WO2021065527A1 - 含フッ素硬化性組成物及び物品 - Google Patents
含フッ素硬化性組成物及び物品 Download PDFInfo
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- WO2021065527A1 WO2021065527A1 PCT/JP2020/035174 JP2020035174W WO2021065527A1 WO 2021065527 A1 WO2021065527 A1 WO 2021065527A1 JP 2020035174 W JP2020035174 W JP 2020035174W WO 2021065527 A1 WO2021065527 A1 WO 2021065527A1
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- fluorine
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- compound
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Classifications
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- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G65/48—Polymers modified by chemical after-treatment
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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Abstract
Description
しかし、紫外線以外の硬化システムによる硬化性組成物で、含フッ素溶剤を必須とせず、硬化性組成物に容易に溶解し、上記紫外線硬化型ハードコート剤と同等以上に、得られる硬化物表面に撥水撥油性及び防汚性、耐指紋性等の性能を付与できる表面改質剤については十分な検討がなされておらず、このような条件の上で使用しやすく性能が出やすい表面改質剤の要求が高まっている。
[1]
熱又は湿気により硬化物を与える硬化性成分(A)と、下記一般式(1)
[McRbSi-Z2]a-Q1-Z1-Rf-Z1-Q1-[Z2-SiRbMc]a
(1)
(式中、Rfは数平均分子量1,500~20,000の2価パーフルオロポリエーテル基である。
Z1はそれぞれ独立に2価の連結基であり、酸素原子、窒素原子、フッ素原子又はケイ素原子を含んでいてもよく、また環状構造及び/又は不飽和結合を有する基であってもよい。
Z2はそれぞれ独立に炭素数2~20の2価の炭化水素基であり、環状構造をなしていてもよく、途中エーテル結合(-O-)を含んでいてもよい。
Q1はそれぞれ独立に(a+1)価の連結基であり、水素原子、炭素原子、酸素原子、ケイ素原子、窒素原子のいずれか2種類以上の原子を含む構造であり、環状をなしていてもよい。
aはそれぞれ独立に1~10の整数であり、bはそれぞれ独立に0~2の整数であり、cはそれぞれ独立に1~3の整数であり、かつ同一ケイ素原子上のb、cにおいてb+c=3を満たす。式(1)における[ ]で括られたa個のZ2はすべてQ1構造中のケイ素原子と結合している。
Rはそれぞれ独立に炭素数1~6の1価の炭化水素基である。
Mはそれぞれ独立に、炭素数1~10のアルコキシ基、炭素数2~10のアルコキシアルキル基、炭素数2~10のアルコキシアルコキシ基、炭素数1~10のアシロキシ基、炭素数2~10のアルケニルオキシ基及びハロゲン基からなる群より選ばれる基である。)
で示されるパーフルオロポリエーテル化合物(b1)を含む表面改質成分(B)とからなり、かつ揮発性成分を除外した硬化性成分(A)100質量部に対して、表面改質成分(B)中のパーフルオロポリエーテル化合物(b1)が0.005~50質量部である含フッ素硬化性組成物。
[2]
表面改質成分(B)が、さらに下記一般式(2)
F-Rf’-F (2)
(式中、Rf’は数平均分子量1,500~20,000の2価パーフルオロポリエーテル基である。)
