JPH02129137A - Halogenated bis(4-phenoxyphenyl)ether and flame retardant polymer composition containing the same - Google Patents
Halogenated bis(4-phenoxyphenyl)ether and flame retardant polymer composition containing the sameInfo
- Publication number
- JPH02129137A JPH02129137A JP28142588A JP28142588A JPH02129137A JP H02129137 A JPH02129137 A JP H02129137A JP 28142588 A JP28142588 A JP 28142588A JP 28142588 A JP28142588 A JP 28142588A JP H02129137 A JPH02129137 A JP H02129137A
- Authority
- JP
- Japan
- Prior art keywords
- ether
- phenoxyphenyl
- flame retardant
- bis
- flame
- 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
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 40
- 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 29
- GQGTXJRZSBTHOB-UHFFFAOYSA-N 1-phenoxy-4-(4-phenoxyphenoxy)benzene Chemical class C=1C=C(OC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=CC=1OC1=CC=CC=C1 GQGTXJRZSBTHOB-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 229920000642 polymer Polymers 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 title claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 77
- -1 4-phenoxyphenyl Chemical group 0.000 abstract description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 12
- 229910052794 bromium Inorganic materials 0.000 abstract description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052736 halogen Inorganic materials 0.000 abstract description 5
- 150000002367 halogens Chemical group 0.000 abstract description 5
- 238000013508 migration Methods 0.000 abstract description 5
- 230000005012 migration Effects 0.000 abstract description 5
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract description 4
- 230000002140 halogenating effect Effects 0.000 abstract description 3
- 230000026030 halogenation Effects 0.000 abstract description 3
- 238000005658 halogenation reaction Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000012320 chlorinating reagent Substances 0.000 abstract description 2
- 239000011968 lewis acid catalyst Substances 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 239000002861 polymer material Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 23
- 238000002411 thermogravimetry Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 238000000465 moulding Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- 241000191368 Chlorobi Species 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 229920002681 hypalon Polymers 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920005670 poly(ethylene-vinyl chloride) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide 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
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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、新規なハロゲン化ビス(4−フェノキシフェ
ニル)エーテルおよびそれを含む難燃性高分子組成物に
関し、更に詳しくは一般式[I](式[I]中、Xはハ
ロゲン原子を表し、a、 dは1〜5の数、b、cは
1〜4の数)で表されるハロゲン化ビス(4−フェノキ
シフェニル)エーテル(以下HPPEと略す)およびそ
れを含む難燃性高分子組成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel halogenated bis(4-phenoxyphenyl) ether and a flame-retardant polymer composition containing the same. ] (In formula [I], X represents a halogen atom, a and d are numbers from 1 to 5, and b and c are numbers from 1 to 4). (hereinafter abbreviated as HPPE) and flame-retardant polymer compositions containing the same.
本発明の化合物HPPEは、高分子材料の難燃剤として
有用な化合物である。The compound HPPE of the present invention is a compound useful as a flame retardant for polymeric materials.
[従来の技術]
今日、ポリエチレン、ポリプロピレン、ポリスチレンの
ごとき可燃性樹脂を難燃化する目的でこれらの樹脂中へ
種々の難燃剤を混入することが行われている。[Prior Art] Today, various flame retardants are mixed into flammable resins such as polyethylene, polypropylene, and polystyrene for the purpose of making these resins flame retardant.
難燃剤としては、各種の含ハロゲン系難燃剤、含リン系
難燃剤、含リン含ハロゲン系難燃剤、無機化合物が知ら
れている。As flame retardants, various halogen-containing flame retardants, phosphorus-containing flame retardants, phosphorus-containing halogen-containing flame retardants, and inorganic compounds are known.
しかし一般にこれら難燃剤は、耐熱性に欠点のあるもの
が多く、高分子の成型加工時に難燃剤の熱分解により成
型加工機の腐蝕を引き起こす等の欠点を何していた。However, in general, many of these flame retardants have shortcomings in heat resistance, and the flame retardants can cause corrosion of molding machines due to thermal decomposition during polymer molding.
