JPS58154591A - Preparation of monomer analogous to phospholipid - Google Patents
Preparation of monomer analogous to phospholipidInfo
- Publication number
- JPS58154591A JPS58154591A JP57036868A JP3686882A JPS58154591A JP S58154591 A JPS58154591 A JP S58154591A JP 57036868 A JP57036868 A JP 57036868A JP 3686882 A JP3686882 A JP 3686882A JP S58154591 A JPS58154591 A JP S58154591A
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- JP
- Japan
- Prior art keywords
- formula
- reacting
- general formula
- tertiary amine
- 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.)
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Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
本発−Ｕ、ｌＪン脂負餉似モノｑ −０製造沫に関する
ものであって、さらに詳しくは、下記−〔（Ｉ）式中、
１（Ｉｉｊ水＊＃子又はアルキル基を示し、ムは有機基
を示し、Ｒ２、Ｒ１およびＨ４Ｆ１アルキル基を示す、
但し Ｒ１およびＢｓは相互に連結Ｅ、て環を形紙して
ｂて賜よい、〕
本発明は、上記リン脂気類似七ノ！−の礁めて簡単で一
収率の製造プロセスを提供することを目的とし５、この
目的は本発明方法に従い、下記一般式（１）で表わされ
る化合物と。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the product produced by the present invention - U, IJ Ngang Soybean-like monoq-0, and more specifically relates to the following - [(I) in the formula,
1 (Iij represents water *# child or an alkyl group, Mu represents an organic group, R2, R1 and H4F1 represent an alkyl group,
However, R1 and Bs may be connected to each other to form a ring.] The present invention provides the above-mentioned phospholipid-like seven! - It is an object of the present invention to provide a particularly simple and high-yield production process for the production of a compound represented by the following general formula (1) according to the method of the present invention.
ａｕ、＝ａ−Ａ−Ｏｍ （
置）ｉ（＋
〔（厘）式中 Ｒ１およびムは前足一般式（１）におを
するＪｌ ＊ ｔｉｃ同じ〕
一一りロローーーオキソー／、３．λ−ジオキサホスホ
ランとを、第三級アミン存在下に反応させて、下１一般
式（ｉ＋＋）で表わされる化合物を製造し。au, = a-A-Om (
1) i(+ [In the (厘) formula, R1 and M are the same as Jl * tic in the front foot general formula (1)] , and reacted in the presence of a tertiary amine to produce a compound represented by the following general formula (i++).
〔（履）式中 Ｂ′およびムけ前足一般式（１） Ｋお
ける意義に同じ〕
次いで、一般式（璽）で表わされ易化合＃ＩＩＪを。[Same meaning as in B' in the formula (1) and K in the general formula (1)] Next, the easy compound #IIJ represented by the general formula (seal).
下記一般式（■）で表わされる第三級アきントヲ反応さ
せるプロセスによって連成される。It is coupled by a process of reacting a tertiary akinto compound represented by the following general formula (■).
、Ｈｍ
Ｍ−Ｒ” （ＩＶ）
＼Ｒ４
［（ＩＶ）式中、 Ｒ”、Ｒ’ オｊ ヒＲ’ｔ［示一
般式（１）における意義にＩＷｌじ］
本発明を詳細にＩ！２明するに、前足一般式（量）で構
わされる化合物としては、ムが−０−０−１：ＯＨ，ｊ
錦
（ここでｎは／〜／ＪのＩ／１１＃を示す）。, Hm MR" (IV) \R4 [In the formula (IV), R", R' hi R't [IWl same as the meaning in the general formula (1)] The present invention will be described in detail in I! 2. To clarify, as a compound with the general formula (amount) of the forefoot, mu is -0-0-1:OH,j
Nishiki (here n indicates I/11# of /~/J).
