JPH03229790A - Flame-retardant for use in organic polymer substance - Google Patents
Flame-retardant for use in organic polymer substanceInfo
- Publication number
- JPH03229790A JPH03229790A JP2357590A JP2357590A JPH03229790A JP H03229790 A JPH03229790 A JP H03229790A JP 2357590 A JP2357590 A JP 2357590A JP 2357590 A JP2357590 A JP 2357590A JP H03229790 A JPH03229790 A JP H03229790A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- organic polymer
- integer
- flame
- formulas
- 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 26
- 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 24
- 239000000126 substance Substances 0.000 title claims abstract description 24
- 229920000620 organic polymer Polymers 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 125000002723 alicyclic group Chemical group 0.000 claims abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims 1
- 238000013508 migration Methods 0.000 abstract description 5
- 230000005012 migration Effects 0.000 abstract description 5
- 238000013329 compounding Methods 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- -1 amine compound Chemical class 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QEZIKGQWAWNWIR-UHFFFAOYSA-N antimony(3+) antimony(5+) oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[Sb+3].[Sb+5] QEZIKGQWAWNWIR-UHFFFAOYSA-N 0.000 description 3
- VSXGXPNADZQTGQ-UHFFFAOYSA-N oxirane;phenol Chemical class C1CO1.OC1=CC=CC=C1 VSXGXPNADZQTGQ-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical class C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 229920013716 polyethylene resin Polymers 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RRWFUWRLNIZICP-UHFFFAOYSA-N 1-bromo-2-phenoxybenzene Chemical compound BrC1=CC=CC=C1OC1=CC=CC=C1 RRWFUWRLNIZICP-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
- BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 description 1
- FIGPGTJKHFAYRK-UHFFFAOYSA-N 2,6-dibromo-4-methylphenol Chemical compound CC1=CC(Br)=C(O)C(Br)=C1 FIGPGTJKHFAYRK-UHFFFAOYSA-N 0.000 description 1
- DYBIGIADVHIODH-UHFFFAOYSA-N 2-nonylphenol;oxirane Chemical compound C1CO1.CCCCCCCCCC1=CC=CC=C1O DYBIGIADVHIODH-UHFFFAOYSA-N 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- HXHUXDFESWYWCW-UHFFFAOYSA-N 3a,7a-dibromo-4,5-dihydro-2-benzofuran-1,3-dione Chemical compound C1CC=CC2(Br)C(=O)OC(=O)C21Br HXHUXDFESWYWCW-UHFFFAOYSA-N 0.000 description 1
- SXUYMVGIWILPGM-UHFFFAOYSA-N 3a,7a-dichloro-4,5-dihydro-2-benzofuran-1,3-dione Chemical compound C1CC=CC2(Cl)C(=O)OC(=O)C21Cl SXUYMVGIWILPGM-UHFFFAOYSA-N 0.000 description 1
- NICWCCHKIXETCO-UHFFFAOYSA-N 4,5-dibromo-2-benzofuran-1,3-dione Chemical compound BrC1=CC=C2C(=O)OC(=O)C2=C1Br NICWCCHKIXETCO-UHFFFAOYSA-N 0.000 description 1
- GAIPRQZXSYSCRD-UHFFFAOYSA-N 4,5-dichloro-2-benzofuran-1,3-dione Chemical compound ClC1=CC=C2C(=O)OC(=O)C2=C1Cl GAIPRQZXSYSCRD-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- WPSWDCBWMRJJED-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;oxirane Chemical compound C1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WPSWDCBWMRJJED-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- BTQLWKNIJDKIAB-UHFFFAOYSA-N 6-methylidene-n-phenylcyclohexa-2,4-dien-1-amine Chemical compound C=C1C=CC=CC1NC1=CC=CC=C1 BTQLWKNIJDKIAB-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- LGXPLAABMYCEMI-UHFFFAOYSA-N C1CO1.BrC1=C(C(=C(C=C1)O)Br)Br Chemical compound C1CO1.BrC1=C(C(=C(C=C1)O)Br)Br LGXPLAABMYCEMI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- YUWBVKYVJWNVLE-UHFFFAOYSA-N [N].[P] Chemical compound [N].[P] YUWBVKYVJWNVLE-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は有機高分子物質用難燃剤（以下、難燃剤という
）に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a flame retardant for organic polymer substances (hereinafter referred to as a flame retardant).
