JPH0478652B2 - - Google Patents
Info
- Publication number
- JPH0478652B2 JPH0478652B2 JP27196587A JP27196587A JPH0478652B2 JP H0478652 B2 JPH0478652 B2 JP H0478652B2 JP 27196587 A JP27196587 A JP 27196587A JP 27196587 A JP27196587 A JP 27196587A JP H0478652 B2 JPH0478652 B2 JP H0478652B2
- Authority
- JP
- Japan
- Prior art keywords
- mixture
- weight
- antimony oxide
- carbon atoms
- sodium
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims description 59
- -1 polyethylene terephthalate Polymers 0.000 claims description 57
- 229910000410 antimony oxide Inorganic materials 0.000 claims description 32
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 32
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 29
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 29
- 239000004952 Polyamide Substances 0.000 claims description 17
- 229920002647 polyamide Polymers 0.000 claims description 17
- 239000003063 flame retardant Substances 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000012141 concentrate Substances 0.000 claims description 12
- 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 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 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 class 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 description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000004793 Polystyrene Substances 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229920002223 polystyrene Polymers 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- 238000000465 moulding Methods 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 239000008188 pellet Substances 0.000 claims description 5
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- CIPFDHFTBYJKQB-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-(2,3,4,5,6-pentachlorophenoxy)benzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CIPFDHFTBYJKQB-UHFFFAOYSA-N 0.000 claims description 2
- ORYGKUIDIMIRNN-UHFFFAOYSA-N 1,2,3,4-tetrabromo-5-(2,3,4,5-tetrabromophenoxy)benzene Chemical compound BrC1=C(Br)C(Br)=CC(OC=2C(=C(Br)C(Br)=C(Br)C=2)Br)=C1Br ORYGKUIDIMIRNN-UHFFFAOYSA-N 0.000 claims description 2
- IXZVOZCULZBCDY-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-(2,3,4,5-tetrachlorophenoxy)benzene Chemical compound ClC1=C(Cl)C(Cl)=CC(OC=2C(=C(Cl)C(Cl)=C(Cl)C=2)Cl)=C1Cl IXZVOZCULZBCDY-UHFFFAOYSA-N 0.000 claims description 2
- DYIZJUDNMOIZQO-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O DYIZJUDNMOIZQO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 claims description 2
- KNEOLQHWXNLTOV-UHFFFAOYSA-N ethene 4,5,6,7-tetrachloroisoindole-1,3-dione Chemical compound ClC=1C(=C(C(=C2C1C(=O)NC2=O)Cl)Cl)Cl.ClC=2C(=C(C(=C1C2C(=O)NC1=O)Cl)Cl)Cl.C=C KNEOLQHWXNLTOV-UHFFFAOYSA-N 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 239000004711 α-olefin Substances 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000003014 reinforcing effect Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 description 14
- 229910052783 alkali metal Inorganic materials 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 10
- 239000004677 Nylon Substances 0.000 description 8
- 229920002292 Nylon 6 Polymers 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 229920001778 nylon Polymers 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920002302 Nylon 6,6 Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001412 amines Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000002787 reinforcement Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- WCUBBMIUIPEPOH-UHFFFAOYSA-N 4-methyl-n-octadecylbenzenesulfonamide Chemical compound CCCCCCCCCCCCCCCCCCNS(=O)(=O)C1=CC=C(C)C=C1 WCUBBMIUIPEPOH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 229920000299 Nylon 12 Polymers 0.000 description 2
- 229920000305 Nylon 6,10 Polymers 0.000 description 2
- 229920003182 Surlyn® Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 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
- 238000013329 compounding Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- 239000002667 nucleating agent Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 229920006051 Capron® Polymers 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- OCKWAZCWKSMKNC-UHFFFAOYSA-N [3-octadecanoyloxy-2,2-bis(octadecanoyloxymethyl)propyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC OCKWAZCWKSMKNC-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 230000002053 acidogenic effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001034 aminogenic effect Effects 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000368 destabilizing effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052806 inorganic carbonate Inorganic materials 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- 239000013638 trimer Chemical class 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
