JPH04288328A - New brominated polyether compound - Google Patents
New brominated polyether compoundInfo
- Publication number
- JPH04288328A JPH04288328A JP5248391A JP5248391A JPH04288328A JP H04288328 A JPH04288328 A JP H04288328A JP 5248391 A JP5248391 A JP 5248391A JP 5248391 A JP5248391 A JP 5248391A JP H04288328 A JPH04288328 A JP H04288328A
- Authority
- JP
- Japan
- Prior art keywords
- polyether compound
- formula
- bromine content
- brominated polyether
- compound
- 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
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 14
- 229920000570 polyether Polymers 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 title claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 24
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 16
- 239000002904 solvent Substances 0.000 abstract description 12
- 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 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 2
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 238000006068 polycondensation reaction Methods 0.000 abstract 1
- 239000003063 flame retardant Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 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 description 2
- 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 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical class C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyethers (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、臭素含有率の高い新規
な臭素含有ポリエーテル化合物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel bromine-containing polyether compound having a high bromine content.
【０００２】0002
【従来の技術】従来、高臭素含有化合物は、プラスチッ
ク、繊維、ゴム、塗料などに難燃剤として広く用いられ
ている。このような化合物の例としては、式（ＩＩ）BACKGROUND OF THE INVENTION Hitherto, high bromine-containing compounds have been widely used as flame retardants for plastics, fibers, rubber, paints, and the like. Examples of such compounds include formula (II)
【
化２】
で示されるデカブロモジフェニルエーテル、式（ＩＩＩ
）[
Decabromodiphenyl ether represented by formula (III)
)
【化３】 で示されるテトラブロモビスフェールＡ、式（ＩＶ）[Chemical formula 3] Tetrabromobisphenol A represented by formula (IV)
【
化４】
で示される臭素化エポキシ樹脂などを挙げることができ
る。このような難燃剤は臭素含有量が高いものほど難燃
性に優れると考えられる。[
Examples include brominated epoxy resins represented by the following formula. It is believed that the higher the bromine content of such flame retardants, the better the flame retardancy.
【０００３】しかしながら、式（ＩＩ）のデカブロモジ
フェニルエーテルは、特に臭素含有量が高く、理論臭素
含有量が８３．３質量％であり、少量の添加でも高い難
燃効果を示すが、各種溶剤に対する溶解性に乏しく、使
い難いという欠点がある。However, decabromodiphenyl ether of formula (II) has a particularly high bromine content, with a theoretical bromine content of 83.3% by mass, and exhibits a high flame retardant effect even when added in a small amount. The drawback is that it has poor solubility and is difficult to use.
【０００４】また、式（ＩＩＩ）のテトラブロモビスフ
ェールＡは、各種溶剤に対する溶解性はある程度あるも
のの、理論臭素含有量が５８．４質量％と、臭素含有量
が低く、デカブロモジフェニルエーテルに比べて難燃性
に劣るという欠点がある。[0004]Although tetrabromobisphenol A of formula (III) has a certain degree of solubility in various solvents, it has a low theoretical bromine content of 58.4% by mass, and has a low bromine content compared to decabromodiphenyl ether. The disadvantage is that it has poor flame retardancy.
【０００５】さらに、式（ＩＶ）の臭素化エポキシ樹脂
は、同様に各種溶剤に対する溶解性はある程度あるもの
の、理論臭素含有量が６０．６質量％で（但し、ｎ＝１
のとき、ｎ＝２以上ではこの値よりも低くなる。）、臭
素含有量が低く、デカブロモジフェニルエーテルに比べ
て難燃性に劣るという欠点がある。Furthermore, although the brominated epoxy resin of formula (IV) similarly has a certain degree of solubility in various solvents, its theoretical bromine content is 60.6% by mass (however, n=1
When n=2 or more, the value becomes lower than this value. ), it has the disadvantage of having a low bromine content and inferior flame retardancy compared to decabromodiphenyl ether.