で示される無官能パーフルオロポリエーテル化合物(b2)を、一般式(1)で示されるパーフルオロポリエーテル化合物(b1)と上記(b2)成分の合計100モル%に対して5モル%未満含み、揮発性成分を除外した硬化性成分(A)100質量部に対して、表面改質成分(B)中の(b1)成分と(b2)成分の合計が0.005~50質量部であり、かつ、常圧における沸点が260℃以下である含フッ素溶剤の含有量が(B)成分全体の1質量%未満である[1]に記載の含フッ素硬化性組成物。
[3]
式(1)、(2)において、Rf及びRf’が、それぞれ以下の2価パーフルオロエーテル基群
-CF2O-
-CF2CF2O-
-CF2CF2CF2O-
-CF(CF3)CF2O-
-CF2CF2CF2CF2O-
-CF2CF2CF2CF2CF2O-
-CF2CF2CF2CF2CF2CF2O-
から選ばれる少なくとも1つの構造からなる繰り返し単位と、炭素数1~6のパーフルオロアルキレン基からなるものである[1]又は[2]に記載の含フッ素硬化性組成物。
[4]
式(1)、(2)において、Rf及びRf’が、以下のいずれか
-CF2O(CF2O)p(CF2CF2O)qCF2-
-CF2CF2O(CF2O)p(CF2CF2O)qCF2CF2-
(式中、pは10~290の整数、qは5~170の整数、p+qは15~295の整数である。-CF2O-と-CF2CF2O-の各繰り返し単位の配列はランダムである。)
-CF(CF3)[OCF2CF(CF3)]sO(CuF2uO)v[CF(CF3)CF2O]tCF(CF3)-
-CF2CF2CF2O[CF(CF3)CF2O]tCF2CF2-
(式中、s、tは独立に1~120の整数であり、かつs+tは4~121の整数であり、uは1~6の整数であり、vは0~10の整数である。)
で示されるものである[1]~[3]のいずれかに記載の含フッ素硬化性組成物。
[5]
式(1)において、Z2が以下の式
-(CH2)w-
(式中、wは2~20の整数である。)
で表されるものである[1]~[4]のいずれかに記載の含フッ素硬化性組成物。
[6]
式(1)において、Q1がそれぞれ独立に少なくとも(a+1)個のケイ素原子を有するシロキサン構造、非置換又はハロゲン置換のシルアルキレン構造、シルアリーレン構造又はこれらの2種以上の組み合わせからなる(a+1)価の連結基である[1]~[5]のいずれかに記載の含フッ素硬化性組成物。
[7]
式(1)において、Q1が環状シロキサン構造である[1]~[6]のいずれかに記載の含フッ素硬化性組成物。
[8]
式(1)において、Z1が以下の群
-CH2CH2-
-CH2CH2CH2-
-CH2CH2CH2CH2-
-CH2OCH2CH2-
-CH2OCH2CH2CH2-
[9]
表面改質成分(B)が、さらにフッ素原子を含まない揮発性有機溶剤(b3)を(b1)成分100質量部に対して10~2,000質量部含むものである[1]~[8]のいずれかに記載の含フッ素硬化性組成物。
[10]
硬化性成分(A)が、水酸基、カルボキシル基、アミノ基、エポキシ基、メルカプト基、イソシアネート基、加水分解性シリル基、シラノール基、又はカルボン酸無水物基を有する化合物から選ばれる少なくとも1種の化合物を含み、熱又は湿気により反応し硬化するものである[1]~[9]のいずれかに記載の含フッ素硬化性組成物。
[11]
硬化性成分(A)が、フッ素原子を含まない加水分解性シラン化合物、加水分解性シロキサン化合物又はシラノール基含有シリコーン樹脂を含むものである[1]~[10]のいずれかに記載の含フッ素硬化性組成物。
[12]
硬化性成分(A)が、テトラアルコキシシラン、トリアルコキシシラン、ジアルコキシシランの少なくとも1つもしくはこれらの部分加水分解縮合物、又は該部分加水分解縮合物の加水分解・部分縮合物を含むものである[1]~[11]のいずれかに記載の含フッ素硬化性組成物。
[13]
硬化性成分(A)が、1分子中にイソシアネート基を2個以上有するフッ素原子を含まない化合物及び1分子中にヒドロキシル基を2個以上有するフッ素原子を含まない化合物を含むものである[1]~[12]のいずれかに記載の含フッ素硬化性組成物。
[14]
硬化性成分(A)が、フッ素原子を含まないエポキシ化合物を含むものである[1]~[13]のいずれかに記載の含フッ素硬化性組成物。
