JPWO2019240181A1 - リン酸アミン塩組成物、リン酸アミン塩難燃剤組成物、これを含有する難燃性合成樹脂組成物およびその成形体 - Google Patents
リン酸アミン塩組成物、リン酸アミン塩難燃剤組成物、これを含有する難燃性合成樹脂組成物およびその成形体 Download PDFInfo
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- JPWO2019240181A1 JPWO2019240181A1 JP2020525625A JP2020525625A JPWO2019240181A1 JP WO2019240181 A1 JPWO2019240181 A1 JP WO2019240181A1 JP 2020525625 A JP2020525625 A JP 2020525625A JP 2020525625 A JP2020525625 A JP 2020525625A JP WO2019240181 A1 JPWO2019240181 A1 JP WO2019240181A1
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- Prior art keywords
- phosphate
- amine
- composition
- mass
- manufactured
- 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.)
- Granted
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- -1 Amine phosphate salt Chemical class 0.000 title claims abstract description 252
- 239000000203 mixture Substances 0.000 title claims abstract description 190
- 239000003063 flame retardant Substances 0.000 title claims abstract description 132
- 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 118
- 229920003002 synthetic resin Polymers 0.000 title claims abstract description 80
- 239000000057 synthetic resin Substances 0.000 title claims abstract description 80
- 150000001412 amines Chemical class 0.000 title claims abstract description 78
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 title 1
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 73
- 239000010452 phosphate Substances 0.000 claims abstract description 73
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 68
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims abstract description 42
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 34
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 29
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 22
- 229920005672 polyolefin resin Polymers 0.000 claims description 4
- 238000012545 processing Methods 0.000 abstract description 43
- 238000005260 corrosion Methods 0.000 abstract description 39
- 230000007797 corrosion Effects 0.000 abstract description 39
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 61
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical group OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 description 52
- 238000004519 manufacturing process Methods 0.000 description 40
- 235000011007 phosphoric acid Nutrition 0.000 description 34
- 229960005141 piperazine Drugs 0.000 description 33
- 230000000052 comparative effect Effects 0.000 description 32
- NQQWFVUVBGSGQN-UHFFFAOYSA-N phosphoric acid;piperazine Chemical group OP(O)(O)=O.C1CNCCN1 NQQWFVUVBGSGQN-UHFFFAOYSA-N 0.000 description 32
- 239000000126 substance Substances 0.000 description 30
- 229920000388 Polyphosphate Polymers 0.000 description 28
- 239000001205 polyphosphate Substances 0.000 description 28
- 235000011176 polyphosphates Nutrition 0.000 description 28
- 229960001954 piperazine phosphate Drugs 0.000 description 26
- 238000012360 testing method Methods 0.000 description 25
- 239000013500 performance material Substances 0.000 description 22
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 description 20
- MWFNQNPDUTULBC-UHFFFAOYSA-N phosphono dihydrogen phosphate;piperazine Chemical compound C1CNCCN1.OP(O)(=O)OP(O)(O)=O MWFNQNPDUTULBC-UHFFFAOYSA-N 0.000 description 20
- 235000014113 dietary fatty acids Nutrition 0.000 description 19
- 239000000194 fatty acid Substances 0.000 description 19
- 229930195729 fatty acid Natural products 0.000 description 19
- 230000001629 suppression Effects 0.000 description 19