またこれら難燃剤は、樹脂との相溶性に乏しく、低分子
量体であるものが多く、樹脂配合組成物で長期使用中に
樹脂表面にブルームしたり、あるいは高温で揮散するこ
とがあり、そのために樹脂の難燃特性に変化を生ずる傾
向がある。In addition, these flame retardants have poor compatibility with resins and are often low molecular weight, so they may bloom on the resin surface during long-term use in resin compositions or volatilize at high temperatures. It tends to cause changes in the flame retardant properties of the resin.
[発明が解決しようとする問題点]
近年、エンジニアリングプラスチックスに代表される高
耐熱高分子が開発されるに従い、高分子の加工および使
用温度も上昇してきている。それらの耐熱性高分子を難
燃化するには、高分子が加工、使用される温度において
も、熱的に安定な難燃剤が必要となる。[Problems to be Solved by the Invention] In recent years, as highly heat-resistant polymers typified by engineering plastics have been developed, the processing and use temperatures of the polymers have also been rising. To make these heat-resistant polymers flame retardant, a flame retardant is required that is thermally stable even at the temperatures at which the polymers are processed and used.
また射出成型等の加工時に、難燃剤のマイグレーション
が起こり、金型被覆を引き起こしたり、成型体の長期使
用時に樹脂表面に難燃剤がブルームを起こす事のない高
性能な難燃剤が望まれている。In addition, there is a need for a high-performance flame retardant that will not cause migration of flame retardant during processing such as injection molding, causing mold coating, and will not cause flame retardant bloom on the resin surface during long-term use of molded products. .
本発明の目的は特に耐熱性、耐マイグレーション性に優
れた難燃剤を提供することにある。An object of the present invention is to provide a flame retardant particularly excellent in heat resistance and migration resistance.
[問題点を解決するための手段]
本発明者らは、上記事情に鑑み、各種化合物を合成し、
耐熱性、耐マイグレーション性に優れた難燃剤として好
適に使用し得る新規化合物について鋭意検討した結果、
特定のハロゲン含有化合物がかかる条件を満足すること
を見出だし、本発明に到達したのである。[Means for solving the problems] In view of the above circumstances, the present inventors synthesized various compounds,
As a result of intensive research into new compounds that can be suitably used as flame retardants with excellent heat resistance and migration resistance, we found that
The present invention was achieved by discovering that a specific halogen-containing compound satisfies these conditions.
すなわち本発明は一般式[IF
(式N]中、Xはハロゲン原子を表し、a、 dは1
〜5の数、b、cは1〜4の数)で表されるHPPEお
よびそれを含む難燃性高分子組成物に関するものである
。That is, in the present invention, in the general formula [IF (formula N), X represents a halogen atom, and a and d are 1
The present invention relates to HPPE represented by a number from 1 to 5, b and c are numbers from 1 to 4) and a flame-retardant polymer composition containing the same.
本発明のHPPEは、前記一般式N]で示される化学構
造式を有する新規化合物で、後述するようなハロゲン含
H率、融点及び赤外吸収スペクトルを示す。The HPPE of the present invention is a novel compound having a chemical structural formula represented by the general formula N], and exhibits a halogen H content, a melting point, and an infrared absorption spectrum as described below.
一般式中のXはハロゲン原子を表し、塩素、または臭素
であるが、同一分子内で塩素と臭素が混(1ミしてもよ
い。X in the general formula represents a halogen atom, and is chlorine or bromine, but chlorine and bromine may be mixed in the same molecule.
