JPH0426328B2 - - Google Patents
Info
- Publication number
- JPH0426328B2 JPH0426328B2 JP60093376A JP9337685A JPH0426328B2 JP H0426328 B2 JPH0426328 B2 JP H0426328B2 JP 60093376 A JP60093376 A JP 60093376A JP 9337685 A JP9337685 A JP 9337685A JP H0426328 B2 JPH0426328 B2 JP H0426328B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- urethane resin
- fluorine
- 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.)
- Expired - Lifetime
Links
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 32
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- -1 diisocyanate compound Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000002605 large molecules Chemical class 0.000 claims description 2
- 150000003384 small molecules Chemical class 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 8
- 150000003673 urethanes Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 150000004812 organic fluorine compounds Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical group FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Description
〔産業上の利用分野〕
本発明は特定の機能性基を分子側鎖に含有する
ウレタン樹脂の製造方法に関するものであり、更
に詳しくは分子側鎖にパーフロロアルキル基を含
有することを特徴とする新規なウレタン樹脂の製
造方法に関するものである。
本発明の製造方法で得られたウレタン樹脂の産
業上の利用分野は、特に限定されるものではない
が、基材表面の被覆、繊維状物質の結合結接など
のバインダー、粉状物質の分散固着などのバイン
ダーおよび単体のフイルム、シート、その他の成
型品などの分野において物理的、化学的、電気
的、生物化学的諸性質の改善などを必要とする場
合に特に有効に使用されうるものである。
〔従来の技術〕
一般にウレタン樹脂は強靭性、耐寒性、耐熱
性、耐薬品性および各種基材への密着性などに優
れ、かつ各種加工法への適性にも優れるため各種
基材の表面被覆剤、接着剤、結合剤、結接剤及び
フイルム、シートその他の成型材料として巾広い
分野で使用されている。これらのウレタン樹脂の
優れた特徴は主として分子内に存在するウレタン
結合及びその類縁であるウレア結合の高い極性に
基づく強い分子内、分子間凝集力に発現されてい
るものである。
一方有機フツ素化合物はＣ−Ｆ結合の極性の低
さ、凝集力の低さのために表面エネルギーを著し
く低下させる特徴があり、これが撥水、撥油、減
摩、非粘着、防汚などの機能を発現し各種の分野
で使用されている。
最近ウレタン樹脂に有機フツ素化合物の有する
特性を付与し、ウレタン樹脂の性能並びに機能性
を飛躍的に向上する方法が提案されている。例え
ばポリイソシアネート化合物とパーフロロアルキ
ルアルコールとのアダクト体で分子末端にフロロ
カーボン基を有するフツ素変性ウレタンオリゴマ
ーをウレタン樹脂に添加して改質する方法或いは
又有機ジイソシアネート化合物とパーフロロアル
キル基を含有するグリコールとの反応で分子主鎖
中にフルオロカーボン基を有するフツ素変性ウレ
タン樹脂による改質方法などがある。
〔本発明が解決しようとする問題点〕
しかしこのようなフツ素変性ウレタン樹脂はウ
レタン樹脂の有する強靭性などの機能と本来有す
るフロロカーボン鎖に基づく表面エネルギー低下
等の機能を充分には満足し得ないものでありその
ため用途、分野を著しく制約される欠点がある。
例えば前者のフツ素変性ウレタンオリゴマーに
おいては分子末端にフロロカーボン鎖を有するた
め、それに基づく機能を発現し易いが、比較的低
分子量のためそれ自体ではウレタン樹脂に基づく
機能はなくウレタン樹脂に添加することによつて
始めて両者の機能が発現される。しかしこれもフ
ツ素変性オリゴマー自体低分子量のため経時的に
ブリードするとともに、水、溶剤などにより抽出
されるため、フロロカーボン鎖に基づく機能が経
時的に消失するという致命的欠陥を有するもので
ある。
一方後者のフツ素変性ウレタン樹脂は前者の様
な欠点はないが分子主鎖中にフロロカーボン基が
固定されるため本来有するフロロカーボン基に基
づく機能の発現の有効性に乏しく、機能を発現さ
せるためにはその含有量を必要以上に高めざるを
得ないという欠点がある。
しかしながら、パーフロロアルキル基含有量を
必要以上に高めると、分子全体として凝集力が低
下し、新たにウレタン樹脂の本来有する機能の発
現を阻害するという問題点が発生する。即ちこの
様なフツ素変性ウレタン樹脂ではウレタン樹脂の
本来有する機能を保持させてこれにパーフロロカ
ーボン鎖のもつ表面エネルギーの低下などの諸特
性を相乗させる目的の解決にはなり得ない状況に
ある。
発明の構成
〔問題点を解決するための手段〕
本発明者らはウレタン樹脂の変性技術を駆使し
鋭意検討の結果特定のパーフロロアルキル基含有
化合物を使用することにより、ウレタン樹脂の本
来有する機能とフロロカーボン鎖の本来有する機
能とを兼備するウレタン樹脂を見い出すに到つ
た。
以下本発明について説明する。
〔作用〕
本発明は分子中にパーフロロアルキル基を含有
するウレタン樹脂に関するものであり、特に重要
なのはパーフロロアルキル基が分子側鎖に櫛状に
導入されるウレタン樹脂と定義されるものであ
る。
本発明の分子側鎖にパーフロロアルキル基を含
有するウレタン樹脂の分子構造は、次のものが好
ましい。
後記式〔〕使用
後記式〔〕使用
Ａは活性水素含有高分子量化合物の活性水素以
外の部分、Ｂは活性水素含有低分子量化合物の活
性水素以外の部分、Ｈは水素、〓〓は有機ジイソ
シアネート化合物、Z1、Z2は２〜450の整数、l1、
l2は１〜85の整数、m1、m2は１〜50の整数、n1、
n2は０〜90の整数を示す。X1、X2、Y1、Y2、Rf
は後記のとおりである。
さらに式〔〕及び／又は式〔〕で表わされ
る化合物を反応して櫛状に含むことを特徴とする
パーフロロアルキル基含有ウレタン樹脂である。
式〔〕：
式〔〕：
〔式〔〕中、Rfは炭素数３〜18のパーフロロ
アルキル基又はパーフロロアルケニル基であり、
Y1は３価の連結基で−CON、−SO2N、−（
CH2CH2）−iCON、（CH2CH2）iSO2N、（但し
ｉは１〜４の整数）、
