ZA200104555B - Thermosetting poly urethane/urea-forming compositions. - Google Patents
Thermosetting poly urethane/urea-forming compositions. Download PDFInfo
- Publication number
- ZA200104555B ZA200104555B ZA200104555A ZA200104555A ZA200104555B ZA 200104555 B ZA200104555 B ZA 200104555B ZA 200104555 A ZA200104555 A ZA 200104555A ZA 200104555 A ZA200104555 A ZA 200104555A ZA 200104555 B ZA200104555 B ZA 200104555B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- phosphate
- unsubstituted
- independently
- substituted
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 29
- 239000004814 polyurethane Substances 0.000 title claims abstract description 29
- 229920002396 Polyurea Polymers 0.000 title claims abstract description 13
- 229920001187 thermosetting polymer Polymers 0.000 title description 2
- -1 polytetramethylene Polymers 0.000 claims abstract description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000012948 isocyanate Substances 0.000 claims abstract description 24
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 24
- 238000005266 casting Methods 0.000 claims abstract description 16
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 14
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 12
- 239000010452 phosphate Substances 0.000 claims abstract description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011541 reaction mixture Substances 0.000 claims abstract description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 6
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000005442 diisocyanate group Chemical group 0.000 claims description 8
- 229920005906 polyester polyol Polymers 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 5
- BSYVFGQQLJNJJG-UHFFFAOYSA-N 2-[2-(2-aminophenyl)sulfanylethylsulfanyl]aniline Chemical compound NC1=CC=CC=C1SCCSC1=CC=CC=C1N BSYVFGQQLJNJJG-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 4
- ZYCRBOCGBKATBL-UHFFFAOYSA-N 3-tert-butyl-6-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(C(C)(C)C)C(N)=C1N ZYCRBOCGBKATBL-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 9
- 229920005862 polyol Polymers 0.000 description 35
- 150000003077 polyols Chemical class 0.000 description 35
- 239000004014 plasticizer Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- RYUJRXVZSJCHDZ-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC(C)C)OC1=CC=CC=C1 RYUJRXVZSJCHDZ-UHFFFAOYSA-N 0.000 description 5
- 150000004984 aromatic diamines Chemical class 0.000 description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- AOFIWCXMXPVSAZ-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(C)=C(N)C(SC)=C1N AOFIWCXMXPVSAZ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- LOCPTSFJZDIICR-UHFFFAOYSA-N 1,3-bis(3-isocyanato-4-methylphenyl)-1,3-diazetidine-2,4-dione Chemical compound C1=C(N=C=O)C(C)=CC=C1N1C(=O)N(C=2C=C(C(C)=CC=2)N=C=O)C1=O LOCPTSFJZDIICR-UHFFFAOYSA-N 0.000 description 3
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 3
- 239000004970 Chain extender Substances 0.000 description 3
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000006177 alkyl benzyl group Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- IPKKHRVROFYTEK-UHFFFAOYSA-N dipentyl phthalate Chemical compound CCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCC IPKKHRVROFYTEK-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N n-Decanedioic acid Natural products OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- ZIZJPRKHEXCVLL-UHFFFAOYSA-N 1,3-bis(6-isocyanatohexyl)-1,3-diazetidine-2,4-dione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C1=O ZIZJPRKHEXCVLL-UHFFFAOYSA-N 0.000 description 1
