CA2877114C - Halogen-free flame retardant tpu with very high loi - Google Patents
Halogen-free flame retardant tpu with very high loi Download PDFInfo
- Publication number
- CA2877114C CA2877114C CA2877114A CA2877114A CA2877114C CA 2877114 C CA2877114 C CA 2877114C CA 2877114 A CA2877114 A CA 2877114A CA 2877114 A CA2877114 A CA 2877114A CA 2877114 C CA2877114 C CA 2877114C
- Authority
- CA
- Canada
- Prior art keywords
- flame retardant
- phosphate
- tpu
- composition
- component
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 139
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 title description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 247
- 239000004433 Thermoplastic polyurethane Substances 0.000 claims abstract description 228
- 239000000203 mixture Substances 0.000 claims abstract description 169
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims abstract description 132
- 238000000034 method Methods 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims description 76
- -1 polytetrafluoroethylene Polymers 0.000 claims description 72
- 239000004417 polycarbonate Substances 0.000 claims description 66
- 229910019142 PO4 Inorganic materials 0.000 claims description 65
- 229920000515 polycarbonate Polymers 0.000 claims description 64
- 239000010452 phosphate Substances 0.000 claims description 63
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 57
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 44
- 229920000642 polymer Polymers 0.000 claims description 38
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 18
- 229920000570 polyether Polymers 0.000 claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 16
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 14
- 229920001169 thermoplastic Polymers 0.000 claims description 14
- 239000004416 thermosoftening plastic Substances 0.000 claims description 13
- 229920000728 polyester Polymers 0.000 claims description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 10
- 229920005749 polyurethane resin Polymers 0.000 claims description 10
- 150000007974 melamines Chemical class 0.000 claims description 9
- 239000011787 zinc oxide Substances 0.000 claims description 9
- LAUIXFSZFKWUCT-UHFFFAOYSA-N [4-[2-(4-phosphonooxyphenyl)propan-2-yl]phenyl] dihydrogen phosphate Chemical compound C=1C=C(OP(O)(O)=O)C=CC=1C(C)(C)C1=CC=C(OP(O)(O)=O)C=C1 LAUIXFSZFKWUCT-UHFFFAOYSA-N 0.000 claims description 7
- 150000003863 ammonium salts Chemical class 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 claims description 7
- 229910000149 boron phosphate Inorganic materials 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229920000877 Melamine resin Chemical class 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical class NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 5
- 229920000388 Polyphosphate Polymers 0.000 claims description 5
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical class OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 claims description 5
- 239000001205 polyphosphate Substances 0.000 claims description 5
- 235000011176 polyphosphates Nutrition 0.000 claims description 5
- 239000004114 Ammonium polyphosphate Chemical class 0.000 claims description 4
- 229920001276 ammonium polyphosphate Chemical class 0.000 claims description 4
- 235000019826 ammonium polyphosphate Nutrition 0.000 claims description 4
- 239000000395 magnesium oxide Substances 0.000 claims description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 4
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical class NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 claims description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 4
- KEYCPIDAZLIGNV-UHFFFAOYSA-N (diphosphonoamino)phosphonic acid;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)N(P(O)(O)=O)P(O)(O)=O KEYCPIDAZLIGNV-UHFFFAOYSA-N 0.000 claims description 3
- ZSFDBVJMDCMTBM-UHFFFAOYSA-N ethane-1,2-diamine;phosphoric acid Chemical compound NCCN.OP(O)(O)=O ZSFDBVJMDCMTBM-UHFFFAOYSA-N 0.000 claims description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 3
- CZQYVJUCYIRDFR-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical class NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O CZQYVJUCYIRDFR-UHFFFAOYSA-N 0.000 claims description 3