［従来の技術］
従来のＨ燃剤としては、例えばハロゲン含有化合物、り
ん含有化合物、りん窒素含有化合物等が使用され、同時
に二酸化アンチモン、酸化モリブデン、等の難燃助剤が
併用される。[Prior Art] As conventional H flame agents, for example, halogen-containing compounds, phosphorus-containing compounds, phosphorus-nitrogen-containing compounds, etc. are used, and at the same time, flame retardant aids such as antimony dioxide, molybdenum oxide, etc. are used in combination.
［発明が解決しようとする課題］
しかしながら、このような従来の難燃剤には、（イ）有
機高分子物質との相溶性が悪く、均一混和が得られず潜
在的な難燃化能が発揮されず、有機高分子物質の物性に
悪影響をおよぼす、（ロ）難燃剤が有機高分子物質中で
移行性が大きい、
（ハ）有機高分子物質の成型加工時および加工品の機械
的性質に悪影響をおよぼす、
（勾有機高分子物質中に存在する他の添加剤、例えば可
塑剤、滑剤、酸化防止剤、着色剤、安定剤、紫外線吸収
剤等の作用を阻害する、という問題点があった。[Problems to be solved by the invention] However, such conventional flame retardants (a) have poor compatibility with organic polymer substances, making it difficult to achieve uniform mixing and exerting their latent flame retardant ability; (b) The flame retardant has a high migration property in the organic polymeric material; (c) The mechanical properties of the processed product are affected during the molding process of the organic polymeric material. There are problems in that they may have an adverse effect (inhibit the effects of other additives present in the organic polymeric material, such as plasticizers, lubricants, antioxidants, colorants, stabilizers, ultraviolet absorbers, etc.). Ta.
本発明は、これらの問題点について検討し、耐熱性、相
溶性が良く、機械的性質の低下防止に優れた難燃剤を提
供することを課題とするものである。The present invention examines these problems and aims to provide a flame retardant that has good heat resistance and compatibility, and is excellent in preventing deterioration of mechanical properties.
〔課題を解決するための手段〕
本願発明は、下記一般式（１）で表わされる化合物を有
効成分とする難燃剤を要旨とするものである。[Means for Solving the Problems] The gist of the present invention is a flame retardant containing a compound represented by the following general formula (1) as an active ingredient.
（１）
本発明の一般式（１）で表される難燃剤としては、ハロ
ゲン化無水フタール酸及び／又はハロゲン化テトラハイ
ドロ無水フタール酸４モルと、モノ置換アミン化合物、
ジ置換アミン化合物、アルコール及び／又はフェノール
２モルとジオール化合物１モルとを不活性溶媒中で反応
せしめた後、さらにジアミノ化合物を加え脱水反応せし
めることにより得られる化合物が挙げられる。(1) The flame retardant represented by the general formula (1) of the present invention includes 4 mol of halogenated phthalic anhydride and/or halogenated tetrahydrophthalic anhydride, a monosubstituted amine compound,
Examples include compounds obtained by reacting 2 moles of a di-substituted amine compound, alcohol and/or phenol with 1 mole of a diol compound in an inert solvent, and then adding a diamino compound and causing a dehydration reaction.
かかるハロゲン化無水フタール酸、ハロゲン化テトラハ
イドロ無水フタール酸とは、例えばテトラクロル無水フ
タール酸、テトラブロモ無水フタール酸、ジクロル無水
フタール酸、ジブロモ無水フタール酸、ジブロモテトラ
ハイドロ無水フタール酸、ジクロロテトラハイドロ無水
フタール酸等である。Examples of such halogenated phthalic anhydride and halogenated tetrahydrophthalic anhydride include tetrachlorophthalic anhydride, tetrabromophthalic anhydride, dichlorophthalic anhydride, dibromophthalic anhydride, dibromotetrahydrophthalic anhydride, and dichlorotetrahydrophthalic anhydride. Acids etc.
