JPH01236241A - Production of curable phosphazene compound - Google Patents
Production of curable phosphazene compoundInfo
- Publication number
- JPH01236241A JPH01236241A JP63060586A JP6058688A JPH01236241A JP H01236241 A JPH01236241 A JP H01236241A JP 63060586 A JP63060586 A JP 63060586A JP 6058688 A JP6058688 A JP 6058688A JP H01236241 A JPH01236241 A JP H01236241A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- phosphazene compound
- curable
- chlorine
- 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
- -1 phosphazene compound Chemical class 0.000 title claims abstract description 63
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 229910052751 metal Inorganic materials 0.000 claims abstract description 10
- 239000002184 metal Substances 0.000 claims abstract description 10
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 7
- 150000001923 cyclic compounds Chemical class 0.000 abstract description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 abstract description 3
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 abstract description 2
- 230000009257 reactivity Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011345 viscous material Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005277 alkyl imino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- NWJKPSLXLQLUTC-UHFFFAOYSA-N ethane-1,2-diol;sodium Chemical compound [Na].OCCO NWJKPSLXLQLUTC-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SHDZTIZBSYDZSH-UHFFFAOYSA-N 2-methylprop-2-enoyl bromide Chemical compound CC(=C)C(Br)=O SHDZTIZBSYDZSH-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical class OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 239000005548 dental material Substances 0.000 description 1
- 239000004851 dental resin Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N o-hydroxybenzyl alcohol Chemical class OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [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])O* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical class OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は硬化性ホスファゼン化合物の製造方法に関し、
詳しくは実質的に塩素原子を含有しない硬化性ホスファ
ゼン化合物を高い反応性で効率よく製造する方法に関す
る。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a method for producing a curable phosphazene compound,
More specifically, the present invention relates to a method for efficiently producing a curable phosphazene compound containing substantially no chlorine atoms with high reactivity.
〔従来の技術及び発明が解決しようとする課題〕−ａに
、硬化性ホスファゼン化合物は、熱や活性エネルギー線
によって硬化して、耐熱性や圧縮強度、硬度等の機械的
性質にすぐれると共に、金属やセラミックス等に対する
接着性にすぐれた硬化物を与えるため、電子部品製造用
のホトレジスト、各種成形品の保護被覆材、歯科用レジ
ンセメント及び充填材などの用途が期待されている。[Prior art and problems to be solved by the invention]-a. Curable phosphazene compounds can be cured by heat or active energy rays, and have excellent mechanical properties such as heat resistance, compressive strength, and hardness. Because it provides a cured product with excellent adhesion to metals, ceramics, etc., it is expected to be used in photoresists for manufacturing electronic parts, protective coatings for various molded products, dental resin cements, and filling materials.
これまでのところ、このような硬化性ホスファゼン化合
物の製造方法としては、塩素化ホスファゼン化合物にエ
チレン性不飽和結合を有する不飽和ヒドロキシ化合物を
脱塩化水素剤の存在下で反応させる方法が知られている
（特公昭５９−２４４９号公報、特開昭６１−４７４０
６号公報）。So far, as a method for producing such a curable phosphazene compound, a method is known in which a chlorinated phosphazene compound is reacted with an unsaturated hydroxy compound having an ethylenically unsaturated bond in the presence of a dehydrochlorination agent. (Japanese Patent Publication No. 59-2449, Japanese Patent Publication No. 61-4740)
Publication No. 6).
しかしながら、この方法では、塩素化ホスファゼン化合
物の塩素原子と不飽和ヒドロキシ化合物のヒドロキシル
基との間の縮合反応の速度が遅く、反応を完結させるた
めには長時間を要するという欠点がある。また、例えば
歯科用材料や電子部品材料として使用する場合には、原
料である塩素化ホスファゼン化合物中のすべての塩素原
子が置換され、得られる硬化性ホスファゼン化合物中に
は実質的に全く塩素原子が存在しないことが好ましいが
、上記の如き従来の方法では、このようにするには数十
乃至数百時間を要し、これを実現することは工業上はと
んど不可能であった。However, this method has the disadvantage that the rate of condensation reaction between the chlorine atom of the chlorinated phosphazene compound and the hydroxyl group of the unsaturated hydroxy compound is slow and it takes a long time to complete the reaction. In addition, for example, when used as a dental material or electronic component material, all chlorine atoms in the raw material chlorinated phosphazene compound are replaced, and the resulting curable phosphazene compound contains virtually no chlorine atoms. Although it is preferable that there be no such presence, in the conventional method as described above, it takes tens to hundreds of hours to achieve this, and it is almost impossible to achieve this in an industrial manner.