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 18
- 238000006482 condensation reaction Methods 0.000 description 18
- 230000018044 dehydration Effects 0.000 description 18
- 238000006297 dehydration reaction Methods 0.000 description 18
- 150000004665 fatty acids Chemical class 0.000 description 18
- 239000006087 Silane Coupling Agent Substances 0.000 description 17
- 230000000694 effects Effects 0.000 description 17
- 229910001701 hydrotalcite Inorganic materials 0.000 description 17
- 229960001545 hydrotalcite Drugs 0.000 description 17
- 239000000463 material Substances 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- 235000011180 diphosphates Nutrition 0.000 description 15
- 229940048084 pyrophosphate Drugs 0.000 description 15
- 239000004743 Polypropylene Substances 0.000 description 14
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 14
- PWZFXELTLAQOKC-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide;tetrahydrate Chemical compound O.O.O.O.[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 PWZFXELTLAQOKC-UHFFFAOYSA-A 0.000 description 14
- 230000001771 impaired effect Effects 0.000 description 14
- 229920001155 polypropylene Polymers 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 12
- 239000000835 fiber Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 229910052698 phosphorus Inorganic materials 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 229920002545 silicone oil Polymers 0.000 description 12
- 101100323621 Drosophila melanogaster Drip gene Proteins 0.000 description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
- 239000007983 Tris buffer Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 239000000314 lubricant Substances 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 11
- 229920001296 polysiloxane Polymers 0.000 description 11
- 229920006310 Asahi-Kasei Polymers 0.000 description 10
- 229920004482 WACKER® Polymers 0.000 description 10
- 239000011574 phosphorus Substances 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 9
- 239000004014 plasticizer Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000003484 crystal nucleating agent Substances 0.000 description 8
- DNVIGFDFKWXCCP-UHFFFAOYSA-N phosphoric acid;piperazine Chemical compound OP(O)(O)=O.OP(O)(O)=O.C1CNCCN1 DNVIGFDFKWXCCP-UHFFFAOYSA-N 0.000 description 8
- 229920002725 thermoplastic elastomer Polymers 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000011787 zinc oxide Substances 0.000 description 7
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 6
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 6
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229910044991 metal oxide Inorganic materials 0.000 description 6
- 150000004706 metal oxides Chemical class 0.000 description 6
- 229920000137 polyphosphoric acid Polymers 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 6
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 5
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 5
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000004255 ion exchange chromatography Methods 0.000 description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000012779 reinforcing material Substances 0.000 description 5
- 239000005060 rubber Substances 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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- 239000006057 Non-nutritive feed additive Substances 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
