JP2016069289A - ビニル基含有化合物の製造方法 - Google Patents
ビニル基含有化合物の製造方法 Download PDFInfo
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- JP2016069289A JP2016069289A JP2014197343A JP2014197343A JP2016069289A JP 2016069289 A JP2016069289 A JP 2016069289A JP 2014197343 A JP2014197343 A JP 2014197343A JP 2014197343 A JP2014197343 A JP 2014197343A JP 2016069289 A JP2016069289 A JP 2016069289A
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- 125000003277 amino group Chemical group 0.000 claims description 12
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- 230000009257 reactivity Effects 0.000 description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
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- 150000000644 6-membered heterocyclic compounds Chemical class 0.000 description 3
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
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- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本発明に係るビニル基含有化合物の製造方法は、上記一般式(3)で表される水酸基含有化合物を含む粗生成物からアルコールにより着色物質を除去して、上記水酸基含有化合物を含む精製物を得る脱色工程と、上記精製物から、上記一般式(1)で表されるビニル基含有化合物を得る反応工程とを含む。
まず、上記一般式(1)で表されるビニル基含有化合物について詳細に説明する。
上記一般式(1)において、W1及びW2は、独立に下記一般式(2)で表される基、下記一般式(4)で表される基、水酸基、又は(メタ)アクリロイルオキシ基を示し、ただし、W1及びW2は同時に水酸基でも下記一般式(4)で表される基でも(メタ)アクリロイルオキシ基でもない。W1及びW2の少なくとも一方は、下記一般式(2)で表される基であることが好ましく、W1及びW2のいずれもが下記一般式(2)で表される基であることがより好ましい。なお、本明細書において、「(メタ)アクリロイル」という用語は、アクリロイルとメタクリロイルの両方を意味する。
上記脱色工程においては、上記一般式(3)で表される水酸基含有化合物を含む粗生成物からアルコールにより着色物質を除去して、上記水酸基含有化合物を含む精製物を得る。上記一般式(3)で表される水酸基含有化合物は、単独で又は2種以上組み合わせて用いることができる。
上記反応工程においては、上記脱色工程において得た上記精製物から、上記一般式(1)で表されるビニル基含有化合物を得る。上記反応工程では、上記精製物に含まれる、上記一般式(3)で表される水酸基含有化合物を出発物質として、上記一般式(1)で表されるビニル基含有化合物が合成される。上記反応工程としては、例えば、以下の例1及び例2が挙げられる。
上記反応工程としては、例えば、遷移元素化合物触媒及び無機塩基の存在下、下記一般式(13)で表されるビニルエステル化合物と、上記精製物とを反応させることにより、上記一般式(1)で表されるビニル基含有化合物を得る反応工程が挙げられる。ここで、下記一般式(13)で表されるビニルエステル化合物は、上記精製物に含まれる、上記一般式(3)で表される水酸基含有化合物と主に反応する。より具体的には、例えば、特開2008−266169号公報に記載の製造方法に従って、上記精製物から、上記一般式(1)で表されるビニル基含有化合物を得ることができる。上記無機塩基は、粒子径150μm未満の粒子を10重量%以上含有する固体の無機塩基であることが好ましい。
R6−CO−O−CH=CH2 (13)
