JPWO2011152498A1 - 撥水撥油剤および撥水撥油剤組成物 - Google Patents
撥水撥油剤および撥水撥油剤組成物 Download PDFInfo
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- JPWO2011152498A1 JPWO2011152498A1 JP2012518453A JP2012518453A JPWO2011152498A1 JP WO2011152498 A1 JPWO2011152498 A1 JP WO2011152498A1 JP 2012518453 A JP2012518453 A JP 2012518453A JP 2012518453 A JP2012518453 A JP 2012518453A JP WO2011152498 A1 JPWO2011152498 A1 JP WO2011152498A1
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- Prior art keywords
- water
- oil repellent
- compound
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- fluorine
- Prior art date
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Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/572—Reaction products of isocyanates with polyesters or polyesteramides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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Abstract
Description
[1]下記含フッ素化合物(a)とポリイソシアネート化合物(b)との反応生成物からなる撥水撥油剤。
含フッ素化合物(a):Rf−X−Ph−Y−Z
Rfは炭素数1〜6のポリフルオロアルキル基を、Xは単結合、炭素数1〜4のアルキレン基、(CH2)mO(CH2)n(mおよびnは互いに独立して0〜4の整数)、または(CH2)pOCO(pは1〜4の整数)を、Phはフェニレン基を、Yは単結合、炭素数1〜4のアルキレン基、または(CH2)qO(CH2)r(qは0〜4の整数、rは1〜4の整数)を、ZはOHまたはNHR(Rは水素原子または炭素数1〜6のアルキル基)をそれぞれ表す。
[2]前記反応生成物が、イソシアネート基を有しない[1]に記載の撥水撥油剤。
[3]前記含フッ素化合物(a)のRfが炭素数4〜6のパーフルオロアルキル基である、[1]または[2]に記載の撥水撥油剤。
[4]前記含フッ素化合物(a)が下式(a1)または(a2)で表される含フッ素化合物である、[1]〜[3]に記載の撥水撥油剤。
[6][1]〜[5]のいずれかに記載の撥水撥油剤と溶媒を含有する撥水撥油剤組成物。
本発明の撥水撥油剤組成物は、物品の表面に充分な撥水撥油性を付与でき、かつ環境負荷が低い。
本発明における含フッ素化合物(a)は、下式(I)で表されるフェニレン基を有する含フッ素アルコールまたは含フッ素アミンであり、それらの2種以上を使用することもできる。
Rf−X−Ph−Y−Z ・・・(I)
ただし、Rfは炭素数1〜6のポリフルオロアルキル基であり、Xは単結合、炭素数1〜4のアルキレン基、(CH2)mO(CH2)n(mおよびnは互いに独立して0〜4の整数)、または(CH2)pOCO(pは1〜4の整数)であり、Phはフェニレン基であり、Yは単結合、炭素数1〜4のアルキレン基、または(CH2)qO(CH2)r(qは0〜4の整数、rは1〜4の整数)であり、ZはOHまたはNHR(Rは水素原子または炭素数1〜6のアルキル基)である。
本発明における含フッ素化合物(a)の製造方法は、特に限定されるものではない。例えば、下記の製造方法によって製造することができる。
X1OCOPhZ1 + C6F13C2H4OH → C6F13C2H4OCOPhZ1
上記反応においては、触媒として、4−トルエンスルホン酸1水和物、硫酸等の酸、または炭酸カリウム、トリエチルアミン等の塩基を用いることが好ましい。反応は、無溶媒、もしくは溶媒中で行われ、なかでも、トルエン、2−ブタノン等を用いることができる。
反応条件として好ましくは、反応容器:ガラス製、SUS製等、温度:50〜150℃、圧力:−0.1〜1MPa、雰囲気:窒素、アルゴン等によるガス置換、時間:1〜100時間等の条件が挙げられる。さらに必要に応じて反応副生成物を留去しながら反応を行うことが好ましい。