モノ置換アミン化合物、ジ置換アミン化合物とは、例え
ばジエチルアミン、ジイソプロパツールアミン、ｎ−ブ
チルアミン、ヘキシルアミン、オクチルアミン、ジラウ
リルアミン、ステアリルアミン等である。Examples of the mono-substituted amine compound and di-substituted amine compound include diethylamine, diisopropanolamine, n-butylamine, hexylamine, octylamine, dilaurylamine, and stearylamine.
アルコールとは、例えば、トリブロモフェノールエチレ
ンオキサイド付加物、ペンタクロルフェノールエチレン
オキサイド付加物、ノニルフェノールエチレンオキサイ
ド付加物、インプロペニルフェノールエチレンオキサイ
ド付加物、スチレン化フェノールエチレンオキサイド付
加物、ジブロモノニルフェノールエチレンオキサイド付
加物、フェノールエチレンオキサイド付加物、クレゾー
ルエチレンオキサイド付加物、ジブロモクレゾールエチ
レンオキサイド付加物、メタノール、エタノール、イソ
プロパツール、ｎ−ブタノール、インブタノール、ペン
タノール、ヘキサノール等である。Alcohol includes, for example, tribromophenol ethylene oxide adduct, pentachlorophenol ethylene oxide adduct, nonylphenol ethylene oxide adduct, impropenylphenol ethylene oxide adduct, styrenated phenol ethylene oxide adduct, dibromononylphenol ethylene oxide adduct. , phenol ethylene oxide adduct, cresol ethylene oxide adduct, dibromocresol ethylene oxide adduct, methanol, ethanol, isopropanol, n-butanol, imbutanol, pentanol, hexanol and the like.
フェノールとは例えば、フェノール、クレゾール、トリ
ブロモフェノール、トリクロルフェノール、ジブロモク
レゾール、ノニルフェノール、スチレン化フェノール、
イソプロペニルフェノール、０−セカンダリ−ブチルフ
ェノール等である。Phenols include, for example, phenol, cresol, tribromophenol, trichlorophenol, dibromocresol, nonylphenol, styrenated phenol,
These include isopropenylphenol, 0-secondary-butylphenol, and the like.
ジオール化合物とは、例えばエチレングリコール、１．
４ブタンジオール、１．６ヘキサンジオール、ビスフェ
ノールＡエチレンオキサイド付加物、テトラブロモビス
フェノールＡエチレンオキサイド１〜６モル付加物、テ
トラクロロビスフェノールＡエチレンオキサイド１〜６
モル付加物、ジオキシジフェニルスルホンエチレンオキ
サイド１〜６モル付加物、テトラブロモビスフェノール
Ａブチレンオキサイド１〜６モル付加物、ジヒドロキシ
ジフェニルメタンエチレンオキサイド１〜６モル付加物
、ジヒドロキシフェニルエーテルブチレンオキサイド１
〜６モル付加物等である。Diol compounds include, for example, ethylene glycol, 1.
4-butanediol, 1.6-hexanediol, bisphenol A ethylene oxide adduct, tetrabromobisphenol A ethylene oxide 1-6 mole adduct, tetrachlorobisphenol A ethylene oxide 1-6
molar adduct, dioxydiphenyl sulfone ethylene oxide 1-6 molar adduct, tetrabromobisphenol A butylene oxide 1-6 molar adduct, dihydroxydiphenylmethane ethylene oxide 1-6 molar adduct, dihydroxyphenyl ether butylene oxide 1
~6 molar adducts, etc.
