JP3357408B2 - Azide polyether - Google Patents
Azide polyetherInfo
- Publication number
- JP3357408B2 JP3357408B2 JP00020993A JP20993A JP3357408B2 JP 3357408 B2 JP3357408 B2 JP 3357408B2 JP 00020993 A JP00020993 A JP 00020993A JP 20993 A JP20993 A JP 20993A JP 3357408 B2 JP3357408 B2 JP 3357408B2
- Authority
- JP
- Japan
- Prior art keywords
- azide
- general formula
- polyether
- represented
- group
- 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.)
- Expired - Fee Related
Links
- 229920000570 polyether Polymers 0.000 title claims description 31
- 239000004721 Polyphenylene oxide Substances 0.000 title claims description 28
- 150000001540 azides Chemical class 0.000 title claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- 239000003380 propellant Substances 0.000 description 10
- 239000004014 plasticizer Substances 0.000 description 8
- -1 azide compounds Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 239000007809 chemical reaction catalyst Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- JSOGDEOQBIUNTR-UHFFFAOYSA-N 2-(azidomethyl)oxirane Chemical compound [N-]=[N+]=NCC1CO1 JSOGDEOQBIUNTR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- VAYMIYBJLRRIFR-UHFFFAOYSA-N 2-tolyl isocyanate Chemical compound CC1=CC=CC=C1N=C=O VAYMIYBJLRRIFR-UHFFFAOYSA-N 0.000 description 1
- XVLDLRUWOGLKIT-UHFFFAOYSA-N 3-(azidomethyl)-3-methyloxetane Chemical compound [N-]=[N+]=NCC1(C)COC1 XVLDLRUWOGLKIT-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 150000001622 bismuth compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920002755 poly(epichlorohydrin) Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明はヒドロキシターミネーテ
ッドアジ化ポリエーテルの末端水酸基を、一部又は全部
ウレタン化したアジ化ポリエーテルに関する。更に詳し
くは、ダクテッドロケットモーター用ガス発生剤、推進
薬、発射薬等の物性改良剤、可塑剤として有用なアジ化
ポリエーテルに関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an azide polyether obtained by partially or entirely urethanizing a terminal hydroxyl group of a hydroxy terminated azide polyether. More specifically, the present invention relates to an azide polyether useful as a physical property improving agent such as a gas generating agent for a ducted rocket motor, a propellant, a propellant, and a plasticizer.
【０００２】[0002]
【従来の技術】ヒドロキシターミネーテッドアジ化ポリ
エーテルとしては、ポリエピクロルヒドリンとアジ化ナ
トリウムとを反応させて得られる、一般式 （ＩＶ）2. Description of the Related Art Hydroxy-terminated azide polyethers are prepared by reacting polyepichlorohydrin with sodium azide.
【０００３】[0003]
【化４】 Embedded image
【０００４】（式中、ｐ は正数を示す。）で表される
グリシジルアジドポリマーが知られている（米国特許第
4268450号参照）。又、3,3'−ビスクロルメチルオキセ
タンとアジ化ナトリウムを反応させて得られる3,3'−ビ
スアジドメチルオキセタンを重合した、一般式（Ｖ）A glycidyl azide polymer represented by the formula (where p represents a positive number) is known (US Pat.
No. 4268450). Further, 3,3′-bischloromethyloxetane obtained by reacting sodium azide with 3,3′-bischloromethyloxetane is polymerized by general formula (V).
【０００５】[0005]
【化５】 Embedded image
【０００６】（式中、p は正数を示す。）で表される3,
3'−ビスアジドメチルオキセタンポリマーが知られてい
る（米国ADレポート AD A083770 、高エネルギーアジド
化合物参照）。(Where p is a positive number)
3'-Bisazidemethyloxetane polymers are known (see US AD report AD A083770, high energy azide compounds).
