JPS5951907A - Imparting hydrophilicity to surface of polymeric substance - Google Patents

Imparting hydrophilicity to surface of polymeric substance

Info

Publication number
JPS5951907A
JPS5951907A JP16263882A JP16263882A JPS5951907A JP S5951907 A JPS5951907 A JP S5951907A JP 16263882 A JP16263882 A JP 16263882A JP 16263882 A JP16263882 A JP 16263882A JP S5951907 A JPS5951907 A JP S5951907A
Authority
JP
Japan
Prior art keywords
polymeric substance
formula
irradiation
alkyl
heating
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
Application number
JP16263882A
Other languages
Japanese (ja)
Other versions
JPH0261969B2 (en
Inventor
Shuji Saeki
周二 佐伯
Naofumi Suzuki
直文 鈴木
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DKS Co Ltd
Original Assignee
Dai Ichi Kogyo Seiyaku Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dai Ichi Kogyo Seiyaku Co Ltd filed Critical Dai Ichi Kogyo Seiyaku Co Ltd
Priority to JP16263882A priority Critical patent/JPS5951907A/en
Publication of JPS5951907A publication Critical patent/JPS5951907A/en
Publication of JPH0261969B2 publication Critical patent/JPH0261969B2/ja
Granted legal-status Critical Current

Links

Landscapes

  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Polyethers (AREA)
  • Graft Or Block Polymers (AREA)

Abstract

PURPOSE:To impart semi-permanent hydrophilicity to the surface of a polymeric substance by a simple method, by grafting a specified monomer onto the surface of the polymeric substance by heating or irradiation with light. CONSTITUTION:In imparting hydrophilicity to the surface of a polymeric substance, a monomer of the formula (wherein R is a 5-18C alkyl, aralkyl or alkylaryl, R1 is ethylene, R2 is propylene or butylene, X is H or CH3, n and m are each 0 or an integer, and n+m=4-100) onto the surface of the polymeric substance by heating or irradiation with light. The compound of the formula is one prepared by condensing (i) a compound obtained by adding ethylene oxide and/or propylene oxide and/or butylene oxide to an alicyclic alcohol or an alkyl- substituted or unsubstituted phenol, with (ii) (meth)acrylic acid or a (meth) acrylate ester.

Description

【発明の詳細な説明】 本発明は高分子物質表面の親水性化方法に関する。[Detailed description of the invention] The present invention relates to a method for making the surface of a polymeric substance hydrophilic.

高分子物質表面の親木性化は、その表面に接着性、濡れ
、生体適合性、帯電性、染色性などの特性をイリ°与す
るため、さまざまな処理手段を用いて行われる。
The surface of a polymeric substance is made wood-friendly by using various processing means in order to impart properties such as adhesiveness, wettability, biocompatibility, electrostatic property, and dyeability to the surface.

例えば、ラミホー1〜熱処理、放射線処理、プラズマ処
理、光照射処理などである。とりわけ熱処理、光照射処
理によるグラ中1〜処理については、学問的にも極めて
興味深い対象として過去より、数多く研究され、それに
用いられるモノマ、−としては―メチロールアクリルア
ミド、スチレン、アクリロニ1−リル、クリシジルメタ
クリレ−1−、メタクリル酸メチル、メタクリルアミド
、アクリルアミド、耐″醸ビニル、アクリル酸などがあ
り、高分子物質の機能向−1−を目途として現在も広く
研究が進められいてる。しかるに、実際的意味において
、高分子物質表面の親ないのが実情であり、多くは、練
り込み、あるい(Jトセi6)塗?11″によ1j、そ
σ月1的を達しでいるにい/)のか112 :仄−CT
、ちる。
For example, Lamiho 1 - heat treatment, radiation treatment, plasma treatment, light irradiation treatment, etc. In particular, heat treatment and light irradiation treatments have been extensively researched in the past as extremely interesting subjects, and the monomers used for this process include methylol acrylamide, styrene, acryloni-1-lyl, and chlorine. There are compounds such as sidyl methacrylate, methyl methacrylate, methacrylamide, acrylamide, vinyl-resistant vinyl, and acrylic acid, and extensive research is currently underway with the aim of improving the functionality of polymeric substances.However, In a practical sense, the reality is that the surface of a polymeric material is not suitable, and in many cases it is difficult to reach the target by kneading or (J TOSE i6) coating. /) or 112: 组-CT
, chiru.