本発明の一般式[I]で表される化合物の具体例をあげ
ると、テトラブロモビス(4−フェノキンフェニル)エ
ーテル、ペンタブロモビス(4−フェノキシフェニル)
エーテル、ヘキサブロモビス(4−フェノキシフェニル
)エーテル、ヘプタブロモビス(4−フェノキシフェニ
ル)エーテル、オクタブロモビス(4−フェノキシフェ
ニル)エーテル、ノナブロモビス(4−フェノキシフェ
ニル)エーテル、デカブロモビス(4−フェノキシフェ
ニル)エーテル、ウンデカブロモビス(4−フェノキシ
フェニル)エーテル、ドデカブロモビス(4−フェノキ
シフェニル)エーテル、トリデカブロモビス(4−フェ
ノキシフェニル)ニーチル、テトラデカブロモビス(4
−フェノキシフェニル)エーテル、ペンタデカブロモビ
ス(4−フェノキシフェニル)エーテル、ヘキサデカブ
ロモビス(4−フェノキシフェニル)エーテル、ヘプタ
デカブロモビス(4−フェノキシフェニル)エーテル、
オクタデカブロモビス(4−フェノキシフェニル)エー
テル等の臭素化合物やテトラクロロビス(4−フェノキ
シフェニル)エーテル、ペンタクロロビス(4−フェノ
キンフェニル)エーテル、ヘキサクロロビス(4−フェ
ノキシフェニル)エーテル、ヘプタクロロビス(4−フ
ェノキシフェニル)エーテル、オクタクロロビス(4フ
エノキシフエニル)エーテル、ノナクロロビス(4−フ
ェノキシフェニル)エーテル、デカクロロビス(4−フ
ェノキシフェニル)エーテル、ウンデカクロロビス(4
−フェノキシフェニル)エーテル、ドデカクロロビス(
4−フェノキシフェニル)エーテル、トリデカクロロビ
ス(4−フェノキシフェニル)エーテル、テトラデカり
ロロビス(4−フェノキシフェニル)エーテル、ペンタ
デカクロロビス(4−フェノキシフェニル)エーテル、
ヘキサデカりロロビス(4−フェノキシフェニル)エー
テル、ヘプタデカりロロビス(4−フェノキシフェニル
)エーテル、オクタデカりロロビス(4−フェノキシフ
ェニル)エーテル等の塩素化合物であり、これらの混合
物でもよい。Specific examples of the compound represented by the general formula [I] of the present invention include tetrabromobis(4-phenoquinphenyl)ether, pentabromobis(4-phenoxyphenyl)
Ether, hexabromobis(4-phenoxyphenyl)ether, heptabromobis(4-phenoxyphenyl)ether, octabromobis(4-phenoxyphenyl)ether, nonabromobis(4-phenoxyphenyl)ether, decabromobis(4-phenoxyphenyl) ) ether, undecabromo bis(4-phenoxyphenyl) ether, dodecabromo bis(4-phenoxyphenyl) ether, tridecabromo bis(4-phenoxyphenyl) nityl, tetradecabromo bis(4-phenoxyphenyl) ether,
-phenoxyphenyl) ether, pentadecabromobis(4-phenoxyphenyl)ether, hexadecabromobis(4-phenoxyphenyl)ether, heptadecabromobis(4-phenoxyphenyl)ether,
Bromine compounds such as octadecabromobis(4-phenoxyphenyl)ether, tetrachlorobis(4-phenoxyphenyl)ether, pentachlorobis(4-phenoquinphenyl)ether, hexachlorobis(4-phenoxyphenyl)ether, heptachlorobis(4-phenoxyphenyl)ether, Chlorobis(4-phenoxyphenyl)ether, octachlorobis(4-phenoxyphenyl)ether, nonachlorobis(4-phenoxyphenyl)ether, decachlorobis(4-phenoxyphenyl)ether, undecachlorobis(4-phenoxyphenyl)ether
-phenoxyphenyl) ether, dodecachlorobis(
4-phenoxyphenyl) ether, tridecachlorobis(4-phenoxyphenyl)ether, tetradecaryrolobis(4-phenoxyphenyl)ether, pentadecachlorobis(4-phenoxyphenyl)ether,
These are chlorine compounds such as hexadecalyrolobis(4-phenoxyphenyl)ether, heptadecalyrolobis(4-phenoxyphenyl)ether, and octadeclyrolobis(4-phenoxyphenyl)ether, and mixtures thereof may also be used.
次に、本発明のHPPEの製造は、ビス(4−フェノキ
シフェニル)エーテルを適当な触媒の存在下、臭素、臭
素化剤、塩素、塩素化剤等のノ10ケン化試剤によりハ
ロゲン化することにより達成できる。ハロゲン化度は、
ハロゲン化試剤の量やルイス酸触媒の種類によりコント
ロールできる。Next, the production of HPPE of the present invention involves halogenating bis(4-phenoxyphenyl)ether with a saponification reagent such as bromine, a brominating agent, chlorine, or a chlorinating agent in the presence of a suitable catalyst. This can be achieved by The degree of halogenation is
It can be controlled by the amount of halogenating reagent and the type of Lewis acid catalyst.