[Industrial Application Field] The present invention relates to a method for producing a urethane resin containing a specific functional group in its molecular side chain, and more specifically, a method for producing a urethane resin containing a perfluoroalkyl group in its molecular side chain. The present invention relates to a method for producing a new urethane resin. The industrial fields of application of the urethane resin obtained by the production method of the present invention are not particularly limited, but include coating the surface of a base material, binding and binding of fibrous materials, etc., and dispersion of powdery materials. It can be used particularly effectively in the fields of binders such as fixing, single films, sheets, and other molded products, where improvements in physical, chemical, electrical, and biochemical properties are required. be. [Prior art] In general, urethane resins have excellent toughness, cold resistance, heat resistance, chemical resistance, and adhesion to various substrates, and are also suitable for various processing methods, so they are suitable for surface coating of various substrates. It is used in a wide range of fields as agents, adhesives, binders, binders, and molding materials for films, sheets, and other products. The excellent characteristics of these urethane resins are mainly expressed in the strong intra- and intermolecular cohesive force based on the high polarity of the urethane bonds present in the molecules and the urea bonds that are related thereto. On the other hand, organic fluorine compounds have the characteristic of significantly lowering the surface energy due to the low polarity of C-F bonds and low cohesive force, and this is effective for water repellency, oil repellency, anti-friction, non-adhesion, antifouling, etc. It has the following functions and is used in various fields. Recently, a method has been proposed to dramatically improve the performance and functionality of urethane resins by imparting the properties of organic fluorine compounds to urethane resins. For example, a method in which a fluorine-modified urethane oligomer, which is an adduct of a polyisocyanate compound and a perfluoroalkyl alcohol and has a fluorocarbon group at the molecular end, is added to a urethane resin to modify the resin, or a method in which a urethane resin is modified by adding an adduct of a polyisocyanate compound and a perfluoroalkyl alcohol, or a method in which a urethane resin is modified by adding an adduct of a polyisocyanate compound and a perfluoroalkyl alcohol to a urethane resin; There is a modification method using a fluorine-modified urethane resin that has a fluorocarbon group in its molecular main chain through reaction with glycol. [Problems to be solved by the present invention] However, such fluorine-modified urethane resins cannot fully satisfy the functions of urethane resins such as toughness and the functions of surface energy reduction based on the inherent fluorocarbon chains. Therefore, it has the drawback that its applications and fields are severely restricted. For example, the former fluorine-modified urethane oligomer has a fluorocarbon chain at the end of the molecule, so it is easy to exhibit functions based on it, but because of its relatively low molecular weight, it does not have functions based on urethane resins by itself and can be added to urethane resins. Both functions are realized only by However, since the fluorine-modified oligomer itself has a low molecular weight, it bleeds over time and is extracted with water, solvents, etc., so it has a fatal flaw in that the function based on the fluorocarbon chain disappears over time. On the other hand, the latter