そこで本発明者らは、上記従来技術の欠点を解消し、実
質的に塩素原子を含有しない硬化性ホスファゼン化合物
を、短時間で効率よく製造すべく鋭意研究を重ねた。Therefore, the present inventors have conducted extensive research in order to eliminate the drawbacks of the above-mentioned conventional techniques and to efficiently produce a curable phosphazene compound that does not contain substantially chlorine atoms in a short period of time.
その結果、原料である塩素含有ホスファゼン化合物を多
価アルコールのモノアルカリ金属塩と反応させた後に、
アクリロイル基あるいはメタクリロイル基含有化合物を
反応させることによって、目的を達成できることを見出
した。本発明はかがる知見に基いて完成したものである
。As a result, after reacting the raw material chlorine-containing phosphazene compound with the monoalkali metal salt of polyhydric alcohol,
It has been found that the object can be achieved by reacting a compound containing an acryloyl group or a methacryloyl group. The present invention was completed based on this knowledge.
すなわち本発明は、塩素含有ホスファゼン化合物に重合
硬化性基を導入するにあたり、塩素含有ホスファゼン化
合物を多価アルコールのモノアルカリ金属塩と反応させ
て水酸基を有するホスファゼン化合物を得、しかる後に
アクリロイル基あるいはメタクリロイル基含有化合物と
反応させることを特徴とする硬化性ホスファゼン化合物
の製造方法を提供するものである。That is, in the present invention, when introducing a polymerizable curable group into a chlorine-containing phosphazene compound, the chlorine-containing phosphazene compound is reacted with a monoalkali metal salt of a polyhydric alcohol to obtain a phosphazene compound having a hydroxyl group, and then an acryloyl group or a methacryloyl group is introduced. The present invention provides a method for producing a curable phosphazene compound, which is characterized by reacting it with a group-containing compound.
本発明の方法において、原料化合物として用いる塩素含
をホスファゼン化合物は、種々のものがあるが通常は、
式（ＮＰＣｆ□）１で表わされる環状あるいは式（１４
Ｐ、（ＮＰＣＬ）、、、ＮＰ（１！３で表わされる鎖状
のジクロロホスファゼン多量体（ここで、ｎは３以上、
好ましくは３〜１８である。）が好適である。In the method of the present invention, there are various types of chlorine-containing phosphazene compounds used as raw material compounds, but usually,
Cyclic shape represented by the formula (NPCf□)1 or the formula (14
P, (NPCL), , NP (1! Chain-like dichlorophosphazene polymer represented by 3 (where n is 3 or more,
Preferably it is 3-18. ) is preferred.
また、−数式（Ｎ Ｐ （Ｃｆ）、（Ｂ）、）（式中、
ｐ、ｑはｐ＞Ｏ，ｑ＞Ｑであり、かつｐ＋ｑ＝２を満た
す実数を示し、Ｂは非重合硬化性基を示す。）で表わさ
れる繰返し単位を有し、重合度が３以上、好ましくは３
〜１８の塩素含有環状あるいは鎖状ホスファゼン化合物
を原料化合物として用いることもできる。これは、前述
のジクロロホスファゼン多量体に、上記非重合硬化性Ｉ
Ｂを有する化合物を反応させることによって得ることが
できる。ここで、非重合硬化性基Ｂとしては、−数式
ＲＩＱ−・・・（１）
あるいは
で表わされる基を示す。ここで、式（１）中Ｑは酸素原
子、硫黄原子又はイミノ基を示し、Ｒ１は炭素数１−１
８のアルキル基あるいは炭素数１〜１８のハロゲン化ア
ルキル基を示す。具体的には、メトキシ基、エトキシ基
、プロポキシ基、ブトキシ基、ペンチルオキシ基、ヘキ
シルオキシ基、ヘプチルオキシ基、オクチルオキシ基な
どのアルコキシ基、ハロゲン（例えばフッ素、塩素、臭
素など）で置換された同様のアルコキシ基、メチルチオ
基、エチルチオ基、プロピル千オ基、ブチルチオ基、ペ
ンチルチオ基、ヘプチルチオ基、オクチルチオ基などの
アルキルチオ基、ハロゲン（例えばフッ素、塩素、臭素
など）で置換された同様のアルキルチオ基、メチルイミ
ノ基、エチルイミノ基、プロピルイミノ基、ブチルイミ
ノ基、ペンチルイミノ基、ヘキシルイミノ基、ヘプチル
イミノ基、オクチルイミノ基などのアルキルイミノ基。In addition, - the formula (N P (Cf), (B), ) (in the formula,
p and q represent real numbers satisfying p>O, q>Q and p+q=2, and B represents a non-polymerizable curable group. ), and the degree of polymerization is 3 or more, preferably 3.
