JP2012136588A - ポリシロキサン−n,n−ジヒドロカルビレン糖変性マルチブロックコポリマー及びその製造方法 - Google Patents
ポリシロキサン−n,n−ジヒドロカルビレン糖変性マルチブロックコポリマー及びその製造方法 Download PDFInfo
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- JP2012136588A JP2012136588A JP2010288650A JP2010288650A JP2012136588A JP 2012136588 A JP2012136588 A JP 2012136588A JP 2010288650 A JP2010288650 A JP 2010288650A JP 2010288650 A JP2010288650 A JP 2010288650A JP 2012136588 A JP2012136588 A JP 2012136588A
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- Prior art keywords
- acid
- group
- copolymer
- polysiloxane
- extract
- Prior art date
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Abstract
【解決手段】第2級アミノ基を有するポリシロキサン−ヒドロカルビレンアミノヒドロカルビレンマルチブロックコポリマーと糖酸又はその分子内脱水環化物とを反応させて、ポリシロキサン−N,N−ジヒドロカルビレン糖変性マルチブロックコポリマーを得る。
【選択図】なし
Description
Aは、それぞれ独立して、脂肪族不飽和結合を有しない一価炭化水素基を表し、
Bは、それぞれ独立して、二価炭化水素基を表し、
Gは、糖酸残基を表し、
mは1以上1000以下の数を表す)で示される単位を有するポリシロキサン−N,N−ジヒドロカルビレン糖変性マルチブロックコポリマーによって達成される。
Aは、それぞれ独立して、脂肪族不飽和結合を有しない一価炭化水素基を表し、
Bは、それぞれ独立して、二価炭化水素基を表し、
mは1以上1000以下の数を表す)で示される単位を有するポリシロキサン−ヒドロカルビレンアミノヒドロカルビレンマルチブロックコポリマー及び糖酸又はその分子内脱水環化物を反応させる、ポリシロキサン−N,N−ジヒドロカルビレン糖変性マルチブロックコポリマーの製造方法によって達成することができる。
Aは、それぞれ独立して、脂肪族不飽和結合を有しない一価炭化水素基を表し、
Bは、それぞれ独立して、二価炭化水素基を表し、
Gは、糖酸残基を表し、
mは1以上1000以下の数を表す)で示される単位を少なくとも1つ有する。
Aは、それぞれ独立して、脂肪族不飽和結合を有しない一価炭化水素基を表し、
Bは、それぞれ独立して、二価炭化水素基を表し、
mは1以上1000以下の数を表す)で示される単位を有するポリシロキサン−ヒドロカルビレンアミノヒドロカルビレンマルチブロックコポリマー及び糖酸又はその分子内脱水環化物を反応させる。
Aは、それぞれ独立して、脂肪族不飽和結合を有しない一価炭化水素基を表し、
mは1以上1000以下の数を表す)で示される両末端SiH基封鎖ポリシロキサン、及び、
下記一般式:
Cは、それぞれ独立して、脂肪族不飽和結合含有一価炭化水素基を表し、
Dは、水素原子又はトリオルガノシリル基を表す)で示される脂肪族不飽和結合を一分子中に二個有するアミン又はシリルアミンを付加反応させ、必要に応じて脱シリル化反応を行うことによって、前記ポリシロキサン−ヒドロカルビレンアミノヒドロカルビレンマルチブロックコポリマーを合成することができる。
重合度6.5の両末端SiH基封鎖ポリジメチルシロキサン80グラム(130.1ミリモル)に、白金と1,3-ジビニルテトラメチルジシロキサンとの錯体触媒を、白金金属量が反応混合物全体の10ppmになるようにして添加し、窒素雰囲気下で90℃に加熱した後ジアリルアミン13.9グラム(143.1ミリモル、Vi(ビニル基)/SiH(ケイ素原子結合水素原子)比:1.1)をゆっくり滴下しつつ90〜140℃で3時間加熱した。反応混合物のIR分析でSiH基の特性吸収が消失したことを確認した後、低沸点物を加熱減圧留去して淡黄色透明液体90.1グラム(収率96%)を得た。図1に示す29SiNMRの分析結果から、α付加とβ付加の比が約30:70である下記構造
重合度の異なる両末端SiH基封鎖ポリシロキサンを使用し、Vi/SiHを変更した以外は製造例1と同様にしてポリシロキサン−プロピレンアミノプロピレンマルチブロックコポリマーを得た。得られたポリシロキサン−プロピレンアミノプロピレンマルチブロックコポリマーを製造例1と同様に分析した。結果を表1に示す。