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- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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- 229910052731 fluorine Inorganic materials 0.000 description 4
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- 239000000395 magnesium oxide Substances 0.000 description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
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- 239000002994 raw material Substances 0.000 description 4
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
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- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 3
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- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
- 235000013539 calcium stearate Nutrition 0.000 description 3
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- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 3
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- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- JMUOXOJMXILBTE-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 JMUOXOJMXILBTE-UHFFFAOYSA-N 0.000 description 2
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- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- GDESWOTWNNGOMW-UHFFFAOYSA-N resorcinol monobenzoate Chemical compound OC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 GDESWOTWNNGOMW-UHFFFAOYSA-N 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 229940045845 sodium myristate Drugs 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- ZHROMWXOTYBIMF-UHFFFAOYSA-M sodium;1,3,7,9-tetratert-butyl-11-oxido-5h-benzo[d][1,3,2]benzodioxaphosphocine 11-oxide Chemical compound [Na+].C1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP([O-])(=O)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C ZHROMWXOTYBIMF-UHFFFAOYSA-M 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- XTIVBOWLUYDHKE-UHFFFAOYSA-M sodium;cyclohexanecarboxylate Chemical compound [Na+].[O-]C(=O)C1CCCCC1 XTIVBOWLUYDHKE-UHFFFAOYSA-M 0.000 description 1
- YKIBJOMJPMLJTB-UHFFFAOYSA-M sodium;octacosanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O YKIBJOMJPMLJTB-UHFFFAOYSA-M 0.000 description 1
- JUQGWKYSEXPRGL-UHFFFAOYSA-M sodium;tetradecanoate Chemical compound [Na+].CCCCCCCCCCCCCC([O-])=O JUQGWKYSEXPRGL-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 229920006027 ternary co-polymer Polymers 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- VKFFEYLSKIYTSJ-UHFFFAOYSA-N tetraazanium;phosphonato phosphate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[O-]P([O-])(=O)OP([O-])([O-])=O VKFFEYLSKIYTSJ-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- WUPCFMITFBVJMS-UHFFFAOYSA-N tetrakis(1,2,2,6,6-pentamethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)CC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 WUPCFMITFBVJMS-UHFFFAOYSA-N 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000007970 thio esters Chemical group 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZYMHKOVQDOFPHH-UHFFFAOYSA-N trimethoxy(oct-1-enyl)silane Chemical compound CCCCCCC=C[Si](OC)(OC)OC ZYMHKOVQDOFPHH-UHFFFAOYSA-N 0.000 description 1
- JRSJRHKJPOJTMS-MDZDMXLPSA-N trimethoxy-[(e)-2-phenylethenyl]silane Chemical compound CO[Si](OC)(OC)\C=C\C1=CC=CC=C1 JRSJRHKJPOJTMS-MDZDMXLPSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 229960003487 xylose Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 235000019352 zinc silicate Nutrition 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/5205—Salts of P-acids with N-bases