[15]
硬化物の表面の水接触角が100°以上である[1]~[14]のいずれかに記載の含フッ素硬化性組成物。
[16]
[1]~[15]のいずれかに記載の含フッ素硬化性組成物の硬化被膜を表面に有する物品。
本発明の含フッ素硬化性組成物は、熱又は湿気により硬化物を与える硬化性成分(A)と、後述する一般式(1)で示されるパーフルオロポリエーテル化合物(b1)を含む表面改質成分(B)とからなるものである。
本発明の含フッ素硬化性組成物の1つの構成要素である硬化性成分(A)は、熱又は湿気により硬化物を与えるものであり、後述する(b1)及び(b2)成分に該当しない成分によって構成され、常圧における沸点が260℃以下である含フッ素溶剤の含有量が硬化性成分(A)全体の1質量%未満であり、(b1)成分と混合塗工もしくは成型可能であり、かつ硬化後に(b1)成分を硬化物表面に固定可能なものであれば、組成や硬化機構については制限されないが、硬化後に化学結合により(A)成分中の少なくとも1種類の化合物と(b1)成分が固定されることが望ましく、このような(A)成分に含まれる化合物は、後述する一般式(1)のM基である、アルコキシ基、アルコキシアルキル基、アルコキシアルコキシ基、アシロキシ基、アルケニルオキシ基及びハロゲン基のいずれかと反応する官能基を有し、熱又は湿気により硬化するものが好ましい。またフッ素原子を含む場合は、揮発成分とならないため、1つの化合物中に上記Mと反応する官能基を有することが望ましい。
中でも特に、加水分解性シリル基、シラノール基、水酸基、イソシアネート基、エポキシ基を持つ化合物が好ましい。シリル基に結合する加水分解性基として、具体的には、アルコキシ基、オキシム基、イソプロペノキシ基、アセトキシ基を挙げることができる。
また、得られたシリコーン樹脂のアルコキシ基の全てを加水分解するために、該シリコーン樹脂に、さらに必要な量よりも多く水を添加することで、後述するシラノール基を含むシリコーン樹脂を得ることができる。
中でも、上記1分子中にイソシアネート基を2個以上有するフッ素原子を含まない化合物と、1分子中に水酸基を2個以上有するフッ素原子を含まない化合物を併用することが好ましい。
溶剤の配合量は特に制限されないが、好ましくは上記(A)成分に含まれる溶剤を除いた成分の合計100質量部に対して、溶剤の合計が20~10,000質量部、特には50~1,000質量部であるのがよい。
本発明を構成する表面改質成分(B)は、パーフルオロポリエーテル化合物(b1)を含むものであり、該パーフルオロポリエーテル化合物(b1)は、下記一般式(1)で示されるものである。
[McRbSi-Z2]a-Q1-Z1-Rf-Z1-Q1-[Z2-SiRbMc]a
(1)
-CF2O-
-CF2CF2O-
-CF2CF2CF2O-
-CF(CF3)CF2O-
-CF2CF2CF2CF2O-
-CF2CF2CF2CF2CF2O-
-CF2CF2CF2CF2CF2CF2O-
-CF2O-
-CF2CF2O-
-CF(CF3)CF2O-
-CF2CF2CF2O-
-CF2CF2CF2CF2O-
-CF2-
-CF2CF2-
-CF(CF3)-
-CF2CF2CF2-
-CF(CF3)CF2-
-CF2CF2CF2CF2-
-CF2O(CF2O)p(CF2CF2O)qCF2-
-CF2CF2O(CF2O)p(CF2CF2O)qCF2CF2-
(式中、pは10~290、好ましくは15~90、より好ましくは20~60の整数、qは5~170、好ましくは10~120、より好ましくは15~50の整数、p+qは15~295、好ましくは20~210、より好ましくは30~100の整数であり、p、qの組み合わせは、表面改質成分(B)の(b1)成分全体としてのRfの数平均分子量が1,500~20,000を満たす範囲である。-CF2O-と-CF2CF2O-の各繰り返し単位の配列はランダムである。)
-CF(CF3)[OCF2CF(CF3)]sO(CuF2uO)v[CF(CF3)CF2O]tCF(CF3)-
-CF2CF2CF2O[CF(CF3)CF2O]tCF2CF2-