~18 chlorine-containing cyclic or chain phosphazene compounds can also be used as raw material compounds. This adds the above-mentioned non-polymerizable curable I to the above-mentioned dichlorophosphazene multimer.
It can be obtained by reacting a compound having B. Here, as the non-polymerizable curable group B, - formula
RIQ-...(1) or a group represented by. Here, Q in formula (1) represents an oxygen atom, a sulfur atom, or an imino group, and R1 has 1-1 carbon atoms.
8 alkyl group or a halogenated alkyl group having 1 to 18 carbon atoms. Specifically, alkoxy groups such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, and octyloxy group, and substituted with halogen (e.g., fluorine, chlorine, bromine, etc.) Similar alkoxy groups, alkylthio groups such as methylthio, ethylthio, propylthio, butylthio, pentylthio, heptylthio, octylthio, similar alkylthio substituted with halogen (e.g. fluorine, chlorine, bromine, etc.) group, alkylimino groups such as methylimino group, ethylimino group, propylimino group, butylimino group, pentylimino group, hexylimino group, heptylimino group, octylimino group.
ハロゲン（例えばフッ素、塩素、臭素など）で置換され
た同様のアルキルイミノ基等をあげることができる。ま
た、弐（ＩＩ）中Ｑは前記と同じであり、Ｒ２−Ｒ６は
それぞれ独立に水素原子、ハロゲン原子、炭素数１〜４
のアルキル基又は炭素数１〜４のハロゲン化アルキル基
を示す。式（ＩＴ）の基は、具体的には、フェノキシ基
、チオフェニル基、ハロゲン化フェノキシ基（２，４，
６−ＭＪジブロモェノキシ基、４−ブロモフェノキシ基
、２−クロロフェノキシＬ ２．４−ジクロロフェノ
キシ基など）およびハロゲン化チオフェニル基（４−ク
ロロフェニルチオ基など）、あるいはアニリンおよびハ
ロゲン化アニリン（２−クロロアニリン、２．４−ジク
ロロアニリン、２．４，６−ドリプロモアニリンなど）
のアミノ基より水素原子を取り除いた残基などをあげる
ことができる。Similar alkylimino groups substituted with halogen (eg, fluorine, chlorine, bromine, etc.) can be mentioned. Further, Q in II (II) is the same as above, and R2 to R6 are each independently a hydrogen atom, a halogen atom, or a carbon number of 1 to 4.
represents an alkyl group or a halogenated alkyl group having 1 to 4 carbon atoms. Specifically, the group of formula (IT) includes a phenoxy group, a thiophenyl group, and a halogenated phenoxy group (2,4,
6-MJ dibromoenoxy group, 4-bromophenoxy group, 2-chlorophenoxy L 2.4-dichlorophenoxy group, etc.) and halogenated thiophenyl group (4-chlorophenylthio group, etc.), or aniline and halogenated aniline (2-chlorophenoxy group, etc.) Aniline, 2,4-dichloroaniline, 2,4,6-dolipromoaniline, etc.)
Examples include residues obtained by removing a hydrogen atom from an amino group.