- QVJYHZQHDMNONA-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical class OP(O)(O)=O.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1 QVJYHZQHDMNONA-UHFFFAOYSA-N 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical class C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000743 hydrocarbylene group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract description 18
- 150000002367 halogens Chemical class 0.000 abstract description 18
- 239000000779 smoke Substances 0.000 abstract description 7
- 238000000465 moulding Methods 0.000 abstract description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 75
- 235000021317 phosphate Nutrition 0.000 description 52
- 229920005989 resin Polymers 0.000 description 36
- 239000011347 resin Substances 0.000 description 36
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 33
- 239000000654 additive Substances 0.000 description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
- 239000000463 material Substances 0.000 description 23
- 239000004970 Chain extender Substances 0.000 description 19
- 239000000543 intermediate Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 230000000996 additive effect Effects 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000004020 conductor Substances 0.000 description 12
- 239000003381 stabilizer Substances 0.000 description 11
- 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 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 10
- 239000005056 polyisocyanate Substances 0.000 description 10
- 229920001228 polyisocyanate Polymers 0.000 description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 9
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 9
- 238000010276 construction Methods 0.000 description 9
- 150000002009 diols Chemical group 0.000 description 9
- 150000002334 glycols Chemical class 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 8
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-DYCDLGHISA-N deuterium hydrogen oxide Chemical compound [2H]O XLYOFNOQVPJJNP-DYCDLGHISA-N 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 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 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 238000007706 flame test Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 102100024482 Cell division cycle-associated protein 4 Human genes 0.000 description 3
- 101100383112 Homo sapiens CDCA4 gene Proteins 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 239000012796 inorganic flame retardant Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- KQDIGHIVUUADBZ-PEDHHIEDSA-N pentigetide Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(O)=O KQDIGHIVUUADBZ-PEDHHIEDSA-N 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical class C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 2
- 239000001177 diphosphate Substances 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004712 monophosphates Chemical class 0.000 description 2
- 239000012802 nanoclay Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229940117969 neopentyl glycol Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- MWFNQNPDUTULBC-UHFFFAOYSA-N phosphono dihydrogen phosphate;piperazine Chemical compound C1CNCCN1.OP(O)(=O)OP(O)(O)=O MWFNQNPDUTULBC-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000007970 thio esters 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
- 239000001226 triphosphate Substances 0.000 description 2
- 235000011178 triphosphate Nutrition 0.000 description 2
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- FSBFENGFYVITPO-UHFFFAOYSA-N (2,3-dimethylphenyl) diphenyl phosphate Chemical compound CC1=CC=CC(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)=C1C FSBFENGFYVITPO-UHFFFAOYSA-N 0.000 description 1
- OWICEWMBIBPFAH-UHFFFAOYSA-N (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1)(=O)OC1=CC=CC=C1 OWICEWMBIBPFAH-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- NOPNBQOZUKISRP-UHFFFAOYSA-N (4-hydroxyphenyl) diphenyl phosphate Chemical compound C1=CC(O)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 NOPNBQOZUKISRP-UHFFFAOYSA-N 0.000 description 1
- LMCLPMXCYFSRNG-UHFFFAOYSA-N (4-nonylphenyl) diphenyl phosphate Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 LMCLPMXCYFSRNG-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- VKSWWACDZPRJAP-UHFFFAOYSA-N 1,3-dioxepan-2-one Chemical compound O=C1OCCCCO1 VKSWWACDZPRJAP-UHFFFAOYSA-N 0.000 description 1
- ANLVEXKNRYNLDH-UHFFFAOYSA-N 1,3-dioxonan-2-one Chemical compound O=C1OCCCCCCO1 ANLVEXKNRYNLDH-UHFFFAOYSA-N 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