さらにジアミノ化合物とは、例えばエチレンジアミン、
プロピレンジアミン、ヘキサメチレンジアミン、フェニ
レンジアミン、メチレンビスフェニルアミン、シクロへ
キシルジアミン、ジアミノジフェニルエーテル、ジアミ
ノジフェニルスルホン、イソプロピリデンジアミノジフ
ェニル等である。Furthermore, diamino compounds include, for example, ethylenediamine,
These include propylene diamine, hexamethylene diamine, phenylene diamine, methylene bisphenylamine, cyclohexyl diamine, diaminodiphenyl ether, diaminodiphenylsulfone, isopropylidene diaminodiphenyl, and the like.
また、本発明に使用する不活性溶媒は、例えばキシレン
、トルエン、ジメチルホルムアミド、ジメチルアセトア
ミド、ベンゼン、シクロヘキサン、ジメチルスルホンオ
キサイド等であり、これらを二種以上混合して使用して
もよい。In addition, the inert solvent used in the present invention is, for example, xylene, toluene, dimethylformamide, dimethylacetamide, benzene, cyclohexane, dimethylsulfone oxide, etc., and two or more of these may be used as a mixture.
次に、本発明の一般式（１）で表される難燃剤を使用し
つる対象となる有機高分子物質としては例えば、ポリス
チレン樹脂、ポリエチレン樹脂、ポリプロピレン樹脂、
ＡＢＳ樹脂、アクリル系樹脂、塩化ビニル樹脂、ポリフ
ェニレンオキシド樹脂、ポリカーボネート樹脂、ポリア
ミド樹脂、飽和または不飽和ポリエステル樹脂、メラミ
ン樹脂、エポキシ樹脂、フェノール樹脂、セルローズ系
物質等が挙げられる。Next, examples of organic polymer substances to be treated using the flame retardant represented by the general formula (1) of the present invention include polystyrene resin, polyethylene resin, polypropylene resin,
Examples include ABS resin, acrylic resin, vinyl chloride resin, polyphenylene oxide resin, polycarbonate resin, polyamide resin, saturated or unsaturated polyester resin, melamine resin, epoxy resin, phenol resin, and cellulose-based substances.
また本発明の一般式（１）で表される難燃剤の添加量は
、有機高分子物質に対して任意であり、好ましくは２〜
５０重量％である。Further, the amount of the flame retardant represented by the general formula (1) of the present invention is arbitrary with respect to the organic polymer substance, and is preferably 2 to 2.
It is 50% by weight.
本発明の一般式で表される難燃剤の添加時期は、有機高
分子物質の重合時、成型時、または紡糸時等その他いず
れの時期でも可能であり、また添加型態は、一般式（１
）で表される難燃剤をそのままで、または溶媒に溶解し
た形態で、または水中もしくは油類に分散させエマルジ
ョン形態で添加する。The flame retardant represented by the general formula of the present invention can be added at any time such as during polymerization of the organic polymer substance, molding, or spinning.
) is added as is, dissolved in a solvent, or dispersed in water or oil and added in the form of an emulsion.
本発明においては、本発明の一般式（１）で表される難
燃剤と共に必要に応じて、他の難燃剤および難燃助剤、
例えば含ハロゲンアルキルホスフェート、含ハロゲンホ
スファイト、金属酸化物、金属水酸化物及びアルキル金
属化合物等を併用することが可能であり、さらにその他
の添加剤、例えば安定剤、着色剤、耐候剤、紫外線吸収
剤、艶消剤、帯電防止剤、増量剤等を併用することも可
能である。In the present invention, in addition to the flame retardant represented by the general formula (1) of the present invention, other flame retardants and flame retardant aids,
For example, halogen-containing alkyl phosphates, halogen-containing phosphites, metal oxides, metal hydroxides, alkyl metal compounds, etc. can be used in combination, and other additives such as stabilizers, colorants, weathering agents, ultraviolet rays, etc. It is also possible to use an absorbent, a matting agent, an antistatic agent, a filler, etc. in combination.