本発明におけるポリイソシアネート化合物(b)とは、イソシアネート基を2つ以上有する化合物である。ポリイソシアネート化合物(b)としては、イソシアネート基を2以上有する脂肪族系、脂環族系、芳香族系等のポリイソシアネート、該ポリイソシアネートの2種類以上の混合物、これらを変性して得られる変性ポリイソシアネート等が挙げられる。
ポリイソシアネート化合物(b)におけるイソシアネート基含有量は、5〜40質量%が好ましく、10〜30質量%がより好ましく、15〜30質量%が最も好ましい。
本発明における反応生成物には、含フッ素化合物(a)以外にも、イソシアネート基と反応性のある活性水素基を有する化合物(c)とポリイソシアネート化合物(b)との反応生成物を含有していてもよく、ポリイソシアネート化合物(b)と、含フッ素化合物(a)およびイソシアネート基と反応性のある活性水素基を有する化合物(c)との反応生成物を含有していてもよい。
活性水素基としては、例えば、水酸基、アミノ基、メルカプト基等が挙げられる。また、イソシアネート基をブロック化しうるブロック化剤であってもよい。さらには、水であってもよい。イソシアネート基と水を反応させると加水分解によりアミノ基が生成するが、生成したアミノ基はさらに別のイソシアネートと反応してウレア結合を形成し、分子中に架橋構造を導入することができる。
本発明における反応生成物は、化合物(c)がポリイソシアネート化合物(b)のイソシアネート基に対して好ましくは0〜50%反応したものであり、より好ましくは0〜30%反応したものである。かかる範囲を適当に調整して化合物(c)との反応生成物を含有せしめることにより、実質的に本発明の撥水撥油剤の効果(環境に対する負荷が低く撥水撥油性に優れる)を損なわずに、他の特性を付与することができる。化合物(c)として、2種以上を用いてもよい。
本発明における反応生成物は、含フッ素化合物(a)とポリイソシアネート化合物(b)を反応させることによって得られる。含フッ素化合物(a)以外の化合物(c)も反応させる場合、ポリイソシアネート化合物(b)に、含フッ素化合物(a)と化合物(c)を順次反応させる、または含フッ素化合物(a)と化合物(c)の混合物を反応させる製造方法である。反応の際には、適宜触媒および反応溶媒を用いることができる。
ケトンとしては、アセトン、メチルエチルケトン、2−ペンタノン、3−ペンタノン、2−ヘキサノン、メチルイソブチルケトン(以下、MIBKと記す。)等が挙げられる。
エステルとしては、酢酸メチル、酢酸エチル、酢酸ブチル、プロピオン酸メチル等が挙げられる。
エーテルとしては、メチルtert−ブチルエーテル、ジイソプロピルエーテル、シクロペンチルメチルエーテルなどのアルキルエーテル、ジオキサン、テトラヒドロフランなどの環状エーテル等が挙げられる。
反応溶媒としては、特に、溶解性の観点から、クロロホルム、メチルエチルケトン、MIBK、シクロヘキサノン、DMFが好ましい。反応溶媒は、上記1種を単独で用いてもよく、2種以上を併用して用いてもよい。
反応温度としては、0〜200℃、好ましくは20〜80℃が採用される。反応時間は1〜200時間が好ましい。
本発明の撥水撥油剤組成物は、前記撥水撥油剤と溶媒と、必要に応じて界面活性剤および添加剤を含む組成物である。本発明の撥水撥油剤組成物の形態としては、撥水撥油剤が溶媒中に溶解している、または微粒子として分散している形態であることが好ましい。
(i)上記反応溶媒を使用した製法により撥水撥油剤の溶液を得た後、他の溶媒、必要に応じて添加剤を加える方法。
(ii)上記反応溶媒を使用した製法により撥水撥油剤の溶液を得た後、撥水撥油剤を分離し、撥水撥油剤に溶媒、必要に応じて添加剤を加える方法。
(iii)上記反応溶媒を使用した製法により撥水撥油剤の溶液を得た後、他の溶媒、界面活性剤、必要に応じて添加剤を加え、必要に応じて脱溶媒する方法。
(iv)上記反応溶媒を使用した製法により撥水撥油剤の溶液を得た後、撥水撥油剤を分離し、撥水撥油剤に溶媒、界面活性剤、必要に応じて添加剤を加え、必要に応じて脱溶媒する方法。
なお、前記固形分濃度は、撥水撥油剤の他、界面活性剤(乳化剤)も含む濃度である。ここで、固形分濃度とは、加熱前の撥水撥油剤組成物の質量と、120℃の対流式乾燥機にて4時間乾燥した後の質量とから計算される。
撹拌機を備えた反応器(内容積500mL、ガラス製)に、窒素雰囲気下、4−ヒドロキシ安息香酸(135.0g)、4−トルエンスルホン酸1水和物(9.30g)、およびC6F13CH2CH2OH(533.8g)を投入して撹拌した。つづいて反応器の内温が140℃になるように加熱し、反応器を減圧(0〜−0.05MPa)にして水を留去しながら6時間撹拌した。さらに反応器の内温を110℃に下げ、さらに減圧にして過剰のC6F13CH2CH2OHを留去した。
