JPH0730309B2 - Water and oil repellent - Google Patents
Water and oil repellentInfo
- Publication number
- JPH0730309B2 JPH0730309B2 JP61214898A JP21489886A JPH0730309B2 JP H0730309 B2 JPH0730309 B2 JP H0730309B2 JP 61214898 A JP61214898 A JP 61214898A JP 21489886 A JP21489886 A JP 21489886A JP H0730309 B2 JPH0730309 B2 JP H0730309B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- oil repellent
- product
- cotton
- oil
- 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
Description
【発明の詳細な説明】 産業上の利用分野 この発明は天然繊維、合成繊維などの繊維品や各種プラ
スチック成形品などに、撥水撥油性、耐水性、漏水性、
耐ドライソイル性などの防水性を付与する新規撥水撥油
剤に関し、特にカーペット、応接セット、カーテン、壁
紙、車両内装品などのインテリア製品に適用される撥水
撥油剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION Industrial Field of the Invention The present invention is applied to fiber products such as natural fibers and synthetic fibers, and various plastic molded products, for water and oil repellency, water resistance, water leakage,
The present invention relates to a novel water and oil repellent agent that imparts waterproofness such as dry soil resistance, and particularly to a water and oil repellent agent applied to interior products such as carpets, reception sets, curtains, wallpaper, and vehicle interior parts.
従来技術およびその問題点 従来、パーフルオロアルキル基をもつ重合体からなる撥
水撥油剤としては、パーフルオロアルキルアクリル酸エ
ステルまたは同メタクリル酸エステルを主成分とする共
重合体や、パーフルオロアルキル基が官能基を介して芳
香族環に結合した化合物からなるものが知られていた
（「染色工業」誌、第30巻、第９号、460〜466頁参
照）。そしてこれら撥水撥油剤は、通常、乳化剤で水分
散させたラテックス形態や、トリクロロエタンのような
有機溶剤に溶解させた溶解溶液形態で使用に供され、繊
維品の撥水撥油処理段階において、上記撥水撥油剤に樹
脂加工樹脂としてのメラミン樹脂およびその架橋剤を配
合し、必要に応じてさらに柔軟剤、帯電防止剤などを配
合し、配合物を含む処理液で繊維品をパッディング処理
し、乾燥後キュアリング処理を行なっていた。Conventional technology and its problems Conventionally, as a water- and oil-repellent agent composed of a polymer having a perfluoroalkyl group, a copolymer containing a perfluoroalkyl acrylic acid ester or a methacrylic acid ester as a main component or a perfluoroalkyl group is used. Was known to consist of a compound bound to an aromatic ring via a functional group (see "Dyeing Industry", Vol. 30, No. 9, pages 460-466). And these water and oil repellents are usually used in the form of a latex dispersed in water with an emulsifier, or in the form of a solution dissolved in an organic solvent such as trichloroethane. The water- and oil-repellent agent is mixed with a melamine resin as a resin processing resin and its cross-linking agent, and if necessary, a softening agent, an antistatic agent, etc. are further added, and a textile is padded with a treatment liquid containing the mixture. Then, a curing process was performed after drying.
しかし上記のような構造の化合物からなる撥水撥油剤を
用いてたとえば衣服に処理を施すと、特にポリエステル
製品の場合、衣服への撥水撥油剤の結合が十分でなく、
衣服の着用時の摩擦や伸縮、さらに洗濯やドライクリー
ニングなどの際に撥水撥油剤が衣服から脱落剥離して、
撥水撥油性能が徐々に低下していくきらいがあった。撥
水撥油剤の脱落剥離をなくして耐久性を保持するには、
上記加工用樹脂の配合量を増大すればよいのであるが、
この場合には、衣服に要求される生地の風合い、通気
性、柔軟性などが損なわれてしまううらみがあった。However, when a water- and oil-repellent agent comprising a compound having the above structure is used to treat clothes, for example, in the case of polyester products, the water- and oil-repellent agent is not sufficiently bonded to the clothes,
When the clothes are rubbed or stretched, the water- and oil-repellent agent comes off from the clothes when washing or dry cleaning.