Ｃ作用〕
本発明の一般式（１）で表される難燃剤を有機高分子物
質に使用した場合、難燃性に優れ、相溶性、耐候性およ
び耐熱性に優れ、有機高分子物質中での移行性が非常に
小さく、有機高分子物質の成型加工時および加工品の機
械的性質に悪影響をおよぼさない、さらに電気特性も低
下させない等のすぐれた特徴を示す。C effect] When the flame retardant represented by the general formula (1) of the present invention is used in an organic polymer substance, it has excellent flame retardancy, compatibility, weather resistance, and heat resistance, and It exhibits excellent characteristics such as very low migration, and does not adversely affect the mechanical properties of processed products during molding of organic polymeric substances, and does not deteriorate electrical properties.
したがって、本発明の一般式（１）で表される難燃剤を
使用した難燃性有機高分子物質は樹脂成型品、フィルム
、発泡体、塗料等の被覆材、繊維伏物、積層材、その他
の高分子材料等に使用することが可能である。Therefore, the flame-retardant organic polymeric substance using the flame retardant represented by the general formula (1) of the present invention can be used in resin molded products, films, foams, coating materials such as paints, fiber coverings, laminated materials, etc. It can be used for polymer materials, etc.
〔実施例］ 以下に本発明の実施例をかかげる。〔Example] Examples of the present invention are listed below.
実施例１
撹拌機、冷却コンデンサー、温度計、滴下ロートを有す
る四ツロフラスコ中にテトラブロモ無水フタル酸１８５
．６ｇ、キシレン２００ｇ、ジメチルホルムアミド７０
ｇを加え、８０〜１００℃に加熱撹拌し自溶物が溶解し
た後、フェノールエチレンオキシド（１モル）付加物２
７．６ｇ、エチレングリコール６．２ｇを加え１００〜
１３０℃、３時間加熱撹拌する。Example 1 Tetrabromo phthalic anhydride 185 in a four-way flask with a stirrer, cooling condenser, thermometer, and dropping funnel.
．． 6g, xylene 200g, dimethylformamide 70g
g, and heated and stirred at 80 to 100°C to dissolve the self-soluble material, and then add phenol ethylene oxide (1 mol) adduct 2.
Add 7.6g and 6.2g of ethylene glycol to 100~
Heat and stir at 130°C for 3 hours.
次いでエチレンジアミン１２．０ｇを加え、１２０〜１
３５℃に加熱撹拌し窒素気流下で反応し、溜出水７．２
ｇを確認した後、窒素ガスの通人を止め、減圧にて溶媒
を留去する。反応生成物を常温に冷却後２倍量のメタノ
ールを加え反応生成物を洗浄後濾別、乾燥し含ハロゲン
アミドエステル化合物２２０ｇ （理論値２２４．２ｇ
）を得た。Next, 12.0 g of ethylenediamine was added, and the
Heat to 35°C with stirring, react under nitrogen stream, distilled water 7.2
After confirming g, the flow of nitrogen gas is stopped, and the solvent is distilled off under reduced pressure. After cooling the reaction product to room temperature, twice the amount of methanol was added, and the reaction product was washed, filtered, and dried to obtain 220 g of a halogen-containing amide ester compound (theoretical value: 224.2 g).
) was obtained.
Ｂｒ％ ５６．１０（理論値５５．３０）５０％分解点
４６４℃
Ｍ、ｐ ３０６ ℃
実施例２
撹拌機、冷却コンデンサー、温度計１滴下ロートを有す
る四ツロフラスコ中にテトラブロモ無水フタール酸１８
５．６ｇ、キシレン２００ｇ、ジメチルホルムアミド８
０ｇを加え８０〜１００℃に加熱撹拌し、内容物が溶解
した後、ジブロモクレゾールエチレンオキサイド（１モ
ル）付加物６１．４ｇ、テトラブロモビスフェノールＡ
エチレンオキサイド（２モル）付加物６３．２ｇを加え
１００℃〜１３０℃で３時間加熱撹拌する。Br% 56.10 (theoretical value 55.30) 50% decomposition point 464°C M, p 306°C Example 2 Tetrabromo-phthalic anhydride 18 in a four-way flask with a stirrer, cooling condenser, thermometer and 1 dropping funnel.