- RLPSARLYTKXVSE-UHFFFAOYSA-N 1-(1,3-thiazol-5-yl)ethanamine Chemical compound CC(N)C1=CN=CS1 RLPSARLYTKXVSE-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- LIAWCKFOFPPVGF-UHFFFAOYSA-N 2-ethyladamantane Chemical compound C1C(C2)CC3CC1C(CC)C2C3 LIAWCKFOFPPVGF-UHFFFAOYSA-N 0.000 description 1
- ASXSTXLJBYGNBS-UHFFFAOYSA-N 2-o-benzyl 1-o-decyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ASXSTXLJBYGNBS-UHFFFAOYSA-N 0.000 description 1
- ALJDXNRRMJECDM-UHFFFAOYSA-N 2-o-benzyl 1-o-heptyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ALJDXNRRMJECDM-UHFFFAOYSA-N 0.000 description 1
- KGMYJDOPDNACPU-UHFFFAOYSA-N 2-o-benzyl 1-o-hexyl benzene-1,2-dicarboxylate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 KGMYJDOPDNACPU-UHFFFAOYSA-N 0.000 description 1
- WHHSHXMIKFVAEK-UHFFFAOYSA-N 2-o-benzyl 1-o-octyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 WHHSHXMIKFVAEK-UHFFFAOYSA-N 0.000 description 1
- HNOJQCCTWMACFZ-UHFFFAOYSA-N 2-o-benzyl 1-o-propyl benzene-1,2-dicarboxylate Chemical compound CCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 HNOJQCCTWMACFZ-UHFFFAOYSA-N 0.000 description 1
- HMEZGAOEAKNASW-UHFFFAOYSA-L 3-benzyl-4-pentylphthalate Chemical compound CCCCCC1=CC=C(C([O-])=O)C(C([O-])=O)=C1CC1=CC=CC=C1 HMEZGAOEAKNASW-UHFFFAOYSA-L 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000482262 Spreo Species 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000010692 aromatic oil Chemical class 0.000 description 1
- 230000000386 athletic effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- UCVPKAZCQPRWAY-UHFFFAOYSA-N dibenzyl benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC=2C=CC=CC=2)C=1C(=O)OCC1=CC=CC=C1 UCVPKAZCQPRWAY-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- LXXOSDVHTQEPQJ-UHFFFAOYSA-N heptyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCC)OC1=CC=CC=C1 LXXOSDVHTQEPQJ-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- BKENCPVCULYKSA-UHFFFAOYSA-N nonyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCCC)OC1=CC=CC=C1 BKENCPVCULYKSA-UHFFFAOYSA-N 0.000 description 1
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- BVXSDQYDTOKNMQ-UHFFFAOYSA-N pentyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCC)OC1=CC=CC=C1 BVXSDQYDTOKNMQ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000008029 phthalate plasticizer Substances 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- SJAUZDFPAWWLCG-UHFFFAOYSA-N tris(2-ethoxyethyl) phosphate Chemical compound CCOCCOP(=O)(OCCOCC)OCCOCC SJAUZDFPAWWLCG-UHFFFAOYSA-N 0.000 description 1
- QLNUSZCPEUTHBS-UHFFFAOYSA-N tris(2-methoxyethyl) phosphate Chemical compound COCCOP(=O)(OCCOC)OCCOC QLNUSZCPEUTHBS-UHFFFAOYSA-N 0.000 description 1
- MWCGEFZLNZHVQL-UHFFFAOYSA-N tris(2-pentoxyethyl) phosphate Chemical compound CCCCCOCCOP(=O)(OCCOCCCCC)OCCOCCCCC MWCGEFZLNZHVQL-UHFFFAOYSA-N 0.000 description 1
- OOBSXDNTZUFBDF-UHFFFAOYSA-N tris(2-propoxyethyl) phosphate Chemical compound CCCOCCOP(=O)(OCCOCCC)OCCOCCC OOBSXDNTZUFBDF-UHFFFAOYSA-N 0.000 description 1