本発明R,、:、は l!’l+分子−物1g′7表面
り、−、’1′>l;久的な親ノー(・1′1加1、と
11 ;++ iJ防電、防膏処叩を施オためfΦ′l
の千ツマ−j:Tiの長面グラフ1−処理について4・
、9意(il[究し、八X、いI↓、極めで優旧た・1
′1能をイイずろモノマー〆4) +゛、げにその処理
方法を(昌1出ずに至1″− リ5本発明に到達し、でものびある。
The present invention R, :, is l! 'l + molecule - substance 1g'7 surface, -, '1'>l; permanent parent no (・1'1 addition 1, and 11; ++ iJ electrical protection, plaster treatment, fΦ' l
1,000 Tsuma-j: Ti long surface graph 1- About processing 4.
, 9 meaning (il [Ultimate, 8X, I↓, Extremely superior, 1
We have reached the present invention, which has been developed to improve the monomer's performance, and how to treat it (4).

兄 叩1−.、高う)1′物!rT ハ面#親4く性f’s
 ”1ルニ1tヅ’H’i L+ 。
Brother hitting 1-. , expensive) 1′ thing! rT ha face #parent 4 f's
``1 luni 1tzu'H'i L+.

一般式 %式%: (() げ−だし71式中lくは(1: 5= (じl 11の
アルキル、アラルキルまたはアルキルアリール基、R)
は二Iユチレン基、1り2はフパ[1ピレン、またはフ
チ+/ y 」3、Xは11または(f〕H3,お、上
び++ 。
General formula % formula %: (() In formula 71, 1: 5= (di 11 alkyl, aralkyl or alkylaryl group, R)
is 2 I ytylene group, 1 2 is hupa [1 pyrene, or rim+/y'3,

+1’lはりまたは整数、かつ++ 十m = ’Iへ
一100Cあろ1、) て示びれるモノマーを加熱もしくは尤11((旧により
高分子物質表面にタラ攻1−化さ仕ることを′1、ν徴
どすン)高分子物質表面のれ!水性化か−、を提供する
ものである。
+1'l beam or integer, and ++ 10m = 'I to 100C 1,) Heating the monomer shown as '1, ν characteristic) The surface of a polymeric substance is made water-based.

本発明において、前記−・般式(1)でボされる(]−
合物は、アミルアルコール、オクチル)′ル」−ル、う
「”ノリルアルコール、ステアリルアル−一−ルといっ
たアルコール類、もし7くはシタロt\キシル7′ルコ
ールなどのアリサイクIJツク2J:アル」−ル類ある
いはフレソール、S +:! c−フチルフェノール、
ノニルフェノールなとのアルキル1醒換フエノールもし
くは非置換フェノール類に公/f11の方(′lモてエ
ヂレンオキシ1へおよび/またはプロピレンオキシ1−
および/またはブチ(ノンA−〜シ1−をイ:I加せし
めて得られる化合物にアクリル前、メタクリル酸、アク
リル酸エステル、もしく +tスタクリル酸エステルを
縮合せしめて盆トらAしる化合物である。
In the present invention, (]- is represented by the general formula (1).
Compounds include alcohols such as amyl alcohol, octyl alcohol, noryl alcohol, and stearyl alcohol; ” - Les or Fresols, S +:! c-phthylphenol,
Alkyl 1-substituted phenols or unsubstituted phenols such as nonylphenol can be used for conversion to ethyleneoxy 1 and/or propyleneoxy 1-
and/or a compound obtained by adding acrylic acid, methacrylic acid, acrylic ester, or +t staacrylic ester to a compound obtained by adding non-A- to cy-1- to It is.

また、本発明においで高分子物質とは、−1:とI7で
合成高分子化合物であり、ポリエステル、ボ1Jアミ1
−、ポリアクリロニ1ヘリルどいった合成繊組−から、
ポリエステル樹脂、ポリアミド樹脂、アクリル樹脂、ポ
リスチレン樹脂、A r3S 4itl脂ン(・どの合
1戊粒目指の成型品およびフィルj、をいう。
In addition, in the present invention, the polymer substance is a synthetic polymer compound consisting of -1: and I7, such as polyester, bo1jami1
- from synthetic fibers such as polyacryloni 1-helical,
Polyester resins, polyamide resins, acrylic resins, polystyrene resins, A r3S 4itl resins (all of which refer to molded products and fills aimed at one-piece grains).