本発明の方法では、上記のような塩素含有ホスファゼン
化合物を原料として、これに多価アルコールのモノアル
カリ金属塩を反応させる。ここで多価アルコールのモノ
アルカリ金属塩は、−数式 ＭＯ−Ｒ’−（ＯＨ）ｋ
・・・ （１）（式中、ｋは１以上の整数、好ま
しくは１又は２を示し、Ｒ７は多価アルコールから水酸
基を除いた残基を示し、Ｍはアルカリ金属を示す。）で
表わされる。このうちジオール、トリオールなどのモノ
ナトリウム塩、モノカリウム塩等が好ましく、具体的に
はエチレングリコール、プロピレングリコール、ブチレ
ングリコール、ジエチレングリコール、グリセロール、
ハイドロキノン、ヒドロキシベンジルアルコール、フェ
ニルエチルグリコール、キシリレングリコールなどのモ
ノナトリウム塩あるいはカリウム塩等をあげることがで
きる。In the method of the present invention, a chlorine-containing phosphazene compound as described above is used as a raw material and is reacted with a monoalkali metal salt of a polyhydric alcohol. Here, the monoalkali metal salt of polyhydric alcohol has the formula: MO-R'-(OH)k
... (1) (wherein k represents an integer of 1 or more, preferably 1 or 2, R7 represents a residue obtained by removing a hydroxyl group from a polyhydric alcohol, and M represents an alkali metal) It will be done. Among these, monosodium salts, monopotassium salts, etc. of diols and triols are preferable, and specifically, ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, glycerol,
Examples include monosodium salts or potassium salts of hydroquinone, hydroxybenzyl alcohol, phenylethyl glycol, xylylene glycol, and the like.
本発明の方法にしたがって、上述した塩素含有ホスファ
ゼン化合物と多価アルコールのモノアルカリ金属塩を反
応させると、水酸基を有するホスファゼン化合物が得ら
れる。ここで塩素含有ホスファゼン化合物としてジクロ
ロホスファゼン多量体ヲ用い場合には、多価アルコール
のモノアルカリ金属塩と反応後に、必要に応じて前述し
た非重合硬化性ＩＢを有する化合物と反応させると、適
度に非重合硬化性基Ｂの導入された水酸基含有ホスファ
ゼン化合物となる。なお、塩素含有ホスファゼン化合物
として一般式（Ｎ Ｐ （Ｃｆｆ１）、（Ｂ）、）で表
わされる繰返し単位を持つ化合物を用いたときは、多価
アルコールのモノアルカリ金属塩と反応後に、非重合硬
化性基Ｂを導入する必要がないことは勿論である。According to the method of the present invention, when the above-described chlorine-containing phosphazene compound and a monoalkali metal salt of a polyhydric alcohol are reacted, a phosphazene compound having a hydroxyl group is obtained. When a dichlorophosphazene polymer is used as the chlorine-containing phosphazene compound, if necessary, after reacting with a monoalkali metal salt of a polyhydric alcohol, it can be reacted with the above-mentioned compound having non-polymerizable curable IB. This results in a hydroxyl group-containing phosphazene compound into which a non-polymerizable curable group B is introduced. Note that when a compound having a repeating unit represented by the general formula (N P (Cff1), (B), Of course, it is not necessary to introduce the functional group B.
本発明の方法では、塩素含有ホスファゼン化合物と多価
アルコールのモノアルカリ金属塩との反応によって、例
えば、
一般式 （ＮＰ（ＯＲ’（ＯＨ）ｋ）、（Ｂ）ｂ ）（
式中、Ｂ、Ｒ々、には前記と同じであり、ａ、 ｂは
ａ＞０．ｂ≧０であってａ＋ｂ＝２を満たす実数である
。）で表わされる繰返し単位を有する水酸基含有ホスフ
ァゼン化合物（重合度３以上）が得られることとなる。In the method of the present invention, for example, the general formula (NP(OR'(OH)k), (B)b)(
In the formula, B and R are the same as above, and a and b are a>0. It is a real number that satisfies b≧0 and a+b=2. ) A hydroxyl group-containing phosphazene compound (degree of polymerization of 3 or more) having a repeating unit represented by the following formula is obtained.
さらに、本発明の方法では上記の如き水酸基含有ホスフ
ァゼン化合物を、アクリロイル基あるいはメタクリロイ
ル基含有化合物と反応させる。ここで用いるアクリロイ
ル基あるいはメタク、リロイル基含有化合物は、各種の
ものがあり、状況に応して適宜選定すればよいが、通常
はアクリロイル基含有化合物としては、アクリル酸、ア
クリル酸クロリド、アクリル酸プロミドなどが好適であ
り、またメタクリロイル基含有化合物としては、メタク
リル酸、メタクリル酸クロリド、メタクリル酸プロミド
などが好適である。Further, in the method of the present invention, a hydroxyl group-containing phosphazene compound as described above is reacted with an acryloyl group- or methacryloyl group-containing compound. There are various types of acryloyl group-containing compounds, methacrylic acid chloride, and lyloyl group-containing compounds used here, and they can be selected appropriately depending on the situation, but acryloyl group-containing compounds are usually acrylic acid, acrylic acid chloride, acrylic acid chloride, Preferred examples include bromide, and preferred examples of the methacryloyl group-containing compound include methacrylic acid, methacrylic acid chloride, and methacrylic acid bromide.
