JP6092545B2 - カルボシロキサンデンドリマー構造および親水性基を有する共重合体およびその用途 - Google Patents
カルボシロキサンデンドリマー構造および親水性基を有する共重合体およびその用途 Download PDFInfo
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- JP6092545B2 JP6092545B2 JP2012182828A JP2012182828A JP6092545B2 JP 6092545 B2 JP6092545 B2 JP 6092545B2 JP 2012182828 A JP2012182828 A JP 2012182828A JP 2012182828 A JP2012182828 A JP 2012182828A JP 6092545 B2 JP6092545 B2 JP 6092545B2
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Landscapes
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Description
Zは、2価の有機基であり、
pは、0又は1であり、
R1及びR2は、それぞれ独立して、炭素原子数1〜10のアルキル基、アリール基又はアラルキル基であり、
L1は、i=1とした場合の下記式(2)で示されるシリルアルキル基
Z及びpは、前記と同じであり、
R1及びR2は、前記と同じであり、
iは、前記シリルアルキル基の総階層数を示す1〜10の整数であり、
Li+1は、水素原子、炭素原子数1〜10のアルキル基、アリール基、アラルキル基及び前記シリルアルキル基からなる群から選択される基であり、但し、i=c(cは前記シリルアルキル基の階層を示す1〜10の整数である)の場合は、Li+1は水素原子、炭素原子数1〜10のアルキル基、アリール基又はアラルキル基であり、i<cの場合は前記シリルアルキル基であり、
aiは0〜3の整数である)である}で示されるカルボシロキサンデンドリマー構造を有する不飽和単量体、及び
(B)分子中に少なくとも1つの親水性基を有する不飽和単量体を含有してなり、
上記のカルボシロキサンデンドリマー構造を有する不飽和単量体が全モノマー単位の35〜50質量%の範囲である共重合体によって達成される。
(B)分子中に少なくとも1つの親水性基を有する不飽和単量体 および
(C)分子中に少なくとも1つのフッ素含有有機基を有する不飽和単量体を
{(A)成分の質量/全単量体の質量}:{(B)成分の質量/全単量体の質量}:{(C)成分の質量/全単量体の質量}が、[0.35〜0.50:0.01〜0.40:0.00〜0.60]の範囲であり、かつ{(A)成分の質量/全単量体の質量}≧{(B)成分の質量/全単量体の質量}の条件を満たす質量比で共重合して得られる共重合体により、より良く上記課題を解決できることを見出し、本発明に到達した。
(B1)分子中に少なくとも1つの一価または多価アルコール性水酸基を有する不飽和単量体 および
(C1)一般式:CH2=CR15COORfで表される不飽和単量体(式中、R15は水素原子又はメチル基であり、Rfはフルオロアルキル基またはフルオロアルキルオキシフルオロアルキレン基である)を
{(A)成分の質量/全単量体の質量}:{(B)成分の質量/全単量体の質量}:{(C1)成分の質量/全単量体の質量}が、[0.35〜0.50:0.10〜0.40:0.10〜0.50]の範囲であり、かつ{(A)成分の質量/全単量体の質量}≧{(B)成分の質量/全単量体の質量}の条件を満たす質量比で共重合して得られる共重合体により、特に良く上記課題を解決できることを見出し、本発明に到達した。
Zは、2価の有機基であり、
pは、0又は1であり、
R1及びR2は、それぞれ独立して、炭素原子数1〜10のアルキル基、アリール基又はアラルキル基であり、
L1は、i=1とした場合の下記式(2)で示されるシリルアルキル基
Z及びpは、前記と同じであり、
R1及びR2は、前記と同じであり、