これl゛、高分子物質の表面処理力aくどしでば、に記
一般式(1)で示される七ツマ−の水溶?1νあるスジ
1ノー、コーチrンクなどの方法による表面ンクマ布を
行−】だのも、そのままもし、くはす吃燥f名・、5、
・さ処理の場合は、l □ (1〜l 80 ’(二し
;で31)秒〜濱)勺、1、JV(紫外線)照射の場合
、主どして:l t)l)〜/15f)Ill 71に
最大波長をもつ光で10秒〜5分間の照射をjfi二し
7(はN2′f?−囲気中0行うことにより表面処理を
行う、。
If we consider the surface treatment power of the polymeric substance, then what is the aqueous solution of the seven polymers represented by the general formula (1)? 1ν There is a streak 1 no, the surface is coated by a method such as a coach link.
・In the case of UV treatment, l □ (1 to l 80'(two; 31) seconds to 1), 1, in the case of JV (ultraviolet) irradiation, mainly: l t) l) to / 15f) Surface treatment is performed by irradiating Ill 71 with light having the maximum wavelength for 10 seconds to 5 minutes, and then performing 7 (N2'f? - 0 in an ambient atmosphere).

こυ〕■す合、熱重合に才♂いでは、1列えはj重硫酸
アア□: Z ll、過ヤイ1゜うつ。イア5、過酸イ
1、ッゾ(ルンJ・どをJl、イY什し7めろのかIf
ましく、また)+6jj((jl・lc7戸J3合は、
ベンゾフェノン、ビアセヂル、/\ンツーrルアルWル
エーデル、過酸化ベンツ・アルなど増感剤を共存さぜる
ことかりrましい。
This is a talented, thermal polymerization, and one row is J -A -LL, Z LL, 1 ゜ depression. Ia 5, peracid I 1, zzo (Run J, Dowo Jl, IY Shishi 7 Mello? If
Indeed, again) +6jj ((jl/lc 7 houses J3 go,
It is prudent to coexist with sensitizers such as benzophenone, viasedil, alcohol, and benzalyl peroxide.

また、表面処理後は、水洗もしくは溶剤洗浄を行い、未
グラ孟1ヘモノマーオ9よび^′〕i分子物Jnイ(面
1・の重合物を洗浄してもよい。
Further, after the surface treatment, washing with water or solvent may be performed to wash the polymers on surface 1.

以1−のとおり、極めて簡便な方法で表面処理された高
勿子物質の表面ば、驚嘆ずへきことに梗めで好適な親水
性を示し、防f[、防曇]′1、流滴処理などが、半永
久的に完遂することカビCさ7,1゜以下本発明を実施
例により説明する。
As shown in 1-1 below, the surface of the Takanuko material, which has been surface-treated using an extremely simple method, surprisingly exhibits a particularly thick and suitable hydrophilicity, and has excellent anti-f[, anti-fog]'1 and droplet treatment. The present invention will be described by way of examples.

(実施例中の部、%は重−■部を表す。)実施例 市販のボリエステルフ、rル13を10(・mmにLJ
J191し・、これを表−1に示した++V7 i告物
質(イj1.1j1(II″ンブル)に該化合物あたり
、4重置′/、の;、H,+。
(Parts and % in Examples represent parts by weight.) Example: Commercially available polyester foam, R 13, was added to 10 (LJ
J191 and this was added to the ++V7i reporting substance (Inch1.1j1 (II'') shown in Table 1) per compound, 4 times '/,;,H,+.

硫酸フ′ンモニウ11を含む5 %氷1容イ′1シに1
フ7古じ、1時曲後浴より引きにげで一昼夜風・)・λ
じlF= −また、−・方で表−1に示した構j告物質
に1ヅ。
1/1 cup of 5% ice containing 11 sulfuric acid
Fu7 old, from the 1 o'clock bath, it's all day and night wind・)・λ
1F = -Also, 1 for each of the suspected substances listed in Table 1.

ル のペンツフェノンを加えた!; %酢酸工千称水溶液を
調製し、同打冒;ボリエステルノ、rル11を浸漬し、
1時間後、浴より引き1.げで ・仔実施例2 市販のボリスチ1ノン樹脂ペレッ1−を17υ〜181
1℃[f−ル棟り(3分間)し、180℃にて30秒、
1])旧UX/−て加圧プレスし、冷却プレスを行い、
J m +n X Iυen+ X 10 cmの樹脂
板を成形した。
Added Pentsuphenone! ; Prepare a % acetic acid aqueous solution and immerse polyester resin 11 in the same solution;
After 1 hour, remove from the bath 1. Example 2 Commercially available Boristi 1 non-resin pellets 1-17υ~181
1℃ [f-le heating (3 minutes), 180℃ for 30 seconds,
1]) Press with the old UX/-, perform cooling press,
A resin plate of J m +n X Iυen+ X 10 cm was molded.

