JPH02258822A - Fluorine-containing urethane compound and preparation thereof - Google Patents
Fluorine-containing urethane compound and preparation thereofInfo
- Publication number
- JPH02258822A JPH02258822A JP1081053A JP8105389A JPH02258822A JP H02258822 A JPH02258822 A JP H02258822A JP 1081053 A JP1081053 A JP 1081053A JP 8105389 A JP8105389 A JP 8105389A JP H02258822 A JPH02258822 A JP H02258822A
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- diisocyanate
- urethane compound
- containing urethane
- 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.)
- Granted
Links
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 32
- 239000011737 fluorine Substances 0.000 title claims abstract description 31
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 29
- -1 urethane compound Chemical class 0.000 title claims description 13
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 14
- 150000002009 diols Chemical class 0.000 claims abstract description 14
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 239000005057 Hexamethylene diisocyanate Substances 0.000 abstract description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 3
- 150000002605 large molecules Chemical class 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 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 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
- C08G18/3804—Polyhydroxy compounds
- C08G18/3812—Polyhydroxy compounds having fluorine atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、含フッ素ウレタン化合物およびその製造方法
１ｃ関するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a fluorine-containing urethane compound and its manufacturing method 1c.
（従来技術とその問題点）
従来のウレタン樹脂は、合成繊維１合成ゴム、フオーム
、接着剤、塗料など幅広い産業分野に利用されている。(Prior art and its problems) Conventional urethane resins are used in a wide range of industrial fields such as synthetic fibers, synthetic rubber, foams, adhesives, and paints.
しかし、従来のウレタン樹脂は、酸、アルカリなど（対
する耐薬品性、耐水性や耐湿性、および耐熱性が悪いと
い５欠点があった。これらの欠点な改善するためにポリ
フルオロアルキル基を有したウレタン化合物が検討され
ている（％開開５３−１１２８５５号公報、特開昭５４
−７４０００号公＠）、
このポリフルオロアルキル基な有したウレタン化合物は
、低分子量化合物、および高分子量化合物に分類される
が、低分子量化合物は含フッ素モノアルコールとイソシ
アネートとの反応生成物が多いためｚｉｉ体、３を体な
どのテロマーは得にくく、低分子量化合物のものが多く
、そのために溶融温度が低く、また撥水、撥油性、特に
柔軟性、加工性などがまだ十分でないといった欠点があ
った。However, conventional urethane resins have five drawbacks, such as poor chemical resistance to acids and alkalis, water resistance and humidity resistance, and poor heat resistance. urethane compounds have been studied (%Kokai No. 53-112855, JP-A-54
-74000 @), Urethane compounds with this polyfluoroalkyl group are classified into low molecular weight compounds and high molecular weight compounds, but low molecular weight compounds are often reaction products of fluorine-containing monoalcohols and isocyanates. Therefore, it is difficult to obtain telomers such as ZII and 3-isomers, and many of them are low-molecular-weight compounds, resulting in low melting temperatures and disadvantages such as insufficient water repellency, oil repellency, especially flexibility, and processability. there were.
また、高分子量化合物においても、上記の問題は必ずし
も満足されていない。Furthermore, the above-mentioned problems are not necessarily satisfied even with high molecular weight compounds.
（発明の目的）
本発明者らは上記のよ５な問題点な解決するために鋭意
研究した結果、分子中にエーテル結合な有する含フッ素
ジオールとジイソシアネートとの反応生成物が本発明の
目的に適するものであることを見出し１本発明に到達し
た。(Object of the Invention) As a result of intensive research by the present inventors in order to solve the above five problems, the reaction product of a fluorine-containing diol having an ether bond in the molecule and a diisocyanate has been found to be suitable for the purpose of the present invention. The present invention was achieved by discovering that the method is suitable.
（発明の構成）
すなわち本発明は、
１１） 炭素数４〜１０のペルフルオロアルキル基ト
、エーテル結合を分子中に含有し、かつポリマーセグメ
ント当り、少なくとも１個のウレタン結合を有する含フ
ッ素ウレタン化合物、
（２） −紋穴
（式中Ｒｆは炭素数４〜ｌＯのペルフルオロアルキル基
、ｎは１または２の整数）
で表される含フッ素ジオールと、ジインシアネートな反
応させることを特徴とする含フッ素ウレタン化合物の製
造方法、
を提供する。(Structure of the Invention) That is, the present invention comprises: 11) A fluorine-containing urethane compound containing a perfluoroalkyl group having 4 to 10 carbon atoms or an ether bond in the molecule and having at least one urethane bond per polymer segment; (2) A fluorine-containing diol characterized by reacting in a diincyanate manner with a fluorine-containing diol represented by -Momona (in the formula, Rf is a perfluoroalkyl group having 4 to 1O carbon atoms, and n is an integer of 1 or 2) A method for producing a urethane compound is provided.