type of fluorine-modified urethane resin does not have the disadvantages of the former, but because the fluorocarbon group is fixed in the main chain of the molecule, it is less effective in expressing the function based on the original fluorocarbon group, and it is difficult to express the function. has the disadvantage that its content must be increased more than necessary. However, if the perfluoroalkyl group content is increased more than necessary, the cohesive force of the molecule as a whole decreases, and a new problem arises in that the expression of the original functions of the urethane resin is inhibited. In other words, such fluorine-modified urethane resins cannot be used to solve the problem of retaining the original functions of urethane resins and synergizing them with various properties such as a reduction in surface energy of perfluorocarbon chains. Structure of the Invention [Means for Solving the Problems] The present inventors made full use of urethane resin modification technology, and as a result of intensive studies, by using a specific perfluoroalkyl group-containing compound, the inherent functions of urethane resins were solved. We have now discovered a urethane resin that has both the functions inherent to fluorocarbon chains. The present invention will be explained below. [Function] The present invention relates to urethane resins containing perfluoroalkyl groups in the molecule, and particularly important are those defined as urethane resins in which perfluoroalkyl groups are introduced into the side chains of the molecules in a comb-like manner. . The molecular structure of the urethane resin containing a perfluoroalkyl group in the molecular side chain of the present invention is preferably as follows. Use of the following formula [] Use of the following formula [] A is a moiety other than active hydrogen of a high molecular weight compound containing active hydrogen, B is a moiety other than active hydrogen of a low molecular weight compound containing active hydrogen, H is hydrogen, 〓〓 is an organic diisocyanate compound, Z 1 and Z 2 are 2 to 450 an integer of l 1 ,
l2 is an integer from 1 to 85, m1 , m2 is an integer from 1 to 50, n1 ,
n2 represents an integer from 0 to 90. X 1 , X 2 , Y 1 , Y 2 , Rf
is as described below. Furthermore, it is a perfluoroalkyl group-containing urethane resin characterized by containing a compound represented by the formula [] and/or the formula [] in a comb-like form. formula〔〕: formula〔〕: [Formula [], Rf is a perfluoroalkyl group or a perfluoroalkenyl group having 3 to 18 carbon atoms,
Y 1 is a trivalent linking group -CON, -SO 2 N, -(
CH 2 CH 2 ) − i CON, (CH 2 CH 2 ) i SO 2 N, (where i is an integer from 1 to 4),
【式】【formula】
【式】【formula】
【式】（但しR1はＨ又炭素数１〜
３のアルキル基）、
−（CH2CH2）−iＮ（但しｉは前記の通り）、−
CH2CH2CH2N、[Formula] (wherein R 1 is H or an alkyl group having 1 to 3 carbon atoms), -(CH 2 CH 2 ) - i N (however, i is as above), -
CH 2 CH 2 CH 2 N,
【式】−
CH2CH2SCH2CH2N又は、−
CH2CH2SCH2CH2CONであり、Q1、Q2は２価
の連結基で−（CH2）−j（但しｊは２〜６の整数）
又は[Formula] − CH 2 CH 2 SCH 2 CH 2 N or −
CH 2 CH 2 SCH 2 CH 2 CON, Q 1 and Q 2 are divalent linking groups -(CH 2 )- j (where j is an integer from 2 to 6)
or
【式】（但しR1は前記の通
り）であり、X1、X2は−Ｏ−、−Ｓ−、又は
[Formula] (where R 1 is as above), and X 1 and X 2 are -O-, -S-, or
【式】（R2はＨ又は炭素数１〜６のアルキル
基）である。
式〔〕中、Rf、X1は前記の通りであり、Y2
は２価の連結基で、[Formula] (R 2 is H or an alkyl group having 1 to 6 carbon atoms). In the formula [], Rf and X 1 are as described above, and Y 2