【０００７】これらヒドロキシターミネーテッドポリマ
ーは、通常、ヘキサメチレンジイソシアネート(HMDI)、
イソホロンジイソシアネート(IPDI)、トリレンジイソシ
アネート(TDI) 等のジイソシアネート化合物を用いて、
ヒドロキシル基とイソシアネート基との反応つまりウレ
タン化反応をさせ高エネルギーバインダーとして用いら
れている。[0007] These hydroxy-terminated polymers are usually hexamethylene diisocyanate (HMDI),
Using a diisocyanate compound such as isophorone diisocyanate (IPDI) and tolylene diisocyanate (TDI),
It is used as a high energy binder by reacting a hydroxyl group with an isocyanate group, ie, a urethanation reaction.
【０００８】更に、これらの高エネルギーバインダーを
ガス発生剤や推進薬、発射薬として用いる場合、混合時
の製造性向上（粘度低下）及び物性改良のため、ジブチ
ルフタレート(DBP) 、ジオクチルアジペート(DOA) 、ジ
オクチルセバケート(DOS) 等の可塑剤を多量に添加して
いた。Further, when these high energy binders are used as a gas generating agent, a propellant, or a propellant, dibutyl phthalate (DBP), dioctyl adipate (DOA) are used in order to improve productivity (decrease in viscosity) and physical properties upon mixing. ), And a large amount of a plasticizer such as dioctyl sebacate (DOS).
【０００９】[0009]
【発明が解決しようとする課題】しかし、これら可塑剤
を用いた場合、製造性は改良されるものの、物性低下や
マイグレーション等を引き起こすことがあった。更に推
進薬、発射薬のエネルギー低下は防ぎようもなく、高エ
ネルギーバインダーを使うメリットを消滅させていた。
そこで、高エネルギーを保ったままで物性を改良し、製
造性も向上する可塑剤が強く望まれていた。However, when these plasticizers are used, the productivity may be improved, but the physical properties may be deteriorated or migration may occur. In addition, the energy of propellants and propellants cannot be prevented from decreasing, and the advantage of using a high energy binder has been lost.
Therefore, a plasticizer that improves physical properties while maintaining high energy and also improves manufacturability has been strongly desired.
【００１０】[0010]
【課題を解決するための手段】本発明者らは、従来バイ
ンダーとして用いてきたアジ化ポリマーについて鋭意検
討した結果、ヒドロキシターミネーテッドアジ化ポリマ
ーの末端水酸基に注目し、その一部又は全部をイソシア
ン酸エステルによりウレタン化することによって得られ
るアジ化ポリエーテルが可塑剤として有用であることを
見出し、本発明を完成した。即ち、本発明は、一般式
（Ｉ）で表されるアジ化ポリエーテル、およびその製造
方法を提供するものである。Means for Solving the Problems As a result of intensive studies on azide polymers conventionally used as binders, the present inventors focused on terminal hydroxyl groups of hydroxy-terminated azide polymers, and partially or wholly used isocyanate. The present inventors have found that an azide polyether obtained by urethanization with an acid ester is useful as a plasticizer, and completed the present invention. That is, the present invention provides an azide polyether represented by the general formula (I) and a method for producing the same.
【００１１】[0011]
【化６】 Embedded image
【００１２】（式中、m は１以上の正数、n は０又は１
以上の正数で、 m＋n は２以上である。R はアジド基含
有ポリエーテル残基、X はアルキル基又はアリール基を
示す。） 一般式（Ｉ）において、R で示されるアジド基含有ポリ
エーテル残基は、式(Where m is a positive number of 1 or more, and n is 0 or 1)
With the above positive numbers, m + n is 2 or more. R represents an azide group-containing polyether residue, and X represents an alkyl group or an aryl group . ) In the general formula (I), azido group-containing polyether residue represented by R has the formula
【００１３】[0013]
【化７】 Embedded image
【００１４】 （式中、p は正数、 x，y は正数で１≦ x＋y ≦７であ
る。） で表される基から選ばれる。また Xで示されるアルキル
基又はアリール基は、 CH3−、C2H5−、C3H7−、C4H9−
等のアルキル基、[0014] (wherein, p is a positive number, x, y is 1 ≦ x + y ≦ 7 at a positive number.) Ru is selected from the group represented by. Alkyl represented by X
The group or the aryl group is CH 3- , C 2 H 5- , C 3 H 7- , C 4 H 9-.