−Ｃ−ＮＩＩ＋ｅｎ、＋ｍ（ここでｍは／〜Ｉのｍ数を
示すχ１
−０−０＋ＯＨ，入０Ｈ（−ＯＲ，＋ｔＯＨ，（ここで
、４は１〜３＋１ １
の釡数を示し％ｔＦｉｏ−一の！＆数を示す）又は化合
物が挙けられる・具体例を駆けれＶ！、次の通り。-C-NII+en, +m (here, m indicates the m number of /~I χ1 -0-0+OH, 0H (-OR, +tOH, (here, 4 indicates the number of pots from 1 to 3+1 1 %tFio - One! & indicates the number) or compounds are listed. - Give specific examples V!, as follows.
？・ １、、．０−００．（ｃａ、）、０ｎ Ｇｌｉ。?・ 1,,. 0-00. (ca,),0n Gli.
Ｕｌｉ、＝ｃ−ｃｏ、（ｃｈ、 ）、ＯＲＵｉｉ、＝
ａ−ｏｏ、 （ＯＨ，）、ｏＯｋｉａＨ，＝ ０ｎ−ｃ
ｏｌＪｉｉｃｌｉ、ｏｎａｉｌ！２＝ａＨ−ｃｏ、ａＨ
，ｃＨｃ）！。Uli,=c-co,(ch, ),ORUii,=
a-oo, (OH,), oOkiaH, = 0n-c
ol Jiicli, onail! 2=aH-co, aH
,cHc)! .
Ｅ
上記化合物と反応させる一−クロａ −Ｊ−オキソ−／
、ｊ、ｊ−ジオキサホスホランは、下記式（Ｖ）て表
わされる化合物である。E 1-chloroa-J-oxo-/ to be reacted with the above compound
, j,j-dioxaphosphorane is a compound represented by the following formula (V).
反応の際に使用される第三級７建ンとしては、トリメチ
ルアミン、トリエチルアミンなどのトリプルキルアミン
が挙げられる。Examples of the tertiary compound used in the reaction include triplekyl amines such as trimethylamine and triethylamine.
前示両反ｉｂｈ分および第三級アミンの菅用量は、相互
にはｙ等モルでよい、ｂＬ応の際に＊用される溶媒とし
ては１内戚分、菖三級アｉンおよび反応生Ｗｔ物を淋解
しうるものが好ましく、例えば、ジエチルエーテル、テ
トラヒドロフランなどが挙けられゐ０反応は、＃媒中で
、両賊分および第三級アきンを混合し、−ＪＯｒ：ない
し０℃で３０分ないし数時間反応させれ−ばよ〈。The above-mentioned amounts of both anti-ibh components and tertiary amines may be equimolar to each other.The solvent used in the bL reaction is It is preferable to use a substance that can decompose raw Wt, such as diethyl ether, tetrahydrofuran, etc. In the reaction, the amphoteric component and the tertiary aquine are mixed in # medium, and -JOr: Let it react for 30 minutes to several hours at 0°C to 0°C.
下記反応式で貴わされる反応によ）゛、一般式（ｍｌ）
で−わされる化合物が、ｔｔ ｓ定量的に祷られ易。According to the reaction expressed by the following reaction formula), general formula (ml)
It is easy to quantitatively determine the compound to be treated with tts.
Ｒ１（Ｊ
（Ｉｌｌ）
副生物の第三級アミンーー塩は、通常、沈澱す４（／＋
で、＠易に分離しうる・
次に、−飯式（ＩＩＩ）で表わさねる化合物をさらに第
三蘇アミンと反応させる方法について歌明す４０ここで
使用される第三級アミンは、薊ボー叡式（１ｖ）で示さ
れる化合物であり、Ｒ８およびＲ３としては、メチル基
、エチル基のほかに両者が結合【てビリジ＞塊を形紙し
たものでもよく。R1(J (Ill) By-product tertiary amine-salt usually precipitates 4(/+
Next, we describe a method for further reacting the compound represented by formula (III) with a tertiary amine.40The tertiary amine used here is This is a compound represented by the formula (1v), and R8 and R3 may be a methyl group, an ethyl group, or a paper-shaped viridi agglomerate in which both are bonded.
