JP2001064521A - Flame retardant resin composition - Google Patents
Flame retardant resin compositionInfo
- Publication number
- JP2001064521A JP2001064521A JP24132199A JP24132199A JP2001064521A JP 2001064521 A JP2001064521 A JP 2001064521A JP 24132199 A JP24132199 A JP 24132199A JP 24132199 A JP24132199 A JP 24132199A JP 2001064521 A JP2001064521 A JP 2001064521A
- Authority
- JP
- Japan
- Prior art keywords
- melamine
- flame
- resin
- resin composition
- methylene
- 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.)
- Pending
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 49
- 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 title claims abstract description 39
- 239000011342 resin composition Substances 0.000 title claims abstract description 18
- -1 nitrilotris (methylene) Chemical class 0.000 claims abstract description 50
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 37
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical group NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000002245 particle Substances 0.000 claims abstract description 29
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 25
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 17
- 150000007974 melamines Chemical class 0.000 claims description 15
- 150000002736 metal compounds Chemical class 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 229920000388 Polyphosphate Polymers 0.000 claims description 4
- 239000001205 polyphosphate Substances 0.000 claims description 4
- 235000011176 polyphosphates Nutrition 0.000 claims description 4
- LWFBRHSTNWMMGN-UHFFFAOYSA-N 4-phenylpyrrolidin-1-ium-2-carboxylic acid;chloride Chemical compound Cl.C1NC(C(=O)O)CC1C1=CC=CC=C1 LWFBRHSTNWMMGN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004254 Ammonium phosphate Substances 0.000 claims description 3
- 239000004114 Ammonium polyphosphate Substances 0.000 claims description 3
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims description 3
- 235000019289 ammonium phosphates Nutrition 0.000 claims description 3
- 229920001276 ammonium polyphosphate Polymers 0.000 claims description 3
- 235000019826 ammonium polyphosphate Nutrition 0.000 claims description 3
- CEDDGDWODCGBFQ-UHFFFAOYSA-N carbamimidoylazanium;hydron;phosphate Chemical compound NC(N)=N.OP(O)(O)=O CEDDGDWODCGBFQ-UHFFFAOYSA-N 0.000 claims description 3
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 3
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 claims description 3
- MIPARUODWSCDNS-UHFFFAOYSA-N OP(O)=O.NC1=NC(N)=NC(N)=N1 Chemical compound OP(O)=O.NC1=NC(N)=NC(N)=N1 MIPARUODWSCDNS-UHFFFAOYSA-N 0.000 abstract description 5
- 229910044991 metal oxide Inorganic materials 0.000 abstract description 2
- 150000004706 metal oxides Chemical class 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 description 45
- 239000011347 resin Substances 0.000 description 45
- 239000013078 crystal Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 6
- 238000002485 combustion reaction Methods 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- 229920006380 polyphenylene oxide Polymers 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 239000000347 magnesium hydroxide Substances 0.000 description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000008399 tap water Substances 0.000 description 4
- 235000020679 tap water Nutrition 0.000 description 4
- 229920005992 thermoplastic resin Polymers 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- NYYLZXREFNYPKB-UHFFFAOYSA-N 1-[ethoxy(methyl)phosphoryl]oxyethane Chemical compound CCOP(C)(=O)OCC NYYLZXREFNYPKB-UHFFFAOYSA-N 0.000 description 1
- IVORCBKUUYGUOL-UHFFFAOYSA-N 1-ethynyl-2,4-dimethoxybenzene Chemical compound COC1=CC=C(C#C)C(OC)=C1 IVORCBKUUYGUOL-UHFFFAOYSA-N 0.000 description 1
- OHASXDUBONILDR-UHFFFAOYSA-N 2,3-dimethylbutylphosphonic acid Chemical compound CC(C)C(C)CP(O)(O)=O OHASXDUBONILDR-UHFFFAOYSA-N 0.000 description 1
- QLVPICNVQBBOQP-UHFFFAOYSA-N 2-(4,6-diamino-1,3,5-triazin-2-yl)guanidine Chemical compound NC(N)=NC1=NC(N)=NC(N)=N1 QLVPICNVQBBOQP-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- HAEFDDOAYBQRGK-UHFFFAOYSA-N 2-methylpropylphosphonic acid Chemical compound CC(C)CP(O)(O)=O HAEFDDOAYBQRGK-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- LKMHPSIHLUJMAR-UHFFFAOYSA-N C(CCC)OP1(=O)OC(C(C)O1)(O)O Chemical compound C(CCC)OP1(=O)OC(C(C)O1)(O)O LKMHPSIHLUJMAR-UHFFFAOYSA-N 0.000 description 1
- AXKPBIUQVYVDHP-UHFFFAOYSA-N CCc1cccc(c1CC)P(O)=O Chemical compound CCc1cccc(c1CC)P(O)=O AXKPBIUQVYVDHP-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 241000219112 Cucumis Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- KIGXMYYGQYMICF-UHFFFAOYSA-N Diphenylphosphine Acid Chemical compound C=1C=CC=CC=1P(=O)(CCCCC(=O)O)C1=CC=CC=C1 KIGXMYYGQYMICF-UHFFFAOYSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004902 Softening Agent Substances 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
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- OJMOMXZKOWKUTA-UHFFFAOYSA-N aluminum;borate Chemical compound [Al+3].[O-]B([O-])[O-] OJMOMXZKOWKUTA-UHFFFAOYSA-N 0.000 description 1
- VCNTUJWBXWAWEJ-UHFFFAOYSA-J aluminum;sodium;dicarbonate Chemical compound [Na+].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O VCNTUJWBXWAWEJ-UHFFFAOYSA-J 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- QBLDFAIABQKINO-UHFFFAOYSA-N barium borate Chemical compound [Ba+2].[O-]B=O.[O-]B=O QBLDFAIABQKINO-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BFPBWJGVRNQWEK-UHFFFAOYSA-N bis(4-methoxyphenyl)phosphinic acid Chemical compound C1=CC(OC)=CC=C1P(O)(=O)C1=CC=C(OC)C=C1 BFPBWJGVRNQWEK-UHFFFAOYSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- KUKLSWLXUCSXIB-UHFFFAOYSA-N but-1-ene;prop-2-enoic acid Chemical compound CCC=C.OC(=O)C=C KUKLSWLXUCSXIB-UHFFFAOYSA-N 0.000 description 1
- UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- 150000007973 cyanuric acids Chemical class 0.000 description 1
- 229910001647 dawsonite Inorganic materials 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- KTLIMPGQZDZPSB-UHFFFAOYSA-N diethylphosphinic acid Chemical compound CCP(O)(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
- GOJNABIZVJCYFL-UHFFFAOYSA-N dimethylphosphinic acid Chemical compound CP(C)(O)=O GOJNABIZVJCYFL-UHFFFAOYSA-N 0.000 description 1
- HAKMAMKAFTZXOZ-UHFFFAOYSA-N dioctoxyphosphorylbenzene Chemical compound CCCCCCCCOP(=O)(OCCCCCCCC)C1=CC=CC=C1 HAKMAMKAFTZXOZ-UHFFFAOYSA-N 0.000 description 1
- YTMRJBAHYSIRMZ-UHFFFAOYSA-N dioctylphosphinic acid Chemical compound CCCCCCCCP(O)(=O)CCCCCCCC YTMRJBAHYSIRMZ-UHFFFAOYSA-N 0.000 description 1
- 150000002013 dioxins Chemical class 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- YHWFKFZHFKIWRB-UHFFFAOYSA-L disodium 2-oxido-1,3,2lambda5-dioxaphospholane 2-oxide Chemical compound [Na+].[Na+].[O-]P1(=O)OCCO1.[O-]P1(=O)OCCO1 YHWFKFZHFKIWRB-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- ZSFDBVJMDCMTBM-UHFFFAOYSA-N ethane-1,2-diamine;phosphoric acid Chemical compound NCCN.OP(O)(O)=O ZSFDBVJMDCMTBM-UHFFFAOYSA-N 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- NXHKQBCTZHECQF-UHFFFAOYSA-N ethyl(methyl)phosphinic acid Chemical compound CCP(C)(O)=O NXHKQBCTZHECQF-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000007706 flame test Methods 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 239000007849 furan resin Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical compound NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- SZTJCIYEOQYVED-UHFFFAOYSA-N methyl(propyl)phosphinic acid Chemical compound CCCP(C)(O)=O SZTJCIYEOQYVED-UHFFFAOYSA-N 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- UEUYWKCOFGPNPV-UHFFFAOYSA-N methylphosphonic acid;1,3,5-triazine-2,4,6-triamine Chemical compound CP(O)(O)=O.NC1=NC(N)=NC(N)=N1 UEUYWKCOFGPNPV-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 229920003986 novolac Polymers 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
- NJGCRMAPOWGWMW-UHFFFAOYSA-N octylphosphonic acid Chemical compound CCCCCCCCP(O)(O)=O NJGCRMAPOWGWMW-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- UOURRHZRLGCVDA-UHFFFAOYSA-D pentazinc;dicarbonate;hexahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[O-]C([O-])=O.[O-]C([O-])=O UOURRHZRLGCVDA-UHFFFAOYSA-D 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 1
- 229920001523 phosphate polymer Polymers 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000002455 scale inhibitor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- LTURHSAEWJPFAA-UHFFFAOYSA-N sulfuric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OS(O)(=O)=O.NC1=NC(N)=NC(N)=N1 LTURHSAEWJPFAA-UHFFFAOYSA-N 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- OGDSVONAYZTTDA-UHFFFAOYSA-N tert-butylphosphonic acid Chemical compound CC(C)(C)P(O)(O)=O OGDSVONAYZTTDA-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical group O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- 229940077935 zinc phosphate Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
(57)【要約】
【課題】 優れた難燃性を有する樹脂組成物を提供す
る。
【解決手段】 平均粒子径が20μm以下の下記一般式
(1)で示されるニトリロトリス(メチレン)ホスホン
酸メラミン塩を含有する難燃性樹脂組成物。更に水和金
属酸化物を含有するのが好ましい。
【化1】
(式中、Mはメラミンを表し、nは2〜5の整数を表
す。)(57) [Problem] To provide a resin composition having excellent flame retardancy. SOLUTION: The flame-retardant resin composition contains a nitrilotris (methylene) phosphonic acid melamine salt represented by the following general formula (1) having an average particle diameter of 20 μm or less. Further, it preferably contains a hydrated metal oxide. Embedded image (In the formula, M represents melamine, and n represents an integer of 2 to 5.)