(式中、s、tは独立に1~120、好ましくは2~60、より好ましくは4~20の整数であり、かつs+tは4~121、好ましくは4~100、より好ましくは8~80の整数であり、uは1~6、好ましくは2~4の整数であり、vは0~10、好ましくは0~4の整数である。これらのs、t、u、vの組み合わせは、表面改質成分(B)の(b1)成分全体としてのRfの数平均分子量が1,500~20,000を満たす範囲である。)
-CH2CH2-
-CH2CH2CH2-
-CH2CH2CH2CH2-
-CH2OCH2CH2-
-CH2OCH2CH2CH2-
-(CH2)w-
-CH2CH2CH2OCH2CH2CH2-
-CH2CH2CH2OCH2CH2OCH2CH2CH2-
-CH2CH2CH2OCH2CH2OCH2CH2OCH2CH2CH2-
-(CH2)w-
であり、さらに好ましくは上記式においてwが3~12の整数のものである。
ここで、式(1)における[ ]で括られたa個のZ2はすべてQ1構造中のケイ素原子と結合している。
このようなQ1として、具体的には、下記の構造が例示できる。
[H]a-Q1-Z1-Rf-Z1-Q1-[H]a (3)
(式中、Rf、Z1、Q1、aは前記の通りである。)
CH2=CR2-(Z3)x-SiRbMc (4)
(式中、R、M、b、c、b+cは前記の通りであり、xは0又は1であり、Z3は炭素数1~18の2価の炭化水素基であり、環状構造をなしていてもよく、途中エーテル結合(-O-)を含んでいてもよい。R2は水素原子又は炭素数1~10の1価の炭化水素基であり、Z3の炭素数とR2の炭素数の合計は0~18、好ましくは1~10を満たす。)
-(CH2)w’-
-CH2OCH2CH2CH2-
-CH2OCH2CH2OCH2CH2CH2-
-CH2OCH2CH2OCH2CH2OCH2CH2CH2-
特に好ましくは
-(CH2)w’-
であり、さらに好ましくは上記式においてw’が1~10の整数のものであり、特に好ましくは上記式においてw’が1~6の整数のものである。
CH2=CHSi(OCH3)3
CH2=CHCH2Si(OCH3)3
CH2=CHCH2CH2Si(OCH3)3
CH2=CHCH2CH2CH2Si(OCH3)3
CH2=CHCH2CH2CH2CH2Si(OCH3)3
CH2=CHCH2CH2CH2CH2CH2CH2Si(OCH3)3
CH2=CHSi(OC2H5)3
CH2=CHCH2Si(OC2H5)3
CH2=CHCH2CH2Si(OC2H5)3
CH2=CHCH2CH2CH2Si(OC2H5)3
CH2=CHCH2CH2CH2CH2Si(OC2H5)3
CH2=CHSi(OC3H7)3
CH2=CHCH2Si(OC3H7)3
CH2=CHCH2CH2Si(OC3H7)3
CH2=CHCH2CH2CH2CH2Si(OC3H7)3
CH2=CHSiCH3(OCH3)2
CH2=CHCH2SiCH3(OCH3)2
CH2=CHCH2CH2CH2CH2SiCH3(OCH3)2
CH2=CHSiCH3(OCH2CH3)2
CH2=CHCH2SiCH3(OCH2CH3)2
CH2=CHCH2CH2SiCH3(OCH2CH3)2
CH2=CHCH2CH2CH2CH2SiCH3(OCH2CH3)2
CH2=CHSi(OCH3)3
CH2=CHCH2Si(OCH3)3
CH2=CHCH2CH2Si(OCH3)3
CH2=CHCH2CH2CH2Si(OCH3)3
CH2=CHCH2CH2CH2CH2Si(OCH3)3
CH2=CHCH2CH2CH2CH2CH2CH2Si(OCH3)3
CH2=CHSi(OC2H5)3
CH2=CHCH2Si(OC2H5)3
付加反応触媒の配合量は、式(3)で表される多官能Si-H基を有するパーフルオロポリエーテル化合物に対し、含まれる金属量が0.1~5,000質量ppmとなる量であることが好ましく、より好ましくは0.2~1,000質量ppmとなる量である。
溶剤を使用する場合、その使用量は、式(3)で表される多官能Si-H基を有するパーフルオロポリエーテル化合物100質量部に対して、好ましくは5~2,000質量部であり、より好ましくは50~500質量部である。これより少なければ溶剤による希釈の効果が薄くなり、多ければ希釈度が高くなりすぎて反応速度の低下を招く場合がある。
なお、未反応の式(4)の化合物及びフッ素原子を含まない揮発性溶剤に関しては、(B)成分の構成要素とすることもできる。
Z4-Rf-Z4 (5)
H-Q1-[Z2-SiRbMc]a (6)