Ｒ４と１てはメチル基、エチル基勢が挙けられる。Examples of R4 and 1 include a methyl group and an ethyl group.
Ｊ４１４ ｈとしてハ、トリメチルアミン、トリメチル
アミン等が皐けられる。使用′Ｍは、一般式（ｌｆｔ）
で衣わさ７′Ｉ々化合物に対し等七ル以上であればよい
・
反応の際に使用される＃線としては、アセトニトリル、
メタノールマタはジメチルホルムアミドが好ましい０反
応は、溶媒中で、 ＩＩＩＩＩＩＬ分を混合し、室温〜
１０９ｃ程度の温度で数時間〜十数時間反応させねば、
下記反応式で表わされる反応によ如、一般式（１）で表
わされる化合−が高収率にて得られる・
（１）
反応生地物である（１）式の化合物は、り０ｇホルムま
たはメタノールに俗解し、次いで大量の７七トン中に加
えて析出させることにより、容易に′ｎｉ製Ｅ、うる。J414h includes trimethylamine, trimethylamine, etc. Use 'M' is the general formula (lft)
It is sufficient if it is equal to or higher than 7' for the compound.The # line used in the reaction is acetonitrile,
For methanol, dimethylformamide is preferred. 0 Reaction: Mix IIIIIIL components in a solvent and heat at room temperature to
If you have to react at a temperature of about 109c for several hours to more than ten hours,
By the reaction represented by the reaction formula below, the compound represented by general formula (1) can be obtained in high yield. It can be easily obtained by mixing it with methanol and then adding it to a large amount of 77 tons to precipitate it.
このようにして得られた（１）式の化合物は、ラジカル
１合法により容易に１合することができ、リンＢＦＩ負
の憔性基を側鎖にもつビニル高分子Ｖ得ることができゐ
、そして該高分子は、能動輸送層の材料などの用途が期
待される。The compound of formula (1) thus obtained can be easily combined by the radical 1 method to obtain a vinyl polymer V having a phosphorus BFI negative solubility group in the side chain. The polymer is expected to be used as a material for active transport layers.
次に本発明を実施例によりさらに詳細に綾明する。Next, the present invention will be explained in more detail with reference to Examples.
Ｃｈｅｍｉｓｔｒｙ ａｎｄ 工ｎｄｕｓｔｒｙ、
Ｏｃｔ、 ２０． （／り６コ）。Chemistry and industry,
Oct, 20. (/ri6).
／ｌ１ｒ２１記載のＲ，８，ｌｄｍｕｎｄｓｏｎの方法
に沿って行った・
一一りロロー／、３．２−ジオキサホスホランθ、ｉモ
ルを乾燥ベンゼン１００−に触触した・この浴液に塞温
で、乾燥酸素を１時間通じた。The process was carried out according to the method of R, 8, ldmundson described in /l1r21. One mole of Rolow/3,2-dioxaphosphorane θ was brought into contact with 100-mol of dry benzene. At room temperature, dry oxygen was passed for 1 hour.
＃４腋ｒまや＋発熱した。鹸化反応後、蒸留により。#4 Armpit irritation + fever. After saponification reaction, by distillation.