Description
【0001】[0001]
【発明の属する技術分野】本発明は、各種樹脂に対し
て、分散性がよく、かつ優れた難燃性を付与することが
できる低発煙性のノンハロゲン系難燃剤を含有する難燃
性樹脂組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a flame-retardant resin composition containing a low-smoke non-halogen flame-retardant, which can impart excellent flame retardancy to various resins. About things.
【0002】[0002]
【従来の技術】従来、プラスチックの難燃剤として、塩
素、臭素などのハロゲン化物、リン系化合物、チッソ系
化合物、あるいはアンチモン、ホウ素系の無機化合物が
使用されたきた。2. Description of the Related Art Conventionally, halides such as chlorine and bromine, phosphorus compounds, nitrogen compounds, or antimony and boron inorganic compounds have been used as flame retardants for plastics.
【0003】しかしながら、近年、あらゆる分野で難燃
性のレベルが厳しくなり、高い難燃性能が要求されると
共に、特に臭素、塩素を含む難燃剤は燃焼の際に微量な
がら人体に有毒なダイオキシン類が発生する可能性が指
摘され、ノンハロゲン系の難燃剤への要望が高まってい
る。[0003] However, in recent years, the level of flame retardancy has become severe in all fields, and high flame retardancy has been demanded. In addition, flame retardants containing bromine and chlorine are dioxins which are toxic to the human body in trace amounts during combustion. It has been pointed out that there is a possibility of occurrence of flammability, and demands for non-halogen flame retardants are increasing.
【0004】ノンハロゲン系の難燃剤としては、例え
ば、硬化性樹脂に対して赤りんを配合した樹脂組成物
(特公昭59−49942号公報)、エポキシ樹脂の難
燃剤として水和アルミナ(特開平05−25369号公
報)、表面処理した赤りん、水和アルミナ、シリカ粉末
(特開昭58−198521号公報)、改質赤りん(特
開昭63−156860号公報)、フェノール樹脂に対
してホウ酸カルシウムと水酸化アルミニウムまたは水酸
化マグネシウム(特開平05−43774号公報)、フ
ェノール樹脂に対してホウ酸と三酸化アンチモン(特開
昭60−81244号公報)、ポリウレタン樹脂に対し
て分子内に3つのトリアジン構造を有する化合物(特開
昭53−21241号公報)等が提案されている。Examples of the non-halogen flame retardant include a resin composition in which red phosphorus is blended with a curable resin (Japanese Patent Publication No. 59-49942), and hydrated alumina as an epoxy resin flame retardant (Japanese Patent Laid-Open No. No. 25369), surface-treated red phosphorus, hydrated alumina, silica powder (JP-A-58-198521), modified red phosphorus (JP-A-63-156860), and a phenol resin. Calcium oxide and aluminum hydroxide or magnesium hydroxide (JP-A-05-43774), boric acid and antimony trioxide (JP-A-60-81244) for phenolic resin, and intramolecular for polyurethane resin. A compound having three triazine structures (JP-A-53-21241) and the like have been proposed.
【0005】一方、熱可塑性樹脂に対しては、ポリアミ
ド樹脂用として水酸化マグネシウム(特開昭54−83
952号公報及び特開昭54−131645号公報)、
及びメラミンシアヌレート(特開昭53−31759号
公報、特開昭54−91558号公報)、ポリカーボネ
ート用として有機スルホン酸塩(特開昭50−9853
9号公報、特開昭50−98540号)、スルフィド酸
塩(特公平01−22304号公報)、ポリフェニレン
オキシド用としてホスホネート化合物とポリリン酸アン
モニウム(特開昭52−86449号公報)、ホスフェ
ート化合物と三酸化アンチモン(特開昭49−3294
7号公報)、ポリエステル用としてポリホスホネート
(米国特許第3719727号)等の難燃剤が提案され
ている。On the other hand, for a thermoplastic resin, magnesium hydroxide (Japanese Patent Application Laid-Open No. 54-83) is used for a polyamide resin.
952 and JP-A-54-131645),
And melamine cyanurate (JP-A-53-31759, JP-A-54-91558) and organic sulfonates for polycarbonate (JP-A-50-9853).
No. 9, JP-A-50-98540), sulfide salts (JP-B No. 01-22304), phosphonate compounds and polyphosphates for polyphenylene oxide (JP-A-52-86449), phosphate compounds. Antimony trioxide (JP-A-49-3294)
No. 7) and flame retardants such as polyphosphonates (US Pat. No. 3,719,727) for polyesters have been proposed.
【0006】しかしながら、上記の難燃剤の中で、赤り
んは赤褐色であるため、赤りんによって樹脂が着色して
しまいカラーリングが不可能となる。また、樹脂の熱加
工あるいは焼却の際にホスフィンガスの発生のため作業
環境を悪化させ、これを抑制するために赤りんを被覆剤
により被覆したりしているが、ホスフィンガスの発生を
完全には抑制することができない。However, among the above flame retardants, red phosphorus is reddish brown, so that the resin is colored by the red phosphorus and coloring is impossible. In addition, the working environment is deteriorated due to the generation of phosphine gas during thermal processing or incineration of the resin, and red phosphorus is coated with a coating agent to suppress this, but the generation of phosphine gas is completely prevented. Cannot be suppressed.
【0007】[0007]
【発明が解決しようとする課題】有機リン系難燃剤はノ
ンハロゲン系の難燃剤として、特に注目されている。そ
の難燃機構は、揮発性が高いものは、加熱によって気化
したリン化合物が気相における燃焼の抑制剤として、酸
素ガスの希釈効果、揮発による燃焼系の冷却効果、燃焼
の化学反応の抑制効果などによってプラスチックの燃焼
を抑制する。一方、揮発性が低いものは、加熱により熱
分解してリン酸を生成し、これがメタリン酸、ポリメタ
リン酸となって、焼成するプラスチックの固相または溶
融層面に不揮発性のリン酸ポリマーを形成する。また、
リン酸の脱水反応によりプラスチックを炭化させて炭化
層を形成し、それによって空気の進入を遮断し、外部か
らの熱エネルギーの供給を遮断して燃焼を抑制する。SUMMARY OF THE INVENTION Organophosphorus flame retardants have received particular attention as non-halogen flame retardants. The flame-retardant mechanism has a high volatility, and the phosphorus compound vaporized by heating acts as an inhibitor of combustion in the gas phase as a diluent for oxygen gas, a cooling effect for the combustion system due to volatilization, and an effect for suppressing the chemical reaction of combustion. By such means, the combustion of plastic is suppressed. On the other hand, those with low volatility generate thermal decomposition by heating to generate phosphoric acid, which becomes metaphosphoric acid and polymetaphosphoric acid, and forms a non-volatile phosphate polymer on the solid phase or molten layer surface of the plastic to be fired. . Also,
The plastic is carbonized by a dehydration reaction of phosphoric acid to form a carbonized layer, whereby the intrusion of air is blocked, and the supply of heat energy from the outside is blocked to suppress combustion.