(式中、Rf、Q1、Z2、R、M、a、b、c、b+cは前述の通りであり、Z4はそれぞれ独立に末端にSi-H基と付加反応可能な炭素-炭素不飽和結合を1個有する炭素数2~20の酸素原子、窒素原子、フッ素原子及びケイ素原子から選ばれる1種又は2種以上を含んでいてもよい1価の炭化水素基であり、途中環状構造及び/又は不飽和結合を含んでいてもよい。式(6)におけるH及びa個のZ2はすべてそれぞれQ1構造中のケイ素原子と結合している。)
-CH=CH2
-CH2CH=CH2
-CH2CH2CH=CH2
-CH2OCH=CH2
-CH2OCH2CH=CH2
付加反応触媒の配合量は、式(5)で表される末端不飽和基を有するパーフルオロポリエーテル化合物に対し、含まれる金属量が0.1~5,000質量ppmとなることが好ましく、より好ましくは1~1,000質量ppmである。
溶剤を使用する場合、その使用量は、式(5)で表される末端不飽和基を有するパーフルオロポリエーテル化合物100質量部に対して、好ましくは5~2,000質量部であり、より好ましくは50~500質量部である。これより少なければ溶剤による希釈の効果が薄く、多ければ希釈度が高くなりすぎて反応速度の低下を招く場合がある。
F-Rf’-F (2)
Rf’としては、Rfに示したものと同様の構造を取ることができるが、その構造及び数平均分子量、分子量分布はRfと一致していても異なっていてもよい。
CF3O(CF2O)p(CF2CF2O)qCF3
CF3CF2O(CF2O)p(CF2CF2O)qCF2CF3
CF3CF2[OCF2CF(CF3)]sO(CuF2uO)v[CF(CF3)CF2O]tCF2CF3
CF3CF2CF2O[CF(CF3)CF2O]tCF2CF3
(式中、p、q、p+q、s、t、s+t、u、vは前述の通りであり、-CF2O-と-CF2CF2O-の各繰り返し単位の配列はランダムである。)
一方、撥油性、表面浮上性、滑り性向上等の特性向上のためとなる範囲で(b1)成分に対して意図的に(b2)成分を配合してもよい。この場合、無官能パーフルオロポリエーテル化合物(b2)は、上記パーフルオロポリエーテル化合物(b1)及び無官能パーフルオロポリエーテル化合物(b2)の合計100モル%に対して0.1モル%以上とすることが好ましい。
ケトン系有機溶剤の具体例としては、アセトン、メチルエチルケトン(MEK)、メチルイソブチルケトン、シクロヘキサノン等が挙げられる。
エーテル系有機溶剤の具体例としては、ジエチルエーテル、ジイソプロピルエーテル、ジブチルエーテル、テトラヒドロフラン、ポリエチレングリコールモノメチルエーテル(MPEG)、テトラエチレングリコールジメチルエーテル等が挙げられる。
エステル系有機溶剤の具体例としては、酢酸エチル、酢酸プロピル、酢酸ブチル等が挙げられる。
アルコール系有機溶剤の具体例としては、メタノール、エタノール、イソプロパノール、n-ブタノール等が挙げられる。
すなわち、上記表面改質成分(B)を上記硬化性成分(A)である硬化性組成物に対する表面改質剤とすることが可能である。
なお、本発明においては、(A)成分と(B)成分の配合割合として、(b1)成分である一般式(1)中のM基量が、硬化性成分(A)に含まれる、(b1)成分である一般式(1)のM基と反応可能な官能基を有する化合物中の官能基1モルに対して、0.0001~1.5モル、特に0.005~0.095モルの範囲とすることがより好ましい。
[調製例A-1]
攪拌装置、リービッヒ冷却器、滴下ロート及び温度計を備えた1リットルのフラスコに、平均組成式がCH3(CH3O)2SiOSi(OCH3)2CH3で表される化合物96.1質量部、(CH3)2Si(OCH3)2で表される化合物18.0質量部及びトルエン76.9質量部を仕込み、メタンスルホン酸3.4gを攪拌しながら投入した後、さらに水27.0質量部を1時間掛けて滴下し、30℃で12時間熟成させた。
得られた液を炭酸水素ナトリウムで中和し、副生したアルコールを留去し、水洗し、脱水・濾過した後、105℃で3時間放置後測定した不揮発分が40質量%となるようにトルエンを用いて希釈し、キャノン・フェンスケにより測定した25℃における粘度が8mm2/sで、グリニャール法により測定した水酸基の量が2.2質量%のシラノール基を含有するシリコーン樹脂を得た。