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- HLSUQUJDDMLNMX-UHFFFAOYSA-N 1-(2-octadec-9-enoxyethoxy)octadec-9-ene Chemical class CCCCCCCCC=CCCCCCCCCOCCOCCCCCCCCC=CCCCCCCCC HLSUQUJDDMLNMX-UHFFFAOYSA-N 0.000 description 1
- YZGMIRBFYCQNRH-UHFFFAOYSA-N 2-(2-hydroxyethyl)benzene-1,3-diol Chemical compound OCCC1=C(O)C=CC=C1O YZGMIRBFYCQNRH-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
- VOTNIUQWGPWUDZ-UHFFFAOYSA-N 3-butyl-1,5-diphenylpyrazole Chemical compound C=1C=CC=CC=1N1N=C(CCCC)C=C1C1=CC=CC=C1 VOTNIUQWGPWUDZ-UHFFFAOYSA-N 0.000 description 1
- WXKUUQALRCTOJF-UHFFFAOYSA-N 3-dimethoxyphosphoryl-n-methylpropanamide Chemical compound CNC(=O)CCP(=O)(OC)OC WXKUUQALRCTOJF-UHFFFAOYSA-N 0.000 description 1
- JRQLZCFSWYQHPI-UHFFFAOYSA-N 4,5-dichloro-2-cyclohexyl-1,2-thiazol-3-one Chemical compound O=C1C(Cl)=C(Cl)SN1C1CCCCC1 JRQLZCFSWYQHPI-UHFFFAOYSA-N 0.000 description 1
- LWLOKSXSAUHTJO-UHFFFAOYSA-N 4,5-dimethyl-1,3-dioxolan-2-one Chemical compound CC1OC(=O)OC1C LWLOKSXSAUHTJO-UHFFFAOYSA-N 0.000 description 1
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- FEUQWJRZKZQFAO-UHFFFAOYSA-N hexadecyl diphenyl phosphate Chemical class C=1C=CC=CC=1OP(=O)(OCCCCCCCCCCCCCCCC)OC1=CC=CC=C1 FEUQWJRZKZQFAO-UHFFFAOYSA-N 0.000 description 1
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- BGNTUSKZDOUZCZ-UHFFFAOYSA-N tris(1-butoxyethyl) phosphate Chemical compound CCCCOC(C)OP(=O)(OC(C)OCCCC)OC(C)OCCCC BGNTUSKZDOUZCZ-UHFFFAOYSA-N 0.000 description 1
- AZSKHRTUXHLAHS-UHFFFAOYSA-N tris(2,4-di-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(=O)(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C AZSKHRTUXHLAHS-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K3/32—Phosphorus-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/04—Polyurethanes
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- 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
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- C08K5/0066—Flame-proofing or flame-retarding additives
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- 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
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- 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
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- C08K5/51—Phosphorus bound to oxygen
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- 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
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- C08K5/5205—Salts of P-acids with N-bases
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- 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
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- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/14—Macromolecular materials
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- 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
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- C08K3/38—Boron-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261660869P | 2012-06-18 | 2012-06-18 | |
| US61/660,869 | 2012-06-18 | ||
| PCT/US2013/044202 WO2013191902A1 (en) | 2012-06-18 | 2013-06-05 | Halogen-free flame retardant tpu with very high loi |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2877114A1 CA2877114A1 (en) | 2013-12-27 |
| CA2877114C true CA2877114C (en) | 2020-08-25 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2877114A Active CA2877114C (en) | 2012-06-18 | 2013-06-05 | Halogen-free flame retardant tpu with very high loi |
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Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10738159B2 (en) * | 2016-03-14 | 2020-08-11 | Adeka Corporation | Flame retardant thermoplastic polyurethane resin composition |
| CN111356732A (zh) * | 2017-11-03 | 2020-06-30 | 巴斯夫欧洲公司 | 阻燃剂组合物、其制备方法及其制品 |
| EP3620478A1 (en) | 2018-09-10 | 2020-03-11 | Covestro Deutschland AG | Use of thermoplastic polyurethanes for applications subject to significant everyday stress |
| WO2020048881A1 (en) | 2018-09-06 | 2020-03-12 | Covestro Deutschland Ag | Use of thermoplastic polyurethanes for applications subject to significant everyday stress |
| CN109400846A (zh) * | 2018-10-27 | 2019-03-01 | 濮阳天健生物科技有限公司 | 一种化工反应釜用复合保温板及其制备方法 |
| US11840656B2 (en) * | 2021-11-05 | 2023-12-12 | Industrial Technology Research Institute | Halogen free flame-retardant materials and method for manufacturing the same |