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FIELD OF THE INVENTION The present invention relates to polyethylene terephthalate molding mixtures and more particularly to such mixtures which can be molded to obtain molded articles with improved flame retardancy. BACKGROUND OF THE INVENTION Polyethylene terephthalate is an inexpensive polymer, but until recently it has not been recognized as a good molding resin for a number of reasons. for example,
Alkali metal salts of certain organic carboxyl-containing compositions (alkali metal organic carboxylates)
is commonly added to promote crystallization by enhancing nucleation of polyethylene terephthalate. Furthermore, polyethylene terephthalate is generally made flame retardant by the addition of conventional flame retardants, such as halogenated organic compounds and antimony oxide synergists. However, when a flame retardant system containing an antimony oxide synergist is added to a mixture of polyethylene terephthalate and alkali metal organic carboxylate, polymer decomposition occurs resulting in decreased mechanical properties and decreased melt viscosity. This degradation in the presence of antimony oxide is particularly unfortunate since antimony oxide is a particularly good synergist for halogenated aromatic organic flame retardants. It is readily available, inexpensive and highly effective. In contrast, many other inorganic synergists are simply not effective in polyethylene terephthalate flame retardant systems or degrade the resin when used with polyethylene terephthalate, including zinc oxide, zinc sulfide, Zinc borate, stannous oxide, molybdenum oxide and molybdate. There is a need for a flame retardant system using antimony oxide that does not substantially affect the thermal stability of polyethylene terephthalate when added to a mixture of polyethylene terephthalate and an alkali metal carboxylate; This can be provided by the invention. SUMMARY OF THE INVENTION It has now been found that the destabilizing effect of antimony oxide on mixtures of alkali metal organic carboxylates is minimized when the antimony oxide is added in the form of a concentrate in the polyamide. This improves the stability of polyethylene terephthalate during compounding and subsequent melt processing operations, such as injection molding, when added in the form of concentrates in other heavy machinery polymers, such as polyethylene, or as is. Significant improvement compared to when adding In particular, the polyethylene terephthalate molding mixture of the present invention comprises: (a) from 20 to 90% by weight of the mixture, at least 0.4
polyethylene terephthalate having an inherent viscosity of (b) 0.1 to 20% by weight of the mixture of (a) and (b), from 7 to
Sodium and/or at least one carboxyl-containing organic compound selected from the class consisting of hydrocarbon monocarboxylic acids containing 25 carbon atoms, hydrocarbon di- or tricarboxylic acids containing 7 to 54 carbon atoms, and organic carboxyl-containing polymers. (c) a halogenated flame retardant consisting of an aromatic organic compound having at least one aromatic ring having sufficient halogen bonded directly to the aromatic ring carbon to provide flame retardancy; (d) the flame retardant is present in the mixture in an amount sufficient to provide the mixture with halogen in an amount of about 5 to 30% by weight based on the weight of the mixture of (a) and (c); 0.3 by weight based on the weight of the mixture of ) and (d)
~8% antimony oxide, the antimony oxide being added to the mixture in the form of a concentrate in the polyamide, the concentrate containing from 20 to 80% by weight of antimony oxide based on the combined weight of antimony oxide and polyamide , is defined as consisting of . Usually the mixture contains reinforcing agents or fillers ranging from 0 to 55% by weight. DESCRIPTION OF THE INVENTION Polyethylene Terephthalate The polyethylene terephthalate used in this invention has an inherent viscosity of at least 0.4 as measured by ASTM D-2857. Preferably, it has an upper limit on inherent viscosity of about 1.2. Inherent viscosity is 0.50 g per 100 ml of methylene chloride and trifluoroacetic acid mixture in a 3:1 ratio by volume.