得られたシリコーン樹脂を250質量部(有効成分100質量部)、
硬化触媒として(C4H9O)Al(OC(CH3)=CHCOOC2H5)2を1質量部、及び
溶剤としてメチルイソブチルケトンを150質量部
混合し、シラノール基を含有する化合物を含む硬化性成分A-1を調製した。
(CH3)(CH3O)2SiOSi(OCH3)2(CH3) 50質量部、
(CH3)2Si(OCH3)2 40質量部、及び
(C4H9O)Al(OC(CH3)=CHCOOC2H5)2 10質量部
を混合し、アルコキシ基を含有する化合物を含む硬化性成分A-2を得た。
メタクリル酸メチル(MMA)と2-ヒドロキシ-エチルメタクリレート(HEMA)のランダム共重合体(MMA/HEMA(モル比)=88/12、数平均分子量8,400、OH基含有量0.0011mol/g) 90質量部、
イソホロンジイソシアネート 10質量部、
ジオクチルスズジラウレート 0.1質量部、
テトラヒドロフラン 150質量部、及び
メチルイソブチルケトン 150質量部
を混合し、水酸基を1分子中に平均で9.7個有する化合物とイソシアネート基を2個有する化合物とを含む硬化性成分A-3を得た。
ZX-1059(日鉄ケミカル&マテリアル株式会社)(ビスフェノールA型/F型ジグリシジルエーテル、n=0体の混合物) 100質量部、
熱光酸発生剤(サンアプロ株式会社 TA-100) 1質量部、及び
酢酸ブチル 149質量部
を混合し、エポキシ基を含有する化合物を含む硬化性成分A-4を得た。
[合成例1]
乾燥空気雰囲気下、還流装置と攪拌装置を備えた200mL四つ口フラスコ中で、下記式
で表される化合物と、0.79モル%の下記式
F-Rf1-F
で表される無官能パーフルオロポリエーテル化合物(b2-1)を含む混合物(I)50.0g(Si-H基0.067mol)、CH2=CH(CH2)6Si(OCH3)316.3g(0.070mol)、m-キシレンヘキサフロライド(沸点:116℃)50.0g、塩化白金酸/ビニルシロキサン錯体のトルエン溶液0.0884g(Pt単体として2.2×10-7molを含有)を混合し、100℃で4時間攪拌した。1H-NMR及びIRでSi-H基に由来するピークが消失したのを確認した後、反応溶液を室温まで冷却した。次いで、エバポレーターで100℃/267Paの条件で2時間減圧留去を行うことで、m-キシレンヘキサフロライドと未反応のCH2=CH(CH2)6Si(OCH3)3を除去し、下記式で示される化合物(b1-1)と上記無官能パーフルオロポリエーテル化合物(b2-1)0.72モル%とを含む混合物(II-1)56.8gを得た。また、19F-NMRスペクトルでは-64ppmにm-キシレンヘキサフロライドのCF3基のピークが観測されず、m-キシレンヘキサフロライド残留量は0質量%であった。
合成例1の混合物(II-1)に、下記式の化合物(b2-2)を追加することで、(b2)に該当する成分を混合物中に合計3.0モル%含む混合物(II-2)10.2gを得た。
CF3CF2O(CF2CF2O)20.5(CF2O)22.1CF2CF3
合成例1の混合物(II-1)に、上記式の化合物(b2-2)を追加することで、(b2)に該当する成分を混合物中に合計4.8モル%含む混合物(II-3)10.4gを得た。
乾燥空気雰囲気下、還流装置と攪拌装置を備えた200mL四つ口フラスコ中で、19F-NMRにより、無官能パーフルオロポリエーテル化合物(b2)に由来するCF3-基(末端)が検出できないことを確認した下記式
で表される化合物(III)50.0g(Si-H基0.067mol)、CH2=CH(CH2)6Si(OCH3)316.3g(0.070mol)、m-キシレンヘキサフロライド50.0g、塩化白金酸/ビニルシロキサン錯体のトルエン溶液0.0884g(Pt単体として2.2×10-7molを含有)を混合し、100℃で4時間攪拌した。1H-NMR及びIRでSi-H基に由来するピークが消失したのを確認した後、反応溶液を室温まで冷却した。次いで、m-キシレンヘキサフロライドと未反応のCH2=CH(CH2)6Si(OCH3)3を除去し、(b2)成分を含まない下記式で表される化合物(IV-I)56.9gを得た。また、ヘキサフルオロベンゼンを標準物質とする19F-NMRスペクトルのm-キシレンヘキサフロライドのCF3基のピーク積分値から求めた、m-キシレンヘキサフロライド残留量は0.002質量%であった。