【0008】現在、有機リン系難燃剤は、リン酸エステ
ル、ホスファイト系が各種提案されているものの、その
多くは水溶性のため樹脂に対する親和性が低く、また化
合物中のP含有量が低いため、難燃効果を高めるために
は多量に樹脂中に含有させなければならず、機械的物性
が損なわれる。At present, various types of organophosphorus flame retardants have been proposed, such as phosphoric acid esters and phosphites. However, most of them have low affinity for resins due to their water solubility and low P content in the compounds. Therefore, in order to enhance the flame-retardant effect, a large amount must be contained in the resin, and the mechanical properties are impaired.
【0009】ニトリロトリス(メチレン)ホスホン酸及
びその誘導体は、スケール防止剤、防食剤、金属表面処
理剤、キレート剤として各種分野で用いられ、また、特
開平05−4997号公報には、ニトリロトリス(メチ
レン)ホスホン酸の6メラミン塩が優れた難燃性化合物
であることが開示されている。しかしながら、ポリフェ
ニレンオキサイド樹脂(PPO)に対して、UL94H
Bレベルの難燃性試験にかろうじて合格するものの、実
用的な難燃レベルに達していないだけでなく、その他の
樹脂に対しては、難燃効果がほとんど得られていない。[0009] Nitrilotris (methylene) phosphonic acid and its derivatives are used in various fields as scale inhibitors, anticorrosives, metal surface treatment agents and chelating agents, and Japanese Patent Application Laid-Open No. 05-4997 discloses that nitrilotris. It is disclosed that 6 melamine salts of (methylene) phosphonic acid are excellent flame retardant compounds. However, with respect to polyphenylene oxide resin (PPO), UL94H
Although it barely passes the B-level flame retardancy test, it has not yet reached a practical flame retardancy level, and has little flame-retardant effect on other resins.
【0010】本発明者らは、前記課題に鑑み、ノンハロ
ゲン系の難燃剤について鋭意研究を重ねた結果、P含有
量の高いニトリロトリス(メチレン)ホスホン酸に着目
し、先に、各種樹脂に対して優れた難燃性を付与するこ
とができるニトリロトリス(メチレン)ホスホン酸のメ
ラミン塩を出願した(特願平10−251779号公
報)。In view of the above problems, the present inventors have conducted intensive studies on non-halogen flame retardants, and as a result, focused on nitrile tris (methylene) phosphonic acid having a high P content. An application was made for a melamine salt of nitrilotris (methylene) phosphonic acid capable of imparting excellent flame retardancy (Japanese Patent Application No. 10-251779).
【0011】更に、かかるニトリロトリス(メチレン)
ホスホン酸のメラミン塩について鋭意研究を重ねたとこ
ろ、特定範囲の粒子径を有するものが、樹脂に対する分
散性がよく、更に難燃効果が高まることを知見し、本発
明を完成するに至った。即ち、本発明は優れた難燃性を
有する樹脂組成物を提供することを目的とする。Further, such nitrilotris (methylene)
After intensive studies on the melamine salts of phosphonic acids, they have found that those having a particle size in a specific range have good dispersibility in resins and further enhance the flame retardant effect, and have completed the present invention. That is, an object of the present invention is to provide a resin composition having excellent flame retardancy.
【0012】[0012]
【課題を解決するための手段】本発明が提供しようとす
る難燃性樹脂組成物は、平均粒子径が20μm以下の下
記一般式(1)Means for Solving the Problems The flame-retardant resin composition to be provided by the present invention has the following general formula (1) having an average particle diameter of 20 μm or less.
【0013】[0013]
【化2】 Embedded image
【0014】(式中、Mはメラミンを表し、nは2〜5
の整数を表す。)で示されるニトリロトリス(メチレ
ン)ホスホン酸メラミン塩を含有することを構成上の特
徴とする。(Wherein, M represents melamine, and n represents 2 to 5)
Represents an integer. ), Which is characterized by containing a melamine salt of nitrilotris (methylene) phosphonic acid represented by the following formula:
【0015】該難燃性樹脂組成物は、上記の一般式
(1)で示されるニトリロトリス(メチレン)ホスホン
酸メラミン塩と水和金属化合物とを含有することが好ま
しい。It is preferable that the flame-retardant resin composition contains a melamine nitrilotris (methylene) phosphonate represented by the above general formula (1) and a hydrated metal compound.
【0016】[0016]
【発明の実施の形態】以下、本発明を詳細に説明する。
本発明の難燃性樹脂組成物は、平均粒子径が20μm以
下の範囲の下記一般式(1)で示されるニトリロトリス
(メチレン)ホスホン酸メラミン塩を有効成分として含
有するものである。BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The flame-retardant resin composition of the present invention contains a melamine nitrilotris (methylene) phosphonate represented by the following general formula (1) having an average particle diameter of 20 μm or less as an active ingredient.
【0017】[0017]
【化3】 Embedded image
【0018】前記一般式(1)で表わされるニトリロト
リス(メチレン)ホスホン酸メラミン塩の式中、nは2
〜5で、好ましくはnは3〜4である。In the formula of the nitrilotris (methylene) phosphonic acid melamine salt represented by the general formula (1), n is 2
-5, preferably n is 3-4.
【0019】かかるニトリロトリス(メチレン)ホスホ
ン酸メラミン塩の製造方法としては、特に限定はなく、
公知の方法を用いることができる。例えば、下記一般式
(2)The method for producing the melamine salt of nitrilotris (methylene) phosphonic acid is not particularly limited.
A known method can be used. For example, the following general formula (2)
【0020】[0020]
【化4】 Embedded image
【0021】で示されるニトリロトリス(メチレン)ホ
スホン酸とメラミンとを水、水−アセトンの混合溶媒、
水−アルコール等の水系溶媒中で80℃以上の温度で反
応させればよい。Nitrilotris (methylene) phosphonic acid and melamine represented by the following formula: water, a mixed solvent of water-acetone,
The reaction may be performed at a temperature of 80 ° C. or more in an aqueous solvent such as water-alcohol.
【0022】上記の反応の目的物のニトリロトリス(メ
チレン)ホスホン酸メラミン塩を得る反応において、原
料の一般式(2)で示されるニトリロトリス(メチレ
ン)ホスホン酸とメラミンとの配合割合は、通常一般式
(2)のホスホン酸1モルに対してメラミン2〜5モル
の範囲であり、その範囲内において目的物に導入される
メラミンの量、例えば2〜5個のメラミン量により、メ
ラミン量の使用量を適宜調整すればよい。反応終了後、
ろ過、乾燥して、所望の粒子径のものが得られるまで粉
砕処理して製品とする。In the above reaction for obtaining the target melamine salt of nitrilotris (methylene) phosphonic acid, the compounding ratio of the starting materials nitrilotris (methylene) phosphonic acid represented by the general formula (2) to melamine is usually The amount of melamine is 2 to 5 mol per mol of the phosphonic acid of the general formula (2), and the amount of melamine introduced into the target substance within the range, for example, the amount of melamine of 2 to 5 melamine, The amount used may be adjusted as appropriate. After the reaction,
Filtration and drying are performed, and pulverization is performed until a product having a desired particle size is obtained to obtain a product.
【0023】一般式(1)で示されるニトリロトリス
(メチレン)ホスホン酸メラミン塩の具体例としては、 ニトリロトリス(メチレン)ホスホン酸・5メラミン塩 ニトリロトリス(メチレン)ホスホン酸・4メラミン塩 ニトリロトリス(メチレン)ホスホン酸・3メラミン塩 ニトリロトリス(メチレン)ホスホン酸・2メラミン塩 等が挙げられる。前記した、ニトリロトリス(メチレ
ン)ホスホン酸メラミン塩は1種又は2種以上で用いら
れる。Specific examples of the nitrilotris (methylene) phosphonic acid melamine salt represented by the general formula (1) include: nitrilotris (methylene) phosphonic acid / 5 melamine salt nitrilotris (methylene) phosphonic acid / 4 melamine salt nitrilotris (Methylene) phosphonic acid / 3 melamine salt Nitrilotris (methylene) phosphonic acid / 2 melamine salt and the like. The above-mentioned melamine salt of nitrilotris (methylene) phosphonic acid is used alone or in combination of two or more.