Alkyl groups such as
【００１５】[0015]
【化８】 Embedded image
【００１６】で表されるアリール基から選ばれる。本発
明の一般式（Ｉ）で表されるアジ化ポリエーテルは、一
般式（II）Is selected from the aryl groups represented by The azide polyether represented by the general formula (I) of the present invention has the general formula (II)
【００１７】[0017]
【化９】 Embedded image
【００１８】（式中、m, nおよびR は前記と同じ意味を
示す。）で表されるヒドロキシターミネーテッドアジ化
ポリエーテルの末端水酸基の一部又は全部を、一般式(I
II) X−N＝C＝O (III) （式中、X は前記と同じ意味を示す。）で表されるイソ
シアン酸エステルによりウレタン化することにより得ら
れる。(Wherein, m, n and R have the same meanings as described above), and part or all of the terminal hydroxyl groups of the hydroxy-terminated azide polyether represented by the general formula (I)
II) X-N = C = O (III) (wherein X has the same meaning as described above), which is obtained by urethanization with an isocyanate ester.
【００１９】本発明の一般式（II）で表されるヒドロキ
シターミネーテッドアジ化ポリエーテルとしては、R が
アジド基含有ポリエーテル鎖で構成された化合物、例え
ば、前記一般式 (IV) 又は（Ｖ）で表されるものや、一
般式 (VI)As the hydroxy-terminated azide polyether represented by the general formula (II) of the present invention, a compound in which R is an azide group-containing polyether chain, for example, the above-mentioned general formula (IV) or (V) ) Or the general formula (VI)
【００２０】[0020]
【化１０】 Embedded image
【００２１】（式中、p は前記と同じ意味を示す。）で
表されるヒドロキシターミネーテッド３−アジドメチル
−３−メチルオキセタンポリマー等を用いることができ
る。更に、一般式（ＶＩＩ）(Wherein p has the same meaning as described above), for example, a hydroxy-terminated 3-azidomethyl-3-methyloxetane polymer can be used. Furthermore, the general formula (VII)
【００２２】[0022]
【化１１】 Embedded image
【００２３】（式中 ｘ，y は前記と同じ意味を示
す。）で表される、前記一般式（Ｖ）で表される化合物
と一般式 (VI) で表される化合物の共重合物や、一般式
(VIII)(Wherein x and y have the same meanings as described above), a copolymer of the compound represented by the general formula (V) and the compound represented by the general formula (VI), , General formula
(VIII)
【００２４】[0024]
【化１２】 Embedded image
【００２５】（式中 x，y は前記と同じ意味を示す。）
で表される前記一般式（Ｖ）で表される化合物と市販の
テトラヒドロフランとの共重合物等を用いることが出来
る。これら化合物の数平均分子量としては、約 200〜30
00程度が好ましく、 500〜2000程度が更に好ましい。(In the formula, x and y have the same meanings as described above.)
Copolymers of the compound represented by the general formula (V) represented by the following formula with a commercially available tetrahydrofuran and the like can be used. The number average molecular weight of these compounds is about 200 to 30
About 00 is preferable, and about 500-2000 is more preferable.
【００２６】又、一般式(III) で表されるイソシアン酸
エステルとしては、イソシアン酸メチル、イソシアン酸
エチル、イソシアン酸ブチル、イソシアン酸プロピル、
イソシアン酸フェニル、イソシアン酸メチルフェニル等
が挙げられる。The isocyanate represented by the general formula (III) includes methyl isocyanate, ethyl isocyanate, butyl isocyanate, propyl isocyanate,
Examples include phenyl isocyanate and methylphenyl isocyanate.