りｊ嶌の収量で■を得た。融点３２〜ダ一℃で文躯蝋と
一敦した・
ン（■、ｎ−一）の台底
ヒドロオキシエチルメタクリレート／ Ｊ、Ｏｆ（０，
７モル）トトリエチルアきンｆ、Ｊ ｊ ｆ（０，／
Ｏ７モル）を乾燥し大ジエチルエーテル／！Ｏｄに入れ
、−ａｏ℃Ｖｃ冷却しつつ、実施＄４１− ／で台地し
た化合物■／４ｔ、コｚ ｔ （ｏ、ｉモル）を滴下し
た０滴下中は反応温度をｍ−０１１〜−１０℃に保った
・論下終了後、水冷下一時間撹拌を続けた。Ｉ！にｉｉ
！髄で３０分関反応させた１反応終了後、トリメチルア
ミンｔｊ［塩を除去し、ジエチルエーテルを完全に曽去
して■（ｎ−コ）ｔ−１また。仁のものは粘＃Ｉ４な筐
体でめったｅＩＭＡ誌は元素分析とＭＭＲＸＢで行つえ
。■ was obtained for the yield of lily. Hydroxyethyl methacrylate with a melting point of 32 to 1°C and a base of (■, n-1) / J, Of (0,
7 mol) triethyl aquine f, J j f(0,/
O7 mol) is dried and converted into large diethyl ether/! During the dropwise addition, the reaction temperature was set at m-011 to -10. The temperature was maintained at ℃. After the completion of the reaction, stirring was continued for 1 hour while cooling with water. I! ii
! After 30 minutes of reaction with marrow, remove trimethylamine tj [salt, completely remove diethyl ether, and add (n-co)t-1. Jin's eIMA magazine, which was rarely found in a sticky #I4 case, was subjected to elemental analysis and MMRXB.
元素分析−〇（計算値＊ｏ、ｔｔ、分値値＋１／、／／
）Ｈ（計算値Ｊ、ｊ ／、分析値ｊ、４ ｊ ）、収率
はｙｔＸであった。ＩＲは籐３図、ＭＭＲは第１図の通
り。Elemental analysis -〇(calculated value *o, tt, minute value +1/, //
)H (calculated value J, j /, analyzed value j, 4 j ), yield was ytX. IR is as shown in Figure 3 and MMR is as shown in Figure 1.
実施汐１−１−一で合成した■（ｎ−λ）？、Ｑ ＠
ｆ（０，０９モル）とトリメチルアミン／ ／、ｔ ｆ
（０，２モル）及びアセトニトリルｔＯｄを、耐圧反応
管に人ね、１０℃で１０時時間上り反応させた。反茫慎
すぐに減圧線輪［、た。この段階で粘稠な液体１得たが
、冷所で数日間保存しておくと、白色の結晶になった。■(n-λ)? synthesized in Example 1-1-1. , Q @
f (0,09 mol) and trimethylamine / /, t f
(0.2 mol) and acetonitrile tOd were placed in a pressure-resistant reaction tube and reacted at 10° C. for 10 hours. The decompression line was immediately turned off. At this stage, a viscous liquid 1 was obtained, which turned into white crystals after being stored in a cool place for several days.
粗部率はぼ／θＱ九。簡便で確実な鞘製法としては、粘
稠な液体をクロロホルムに洛かし、アセトン中に析田さ
せる方法がある。この方法で行うと、との反えで剛生す
る、忌ら＜、Ｕ−（メタクロイルオキシ）エチル−２ｔ
−（ヒドロオキシエチル） ２ａｔ−（トリメチルア
ンモニウム）リン酸を除去でさる。鞘製品の収率りθ〜
Ｐｊ％、確認は元木分伯と、ＮＭＲｌＩＲで行った６元
本分析：０（＋！ｔｊＬ 櫨 ３９．−一 −一、 分
権１■イＩａｏ、２ ｏ ） 、’ｋｌ（ν［［算憧
２．り／、分析値７ｊｒ）、Ｎ（計算値ダ・４３・分析
値３．ｒ Ｐ ）合成ｗＩＩＪＦｉ強い畝湿性を示した
・工りは第ダ図、 ｌＩＭＲは第１図の通シ。The gross portion rate is BO/θQ9. A simple and reliable method for producing pods is to dissolve a viscous liquid in chloroform and precipitate it in acetone. When carried out in this manner, U-(methacroyloxy)ethyl-2t
-(hydroxyethyl) 2at-(trimethylammonium) phosphoric acid is removed. Yield of sheath product θ~
Pj%, confirmed by Bunhaku Motoki and 6-principal analysis conducted with NMRlIR: 0 (+! 2.ri/, analytical value 7jr), N (calculated value 43, analytical value 3.rP) composite wIIJFi showed strong ridge moisture. .