Measured at 30°C at a concentration of Polyethylene terephthalate contains up to 50% by weight of e.g. diethylene glycol, glutaric acid, 1,4
- May contain other comonomers such as butanediol, polyalkylene oxide, cyclohexanedimethanol and other diols. Preferably, the polyethylene terephthalate is present in an amount of 35 to 70% by weight of the mixture. Reinforcement or Filler Materials Reinforcement or filler materials that can be used in the present invention include glass fibers, graphite fibers, aramid fibers, glass beads, aluminum silicate, asbestos, mica, etc., and combinations thereof. Preferably, this material is present in an amount of 15-55% by weight of the mixture. Alkali metal organic carboxylic acid salts Typical examples of salts of organic carboxylic acids include 2-5-
Ionic hydrocarbon copolymers of alpha-olefins of carbon atoms and alpha, beta ethylenically unsaturated carboxylic acids of 3 to 5 carbon atoms whose carboxyl groups are at least partially neutralized by sodium and/or potassium cations (hereinafter referred to as ionomer resin), for example, a copolymer of ethylene and acrylic or methacrylic acid. These copolymers are preferably sodium or potassium salts (preferably 30 to 95% neutralized) of ethylene/methacrylic acid copolymers. Styrene/maleic anhydride copolymers (including both fully or partially (eg, about 30%) neutralized salts) are also representative examples. The olefin moiety usually accounts for 50-98%, preferably 80-98% by weight of the copolymer. A particularly preferred material is the sodium salt of ethylene/methacrylic acid copolymer. The copolymer can be produced by a conventional high pressure polymerization method. contains at least 7, preferably at least 26, more preferably 30 to 54 carbon atoms, and about 1500
Salts of substantially aliphatic di- or tricarboxylic acids having a molecular weight below, preferably between 450 and 1000, are also another class of examples. These salts are based on polyethylene terephthalate and weigh approximately
It is present in the mixture in an amount of 0.1-5%, preferably 0.35-1.1%. Although both saturated and unsaturated polycarboxylic acids can be used for salt formation, saturated acids are preferred because of their lower tendency to discolor. Additionally, the acid may contain an aryl moiety, such as a phenylene, in the aliphatic chain. Representative substantially aliphatic polycarboxylic acids that can be used to form the salts useful in this invention include dimer acids and trimer acids. Dimer acid means C 36 dicarboxylic acid obtained by dimerization of C 18 fatty acids.
Trimer acid means C 54 tricarboxylic acid obtained by trimerization of C 18 fatty acids. Halogenated Flame Retardants Halogenated flame retardants consist of aromatic compounds containing a halogen, preferably a bromine or chlorine atom, bonded directly to an aromatic ring or rings. If bromine is present, it is at least 25% by weight of the compound, and if chlorine is present, chlorine is at least 40% by weight of the compound. In addition, the flame retardant compound must be substantially stable up to 300°C and must not cause degradation of the polyethylene terephthalate. If the compound contains bromine, the amount of bromine present in the mixture is preferably from 5 to 20% by weight of the mixture with component (a) alone. If the compound contains chlorine, the amount of chlorine present is preferably from 5 to 20% by weight of the mixture with compound (a) alone. Typical flame retardants include decabromodiphenyl ether, octabromodiphenyl ether, ethylene-bis-(tetrabromophthalimide), brominated polystyrene, poly(dibromophenylene oxide), decachlorodiphenyl ether, and octachlorodiphenyl ether. enyl ether, ethylene bis(tetrachlorophthalimide), chlorinated polystyrene,
Includes poly(dichlorophenylene oxide) and the like. Polymeric flame retardants can have molecular weights up to 200,000 or more. Antimony Oxide The antimony oxide (Sb 2 O 3 or Sb 2 O 5 ) used in the present invention is added as a concentrate in the polyamide. It is present in the polyethylene terephthalate mixture in an amount of 0.3 to 8%, preferably 0.3 to 5%, most preferably 0.3 to 1%, based on the weight of the mixture with component (a) alone. The concentration of antimony oxide in the concentrate (antimony oxide + polyamide) is 20-80% by weight. Polyamides useful as supports for antimony oxide are known in the art. They are of film-forming molecular weight. The polyamide resin can be produced by condensation of equimolar amounts of a saturated organic dicarboxylic acid containing from 4 to 12 carbon atoms and an organic diamine containing from 2 to 13 carbon atoms,
Therein, the diamines may be used, if necessary, in such a way that there is an excess of amine end groups over carboxyl end groups in the polyamide. Conversely, a diacid can also be used so that the acid end groups are in excess. Similarly, these polyamides can also be made from acidogenic and aminogenic derivatives of the amines and acids, such as esters, acid chlorides, amine salts, and the like. Representative dicarboxylic acids that can be used for the production of polyamides include adipic acid, pimelic acid, suberic acid, sebacic acid, and dodecanedioic acid, while representative diamines include hexamethylene diamine and octane diamine. Includes methylene diamine. In addition, polyamides can also be produced by self-condensation of Ï-aminocarboxylic acids or lactams.