There was a tendency for the water and oil repellency to gradually decline. To maintain the durability by eliminating the falling off of water and oil repellent,
It is only necessary to increase the amount of the processing resin blended,
In this case, there is a feeling that the texture, breathability, flexibility and the like of the fabric required for clothes are impaired.
この発明は上記のような実情に鑑みてなされたものであ
って、処理済みの繊維品からの撥水撥油剤の脱落剥離の
おそれが少なくて耐久性に優れ、かつ生地の風合い、通
気性、柔軟性などをそのまま保持した処理品を得ること
のできる撥水撥油剤を提供することを目的とする。The present invention has been made in view of the above circumstances, and is excellent in durability with less risk of falling off of the water and oil repellent from the treated textile, and the texture of the fabric, breathability, It is an object of the present invention to provide a water / oil repellent capable of obtaining a treated product which retains flexibility and the like.
問題点の解決手段 この発明による撥水撥油剤は、 一般式Rf−Ｘ−OH〔式中、Rfは炭素数４〜14の直鎖状ま
たは分枝状のパーフルオロアルキル基であり、Ｘはアル
キレン基であって、二重結合、エーテル結合、−SO2NR
−または−CONR−（Ｒは水素原子または低級アルキル基
である）を有していてもよい〕で示されるフルオロアル
コールを過剰の多価イソシアネートに付加させ、得られ
た付加体のイソシアネート残基に、両末端に水酸基を有
する数平均分子量1200〜3300のポリブタジエン・グリコ
ールまたはその水添物を反応させて得られた数平均分子
量1900〜8000の反応生成物よりなるものである。Solution to Problem The water and oil repellent according to the present invention has the general formula Rf-X-OH [wherein Rf is a linear or branched perfluoroalkyl group having 4 to 14 carbon atoms, and X is An alkylene group having a double bond, an ether bond, -SO 2 NR
-Or-CONR- (R may be a hydrogen atom or a lower alkyl group)] is added to the excess polyvalent isocyanate to give an isocyanate residue of the resulting adduct. And a reaction product having a number average molecular weight of 1900 to 8000 obtained by reacting a polybutadiene glycol having hydroxyl groups at both ends with a number average molecular weight of 1200 to 3300 or a hydrogenated product thereof.
ここで、多価イソシアネートの代表例としては、 で示されるイソホロンジイソシアネート（以下、IPDIと
略記する）、 で示されるイソホロンジイソシアネート三量体（以下、
IPDI−Ｔと略記する）、 で示されるイソホロンジイソシアネート・トリメチロー
ルプロパン付加体などが挙げられる。Here, as a representative example of the polyvalent isocyanate, Isophorone diisocyanate represented by (hereinafter abbreviated as IPDI), Isophorone diisocyanate trimer represented by (hereinafter,
Abbreviated as IPDI-T), The isophorone diisocyanate / trimethylolpropane adduct represented by
上記のようなイソホロン系の多価イソシアネートは、表
１に示すように、他の多価イソシアネートに比べて毒性
が少なくかつ蒸気圧が低いものであり、フルオロアルコ
ールとの反応後イソシアネート残基があっても取扱い容
易なものである。As shown in Table 1, the above isophorone-based polyisocyanate is less toxic and has a lower vapor pressure than other polyisocyanates, and has an isocyanate residue after reaction with fluoroalcohol. However, it is easy to handle.
フルオロアルコールのＸは、炭素数１〜10のアルキレン
基であって、二重結合、エーテル結合、−SO2NR−また
はCONR−（Ｒは水素原子または炭素数１〜12のアルキル
基である）を有していてもよい。フルオロアルコールの
代表例としては、 C7F15（CH2）2OH、 C7F15（CH2）3OH、 C12F25（CH2）3OH、 C8F17（CH2）3OH、 C3F7（CH2）3OH、 C7F15−CH＝CHCH2OH、 C8F17−CH＝CH（CH2）9OH、 C8F17（CH2）3O（CH2）2OH、 Rf−CH＝CHCH2O（CH2）2OH または C8F17SO2N（CH3）（CH2）2OH が挙げられる。 X of the fluoroalcohol is an alkylene group having 1 to 10 carbon atoms and is a double bond, an ether bond, -SO 2 NR- or CONR- (R is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms) May have. Typical examples of fluoroalcohol include C 7 F 15 (CH 2 ) 2 OH, C 7 F 15 (CH 2 ) 3 OH, C 12 F 25 (CH 2 ) 3 OH, C 8 F 17 (CH 2 ) 3 OH, C 3 F 7 (CH 2) 3 OH, C 7 F 15 -CH = CHCH 2 OH, C 8 F 17 -CH = CH (CH 2) 9 OH, C 8 F 17 (CH 2) 3 O ( CH 2) 2 OH, Rf- CH = CHCH 2 O (CH 2) 2 OH or C 8 F 17 SO 2 N ( CH 3) (CH 2) 2 OH and the like.