- HHMUWWOGOHDKNE-UHFFFAOYSA-N tris(3-butoxypropyl) phosphate Chemical compound CCCCOCCCOP(=O)(OCCCOCCCC)OCCCOCCCC HHMUWWOGOHDKNE-UHFFFAOYSA-N 0.000 description 1
- MHBJNCDNWZJDTK-UHFFFAOYSA-N tris(3-ethoxypropyl) phosphate Chemical compound CCOCCCOP(=O)(OCCCOCC)OCCCOCC MHBJNCDNWZJDTK-UHFFFAOYSA-N 0.000 description 1
- SZCRFWNYWWYUFE-UHFFFAOYSA-N tris(3-methoxypropyl) phosphate Chemical compound COCCCOP(=O)(OCCCOC)OCCCOC SZCRFWNYWWYUFE-UHFFFAOYSA-N 0.000 description 1
- NYDXLCNFRKROEO-UHFFFAOYSA-N tris(3-pentoxypropyl) phosphate Chemical compound CCCCCOCCCOP(=O)(OCCCOCCCCC)OCCCOCCCCC NYDXLCNFRKROEO-UHFFFAOYSA-N 0.000 description 1
- KOEVADMYQCVUHI-UHFFFAOYSA-N tris(3-propoxypropyl) phosphate Chemical compound CCCOCCCOP(=O)(OCCCOCCC)OCCCOCCC KOEVADMYQCVUHI-UHFFFAOYSA-N 0.000 description 1
- BVDQDMKUURLJDY-UHFFFAOYSA-N tris(4-butoxybutyl) phosphate Chemical compound CCCCOCCCCOP(=O)(OCCCCOCCCC)OCCCCOCCCC BVDQDMKUURLJDY-UHFFFAOYSA-N 0.000 description 1
- MCNOMECOXIQVKJ-UHFFFAOYSA-N tris(4-ethoxybutyl) phosphate Chemical compound CCOCCCCOP(=O)(OCCCCOCC)OCCCCOCC MCNOMECOXIQVKJ-UHFFFAOYSA-N 0.000 description 1
- RJAXJFWBJQWSHY-UHFFFAOYSA-N tris(4-methoxybutyl) phosphate Chemical compound COCCCCOP(=O)(OCCCCOC)OCCCCOC RJAXJFWBJQWSHY-UHFFFAOYSA-N 0.000 description 1
- XGHZKVYJDWWBLY-UHFFFAOYSA-N tris(4-pentoxybutyl) phosphate Chemical compound CCCCCOCCCCOP(=O)(OCCCCOCCCCC)OCCCCOCCCCC XGHZKVYJDWWBLY-UHFFFAOYSA-N 0.000 description 1
- CAKRUWMWXMFZRZ-UHFFFAOYSA-N tris(4-propoxybutyl) phosphate Chemical compound CCCOCCCCOP(=O)(OCCCCOCCC)OCCCCOCCC CAKRUWMWXMFZRZ-UHFFFAOYSA-N 0.000 description 1
- IWLYYHQLANWSOA-UHFFFAOYSA-N tris(5-ethoxypentyl) phosphate Chemical compound CCOCCCCCOP(=O)(OCCCCCOCC)OCCCCCOCC IWLYYHQLANWSOA-UHFFFAOYSA-N 0.000 description 1
- OJHNBWPMTGASIR-UHFFFAOYSA-N tris(5-methoxypentyl) phosphate Chemical compound COCCCCCOP(=O)(OCCCCCOC)OCCCCCOC OJHNBWPMTGASIR-UHFFFAOYSA-N 0.000 description 1
- YFUGCHNCMUKPSN-UHFFFAOYSA-N tris(5-pentoxypentyl) phosphate Chemical compound CCCCCOCCCCCOP(=O)(OCCCCCOCCCCC)OCCCCCOCCCCC YFUGCHNCMUKPSN-UHFFFAOYSA-N 0.000 description 1
- LZNNNFLINXJEIL-UHFFFAOYSA-N tris(butoxymethyl) phosphate Chemical compound CCCCOCOP(=O)(OCOCCCC)OCOCCCC LZNNNFLINXJEIL-UHFFFAOYSA-N 0.000 description 1
- XMLZCZQPFYYGRH-UHFFFAOYSA-N tris(ethoxymethyl) phosphate Chemical compound CCOCOP(=O)(OCOCC)OCOCC XMLZCZQPFYYGRH-UHFFFAOYSA-N 0.000 description 1
- NUZMKXUXRLWEHH-UHFFFAOYSA-N tris(methoxymethyl) phosphate Chemical compound COCOP(=O)(OCOC)OCOC NUZMKXUXRLWEHH-UHFFFAOYSA-N 0.000 description 1
- ITPOQTSKIIRHOM-UHFFFAOYSA-N tris(pentoxymethyl) phosphate Chemical compound CCCCCOCOP(=O)(OCOCCCCC)OCOCCCCC ITPOQTSKIIRHOM-UHFFFAOYSA-N 0.000 description 1
- XRQMGMDGBBFYTM-UHFFFAOYSA-N tris(propoxymethyl) phosphate Chemical compound CCCOCOP(=O)(OCOCCC)OCOCCC XRQMGMDGBBFYTM-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 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
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11265698P | 1998-12-17 | 1998-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200104555B true ZA200104555B (en) | 2002-06-05 |
Family
ID=22345151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200104555A ZA200104555B (en) | 1998-12-17 | 2001-06-04 | Thermosetting poly urethane/urea-forming compositions. |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1157055B1 (zh) |