この水酸基含有ホスファゼン化合物とアクリロイル基あ
るいはメタクリロイル基含有化合物との反応は、必要に
応じて溶媒を用い、また適当な酸あるいは塩基触媒の存
在下で行えば効率よく進行する。この反応によって、目
的とする硬化性ホスファゼン化合物が得られるが、この
硬化性ホスファゼン化合物は、例えば、
一般式
％式％））
あるいは −数式
［ＮＰＣＯＲ’（ＱＣＣ＝ＣＨｚ）ｋ）−（Ｂ）ｂ：ｆ
ｆ１ １
ＣＨ３
（式中、Ｒ’＋ ｋ、ａおよびｂは前記と同じ。）で
表わされる繰返し単位を有する硬化性ホスファゼン化合
物（重合度３以上）である。The reaction between the hydroxyl group-containing phosphazene compound and the acryloyl group- or methacryloyl group-containing compound will proceed efficiently if necessary using a solvent and in the presence of a suitable acid or base catalyst. Through this reaction, the desired curable phosphazene compound is obtained, and this curable phosphazene compound has the following formula: :f
It is a curable phosphazene compound (polymerization degree of 3 or more) having a repeating unit represented by f1 1 CH3 (in the formula, R'+ k, a and b are the same as above).
この弐において、非重合硬化性基Ｂは、上記硬化性ホス
ファゼン化合物の硬化性の程度を調節するために導入す
るものであり、必ずしも必要ではなく、例えばｂ＝０（
即ちａ＝２）、に＝１とすれば、上記式は −数式
（ＮＰＣＯＲ’０Ｃ−ＣＨ＝ＣＨりり
八
あるいは −数式
％式％）
次に、本発明を実施例に基いてさらに詳しく説明する。In this second, the non-polymerizable curable group B is introduced to adjust the degree of curability of the curable phosphazene compound, and is not necessarily necessary, for example, when b=0 (
That is, if a = 2), then = 1, then the above formula is: .
実施例１
２１容の反応槽に、エタノール５２０ｄとエチレングリ
コールモノナトリウム塩１０１．０ｇを入れ、撹拌して
溶解させた。次いで、これにヘキサクロロンクロトリホ
スファゼン〔式（ＮＦにｇｚｈで表わされる環状化合物
〕７０ｇをトルエン３６０雁に溶解させた溶液を滴下し
た。その後、反応系が中性になるまで還流下で反応を行
った。冷却後、生成した塩化ナトリウムを濾別し、濾液
より溶媒を減圧下で除去し、透明な粘稠体であるヘキサ
ヒドロキシエトキシシクロトリホスファゼンを収率９７
％で得た。Example 1 520 d of ethanol and 101.0 g of ethylene glycol monosodium salt were placed in a 21-volume reaction tank and dissolved by stirring. Next, a solution of 70 g of hexachlorone crotriphosphazene [a cyclic compound represented by the formula (NF and gzh)] dissolved in 360 g of toluene was added dropwise.Then, the reaction was carried out under reflux until the reaction system became neutral. After cooling, the produced sodium chloride was filtered off, and the solvent was removed from the filtrate under reduced pressure to obtain hexahydroxyethoxycyclotriphosphazene, a transparent viscous substance, with a yield of 97%.
Obtained in %.
続いて、上記へキサヒドロキシエトキシシクロトリホス
ファゼン８３．６ｇを２１容の反応槽に入れ、これにジ
エチルエーテル４００燻およびＮ。Subsequently, 83.6 g of the above hexahydroxyethoxycyclotriphosphazene was placed in a 21-volume reaction tank, and 400 g of diethyl ether and N were added thereto.