本発明に係わる一般式（１）で表される含フッ素ジオー
ルにおいて、Ｒｆは炭素数４〜ｌＯのペルフルオロアル
キル基であり、好ましくは炭素数６〜８のペルフルオロ
アルキル基であり、直鎖、分岐ｔ’２４のいずれであっ
てもよい。In the fluorine-containing diol represented by the general formula (1) according to the present invention, Rf is a perfluoroalkyl group having 4 to 10 carbon atoms, preferably a perfluoroalkyl group having 6 to 8 carbon atoms, and is linear or branched. It may be any of t'24.
本発明化合物の特性である撥水、撥油性、非粘着性など
はこのペルフルオロアルキル基によって発揮されるもの
である。炭素数が４未満であると撥水、撥油性、などが
十分ではなく、また１Ｇを越えると、それ以下の場合と
比較して特性の大きな変化は認められない。The properties of the compound of the present invention, such as water repellency, oil repellency, and non-adhesiveness, are exhibited by this perfluoroalkyl group. If the number of carbon atoms is less than 4, water repellency, oil repellency, etc. will not be sufficient, and if it exceeds 1 G, no significant change in properties will be observed compared to the case of less than 1 G.
また、エーテル結合は、その柔軟性より得られたウレタ
ン化合物の柔軟性や加工性を高める効果なもたらす。Moreover, the ether bond has the effect of increasing the flexibility and processability of the obtained urethane compound due to its flexibility.
さらに、２個の水酸基は、２官能型の七ツマ−として作
用し、ジインシアネートとの反応によって高分子量の化
合物を得るために必要不可欠のものである＠
これによって、高分子量の重合物が帰られ、樹脂の硬度
、耐薬品性、耐熱性、溶融温度等を高める効果な持つ。Furthermore, the two hydroxyl groups act as a difunctional heptamer and are essential for obtaining a high molecular weight compound by reaction with diincyanate. It has the effect of increasing the hardness, chemical resistance, heat resistance, melting temperature, etc. of the resin.
本発明化合物の原料である一般式＋１）で表される化合
物は、対応する含フッ素エポキシドの開環反応によって
容易に得られる。The compound represented by the general formula +1), which is a raw material for the compound of the present invention, can be easily obtained by ring-opening reaction of the corresponding fluorine-containing epoxide.
また、本発明化合物の製造方法において、シイツクアネ
ートは直鎖、分岐鎖のいずれであってもよく、また脂肪
族、芳昏族のいずれであってもよいが、−船釣な例とし
て、ヘキサメチレンジイソシアネート（ＨＤ’Ｉ）、２
，４−トリレンジイソシネ−）（Ｊ、４−’ｌ’ＤＩ）
、メチレンビス（４−フェニルインシアネート）（ＭＤ
Ｉ ）、キシリレ／ジインシアネー）（ＸＤＩ）、３−
インクアネートメチル−３，５，５−）リメチルシクロ
ヘキシルイソシアネート（ＩｐＤＩ）等があげられるＯ
このシイツクアネートの使用量は、特に限定されないが
、−紋穴（ｘＪで示される含フッ素ジオールに対して０
．５〜１．５Ｇモル比）の間で柑いられる。In addition, in the method for producing the compound of the present invention, cytsuquanate may be linear or branched, and may be aliphatic or aromatic; Diisocyanate (HD'I), 2
,4-tolylene diisocyanate) (J, 4-'l'DI)
, methylene bis(4-phenylinocyanate) (MD
I), xylyle/diincyane) (XDI), 3-
Examples include inquanate methyl-3,5,5-)limethylcyclohexyl isocyanate (IpDI).The amount of this inquanate used is not particularly limited; 0
．． 5 to 1.5G molar ratio).
ここで、シイツクアネートの使用量が０．５付近である
と、含フッ素ジオ−／Ｉ／１分子九対しエラインシアネ
ート２分子、また１、５付近であると、ジイソシアネー
ト２分子に対して含フッ素ジオール３分子が反応したテ
ロマーが得られる。Here, if the usage amount of sitsuquanate is around 0.5, 2 molecules of elaine cyanate are used for every 9 molecules of fluorine-containing di-/I/1, and when it is around 1.5, 2 molecules of fluorine-containing diisocyanate are used for every 9 molecules of fluorine-containing diisocyanate. A telomer with three diol molecules reacted is obtained.