合成例の混合物(II-1)、(II-2)、(II-3)、化合物(IV-1)及び特開2012-233157号公報に記載の方法に従い合成した下記式で示される化合物(V)を20質量部に対して無希釈もしくは80質量部のMEKを配合して、以下の表1の表面改質成分(B1~7)を調製した。
また、合成例のII-1、II-2及び各溶剤を表2のように配合して、表面改質成分(B8~12)を調製した。
[含フッ素硬化性組成物の調製及び評価結果]
表3~8に示す配合で本発明の含フッ素硬化性組成物及び本発明に該当しない比較例を調製し、以下に示す方法で、塗工、硬化及び硬化物の評価を行った。なお含フッ素硬化性組成物を調製した時点で白濁が発生したサンプルについては、それ以上の硬化及び評価は行わなかった。
塗工硬化方法(1):
含フッ素硬化性組成物をガラス板上でギャップ24μmのワイヤーバーで塗工し、150℃で1時間静置したのち、室温まで自然冷却させて、硬化被膜を得た。
含フッ素硬化性組成物をポリカーボネート板上でギャップ12μmのワイヤーバーで塗工し、25℃の環境下で48時間静置して、硬化被膜を得た。
含フッ素硬化性組成物をガラス板上でギャップ18μmのワイヤーバーで塗工し、120℃の環境下で2時間静置したのちに、室温まで自然冷却させて、硬化被膜を得た。
含フッ素硬化性組成物をガラス板上に、3,000rpm/30秒でスピンコートし、100℃の環境下で1時間静置したのちに、室温まで自然冷却させて、硬化被膜を得た。
〔外観〕
目視により塗膜の透明性、欠損の有無を確認した。
接触角計(協和界面科学社製A3型)を用いて、液量2μLで測定した。
マジックはじき性は、ゼブラ社製 ハイマッキー黒 太字を用いて、硬化被膜表面に線を引いたときのはじき具合を目視により確認した。
指紋を付着させた後、ティッシュペーパーで拭き取った後の外観を目視で判定した。
Claims (16)
- 熱又は湿気により硬化物を与える硬化性成分(A)と、下記一般式(1)
[McRbSi-Z2]a-Q1-Z1-Rf-Z1-Q1-[Z2-SiRbMc]a (1)
(式中、Rfは数平均分子量1,500~20,000の2価パーフルオロポリエーテル基である。
Z1はそれぞれ独立に2価の連結基であり、酸素原子、窒素原子、フッ素原子又はケイ素原子を含んでいてもよく、また環状構造及び/又は不飽和結合を有する基であってもよい。
Z2はそれぞれ独立に炭素数2~20の2価の炭化水素基であり、環状構造をなしていてもよく、途中エーテル結合(-O-)を含んでいてもよい。
Q1はそれぞれ独立に(a+1)価の連結基であり、水素原子、炭素原子、酸素原子、ケイ素原子、窒素原子のいずれか2種類以上の原子を含む構造であり、環状をなしていてもよい。
aはそれぞれ独立に1~10の整数であり、bはそれぞれ独立に0~2の整数であり、cはそれぞれ独立に1~3の整数であり、かつ同一ケイ素原子上のb、cにおいてb+c=3を満たす。式(1)における[ ]で括られたa個のZ2はすべてQ1構造中のケイ素原子と結合している。
Rはそれぞれ独立に炭素数1~6の1価の炭化水素基である。
Mはそれぞれ独立に、炭素数1~10のアルコキシ基、炭素数2~10のアルコキシアルキル基、炭素数2~10のアルコキシアルコキシ基、炭素数1~10のアシロキシ基、炭素数2~10のアルケニルオキシ基及びハロゲン基からなる群より選ばれる基である。)
で示されるパーフルオロポリエーテル化合物(b1)を含む表面改質成分(B)とからなり、かつ揮発性成分を除外した硬化性成分(A)100質量部に対して、表面改質成分(B)中のパーフルオロポリエーテル化合物(b1)が0.005~50質量部である含フッ素硬化性組成物。 - 表面改質成分(B)が、さらに下記一般式(2)
F-Rf’-F (2)
(式中、Rf’は数平均分子量1,500~20,000の2価パーフルオロポリエーテル基である。)
で示される無官能パーフルオロポリエーテル化合物(b2)を、一般式(1)で示されるパーフルオロポリエーテル化合物(b1)と上記(b2)成分の合計100モル%に対して5モル%未満含み、揮発性成分を除外した硬化性成分(A)100質量部に対して、表面改質成分(B)中の(b1)成分と(b2)成分の合計が0.005~50質量部であり、かつ、常圧における沸点が260℃以下である含フッ素溶剤の含有量が(B)成分全体の1質量%未満である請求項1に記載の含フッ素硬化性組成物。 - 式(1)、(2)において、Rf及びRf’が、それぞれ以下の2価パーフルオロエーテル基群