反応生成物の代表例としては、C8F17（CH2）3OHをIPDI
−Ｔに付加させ、イソシアネート残基に、分子量3000±
300、粘度（45℃）200〜350ポイズのポリブタジエン・
グリコールを反応させて得られた で示される数平均分子量約6200の反応生成物（以下FA・
IPDI−Ｔ・PBと略記する）、またはC8F17（CH2）3OHをI
PDIに付加させ、イソシアネート残基に、分子量3000±3
00粘度（45℃）200〜350ポイズのポリブタジエン・グリ
コールを反応させて得られた で示される数平均分子量約4300の反応生成物（以下、FA
・IPDI・PBと略記する）などが挙げられる。As a typical example of the reaction product, C 8 F 17 (CH 2 ) 3 OH is added to IPDI.
-T to add to the isocyanate residue, molecular weight 3000 ±
Polybutadiene with a viscosity of 300 and a viscosity (45 ° C) of 200 to 350 poise
Obtained by reacting glycol Reaction product with a number average molecular weight of about 6200 (hereinafter referred to as FA
IPDI-T ・ PB) or C 8 F 17 (CH 2 ) 3 OH
Addition to PDI to give an isocyanate residue with a molecular weight of 3000 ± 3
00 Viscosity (45 ℃) 200-350 Poise obtained by reacting polybutadiene glycol The reaction product having a number average molecular weight of about 4300 (hereinafter referred to as FA
・ Abbreviated as IPDI / PB).
また反応生成物は上記イソシアネート残基が未反応のま
ま残っているものであってもよく、ポリブタジエン・グ
リコールの一方の水酸基が未反応のまま残っているもの
であってもよい。The reaction product may be one in which the above-mentioned isocyanate residue remains unreacted, or one in which one hydroxyl group of polybutadiene glycol remains unreacted.
この発明による撥水撥油剤は、木綿、麻などのセルロー
ス系天然繊維、羊毛、絹などの動物系天然繊維、レーヨ
ン、アセテートなどの半合成繊維、ポリエステル、ポリ
アミド、ポリアクリロニトリル、ポリビニルアルコール
などの合成繊維よりなる繊維品や各種プラスチック成形
品およびフィルムに適用され、特にカーペット、応接セ
ット、カーテン、壁紙、車両内装品などのインテリアに
適用される。繊維品としてはポリエステル綿、ナイロン
綿、綿、レーヨンのような混紡品ないし交織品が適用さ
れる。The water- and oil-repellent agent according to the present invention includes synthetic natural fibers such as cotton, hemp and other cellulosic natural fibers, wool, silk and other animal natural fibers, rayon, acetate and other semi-synthetic fibers, polyester, polyamide, polyacrylonitrile, polyvinyl alcohol and the like. It is applied to textile products made of fibers and various plastic molded products and films, especially to interiors such as carpets, reception sets, curtains, wallpaper, and vehicle interior products. As the fiber product, a mixed-spun product or a mixed woven product such as polyester cotton, nylon cotton, cotton and rayon is applied.