−万、ジイソシアネートの使用量が１付近であると、含
フッ素ジオール１分子に対してジイソシアネートも１分
子反応した高分子化合物が得られる。また、反応温度は
室温から含フッ素ジオールおよびジイソシアネートの沸
点まで変化できるが、好ましくは４０℃〜１２０℃の間
で、無溶媒、または必要に応じて適当な溶媒を用いて行
われる。If the amount of diisocyanate used is around 1,000, a polymer compound is obtained in which one molecule of diisocyanate reacts with one molecule of fluorine-containing diol. Further, the reaction temperature can vary from room temperature to the boiling point of the fluorine-containing diol and diisocyanate, but is preferably carried out between 40° C. and 120° C. without a solvent or using an appropriate solvent as necessary.
このようにして得られる本発明化合物は、含フッ素化合
物の特徴として、上記の撥水、撥油性の他に、低屈折率
、気体の選択的透過性などの緒特性も併せ持つ。The compound of the present invention thus obtained has other characteristics of a fluorine-containing compound, such as a low refractive index and selective gas permeability, in addition to the above-mentioned water and oil repellency.
次に、本発明な実施例をもって具体的に説明するが、以
下の実施例は本発明の範囲を限定するものではない。Next, the present invention will be specifically explained using Examples, but the following Examples do not limit the scope of the present invention.
実施例１
十分にＮｔパージをした、機械攪拌装置、温度計、滴下
Ｐ斗、還流器な備えた３００ｍ１三ロフラスコに、含フ
ッ素ジオール
Ｃ，Ｆ、、ＣＨ，ＱＣＨ！ ＣＨＣＨ，ＯＨ４７，４ｇ
（０，１０ｍｏ １ ）ＣＨ
を入れ、Ｎ、雰囲気下８０℃でヘキサメチレレンジイソ
シアネート１６．８ ｇ （０，１０ｍｏｌ ）を３０
分で滴下し、そのままの状態で８時間攪拌した。Example 1 Fluorine-containing diols C, F, CH, QCH! were placed in a 300 ml three-flask equipped with a mechanical stirrer, a thermometer, a dropping port, and a reflux device that had been thoroughly purged with Nt. CHCH,OH47.4g
(0,10 mo 1 ) CH and 16.8 g (0,10 mol) of hexamethylene diisocyanate at 80°C under N atmosphere.
The mixture was added dropwise within minutes, and the mixture was stirred as it was for 8 hours.
攪拌終了後、空気中でざらに６時間そのままの温度で攪
拌をして含フッ素ポリウレタンＩｋ得た。After the stirring was completed, the mixture was roughly stirred in air at the same temperature for 6 hours to obtain fluorine-containing polyurethane Ik.
ｍ、ｐ、１５℃℃
ＩＲ（ｎｅａｔ、ｃｍ−’）
３３３０．２９３０，２８６０，１７１０゜１５８０．
１３００〜１１５０
実施例２
機械攪拌装置、温度計、滴下Ｐ斗、還流器を備えた５０
０１／三ロフラスコに、
ＣＨ
を入れ、Ｎ、雰囲気下、６０℃で、滴下ｒ斗よりキシリ
レンジインシアネート２８．２ ｇ （０，１５ｍｏｌ
）、１３０分で滴下した。滴下終了後そのままの温度で
６時間攪拌して含フッ素テロマーを得た。m, p, 15°C IR (neat, cm-') 3330.2930,2860,1710°1580.
1300-1150 Example 2 50 equipped with a mechanical stirrer, thermometer, dropping port, and reflux device
28.2 g (0.15 mol
), was added dropwise over 130 minutes. After the dropwise addition was completed, the mixture was stirred at the same temperature for 6 hours to obtain a fluorine-containing telomer.
（発明の効果）
本発明は上記の構成をとることによって１次の効果を示
す。(Effects of the Invention) The present invention exhibits first-order effects by adopting the above configuration.
（１） ’４られた含フッ素ウレタン化合物は高めら
れた撥水性、撥油性、非粘着性を有する。(1) The fluorine-containing urethane compound has improved water repellency, oil repellency, and non-adhesiveness.
（２） この含フッ素ウレタン化合物よりなる樹脂は
向上した硬度、耐薬品性、耐熱性な有する。(2) The resin made of this fluorine-containing urethane compound has improved hardness, chemical resistance, and heat resistance.