| JP (1) | JP2002532590A (zh) |
| KR (1) | KR100632310B1 (zh) |
| AT (1) | ATE312858T1 (zh) |
| AU (1) | AU766374B2 (zh) |
| CA (1) | CA2352197A1 (zh) |
| DE (1) | DE69928968T2 (zh) |
| DK (1) | DK1157055T3 (zh) |
| ES (1) | ES2252994T3 (zh) |
| TW (1) | TW499444B (zh) |
| WO (1) | WO2000035983A1 (zh) |
| ZA (1) | ZA200104555B (zh) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9926006D0 (en) * | 1999-11-04 | 2000-01-12 | Ciba Sc Holding Ag | Polurethane/polyurea-forming compositions |
| NL1019152C2 (nl) * | 2001-10-10 | 2003-04-18 | Genimedical B V | Werkwijze voor het aanbrengen van een kunststofgips verband aan een deel van een lichaam. |
| DE102012102852B4 (de) * | 2012-04-02 | 2014-10-30 | Rampf Tooling Solutions GmbH & Co. KG | Verwendung eines Kunststoff-Reaktionsgemisches in einem Verfahren zur Herstellung einer Frontgussbeschichtung für Giessereianwendungen, Formplatte oder Kernkasten mit einem Hinterbau und einer Frontgussbeschichtung sowie Verfahren zur Herstellung eines Gussstücks oder Werkzeugs |
| JP6580774B1 (ja) * | 2018-05-16 | 2019-09-25 | 第一工業製薬株式会社 | 熱可塑性マトリックス樹脂形成用二液硬化型組成物、繊維強化複合材料用マトリックス樹脂、及び繊維強化複合材料 |
| MX2022014103A (es) * | 2020-05-11 | 2022-12-08 | Huntsman Int Llc | Una composicion aglutinante. |
Family Cites Families (5)
| 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 |
| US5059671A (en) * | 1988-12-28 | 1991-10-22 | Mitsui Toatsu Chemicals, Inc. | Manufacturing process of spray urethane elastomer |
| JPH0772223B2 (ja) * | 1991-07-13 | 1995-08-02 | 三洋化成工業株式会社 | ポリウレタン系エラストマーの製造方法 |
| JP3114557B2 (ja) * | 1994-04-21 | 2000-12-04 | 保土谷化学工業株式会社 | 常温硬化型速硬化性ポリウレタン塗膜防水材の製造方法 |
| FR2764893A1 (fr) * | 1997-06-20 | 1998-12-24 | Roland Alexandre Ganga | Elastomeres polyurethannes-polyurees a tres haute tenue en temperature et/ou ignifuges |
-
1999
- 1999-12-15 TW TW088121970A patent/TW499444B/zh not_active IP Right Cessation
- 1999-12-17 ES ES99964587T patent/ES2252994T3/es not_active Expired - Lifetime
- 1999-12-17 AU AU30394/00A patent/AU766374B2/en not_active Ceased
- 1999-12-17 DE DE69928968T patent/DE69928968T2/de not_active Expired - Fee Related
- 1999-12-17 JP JP2000588237A patent/JP2002532590A/ja active Pending
- 1999-12-17 KR KR1020017007396A patent/KR100632310B1/ko not_active IP Right Cessation
- 1999-12-17 AT AT99964587T patent/ATE312858T1/de not_active IP Right Cessation
- 1999-12-17 WO PCT/EP1999/010040 patent/WO2000035983A1/en active IP Right Grant
- 1999-12-17 EP EP99964587A patent/EP1157055B1/en not_active Expired - Lifetime
- 1999-12-17 CA CA002352197A patent/CA2352197A1/en not_active Abandoned
- 1999-12-17 DK DK99964587T patent/DK1157055T3/da active
-
2001
- 2001-06-04 ZA ZA200104555A patent/ZA200104555B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000035983A1 (en) | 2000-06-22 |
| TW499444B (en) | 2002-08-21 |
| EP1157055A1 (en) | 2001-11-28 |
| DK1157055T3 (da) | 2006-02-13 |
| ATE312858T1 (de) | 2005-12-15 |
| KR100632310B1 (ko) | 2006-10-11 |
| AU766374B2 (en) | 2003-10-16 |
| DE69928968T2 (de) | 2006-07-20 |
| AU3039400A (en) | 2000-07-03 |
| JP2002532590A (ja) | 2002-10-02 |
| ES2252994T3 (es) | 2006-05-16 |
| CA2352197A1 (en) | 2000-06-22 |
| EP1157055B1 (en) | 2005-12-14 |
| KR20010082341A (ko) | 2001-08-29 |
| DE69928968D1 (de) | 2006-01-19 |
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