Ｎ−ジメチルアニリン１３３．３ｇを加えて攪拌を行っ
た。さらに、これに塩化メタクリロイル（メタクリル酸
クロリド）１１６ｇを滴下し、還流下で２時間反応を行
った。反応終了後、濾過により生成した固形物を除去し
、エーテル層を水洗した。133.3 g of N-dimethylaniline was added and stirred. Furthermore, 116 g of methacryloyl chloride (methacrylic acid chloride) was added dropwise thereto, and the reaction was carried out under reflux for 2 hours. After the reaction was completed, the solid matter produced was removed by filtration, and the ether layer was washed with water.
次いでエーテルを減圧留去することにより、目的とする
透明な粘稠体である硬化性ホスファゼン化合物１２９ｇ
を得た。このもののは下記の構造式％式％））
］
・で表わされる環状化合物であった。Then, by distilling off the ether under reduced pressure, 129 g of the desired curable phosphazene compound, which is a transparent viscous substance, is obtained.
I got it. This compound was a cyclic compound represented by the following structural formula %) ) ] .
なお、このものの赤外線吸収スペクトルでは、Ｐ Ｏ
ＣＨｚ、Ｃ＝Ｃ，Ｃ＝０．Ｐ＝Ｎ、Ｐ Ｎに起因する
吸収が認められたが、−ＯＨに基づく吸収は全くないこ
とから、ヘキサヒドロエトキシシクロトリホスファゼン
とメタクリル酸クロリドとの反応は１００％進行してい
ることがわかる。In addition, in the infrared absorption spectrum of this product, P O
CHz, C=C, C=0. Absorption due to P=N and P N was observed, but there was no absorption due to -OH, indicating that the reaction between hexahydroethoxycyclotriphosphazene and methacrylic acid chloride progressed 100%. .
また、上記硬化性ホスファゼン化合物のバイルシュタイ
ンテストは陰性であり、このことからこの硬化性ホスフ
ァゼン化合物には塩素は全く残存していないことが確認
された。Furthermore, the Beilstein test of the above-mentioned curable phosphazene compound was negative, which confirmed that no chlorine remained in this curable phosphazene compound.
実施例２
５１容の反応槽に、テトラヒドロフラン１０００ｍ！と
金属ナトリウム２８．８ｇを投入し、これに２゜２．２
−トリフルオロエタノール１２５．１ｇを滴下し、金属
ナトリウムが消失するまで反応させた。Example 2 1000 m of tetrahydrofuran in a 51 volume reaction tank! and 28.8g of metallic sodium were added, and the temperature was 2°2.2
- 125.1 g of trifluoroethanol was added dropwise, and the reaction was allowed to proceed until metallic sodium disappeared.
別途、ヘキサクロロシクロトリホスファゼン２９０ｇを
テトラヒドロフラン７００−に溶解させ、これを前記反
応槽内に滴下し、還流下で２時間反応を行った。さらに
、エチレングリコールモノナトリウム塩３１６ｇを投入
し、１０時間還流を行った。Separately, 290 g of hexachlorocyclotriphosphazene was dissolved in 700 g of tetrahydrofuran, and this was added dropwise into the reaction tank, and the reaction was carried out under reflux for 2 hours. Furthermore, 316 g of ethylene glycol monosodium salt was added and refluxed for 10 hours.
濾過後、テトラヒドロフランを減圧留去し、透明な粘稠
体４４２ｇを得た。After filtration, tetrahydrofuran was distilled off under reduced pressure to obtain 442 g of a transparent viscous substance.
次いで、この粘稠体２７９．１ｇ、メタクリル酸２１５
ｇ及びベンゼン１０００ ｍｌをフラスコに仕込み、硫
酸３ｇを加えて、５０°Ｃで１２時間反応を行った。反
応後、中和、水洗し、さらにベンゼンを留去して、目的
とする透明粘稠体である硬化性ホスファゼン化合物３４
２ｇを得た。Next, 279.1 g of this viscous material, 215 g of methacrylic acid
g and 1000 ml of benzene were placed in a flask, 3 g of sulfuric acid was added, and the reaction was carried out at 50°C for 12 hours. After the reaction, the desired transparent viscous curable phosphazene compound 34 is obtained by neutralizing, washing with water, and distilling off the benzene.
2g was obtained.
なお、このものの赤外線吸収スペクトルでは、Ｐ Ｏ
ＣＨｚ、Ｃ＝Ｃ，Ｃ＝Ｏ，Ｐ＝Ｎ、Ｐ Ｎ。In addition, in the infrared absorption spectrum of this product, P O
CHz, C=C, C=O, P=N, P N.
