BRPI0616666B1 - processo para a preparação de um material de poliisocianurato poliuretano elastomérico, e, material - Google Patents
processo para a preparação de um material de poliisocianurato poliuretano elastomérico, e, material Download PDFInfo
- Publication number
- BRPI0616666B1 BRPI0616666B1 BRPI0616666A BRPI0616666A BRPI0616666B1 BR PI0616666 B1 BRPI0616666 B1 BR PI0616666B1 BR PI0616666 A BRPI0616666 A BR PI0616666A BR PI0616666 A BRPI0616666 A BR PI0616666A BR PI0616666 B1 BRPI0616666 B1 BR PI0616666B1
- Authority
- BR
- Brazil
- Prior art keywords
- polyisocyanate
- weight
- isocyanate
- polyol
- amount
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 30
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 24
- 239000004814 polyurethane Substances 0.000 title claims abstract description 24
- 239000011495 polyisocyanurate Substances 0.000 title claims abstract description 15
- 229920000582 polyisocyanurate Polymers 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims description 9
- 229920005862 polyol Polymers 0.000 claims abstract description 68
- 150000003077 polyols Chemical class 0.000 claims abstract description 67
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 64
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 64
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 239000012948 isocyanate Substances 0.000 claims abstract description 25
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 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 abstract description 17
- 229920000570 polyether Polymers 0.000 claims abstract description 16
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 15
- 125000006353 oxyethylene group Chemical group 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 238000005829 trimerization reaction Methods 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- -1 oxyethylene polyol Chemical class 0.000 description 36
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229920000768 polyamine Chemical class 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000004970 Chain extender Substances 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000004971 Cross linker Substances 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- PGYPOBZJRVSMDS-UHFFFAOYSA-N loperamide hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 PGYPOBZJRVSMDS-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 238000010107 reaction injection moulding Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004604 Blowing Agent Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 229910002092 carbon dioxide Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 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
- 150000002009 diols Chemical class 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920006295 polythiol Polymers 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 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 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N 2-methylpropane-1,2-diol Chemical compound CC(C)(O)CO BTVWZWFKMIUSGS-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
- YSWBFLWKAIRHEI-UHFFFAOYSA-N 4,5-dimethyl-1h-imidazole Chemical compound CC=1N=CNC=1C YSWBFLWKAIRHEI-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 244000198134 Agave sisalana Species 0.000 description 1
- 239000004156 Azodicarbonamide Substances 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920000103 Expandable microsphere Polymers 0.000 description 1
- 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 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- 229920000271 Kevlar® Polymers 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-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
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 1