実施例1同様にして、得られた5%水溶液なら行った。The obtained 5% aqueous solution was treated in the same manner as in Example 1.

表面処理後、その表面の表面固有抵抗を測定した結果を
表−2に示した。
After the surface treatment, the surface resistivity of the surface was measured and the results are shown in Table 2.

表−2 表−2により、本発明例は表面固有抵抗値が低く、マ)
F電防止性が優九でいることが確認でさる、リ″■にて
光照射して処理した表面処理ポリエステルフィルムを温
水中(60℃)に24時間浸漬し、乾燥後のフィルムの
接触角および表面固イT 41(抗(値)を測定した結
果を表−13に示す。
Table-2 According to Table-2, the present invention example has a low surface resistivity value.
The surface-treated polyester film, which was confirmed to have excellent anti-F electrostatic properties by light irradiation, was immersed in warm water (60°C) for 24 hours, and the contact angle of the film was determined after drying. The results of measuring the surface hardness T41 (value) are shown in Table 13.

表−:(Table - :(

Claims (1)

【特許請求の範囲】 高分子物質表面を親水性化するに際し、一般式 %式%(1) (ただし2式中J(はCs −Cr。のアルキル、アラ
ルキルまたはアルキルアリール基、1(lはエチレン基
、R2はプロピレン、またはブチレン基、Xは■4また
はCH3−およびn 。 InはOまたは整数、かつn + m = 4〜100
である。) で示される七ツマ−を加熱もしくは光照射により高分子
物質表面にグラ中1−化させることを特徴どする高分子
物質表面の親水性化方法。
[Claims] When making the surface of a polymeric substance hydrophilic, the general formula % formula % (1) (wherein J (in formula 2) is an alkyl, aralkyl or alkylaryl group of Cs -Cr, 1 (l is Ethylene group, R2 is propylene or butylene group, X is ■4 or CH3- and n. In is O or an integer, and n + m = 4 to 100
It is. 1. A method for making a surface of a polymeric material hydrophilic, which comprises converting a 7-mer represented by the following formula into a monomer on the surface of a polymeric material by heating or irradiation with light.
JP16263882A 1982-09-17 1982-09-17 Imparting hydrophilicity to surface of polymeric substance Granted JPS5951907A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP16263882A JPS5951907A (en) 1982-09-17 1982-09-17 Imparting hydrophilicity to surface of polymeric substance

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP16263882A JPS5951907A (en) 1982-09-17 1982-09-17 Imparting hydrophilicity to surface of polymeric substance

Publications (2)

Publication Number Publication Date
JPS5951907A true JPS5951907A (en) 1984-03-26
JPH0261969B2 JPH0261969B2 (en) 1990-12-21

Family

ID=15758417

Family Applications (1)

Application Number Title Priority Date Filing Date
JP16263882A Granted JPS5951907A (en) 1982-09-17 1982-09-17 Imparting hydrophilicity to surface of polymeric substance

Country Status (1)

Country Link
JP (1) JPS5951907A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0421345B1 (en) * 1989-10-03 1996-03-20 Mitsubishi Chemical Corporation Process for forming cured-resin layer having an antistatic surface
EP0906921A1 (en) * 1997-10-03 1999-04-07 Mitsubishi Chemical Corporation Modified ethylene resin having improved wettability
JP2010053237A (en) * 2008-08-28 2010-03-11 Chisso Corp Synthetic resin molded article and method for controlling hydrophilic property and hydrophobic property of surface of the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0421345B1 (en) * 1989-10-03 1996-03-20 Mitsubishi Chemical Corporation Process for forming cured-resin layer having an antistatic surface
EP0906921A1 (en) * 1997-10-03 1999-04-07 Mitsubishi Chemical Corporation Modified ethylene resin having improved wettability
JP2010053237A (en) * 2008-08-28 2010-03-11 Chisso Corp Synthetic resin molded article and method for controlling hydrophilic property and hydrophobic property of surface of the same

Also Published As

Publication number Publication date
JPH0261969B2 (en) 1990-12-21

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