iは、前記シリルアルキル基の総階層数を示す1〜10の整数であり、1〜5が好ましく、1〜3が更により好ましく、1又は2が更により好ましく、
Li+1は、水素原子、炭素原子数1〜10のアルキル基、アリール基、アラルキル基及び前記シリルアルキル基からなる群から選択される基であり、但し、i=c(cは前記シリルアルキル基の階層を示す1〜10の整数であり、1〜5が好ましく、1〜3が更により好ましく、1又は2が更により好ましい)の場合は、Li+1は水素原子、炭素原子数1〜10のアルキル基、アリール基又はアラルキル基であり、i<cの場合は前記シリルアルキル基であり、
aiは、0〜3の整数であり、好ましくは0〜2であり、より好ましくは0〜1であり、更により好ましくは0である)である}で示されるカルボシロキサンデンドリマー構造を有する重合体、及び
(B)分子中に少なくとも1つの親水性基を有する不飽和単量体を含有してなり、
上記のカルボシロキサンデンドリマー構造を有する不飽和単量体が全モノマー単位の35〜50質量%の範囲である共重合体である。さらに、本発明の新規共重合体は、(C)分子中に少なくとも1つのフッ素含有有機基を有する不飽和単量体を含有してなる共重合体であることが好ましい。
R3は、炭素原子数1〜30の、置換又は非置換の、及び、直鎖状又は分岐状の前記二価炭化水素基であり、既述したとおり、置換基を有していてもよく、
R3’は、下記式
から選択される基であってもよい。ケイ素原子結合水素原子及びアルケニル基の反応により導入可能な一般式−R3−又は−R3−R3’−で示される2価の有機基が好ましい。同様に、ケイ素原子結合水素原子及び不飽和カルボン酸官能基の反応により導入可能な一般式−R3−COO−R3−又は−R3−COO−R3’−で示される2価の有機基も好適である。
Yはラジカル重合可能な不飽和含有基であり、
Z、p、R1、R2、L1及びaiは前記と同じである)
で表される。
CH2=CCH3COO-CF3、CH2=CCH3COO-C2F5、CH2=CCH3COO-nC3F7、CH2=CCH3COO-CF(CF3)2、CH2=CCH3COO-nC4F9、CH2=CCH3COO-CF2CF(CF3)2、CH2=CCH3COO-nC5F11、CH2=CCH3COO-nC6F13、CH2=CCH3COO-nC8F17、CH2=CCH3COO-CH2CF3、CH2=CCH3COO-CH(CF3)2、CH2=CCH3COO-CH2CH(CF3)2、CH2=CCH3COO-CH2(CF2)2F、CH2=CCH3COO-CH2(CF2)3F、CH2=CCH3COO-CH2(CF2)4F、CH2=CCH3COO-CH2(CF2)6F、CH2=CCH3COO-CH2(CF2)8F、CH2=CCH3COO-CH2CH2CF3、CH2=CCH3COO-CH2CH2(CF2)2F、CH2=CCH3COO-CH2CH2(CF2)3F、CH2=CCH3COO-CH2CH2(CF2)4F、CH2=CCH3COO-CH2CH2(CF2)6F、CH2=CCH3COO-CH2CH2(CF2)8F、CH2=CCH3COO-CH2CH2(CF2)10F 、CH2=CCH3COO-CH2CH2(CF2)12F 、CH2=CCH3COO-CH2CH2(CF2)14F 、CH2=CCH3COO-CH2CH2(CF2)16F 、CH2=CCH3COO-CH2CH2CH2CF3 、CH2=CCH3COO-CH2CH2CH2(CF2)2F 、CH2=CCH3COO-CH2CH2CH2(CF2)2H 、CH2=CCH3COO-CH2(CF2)4H 