-CF2O-
-CF2CF2O-
-CF2CF2CF2O-
-CF(CF3)CF2O-
-CF2CF2CF2CF2O-
-CF2CF2CF2CF2CF2O-
-CF2CF2CF2CF2CF2CF2O-
から選ばれる少なくとも1つの構造からなる繰り返し単位と、炭素数1~6のパーフルオロアルキレン基からなるものである請求項1又は2に記載の含フッ素硬化性組成物。 - 式(1)、(2)において、Rf及びRf’が、以下のいずれか
-CF2O(CF2O)p(CF2CF2O)qCF2-
-CF2CF2O(CF2O)p(CF2CF2O)qCF2CF2-
(式中、pは10~290の整数、qは5~170の整数、p+qは15~295の整数である。-CF2O-と-CF2CF2O-の各繰り返し単位の配列はランダムである。)
-CF(CF3)[OCF2CF(CF3)]sO(CuF2uO)v[CF(CF3)CF2O]tCF(CF3)-
-CF2CF2CF2O[CF(CF3)CF2O]tCF2CF2-
(式中、s、tは独立に1~120の整数であり、かつs+tは4~121の整数であり、uは1~6の整数であり、vは0~10の整数である。)
で示されるものである請求項1~3のいずれか1項に記載の含フッ素硬化性組成物。 - 式(1)において、Z2が以下の式
-(CH2)w-
(式中、wは2~20の整数である。)
で表されるものである請求項1~4のいずれか1項に記載の含フッ素硬化性組成物。 - 式(1)において、Q1がそれぞれ独立に少なくとも(a+1)個のケイ素原子を有するシロキサン構造、非置換又はハロゲン置換のシルアルキレン構造、シルアリーレン構造又はこれらの2種以上の組み合わせからなる(a+1)価の連結基である請求項1~5のいずれか1項に記載の含フッ素硬化性組成物。
- 式(1)において、Q1が環状シロキサン構造である請求項1~6のいずれか1項に記載の含フッ素硬化性組成物。
- 表面改質成分(B)が、さらにフッ素原子を含まない揮発性有機溶剤(b3)を(b1)成分100質量部に対して10~2,000質量部含むものである請求項1~8のいずれか1項に記載の含フッ素硬化性組成物。
- 硬化性成分(A)が、水酸基、カルボキシル基、アミノ基、エポキシ基、メルカプト基、イソシアネート基、加水分解性シリル基、シラノール基、又はカルボン酸無水物基を有する化合物から選ばれる少なくとも1種の化合物を含み、熱又は湿気により反応し硬化するものである請求項1~9のいずれか1項に記載の含フッ素硬化性組成物。
- 硬化性成分(A)が、フッ素原子を含まない加水分解性シラン化合物、加水分解性シロキサン化合物又はシラノール基含有シリコーン樹脂を含むものである請求項1~10のいずれか1項に記載の含フッ素硬化性組成物。
- 硬化性成分(A)が、テトラアルコキシシラン、トリアルコキシシラン、ジアルコキシシランの少なくとも1つもしくはこれらの部分加水分解縮合物、又は該部分加水分解縮合物の加水分解・部分縮合物を含むものである請求項1~11のいずれか1項に記載の含フッ素硬化性組成物。
- 硬化性成分(A)が、1分子中にイソシアネート基を2個以上有するフッ素原子を含まない化合物及び1分子中にヒドロキシル基を2個以上有するフッ素原子を含まない化合物を含むものである請求項1~12のいずれか1項に記載の含フッ素硬化性組成物。
- 硬化性成分(A)が、フッ素原子を含まないエポキシ化合物を含むものである請求項1~13のいずれか1項に記載の含フッ素硬化性組成物。
- 硬化物の表面の水接触角が100°以上である請求項1~14のいずれか1項に記載の含フッ素硬化性組成物。
- 請求項1~15のいずれか1項に記載の含フッ素硬化性組成物の硬化被膜を表面に有する物品。
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US20220340716A1 (en) | 2022-10-27 |
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