【０００６】[0006]
【発明が解決しようとする課題】本発明は、これら従来
技術の欠点を解消し、各種溶剤に対する溶解性に優れ、
臭素含有量の高い新規な臭素含有ポリエーテル化合物を
提供するものである。[Problems to be Solved by the Invention] The present invention solves the drawbacks of these conventional techniques, and has excellent solubility in various solvents.
The present invention provides a novel bromine-containing polyether compound with a high bromine content.
【０００７】[0007]
【課題を解決するための手段】本発明は、一般式（Ｉ）
[Means for Solving the Problems] The present invention provides general formula (I)
【化５】
〔式中、ｎは１以上の整数を示す。〕で表される繰り返
し単位を有する新規な臭素含有ポリエーテル化合物に関
する。embedded image [where n represents an integer of 1 or more]. This invention relates to a novel bromine-containing polyether compound having a repeating unit represented by the following formula.
【０００８】本発明の新規な臭素含有ポリエーテル化合
物は、デカブロモジフェニルエーテルとエチレングリコ
ールに類似の構造を有している。従って、該ポリエーテ
ル化合物は、デカブロモジフェニルエーテルの高臭素含
有量の特徴とエチレングリコールの各種溶剤に対する溶
解性に優れる特徴を併せ持つように設計されている。な
お、該ポリエーテル化合物の理論臭素含有量は７４．４
質量％となり、デカブロモジフェニルエーテルのそれ（
８３．３質量％）よりは低いが、テトラブロモビスフェ
ールＡ（５８．８質量％）、臭素化エポキシ樹脂（６０
．６質量％）よりも高い。The novel bromine-containing polyether compounds of the present invention have structures similar to decabromodiphenyl ether and ethylene glycol. Therefore, the polyether compound is designed to have both the high bromine content of decabromodiphenyl ether and the excellent solubility in various solvents of ethylene glycol. The theoretical bromine content of the polyether compound is 74.4.
% by mass, and that of decabromodiphenyl ether (
Tetrabromobisphal A (58.8% by mass), brominated epoxy resin (60% by mass), but lower than 83.3% by mass).
．． 6% by mass).
【０００９】本発明の新規な臭素含有ポリエーテル化合
物は、公知の任意の方法によって合成することができる
。例えば、該ポリエーテル化合物は、適当な溶媒中でデ
カブロモジフェニルエーテルとエチレングリコールを等
モル量配合し、アルカリ性触媒の存在下にＨＢｒ を脱
離させながら縮合重合させて合成することができる。The novel bromine-containing polyether compound of the present invention can be synthesized by any known method. For example, the polyether compound can be synthesized by blending equimolar amounts of decabromodiphenyl ether and ethylene glycol in a suitable solvent and conducting condensation polymerization in the presence of an alkaline catalyst while eliminating HBr.
【００１０】上記一般式（Ｉ）において、ｎは１以上の
整数を示すが、ｎは１〜５であることが好ましい。ｎ＝
５を超えると、溶剤に対する溶解性に劣るようになる。In the above general formula (I), n represents an integer of 1 or more, but preferably 1-5. n=
When it exceeds 5, the solubility in solvents becomes poor.
【００１１】本発明の新規な臭素含有ポリエーテル化合
物は、臭素含有量の高いことから、特に難燃剤として有
用である。The novel bromine-containing polyether compounds of the present invention are particularly useful as flame retardants because of their high bromine content.
【００１２】0012
【実施例】次に、本発明を実施例によって具体的に説明
するが、本発明はこれに限定されるものではない。[Examples] Next, the present invention will be explained in detail with reference to Examples, but the present invention is not limited thereto.