、CH2=CCH3COO-CH2CH2(CF2)3H、CH2=CCH3COO-CH2CH2CF(CF3)-[OCF2CF(CF3)]z-OC3F7、CH2=CCH3COO-CH2CH2CF2CF2-[OCF2CF(CF3)]z-OC3F7CH2=CHCOO-CF3、CH2=CHCOO-C2F5、CH2=CHCOO-nC3F7、CH2=CHCOO-CF(CF3)2、CH2=CHCOO-nC4F9、CH2=CHCOO-CF2CF(CF3)2、CH2=CHCOO-nC5F11、CH2=CHCOO-nC6F13、CH2=CHCOO-nC8F17、CH2=CHCOO-CH2CF3、CH2=CHCOO-CH(CF3)2、CH2=CHCOO-CH2CH(CF3)2、CH2=CHCOO-CH2(CF2)2F、CH2=CHCOO-CH2(CF2)3F、CH2=CHCOO-CH2(CF2)4F、CH2=CHCOO-CH2(CF2)6F、CH2=CHCOO-CH2(CF2)8F、CH2=CHCOO-CH2CH2CF3、CH2=CHCOO-CH2CH2(CF2)2F、CH2=CHCOO-CH2CH2(CF2)3F、CH2=CHCOO-CH2CH2(CF2)4F、CH2=CHCOO-CH2CH2(CF2)6F、CH2=CHCOO-CH2CH2(CF2)8F、CH2=CHCOO-CH2CH2(CF2)10F 、CH2=CHCOO-CH2CH2(CF2)12F 、CH2=CHCOO-CH2CH2(CF2)14F 、CH2=CHCOO-CH2CH2(CF2)16F 、CH2=CHCOO-CH2CH2CH2CF3 、CH2=CHCOO-CH2CH2CH2(CF2)2F 、CH2=CHCOO-CH2CH2CH2(CF2)2H 、CH2=CHCOO-CH2(CF2)4H 、CH2=CHCOO-CH2CH2(CF2)3H、CH2=CHCOO-CH2CH2CF(CF3)-[OCF2CF(CF3)]z-OC3F7、CH2=CHCOO-CH2CH2CF2CF2-[OCF2CF(CF3)]z-OC3F7。これらの中でも、下記式で示されるビニル単量体が好ましい。CH2=CHCOO-CH2CH2(CF2)6F、CH2=CHCOO-CH2CH2(CF2)8F、CH2=CCH3COO-CH2CH2(CF2)6F、CH2=CCH3COO-CH2CH2(CF2)8F、CH2=CHCOO-CH2CF3、CH2=CCH3COO-CH2CF3。特に、下記式で示されるビニル単量体がより好ましい。CH2=CHCOO-CH2CF3、CH2=CCH3COO-CH2CF3。
R9は、水素原子、水酸基、或いは、炭素原子数1〜30の、一価の非置換若しくはフッ素若しくはアミノ置換アルキル基、アリール基、アルコキシ基及び(CH3)3SiO{(CH3)2SiO}lSi(CH3)2CH2CH2-(lは0〜1000の整数)で示される基から選択される基であり、
a’は、0〜3の整数であり、
bは、0〜1000の整数であり、
cは、0〜1000の整数であり、但し、1≦b+c≦2000である)
R9は、上記と同様であり、
dは、0〜8の整数であり、
eは、0〜8の整数であり、但し、3≦d+e≦8である)
R9は、上記と同様であり、
fは1〜4の整数であり、
gは0〜500の整数である)
で表されるオルガノポリシロキサン
を使用することができる。
攪拌装置,温度計,還流管を取り付けた500ミリリットル4つ口フラスコに、イソプロピルアルコール(IPA)を100g仕込み、窒素ガスでバブリングを行い十分に脱気し、80℃に加熱した。滴下ロートにメチルメタクリレート25g、2-エチルヘキシルアクリレート 10g、ヒドロキシエチルメタクリレート20g、下記式(A):
滴下ロートにメチルメタクリレート18g、2-エチルヘキシルアクリレート 7g、ヒドロキシエチルメタクリレート30g、式(A)で示されるカルボシロキサンデンドリマーモノマー45gおよび2,2’−アゾビス−2−メチルブチロニトリル(大塚化学製)1.0gを仕込む組成に変更した以外は、実施例1と同様な操作を行い、ビニル重合体のデカメチルペンタシロキサン溶液を得た。本重合体の重量平均分子量は、12800であり、Mw/Mnは2.24であった。
滴下ロートにメタクリル酸2−エチルヘキシル32g、2-エチルヘキシルアクリレート 5g、メタクリル酸グリセリル 18g、式(A)で示されるカルボシロキサンデンドリマーモノマー45gおよび2,2’−アゾビス−2−メチルブチロニトリル(大塚化学製)1.0gを仕込む組成に変更した以外は、実施例1と同様な操作を行い、ビニル重合体のデカメチルペンタシロキサン溶液を得た。