【0024】更に、本発明において、ニトリロトリス
(メチレン)ホスホン酸メラミン塩は、平均粒子径が2
0μm以下の範囲のものを用いることが重要な要件とな
る。この理由は、平均粒子径が20μmより大きくなる
と樹脂に対する分散性が悪くなって、樹脂成形品に安定
した難燃性が付与できなくなる傾向があり、また1μm
より小さくなると、粉砕装置等の問題から実用的でない
ため本発明では、平均粒子径1〜10μmの範囲のもの
が好ましく用いられる。In the present invention, the melamine nitrilotris (methylene) phosphonate has an average particle size of 2%.
An important requirement is to use one having a range of 0 μm or less. The reason for this is that if the average particle diameter is larger than 20 μm, the dispersibility in the resin becomes poor, and it tends to be impossible to impart stable flame retardancy to the resin molded product.
If the particle size is smaller, it is not practical due to the problem of the pulverizing device or the like.
【0025】なお、平均粒子径はレーザー散乱式粒度測
定装置(マイクロトラック)により求めた値を示す。The average particle size is a value determined by a laser scattering type particle size measuring device (Microtrack).
【0026】前記したニトリロトリス(メチレン)ホス
ホン酸メラミン塩の各種樹脂に対する配合割合は、樹脂
100重量部に対して、Pとして、0.5〜30重量
部、好ましくは1〜10重量部である。この理由は、配
合割合が0.5重量部より小さくなると、十分な難燃効
果が得られにくく、一方、30重量部より大きくなると
難燃効果は大きくなるが成型品の機械的物性が低下する
傾向があるので好ましくない。The compounding ratio of the above-mentioned melamine nitrilotris (methylene) phosphonate to various resins is 0.5 to 30 parts by weight, preferably 1 to 10 parts by weight, based on 100 parts by weight of the resin. . The reason is that if the mixing ratio is less than 0.5 part by weight, it is difficult to obtain a sufficient flame retardant effect, while if it is more than 30 parts by weight, the flame retardant effect becomes large, but the mechanical properties of the molded product deteriorate. It is not preferable because there is a tendency.
【0027】本発明に用いることができる樹脂として
は、特に限定はなく、例えば、エポキシ樹脂、フェノー
ル樹脂、ポリウレタン樹脂、メラミン樹脂、ユリア樹
脂、アニリン樹脂、フラン樹脂、アルキド樹脂、キシレ
ン樹脂、不飽和ポリエステル樹脂、ジアリールフタレー
ト樹脂等の硬化性樹脂、ポリブチレンテレフタレート樹
脂、ポリエチレンテレフタレート樹脂、ポリカーボネー
ト、ポリフェニレンオキシド、ポリフェニレンエーテ
ル、ナイロン6、ナイロン66、ナイロン12、ポリア
セタール、ポリエチレン、ポリプロピレン、ポリブタジ
エン、ポリアクリロニトリル、ポリスチレン、ポリメチ
ルメタクリレート、ポリエチレンオキシド、ポリテトラ
メチレンオキシド、熱可塑性ポリウレタン、フェノキシ
樹脂、ポリアミド、エチレン/プロピレン共重合体、エ
チレン/1−ブテン共重合体、エチレン/プロピレン/
非共役ジエン共重合体、エチレン/アクリル酸エチル共
重合体、エチレン/メタクリル酸グリシジル共重合体、
エチレン/酢酸ビニル/メタクリル酸グリシジル共重合
体、エチレン/プロピレン−g−無水マレイン酸共重合
体、ポリエステルポリエーテルエラストマー、ポリテト
ラフルオロエチレン及びこれらの変性物等の熱可塑性樹
脂が挙げられる。これら樹脂は、ホモポリマーであって
もコポリマーであってもよく、2種類以上の混合物であ
ってもよい。The resin that can be used in the present invention is not particularly limited. For example, epoxy resin, phenol resin, polyurethane resin, melamine resin, urea resin, aniline resin, furan resin, alkyd resin, xylene resin, unsaturated resin Curable resin such as polyester resin and diaryl phthalate resin, polybutylene terephthalate resin, polyethylene terephthalate resin, polycarbonate, polyphenylene oxide, polyphenylene ether, nylon 6, nylon 66, nylon 12, polyacetal, polyethylene, polypropylene, polybutadiene, polyacrylonitrile, polystyrene , Polymethyl methacrylate, polyethylene oxide, polytetramethylene oxide, thermoplastic polyurethane, phenoxy resin, polyamide, ethylene On / propylene copolymer, ethylene / 1-butene copolymer, ethylene / propylene /
Non-conjugated diene copolymer, ethylene / ethyl acrylate copolymer, ethylene / glycidyl methacrylate copolymer,
Thermoplastic resins such as ethylene / vinyl acetate / glycidyl methacrylate copolymer, ethylene / propylene-g-maleic anhydride copolymer, polyester polyether elastomer, polytetrafluoroethylene, and modified products thereof are exemplified. These resins may be homopolymers or copolymers, or may be a mixture of two or more.
【0028】ここで、硬化性樹脂とは、熱、触媒、ある
いは紫外線などの作用により化学変化をおこして架橋構
造が発達し、分子量が増大して三次元網状構造を有し
て、硬化して半永久的に不溶性・不融性となる合成樹脂
を示す。また、熱可塑性樹脂とは、加熱により流動性を
示し、これにより賦形が可能である樹脂のことを表す。Here, the curable resin is a resin having a three-dimensional network structure with an increased molecular weight due to a chemical change caused by the action of heat, a catalyst, ultraviolet rays, or the like. This shows a synthetic resin that becomes semi-permanently insoluble and infusible. In addition, the thermoplastic resin indicates a resin that exhibits fluidity by heating and can be shaped thereby.
【0029】本発明の難燃性樹脂組成物において、更
に、水和金属化合物と併用することにより更に難燃効果
を高めることができる。水和金属化合物としては、吸熱
反応による燃焼抑制作用のあるMmOn・XH2O(Mは
金属、m、nは金属の原子価によって定まる1以上の整
数、Xは含有結晶水を示す。)で表わされる化合物また
は該化合物を含む複塩であり、具体的には、水酸化カル
シウム、水酸化マグネシウム、塩基性炭酸マグネシウ
ム、水酸化カルシウム、水酸化バリウム、水酸化ジルコ
ニウム、ドーソナイト、スズ酸亜鉛、ホウ酸亜鉛、ホウ
酸アルミニウム、五酸化アンチモン、塩基性炭酸亜鉛、
酸化コバルト、酸化ジルコニウム、酸化スズ、酸化アル
ミニウム、酸化チタン、酸化マグネシウム、珪酸カルシ
ウム、ホウ砂、モリブデン酸亜鉛、リン酸亜鉛、リン酸
マグネシウム、ハイドロタルサイト、ハイドロカルマイ
ト、カオリン、タルク、セリサイト、パイロフィライ
ト、ベントナイト、カオリナイト、硫酸カルシウム、硫
酸亜鉛等の1種又は2種以上が挙げられる。また、これ
らの水和金属化合物は、表面処理されていてもよく、こ
れらの水和金属化合物の平均粒子径は、通常20μm以
下、好ましくは、1〜10μmの範囲のものが好まし
い。In the flame-retardant resin composition of the present invention, the flame-retardant effect can be further enhanced by using it in combination with a hydrated metal compound. The hydrated metal compound, the M m O n · XH 2 O (M with a burn suppressing action by endothermic reaction shown metals, m, n is an integer of 1 or more determined by the valency of the metal, X a is-containing crystal water Or a double salt containing the compound, specifically, calcium hydroxide, magnesium hydroxide, basic magnesium carbonate, calcium hydroxide, barium hydroxide, zirconium hydroxide, dawsonite, stannic acid Zinc, zinc borate, aluminum borate, antimony pentoxide, basic zinc carbonate,
Cobalt oxide, zirconium oxide, tin oxide, aluminum oxide, titanium oxide, magnesium oxide, calcium silicate, borax, zinc molybdate, zinc phosphate, magnesium phosphate, hydrotalcite, hydrocalumite, kaolin, talc, sericite , Pyrophyllite, bentonite, kaolinite, calcium sulfate, zinc sulfate and the like. These hydrated metal compounds may be surface-treated, and the average particle size of these hydrated metal compounds is usually 20 μm or less, preferably 1 to 10 μm.