爽り例−に −一（メタクルロイルオキシ）エチルーコ
’−（）リメチルアンモニウム）へキサヒドロオキシエ
チルメタクリレートの代ｐに。Refreshing Example - To -(methacryloyloxy)ethyl-()-(limethylammonium)hexahydroxyethyl methacrylate.
ヒドロオキシへキサメチレンメタクリレートを用いた以
外＃′ｉ、実論例−Ｊ、−７と同様に行った。収率ｔｓ
Ｘ、元素分析、（計算値−分析値）０ （ｊ ９．！
？、ダθ、２０）、Ｈ（７，Ｐ／、 ７，４／）Ｎ （
４ｔ、コ３．３７ｐ）ｅ
酸の合成
ヒドロオキシエチルメタクリレートの伏動に。The same procedure as #'i, Practical Examples -J and -7 was carried out except that hydroxyhexamethylene methacrylate was used. Yield ts
X, elemental analysis, (calculated value - analyzed value) 0 (j 9.!
? , Daθ, 20), H(7,P/, 7,4/)N (
4t, Co3.37p) e Synthesis of acid To the decomposition of hydroxyethyl methacrylate.
ヒドロオキシメチルメタクリル７きドを用いた以外は、
実施例−一、−ｊと同様に何った一一一（メタクリルア
ミド）メチル−一−オキンー／、ｊ、２−ジオキサホス
ホランの収＊ｙｓｘａ最終品の収率７１九Except for using hydroxymethyl methacrylate 7,
Yield of 111(methacrylamido)methyl-1-okine/,j,2-dioxaphosphorane in the same manner as in Example-1,-j *ysxa Yield of final product 719
Ｍ／、！、−１４Ｉ−図は、そｈぞれ％−一（メタクリ
ロイルオキシ）エチルーーーオキソ−７１３、−一ジオ
キザホスホラン（■、ｎｍｕ）、Ｊ−（メタクリロイル
オキシ）エチルーー′（トリメチル１ンモニウム）エチ
ルリン＃（■、ｎ＝−）のＭＭＲ，ＩＲチャートである
。
特許出鯵人 仲 矢 忠 雄
ほか７名
代 埴 人 弁理士 長谷用 −
ほか１名
−丁続？山ｉＦ由（５式）
昭和５７年７り／３日
ｎ斤長官若杉和人殿
着の去小
昭和５７年特ムｑｙＩＩＡ第３６８６８号明の名称
リン脂質類似ｔツマ−の製造払
任をづる石
事件との関係 出願人
仲 矢 忠 雄 （ほか１名）
埋入 〒１００
東余部千代田区丸の内−丁目５番２号
二輪化成工業株式会社内
（ばか１名）
１■命令の日付 昭和５７年６月２９日（発送日）＋１
の内容M/,! , -14I- figure shows %-1(methacryloyloxy)ethyl-oxo-713, -1dioxaphosphorane (■, nmu), J-(methacryloyloxy)ethyl-'(trimethyl1 ammonium), respectively. These are MMR and IR charts of ethyl phosphorus # (■, n=-). Patent author Tadao Nakaya and 7 others, Hanito Patent attorney Haseyo - 1 other person - Dingzuki? Yama iF Yu (Type 5) July 3rd, 1981: The death of Director-General Kazuto Wakasugi of 1988, special name of IIA No. 36868, in charge of manufacturing a phospholipid-like T-summer. Relationship to the Stone Incident Applicant: Tadao Ya (and 1 other person) Embedded: Inside Niwa Kasei Kogyo Co., Ltd., 5-2 Marunouchi-chome, Chiyoda-ku, Higashiyobu, 100 Japan (1 idiot) 1.Date of order: 1988 June 29th (shipment date) +1
contents of
Claims (1)
０−ムー０剋 （厘）Ｉ 〔（Ｉ）式中、Ｒ１は水嵩原子又はアルキル基を示し、
ムは有機基を示す〕 １−りロローコーオキソー／、Ｊ、２−ジオキサホスホ
クンとを％篇三級アミン存在下に反応させて、下記一般
式（ＩＲ）で表わされる化合物を製造し、 〔（履）式中 Ｒ１およびムは、前示（璽）式中にふ・
ける意義に同じ〕 下記一般式（ｈ′）で表わされゐ第三級アｉンと反応さ
せる 〔（■）式中 １ｍ、Ｒ１およびＷはアルキル基を示す
、但し、 ＲｊおよびＲｓは相互に連結して埠を形成し
ていてもよい、〕 ことを特徴とする下記一般式（１）で表わされるリン脂
質類似モノ！−の製造法 式（Ｓ）および（Ｉｌｌｒ） Ｋおける意義に岡じ〕(1) A compound represented by the following general formula (ca) and
0-mu0剋 (厘)I [(I) In the formula, R1 represents a water bulk atom or an alkyl group,
[mu] represents an organic group] A compound represented by the following general formula (IR) is obtained by reacting 1-rirolowokoxo/,J,2-dioxaphosphokune in the presence of a tertiary amine. [R1 and M in the formula (seal) are