製造例1で合成したシリコーン部分の繰返し単位重合度が6.5であるポリシロキサン−プロピレンアミノプロピレンマルチブロックコポリマーの50%エタノール溶液に第2級アミノ基に対して1.15倍モル量のグルコノラクトンを添加し、50〜65℃で7時間加熱撹拌した。低沸点物を加熱減圧留去すると橙色透明な高粘度ポリマーが得られた。収率は98%であった。NMR、IR分析によるとこのコポリマーはポリシロキサン-N,N−ジプロピレングルコン酸アミドマルチブロックコポリマーであった。図4乃至図6に、それぞれ、実施例1で得られたポリシロキサン-N,N−ジプロピレングルコン酸アミドマルチブロックコポリマーの29SiNMR、13C-NMR及びIR吸収の分析結果を示す。
製造例2〜6で得られたポリシロキサン−プロピレンアミノプロピレンマルチブロックコポリマーを用いた以外は実施例1と同様にしてポリシロキサン-N,N−ジプロピレングルコン酸アミドマルチブロックコポリマーを得た。得られたポリシロキサン-N,N−ジプロピレングルコン酸アミドマルチブロックコポリマーを実施例1と同様に分析した。結果を表2に示す。
実施例4で得られたシリコーン重合度43のポリシロキサン−N,N−ジプロピレングルコン酸アミドマルチブロックコポリマー0.04グラム、エタノール0.03グラム、デカメチルシクロペンタシロキサン20gグラム及び水20グラムをホモディスパーを用いて3000回転で10分間撹拌した。得られたエマルジョンの24時間後の分離率は7%であった。
実施例6で得られたシリコーン重合度107のポリシロキサン−N,N−ジプロピレングルコン酸アミドマルチブロックコポリマー2gグラムとジメチルポリシロキサン( 東レ・ダウコーニング株式会社製のSH 200 C FLUID 6CS)18グラムを混合し、塩化ナトリウム:グリセリン:水=1:5:74(重量比)から成る水相混合物を5グラムずつ添加し、デンタルミキサーで36秒間混合し、全量が100グラムの油中水型エマルジョンを得た。得られた油中水型エマルジョン中の水相粒子の粒子径を、透過型顕微鏡(Nikon製 ECLIPSE 80i型)を用いて目視観察したところ、粒子径は2-5μmであった。
実施例3で得られたシリコーン重合度34のポリシロキサン−N,N−ジプロピレングルコン酸アミドマルチブロックコポリマー2gグラムとジメチルポリシロキサン( 東レ・ダウコーニング株式会社製のSH 200 C FLUID 6CS)18グラムを混合し、塩化ナトリウム:グリセリン:水=1:5:74(重量比)から成る水相混合物を5グラムずつ添加し、デンタルミキサーで36秒間混合し、全量が100グラムの油中水型エマルジョンを得た。得られた油中水型エマルジョン及び50℃で3週間保存したサンプルの粘度を、動的粘弾性試験装置を用いて測定した。測定条件は以下の通りであった。初期サンプル粘度に対する1週間保存後のサンプル粘度の保持率を百分率で求めた。同様に実施例4、実施例5の櫛型糖変性シリコーンの保持率を測定した。
サンプル厚:0.3mm
歪:100%
周波数:0.05Hzから80Hz
保持率:(50℃で1週間保存したサンプルの粘度/初期サンプルの粘度)×100(%)
実施例3で得られたシリコーン重合度34のポリシロキサン−N,N−ジプロピレングルコン酸アミドマルチブロックコポリマー2gグラムとジメチルポリシロキサン( 東レ・ダウコーニング株式会社製のSH 200 C FLUID 6CS)18グラムを混合し、塩化ナトリウム:グリセリン:水=1:5:74(重量比)から成る水相混合物を5グラムずつ添加し、デンタルミキサーで36秒間混合し、全量が100グラムの油中水型エマルジョンを得た。得られた油中水型エマルジョン及び50℃で3週間保存したサンプルの粘度を、動的粘弾性試験装置を用いて測定した。測定条件は以下の通りであった。初期サンプル粘度に対する3週間保存後のサンプル粘度の保持率を百分率で求めた。同様に実施例4、実施例5の櫛型糖変性シリコーンの保持率を測定した。
サンプル厚:0.3mm
歪:100%
周波数:0.05Hzから80Hz
保持率:(50℃で3週間保存したサンプルの粘度/初期サンプルの粘度)×100(%)
Claims (22)
- 前記Aがメチル基である、請求項1記載のコポリマー。
- 前記Bがプロピレン基である、請求項1又は2記載のコポリマー。
- 前記単位数が2〜1000である、請求項1乃至3のいずれかに記載のコポリマー。
- 前記Gがアルドノイル基又はウロノイル基である、請求項1乃至4のいずれかに記載のコポリマー。
- 前記アルドノイル基が−CO−(CHOH)l−CH2OH(lは1〜10の整数を表す)で表される、請求項5記載のコポリマー。