発明の作用および効果 この発明による撥水撥油剤は、一般式Rf−Ｘ−OH〔式
中、Rfは炭素数４〜14の直鎖状または分枝状のパーフル
オロアルキル基であり、Ｘはアルキレン基であって、二
重結合、エーテル結合、−SO2NR−または−CONR−（Ｒ
は水素原子または低級アルキル基である）を有していて
もよい〕で示されるフルオロアルコールを過剰の多価イ
ソシアネートに付加させ、得られた付加体のイソシアネ
ート残基に、両末端に水酸基を有する数平均分子量1200
〜3300のポリブタジエン・グリコールまたはその水添物
を反応させて得られた数平均分子量1900〜8000の反応生
成物よりなるので、特定のポリブタジエン、グリコール
のすぐれた接着性を利用して、撥水撥油剤を繊維品に確
実堅固に付着させることができる。したがって、処理済
みの繊維品からの撥水撥油剤の脱落剥離のおそれがほと
んどなくなり、耐久性に優れた処理品を得ることができ
る。Action and Effect of the Invention The water and oil repellent according to the present invention has the general formula Rf—X—OH [wherein Rf is a linear or branched perfluoroalkyl group having 4 to 14 carbon atoms, and X is an alkylene group, a double bond, an ether bond, -SO 2 NR- or -CONR- (R
May be a hydrogen atom or a lower alkyl group)] is added to the excess polyvalent isocyanate, and the isocyanate residue of the resulting adduct has hydroxyl groups at both ends. Number average molecular weight 1200
~ 3300 polybutadiene glycol or its hydrogenated product is a reaction product with a number average molecular weight of 1900 ~ 8000. The oil agent can be firmly and firmly attached to the textile product. Therefore, there is almost no risk of the water- and oil-repellent agent falling off from the treated fiber product, and a treated product having excellent durability can be obtained.
またこの発明による撥水撥油剤は、上述のとおり繊維品
への付着性に優れているために、ごく少量の使用量で足
りる。したがって衣服に要求される生地の風合い、通気
性、柔軟性などを損うおそれが全くない。Further, since the water / oil repellent according to the present invention has excellent adhesiveness to a fiber product as described above, it is sufficient to use a very small amount. Therefore, there is no possibility of impairing the texture, breathability, flexibility, etc. of the fabric required for clothes.
実 施 例 つぎに、上記効果を実証するためにこの発明の実施例を
挙げ、また比較のために従来の撥水撥油剤を用いた比較
例を挙げる。Examples Next, examples of the present invention will be given to demonstrate the above effects, and comparative examples using a conventional water and oil repellent will be given for comparison.
実施例１ IPDI−T67g（0.1モル）をトリクロルエタン300gに溶か
して溶液（Ａ）を得た。容器内の空気を乾燥窒素で置換
し、溶液（Ａ）を温度70℃に昇温した。Example 1 67 g (0.1 mol) of IPDI-T was dissolved in 300 g of trichloroethane to obtain a solution (A). The air in the container was replaced with dry nitrogen, and the temperature of the solution (A) was raised to 70 ° C.
窒素気流中で93g（0.2モル）のフルオロアルコールC8F
17（CH2）3OHをトリクロルエタン300gに溶かし、溶液
（Ｂ）を得た。93 g (0.2 mol) of fluoroalcohol C 8 F in a nitrogen stream
17 (CH 2 ) 3 OH was dissolved in 300 g of trichloroethane to obtain a solution (B).
温度70℃の上記溶液（Ａ）にSn系触媒0.1gを加えて、溶
液（Ｂ）を攪拌下に１時間で滴下し、さらに上記温度で
30分間攪拌を続けた。To the above solution (A) at a temperature of 70 ° C, 0.1 g of Sn-based catalyst was added, and the solution (B) was added dropwise under stirring for 1 hour.
Stirring was continued for 30 minutes.
反応溶液にさらに市販のポリブタジエン・グリコール
（日本曹達社製、商品名G3000、分子量2890）144g（0.0
5モル）を添加した。In the reaction solution, further commercially available polybutadiene glycol (Nippon Soda Co., Ltd., trade name G3000, molecular weight 2890) 144 g (0.0
5 mol) was added.
こうして反応生成物FA・IPDI−Ｔ・PBを得た。ついでこ
の反応溶液にトリクロルエタン400gを加え、固形分30.5
％含む撥水撥油剤を得た。Thus, the reaction product FA.IPDI-T.PB was obtained. Then, 400 g of trichloroethane was added to this reaction solution to give a solid content of 30.5.
% Water and oil repellent was obtained.