is a divalent linking group,
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】（但し、ｉ、R2
は前記の通り）、−CH2CH2−Ｏ−、−CH2CH2S−
又は−CH2CH2SCH2CH2−Ｏ−であり、ａは０
又は１である。
なお、Rfはパーフロロアルキル基又はパーフ
ロロアルケニル基であるが、これらは直鎖状又は
[Formula] (where i and R 2 are as above), -CH 2 CH 2 -O-, -CH 2 CH 2 S-
or -CH 2 CH 2 SCH 2 CH 2 -O-, where a is 0
Or 1. In addition, Rf is a perfluoroalkyl group or a perfluoroalkenyl group, but these are linear or
【式】の如き分岐状、又はBranched like [formula], or
【式】の如き環状又はそれ
らを組合せたいずれのものでも良く、さらに
It may be ring-shaped as in [Formula] or a combination thereof, and further
５級：異常なく剥離できる。
４級：少し融着している。
３級：かなり融着している。
〜
１級：剥離不可能（材質破壊である。）
(*5) 配合液の顔料分散性
ウレタン樹脂の溶液に固型分当り顔料
（DILACWT2301：大日本インキ化学工業製）
を50％添加し、着色溶液を調整する。これを脱
泡後直ちにポリエステルフイルム上0.1mmの厚
さで塗布、100℃２分熱風乾燥する。そして皮
膜の発色性色ムラ現象を目視で判定する。
また着色溶液を２日間静止し、前記と同様に
着色皮膜を作成し、発色性、色ムラ現象を目視
で判定する。
判定基準：
○色ムラ現象なし
△少し色ムラ現象あり
×色ムラ現象あり
Grade 5: Can be peeled off without any abnormality. Grade 4: Slightly fused. Grade 3: Considerably fused. ~ Grade 1: Impossible to peel (material destruction) (*5) Pigment dispersibility of compounded liquid Pigment per solid content in urethane resin solution (DILACWT2301: manufactured by Dainippon Ink & Chemicals)
Add 50% of the solution to prepare the coloring solution. Immediately after defoaming, apply this to a thickness of 0.1 mm on a polyester film and dry with hot air at 100°C for 2 minutes. Then, the chromogenic color unevenness phenomenon of the film is visually determined. Further, the colored solution was allowed to stand still for two days, a colored film was prepared in the same manner as above, and the coloring property and color unevenness phenomenon were visually judged. Judgment criteria: ○No color unevenness phenomenon △Slight color unevenness phenomenon ×Color unevenness phenomenon observed
【表】【table】
【表】【table】
【表】【table】
Claims (1)
活性水素を含有する含フツ素化合物と、有機ジイ
ソシアネート化合物と、フツ素を含有しない活性
水素含有低分子量化合物及び／又はフツ素を含有
しない活性水素含有高分子量化合物とを反応させ
るウレタン樹脂の製造方法において、該含フツ素
化合物として、分子内に１つのパーフロロアルキ
ル基と２個以上の活性水素を含有する含フツ素化
合物を用いることを特徴とするウレタン樹脂の製
造方法。1. A fluorine-containing compound containing a perfluoroalkyl group and two or more active hydrogens in the molecule, an organic diisocyanate compound, and a low molecular weight compound containing active hydrogen that does not contain fluorine and/or an active hydrogen that does not contain fluorine. A method for producing a urethane resin in which a urethane resin is reacted with a containing high molecular weight compound, characterized in that a fluorine-containing compound containing one perfluoroalkyl group and two or more active hydrogens in the molecule is used as the fluorine-containing compound. A method for producing urethane resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60093376A JPS61252220A (en) | 1985-04-30 | 1985-04-30 | Polyurethane resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60093376A JPS61252220A (en) | 1985-04-30 | 1985-04-30 | Polyurethane resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61252220A JPS61252220A (en) | 1986-11-10 |
| JPH0426328B2 true JPH0426328B2 (en) | 1992-05-07 |
Family
ID=14080582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60093376A Granted JPS61252220A (en) | 1985-04-30 | 1985-04-30 | Polyurethane resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61252220A (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63202611A (en) * | 1987-02-17 | 1988-08-22 | Sanyo Chem Ind Ltd | Curable composition |
| JP2643248B2 (en) * | 1987-03-20 | 1997-08-20 | 旭硝子株式会社 | Method for producing polymer |
