
LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 1
PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
IAXFZZHBFXRZMT-UHFFFAOYSA-N 2-[3-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=CC(OCCO)=C1 IAXFZZHBFXRZMT-UHFFFAOYSA-N 0.000 description 1
SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
241001342895 Chorus Species 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
101150082137 Mtrr gene Proteins 0.000 description 1
AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
241000207836 Olea <angiosperm> Species 0.000 description 1
ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
229920002396 Polyurea Polymers 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 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
238000005299 abrasion Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000005263 alkylenediamine group Chemical group 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000002216 antistatic agent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
VTZRJDPNHRTRSV-UHFFFAOYSA-N benzene-1,4-diol;propane-1,2,3-triol Chemical class OCC(O)CO.OC1=CC=C(O)C=C1 VTZRJDPNHRTRSV-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
FCQAMVZGVMHDFT-UHFFFAOYSA-N butane-1,4-diol;propane-1,2,3-triol Chemical compound OCCCCO.OCC(O)CO FCQAMVZGVMHDFT-UHFFFAOYSA-N 0.000 description 1
GZSSFSARCMSPPW-UHFFFAOYSA-N butane-2,2-diol Chemical compound CCC(C)(O)O GZSSFSARCMSPPW-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
238000000280 densification Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
229940042935 dichlorodifluoromethane Drugs 0.000 description 1
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
229940099364 dichlorofluoromethane Drugs 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000000835 fiber Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
HOVAGTYPODGVJG-ZFYZTMLRSA-N methyl alpha-D-glucopyranoside Chemical compound CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-ZFYZTMLRSA-N 0.000 description 1
CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
229940073584 methylene chloride Drugs 0.000 description 1
239000004005 microsphere Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
229920003225 polyurethane elastomer Polymers 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—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
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- 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
- C08G2110/0058—≥50 and <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
- C08G2110/0041—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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2380/00—Tyres
- 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
- C08G2410/00—Soles

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)
Compositions Of Macromolecular Compounds (AREA)
Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

CS911267A 1990-05-04 1991-05-02 Microporous polyurethane polymers prepared from isocyanate terminated poly (oxytetramethylene) glycol prepolymers and method of their production CS126791A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT20205A IT1240635B (it)	1990-05-04	1990-05-04	Polimeri poliuretanici microcellulari preparati da tre polimeri di poli (tetrametilen) glicoli con gruppi isocianato terminali

Publications (1)

Publication Number	Publication Date
CS126791A2 true CS126791A2 (en)	1991-12-17

Family

ID=11164746

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS911267A CS126791A2 (en)	1990-05-04	1991-05-02	Microporous polyurethane polymers prepared from isocyanate terminated poly (oxytetramethylene) glycol prepolymers and method of their production

Country Status (17)