上記撥水撥油剤をトリクロルエタンで薄めて固形分濃度
0.18％のパッド浴を調製した。このパッド浴を用いて、
木綿の試験用クロス片をピックアップ率85％でパッディ
ング処理し、処理品を100℃で２分間乾燥し、さらに150
℃で３分間熱処理した。Dilute the water and oil repellent with trichloroethane to obtain a solid content
A 0.18% pad bath was prepared. With this pad bath,
A piece of cotton test cloth is padded with a pickup rate of 85%, and the treated product is dried at 100 ° C for 2 minutes.
It heat-processed at 3 degreeC for 3 minutes.
またIPDI−ＴとフルオロアルコールC8F17（CH2）3OHとG
3000とを等モルずつ用いて、上記と同じ操作を行なうこ
とにより、IPDI−Ｔの１つのイソシアネート基がフルオ
ロアルコールと反応し、残る２つのイソシアネート基が
G3000と反応した反応生成物が得られた。IPDI-T and fluoroalcohol C 8 F 17 (CH 2 ) 3 OH and G
By carrying out the same operation as above using 3000 and equimolar amounts, one isocyanate group of IPDI-T reacts with fluoroalcohol, and the remaining two isocyanate groups become
A reaction product was obtained which reacted with G3000.
実施例２ IPDI−Ｔの変わりにトリクロルエタン200g中のIPDI 22
g（0.1モル）を用い、フルオロアルコールとしてトリク
ロルエタン200g中のC8F17（CH2）3OH46g（0.1モル）を
用い、G3000を実施例１と同じく145g（0.05モル）を用
いて、実施例１と同じ操作を行なった。Example 2 IPDI 22 in 200 g of trichloroethane instead of IPDI-T
g (0.1 mol), C 8 F 17 (CH 2 ) 3 OH 46 g (0.1 mol) in 200 g of trichloroethane as fluoroalcohol, and G3000 using 145 g (0.05 mol) as in Example 1. The same operation as in Example 1 was performed.
こうして反応生成物FA・IPDI・PBを得た。ついでこの反
応溶液にトリクロルエタン600gを加え、固形分21.3％を
含む撥水撥油剤を得た。Thus, the reaction products FA / IPDI / PB were obtained. Then, 600 g of trichloroethane was added to this reaction solution to obtain a water and oil repellent containing solids of 21.3%.
この撥水撥油剤を用いて実施例１と同じ手法でクロス片
をパッディング処理した。Using this water and oil repellent agent, the cloth pieces were padded in the same manner as in Example 1.
比較例１ 撥水撥油剤として直鎖状パーフルオロアルキルアクリル
酸エステルを主成分とする共重合体のラテックス（商品
名「旭ガードAG710」旭硝子社製）を用い、上記と同じ
試験用クロス片に同じ条件で処理を施した。Comparative Example 1 A latex of a copolymer containing a linear perfluoroalkyl acrylate as a main component (trade name "Asahi Guard AG710" manufactured by Asahi Glass Co., Ltd.) was used as a water and oil repellent, and the same test cloth piece was used as above. The treatment was performed under the same conditions.
撥水性試験 実施例１および２ならびに比較例１で得た各処理クロス
片の処理直後のもの、および処理試験片を家庭用洗濯機
で、洗剤1.7g/で40℃で10分間処理し、風乾後140℃で
アイロンがけしたものについて、それぞれJIS Ｌ−109
2に規定されたスプレー法により、表面の水付着程度か
ら撥水性の評価を行なった。評価基準は表２に示す通り
である。評価結果を表４に示す。Water repellency test Immediately after the treatment of the treated cloth pieces obtained in Examples 1 and 2 and Comparative Example 1 and the treated test pieces were treated with a household washing machine with 1.7 g / detergent at 40 ° C. for 10 minutes and air dried. JIS L-109 for items that were subsequently ironed at 140 ° C
The water repellency was evaluated from the degree of water adhesion on the surface by the spray method specified in 2. The evaluation criteria are as shown in Table 2. The evaluation results are shown in Table 4.
撥油性試験 実施例１および２ならびに比較例１で得た各処理クロス
片上にｎ−ヘプタンとヌジョールの混合物をそれぞれ滴
下した。そして液滴がクロス片に３分間以上浸透しない
場合の撥油性値を表４に示す。また上記混合物の組成と
撥油性値の関係を表３に示す。Oil repellency test A mixture of n-heptane and nujol was dropped on each of the treated cloth pieces obtained in Examples 1 and 2 and Comparative Example 1. Table 4 shows the oil repellency values when the droplets do not penetrate into the cloth piece for 3 minutes or more. Table 3 shows the relationship between the composition of the mixture and the oil repellency value.