Examples of polyamides are poly(hexamethylene adipamide) (nylon 66), poly(hexamethylene azeramide) (nylon 69), poly(hexamethylene sebacamide) (nylon 610), and poly(hexamethylene dodecanoamide). ) (612 nylon), poly(4,
4â²-methylenedicyclohexylendodecanoamide) or polyamides prepared by ring opening of lactams, i.e. polycaprolactam (nylon 6), polylauryllactam (nylon 12) or poly-11 prepared from Ï-amino acids. -aminoundecanamide. For example, a copolymer of adipic acid, isophthalic acid and hexamethylene diamine; or hexamethylene diamine;
It is also possible to use polyamide copolymers produced by polymerization with at least two amines or acids for the production of the abovementioned polymers, such as copolymers of adipic acid and caprolactam. Also included are mixtures of polyamides such as nylon 66 and nylon 6. Other Additives In addition to the above-mentioned components, the mixture of the invention may contain, for example, colorants, mold release agents, antioxidants, toughening agents,
Additives commonly used with polyester resins can be included, such as nucleating agents, UV and heat stabilizers, and the like. Suitable additives are selected low molecular weight organic plasticizers which are esters, ketones, sulfones, sulfoxides, nitriles, amides or sulfonamides. Recently, good quality polyethylene terephthalate products have been developed by molding at relatively low temperatures, e.g. It has been found that it is possible to obtain When using these additive materials, the rate of crystallization is increased and molded products can be obtained with a smooth, shiny surface that allows easy demolding. When used, these additives are preferably present in an amount of 1 to 12% by weight of the mixture. In addition, the customary nucleating agents for polyethylene terephthalate, such as inorganic oxides or carbonates, carboxylic acids or other salts of sodium,
Polyethylene terephthalate oligomers can be used. Manufacture The mixtures of the invention are manufactured by melt mixing the components together by any convenient means to obtain an intimate mixture. Neither temperature nor pressure is limiting. For example, polyethylene terephthalate can be dry mixed or rolled with other ingredients in any suitable mixture and the mixture can be melt extruded. The extrudate may be shredded. If desired, the reinforcement or filler can be omitted initially and the resulting mixture then melt extruded. EXPERIMENTAL AND EXAMPLES In the following experiments and examples, percentages are based on the total mixture, unless stated otherwise. The properties of the molded bars were determined according to the following method: Tensile strength and elongation were determined by the method of ASTM D638 on injection molded bars at a pull rate of 0.2 inches per minute. Unnotched impact strength was measured according to ASTM D256 without notching the specimen. For this test and for tensile strength and elongation of Examples 1 and 2 for all samples, the specimens were heat treated in nitrogen at 150° C. for 16 hours. The melt viscosity of the extruded pellets was determined by a Monsanto Automatic capillary rheometer with a cylindrical orifice of 0.0305Ⳡdiameter and 0.62Ⳡlength.
Measurements were made at a constant shear stress of 125 kPa. In the experiments and examples, the manufacturing and testing method was as follows: Each component was dry mixed by hand, and the resulting mixture was then mixed in a two-stage 2-inch single-screw extruder.
It was extruded at a temperature of 300°C and a vacuum of 25-28 inches. After quenching the extruded strands in water, they were cut into pellets, which were then dried in a dehumidified air oven for 16 hours at about 95°C. The dried pellets were injection molded into bar specimens using a 6 oz. Vandoorne reciprocating injection molding machine at a rapid ram speed and a mold cavity temperature of about 105°C. The standard cycle has a melt temperature of approximately 307°C.