5.6g, xylene 200g, dimethylformamide 8
After the contents were dissolved, 61.4 g of dibromocresol ethylene oxide (1 mol) adduct and tetrabromobisphenol A were added.
Add 63.2 g of ethylene oxide (2 mol) adduct and heat and stir at 100°C to 130°C for 3 hours.
次いで、エチレンジアミン１２．９ｇを加え１２０〜１
３５℃に加熱撹拌し、窒素気流下で反応し、溜出水７．
２ｇを確認した後窒素ガスの通人を止め減圧にて溶媒を
留去する。反応生成物を常温に冷却後２倍量のメチルエ
チルケトンにより反応生成物を洗浄し、濾別乾燥する。Next, 12.9 g of ethylenediamine was added and
Heat to 35°C with stirring, react under nitrogen stream, and add distilled water7.
After confirming 2 g, the flow of nitrogen gas was stopped and the solvent was distilled off under reduced pressure. After cooling the reaction product to room temperature, the reaction product is washed with twice the amount of methyl ethyl ketone, filtered and dried.
含ハロゲンアミドエステル化合物３０８ｇ（理論値３１
５ｇ）を得た。308g of halogen-containing amide ester compound (theoretical value: 31
5g) was obtained.
Ｂｒ％ ６１．２０ （理論値６０．９５）Ｍ、ｐ
３０３．６℃
５０％分解点４６１．９℃
実施例３
ＡＢＳ樹脂１００ｇに難燃剤２０ｇおよび二酸化アンチ
モン５ｇを加え、２００℃で６分間混練した後テストピ
ースを作成し、難燃生を測定した。結果を第１表に示す
。Br% 61.20 (theoretical value 60.95) M, p
303.6°C 50% decomposition point 461.9°C Example 3 20g of flame retardant and 5g of antimony dioxide were added to 100g of ABS resin, and after kneading at 200°C for 6 minutes, a test piece was prepared and flame retardancy was measured. The results are shown in Table 1.
第 表 注−１： （ １／８” ） に従って行なっ た。No. table Note-1: ( 1/8" ) do according to Ta.
注−２二デ力ブロモジフエニルエーテル実施例４
ポリエチレン樹脂１００ｇに難燃剤■Ｏｇ、および三酸
化アンチモン３ｇを加え、１７０℃で混練した後、テス
トピースを作成し、難燃性および移行性を測定した。結
果を第２表に示す。Note-2 Two-dimensional bromodiphenyl ether Example 4 Flame retardant ■Og and 3 g of antimony trioxide were added to 100 g of polyethylene resin, and after kneading at 170°C, a test piece was prepared and the flame retardance and migration properties were evaluated. It was measured. The results are shown in Table 2.
第 ２ 表 注−３： Ｊ Ｉ ５Ｋ−７２０１に従って行なった。Table 2 Note-3: Conducted in accordance with JI 5K-7201.
注−４：テストピース１５０Ｘ３．ＯＸ５０ｍｎ＋を７
０℃の温度に１６８時間曝露し、
次いで肉眼で判定した。Note-4: Test piece 150X3. OX50mn+7
Exposure to a temperature of 0°C for 168 hours followed by visual judgment.
実施例５
１日ポリスチレン樹脂１００ｇに難燃剤１５ｇ、および
二酸化アンチモン３ｇを加え、２００℃で６分間混練し
た後テストピースを作成し、難燃性および耐候性を測定
した。結果を第３表に示す。Example 5 1 day 15 g of flame retardant and 3 g of antimony dioxide were added to 100 g of polystyrene resin, and the mixture was kneaded at 200° C. for 6 minutes, then test pieces were prepared and flame retardancy and weather resistance were measured. The results are shown in Table 3.