−ＣＦ３に起因する吸収が認められたが、−ＯＨに基づ
く吸収は全くないことから、ヘキサヒドロエトキシシク
ロトリホスファゼンとメタクリル酸との反応は１００％
進行していることがわかる。Absorption due to -CF3 was observed, but there was no absorption due to -OH, so the reaction between hexahydroethoxycyclotriphosphazene and methacrylic acid was 100%.
I can see that it is progressing.
また、上記硬化性ホスファゼン化合物のバイルシュタイ
ンテストは陰性であり、このことからこの硬化性ホスフ
ァゼン化合物には塩素は全く残存していないことが確認
された。さらに、プロトン核磁気共鳴（’Ｈ−ＮＭＲ）
スペクトルからＣＦ、ＣＨ，Ｏ−とＣＨｚ ＝ ＣＣＯ
ＯＣｚ Ｈａ Ｏ−■
ＣＨ。Furthermore, the Beilstein test of the above-mentioned curable phosphazene compound was negative, which confirmed that no chlorine remained in this curable phosphazene compound. Furthermore, proton nuclear magnetic resonance ('H-NMR)
From the spectrum, CF, CH, O- and CHz = CCO
OCz Ha O-■ CH.
との比率は７７ ： ２３であった０以上の結果よりこ
のものは下記の構造式
％式％：
で表わされる環状化合物であることがわかった。The ratio was 77:23. From the result of 0 or more, it was found that this compound was a cyclic compound represented by the following structural formula:
本発明の方法によれば、実質的に塩素原子を含有しない
硬化性ホスファゼン化合物を、高い収率で効率よく製造
することができる。According to the method of the present invention, a curable phosphazene compound containing substantially no chlorine atoms can be efficiently produced in high yield.
また、本発明の方法によって得られる硬化性ホスファゼ
ン化合物を硬化させれば、透明性、硬度。Furthermore, when the curable phosphazene compound obtained by the method of the present invention is cured, transparency and hardness can be improved.
耐熱性、耐薬品性等にすぐれた硬化性樹脂となり、各種
コーティング材、保護膜、光学レンズ、磁気記録媒体、
接着剤、顔料分散媒等に幅広くかつ有効に利用される。It is a curable resin with excellent heat resistance and chemical resistance, and is used in various coating materials, protective films, optical lenses, magnetic recording media,
Widely and effectively used in adhesives, pigment dispersion media, etc.
Claims (1)
入するにあたり、塩素含有ホスファゼン化合物を多価ア
ルコールのモノアルカリ金属塩と反応させて水酸基を有
するホスファゼン化合物を得、しかる後にアクリロイル
基あるいはメタクリロイル基含有化合物と反応させるこ
とを特徴とする硬化性ホスファゼン化合物の製造方法。(1) In introducing a polymerizable curable group into a chlorine-containing phosphazene compound, the chlorine-containing phosphazene compound is reacted with a monoalkali metal salt of a polyhydric alcohol to obtain a phosphazene compound having a hydroxyl group, and then containing an acryloyl group or a methacryloyl group. A method for producing a curable phosphazene compound, the method comprising reacting the compound with a curable phosphazene compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63060586A JPH01236241A (en) | 1988-03-16 | 1988-03-16 | Production of curable phosphazene compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63060586A JPH01236241A (en) | 1988-03-16 | 1988-03-16 | Production of curable phosphazene compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01236241A true JPH01236241A (en) | 1989-09-21 |
Family
ID=13146493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63060586A Pending JPH01236241A (en) | 1988-03-16 | 1988-03-16 | Production of curable phosphazene compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01236241A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110643046A (en) * | 2018-06-07 | 2020-01-03 | 北京化工大学 | Method for improving molecular weight and yield of polyphosphazene elastomer |
-
1988
- 1988-03-16 JP JP63060586A patent/JPH01236241A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110643046A (en) * | 2018-06-07 | 2020-01-03 | 北京化工大学 | Method for improving molecular weight and yield of polyphosphazene elastomer |
| CN110643046B (en) * | 2018-06-07 | 2021-04-02 | 北京化工大学 | Method for improving molecular weight and yield of polyphosphazene elastomer |
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