Country	Link
EP (1)	EP0527174B1 (pl)
JP (1)	JPH05506688A (pl)
AU (1)	AU641768B2 (pl)
BR (1)	BR9106455A (pl)
CA (1)	CA2080597A1 (pl)
CS (1)	CS126791A2 (pl)
CY (1)	CY1856A (pl)
DE (1)	DE69104197T2 (pl)
ES (1)	ES2060383T3 (pl)
HK (1)	HK14795A (pl)
IE (1)	IE911510A1 (pl)
IT (1)	IT1240635B (pl)
PL (1)	PL169691B1 (pl)
PT (1)	PT97542B (pl)
WO (1)	WO1991017197A1 (pl)
YU (1)	YU77791A (pl)
ZA (1)	ZA913351B (pl)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4980445A (en) *	1989-01-17	1990-12-25	The Dow Chemical Company	Thermoplastic polyurethanes
US5246977A (en) *	1990-05-04	1993-09-21	The Dow Chemical Company	Microcellular polyurethane polymers prepared from isocyanate-terminated poly(oxytetramethylene) glycol prepolymers
US5491175A (en) *	1992-04-10	1996-02-13	The Dow Chemical Company	Polyurethane foam molding
US5234961A (en) *	1992-12-07	1993-08-10	Basf Corporation	Polyurethane water-blown integral skin system produced with a polyterahydrofuran prepolymer
CA2139654A1 (en) *	1993-05-12	1994-11-24	Yoshiaki Miyazaki	Molded polyurethane foams
GB9420107D0 (en) *	1994-10-05	1994-11-16	Kemira Coatings Limted	Polyurethane composition
US5618967A (en) *	1995-10-30	1997-04-08	Basf Corporation	Isocyanate composition
EP0771829A1 (en)	1995-10-30	1997-05-07	Basf Corporation	Process of making an integral skin polyurethane article
US5672632A (en) *	1995-10-30	1997-09-30	Basf Corporation	Integral skin polyurethane molded articles
US5624966A (en) *	1995-10-30	1997-04-29	Basf Corporation	Process of making an integral skin polyurethane article
US5658959A (en) *	1995-10-30	1997-08-19	Basf Corporation	Water blown integral skin polyurethane composition
MY128201A (en) *	1998-06-22	2007-01-31	Kao Corp	Process for preparing polyurethane foam.
DE102005011784A1 (de)	2005-03-11	2006-09-14	Basf Ag	Prepolymere und daraus hergestellte zellige Polyisocyanat-Polyadditionsprodukte
JP6759648B2 (ja) *	2015-04-15	2020-09-23	東ソー株式会社	ポリウレタンインテグラルスキンフォーム及びその製造方法
AU2018227869B2 (en) *	2017-03-03	2023-02-09	Dow Global Technologies Llc	Low density polyurethane elastomer foam with high ball rebound
JP2023118223A (ja) *	2022-02-15	2023-08-25	株式会社イノアックコーポレーション	タイヤ用充填材及びタイヤ用充填材の製造方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH601369A5 (en) *	1974-02-26	1978-07-14	Shell Int Research	Thermoplastic and elastomeric polyurethane products
JPS5951576B2 (ja) *	1979-08-03	1984-12-14	三井日曹ウレタン株式会社	ポリウレタンエラストマ−と金属との接着方法
DE3138422A1 (de) *	1981-09-26	1983-04-14	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von zelligen polyurethan-elastomeren auf basis von 4,4'-diisocyanato-diphenylethan-1,2
US4994502A (en) *	1987-07-01	1991-02-19	Basf Corporation	Process for the preparation of integral skin polyurethane steering wheels
DE3729822A1 (de) *	1987-09-05	1989-03-23	Continental Ag	Polyurethan-rotationskoerper und verfahren zu seiner herstellung
US5114989A (en) *	1990-11-13	1992-05-19	The Dow Chemical Company	Isocyanate-terminated prepolymer and polyurethane foam prepared therefrom

1990
- 1990-05-04 IT IT20205A patent/IT1240635B/it active IP Right Grant
1991
- 1991-04-22 CY CY185691A patent/CY1856A/xx unknown
- 1991-04-22 ES ES91908610T patent/ES2060383T3/es not_active Expired - Lifetime
- 1991-04-22 CA CA002080597A patent/CA2080597A1/en not_active Abandoned
- 1991-04-22 AU AU77788/91A patent/AU641768B2/en not_active Ceased
- 1991-04-22 PL PL91296705A patent/PL169691B1/pl unknown
- 1991-04-22 JP JP91508146A patent/JPH05506688A/ja active Pending
- 1991-04-22 DE DE69104197T patent/DE69104197T2/de not_active Expired - Lifetime
- 1991-04-22 BR BR919106455A patent/BR9106455A/pt not_active IP Right Cessation
- 1991-04-22 WO PCT/EP1991/000772 patent/WO1991017197A1/en not_active Ceased
- 1991-04-22 EP EP91908610A patent/EP0527174B1/en not_active Expired - Lifetime
- 1991-04-29 YU YU77791A patent/YU77791A/sh unknown
- 1991-05-02 CS CS911267A patent/CS126791A2/cs unknown
- 1991-05-02 PT PT97542A patent/PT97542B/pt not_active IP Right Cessation
- 1991-05-03 IE IE151091A patent/IE911510A1/en unknown
- 1991-05-03 ZA ZA913351A patent/ZA913351B/xx unknown
1995
- 1995-02-06 HK HK14795A patent/HK14795A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE69104197T2 (de)	1995-01-19
EP0527174B1 (en)	1994-09-21
HK14795A (en)	1995-02-10
PT97542A (pt)	1992-01-31
EP0527174A1 (en)	1993-02-17
ES2060383T3 (es)	1994-11-16
CY1856A (en)	1991-04-22
IE911510A1 (en)	1991-11-06
BR9106455A (pt)	1993-05-25
IT9020205A1 (it)	1991-11-04
DE69104197D1 (de)	1994-10-27
PT97542B (pt)	1999-02-26
IT9020205A0 (it)	1990-05-04
WO1991017197A1 (en)	1991-11-14
AU641768B2 (en)	1993-09-30
PL169691B1 (pl)	1996-08-30
ZA913351B (en)	1993-01-27
JPH05506688A (ja)	1993-09-30
CA2080597A1 (en)	1991-11-05
AU7778891A (en)	1991-11-27
IT1240635B (it)	1993-12-17
YU77791A (sh)	1994-01-20

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