表４から明らかなように、実施例１および２の撥水撥油
剤による処理クロス片は、比較例１の撥水撥油剤による
ものに比べて、家庭での洗濯後も撥水撥油性を保持し、
耐久性に優れていることがわかる。 As is clear from Table 4, the treated cloth pieces of the water and oil repellents of Examples 1 and 2 retain the water and oil repellency even after washing at home, as compared with the water repellent agent of Comparative Example 1. Then
It can be seen that it has excellent durability.
Claims (5)
14の直鎖状または分枝状のパーフルオロアルキル基であ
り、Ｘはアルキレン基であって、二重結合、エーテル結
合、−SO2NR−または−CONR−（Ｒは水素原子または低
級アルキル基である）を有していてもよい〕で示される
フルオロアルコールを過剰の多価イソシアネートに付加
させ、得られた付加体のイソシアネート残基に、両末端
に水酸基を有する数平均分子量1200〜3300のポリブタジ
エン・グリコールまたはその水添物を反応させて得られ
た数平均分子量1900〜8000の反応生成物よりなる撥水撥
油剤。1. A general formula Rf-X-OH [wherein Rf has 4 to 4 carbon atoms].
14 is a linear or branched perfluoroalkyl group, X is an alkylene group, and is a double bond, an ether bond, —SO 2 NR— or —CONR— (R is a hydrogen atom or a lower alkyl group. It may have)] is added to a polyhydric isocyanate in excess of a fluoroalcohol, and the isocyanate residue of the resulting adduct has a number average molecular weight of 1,200 to 3,300 having hydroxyl groups at both ends. A water and oil repellent agent comprising a reaction product having a number average molecular weight of 1,900 to 8,000, obtained by reacting polybutadiene glycol or a hydrogenated product thereof.
アネート、イソホロンジイソシアネート三量体、イソホ
ロンジイソシアネート・トリメチロールプロパン付加体
などの脂環式多価イソシアネートである特許請求の範囲
第１項記載の撥水撥油剤。2. The water and oil repellent according to claim 1, wherein the polyvalent isocyanate is an alicyclic polyvalent isocyanate such as isophorone diisocyanate, isophorone diisocyanate trimer, and isophorone diisocyanate / trimethylolpropane adduct.
剤。3. A fluoroalcohol is C 7 F 15 (CH 2 ) 2 OH, C 7 F 15 (CH 2 ) 3 OH, C 12 F 25 (CH 2 ) 3 OH, C 8 F 17 (CH 2 ) 3 OH, C 3 F 7 (CH 2) 3 OH, C 7 F 15 -CH = CHCH 2 OH, C 8 F 17 -CH = CH (CH 2) 9 OH, C 8 F 17 (CH 2) 3 O ( CH 2 ) 2 OH, Rf-CH = CHCH 2 O (CH 2 ) 2 OH or C 8 F 17 SO 2 N (CH 3 ) (CH 2 ) 2 OH. Water and oil repellent.
毛、絹などの動物系天然繊維、レーヨン、アセテートな
どの半合成繊維、ポリエステル、ポリアミド、ポリアク
リロニトリル、ポリビニルアルコールなどの合成繊維よ
りなる繊維品や各種プラスチック成形品およびフィルム
に適用される特許請求の範囲第１〜３項のうちいずれか
１項記載の撥水撥油剤。4. Fibers made of cellulosic natural fibers such as cotton and hemp, animal natural fibers such as wool and silk, semi-synthetic fibers such as rayon and acetate, synthetic fibers such as polyester, polyamide, polyacrylonitrile and polyvinyl alcohol. The water / oil repellent according to any one of claims 1 to 3, which is applied to products, various plastic molded products and films.