【0030】水和金属化合物の配合割合は、樹脂100
重量部に対して、通常1〜200重量部、好ましくは1
0〜100重量部である。The mixing ratio of the hydrated metal compound is 100
1 to 200 parts by weight, preferably 1 part by weight,
0 to 100 parts by weight.
【0031】また、本発明の難燃性樹脂組成物におい
て、更に、難燃助剤を併用するができる。難燃助剤とし
ては、例えば、三酸化アンチモン、酸化銅、酸化マグネ
シウム、酸化亜鉛、酸化モリブデン、酸化鉄、酸化マン
ガン、酸化アルミニウム、酸化スズ、酸化チタン、酸化
ニッケル等の金属酸化物、炭酸カルシウム、炭酸バリウ
ム等の炭酸塩、メタホウ酸亜鉛、メタホウ酸バリウム等
のメタホウ酸塩、メラミン、メラミンシアヌレート、、
メチロール化メラミン、(イソ)シアヌール酸、メラ
ム、メレム、メロン、サクシノグアミン、硫酸メラミ
ン、硫酸アセトグアナミン、硫酸メラム、硫酸グアニル
メラミン、メラミン樹脂、BTレジン、シアヌール酸、
イソシアネール酸、イソシアヌール酸誘導体、メラミン
イソシアヌレート、ベンゾグアナミン、アセトグアナミ
ン等のメラミン誘導体、グアニジン系化合物、シリコー
ン系化合物、リン系難燃剤から選ばれた1種又は2種以
上が挙げられ、これらの中、特に好ましくはリン系難燃
剤である。Further, in the flame-retardant resin composition of the present invention, a flame-retardant auxiliary can be used in combination. Examples of the flame retardant aid include metal oxides such as antimony trioxide, copper oxide, magnesium oxide, zinc oxide, molybdenum oxide, iron oxide, manganese oxide, aluminum oxide, tin oxide, titanium oxide, nickel oxide, and calcium carbonate. , Carbonates such as barium carbonate, zinc metaborate, metaborates such as barium metaborate, melamine, melamine cyanurate,
Methylolated melamine, (iso) cyanuric acid, melam, melem, melon, succinogamine, melamine sulfate, acetoguanamine sulfate, melam sulfate, guanylmelamine sulfate, melamine resin, BT resin, cyanuric acid,
Isocyanic acid, isocyanuric acid derivatives, melamine isocyanurate, benzoguanamine, melamine derivatives such as acetoguanamine, guanidine compounds, silicone compounds, one or more selected from phosphorus-based flame retardants, and the like. Among them, phosphorus-based flame retardants are particularly preferred.
【0032】リン系難燃剤としては、例えば、リン酸ト
リエチル、リン酸トリクレジル、リン酸トリフェニル、
リン酸クレジルフェニル、リン酸オクチルジフェニル、
ジエチレンリン酸エチルエステル、ジヒドロキシプロピ
レンリン酸ブチルエステル、エチレンリン酸ジナトリウ
ムエステル、メチルホスホン酸、メチルホスホン酸ジメ
チル、メチルホスホン酸ジエチル、エチルホスホン酸、
プロピルホスホン酸、ブチルホスホン酸、2−メチル―
プロピルホスホン酸、t−ブチルホスホン酸、2,3−
ジメチルブチルホスホン酸、オクチルホスホン酸、フェ
ニルホスホン酸、ジオクチルフェニルホスホネート、ジ
メチルホスフィン酸、メチルエチルホスフィン酸、メチ
ルプロピルホスフィン酸、ジエチルホスフィン酸、ジオ
クチルホスフィン酸、フェニルホスフィン酸、ジエチル
フェニルホスフィン酸、ジフェニルホスフィン酸、ビス
(4−メトキシフェニル)ホスフィン酸、赤燐、リン酸
アンモニウム、ポリリン酸アンモニウム、リン酸メラミ
ン、リン酸グアニル尿素、ポリリン酸メラミン、リン酸
グアニジン、エチレンジアミンリン酸塩、ホスファゼ
ン、メチルホスホン酸メラミン塩から選ばれた1種又は
2種以上が挙げられる。これらの中、赤燐、リン酸アン
モニウム、ポリリン酸アンモニウム、リン酸メラミン、
リン酸グアニル尿素、ポリリン酸メラミン、リン酸グア
ニジンが好ましく用いられる。Examples of the phosphorus-based flame retardant include triethyl phosphate, tricresyl phosphate, triphenyl phosphate,
Cresyl phenyl phosphate, octyl diphenyl phosphate,
Ethyl diethylene phosphate, butyl dihydroxypropylene phosphate, disodium ethylene phosphate, methylphosphonic acid, dimethyl methylphosphonate, diethyl methylphosphonate, ethylphosphonic acid,
Propylphosphonic acid, butylphosphonic acid, 2-methyl-
Propylphosphonic acid, t-butylphosphonic acid, 2,3-
Dimethylbutylphosphonic acid, octylphosphonic acid, phenylphosphonic acid, dioctylphenylphosphonate, dimethylphosphinic acid, methylethylphosphinic acid, methylpropylphosphinic acid, diethylphosphinic acid, dioctylphosphinic acid, phenylphosphinic acid, diethylphenylphosphinic acid, diphenylphosphine Acid, bis (4-methoxyphenyl) phosphinic acid, red phosphorus, ammonium phosphate, ammonium polyphosphate, melamine phosphate, guanylurea phosphate, melamine polyphosphate, guanidine phosphate, ethylenediamine phosphate, phosphazene, melamine methylphosphonate One or more selected from salts are mentioned. Among these, red phosphorus, ammonium phosphate, ammonium polyphosphate, melamine phosphate,
Guanylurea phosphate, melamine polyphosphate, and guanidine phosphate are preferably used.
【0033】赤燐は、有機物又は/及び無機物で表面を
改質したものが好ましく、例えば、フェノール樹脂、エ
ポキシ樹脂、エチレン−酢酸ビニル共重合体、メラミン
−ホルムアルデヒド重縮合物、Mg、Ca、Ti、A
l、Co及びZrの水酸化物及びこれらの酸化物から選
ばれた1種又は2種以上で表面処理されたものが、挙げ
られるが、これらに限定されるものではない。Red phosphorus whose surface is modified by an organic substance and / or an inorganic substance is preferable. For example, phenol resin, epoxy resin, ethylene-vinyl acetate copolymer, melamine-formaldehyde polycondensate, Mg, Ca, Ti , A
Examples thereof include, but are not limited to, hydroxides of l, Co, and Zr and those surface-treated with one or more selected from these oxides.
【0034】これら難燃助剤の配合割合は、樹脂100
重量部に対して、通常0.1〜10重量部、好ましくは
0.5〜5重量部である。The mixing ratio of these flame retardant aids is 100
It is usually 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight with respect to parts by weight.
【0035】また、樹脂に配合するその他の成分とし
て、リン系、イオン系、ヒンダードフェノール系などの
酸化防止剤、熱安定剤、紫外線吸収剤、滑剤、離剤、染
料、顔料を含む着色剤、架橋剤、軟化剤、分散剤等の通
常の添加剤と併用することができる。Other components to be added to the resin include phosphorus-based, ionic-based, hindered-phenol-based antioxidants, heat stabilizers, ultraviolet absorbers, lubricants, releasing agents, coloring agents including dyes and pigments. , A cross-linking agent, a softening agent, a dispersant and the like.
【0036】また、必要に応じて、繊維状および/また
は粒状の充填剤を添加して、樹脂の剛性を大幅に向上さ
せることができる。このような充填剤としては、例え
ば、ガラス繊維、炭素繊維、金属繊維、アラミド樹脂、
アスベスト、チタン酸カリウムウイスカ、ワラステナイ
ト、ガラスフレーク、ガラスビーズ、タルク、マイカ、
クレー、炭酸カルシウム、珪酸カルシウム、硫酸バリウ
ム、酸化チタン、溶融シリカ、結晶性シリカ、マグネシ
ア、酸化アルミニウムが挙げられる。If necessary, fibrous and / or granular fillers can be added to significantly improve the rigidity of the resin. As such a filler, for example, glass fiber, carbon fiber, metal fiber, aramid resin,
Asbestos, potassium titanate whisker, walastenite, glass flake, glass beads, talc, mica,
Examples include clay, calcium carbonate, calcium silicate, barium sulfate, titanium oxide, fused silica, crystalline silica, magnesia, and aluminum oxide.