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/025—Copolymer of an unspecified olefin with a monomer other than an olefin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
- C08K2003/321—Phosphates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
Abstract
Description
まず、本発明のリン酸アミン塩組成物について説明する。本発明のリン酸アミン塩組成物は、リン酸アミン塩を1種以上含有する組成物を意味し、アンモニウムカチオンを100〜2000質量ppm含有する。本発明のリン酸アミン塩組成物において、リン酸アミン塩における「リン酸」とはオルトリン酸、ピロリン酸およびポリリン酸の総称である。
・イオンクロマトグラフィー:ICS−2000(DIONEX社製)
・カラム:DIONEX IONPAC CS17(4×250mm)
・溶離液:メタンスルホン酸水溶液
ここで、式(1)中、x1およびx2は各々下記式で表される条件を満たす数を示し、mは実数を示す。
0≦x2/x1<10、2≦x1+x2<20
・イオンクロマトグラフィー:ICS−2100(DIONEX社製)
・カラム:DIONEX IONPAC AS19(4×250mm)
・溶離液:水酸化カリウム水溶液
・イオンクロマトグラフィー:ICS−2000(DIONEX社製)
・カラム:DIONEX IONPAC CS17(4×250mm)
・溶離液:メタンスルホン酸水溶液
なお、本分析方法の検出限界(LOD)は 0.1質量ppmである。
オルトリン酸一メラミンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度215〜225℃、回転数800〜1000rpmの条件で5.0時間加熱撹拌し、脱水縮合反応を行い、リン酸メラミン組成物−1を得た。得られたリン酸メラミン組成物−1は、オルトリン酸一メラミンを1.9質量%、ピロリン酸メラミンを98.0質量%、3分子以上のオルトリン酸一メラミンが縮合したポリリン酸メラミンを0.1質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを950ppm含んでいた。
オルトリン酸一メラミンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度210〜220℃、回転数800〜1000rpmの条件で6.0時間加熱撹拌し、脱水縮合反応を行い、リン酸メラミン組成物−2を得た。得られたリン酸メラミン組成物−1は、オルトリン酸一メラミンを3.2質量%、ピロリン酸メラミンを96.75質量%、3分子以上のオルトリン酸一メラミンが縮合したポリリン酸メラミンを0.05質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを130ppm含んでいた。
オルトリン酸一メラミンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度210〜220℃、回転数800〜1000rpmの条件で7.0時間加熱撹拌し、脱水縮合反応を行い、リン酸メラミン組成物−3を得た。得られたリン酸メラミン組成物−3は、オルトリン酸一メラミンを2.8質量%、ピロリン酸メラミンを97.1質量%、3分子以上のオルトリン酸一メラミンが縮合したポリリン酸メラミンを0.1質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを320ppm含んでいた。
オルトリン酸一メラミンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度215〜225℃、回転数800〜1000rpmの条件で6.0時間加熱撹拌し、脱水縮合反応を行い、リン酸メラミン組成物−4を得た。得られたリン酸メラミン組成物−4は、オルトリン酸一メラミンを1.5質量%、ピロリン酸メラミンを98.2質量%、3分子以上のオルトリン酸一メラミンが縮合したポリリン酸メラミンを0.3質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを1470ppm含んでいた。
オルトリン酸一メラミンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度215〜225℃、回転数800〜1000rpmの条件で7.5時間加熱撹拌し、脱水縮合反応を行い、リン酸メラミン組成物−4を得た。得られたリン酸メラミン組成物−5は、オルトリン酸一メラミンを1.0質量%、ピロリン酸メラミンを98.5質量%、3分子以上のオルトリン酸一メラミンが縮合したポリリン酸メラミンを0.5質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを1960ppm含んでいた。
オルトリン酸一メラミンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度210〜215℃、回転数800〜900rpmの条件で7.5時間加熱撹拌し、脱水縮合反応を行い、比較リン酸メラミン組成物−1を得た。得られた比較リン酸メラミン組成物−1は、オルトリン酸一メラミンを3.6質量%、ピロリン酸メラミンを96.35質量%、3分子以上のオルトリン酸一メラミンが縮合したポリリン酸メラミンを0.05質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを50ppm含んでいた。
オルトリン酸一メラミンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度215〜225℃、回転数800〜1000rpmの条件で8.5時間加熱撹拌し、脱水縮合反応を行い、比較リン酸メラミン組成物−2を得た。得られた比較リン酸メラミン組成物−5は、オルトリン酸一メラミンを0.6質量%、ピロリン酸メラミンを98.6質量%、3分子以上のオルトリン酸一メラミンが縮合したポリリン酸メラミンを0.8質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを2120ppm含んでいた。
水中、5〜20℃の温度で、ピロリン酸とメラミンを中和反応させ、沈殿したピロリン酸メラミンを濾別し、蒸留水で洗浄後、30℃で真空乾燥し、粉末状の比較ピロリン酸メラミン−3を得た。得られた比較ピロリン酸メラミン−3は、ピロリン酸メラミン100質量%であった(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンは、検出限界(LOD)未満であった。
二オルトリン酸一ピペラジンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度235〜245℃、回転数800〜1000rpmの条件で3.0時間加熱撹拌し、脱水縮合反応を行い、リン酸ピペラジン組成物−6を得た。得られたリン酸ピペラジン組成物−6は、二オルトリン酸一ピペラジンを1.0質量%、ピロリン酸ピペラジンを98.95質量%、3分子以上の二オルトリン酸一ピペラジンが縮合したポリリン酸ピペラジンを0.05質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを660ppm含んでいた。
二オルトリン酸一ピペラジンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度230〜240℃、回転数800〜1000rpmの条件で4.0時間加熱撹拌し、脱水縮合反応を行い、リン酸ピペラジン組成物−7を得た。得られたリン酸ピペラジン組成物−7は、二オルトリン酸一ピペラジンを2.1質量%、ピロリン酸ピペラジンを97.85質量%、3分子以上の二オルトリン酸一ピペラジンが縮合したポリリン酸ピペラジンを0.05質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを120ppm含んでいた。