| US4841007A (en) * | 1988-03-28 | 1989-06-20 | Becton Dickinson And Company | Fluorinated polyetherurethanes and medical devices therefrom |
| JP2699539B2 (en) * | 1989-03-31 | 1998-01-19 | 三菱マテリアル株式会社 | Method for producing fluorine-containing urethane compound |
| JP2699538B2 (en) * | 1989-03-31 | 1998-01-19 | 三菱マテリアル株式会社 | Method for producing fluorine-containing urethane compound |
| US5539008A (en) * | 1993-12-29 | 1996-07-23 | Minnesota Mining And Manufacturing Company | Foamable composition containing unsaturated perfluorochemical blowing agent |
| WO1996037540A1 (en) * | 1995-05-23 | 1996-11-28 | Minnesota Mining And Manufacturing Company | Foamable composition containing unsaturated perfluorochemical blowing agent |
| KR20010017938A (en) * | 1999-08-16 | 2001-03-05 | 최윤소 | Polyurethane compound which has good water and oil repellent properties |
| NL1013001C2 (en) * | 1999-09-08 | 2001-03-12 | Dsm Nv | Fluorinated polycondensation polymer used for diaphragms, tubing, sealing rings and tapes has the fluorine mainly in side groups |
| TW518319B (en) * | 2000-03-07 | 2003-01-21 | Dainichiseika Color & Amp Chem | Fluorine-containing diols and use thereof |
| DE10331483A1 (en) * | 2003-07-11 | 2005-02-10 | Construction Research & Technology Gmbh | Fluoromodified one- or two-component polyurethane resins, process for their preparation and their use |
| US7279210B2 (en) * | 2005-09-07 | 2007-10-09 | 3M Innovative Properties Company | Curable compositions, methods of making and using the same, and articles therefrom |
| JP5846118B2 (en) * | 2010-06-04 | 2016-01-20 | 旭硝子株式会社 | Water / oil repellent and water / oil repellent composition |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4843096A (en) * | 1971-09-27 | 1973-06-22 | ||
| US3759874A (en) * | 1971-08-30 | 1973-09-18 | Fmc Corp | Fluorinated polyurethanes as soil release agents |
| JPS50114497A (en) * | 1974-02-04 | 1975-09-08 | ||
| JPS5285105A (en) * | 1976-01-05 | 1977-07-15 | Ciba Geigy Ag | Perfluoroalkyl group substituted acid unhydride polybasic acid and their derivatives and preparation method and application thereof |
| JPS5834866A (en) * | 1981-08-27 | 1983-03-01 | Dainippon Ink & Chem Inc | Composition for urethane coating |
| JPS59136302A (en) * | 1983-01-03 | 1984-08-04 | チバ−ガイギ−・アクチエンゲゼルシヤフト | Perfluoroalkyl substituted polymer |
| JPS59226015A (en) * | 1983-05-27 | 1984-12-19 | バイエル・アクチエンゲゼルシヤフト | Perfluoroalkyl group-containing polyurethane and manufacture |
-
1985
- 1985-04-30 JP JP60093376A patent/JPS61252220A/en active Granted
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3759874A (en) * | 1971-08-30 | 1973-09-18 | Fmc Corp | Fluorinated polyurethanes as soil release agents |
| JPS4843096A (en) * | 1971-09-27 | 1973-06-22 | ||
| JPS50114497A (en) * | 1974-02-04 | 1975-09-08 | ||
| JPS5285105A (en) * | 1976-01-05 | 1977-07-15 | Ciba Geigy Ag | Perfluoroalkyl group substituted acid unhydride polybasic acid and their derivatives and preparation method and application thereof |
| JPS5834866A (en) * | 1981-08-27 | 1983-03-01 | Dainippon Ink & Chem Inc | Composition for urethane coating |
| JPS59136302A (en) * | 1983-01-03 | 1984-08-04 | チバ−ガイギ−・アクチエンゲゼルシヤフト | Perfluoroalkyl substituted polymer |
| JPS59226015A (en) * | 1983-05-27 | 1984-12-19 | バイエル・アクチエンゲゼルシヤフト | Perfluoroalkyl group-containing polyurethane and manufacture |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61252220A (en) | 1986-11-10 |
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