撹拌機を備えた反応器(内容積500mL、ガラス製)に、窒素雰囲気下、4−アミノ安息香酸エチル(100.0g)、炭酸カリウム(8.37g)、およびC6F13CH2CH2OH(440.8g)を投入して撹拌した。つづいて反応器の内温が120℃になるように加熱し、反応器を減圧(0〜−0.05MPa)にしてエタノールを留去しながら12時間撹拌した。さらに減圧にして過剰のC6F13CH2CH2OHを留去した。
反応溶液の1滴をKBr窓材にたらしてはさみ、透過型FT−IR測定を行った。イソシアネート基に由来する2280cm−1付近のピークが完全に消失するか、またはピークがほぼ消失し、さらに24時間反応を続けてもピークに変化が見られなくなった時点で反応を終了した。
反応後の溶液の1H−NMR測定を行うことにより、含フッ素化合物(a1)(実施例1〜4)、含フッ素化合物(a2)(実施例5〜6)およびC6F13C2H4OH(比較例1〜2)の反応転化率を算出した。すなわち、原料の化学シフトに対して、イソシアネートと反応した後の化学シフトは主に低磁場側に現れるため、それらのシグナルの積分強度比から転化率を求めた。
撹拌機を備えた100mLのガラス製反応器に、デスモジュールN−3200(住化バイエルウレタン社製、HDIビウレット変性体、イソシアネート基含有量:22.7質量%)の2.77g、化合物(a1)の7.23g、触媒としてトリエチルアミンの0.076g、およびMIBKの40.0gを入れ、室温下48時間撹拌し、反応生成物である含フッ素ウレタン化合物を含有する反応溶液を得た。反応終了後の反応溶液のFT−IRでイソシアネート基のピークが消失していた。また、1H−NMRによる化合物(a1)の転化率は98%であった。
撹拌機を備えた100mLのガラス製反応器に、デスモジュールN−3200の3.37g、C6F13C2H4OHの6.63g、触媒としてジブチルすずジラウレートの0.0013g、およびMIBKの40.0gを入れ、80℃に加温して3時間撹拌し、反応生成物である含フッ素ウレタン化合物を含有する反応溶液を得た。反応終了後の反応溶液のFT−IRでイソシアネート基のピークが消失していた。また、1H−NMRによるC6F13C2H4OHの転化率は99%であった。
撹拌機を備えた100mLのガラス製反応器に、デュラネートTHA−100(旭化成ケミカルズ社製、HDIヌレート変性体、イソシアネート基含有量:21.2質量%)の2.90g、化合物(a1)の7.10g、触媒としてトリエチルアミンの0.074g、およびMIBKの40.0gを入れ、室温下48時間撹拌し、反応生成物である含フッ素ウレタン化合物を含有する反応溶液を得た。反応終了後の反応溶液のFT−IRでイソシアネート基のピークがほぼ消失していた。また、1H−NMRによる化合物(a1)の転化率は95%であった。
撹拌機を備えた100mLのガラス製反応器に、デュラネートTHA−100の3.52g、C6F13C2H4OHの6.48g、触媒としてジブチルすずジラウレートの0.0012g、およびMIBKの40.0gを入れ、80℃に加温して3時間撹拌し、反応生成物である含フッ素ウレタン化合物を含有する反応溶液を得た。反応終了後の反応溶液のFT−IRでイソシアネート基のピークが消失していた。また、1H−NMRによるC6F13C2H4OHの転化率は99%であった。
撹拌機を備えた100mLのガラス製反応器に、コスモネートM−200(三井化学ポリウレタン社製、ポリメリックMDI、イソシアネート基含有量:31.5質量%)の2.16g、化合物(a1)の7.84g、触媒としてトリエチルアミンの0.082g、およびMIBKの40.0gを入れ、室温下100時間撹拌し、反応生成物である含フッ素ウレタン化合物を含有する反応溶液を得た。反応終了後の反応溶液のFT−IRでイソシアネート基のピークがほぼ消失していた。また、1H−NMRによる化合物(a1)の転化率は90%であった。
撹拌機を備えた100mLのガラス製反応器に、TDI(東京化成工業社製、イソシアネート基含有量:48.3質量%)の1.52g、化合物(a1)の8.48g、触媒としてトリエチルアミンの0.089g、およびMIBKの40.0gを入れ、室温下100時間撹拌し、反応生成物である含フッ素ウレタン化合物を含有する反応溶液を得た。反応終了後の反応溶液のFT−IRでイソシアネート基のピークがほぼ消失していた。また、1H−NMRによる化合物(a1)の転化率は92%であった。
撹拌機を備えた100mLのガラス製反応器に、TDIの1.53g、化合物(a2)の8.47g、およびMIBKの40.0gを入れ、80℃に加温して100時間撹拌し、反応生成物である含フッ素ウレア化合物を含有する反応溶液を得た。反応終了後の反応溶液のFT−IRでイソシアネート基のピークがほぼ消失していた。また、1H−NMRによる化合物(a2)の転化率は88%であった。