It was 33 seconds, corresponding to a residence time of 3 minutes. The severe cycle was 109 seconds, corresponding to a 10 minute residence time, at a melt temperature of about 312°C. Examples 1 and 2 without crystallization promoting additives were molded at a cavity temperature of about 50° C. and then tempered. Antimony oxide (70/30) in nylon 6 is M
&T Chemical Company. Other antimony oxide concentrates in nylon carriers were prepared by compounding the dry mixture in a 28 mm Werner and Freiderer twin screw extruder. The extruded strands are then quenched in water,
After cutting into pellets, they were dried in a dehumidified air oven at about 95° C. for 16 hours. The ingredients used in the experiments and examples are as follows: PET - polyethylene having an inherent viscosity of 0.6, measured at 30°C at a concentration of 0.50 g/100 ml in a mixture of 1 part trifluoroacetic acid and 3 parts dichloromethane. Terephthalate homopolymer resin "Surlyn" 8920 - about 60% by alkali metal organic carboxylate, i.e., ionic hydrocarbon copolymer, i.e., sodium
"Epon" copolymer of neutralized ethylene and 15% methacrylic acid by weight 1009 - condensation product of epichlorohydrin and bisphenol A with a molecular weight of 4000 to 8000 and approximately 0.53% oxirane oxygen . Obtained from Ciel Chemical Company. âIrganoxâ 1010 - Tetrakis [methylene (3,5-di-t-butyl-4-hydroxyhydrocinnamate) methane brominated polystyrene from Ciba Geigy] - Brominated polystyrene (ferrochloride) with a bromine content of 68% Antimony Oxide - Sb 2 O 3 (âThermogardâ S from M&T Chemicals) 70% Sb 2 O 3 in Nylon 6 - âT/Sâ from M&T Chemicals "N-6 70/30 90% Sb 2 O 3 in polyethylene - M&T Chemical's "T/S" PE90/10 Glass fiber - PPG3540 1/8" Shredded glass fiber "Capron" 8200 - Allied Chemical Nylon 6 âUltranoxâ 626 from BorgWarner Chemical - Bis(2,
4-di-t-butylphenyl)pentaerytol dimer acid sodium empol Obtained by neutralization of dimer acid with sodium hydroxide. Examples 1-3 and Comparative Examples A-D These experiments demonstrate that the difference in concentrate carrier (nylon and polyethylene) is important in compositions containing alkali metal carboxylates and PET. These experiments show that powdered antimony oxide alone (without carrier) causes more significant degradation than antimony oxide in a nylon carrier, similar to antimony oxide in polyethylene. All examples contain 1% antimony oxide, either neat (powder) or in a polymeric carrier. The composition is shown in Table 1, and the properties are shown in Table 2. A comparison of Example 1 and Comparative Example A shows that antimony oxide in polyethylene exhibits lower viscosity and somewhat poorer mechanical properties than antimony trioxide in nylon 6 for the alkali metal carboxylate/PET system. It shows giving. In a similar composition, the use of a nylon carrier (Example 2) provides a substantially higher melt viscosity and better mechanical properties than in powdered antimony trioxide (Comparative Example B), especially after harsh molding cycles. give. In the additional presence of a plasticizer (N-octadecyl p-toluenesulfonamide), antimony trioxide in nylon (Example 3) can be mixed with antimony trioxide in a polyethylene carrier (Comparative Example C) or pure powder (Comparative Example D) provides higher melt viscosity (and therefore less degradation) and superior properties than either of D). The effect is even more dramatic when the bar specimens are molded using a severe molding cycle.
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8.9
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23.0 19.4 21.0 14.8
17.8
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2.24 1.64 2.06 1.46
1.66
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0.65ïŒ
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ãã0.6ïŒ
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žåã¢ã³ãã¢ã³ãå«æãããå®æœ
äŸïŒåã³ïŒãšæ¯èŒäŸïŒ¥ã¯0.2ïŒ
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ã¯ã¹â626ããå«æãããçµæç©äžã®æ®éšã¯PET
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ãæ©æ¢°çæ§è³ªãæããçµæç©ãäžããã[Table] Severe cycle;
Impact value without notch ãã ãã
14.8 9.9 11.0 6.8
8.9
Tensile strength, kpsi ãã ãã
23.0 19.4 21.0 14.8
17.8
Elongation, % ãã ãã
2.24 1.64 2.06 1.46
1.66
Examples 4-10 and Comparative Example E These experiments were carried out using 11.9% brominated polystyrene;
3.2% N-octadecyl p-toluenesulfonamide, 3.5% alkali metal carboxylate used in Examples 1-7 ("Surlyn" 8920),
Contains 0.65% pentaerythritol tetrastearate, 0.6% Epon 1009F, 0.2% Irganox 1010, and 1.0% antimony oxide added as a concentrate in the carrier. Examples 4 and 5 and Comparative Example E also contain 0.2% "Ultranox" 626. The remainder of the composition is PET
It is. Although the effectiveness of various nylon carriers varies, they generally provide compositions with higher melt viscosities and superior mechanical properties than are obtainable with inert polyethylene carriers.