本発明の新規化合物により難燃性を改良される高分子化
合物としては、特に制限されるものではないが、例えば
ポリエチレン、ポリプロピレン、ポリブテン、ポリ塩化
ビニル、エチレン−酢酸ビニル共重合体、エチレン−エ
チルアクリレート共重合体、エチレン−プロピレン共重
合体、エチレン−プロピレン−ジエン共重合体、エチレ
ン−塩化ビニル共重合体、エチレン−酢酸ビニル−グラ
フト塩化ビニル共重合体、エチレン−エチルアクリレー
ト−グラフト塩化ビニル共重合体、エチレン−プロピレ
ン−グラフト塩化ビニル共重合体、塩素化ポリエチレン
、塩素化ポリエチレン−グラフト塩化ビニル共重合体、
ポリスチレン、ABS。The polymer compounds whose flame retardance can be improved by the novel compound of the present invention are not particularly limited, but include, for example, polyethylene, polypropylene, polybutene, polyvinyl chloride, ethylene-vinyl acetate copolymer, ethylene-ethyl Acrylate copolymer, ethylene-propylene copolymer, ethylene-propylene-diene copolymer, ethylene-vinyl chloride copolymer, ethylene-vinyl acetate-grafted vinyl chloride copolymer, ethylene-ethyl acrylate-grafted vinyl chloride copolymer polymer, ethylene-propylene-grafted vinyl chloride copolymer, chlorinated polyethylene, chlorinated polyethylene-grafted vinyl chloride copolymer,
Polystyrene, ABS.
アクリル系樹脂、ポリメチルメタクリレート、ポリアミ
ド、ポリカーボネート、ポリフェニレンオキシド、ポリ
ブチレンテレフタレート、ポリエチレンテレフタレート
などの熱可塑性樹脂またはエラストマー、不飽和ポリエ
ステル、ポリウレタン、エポキシ樹脂、フェノール樹脂
、メラミン樹脂、尿素樹脂などの熱硬化性樹脂およびブ
チルゴム、クロロプレインゴム、ニトリルゴム、天然ゴ
ム、シリコンゴム、クロロスルホン化ポリエチレン、ス
チレン−ブタジェンゴム、ポリエステル−エーテルエラ
ストマーなどが例示される。これらの高分子は一種単独
で用いても、二種以上を併用してもよい。Thermosetting of thermoplastic resins or elastomers such as acrylic resin, polymethyl methacrylate, polyamide, polycarbonate, polyphenylene oxide, polybutylene terephthalate, polyethylene terephthalate, unsaturated polyester, polyurethane, epoxy resin, phenolic resin, melamine resin, urea resin, etc. Examples include rubber resins, butyl rubber, chloroprene rubber, nitrile rubber, natural rubber, silicone rubber, chlorosulfonated polyethylene, styrene-butadiene rubber, and polyester-ether elastomer. These polymers may be used alone or in combination of two or more.
本発明の難燃剤の添加量は、それぞれの対象高分子化合
物によっても異なるが、通常高分子化合物100重量部
に対して1重量部以上、好ましくは1〜100重量部程
重量過程である。The amount of the flame retardant of the present invention added varies depending on each target polymer compound, but is usually 1 part by weight or more, preferably 1 to 100 parts by weight, per 100 parts by weight of the polymer compound.
本発明の難燃剤の高分子化合物への添加方法は任意であ
り特に規定されないが、例えば高分子と難燃剤を共にチ
ップ状で、もしくは粉末状で混合する方法、その混合物
を溶融成型する方法、あるいは高分子と難燃剤をそれぞ
れ溶液状態にしたあと混合し、ついで貧溶媒で再沈させ
たり、溶媒を蒸発せしめる方法等があげられる。The method of adding the flame retardant of the present invention to the polymer compound is arbitrary and not particularly specified, but for example, a method of mixing the polymer and the flame retardant together in the form of chips or powder, a method of melt-molding the mixture, Alternatively, the polymer and the flame retardant may be put into a solution state, mixed, and then reprecipitated with a poor solvent, or the solvent may be evaporated.