(式中、R6は、水素原子又は有機基を示す。)
上記反応工程としては、例えば、上記精製物から、下記一般式(5)で表される脱離基含有化合物を経由して、上記一般式(1)で表されるビニル基含有化合物を得る反応工程も挙げられる。
上述の通り、上記一般式(1)で表されるビニル基含有化合物は、組成物中の基材成分として有用である。本発明に係る製造方法により得られた上記ビニル基含有化合物を含有する組成物は着色が効果的に抑制されており、この組成物からは、透明性に優れた物体(例えば、膜や成形体)を容易に得ることができる。上記一般式(1)で表されるビニル基含有化合物を含有する組成物としては、非感光性組成物等の非感エネルギー性組成物、ネガ型感光性樹脂組成物等の感エネルギー性組成物が例示される。以下、非感光性組成物及びネガ型感光性樹脂組成物について説明する。
非感光性組成物としては、例えば、上記一般式(1)で表される化合物と、有機溶剤とを含有するものが挙げられる。有機溶剤としては、例えば、後述するネガ型感光性樹脂組成物において例示したものが挙げられる。
上述の通り、上記一般式(1)で表される化合物は、ネガ型感光性樹脂組成物の成分として有用である。ネガ型感光性樹脂組成物としては、例えば、アルカリ可溶性樹脂、光重合性モノマー、光重合開始剤、上記一般式(1)で表される化合物、及び有機溶剤を含有するものが挙げられる。以下、このネガ型感光性樹脂組成物について詳細に説明する。
なお、本明細書においてアルカリ可溶性樹脂とは、樹脂濃度20質量%の樹脂溶液(溶媒:プロピレングリコールモノメチルエーテルアセテート)により、膜厚1μmの樹脂膜を基板上に形成し、2.38質量%のテトラメチルアンモニウムヒドロキシド(TMAH)水溶液に1分間浸漬した際に、膜厚0.01μm以上溶解するものをいう。
また、上記一般式(r−1)中、kは、0〜20の整数を示す。
なお、本明細書において、「(メタ)アクリル酸」は、アクリル酸とメタクリル酸との両方を意味する。同様に、「(メタ)アクリレート」は、アクリレートとメタクリレートとの両方を意味する。更に、「(メタ)アクリルアミド」は、アクリルアミドとメタクリルアミドとの両方を意味する。
単官能モノマーとしては、(メタ)アクリルアミド、メチロール(メタ)アクリルアミド、メトキシメチル(メタ)アクリルアミド、エトキシメチル(メタ)アクリルアミド、プロポキシメチル(メタ)アクリルアミド、ブトキシメトキシメチル(メタ)アクリルアミド、N−メチロール(メタ)アクリルアミド、N−ヒドロキシメチル(メタ)アクリルアミド、(メタ)アクリル酸、フマル酸、マレイン酸、無水マレイン酸、イタコン酸、無水イタコン酸、シトラコン酸、無水シトラコン酸、クロトン酸、2−アクリルアミド−2−メチルプロパンスルホン酸、tert−ブチルアクリルアミドスルホン酸、メチル(メタ)アクリレート、エチル(メタ)アクリレート、ブチル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシブチル(メタ)アクリレート、2−フェノキシ−2−ヒドロキシプロピル(メタ)アクリレート、2−(メタ)アクリロイルオキシ−2−ヒドロキシプロピルフタレート、グリセリンモノ(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、ジメチルアミノ(メタ)アクリレート、グリシジル(メタ)アクリレート、2,2,2−トリフルオロエチル(メタ)アクリレート、2,2,3,3−テトラフルオロプロピル(メタ)アクリレート、フタル酸誘導体のハーフ(メタ)アクリレート等が挙げられる。これらの単官能モノマーは、単独又は2種以上組み合わせて用いることができる。
C.I.ピグメントオレンジ1(以下、「C.I.ピグメントオレンジ」は同様であり、番号のみを記載する。)、5、13、14、16、17、24、34、36、38、40、43、46、49、51、55、59、61、63、64、71、73;
C.I.ピグメントバイオレット1(以下、「C.I.ピグメントバイオレット」は同様であり、番号のみを記載する。)、19、23、29、30、32、36、37、38、39、40、50;
C.I.ピグメントレッド1(以下、「C.I.ピグメントレッド」は同様であり、番号のみを記載する。)、2、3、4、5、6、7、8、9、10、11、12、14、15、16、17、18、19、21、22、23、30、31、32、37、38、40、41、42、48:1、48:2、48:3、48:4、49:1、49:2、50:1、52:1、53:1、57、57:1、57:2、58:2、58:4、60:1、63:1、63:2、64:1、81:1、83、88、90:1、97、101、102、104、105、106、108、112、113、114、122、123、144、146、149、150、151、155、166、168、170、171、172、174、175、176、177、178、179、180、185、187、188、190、192、193、194、202、206、207、208、209、215、216、217、220、223、224、226、227、228、240、242、243、245、254、255、264、265;