- 235000019399 azodicarbonamide Nutrition 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001569 carbon dioxide Chemical group 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- LRQJDHFPKVRGRT-UHFFFAOYSA-N cyclohexane;5-methyl-2-propan-2-ylcyclohexan-1-ol Chemical compound C1CCCCC1.CC(C)C1CCC(C)CC1O.CC(C)C1CCC(C)CC1O LRQJDHFPKVRGRT-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000013536 elastomeric material Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 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
- 150000002431 hydrogen Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012802 nanoclay Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- 238000009736 wetting Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-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
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
-
- 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
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
-
- 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
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
- C08G18/092—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to isocyanurate groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP05109528.9 | 2005-10-13 | ||
| EP05109528 | 2005-10-13 | ||
| PCT/EP2006/066874 WO2007042407A1 (en) | 2005-10-13 | 2006-09-29 | Process for preparing a polyisocyanurate polyurethane material |
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| BRPI0616666A2 BRPI0616666A2 (pt) | 2012-12-25 |
| BRPI0616666B1 true BRPI0616666B1 (pt) | 2017-06-06 |
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| BRPI0616666A BRPI0616666B1 (pt) | 2005-10-13 | 2006-09-29 | processo para a preparação de um material de poliisocianurato poliuretano elastomérico, e, material |
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| EP (1) | EP1940898B1 (enExample) |
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| AU (1) | AU2006301363B2 (enExample) |
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| DE (1) | DE602006018974D1 (enExample) |
| RU (1) | RU2428436C2 (enExample) |
| WO (1) | WO2007042407A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2372358C2 (ru) * | 2003-06-12 | 2009-11-10 | Хантсмэн Интернэшнл Ллс | Способ получения полиизоциануратполиуретанового материала |
| AU2006301367B2 (en) * | 2005-10-13 | 2012-02-02 | Huntsman International Llc | Process for preparing polyisocyanurate polyurethane material |
| JP5159640B2 (ja) * | 2006-02-21 | 2013-03-06 | ハンツマン・インターナショナル・エルエルシー | ポリイソシアヌレート複合物の製造方法 |
| MX2008016002A (es) | 2006-06-14 | 2009-01-16 | Huntsman Int Llc | Panel compuesto. |
| EP2072549A1 (en) * | 2007-12-19 | 2009-06-24 | Huntsman International Llc | Novel composition from a polyisocyanate and a polyether monoamine |
| PL2245081T3 (pl) * | 2008-02-14 | 2016-02-29 | Huntsman Int Llc | Materiały elastomerowe o wysokiej zawartości bloku sztywnego i sposób ich wytwarzania |
| DE102008036995A1 (de) * | 2008-08-07 | 2010-02-11 | Bayer Materialscience Ag | Kunststoffformteile aus Polyurethan und deren Verwendung |
| CA2732421C (en) * | 2008-08-28 | 2016-05-17 | Huntsman International Llc | Mixture obtained by reacting polyol and anhydride and its use in polyisocyanates for making polyisocyanurates |
| US8901187B1 (en) | 2008-12-19 | 2014-12-02 | Hickory Springs Manufacturing Company | High resilience flexible polyurethane foam using MDI |
| US8906975B1 (en) | 2009-02-09 | 2014-12-09 | Hickory Springs Manufacturing Company | Conventional flexible polyurethane foam using MDI |
| US8962142B2 (en) | 2010-07-08 | 2015-02-24 | Huntsman International Llc | Polyisocyanate-based anti-corrosion coating |
| WO2012062801A1 (en) | 2010-11-09 | 2012-05-18 | Rockwool International A/S | Mineral fibre product having reduced thermal conductivity |