特許出願人 三菱金属株式会社Patent applicant: Mitsubishi Metals Corporation
Claims (6)
ーテル結合を分子中に含有し、かつポリマーセグメント
当り、少なくとも１個のウレタン結合を有する含フッ素
ウレタン化合物、(1) A fluorine-containing urethane compound containing a perfluoroalkyl group having 4 to 10 carbon atoms and an ether bond in the molecule, and at least one urethane bond per polymer segment;
基、ｎは１または２の整数）で表される含フッ素ジオー
ルと、ジイソシアネートを反応させることを特徴とする
含フッ素ウレタン化合物の製造法、(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (1) (In the formula, R_f is a perfluoroalkyl group having 4 to 10 carbon atoms, and n is an integer of 1 or 2); A method for producing a fluorine-containing urethane compound, characterized by reacting a diisocyanate,
請求項第（１）項に記載の含フッ素ウレタン化合物、(3) The fluorine-containing urethane compound according to item (1), wherein the perfluoroalkyl group has 6 to 8 carbon atoms;
は室温から含フッ素ジオールおよびジイソシアネートの
沸点までの間である請求項第（２）項に記載の含フッ素
ウレタン化合物の製造法、(4) The method for producing a fluorine-containing urethane compound according to claim (2), wherein the reaction temperature of the fluorine-containing diol and the diisocyanate is between room temperature and the boiling point of the fluorine-containing diol and the diisocyanate;
は４０℃〜１２０℃である請求項第（２）項に記載の含
フッ素ウレタン化合物の製造法、(5) The method for producing a fluorine-containing urethane compound according to claim (2), wherein the reaction temperature of the fluorine-containing diol and the diisocyanate is 40°C to 120°C;
対して０．５〜１．５（モル比）の間である請求項第（
２）項に記載の含フッ素ウレタン化合物の製造法、(6) The amount of diisocyanate used is between 0.5 and 1.5 (mole ratio) relative to the fluorine-containing diol.
The method for producing a fluorine-containing urethane compound according to item 2),
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1081053A JP2699539B2 (en) | 1989-03-31 | 1989-03-31 | Method for producing fluorine-containing urethane compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1081053A JP2699539B2 (en) | 1989-03-31 | 1989-03-31 | Method for producing fluorine-containing urethane compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02258822A true JPH02258822A (en) | 1990-10-19 |
| JP2699539B2 JP2699539B2 (en) | 1998-01-19 |
Family
ID=13735672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1081053A Expired - Fee Related JP2699539B2 (en) | 1989-03-31 | 1989-03-31 | Method for producing fluorine-containing urethane compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2699539B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7258925B2 (en) | 2003-07-11 | 2007-08-21 | E.I. Du Pont De Nemours And Company | Fluorochemical finishes for paint applicators |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60149660A (en) * | 1976-04-06 | 1985-08-07 | チバ・ガイギー，アクチエンゲゼルシヤフト | Composition |
| JPS61252220A (en) * | 1985-04-30 | 1986-11-10 | Dainippon Ink & Chem Inc | Polyurethane resin |
| JPS63235319A (en) * | 1987-03-24 | 1988-09-30 | Achilles Corp | Production of polyurethane resin |
| JPH01242613A (en) * | 1988-03-23 | 1989-09-27 | Nippon Kayaku Co Ltd | Urethane (meth)acrylate mixture and resin composition and coating agent for optical fiber using this mixture |
-
1989
- 1989-03-31 JP JP1081053A patent/JP2699539B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60149660A (en) * | 1976-04-06 | 1985-08-07 | チバ・ガイギー，アクチエンゲゼルシヤフト | Composition |
| JPS61252220A (en) * | 1985-04-30 | 1986-11-10 | Dainippon Ink & Chem Inc | Polyurethane resin |
| JPS63235319A (en) * | 1987-03-24 | 1988-09-30 | Achilles Corp | Production of polyurethane resin |
| JPH01242613A (en) * | 1988-03-23 | 1989-09-27 | Nippon Kayaku Co Ltd | Urethane (meth)acrylate mixture and resin composition and coating agent for optical fiber using this mixture |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7258925B2 (en) | 2003-07-11 | 2007-08-21 | E.I. Du Pont De Nemours And Company | Fluorochemical finishes for paint applicators |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2699539B2 (en) | 1998-01-19 |
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| Date | Code | Title | Description |
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| LAPS | Cancellation because of no payment of annual fees |