[same meaning as in the following] React with a tertiary amine represented by the following general formula (h') [In the formula (■), 1m, R1 and W represent an alkyl group, provided that Rj and Rs are mutually A phospholipid-like substance represented by the following general formula (1), which may be connected to form a moat! - manufacturing method (S) and (Illr)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57036868A JPS58154591A (en) | 1982-03-09 | 1982-03-09 | Preparation of monomer analogous to phospholipid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57036868A JPS58154591A (en) | 1982-03-09 | 1982-03-09 | Preparation of monomer analogous to phospholipid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58154591A true JPS58154591A (en) | 1983-09-14 |
| JPH0249316B2 JPH0249316B2 (en) | 1990-10-29 |
Family
ID=12481758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57036868A Granted JPS58154591A (en) | 1982-03-09 | 1982-03-09 | Preparation of monomer analogous to phospholipid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58154591A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995014702A1 (en) * | 1993-11-23 | 1995-06-01 | Biocompatibles Limited | Ethylenically unsaturated compounds |
| WO1995014701A1 (en) * | 1993-11-23 | 1995-06-01 | Biocompatibles Limited | Ethylenically unsaturated compounds |
| WO1996031566A1 (en) | 1995-04-03 | 1996-10-10 | Nof Corporation | Process for producing an aqueous solution of phosphorylcholine group bearing polymer and aqueous solution of phosphorylcholine group bearing polymer |
| US5599587A (en) * | 1990-11-05 | 1997-02-04 | Biocompatibles Limited | Phosphoric acid esters and their use in the preparation of biocompatible surfaces |
| WO1998054194A1 (en) * | 1997-05-30 | 1998-12-03 | Nof Corporation | Process for producing (meth)acrylate derivatives |
| US5981786A (en) * | 1997-05-30 | 1999-11-09 | Nof Corporation | Process for producing (meth)acrylate derivatives |
| WO2001034700A1 (en) | 1999-11-09 | 2001-05-17 | Nof Corporation | Composition for hydrogel, hydrogel, and use thereof |
| US7166476B2 (en) | 2000-08-29 | 2007-01-23 | Kyowa Medex Co., Ltd. | Highly reproducible agglutination immunoassay method and reagents |
| WO2012175923A1 (en) | 2011-06-24 | 2012-12-27 | Biointeractions Limited, University Of Reading | Biocompatible, biomimetic ampholyte materials |
| WO2013033554A1 (en) | 2011-09-01 | 2013-03-07 | Vertellus Specialties Inc. | Biocompatible material |
| WO2013128633A1 (en) | 2012-03-02 | 2013-09-06 | 日油株式会社 | Contact lens care preparation and packaging solution |
| CN109438516A (en) * | 2018-12-19 | 2019-03-08 | 安庆构友生物材料科技有限公司 | A method of preparing ethylene 2-(methacryloxypropyl) ethyl phosphonic acid ester |
| WO2023276858A1 (en) | 2021-06-29 | 2023-01-05 | 日油株式会社 | Soft contact lens solution |