【００２７】上記一般式（II）で表されるヒドロキシタ
ーミネーテッドアジ化ポリエーテルと一般式(III) で表
されるイソシアン酸エステルとを反応させて一般式
（Ｉ）で表される本発明のアジ化ポリエーテルを製造す
る方法としては、公知のウレタン化方法が適用できる。
つまり、一般式（II）で表されるヒドロキシターミネー
テッドアジ化ポリエーテルと、この末端水酸基の一部又
は全部の水酸基のウレタン化反応を行うために必要な量
の一般式(III) で表されるイソシアン酸エステルと、反
応触媒とを一括して反応させる方法である。ここで用い
られる反応の触媒としては、公知のウレタン化反応触媒
が使用でき、例えば、ジブチルスズジラウレート(DBTD
L) 、ジブチルスズ（２−エチルヘキソエート）等の有
機スズ化合物や、トリフェニルビスマス等の有機ビスマ
ス化合物及びトリエチレンジアミン等のアミン類が用い
られる。また反応条件としては、反応温度は50〜80℃、
反応時間は２〜24時間の範囲が好ましい。The hydroxy-terminated azide polyether represented by the general formula (II) is reacted with an isocyanate ester represented by the general formula (III) to obtain the compound of the present invention represented by the general formula (I). As a method for producing the azide polyether, a known urethanization method can be applied.
In other words, the hydroxy-terminated azide polyether represented by the general formula (II) and an amount of the general formula (III) necessary for performing a urethanization reaction of a part or all of the terminal hydroxyl groups with the hydroxyl group are represented by the following formula: In this method, the isocyanate ester and the reaction catalyst are reacted at once. As the reaction catalyst used here, known urethanation reaction catalysts can be used, for example, dibutyltin dilaurate (DBTD
L), an organic tin compound such as dibutyltin (2-ethylhexoate), an organic bismuth compound such as triphenylbismuth, and an amine such as triethylenediamine. As reaction conditions, the reaction temperature is 50 to 80 ° C,
The reaction time is preferably in the range of 2 to 24 hours.
【００２８】[0028]
【発明の効果】本発明の一般式（Ｉ）で表されるアジ化
ポリエーテルは、ダクテッドロケットモーター用ガス発
生剤、推進薬、発射薬等の物性改良剤、可塑剤として用
いることにより、燃焼エネルギーを低下させることな
く、物性コントロールを可能にする。これは本発明のア
ジ化ポリエーテルの化学構造がバインダー主成分である
ポリエーテルの化学構造に近いため、分子間の相溶性が
向上し、推進薬、発射薬用の可塑剤としては極めて優れ
た効果を有するためと考えられる。また、一般式（II）
で表されるヒドロキシターミネーテッドアジ化ポリエー
テルを一般式(III)で表されるイソシアン酸エステルと
反応させて、一般式（Ｉ）で表される本発明のアジ化ポ
リエーテルを合成した後、これらを単離精製せずに可塑
剤として使用可能な、いわゆる通し作業で行なえるの
で、作業効率も非常に良い。According to the present invention, the azide polyether represented by the general formula (I) can be used as a gas generating agent for a ducted rocket motor, a physical property improving agent such as a propellant and a propellant, and a plasticizer to be used. Enables physical property control without reducing energy. This is because the chemical structure of the azide polyether of the present invention is close to the chemical structure of the polyether which is the main component of the binder, so that the compatibility between molecules is improved, and it is an extremely excellent effect as a plasticizer for propellants and propellants. It is considered to have. The general formula (II)
Is reacted with the isocyanate ester represented by the general formula (III) to synthesize the azide polyether of the present invention represented by the general formula (I), These can be used as a plasticizer without isolating and purifying them, that is, they can be performed by a so-called pass-through operation.
【００２９】[0029]
【実施例】以下、本発明を実施例により更に具体的に説
明するが、本発明はこれらの実施例に限定されるもので
はない。EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
【００３０】実施例１ 表１の実施例１の欄に示すヒドロキシターミネーテッド
グリシジルアジ化ポリマー100 重量部と、DBTDL 0.005
重量部とを60℃において真空混和を15分間行った。次い
で表１の実施例１の欄に示すイソシアン酸フェニル12.3
2 重量部（ポリエーテルの水酸基含有量に対し 0.5当
量）を加え、十分窒素置換した後、60℃において４時間
攪拌し反応を終了しアジ化ポリエーテルを得た。このも
のは、赤外線吸収スペクトル、核磁気共鳴スペクトル、
元素分析により、表２の実施例１の欄に示す構造を有す
る片側末端にウレタン結合をもつアジ化ポリエーテルで
あった。又、水酸基価は、60 mgKOH／ｇであった。Example 1 100 parts by weight of the hydroxy-terminated glycidyl azide polymer shown in the column of Example 1 in Table 1 and 0.005 parts of DBTDL.