【0037】本発明において、一般式(1)で示される
ニトリロトリス(メチレン)ホスホン酸メラミン塩、及
び必要に応じてその他の上記の添加物を配合してなる難
燃剤は、通常公知の方法で各種樹脂に含有させることが
できる。例えば、硬化性樹脂であれば、難燃剤を硬化性
樹脂およびその他の配合物と同時に混入する方法、樹脂
成分の1種に予め難燃剤を混合しておき、これを硬化性
樹脂と混合する方法、熱可塑性樹脂であれば、難燃剤を
エクストルーダーで溶融混合する方法、あるいは粒子状
物どうしを均一に機械的に混合した後、射出成形機で混
合と同時に成形する方法等が挙げられる。In the present invention, the flame retardant comprising the nitrilotris (methylene) phosphonic acid melamine salt represented by the general formula (1) and, if necessary, other additives as described above is generally prepared by a known method. It can be contained in various resins. For example, in the case of a curable resin, a method in which a flame retardant is mixed with the curable resin and other components simultaneously, and a method in which a flame retardant is mixed in advance with one of the resin components and then mixed with the curable resin In the case of a thermoplastic resin, a method in which a flame retardant is melt-mixed with an extruder, a method in which particles are uniformly and mechanically mixed with each other, and a method in which the particles are mixed with an injection molding machine at the same time as molding are used.
【0038】本発明の難燃性樹脂組成物は、安全なプラ
スチック材料として、電気部品、建築材料、自動車等の
輸送機器、包装材料、家庭日用品等の分野への適用が充
分可能である。The flame-retardant resin composition of the present invention can be sufficiently applied as safe plastic materials to the fields of electric parts, building materials, transportation equipment such as automobiles, packaging materials, household daily necessities and the like.
【0039】[0039]
【実施例】以下、本発明を実施例により詳細に説明する
が、本発明はこれらに限定されるものではない。The present invention will be described below in more detail with reference to examples, but the present invention is not limited to these examples.
【0040】合成例1 <ニトリロトリス(メチレン)ホスホン酸メラミン塩の
調製> ・試料A;ニトリロトリス(メチレン)ホスホン酸・2
メラミン 18Lステンレス製容器に水道水10L、ニトリロトリ
ス(メチレン)ホスホン酸(以下、NTPと略記する)
(50%水溶液)1802.0g(3.00mol)を
加え撹拌した。これを80℃に昇温した後、メラミン7
62.0g(6.00mol)を徐々に加え撹拌した。
メラミン添加終了後、反応溶液のpHが一定(約1.
5)になるまで80℃で撹拌を続けた。その後、遠心濾
過をおこない、白色結晶を得た。この結晶を100℃で
24時間乾燥し、目的物1494.5gを得た。収率9
0.3%(NTPに対する収率)。Synthesis Example 1 <Preparation of Melamine Salt of Nitrilotris (methylene) phosphonic Acid> Sample A: Nitrilotris (methylene) phosphonic acid.2.
Melamine 18L stainless steel container, 10L of tap water, nitrilotris (methylene) phosphonic acid (hereinafter abbreviated as NTP)
(50% aqueous solution) 1802.0 g (3.00 mol) was added and stirred. After the temperature was raised to 80 ° C., melamine 7 was added.
62.0 g (6.00 mol) was gradually added and stirred.
After the addition of melamine, the pH of the reaction solution is constant (about 1.
Stirring was continued at 80 ° C. until 5). Thereafter, centrifugal filtration was performed to obtain white crystals. The crystals were dried at 100 ° C. for 24 hours to obtain 1494.5 g of the desired product. Yield 9
0.3% (yield based on NTP).
【0041】次いで、得られた結晶をミキサーで粉砕処
理して、下記の表1に示す各種の平均粒子径のニトリロ
トリス(メチレン)ホスホン酸・2メラミンを調製し
た。なお、平均粒子径は、レーザー散乱式粒度測定(マ
イクロトラック)により求めた。元素分析によりC、
H、Nを測定した結果、C;19.79%、H;4.3
8%、N;32.02%であった。Next, the obtained crystals were pulverized with a mixer to prepare nitrilotris (methylene) phosphonic acid / 2-melamine having various average particle sizes shown in Table 1 below. The average particle size was determined by laser scattering particle size measurement (Microtrack). By elemental analysis, C,
As a result of measuring H and N, C: 19.79%, H: 4.3
8%, N: 32.02%.
【0042】・試料B;ニトリロトリス(メチレン)ホ
スホン酸・3メラミン 18Lステンレス製容器に水道水15L、NTP(50
%水溶液)1802.0g(3.01mol)を加え撹
拌した。これを80℃に昇温した後、メラミン114
0.0g(9.03mol)を徐々に加え撹拌した。メ
ラミン添加終了後、反応溶液のpHが一定(約1.5)
になるまで80℃で撹拌を続けた。その後、遠心濾過を
おこない、白色結晶を得た。この結晶を100℃で24
時間乾燥し、目的物1909.66gを得た。収率9
3.9%(NTPに対する収率)。 Sample B: nitrilotris (methylene) ho
Suhon acid 3 Melamine 18L stainless steel container of tap water 15L, NTP (50
% Aqueous solution) and stirred. After the temperature was raised to 80 ° C., melamine 114 was added.
0.0 g (9.03 mol) was gradually added and stirred. After addition of melamine, the pH of the reaction solution is constant (about 1.5)
Stirring was continued at 80 ° C. until. Thereafter, centrifugal filtration was performed to obtain white crystals. The crystals are grown at 100 ° C for 24 hours.
After drying for 1 hour, 1909.66 g of the target product was obtained. Yield 9
3.9% (Yield based on NTP).
【0043】次いで、得られた結晶をミキサーで粉砕処
理して、下記の表1に示す各種の平均粒子径のニトリロ
トリス(メチレン)ホスホン酸・3メラミンを調製し
た。なお、平均粒子径は、レーザー散乱式粒度測定(マ
イクロトラック)により求めた。元素分析によりC、
H、Nを測定した結果、C;20.84%、H;4.4
1%、N;38.49%であった。Then, the obtained crystals were pulverized by a mixer to prepare nitrilotris (methylene) phosphonic acid / 3 melamine having various average particle sizes shown in Table 1 below. The average particle size was determined by laser scattering particle size measurement (Microtrack). By elemental analysis, C,
As a result of measuring H and N, C: 20.84%, H: 4.4
1%, N; 38.49%.
【0044】・試料C;ニトリロトリス(メチレン)ホ
スホン酸・4メラミン 18Lステンレス製容器に水道水15L、NTP(50
%水溶液)897.0g(1.49mol)を加え撹拌
した。これを80℃に昇温した後、メラミン751.6
g(5.96mol)を徐々に加え撹拌した。メラミン
添加終了後、反応溶液のpHが一定(約4.2)になる
まで80℃で撹拌を続けた。その後、遠心濾過をおこな
い、白色結晶を得た。この結晶を100℃で24時間乾
燥し、目的物1144.06gを得た。収率95.2%
(NTPに対する収率)。 Sample C: nitrilotris (methylene) ho
Sulfonic acid / 4 melamine 18L Stainless steel container 15L tap water, NTP (50
897.0 g (1.49 mol) was added and stirred. After the temperature was raised to 80 ° C., melamine 751.6 was used.
g (5.96 mol) was gradually added and stirred. After completion of the melamine addition, stirring was continued at 80 ° C. until the pH of the reaction solution became constant (about 4.2). Thereafter, centrifugal filtration was performed to obtain white crystals. The crystals were dried at 100 ° C. for 24 hours to obtain 1144.06 g of the desired product. 95.2% yield
(Yield based on NTP).
【0045】次いで、得られた結晶をミキサーで粉砕処
理して、下記の表1に示す各種の平均粒子径のニトリロ
トリス(メチレン)ホスホン酸・4メラミンを調製し
た。なお、平均粒子径は、レーザー散乱式粒度測定(マ
イクロトラック)により求めた。元素分析によりC、
H、Nを測定した結果、C;21.52%、H;4.4
1%、N;41.82%であった。Next, the obtained crystals were pulverized with a mixer to prepare nitrilotris (methylene) phosphonic acid / 4 melamine having various average particle sizes shown in Table 1 below. The average particle size was determined by laser scattering particle size measurement (Microtrack). By elemental analysis, C,
As a result of measuring H and N, C: 21.52%, H: 4.4
1%, N; 41.82%.