また本発明の新規化合物を難燃剤として利用する場合、
難燃効果を高める目的で三酸化アンチモン等の難燃助剤
や他の公知の難燃剤を併用してもよい。また酸化防止剤
、着色剤、紫外線吸収剤、安定剤、充填剤、帯電防止剤
等の公知の添加剤も併用することができる。Furthermore, when using the novel compound of the present invention as a flame retardant,
In order to enhance the flame retardant effect, a flame retardant aid such as antimony trioxide or other known flame retardants may be used in combination. Further, known additives such as antioxidants, colorants, ultraviolet absorbers, stabilizers, fillers, and antistatic agents can also be used.
[発明の効果]
本発明の新規化合物は、高分子化合物に対して優れた難
燃性を付与する。また耐熱性に優れており、5%の加熱
重量減温度は390℃以上であり殆どの高分子化合物へ
適用でき、成型加工時の熱分解や蒸発揮散は認められな
い。[Effects of the Invention] The novel compound of the present invention imparts excellent flame retardancy to polymer compounds. It also has excellent heat resistance, and the weight loss temperature at 5% heating is 390°C or higher, so it can be applied to most polymeric compounds, and no thermal decomposition or evaporation is observed during molding.
また成型加工後、高分子表面への本化合物のブルームは
認められないため、長期に亘って安定した難燃特性を発
現できる。Furthermore, since no blooming of the compound on the polymer surface is observed after the molding process, stable flame retardant properties can be exhibited over a long period of time.
[実施例]
以下実施例によりさらに説明するが、本発明はこれらに
限定されるものではない。[Examples] The present invention will be further explained below with reference to Examples, but the present invention is not limited thereto.
(実施例1)
オクタデカブロモビス(4−フェノキシフェニル)エー
テルの合成
臭化水素トラップ付き冷却コンデンサーおよび攪拌羽根
を装備した200m1丸底フラスコに、臭素69.3g
、1.2−ジクロロエタン40m1および塩化アルミニ
ウム0.4gを入れ、50℃に加熱し攪拌した。次にこ
の臭素溶液にビス(4−フェノキシフェニル)エーテル
4.26gを1,2−ジクロロエタン80m1に溶解し
た液を2.3時間にわたり滴下した。続いて反応液を昇
温し、臭素還、流下で2゜5時間熟成を行った。(Example 1) Synthesis of octadecabromobis(4-phenoxyphenyl)ether 69.3 g of bromine was placed in a 200 ml round bottom flask equipped with a cooling condenser with a hydrogen bromide trap and a stirring blade.
, 40 ml of 1,2-dichloroethane and 0.4 g of aluminum chloride were added, and the mixture was heated to 50°C and stirred. Next, a solution prepared by dissolving 4.26 g of bis(4-phenoxyphenyl)ether in 80 ml of 1,2-dichloroethane was added dropwise to this bromine solution over 2.3 hours. Subsequently, the reaction solution was heated, refluxed with bromine, and aged for 2.5 hours under flowing conditions.
反応終了後、室温まで冷却し水80m1を添加し、加熱
することにより臭素、1.2−ジクロロエタンを留去し
た。After the reaction was completed, the mixture was cooled to room temperature, 80 ml of water was added, and bromine and 1,2-dichloroethane were distilled off by heating.
冷却後、iすられたスラリーを濾過し、水洗を行い、1
50℃で6時間乾燥して、白色固体20゜68gを得た
。(収率97.1%)
下記の分析結果よりオクタデカブロモビス(4−フェノ
キシフェニル)エーテルであることを確認した。併せて
、本化合物の熱安定性を熱重量分析(TGA)でAl1
定した結果も示す。After cooling, the slurry was filtered and washed with water.
After drying at 50° C. for 6 hours, 20°68 g of a white solid was obtained. (Yield 97.1%) From the analysis results below, it was confirmed that it was octadecabromobis(4-phenoxyphenyl)ether. In addition, the thermal stability of this compound was determined by thermogravimetric analysis (TGA).
The results are also shown.