The mixture was vacuum-mixed at 60 ° C for 15 minutes. Then, phenyl isocyanate 12.3 shown in the column of Example 1 in Table 1 was used.
After adding 2 parts by weight (0.5 equivalent to the hydroxyl group content of the polyether) and sufficiently replacing the atmosphere with nitrogen, the mixture was stirred at 60 ° C. for 4 hours to complete the reaction to obtain an azide polyether. This is an infrared absorption spectrum, a nuclear magnetic resonance spectrum,
According to elemental analysis, it was an azide polyether having a structure shown in the column of Example 1 in Table 2 and having a urethane bond at one end. Further, the hydroxyl value was 60 mgKOH / g.
【００３１】実施例２〜８ 実施例１に準じて、表１の実施例２〜８の欄に示す各種
ヒドロキシターミネーテッドアジ化ポリエーテルと、各
種イソシアン酸エステルを、表１に示す反応温度および
時間で反応させアジ化ポリエーテルを得た。これらの生
成物は実施例１と同様の方法で、表２に示すような構造
を有するアジ化ポリエーテルであることを確認し、水酸
基価の測定を行った。その結果を表２に示した。Examples 2 to 8 According to Example 1, various hydroxy-terminated azide polyethers shown in the columns of Examples 2 to 8 of Table 1 and various isocyanates were reacted at the reaction temperature and temperature shown in Table 1. The reaction was carried out for a time to obtain an azide polyether. These products were confirmed to be azide polyethers having the structure shown in Table 2 in the same manner as in Example 1, and the hydroxyl value was measured. The results are shown in Table 2.
【００３２】[0032]
【表１】 [Table 1]
【００３３】[0033]
【表２】 [Table 2]
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) C06D 5/00 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. 7 , DB name) C06D 5/00 CA (STN) REGISTRY (STN)
Claims (2)
テル。 【化１】 （式中、m は１以上の正数、n は０又は１以上の正数
で、 m＋n は２以上である。R はアジド基含有ポリエー
テル残基、X はアルキル基又はアリール基を示す。）1. An azide polyether represented by the general formula (I). Embedded image (In the formula, m is a positive number of 1 or more, n is 0 or a positive number of 1 or more, and m + n is 2 or more. R represents an azide group-containing polyether residue, and X represents an alkyl group or an aryl group . )
で、 m＋n は２以上である。R はアジド基含有ポリエー
テル残基を示す。） で表されるヒドロキシターミネーテッドアジ化ポリエー
テルの末端水酸基の一部又は全部を、一般式(III) X−N＝C＝O (III) （式中、X はアルキル基又はアリール基を示す。） で表されるイソシアン酸エステルによりウレタン化する
ことを特徴とする請求項１記載のアジ化ポリエーテルの
製造方法。2. A compound of the general formula (II) (In the formula, m is a positive number of 1 or more, n is 0 or a positive number of 1 or more, and m + n is 2 or more. R represents an azide group-containing polyether residue.) Part or all of the terminal hydroxyl groups of the azide polyether are represented by the following general formula (III): X-N = C = O (III) (wherein X represents an alkyl group or an aryl group ). 2. The method for producing an azide polyether according to claim 1, wherein the urethane is formed with an ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP00020993A JP3357408B2 (en) | 1993-01-05 | 1993-01-05 | Azide polyether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP00020993A JP3357408B2 (en) | 1993-01-05 | 1993-01-05 | Azide polyether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06199769A JPH06199769A (en) | 1994-07-19 |
| JP3357408B2 true JP3357408B2 (en) | 2002-12-16 |
Family
ID=11467582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP00020993A Expired - Fee Related JP3357408B2 (en) | 1993-01-05 | 1993-01-05 | Azide polyether |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3357408B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0421167D0 (en) * | 2004-09-23 | 2004-10-27 | Sec Dep For Defence Awe The | Novel energetic polyphosphazenes |
-
1993
- 1993-01-05 JP JP00020993A patent/JP3357408B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06199769A (en) | 1994-07-19 |
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