レーヨンのような混紡品ないし交織品である特許請求の
範囲第４項記載の撥水撥油剤。5. The water and oil repellent according to claim 4, wherein the fiber product is a blended product or a mixed woven product such as polyester cotton, nylon cotton and cotton rayon.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61214898A JPH0730309B2 (en) | 1986-09-10 | 1986-09-10 | Water and oil repellent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61214898A JPH0730309B2 (en) | 1986-09-10 | 1986-09-10 | Water and oil repellent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6368685A JPS6368685A (en) | 1988-03-28 |
| JPH0730309B2 true JPH0730309B2 (en) | 1995-04-05 |
Family
ID=16663387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61214898A Expired - Lifetime JPH0730309B2 (en) | 1986-09-10 | 1986-09-10 | Water and oil repellent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0730309B2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2672593C (en) * | 2006-12-14 | 2016-09-20 | Interface Biologics Inc. | Surface modifying macromolecules with high degradation temperatures and uses thereof |
| US8563115B2 (en) * | 2008-08-12 | 2013-10-22 | Xerox Corporation | Protective coatings for solid inkjet applications |
| DK2295132T3 (en) | 2009-05-15 | 2016-12-05 | Interface Biologics Inc | Antithrombogenic hollow-fiber membranes, molding material and blood long |
| JP6691699B2 (en) * | 2015-03-23 | 2020-05-13 | 東レコーテックス株式会社 | Method for manufacturing waterproof fabric |
| CN110167995B (en) | 2016-10-18 | 2022-07-01 | 界面生物公司 | Plasticized PVC compounds having surface-modified macromolecules and articles made therefrom |
| WO2019014400A1 (en) | 2017-07-14 | 2019-01-17 | Fresenius Medical Care Holdings, Inc. | Method for providing surface modifying composition with improved byproduct removal |
| JP6726383B2 (en) * | 2019-04-04 | 2020-07-22 | 東レコーテックス株式会社 | Waterproof fabric |
-
1986
- 1986-09-10 JP JP61214898A patent/JPH0730309B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6368685A (en) | 1988-03-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5112930A (en) | Modified polyurethanes containing perfluoroaliphatic groups and use thereof | |
| US3716518A (en) | Siloxane polymers for soil-repellent and soil-release textile finishes | |
| EP0713863B1 (en) | Carbodiimide compound and durable water repellent compositions containing said compound | |
| EP1217119B1 (en) | Water-soluble, water/oil repellent treating composition and method of making | |
| KR100214321B1 (en) | Composition for providing oil and water repellency | |
| JP6435320B2 (en) | Urethane polymer extenders for compositions that modify the surface properties of substrates | |
| KR920009256B1 (en) | Method for obtaining a coating for wash-and cleaning-resistant textiles comprised of reactive perfluoroalkyl rest-containing () polymers and/or precondensates | |
| EP0218909B1 (en) | High performance water and oil repellant | |
| JP2005527674A (en) | Fluorochemical composition for treating fiber substrates | |
| WO2004070105A1 (en) | Fluorochemical urethane composition for treatment of fibrous substrates | |
| JPH0529706B2 (en) | ||
| JPH11279527A (en) | Antifouling treating agent composition, production thereof, and article treated therewith | |
| JPH04211489A (en) | Orgaic polyfluoro-nitrogenous compound | |
| JPH0610271A (en) | Composition and method for finishing woven fabric | |
| JPH0730309B2 (en) | Water and oil repellent | |
| KR20190112320A (en) | Polymers for Hydrophobic and Oleophobic Textile Finishes | |
| US3716517A (en) | Siloxane polymers for soil-repellent and soil-release textile finishes | |
| KR100537881B1 (en) | Fluorochemical composition comprising a blocked isocyanate extender and method of treatment of a fibrous substrate therewith | |
| JP3276958B2 (en) | Fluorocarbamate antifouling agent | |
| JPH08510489A (en) | Aqueous polymer dispersions and their use for the production of water vapor permeable coatings | |
| KR20110022603A (en) | Fluoropolymer compositions and treated substrates | |
| JPH09324173A (en) | Composition for soil resistant processing and the same processing | |
| JPS6216454A (en) | Blocked polyisocyanate compound, water and oil-repellent agent and treatment therewith | |
| EP1414882A1 (en) | Compositions of polysiloxanes, fluoropolymers and extenders | |
| US3462295A (en) | Process for rendering cellulosic and fibrous materials oil - water - repellent and product therefrom |