| CN115304903B (zh) * | 2022-09-02 | 2023-06-23 | 四川龙华光电薄膜股份有限公司 | 一种tpu改性树脂及应用 |
| CN115353728B (zh) * | 2022-09-02 | 2023-06-23 | 四川龙华光电薄膜股份有限公司 | 一种改性pc及tpu的复合材料及其制备方法和应用 |
| US20250075074A1 (en) | 2023-09-05 | 2025-03-06 | Te Connectivity Solutions Gmbh | Thermally Stable, Fire Resistant Thermoplastic Polymer Composition for Heat/Fire Propagation Applications |
| US20250075068A1 (en) | 2023-09-05 | 2025-03-06 | Te Connectivity Solutions Gmbh | Thermally Stable, Fire Resistant Thermoset Polymer Composition for Heat/Fire Propagation Applications |
| CN118206863B (zh) * | 2024-03-14 | 2025-04-18 | 江苏普清净化科技有限公司 | 一种防静电高阻隔高分子薄膜及其在半导体包装中的应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4131731A (en) | 1976-11-08 | 1978-12-26 | Beatrice Foods Company | Process for preparing polycarbonates |
| US4542170A (en) * | 1985-01-22 | 1985-09-17 | The B. F. Goodrich Company | Intumescent flame retarded polyurethane compositions |
| DE4100383A1 (de) * | 1991-01-09 | 1992-07-16 | Rhein Chemie Rheinau Gmbh | Polyurethanbeschichtungsmassen |
| US5110850A (en) | 1991-04-10 | 1992-05-05 | B. F. Goodrich Company | Halogen-free, flame-retardant thermoplastic polyurethane containing melamine |
| US5837760A (en) | 1994-03-16 | 1998-11-17 | Elastogran Gmbh | Self-extinguishing thermoplastic polyurethanes and their preparation |
| JP3249940B2 (ja) * | 1997-12-05 | 2002-01-28 | キョーワ株式会社 | メッシュシート用難燃剤とこれを用い防炎メッシュシート |
| US6777466B2 (en) | 2002-02-08 | 2004-08-17 | Noveon Ip Holdings Corp. | Flame retardant thermoplastic polyurethane containing melamine cyanurate |
| US7417083B2 (en) * | 2004-04-01 | 2008-08-26 | Sabic Innovative Plastics Ip B.V. | Flame retardant composition |
| DE602005016235D1 (de) * | 2004-04-01 | 2009-10-08 | Sabic Innovative Plastics Ip | Flammschutzmittelzusammensetzung |
| ES2352334T3 (es) | 2005-04-13 | 2011-02-17 | Lubrizol Advanced Materials, Inc. | Poliuretano termoplástico retardador de llama sin halógeno. |
| JP5424444B2 (ja) * | 2008-06-06 | 2014-02-26 | 株式会社Ａｄｅｋａ | 難燃性熱可塑性樹脂組成物 |
| KR101476495B1 (ko) * | 2008-07-30 | 2014-12-24 | 다우 글로벌 테크놀로지스 엘엘씨 | 내연성 폴리우레탄 조성물 |
| JP5344742B2 (ja) * | 2008-08-01 | 2013-11-20 | 株式会社Ａｄｅｋａ | 難燃性熱可塑性樹脂組成物 |
| JP2012530801A (ja) * | 2009-06-18 | 2012-12-06 | ダウ グローバル テクノロジーズ エルエルシー | 色の安定なハロゲンフリー難燃性組成物 |
| CN102803382B (zh) * | 2009-06-26 | 2015-06-24 | 陶氏环球技术有限责任公司 | 含有环氧化酚醛清漆的热塑性组合物 |
| EP2464686B1 (en) * | 2009-08-10 | 2019-05-08 | Union Carbide Chemicals & Plastics Technology LLC | Thermoplastic elastomer compositions comprising intumescent flame retardants and non-phosphorous-based flame retardant synergists |
| BR112012015028B1 (pt) * | 2009-12-18 | 2019-06-18 | Dow Global Technologies Llc | Composição retardante de chamas e encapamento de fios ou cabos |
| WO2011120225A1 (en) | 2010-03-31 | 2011-10-06 | Dow Global Technologies Llc | Migration-free, halogen-free, flame retardant thermoplastic polyurethane compositions |
| US8957141B2 (en) | 2010-11-16 | 2015-02-17 | Lubrizol Advanced Materials, Inc. | Non halogen flame retardant thermoplastic polyurethane |
-
2013
- 2013-06-05 EP EP13729212.4A patent/EP2861694B1/en active Active
- 2013-06-05 CA CA2877114A patent/CA2877114C/en active Active
- 2013-06-05 US US14/406,902 patent/US9920166B2/en active Active
- 2013-06-05 IN IN10483DEN2014 patent/IN2014DN10483A/en unknown
- 2013-06-05 CN CN201380042897.8A patent/CN104540924B/zh active Active
- 2013-06-05 WO PCT/US2013/044202 patent/WO2013191902A1/en active Application Filing
- 2013-06-05 KR KR1020157001196A patent/KR102166379B1/ko active Active
- 2013-06-05 ES ES13729212.4T patent/ES2691638T3/es active Active
- 2013-06-14 TW TW102121101A patent/TWI639688B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| TW201402797A (zh) | 2014-01-16 |
| CN104540924B (zh) | 2019-11-12 |
| TWI639688B (zh) | 2018-11-01 |
| CA2877114A1 (en) | 2013-12-27 |
| KR20150023787A (ko) | 2015-03-05 |
| CN104540924A (zh) | 2015-04-22 |
| EP2861694B1 (en) | 2018-10-03 |
| ES2691638T3 (es) | 2018-11-28 |
| KR102166379B1 (ko) | 2020-10-15 |
| IN2014DN10483A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-08-21 |
| WO2013191902A1 (en) | 2013-12-27 |
| US20150152222A1 (en) | 2015-06-04 |
| EP2861694A1 (en) | 2015-04-22 |
| US9920166B2 (en) | 2018-03-20 |
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| KR102259248B1 (ko) | 할로겐-비함유 방염 ｔｐｕ | |
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