- 前記アルドノイル基が、リボン酸残基、アラビノン酸残基、キシロン酸残基、リキソン酸残基、アロン酸残基、アルトロン酸残基、グルコン酸基、マンノン酸残基、グロン酸残基、イドン酸残基、ガラクトン酸残基又はタロン酸残基である、請求項5又は6記載のコポリマー。
- 前記ウロノイル基が、グルクロン酸残基、イズロン酸残基、ガラクツロン酸残基又はマンヌロン酸残基である、請求項5記載のコポリマー。
- 請求項1乃至8のいずれかに記載のコポリマーを含む、水性又はエマルジョン組成物。
- 請求項1乃至8のいずれかに記載のコポリマーを含む、表面処理剤。
- 請求項1乃至8のいずれかに記載のコポリマーを含む、塗料。
- 請求項1乃至8のいずれかに記載のコポリマーを含む、化粧料。
- 請求項1乃至8のいずれかに記載のコポリマーからなる、界面活性剤。
- 前記糖酸又はその分子内脱水環化物が前記ポリシロキサン−ヒドロカルビレンアミノヒドロカルビレンマルチブロックコポリマー中の第2級アミノ基と反応する、請求項14記載の製造方法。
- 前記Aがメチル基である、請求項14又は15記載の製造方法。
- 前記糖酸がアルドン酸又はウロン酸である、請求項14乃至16のいずれかに記載の製造方法。
- 前記アルドン酸が、リボン酸、アラビノン酸、キシロン酸、リキソン酸、アロン酸、アルトロン酸、グルコン酸、マンノン酸、グロン酸、イドン酸、ガラクトン酸又はタロン酸である、請求項17記載の製造方法。
- 前記ウロン酸が、グルクロン酸、イズロン酸、ガラクツロン酸又はマンヌロン酸である、請求項17記載の製造方法。
- 前記糖酸の分子内脱水環化物がアルドノラクトン又はウロノラクトンである、請求項14乃至19のいずれかに記載の製造方法。
- 前記単位数が2〜1000である、請求項21記載の製造方法。
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- 2011-12-21 EP EP11811171.5A patent/EP2655480B1/en not_active Not-in-force
- 2011-12-21 US US13/996,356 patent/US20130317243A1/en not_active Abandoned
- 2011-12-21 WO PCT/JP2011/080546 patent/WO2012086847A2/en active Application Filing
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2019006982A (ja) * | 2017-06-23 | 2019-01-17 | 中国塗料株式会社 | 耐熱塗料組成物、耐熱塗膜、耐熱塗膜付き基材およびその製造方法 |
JP7089938B2 (ja) | 2017-06-23 | 2022-06-23 | 中国塗料株式会社 | 耐熱塗料組成物、耐熱塗膜、耐熱塗膜付き基材およびその製造方法 |
JP2020528091A (ja) * | 2017-07-19 | 2020-09-17 | ザ プロクター アンド ギャンブル カンパニーThe Procter & Gamble Company | 官能化シロキサンポリマー及びそれを含む組成物 |
US11130929B2 (en) | 2017-07-19 | 2021-09-28 | The Procter & Gamble Company | Functionalized siloxane polymers and compositions comprising same |
JP7000554B2 (ja) | 2017-07-19 | 2022-01-19 | ザ プロクター アンド ギャンブル カンパニー | 官能化シロキサンポリマー及びそれを含む組成物 |
Also Published As
Publication number | Publication date |
---|---|
WO2012086847A2 (en) | 2012-06-28 |
EP2655480A2 (en) | 2013-10-30 |
WO2012086847A3 (en) | 2012-08-23 |
US20130317243A1 (en) | 2013-11-28 |
CN103354822A (zh) | 2013-10-16 |
JP5624455B2 (ja) | 2014-11-12 |
EP2655480B1 (en) | 2014-12-10 |
KR20130131401A (ko) | 2013-12-03 |
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