滴下ロートにメタクリル酸トリフルオロエチル 20g、2-エチルヘキシルアクリレート 5g、メタクリル酸ヒドロキシエチル 30g、式(A)で示されるカルボシロキサンデンドリマーモノマー45gおよび2,2’−アゾビス−2−メチルブチロニトリル(大塚化学製)1.0gを仕込む組成に変更した以外は、実施例1と同様な操作を行い、ビニル重合体のデカメチルペンタシロキサン溶液を得た。本重合体の重量平均分子量は、9300であり、Mw/Mnは4.65であった。
滴下ロートにメタクリル酸トリフルオロエチル 16g、2-エチルヘキシルアクリレート 4g、メタクリル酸ヒドロキシエチル 35g、式(A)で示されるカルボシロキサンデンドリマーモノマー45gおよび2,2’−アゾビス−2−メチルブチロニトリル(大塚化学製)1.0gを仕込む組成に変更した以外は、実施例1と同様な操作を行い、ビニル重合体のデカメチルペンタシロキサン溶液を得た。
滴下ロートにメタクリル酸メチル 42g、2-エチルヘキシルアクリレート 10g、メタクリル酸ヒドロキシエチル 3g、式(A)で示されるカルボシロキサンデンドリマーモノマー45gおよび2,2’−アゾビス−2−メチルブチロニトリル(大塚化学製)1.0gを仕込む組成に変更した以外は、実施例1と同様な操作を行い、ビニル重合体のデカメチルペンタシロキサン溶液を得た。本重合体の重量平均分子量は、73300であり、Mw/Mnは3.35であった。
滴下ロートにメタクリル酸メチル 35g、2-エチルヘキシルアクリレート 10g、メタクリル酸ヒドロキシエチル 10g、式(A)で示されるカルボシロキサンデンドリマーモノマー45gおよび2,2’−アゾビス−2−メチルブチロニトリル(大塚化学製)1.0gを仕込む組成に変更した以外は、実施例1と同様な操作を行い、ビニル重合体のデカメチルペンタシロキサン溶液を得た。本重合体の重量平均分子量は、71400であり、Mw/Mnは3.13であった。
滴下ロートにトリフルオロエチルメタクリレート32g、2-エチルヘキシルアクリレート 5g、メタクリル酸グリセリル18g、式(A)で示されるカルボシロキサンデンドリマーモノマー45gおよび2,2’−アゾビス−2−メチルブチロニトリル(大塚化学製)1.0gを仕込む組成に変更した以外は、実施例1と同様な操作を行い、ビニル重合体のデカメチルペンタシロキサン溶液を得た。本重合体の重量平均分子量は、6080であり、Mw/Mnは3.38であった。
滴下ロートにメタクリル酸メチル 36g、2-エチルヘキシルアクリレート 14g、ビニルアセトアミド 5g、式(A)で示されるカルボシロキサンデンドリマーモノマー45gおよび2,2’−アゾビス−2−メチルブチロニトリル(大塚化学製)1.0gを仕込む組成に変更した以外は、実施例1と同様な操作を行い、ビニル重合体のデカメチルペンタシロキサン溶液を得た。本重合体の重量平均分子量は、79000であり、Mw/Mnは3.35であった。
滴下ロートにメタクリル酸メチル 25g、2-エチルヘキシルアクリレート 25g、ビニルアセトアミド 5g、式(A)で示されるカルボシロキサンデンドリマーモノマー45gおよび2,2’−アゾビス−2−メチルブチロニトリル(大塚化学製)1.0gを仕込む組成に変更した以外は、実施例1と同様な操作を行い、ビニル重合体のデカメチルペンタシロキサン溶液を得た。本重合体の重量平均分子量は、91100であり、Mw/Mnは4.07であった。
シリコーン処理顔料級酸化チタン(大東化成製)12g、実施例記載の分散剤1g、デカメチルペンタシロキサン 7gをディスパーを用いて混合し、E−型回転粘度計を用いて粘度を測定し、分散性を評価し、表1に示した。評価基準は次の通りである。また、比較例3として、分散剤として、東レ・ダウコーニング社製のFA 4001 CM Silicone Acrylate(表中、「FA4001CM」と略記)を用いた評価結果を示した。
評価基準
◎:粘度が350cp以下
○:350〜600cp
△:600cp以上
シリコーン処理微粒子酸化チタン(テイカ製)12g、実施例記載の分散剤3g、デカメチルペンタシロキサン 15gをディスパーを用いて混合し、ジルコニアビーズ(0.8mm)を添加して、ペイントシェーカーを用いて分散させた。分散後、ジルコニアビーズをろ別して、E−型回転粘度計を用いて粘度を測定し、分散性を評価した。評価基準は次の通りである。また、比較例3として、分散剤として、東レ・ダウコーニング社製のFA 4001 CM Silicone Acrylate(表中、「FA4001CM」と略記)を用いた評価結果を示した。