| US11912784B2 (en) | 2019-10-10 | 2024-02-27 | Kodiak Sciences Inc. | Methods of treating an eye disorder |
-
1982
- 1982-03-09 JP JP57036868A patent/JPS58154591A/en active Granted
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5599587A (en) * | 1990-11-05 | 1997-02-04 | Biocompatibles Limited | Phosphoric acid esters and their use in the preparation of biocompatible surfaces |
| WO1995014702A1 (en) * | 1993-11-23 | 1995-06-01 | Biocompatibles Limited | Ethylenically unsaturated compounds |
| WO1995014701A1 (en) * | 1993-11-23 | 1995-06-01 | Biocompatibles Limited | Ethylenically unsaturated compounds |
| WO1996031566A1 (en) | 1995-04-03 | 1996-10-10 | Nof Corporation | Process for producing an aqueous solution of phosphorylcholine group bearing polymer and aqueous solution of phosphorylcholine group bearing polymer |
| WO1998054194A1 (en) * | 1997-05-30 | 1998-12-03 | Nof Corporation | Process for producing (meth)acrylate derivatives |
| EP0922709A1 (en) * | 1997-05-30 | 1999-06-16 | Nof Corporation | Process for producing (meth)acrylate derivatives |
| EP0922709A4 (en) * | 1997-05-30 | 1999-07-21 | ||
| US5981786A (en) * | 1997-05-30 | 1999-11-09 | Nof Corporation | Process for producing (meth)acrylate derivatives |
| WO2001034700A1 (en) | 1999-11-09 | 2001-05-17 | Nof Corporation | Composition for hydrogel, hydrogel, and use thereof |
| US7166476B2 (en) | 2000-08-29 | 2007-01-23 | Kyowa Medex Co., Ltd. | Highly reproducible agglutination immunoassay method and reagents |
| WO2012175923A1 (en) | 2011-06-24 | 2012-12-27 | Biointeractions Limited, University Of Reading | Biocompatible, biomimetic ampholyte materials |
| US9567357B2 (en) | 2011-06-24 | 2017-02-14 | Biointeractions Ltd. | Biocompatible, biomimetic ampholyte materials |
| US10251982B2 (en) | 2011-06-24 | 2019-04-09 | Biointeractions Ltd. | Biocompatible, biomimetic ampholyte materials |
| WO2013033554A1 (en) | 2011-09-01 | 2013-03-07 | Vertellus Specialties Inc. | Biocompatible material |
| WO2013128633A1 (en) | 2012-03-02 | 2013-09-06 | 日油株式会社 | Contact lens care preparation and packaging solution |
| CN109438516A (en) * | 2018-12-19 | 2019-03-08 | 安庆构友生物材料科技有限公司 | A method of preparing ethylene 2-(methacryloxypropyl) ethyl phosphonic acid ester |
| CN109438516B (en) * | 2018-12-19 | 2021-05-07 | 安庆构友生物材料科技有限公司 | Method for preparing ethylene 2- (methacryloyloxy) ethyl phosphate |
| US11912784B2 (en) | 2019-10-10 | 2024-02-27 | Kodiak Sciences Inc. | Methods of treating an eye disorder |
| WO2023276858A1 (en) | 2021-06-29 | 2023-01-05 | 日油株式会社 | Soft contact lens solution |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0249316B2 (en) | 1990-10-29 |
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