【００１３】実施例１
デカブロモジフェニルエーテル５７．６ｇ（６０．０ミ
リモル）とエチレングリコール３．７２ｇ（５９．９ミ
リモル）を、炭酸カリウム２５．３ｇ（２５８ミリモル
）及び１８−クラウン６−エーテル４．２８ｇ（１６．
２ミリモル）を含有するジメチルアセトアミド２７０ｃ
ｍ３ 中に仕込み、８０℃で２４時間反応させた。反応
混合物を大量の水中に注ぎ、析出した固体を水で洗浄後
、減圧下１００℃で乾燥し、目的とする化合物を得た。
収量は４４％であった。Example 1 57.6 g (60.0 mmol) of decabromodiphenyl ether and 3.72 g (59.9 mmol) of ethylene glycol were mixed with 25.3 g (258 mmol) of potassium carbonate and 4.5 g (258 mmol) of 18-crown 6-ether. 28g (16.
dimethylacetamide 270c containing 2 mmol)
m3 and reacted at 80°C for 24 hours. The reaction mixture was poured into a large amount of water, and the precipitated solid was washed with water and dried at 100° C. under reduced pressure to obtain the target compound. Yield was 44%.
【００１４】得られた化合物の融点（ＤＳＣ法）は９０
℃、臭素含有量は７４．１質量％（理論値７４．４質量
％）であった。該化合物の １Ｈ−ＮＭＲを重水素化ピ
リジンを溶媒として測定したところ、エチレングリコー
ル残基のエチレン基水素原子のプロトンに帰属されるシ
ャープな吸収が３．５ｐｐｍ 付近に見られた。該化合
物の重量平均分子量は、ＧＰＣ法により、テトラヒドロ
フラン溶媒を用い、標準単分散スチレン換算で測定した
ところ、１０００であった。なお、該化合物のテトラヒ
ドロフランに一部不溶のため濾過して測定した。該化合
物の各種溶剤に対する溶解性を調べ、表１に結果をまと
めた。The melting point (DSC method) of the obtained compound was 90
℃, the bromine content was 74.1% by mass (theoretical value 74.4% by mass). When 1H-NMR of the compound was measured using deuterated pyridine as a solvent, a sharp absorption attributed to the proton of the ethylene group hydrogen atom of the ethylene glycol residue was observed at around 3.5 ppm. The weight average molecular weight of the compound was determined to be 1000 by GPC using a tetrahydrofuran solvent in terms of standard monodisperse styrene. Note that since some of the compound is insoluble in tetrahydrofuran, the measurement was performed after filtration. The solubility of the compound in various solvents was investigated, and the results are summarized in Table 1.
【００１５】なお、溶解性は、溶剤１デシリットルに上
記化合物２．５ｇを溶解し、結果を下記の基準で評価し
た。
○ 完全に溶解した。
△ ほぼ溶解したが、一部は不溶であった。
× 不溶であった。The solubility was evaluated by dissolving 2.5 g of the above compound in 1 deciliter of solvent and evaluating the results according to the following criteria. ○ Completely dissolved. △Almost dissolved, but some remained insoluble. × It was insoluble.
【００１６】[0016]
【表１】[Table 1]
【００１７】[0017]
【発明の効果】本発明の臭素含有ポリエーテル化合物は
、臭素含有量が高く、しかも各種溶剤に対する溶解性も
相当に高いので、難燃剤として著しく有用である。EFFECTS OF THE INVENTION The bromine-containing polyether compound of the present invention has a high bromine content and also has considerably high solubility in various solvents, so it is extremely useful as a flame retardant.
Claims (1)
し単位を有する新規な臭素含有ポリエーテル化合物。Claims 1: General formula (I) [In the formula, n represents an integer of 1 or more]. ] A novel bromine-containing polyether compound having a repeating unit represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5248391A JPH04288328A (en) | 1991-03-18 | 1991-03-18 | New brominated polyether compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5248391A JPH04288328A (en) | 1991-03-18 | 1991-03-18 | New brominated polyether compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04288328A true JPH04288328A (en) | 1992-10-13 |
Family
ID=12915964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5248391A Pending JPH04288328A (en) | 1991-03-18 | 1991-03-18 | New brominated polyether compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04288328A (en) |
-
1991
- 1991-03-18 JP JP5248391A patent/JPH04288328A/en active Pending
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