【0046】・試料D;ニトリロトリス(メチレン)ホ
スホン酸・5メラミン 18Lステンレス製容器に水道水15L、NTP(50
%水溶液)897.0g(1.5mol)を加え攪拌し
た。これを80℃に昇温した後、メラミン945.9g
(7.5mol)を徐々に加え攪拌した。メラミン添加
終了後、反応溶液のpHが一定(約4.3)になるまで
80℃で攪拌を続けた。その後、遠心濾過をおこない、
白色結晶を得た。この結晶を100℃で24時間乾燥
し、目的物785.4gを得た。収率84.5%(NT
Pに対する収率)。 Sample D: nitrilotris (methylene) ho
Sulfonic acid / 5 melamine 18L Stainless steel container in tap water 15L, NTP (50
897.0 g (1.5 mol) was added and stirred. After the temperature was raised to 80 ° C., 945.9 g of melamine was used.
(7.5 mol) was gradually added thereto, followed by stirring. After completion of the melamine addition, stirring was continued at 80 ° C. until the pH of the reaction solution became constant (about 4.3). After that, perform centrifugal filtration,
White crystals were obtained. The crystals were dried at 100 ° C. for 24 hours to obtain 785.4 g of the desired product. Yield 84.5% (NT
Yield based on P).
【0047】次いで、得られた結晶をミキサーで粉砕処
理して、下記の表1に示す各種の平均粒子径のニトリロ
トリス(メチレン)ホスホン酸・5メラミンを調製し
た。なお、平均粒子径は、レーザー散乱式粒度測定(マ
イクロトラック)により求めた。元素分析によりC、
H、Nを測定した結果、C;22.9%、H;4.1
%、N;46.1%であった。Next, the obtained crystals were pulverized with a mixer to prepare nitrilotris (methylene) phosphonic acid / 5 melamine having various average particle sizes shown in Table 1 below. The average particle size was determined by laser scattering particle size measurement (Microtrack). By elemental analysis, C,
As a result of measuring H and N, C: 22.9%, H: 4.1.
%, N; 46.1%.
【0048】[0048]
【表1】 [Table 1]
【0049】(注1)平均粒子径は、レーザー散乱式粒
度測定装置(マイクロトラック)により求めた値であ
る。(Note 1) The average particle diameter is a value determined by a laser scattering particle size analyzer (Microtrack).
【0050】実施例1〜8及び比較例1〜4 エチルエチレンアクリレート(以下、EEAと略記す
る)樹脂に、表2〜3に示した配合割合で、各種の添加
剤を添加し、120〜130℃に設定した熱ロールに
て、5〜10分間混練した。Examples 1 to 8 and Comparative Examples 1 to 4 Various additives were added to ethyl ethylene acrylate (hereinafter abbreviated as EEA) resin at the compounding ratios shown in Tables 2 to 3, and 120 to 130 The mixture was kneaded for 5 to 10 minutes with a hot roll set at ℃.
【0051】加熱プレスを用いて成形圧力150kg/
cm2、加圧時間5分間、金型温度115℃で、厚さ3
mmのシートを作成し、更に、長さ125mm、幅13
mmの試験片を作成し、樹脂の難燃性および表面性を試
験した。なお、水酸化マグネシウムは、協和化学社製の
キスマ5Aを用いた。The molding pressure was 150 kg /
cm 2 , pressurization time 5 minutes, mold temperature 115 ° C, thickness 3
mm sheet, length 125 mm, width 13
mm test pieces were prepared, and the resin was tested for flame retardancy and surface properties. In addition, Kisuma 5A manufactured by Kyowa Chemical Co., Ltd. was used as magnesium hydroxide.
【0052】<難燃性試験>難燃性試験は、上記で調整
した長さ125mm×幅13mm×厚さ3mmに加工し
た樹脂をUL94に分類した材料の垂直燃焼試験(94
V−0、94V−1及び94V−2)に従って試験し
た。その結果を表5および表6に示した。なお、UL9
4の可否条件は表4のとおりである。<Flame Retardancy Test> The flame retardancy test is a vertical flame test (94) of a material obtained by classifying a resin processed into a length of 125 mm × a width of 13 mm × a thickness of 3 mm adjusted as described above into UL94.
V-0, 94V-1 and 94V-2). The results are shown in Tables 5 and 6. In addition, UL9
Table 4 shows the conditions for the availability of 4.
【0053】[0053]
【表2】 [Table 2]
【0054】[0054]
【表3】 [Table 3]
【0055】[0055]
【表4】 [Table 4]
【0056】[0056]
【表5】 [Table 5]
【0057】[0057]
【表6】 [Table 6]
【0058】(注1)表面性は、手触りにより測定し
た。 (注2)表5および表6の接炎後の残炎時間は、表4中
の試験2に相当し、2回目の残炎時間は、1回目を試験
した同じ試験片をそののまま用いて試験した接炎後の残
炎時間である。(Note 1) Surface properties were measured by touch. (Note 2) The residual flame time after flame contact in Tables 5 and 6 corresponds to Test 2 in Table 4. For the second residual flame time, the same test piece used in the first test was used as it was. It is the after-flame time after the flame contact tested.
【0059】表5および表6の結果より、ホスホン酸メ
ラミン塩の粒径を小さくすることにより、樹脂に対する
分散性がよくなり、UL94に基づく難燃性試験におい
て、データのバラツキもなく、安定した難燃性が樹脂に
対して付与できることが認められる。From the results shown in Tables 5 and 6, the particle size of the melamine phosphonic acid salt was reduced to improve the dispersibility of the resin in the resin. It is recognized that flame retardancy can be imparted to the resin.
【0060】実施例9〜16及び比較例5〜8 ホルムアルデヒド/フェノール=0.9のモル比で調製
したノボラック樹脂に対して、表7〜8に示した配合割
合で、各種の添加剤を配合し、80〜90℃に設定され
た熱ロールにて5分間混練した。粉砕後、万能プレスを
用いて成形圧力250kg/cm2、加圧時間60秒、
金型温度150℃で所定形状を有する成形品を作成し
た。Examples 9 to 16 and Comparative Examples 5 to 8 Novolak resins prepared at a molar ratio of formaldehyde / phenol = 0.9 were mixed with various additives at the mixing ratios shown in Tables 7 to 8. Then, the mixture was kneaded with a hot roll set at 80 to 90 ° C. for 5 minutes. After crushing, using a universal press, forming pressure 250 kg / cm 2 , pressing time 60 seconds,
A molded product having a predetermined shape was prepared at a mold temperature of 150 ° C.
【0061】難燃性試験は、実施例1〜8と同様な操作
方法で評価した。その結果を表9および表10に示し
た。The flame retardancy test was evaluated by the same operation method as in Examples 1 to 8. The results are shown in Tables 9 and 10.
【0062】[0062]
【表7】 [Table 7]
【0063】[0063]
【表8】 [Table 8]
【0064】[0064]
【表9】 [Table 9]
【0065】[0065]
【表10】 [Table 10]
【0066】実施例17〜24及び比較例9〜12 各種樹脂に表11に示した各種の添加剤を添加し、30
mmΦ軸押出機を用いて射出成形により、ASTMD−
638に規定されている引張試験片を作成し、強度と伸
度をJIS K7113の試験方法に基づいて測定し
た。Examples 17 to 24 and Comparative Examples 9 to 12 Various additives shown in Table 11 were added to various resins.
ASTM D- by injection molding using a mmΦ screw extruder
A tensile test specimen specified in 638 was prepared, and strength and elongation were measured based on the test method of JIS K7113.
【0067】また、同様にUL94に基づく難燃性評価
試験片を作成し、燃焼性を評価した。その結果を表12
に示す。なお、各樹脂毎の溶融押出、ペレット乾燥、射
出成形条件を下記に示した。Similarly, a test piece for evaluating flame retardancy based on UL94 was prepared, and the flammability was evaluated. Table 12 shows the results.
Shown in The conditions of melt extrusion, pellet drying, and injection molding for each resin are shown below.