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åãååšããªãããšã瀺ããTABLE Examples 11-14 and Comparative Examples F and G These experiments show that antimony oxide/polyamide concentrates are also effective when the alkali metal carboxylate is sodium dimerate. All experiments contained 1% antimony oxide.
The composition is shown in Table 4 along with the melt viscosity. Examples 11 and 12, along with Comparative Examples F and I,
Demonstrates the effectiveness of Sb 2 O 3 in nylon 6 when compared to Sb 2 O 3 . Comparative Examples G and H show that in the absence of an alkali metal carboxylate, there is no degradation due to antimony oxide.
Claims (1)
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ïŒåã¯ïŒé èšèŒã®æ··åç©ã ïŒ ãã¬ãã圢æ ã«ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èš
èŒã®æ··åç©ã[Scope of Claims] 1 (a) 20 to 90% by weight of the mixture, at least
polyethylene terephthalate having an inherent viscosity of 0.4, (b) from 0.1 to 20% by weight of the mixture of (a) and (b), from 7 to
sodium and at least one carboxyl-containing organic compound selected from the class consisting of hydrocarbon monocarboxylic acids containing 25 carbon atoms, hydrocarbon di- or tricarboxylic acids containing 7 to 54 carbon atoms and organic carboxyl-containing polymers; (c) a halogenated flame retardant consisting of an aromatic organic compound having at least one aromatic ring containing sufficient halogen bonded directly to the aromatic ring carbon to provide flame retardancy; (d) the flame retardant is present in the mixture in an amount sufficient to provide the mixture with halogen in an amount of 5 to 30% by weight based on the weight of the mixture with (a); 0.3-8% antimony oxide by weight of the mixture, said antimony oxide being added to the mixture in the form of a concentrate in polyamide, said concentrate being 20-80% by weight based on the total weight of antimony oxide and polyamide. A polyethylene terephthalate molding mixture containing antimony oxide of . 2. Component (b) is a sodium or potassium salt of an ionic hydrocarbon copolymer present in an amount of 1 to 20% by weight of the mixture with (a).
Mixtures as described in Section. 3 Component (b) is 0.1 to 5% by weight of the mixture with (a)
A mixture according to claim 1, wherein the mixture is a sodium or potassium salt of a hydrocarbon di- or tricarboxylic acid of 7 to 54 carbon atoms present in an amount of . 4. A mixture according to claim 1, containing up to 55% by weight of the mixture of reinforcing or filler materials. 5 The ionic hydrocarbon copolymer of component (b) is 2-
3. A mixture according to claim 2, which is a sodium salt of a copolymer of an alpha-olefin of 5 carbon atoms and an alpha, beta-ethylenically unsaturated carboxylic acid of 3 to 5 carbon atoms. 6 Halogenated flame retardants include decabromodiphenyl ether, octabromodiphenyl ether, ethylene bis-(tetrabromophthalimide), brominated polystyrene, poly(dibromophenylene oxide), decachlorodiphenyl ether, octachlorodiphenyl ether , ethylene bis-(tetrachlorophthalimide), chlorinated polystyrene and poly(dichlorophenylene oxide). 7 Claim 1, which also contains a plasticizer,
The mixture according to item 2 or 3. 8. A mixture according to claim 1 in the form of pellets.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US93538486A | 1986-11-26 | 1986-11-26 | |
US935384 | 1986-11-26 | ||
US941791 | 1986-12-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63137952A JPS63137952A (en) | 1988-06-09 |
JPH0478652B2 true JPH0478652B2 (en) | 1992-12-11 |
Family
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Application Number | Title | Priority Date | Filing Date |
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JP62271965A Granted JPS63137952A (en) | 1986-11-26 | 1987-10-29 | Polyethylene terephthalate molding composition |
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JP (1) | JPS63137952A (en) |
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Publication number | Priority date | Publication date | Assignee | Title |
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JPH0243253A (en) * | 1988-08-03 | 1990-02-13 | Kanegafuchi Chem Ind Co Ltd | Fire resistant polyester resin composition for injection molding |
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1987
- 1987-10-29 JP JP62271965A patent/JPS63137952A/en active Granted
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