撹拌機を備えた100mLのガラス製反応器に、MDI(東京化成工業社製、イソシアネート基含有量:33.6質量%)の2.06g、化合物(a2)の7.94g、およびMIBKの40.0gを入れ、80℃に加温して100時間撹拌し、反応生成物である含フッ素ウレア化合物を含有する反応溶液を得た。反応終了後の反応溶液のFT−IRでイソシアネート基のピークがほぼ消失していた。また、1H−NMRによる化合物(a2)の転化率は85%であった。
上記実施例1〜6、比較例1〜2で得られた反応溶液のそれぞれについて、下記の方法にて試験板を作製して、撥水撥油性を評価した。
得られた反応溶液を固形分濃度が1.0質量%となるようにアセトン(実施例1〜4および比較例1〜2)またはDMF(実施例5〜6)にて希釈し、処理液とした。次いで、以下に示す方法に従って前記各処理液を用いて、ガラス板上に皮膜を形成させ、該皮膜の撥水撥油性評価を行った。評価結果を表1に示す。
洗浄済みのガラス板を基材として用い、その上に上記で得られた処理液をスピンコート法にて、1000rpmの条件で10秒間塗布した。この後、120℃にて60分間加熱処理して皮膜を形成し、試験板を得た。上記処理液すべてについて、これを用いて皮膜形成させた試験板を作製し、得られた各試験板を用いて、該皮膜上の水およびn−ヘキサデカンの接触角を測定することにより、上記実施例、比較例で作製した撥水撥油剤を含む処理液から得られる皮膜の撥水撥油性を評価した。なお、接触角の測定は、協和界面科学社製CA−Xを用いて行った。
上記実施例1〜6、比較例1〜2で得られた反応溶液のそれぞれについて、下記の方法にて試験布を作製して、撥水性および撥油性を評価した。
得られた反応溶液を固形分濃度が0.6g/Lとなるようにアセトン(実施例1〜4および比較例1〜2)またはDMF(実施例5〜6)にて希釈し、試験液とした。これらの試験液にポリエステル布を浸漬し、ウェットピックアップが100質量%となるように絞った。これを、常温で24時間乾燥し、さらに170℃で60秒間乾燥したものを試験布とした。
試験布の撥水性の評価はJIS−L1092のスプレー試験により行い、表2に示す撥水性等級で表した。撥水性等級に+(−)を記したものは、それぞれの性質がわずかに良い(悪い)ことを示す。評価結果を表1に示す。
AATCC−TM118−1966の試験法に従い、表3に示す試験溶液を、上記で作製した各試験布A上の2ヶ所にそれぞれ数滴(径約4mm)置き、30秒後の浸漬状態により表3に示す撥油性等級(ナンバ)で表した。なお、撥油性等級に+(−)を記したものは、それぞれの評価がわずかに良い(悪い)ことを示す。評価結果を表1に示す。
なお、2010年6月4日に出願された日本特許出願2010−129012号の明細書、特許請求の範囲、及び要約書の全内容をここに引用し、本発明の明細書の開示として、取り入れるものである。
Claims (8)
- 下記含フッ素化合物(a)とポリイソシアネート化合物(b)との反応生成物とを含有することを特徴とする撥水撥油剤。
含フッ素化合物(a):Rf−X−Ph−Y−Z
Rfは炭素数1〜6のポリフルオロアルキル基を、Xは単結合、炭素数1〜4のアルキレン基、(CH2)mO(CH2)n(mおよびnは互いに独立して0〜4の整数)、または(CH2)pOCO(pは1〜4の整数)を、Phはフェニレン基を、Yは単結合、炭素数1〜4のアルキレン基、または(CH2)qO(CH2)r(qは0〜4の整数、rは1〜4の整数)を、ZはOHまたはNHR(Rは水素原子または炭素数1〜6のアルキル基)をそれぞれ表す。 - 前記反応生成物が、イソシアネート基を有しない請求項1に記載の撥水撥油剤。
- 前記含フッ素化合物(a)のRfが炭素数4〜6のパーフルオロアルキル基である、請求項1または2に記載の撥水撥油剤。
- 前記ポリイソシアネート化合物(b)が、ヘキサメチレンジイソシアネートまたはその変性体である、請求項1〜4のいずれかに記載の撥水撥油剤。
- さらに、ポリイソシアネート(b)とイソシアネート基と反応性のある活性水素基を有する化合物(c)との反応生成物、またはポリイソシアネート(b)と、含フッ素化合物(a)およびイソシアネート基と反応性のある活性水素基を有する化合物(c)との反応生成物を含有する請求項1〜5のいずれかに記載の撥水撥油剤。
- 請求項1〜6のいずれかに記載の撥水撥油剤と溶媒を含有する撥水撥油剤組成物。
- 固形分濃度が、0.05〜10質量%である請求項7に記載の撥水撥油剤組成物。
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