【0068】・ポリブチレンテレフタレート(以下、P
BTと略記する) 押出;250〜290℃/150rpm 乾燥;110℃/12時間 成形;250〜290℃/金型80℃ ・ナイロン6 押出;250〜300℃/150rpm 乾燥;100℃/24時間 成形;250〜300℃/金型80℃ ・ポリカーボネート 押出;260〜320℃/75rpm 乾燥;120℃/12時間 成形;260〜320℃/金型110℃ ・ポリフェニレンオキシドとポリスチレンの混合物(混
合重量比;60:40、以下、PPOと略記する) 押出;240〜310℃/70rpm 乾燥;110℃/4時間 成形;240〜320℃/金型90℃Polybutylene terephthalate (hereinafter referred to as P
Extrusion; 250-290 ° C / 150 rpm drying; 110 ° C / 12 hours molding; 250-290 ° C / die 80 ° C ・ Nylon 6 extrusion; 250-300 ° C / 150 rpm drying; 100 ° C / 24 hours molding 250-300 ° C / die 80 ° C ・ Polycarbonate extrusion; 260-320 ° C / 75 rpm drying; 120 ° C / 12 hours molding; 260-320 ° C / die 110 ° C ・ A mixture of polyphenylene oxide and polystyrene (mixing weight ratio; 60:40; hereinafter abbreviated as PPO) Extrusion; 240-310 ° C / 70 rpm Drying; 110 ° C / 4 hours Molding; 240-320 ° C / die 90 ° C
【0069】[0069]
【表11】 [Table 11]
【0070】[0070]
【表12】 [Table 12]
【0071】実施例25〜28及び比較例13 ポリプロピレン樹脂(以下、PPと略記する)に、表1
3に示した配合割合で、各種の添加剤を添加し、230
℃に設定した熱ロールにて、5分間混練した。スクリュ
ー回転数87rpmで溶融押出した。射出成形(シリン
ダー温度:230℃、金型温度50℃)によりUL94
に基づく試験片を作成した。Examples 25 to 28 and Comparative Example 13 A polypropylene resin (hereinafter abbreviated as PP) was added to Table 1
Various additives were added at the mixing ratios shown in FIG.
The mixture was kneaded for 5 minutes with a hot roll set at ℃. Melt extrusion was performed at a screw rotation speed of 87 rpm. UL94 by injection molding (cylinder temperature: 230 ° C, mold temperature 50 ° C)
The test piece based on was prepared.
【0072】なお、赤燐は、水酸化アルミニウムと水酸
化チタンにより表面を改質したものを用いた。難燃性試
験の結果を表13に示した。The red phosphorus whose surface was modified with aluminum hydroxide and titanium hydroxide was used. Table 13 shows the results of the flame retardancy test.
【0073】[0073]
【表13】 [Table 13]
【0074】[0074]
【発明の効果】以上説明した様に、本発明の難燃性樹脂
組成物は、樹脂分散性の優れたノンハロゲン系の難燃剤
を用いているので、各種樹脂に対して安定して優れた難
燃性を付与できる効果を有する。As described above, the flame-retardant resin composition of the present invention uses a non-halogen flame retardant having excellent resin dispersibility. It has the effect of imparting flammability.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 FI テーマコート゛(参考) C08K 5/5317 C08K 5/5317 (72)発明者 松本 信夫 東京都江東区亀戸9丁目11番1号 日本化 学工業株式会社内 Fターム(参考) 4J002 AC031 BB031 BB041 BB051 BB061 BB071 BB121 BB151 BB211 BC031 BD151 BF021 BF031 BF051 BG061 BG101 CB001 CC031 CC121 CC151 CC161 CC181 CC182 CD001 CD191 CF001 CF061 CF071 CF211 CF281 CG011 CH021 CH071 CH081 CH121 CK021 CL001 CL011 CL031 DA058 DE077 DE078 DE087 DE097 DE098 DE108 DE127 DE128 DE137 DE138 DE147 DE148 DE187 DE238 DE267 DE277 DE287 DG047 DG057 DH047 DH048 DH058 DJ007 DJ037 DJ047 DK007 DK008 ER028 EU188 EU198 EV188 EV348 EW048 EW126 EW128 EW138 EW158 FD010 FD132 FD136 FD137 FD138 ──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme court ゛ (Reference) C08K 5/5317 C08K 5/5317 (72) Inventor Nobuo Matsumoto 9-11-1, Kameido, Koto-ku, Tokyo Japan Chemical Chemical Co., Ltd. F-term (Reference) 4J002 AC031 BB031 BB041 BB051 BB061 BB071 BB121 BB151 BB211 BC031 BD151 BF021 BF031 BF051 BG061 BG101 CB001 CC031 CC121 CC151 CC161 CC181 CC182 CD1 CD191 CF01 CF01 CF06 CL031 DA058 DE077 DE078 DE087 DE097 DE098 DE108 DE127 DE128 DE137 DE138 DE147 DE148 DE187 DE238 DE267 DE277 DE287 DG047 DG057 DH047 DH048 DH058 DJ007 DJ037 DJ047 DK007 DK008 ER028 EU188 EU198 EV188 EV348 FD 138 138 EW 138 FD 138
Claims (5)
(1) 【化1】 (式中、Mは、メラミンを表し、nは2〜5の整数を表
す。)で示されるニトリロトリス(メチレン)ホスホン
酸メラミン塩を含有することを特徴とする難燃性樹脂組
成物。1. The following general formula (1) having an average particle size of 20 μm or less. (Wherein, M represents melamine, and n represents an integer of 2 to 5). A flame-retardant resin composition comprising a melamine salt of nitrilotris (methylene) phosphonic acid represented by the formula:
ン)ホスホン酸メラミン塩と水和金属化合物とを含有す
る請求項1記載の難燃性樹脂組成物。2. The flame-retardant resin composition according to claim 1, comprising the melamine salt of nitrilotris (methylene) phosphonic acid according to claim 1 and a hydrated metal compound.
の難燃性樹脂組成物。3. The flame retardant resin composition according to claim 2, further comprising a flame retardant auxiliary.
3記載の難燃性樹脂組成物。4. The flame-retardant resin composition according to claim 3, wherein the flame-retardant auxiliary is a phosphorus-based flame retardant.
ウム、ポリリン酸アンモニウム、リン酸メラミン、リン
酸グアニル尿素、ポリリン酸メラミン及びリン酸グアニ
ジンから選ばれる少なくとも1種である請求項3又は4
記載の難燃性樹脂組成物。5. The phosphorus-based flame retardant is at least one selected from red phosphorus, ammonium phosphate, ammonium polyphosphate, melamine phosphate, guanylurea phosphate, melamine polyphosphate and guanidine phosphate. 4
The flame-retardant resin composition according to the above.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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JP24132199A JP2001064521A (en) | 1999-08-27 | 1999-08-27 | Flame retardant resin composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP24132199A JP2001064521A (en) | 1999-08-27 | 1999-08-27 | Flame retardant resin composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2001064521A true JP2001064521A (en) | 2001-03-13 |
Family
ID=17072568
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP24132199A Pending JP2001064521A (en) | 1999-08-27 | 1999-08-27 | Flame retardant resin composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2001064521A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003027176A1 (en) * | 2001-08-07 | 2003-04-03 | General Electric Company | Polycarbonate resin compositions and articles therefro |
JP2006104373A (en) * | 2004-10-07 | 2006-04-20 | Japan Polypropylene Corp | Flame retardant polypropylene resin composition |
CN104497041A (en) * | 2014-12-09 | 2015-04-08 | 东华大学 | Melamine aminotrimethylene phosphonate and preparation method thereof |
CN110922518A (en) * | 2019-11-30 | 2020-03-27 | 华东理工大学 | A kind of water-swellable flame retardant and its preparation method and application |
-
1999
- 1999-08-27 JP JP24132199A patent/JP2001064521A/en active Pending
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003027176A1 (en) * | 2001-08-07 | 2003-04-03 | General Electric Company | Polycarbonate resin compositions and articles therefro |
CN100371375C (en) * | 2001-08-07 | 2008-02-27 | 通用电气公司 | Polycarbonate resin compositions and articles therefrom |
JP2006104373A (en) * | 2004-10-07 | 2006-04-20 | Japan Polypropylene Corp | Flame retardant polypropylene resin composition |
CN104497041A (en) * | 2014-12-09 | 2015-04-08 | 东华大学 | Melamine aminotrimethylene phosphonate and preparation method thereof |
CN110922518A (en) * | 2019-11-30 | 2020-03-27 | 华东理工大学 | A kind of water-swellable flame retardant and its preparation method and application |
CN110922518B (en) * | 2019-11-30 | 2021-04-23 | 华东理工大学 | Water-resistant intumescent flame retardant and preparation method and application thereof |
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