評価基準
◎:1500cp以下
○:1501〜5000cp
×:ゲル化
Claims (3)
- (A)下記式(1):
Zは、2価の有機基であり、
pは、0又は1であり、
R1及びR2は、それぞれ独立して、炭素原子数1〜10のアルキル基、アリール基又はアラルキル基であり、
L1は、i=1とした場合の下記式(2)で示されるシリルアルキル基
Z及びpは、前記と同じであり、
R1及びR2は、前記と同じであり、
iは、前記シリルアルキル基の総階層数を示す1〜10の整数であり、
Li+1は、水素原子、炭素原子数1〜10のアルキル基、アリール基、アラルキル基及び前記シリルアルキル基からなる群から選択される基であり、但し、i=c(cは前記シリルアルキル基の階層を示す1〜10の整数である)の場合は、Li+1は水素原子、炭素原子数1〜10のアルキル基、アリール基又はアラルキル基であり、i<cの場合は前記シリルアルキル基であり、
aiは0〜3の整数である)である}で示されるカルボシロキサンデンドリマー構造を有する不飽和単量体、
(B1)分子中に少なくとも1つの一価または多価アルコール性水酸基を有する不飽和単量体 および
(C1)一般式:CH2=CR15COORfで表される不飽和単量体(式中、R15は水素原子又はメチル基であり、Rfはフルオロアルキル基またはフルオロアルキルオキシフルオロアルキレン基である)を
{(A)成分の質量/全単量体の質量}:{(B1)成分の質量/全単量体の質量}:{(C1)成分の質量/全単量体の質量}が、[0.35〜0.50:0.10〜0.40:0.10〜0.50]の範囲であり、かつ{(A)成分の質量/全単量体の質量}≧{(B)成分の質量/全単量体の質量}の条件を満たす質量比で共重合して得られる共重合体 100質量部
(D)シリコーンオイル 50〜500質量部
を含有してなる液状組成物を含有する化粧料原料。 - さらに、(E)1種類以上の粉体または着色剤を含有してなる、請求項1の化粧料原料。
- 前記粉体が、(E1)撥水化処理粉体または着色剤である、請求項2の化粧料原料。
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JP2012182828A JP6092545B2 (ja) | 2012-08-22 | 2012-08-22 | カルボシロキサンデンドリマー構造および親水性基を有する共重合体およびその用途 |
PCT/JP2013/073069 WO2014030770A2 (en) | 2012-08-22 | 2013-08-22 | Copolymer having carbosiloxane dendrimer structure and hydrophilic group |
CN201380051981.6A CN104684541B (zh) | 2012-08-22 | 2013-08-22 | 具有碳硅氧烷树枝状结构和亲水性基团的共聚物 |
US14/422,773 US9670301B2 (en) | 2012-08-22 | 2013-08-22 | Copolymer having carbosiloxane dendrimer structure and hydrophilic group |
EP13760119.1A EP2887920B1 (en) | 2012-08-22 | 2013-08-22 | Copolymer having carbosiloxane dendrimer structure and hydrophilic group |
KR1020157006720A KR102121175B1 (ko) | 2012-08-22 | 2013-08-22 | 카르보실록산 덴드리머 구조 및 친수성 기를 갖는 공중합체 |
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