元素分析値
実測値(%) 理論値(%)
C−16,3116,24
H−<0.05 0.00
Br−81,1081,05
融点 * 1 375℃
質量分析スペクトル
Mass(m/e) 1774(M+)熱重量分析
*2
加熱重量減(重量%) 温度(”C)*1;示差熱分
析による
*2;分析条件
雰囲気 空気
ガス流量 30.5ml/min
昇温速度 10℃/ m i n
測定温度 室温〜500℃
(実施例2)
デカブロモビス(4−フェノキシフェニル)エーテルの
合成
臭化水素トラップ付き冷却コンデンサーおよび攪拌羽根
を装備した3fI丸底フラスコに、ジクロロメタン80
0m l、 ビス(4−フェノキンフェニル)エーテ
ル90.ogおよび鉄粉1.89gを入れ、加熱し攪拌
した。40℃加熱還流下の本溶液に臭素487.6gを
7時間にわたり滴下し、その後同温度で1時間熟成を行
った。Elemental analysis value Actual value (%) Theoretical value (%) C-16,3116,24 H-<0.05 0.00 Br-81,1081,05 Melting point * 1 375°C Mass spectrometry spectrum Mass (m/e) 1774 (M+) Thermogravimetric analysis *2 Heating weight loss (weight%) Temperature ("C) *1; By differential thermal analysis *2; Analysis conditions Atmosphere Air gas flow rate 30.5 ml/min Heating rate 10°C/m i n Measurement temperature Room temperature to 500°C (Example 2) Synthesis of decabromobis(4-phenoxyphenyl)ether A 3fI round bottom flask equipped with a cooling condenser with a hydrogen bromide trap and a stirring blade was charged with dichloromethane 80°C.
0ml, bis(4-phenoquinphenyl)ether 90. og and 1.89 g of iron powder were added, heated and stirred. 487.6 g of bromine was added dropwise to the solution under reflux at 40° C. over 7 hours, and then aged at the same temperature for 1 hour.
反応終了後、室温まで冷却し水1gを添加し、加熱する
ことにより臭素、ジクロロメタンを留去した。After the reaction was completed, the mixture was cooled to room temperature, 1 g of water was added, and bromine and dichloromethane were distilled off by heating.
冷却後、得られたスラリーを濾過し、水洗を行い、クロ
ロホルムで再結晶して、白色固体268゜8gを?すた
。(収率92.6%)
ド記の分析結果よりデカブロモビス(4−フェノキンフ
ェニル)エーテルであることを確認した。After cooling, the resulting slurry was filtered, washed with water, and recrystallized with chloroform to obtain 268.8 g of a white solid. Star. (Yield 92.6%) From the analysis results described above, it was confirmed that it was decabromobis(4-phenoquinphenyl)ether.
併仕で、本化合物の熱安定性を熱重量分析(TGA)で
Δp1定した結果も示す。In addition, the results of determining Δp1 of the thermal stability of this compound by thermogravimetric analysis (TGA) are also shown.
元素分析値
実測値(%) 理論値(%)
C−25,3025,21
H−0,720,71
Br=69.75 69.88
融点 249〜253℃
質量分析スペクトル
Mass(m/e) 1143(M+)熱重量分析
加熱重量減(重量%) 温度(”C)(実施例3)
オクタブロモビス(4−フェノキシフェニル)エーテル
の合成
臭化水素トラップ付き冷却コンデンサーおよび攪拌羽根
を装備した1Ω丸底フラスコに、臭素650gと五塩化
アンチモン15.19gを入れ、加熱し攪拌した。59
℃加熱還流下の本溶液にビス(4−フェノキシフェニル
)エーテル90.0gをクロロホルム180m1に溶か
した液を3時間にわたり滴下し、その後同温度で1時間
熟成を行った。反応終了後、室温まで冷却し水300m
1を添加し、加熱することにより臭素、クロロホルムを
留去した。Actual elemental analysis value (%) Theoretical value (%) C-25,3025,21 H-0,720,71 Br=69.75 69.88 Melting point 249-253°C Mass spectrometry spectrum Mass (m/e) 1143 (M+) Thermogravimetric analysis Heating weight loss (wt%) Temperature (''C) (Example 3) Synthesis of octabromobis(4-phenoxyphenyl) ether 1Ω round equipped with a cooling condenser with a hydrogen bromide trap and a stirring blade 650 g of bromine and 15.19 g of antimony pentachloride were placed in a bottom flask, heated and stirred.59
A solution prepared by dissolving 90.0 g of bis(4-phenoxyphenyl) ether in 180 ml of chloroform was added dropwise to the solution under reflux under heating at .degree. C. over 3 hours, and then aged at the same temperature for 1 hour. After the reaction is complete, cool to room temperature and add 300ml of water.
1 was added and heated to distill off bromine and chloroform.