二オルトリン酸一ピペラジンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度230〜240℃、回転数800〜1000rpmの条件で5.0時間加熱撹拌し、脱水縮合反応を行い、リン酸ピペラジン組成物−8を得た。得られたリン酸ピペラジン−8は、二オルトリン酸一ピペラジンを1.7質量%、ピロリン酸ピペラジンを98.25質量%、3分子以上の二オルトリン酸一ピペラジンが縮合したポリリン酸ピペラジンを0.05質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを310ppm含んでいた。
二オルトリン酸一ピペラジンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度235〜245℃、回転数800〜1000rpmの条件で5.0時間加熱撹拌し、脱水縮合反応を行い、リン酸ピペラジン組成物−9を得た。得られたリン酸ピペラジン組成物−9は、二オルトリン酸一ピペラジンを0.6質量%、ピロリン酸ピペラジンを99.2質量%、3分子以上の二オルトリン酸一ピペラジンが縮合したポリリン酸ピペラジンを0.2質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを1420ppm含んでいた。
二オルトリン酸一ピペラジンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度235〜245℃、回転数800〜1000rpmの条件で6.0時間加熱撹拌し、脱水縮合反応を行い、リン酸ピペラジン組成物−10を得た。得られたリン酸ピペラジン組成物−10は、二オルトリン酸一ピペラジンを0.4質量%、ピロリン酸ピペラジンを99.2質量%、3分子以上のオルトリン酸一ピペラジンが縮合したポリリン酸ピペラジンを0.4質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを1910ppm含んでいた。
二オルトリン酸一ピペラジンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度230〜235℃、回転数800〜900rpmの条件で5.0時間加熱撹拌し、脱水縮合反応を行い、比較リン酸ピペラジン組成物−4を得た。得られた比較リン酸ピペラジン組成物−4は、二オルトリン酸一ピペラジンを2.4質量%、ピロリン酸ピペラジンを97.55質量%、3分子以上の二オルトリン酸一ピペラジンが縮合したポリリン酸ピペラジンを0.05質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを40ppm含んでいた。
二オルトリン酸一ピペラジンの粉末30Kgを、熱媒を通したヘンシェルミキサー(三井鉱山製、FM150J/T、容量150L)を使用して、温度240〜250℃、回転数800〜1000rpmの条件で7.0時間加熱撹拌し、脱水縮合反応を行い、比較リン酸ピペラジン組成物−5を得た。得られたリン酸ピペラジン組成物−5は、二オルトリン酸一ピペラジンを0.3質量%、ピロリン酸ピペラジンを99.1質量%、3分子以上の二オルトリン酸一ピペラジンが縮合したポリリン酸ピペラジンを0.6質量%含有していた。(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンを2170ppm含んでいた。
水中、5〜20℃の温度で、ピロリン酸とピペラジンを中和反応させ、沈殿したピロリン酸ピペラジンを濾別し、蒸留水で洗浄後、30℃で真空乾燥し、粉末状の比較ピロリン酸ピペラジン−6を得た。比較ピロリン酸ピペラジン−6はピロリン酸ピペラジン100質量%であった(ただし、全リン酸アミン塩の合計を100質量%とする)。また、アンモニウムカチオンは、検出限界(LOD)未満であった。
表1〜3記載の配合で、製造例1〜10で得られたリン酸アミン塩組成物、および比較製造例1〜6で得られた比較リン酸アミン塩組成物を用いて、リン酸アミン塩難燃剤組成物を調整した。なお、表1〜3には、リン酸アミン塩中のアンモニウムカチオンの含有量を併記した。得られたリン酸アミン塩難燃剤組成物の腐食試験を、下記腐食試験方法で行った。結果を表1〜3に示す。
容量100mlのガラス製のテストチューブにリン酸アミン塩難燃剤組成物10gを入れた。更にそのテストチューブの中に直径10mmの真鍮製の試験棒を、リン酸アミン塩難燃剤組成物に試験棒の下半分が浸るように入れた。テストチューブを、air中、200℃のブロックバスに入れ加熱した。400時間後の、真鍮製の試験棒のリン酸アミン塩難燃剤組成物に浸かっていた部分の表面状態を目視で確認し、以下のように評価した。
ポリプロピレン(メルトフローレート=8g/10min)60質量部に、ステアリン酸カルシウム(滑剤)0.1質量部、テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオン酸メチル]メタン(フェノール系酸化防止剤)0.1質量部、トリス(2,4−ジ−第三ブチルフェニル)ホスファイト(リン系酸化防止剤)0.1質量部、グリセリンモノステアレート(滑剤)0.3質量部を配合して得られたポリプロピレン樹脂組成物に対して、製造例1〜10および比較製造例1〜6で得られたリン酸アミン塩難燃剤組成物を表1〜3記載の配合量(質量部)で添加して実施例1〜15および比較例1〜9の難燃性合成樹脂組成物を得た。なお、表1〜3には、リン酸アミン塩組成物中のアンモニウムカチオンの含有量を併記した。
得られた試験片を垂直に保ち、下端にバーナーの火を10秒間接炎させた後で炎を取り除き、試験片に着火した火が消える時間を測定した。次に、火が消えると同時に2回目の接炎を10秒間行ない、1回目と同様にして着火した火が消える時間を測定した。また、落下する火種により試験片の下の綿が着火するか否かについても同時に評価した。1回目と2回目の燃焼時間、および綿着火の有無等から、UL−94V規格にしたがって燃焼ランクをつけた。燃焼ランクはV−0が最も難燃性に優れ、V−1、V−2となるにしたがって難燃性は低下し、NRが最も難燃性に劣る。
得られた試験片を、サンシャインウェザーメーター(スガ試験機(株)製)、雨有り、ブラックパネル温度63℃で600時間まで耐候性促進試験を行った。0時間(初期値)と、600時間における試験片の黄色度(YI)、黄変度(ΔYI)を測定した。黄変度(ΔYI)の値が小さいほど耐候着色性に優れる。
Claims (9)
- リン酸アミン塩を1種以上含有するリン酸アミン塩組成物であって、アンモニウムカチオンの含有量が、100〜2000質量ppmであることを特徴とするリン酸アミン塩組成物。
- 前記リン酸アミン塩組成物中のアミンが、メラミンである請求項1記載のリン酸アミン塩組成物。
- 前記リン酸アミン塩組成物中のアミンが、ピペラジンである請求項1記載のリン酸アミン塩組成物。
- 請求項2記載のリン酸アミン塩組成物(A)と、請求項3記載のリン酸アミン塩組成物(B)と、の混合物であるリン酸アミン塩組成物。
- 前記リン酸アミン塩組成物(A)と、前記リン酸アミン塩組成物(B)と、の含有比率が、質量比で、(A)/(B)=20/80〜80/20の範囲内である請求項4記載のリン酸アミン塩組成物。
- 請求項1〜5のうちいずれか一項記載のリン酸アミン塩組成物を含有することを特徴とするリン酸アミン塩難燃剤組成物。
- 合成樹脂に対し、請求項6記載のリン酸アミン塩難燃剤組成物が配合されたことを特徴とする難燃性合成樹脂組成物。
- 前記合成樹脂が、ポリオレフィン系樹脂である請求項7記載の難燃性合成樹脂組成物。
- 請求項7または8記載の難燃性合成樹脂組成物から得られることを特徴とする成形体。
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