〔発明の効果］
以上説明し、かつ実証した通り、本発明の一般式で表さ
れる難燃剤は、有機高分子物質に使用した場合、難燃性
、相溶性、耐候性および耐熱性に優れ、有機高分子物質
中での移行性が非常に小さく、有機高分子物質の成型加
工時および加工品の機械的性質に悪影響をおよぼさない
、さらに電気特性も低下させない等のすぐれた特徴を示
すことにより、関連産業の発展及び対火災安全性の向上
に貢献しつる。[Effects of the Invention] As explained and demonstrated above, the flame retardant represented by the general formula of the present invention has excellent flame retardancy, compatibility, weather resistance, and heat resistance when used in organic polymer substances. It has excellent characteristics such as very low migration in organic polymeric materials, no adverse effects on the mechanical properties of processed products during molding of organic polymeric materials, and no deterioration of electrical properties. By demonstrating this, we will contribute to the development of related industries and the improvement of fire safety.
Claims (1)
とする有機高分子物質用難燃剤。▲数式、化学式、表等
があります▼ ・・・（１） 〔式中、Ａは ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼又はＲ＿４Ｏ−、 Ｒ＿１はＨ、ＣＨ＿３又は芳香族核、 Ｒ＿２はＨ、Ｃ＿１〜＿９アルキル基、▲数式、化学式
、表等があります▼、Ｂｒ又はＣｌ、 Ｒ＿３はＣ＿２〜＿６のアルキル基又はアルケニル基、 Ｒ＿４はＣ＿１〜＿１＿８のアルキル基又は▲数式、化
学式、表等があります▼、ＹはＢｒ、Ｃｌ、ＣＨ＿３又
はＨ、 Ｓは１〜５の整数、Ｔは０〜５の整数、 ｕは０〜６の整数、Ｖは１〜２の整数、 Ｗは０〜１の整数、ＸはＣｌ又はＢｒ、 ｍは１〜４の整数、 Ｒ＿５はＣ＿１〜＿６のアルキレン基、芳香族核、脂環
族環又は▲数式、化学式、表等があります▼ Ｂは−ＯＣ＿ｎＨ＿２＿ｎＯ−又は ▲数式、化学式、表等があります▼、 Ｄは−ＣＨ＿２−、−ＳＯ＿２−、−Ｏ−又は▲数式、
化学式、表等があります▼、ｎは１〜６の整数、 Ｌは１〜６の整数を、それぞれ示す。〕(1) A flame retardant for organic polymer substances containing a compound represented by the following general formula (1) as an active ingredient. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ... (1) [In the formula, A is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼ or R_4O-, R_1 is H, CH_3 or aromatic nucleus, R_2 is H, C_1-_9 alkyl group, ▲ There are numerical formulas, chemical formulas, tables, etc. ▼, Br or Cl, R_3 is C_2-_6 Alkyl group or alkenyl group, R_4 is an alkyl group of C_1 to _1_8 or ▲ has a numerical formula, chemical formula, table, etc. ▼, Y is Br, Cl, CH_3 or H, S is an integer from 1 to 5, T is an integer from 0 to 5 integer, u is an integer of 0 to 6, V is an integer of 1 to 2, W is an integer of 0 to 1, X is Cl or Br, m is an integer of 1 to 4, R_5 is an alkylene group of C_1 to_6, aromatic Group nucleus, alicyclic ring, or ▲ There are mathematical formulas, chemical formulas, tables, etc.▼ B is -OC_nH_2_nO- or ▲ There are mathematical formulas, chemical formulas, tables, etc.▼, D is -CH_2-, -SO_2-, -O-, or ▲ formula,
There are chemical formulas, tables, etc. ▼, n indicates an integer from 1 to 6, and L indicates an integer from 1 to 6, respectively. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2357590A JPH03229790A (en) | 1990-02-01 | 1990-02-01 | Flame-retardant for use in organic polymer substance |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2357590A JPH03229790A (en) | 1990-02-01 | 1990-02-01 | Flame-retardant for use in organic polymer substance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03229790A true JPH03229790A (en) | 1991-10-11 |
Family
ID=12114345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2357590A Pending JPH03229790A (en) | 1990-02-01 | 1990-02-01 | Flame-retardant for use in organic polymer substance |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03229790A (en) |
-
1990
- 1990-02-01 JP JP2357590A patent/JPH03229790A/en active Pending
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