冷却後、得られたスラリーを濾過し、水洗を行い、白色
固体249.0gを得た。After cooling, the resulting slurry was filtered and washed with water to obtain 249.0 g of a white solid.
下記の分析結果よりオクタブロモビス(4−フェノキシ
フェニル)エーテルであることを確認した。併せて、本
化合物の熱安定性を熱重量分析(TGA)で測定した結
果も示す。From the analysis results below, it was confirmed that it was octabromobis(4-phenoxyphenyl)ether. In addition, the results of measuring the thermal stability of the present compound by thermogravimetric analysis (TGA) are also shown.
元素分析値
実A11l値(%) 理論値(%)
C−29,4529,25
H−0,951,02
Br−64,5964,86
融点 217〜228℃
質量分析スペクトル
Ma s s (m/ e) 9g5 (M
+)熱重量分析
加熱!Tf量減(重量%) 温度(”C)(実施例4
〜9および比較例1〜2)
実施例1〜3で得られた化合物の難燃剤としての利用例
ポリプロピレン(チッソに7014、耐衝撃グレード)
のペレットに対して、第−表に示した組成となるように
、配合剤を加えた。尚、下記各例における各成分の配合
量単位は、重量部である。Elemental analysis value Actual A11l value (%) Theoretical value (%) C-29,4529,25 H-0,951,02 Br-64,5964,86 Melting point 217-228℃ Mass spectrometry spectrum M s s (m/e ) 9g5 (M
+) Thermogravimetric analysis heating! Tf amount reduction (wt%) Temperature ("C) (Example 4
-9 and Comparative Examples 1-2) Examples of using the compounds obtained in Examples 1-3 as flame retardants Polypropylene (7014 to Chisso, impact resistant grade)
Compounding agents were added to the pellets so that the compositions shown in Table 1 were obtained. In addition, the compounding amount unit of each component in each of the following examples is parts by weight.
配合物を180 ’Cで12分間混練りした。The formulation was mixed for 12 minutes at 180'C.
混練り物を200℃で2分間プレス(100kg/am
2)L、30℃の加圧下(100lc g /cm2)
で5分間冷却し厚さ1及び3mmのシー!・に成型した
。Press the kneaded material at 200℃ for 2 minutes (100kg/am
2) L, under pressure at 30°C (100lc g/cm2)
Cool for 5 minutes and make sheets of 1 and 3 mm thick!・Molded into.
得られたシートの機械特性、難燃性をJISK 675
8及び酸素指数測定(J Is K7201)により
求めた。The mechanical properties and flame retardance of the obtained sheet were determined according to JISK 675.
8 and oxygen index measurement (J Is K7201).
酸素指数法とは、酸素と窒素の調整された混合ガス中で
試料を燃焼させ、ろうそく状の炎をあげて燃える時点で
の限界酸素濃度(%)を測定し、その数値を指数として
表示する方法である。The oxygen index method involves burning a sample in a controlled mixed gas of oxygen and nitrogen, emitting a candle-shaped flame, measuring the critical oxygen concentration (%) at the point of burning, and displaying this value as an index. It's a method.
酸素指数の値が小さいほど燃焼しやすく、値が大きいほ
ど燃えにくいということを示す。The smaller the oxygen index value, the easier it is to burn, and the larger the value, the less flammable it is.
またシートを160℃で100時間媛露し、暴露前後の
色差ΔEより耐熱性を評価した。Further, the sheet was exposed to water at 160° C. for 100 hours, and the heat resistance was evaluated based on the color difference ΔE before and after exposure.
さらにシートを25℃で100日間放置後、難燃剤のブ
ルームの有無を目視により観察した。Further, after the sheet was left at 25° C. for 100 days, the presence or absence of flame retardant bloom was visually observed.
得られた結果を第−表に示す。The results obtained are shown in Table 1.
(実施例10)
実施例1で得られた化合物の難燃剤としての利用例
高耐衝撃性ポリスチレン樹脂(出光スチロールHT50
)100Lrrm部に実施例1で得られた化合物15重
量部と三酸化アンチモン5重量部をミキンングロール2
10℃で練り込み、230℃で加熱プレス(100kg
/cm2)L、厚さ1及び3 rn mのシートに成型
した。(Example 10) Example of use of the compound obtained in Example 1 as a flame retardant High impact resistant polystyrene resin (Idemitsu Styrene HT50
) 15 parts by weight of the compound obtained in Example 1 and 5 parts by weight of antimony trioxide were added to 100 Lrrm parts on a mixing roll 2.