| WO2012062796A1 (en) | 2010-11-09 | 2012-05-18 | Rockwool International A/S | Method for manufacturing an aerogel-containing composite and composite produced by said method |
| EP2639249A1 (en) * | 2011-12-06 | 2013-09-18 | Basf Se | Abrasion-resistant polyurethane coating |
| CN104093759B (zh) | 2012-02-08 | 2016-09-21 | 科思创德国股份有限公司 | 聚氨酯-聚异氰脲酸酯-硬质泡沫材料的制备方法 |
| EP2687551A1 (en) * | 2012-07-17 | 2014-01-22 | Huntsman International Llc | Intermediate polyisocyanurate comprising materials |
| CN105189595B (zh) * | 2013-03-28 | 2018-03-02 | 陶氏环球技术有限责任公司 | 用于制备氨基甲酸酯‑异氰脲酸酯的方法 |
| US10294391B2 (en) | 2013-07-11 | 2019-05-21 | Dow Global Technologies Llc | Process for making urethane-isocyanurates |
| US20150315329A1 (en) * | 2014-04-29 | 2015-11-05 | MCPU Polymer Engineering, LLC | Method for preparing novel natural oil based high temperature isocyanurate containing polyurethane thermosetting resins |
| WO2016065248A1 (en) | 2014-10-23 | 2016-04-28 | Complete Genomics, Inc. | Signal confinement sequencing (scs) and nucleotide analogues for signal confinement sequencing |
| MX2016005815A (es) * | 2015-05-13 | 2016-11-14 | Ford Global Tech Llc | Compuesto hibrido con uso de geometrias de moldura asistida por gas. |
| EP3147303A1 (en) * | 2015-09-25 | 2017-03-29 | Ernesto Monton Martin | Solid surface product comprising aliphatic isocyanate and process for manufacturing thereof |
| JP2019536849A (ja) * | 2016-10-18 | 2019-12-19 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | ブロックトポリイソシアネートの触媒架橋によるプラスチックの製造 |
| CN108084394B (zh) * | 2017-12-25 | 2020-09-29 | 青岛科技大学 | 一种形状记忆硬质聚氨酯发泡医用夹板材料及其制备方法 |
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| US3940517A (en) * | 1973-01-11 | 1976-02-24 | The Celotex Corporation | Polyisocyanurate foam, catalyst composition and process for producing such |
| DE2607380C3 (de) * | 1976-02-24 | 1981-07-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von warmformbaren Polyisocyanuratschaumstoffen |
| US4126742A (en) * | 1978-05-15 | 1978-11-21 | The Upjohn Company | High-modulus polyisocyanurate elastomers |
| US4126741A (en) * | 1978-05-15 | 1978-11-21 | The Upjohn Company | High-modulus polyisocyanurate elastomers |
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| US4424288A (en) * | 1981-12-24 | 1984-01-03 | Basf Wyandotte Corporation | Carbodiimide-modified polymethylene polyphenylene polyisocyanates for use in the preparation of polyisocyanurate-polyurethane foams |
| US4661533A (en) * | 1985-10-28 | 1987-04-28 | The Dow Chemical Company | Rigid polyurethane modified polyisocyanurate containing fly ash as an inorganic filler |
| US4900776A (en) * | 1988-12-01 | 1990-02-13 | Georgia-Pacific Resins, Inc. | Potassium catalyst system for preparing polyurethane based plywood-patch compositions |
| US5137929A (en) * | 1991-06-21 | 1992-08-11 | Allied-Signal Inc. | Additives which stabilize hydrohalocarbon blowing agent in polyurethane and polyisocyanurate foam formulations during polymerization |
| US5232957A (en) * | 1992-09-11 | 1993-08-03 | Davidson Textron Inc. | RIM molded energy absorbing polyurethane foam |
| US5773483A (en) * | 1993-04-13 | 1998-06-30 | Imperial Chemical Industries Plc | Process for preparing a flexible foam |
| US5556934A (en) * | 1993-09-03 | 1996-09-17 | H. B. Fuller Licensing & Financing Inc. | Isocyanurate embedment compound |
| US5346928A (en) * | 1993-09-09 | 1994-09-13 | Imperial Chemical Industries Plc | Rigid polyurethane foams |
| US5591779A (en) * | 1994-11-22 | 1997-01-07 | Imperial Chemical Industries Plc | Process for making flexible foams |
| BR9608507A (pt) * | 1995-05-12 | 1999-06-08 | Ici Plc | Processo para a preparação de espuma rigida de poliuretano processo para preparar uma espuma flexível de poliuretano sistema de reação e espuma flexível de poliuretano |