Knead at 10℃, heat press at 230℃ (100kg
/cm2)L and thicknesses of 1 and 3 rn m.
得られたシートの機械特性、難燃性をJISK7113
及び酸素指数alll定<JIS K7201)によ
り求めた。The mechanical properties and flame retardance of the obtained sheet were determined according to JISK7113.
and the oxygen index was determined by all standard (JIS K7201).
またシートを25℃で100日間放置後、難燃剤のブル
ームの有無を目視により観察した。After the sheet was left at 25° C. for 100 days, the presence or absence of flame retardant bloom was visually observed.
得られた結果を第二表に示す。The results obtained are shown in Table 2.
(比較例3.4)
実施例10に阜じて、高耐衝撃性ポリスチレン樹脂に難
燃剤を無添加の場合(比較例3)と汎用具素系難燃剤デ
カブロモジフェニルエーテル(DBDIE)を同量配合
した場合(比較例4)について、i11+1定を行った
。得られた結果を第二表に示す。(Comparative Example 3.4) Based on Example 10, the same amount of the general-purpose elemental flame retardant decabromodiphenyl ether (DBDIE) as in the case where no flame retardant was added to the high-impact polystyrene resin (Comparative Example 3) For the case of blending (Comparative Example 4), i11+1 constant was conducted. The results obtained are shown in Table 2.
第二表
以上実施例で示した様に、耐熱性、耐マイグレション性
に優れた難燃剤が得られたことがわかった。As shown in Table 2 and in the Examples, it was found that a flame retardant with excellent heat resistance and migration resistance was obtained.
第1図〜3図は、それぞれ実施例1〜3の化合物の赤外
吸収スペクトルチャートである。1 to 3 are infrared absorption spectrum charts of the compounds of Examples 1 to 3, respectively.
Claims (2)
〜5の数、b、cは1〜4の数)で表されるハロゲン化
ビス(4−フェノキシフェニル)エーテル。(1) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼[I] (In the formula [I], X represents a halogen atom, and a and d are 1
5, b and c are numbers 1 to 4).
ン化ビス(4−フェノキシフェニル)エーテルを配合す
ることを特徴とする難燃性高分子組成物。(2) A flame-retardant polymer composition characterized by blending a halogenated bis(4-phenoxyphenyl) ether represented by the general formula [I] into a polymer.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP28142588A JP2636380B2 (en) | 1988-11-09 | 1988-11-09 | Halogenated bis (4-phenoxyphenyl) ether and flame-retardant high molecular composition containing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP28142588A JP2636380B2 (en) | 1988-11-09 | 1988-11-09 | Halogenated bis (4-phenoxyphenyl) ether and flame-retardant high molecular composition containing the same |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH02129137A true JPH02129137A (en) | 1990-05-17 |
JP2636380B2 JP2636380B2 (en) | 1997-07-30 |
Family
ID=17638984
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP28142588A Expired - Lifetime JP2636380B2 (en) | 1988-11-09 | 1988-11-09 | Halogenated bis (4-phenoxyphenyl) ether and flame-retardant high molecular composition containing the same |
Country Status (1)
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JP2012512939A (en) * | 2008-12-19 | 2012-06-07 | ケムチュア コーポレイション | Flame retardant halogenated phenyl ether blend |
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WO2011090631A1 (en) | 2010-01-25 | 2011-07-28 | Chemtura Corporation | Flame retardant halogenated phenyl ethers |
US8362127B2 (en) | 2010-01-25 | 2013-01-29 | Chemtura Corporation | Flame retardant halogenated phenyl ethers |
WO2013048642A1 (en) | 2011-09-29 | 2013-04-04 | Chemtura Corporation | Flame retardant halogenated phenyl ethers |
WO2013048399A1 (en) | 2011-09-29 | 2013-04-04 | Chemtura Corporation | Flame retardant halogenated phenyl ethers |
JP2014534284A (en) * | 2011-09-29 | 2014-12-18 | ケムチュア コーポレイション | Flame retardant halogenated phenyl ether |
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