| WO1998000450A1 (en) * | 1996-06-27 | 1998-01-08 | Imperial Chemical Industries Plc | Microcellular elastomeric polyurethane foams |
| AU1670399A (en) * | 1997-12-05 | 1999-06-28 | Bayer Aktiengesellschaft | Polyurethane and polyurethane/urea heat-cured and moisture-cured elastomers withimproved physical properties |
| DE19838167A1 (de) * | 1998-08-21 | 2000-02-24 | Basf Ag | Mischung enthaltend Isocyanate sowie organische und/oder anorganische Säureanhydride |
| CA2359560C (en) * | 1998-11-16 | 2009-02-03 | Huntsman International Llc | Polyisocyanurate compositions and composites |
| DE19918726C2 (de) * | 1999-04-24 | 2002-04-11 | Bayer Ag | Offenzellige Polyurethanhartschaumstoffe |
| EP1167414A1 (en) * | 2000-06-29 | 2002-01-02 | Huntsman International Llc | Process for making rigid polyurethane foams having high adhesion |
| EP1172387A1 (en) * | 2000-07-14 | 2002-01-16 | Huntsman International Llc | Process for preparing an elastomer |
| US6418261B1 (en) * | 2000-07-24 | 2002-07-09 | Corning Incorporated | Method to reduce warpage and polarization sensitivity of planar devices |
| EP1178061A1 (en) * | 2000-08-01 | 2002-02-06 | Huntsman International Llc | Process for preparing a polyurethane material |
| EP1178063A1 (en) * | 2000-08-01 | 2002-02-06 | Huntsman International Llc | Process for preparing a polyurethane material |
| JP4472856B2 (ja) * | 2000-09-19 | 2010-06-02 | 有限会社サン・イースト・リサーチ | 親水性連続微細気泡ポリイソシアヌレートフォームの製造方法並びに親水性連続微細気泡ポリイソシアヌレートフォーム |
| US6729045B2 (en) * | 2002-10-02 | 2004-05-04 | Dale F. Isackson | Tap device for clogging shoes |
| US20040069971A1 (en) * | 2002-10-15 | 2004-04-15 | Witteveen Martijn M. | Polyol compositions and rigid polyisocyanurate foams prepared therefrom |
| US20040249078A1 (en) * | 2003-06-04 | 2004-12-09 | Honeywell International, Inc. | Foam catalyst systems |
| RU2372358C2 (ru) * | 2003-06-12 | 2009-11-10 | Хантсмэн Интернэшнл Ллс | Способ получения полиизоциануратполиуретанового материала |
| US7763341B2 (en) * | 2004-01-23 | 2010-07-27 | Century-Board Usa, Llc | Filled polymer composite and synthetic building material compositions |
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2006
- 2006-09-29 JP JP2008534978A patent/JP5044560B2/ja not_active Expired - Fee Related
- 2006-09-29 US US12/089,822 patent/US20080227929A1/en not_active Abandoned
- 2006-09-29 EP EP06793902A patent/EP1940898B1/en not_active Not-in-force
- 2006-09-29 RU RU2008118508/04A patent/RU2428436C2/ru active
- 2006-09-29 WO PCT/EP2006/066874 patent/WO2007042407A1/en not_active Ceased
- 2006-09-29 AT AT06793902T patent/ATE491734T1/de not_active IP Right Cessation
- 2006-09-29 DE DE602006018974T patent/DE602006018974D1/de active Active
- 2006-09-29 CA CA2620757A patent/CA2620757C/en active Active
- 2006-09-29 AU AU2006301363A patent/AU2006301363B2/en not_active Ceased
- 2006-09-29 BR BRPI0616666A patent/BRPI0616666B1/pt not_active IP Right Cessation
- 2006-09-29 KR KR1020087008756A patent/KR101288266B1/ko not_active Expired - Fee Related
- 2006-09-29 CN CN2006800376013A patent/CN101283011B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2009511684A (ja) | 2009-03-19 |
| KR20080057272A (ko) | 2008-06-24 |
| CA2620757C (en) | 2013-11-12 |
| JP5044560B2 (ja) | 2012-10-10 |
| AU2006301363A1 (en) | 2007-04-19 |
| EP1940898A1 (en) | 2008-07-09 |
| CN101283011A (zh) | 2008-10-08 |
| RU2008118508A (ru) | 2009-11-20 |
| AU2006301363B2 (en) | 2012-02-16 |
| EP1940898B1 (en) | 2010-12-15 |
| CN101283011B (zh) | 2013-04-10 |
| CA2620757A1 (en) | 2007-04-19 |
| ATE491734T1 (de) | 2011-01-15 |
| BRPI0616666A2 (pt) | 2012-12-25 |
| US20080227929A1 (en) | 2008-09-18 |
| RU2428436C2 (ru) | 2011-09-10 |
| DE602006018974D1 (de) | 2011-01-27 |
| WO2007042407A1 (en) | 2007-04-19 |
| KR101288266B1 (ko) | 2013-07-29 |
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