C.I.ピグメントブルー1(以下、「C.I.ピグメントブルー」は同様であり、番号のみを記載する。)、2、15、15:3、15:4、15:6、16、22、60、64、66;
C.I.ピグメントグリーン7、C.I.ピグメントグリーン36、C.I.ピグメントグリーン37;
C.I.ピグメントブラウン23、C.I.ピグメントブラウン25、C.I.ピグメントブラウン26、C.I.ピグメントブラウン28;
C.I.ピグメントブラック1、C.I.ピグメントブラック7。
特に、ネガ型感光性樹脂組成物を使用してブラックマトリクスを形成する場合には、ブラックマトリクスの膜厚1μm当たりのOD値が4以上となるように、ネガ型感光性樹脂組成物における遮光剤の量を調整することが好ましい。ブラックマトリクスにおける膜厚1μm当たりのOD値が4以上あれば、液晶表示ディスプレイのブラックマトリクスに用いた場合に、十分な表示コントラストを得ることができる。
6,6−(9−フルオレニリデン)−2,2−ジナフトール(下記左側の式で表される化合物。以下、化合物2ともいう。)の粗生成物の着色粉末(10g)をエタノール(90mL)に撹拌下で添加したところ、上記粉末はエタノールに溶解したが、その後に経時で白色沈殿が析出した。この白色沈殿を濾集して化合物2の精製物を得た。なお、濾液(エタノール相)は着色しており、化合物2の粗生成物に含まれていた着色物質がエタノールに溶解した状態で除去されたことが確認された。
エタノールの代わりにアセトニトリルを用いた以外は、精製例1と同様にして精製操作を行ったところ、化合物2の粗生成物は溶解したが、その後に経時で析出する沈殿物は着色しており、着色物質が除去されなかった。
エタノールの代わりにテトラヒドロフランを用いた以外は、精製例1と同様にして精製操作を行ったところ、化合物2の粗生成物は溶解したが、その後に経時で析出する沈殿物の量が微量であり、また、析出する沈殿物は着色しており、着色物質が除去されなかった。
25mL反応器にエチレングリコール(1.00g、0.0161mol)、トリエチルアミン(3.42g0.0338mol)、テトラヒドロフラン(3.38mL)を加え、窒素置換した後に、0℃まで冷却した。メタンスルホニルクロライド(3.88g,0.0338mol)を2時間かけて滴下し、1時間熟成後、水を加えて反応を停止した。ここに酢酸エチルを添加し、有機層を分離し、エバポレーターで溶媒を留去することによって、収率80%で、エチレングリコールにメタンスルホニル基が付加した化合物(下記式で表される化合物。以下、「EG−DMs」ともいう。)を得た。
(EG−DMs)1H−NMR(CDCl3):3.10(s、6H)、4.47(s、4H)
25mL反応器に化合物2の精製物(1.00g、0.0022mol)、炭酸カリウム(0.64g,0.0047mol)、テトラヒドロフラン(3.38mL)を加え、窒素置換した。ここに、合成例1で合成したEG−DMs(1.02g,0.0047mol)のテトラヒドロフラン(1.12mL)溶液を室温で添加後、60℃まで昇温し、15時間熟成した。反応液をHPLCで分析した結果、化合物2の転化率99%、選択率65%で化合物3(下記右側の式で表される化合物)が合成されたことを確認した。
(化合物3)1H−NMR(CDCl3):3.08(s、6H)、4.32(t、4H、J=4.4Hz)、4.60(t、4H、J=4.4Hz)、7.05−7.83(m、20H)
化合物3(2.00g、0.00288mol),ジプロピレングリコールジメチルエーテル(2.25mL)を仕込んだ25mL反応器に、カリウム−t−ブトキシド(1.45g,0.0130mol)のテトラヒドロフラン(2.25mL)溶液を20℃〜40℃の範囲で滴下し、100℃で2時間熟成した。反応液をHPLCで分析した結果、化合物3の転化率99%にて、選択率58%で9,9’−ビス(6−ビニルオキシ−2−ナフチル)フルオレン(下記左側の式で表される化合物。以下、化合物1ともいう。)が合成され、選択率32%でモノビニルモノメシル体(下記右側の式で表される化合物。以下、化合物4ともいう。)が合成されたことを確認した。
(化合物1)1H−NMR(CDCl3):4.48(dd、2H、J=1.5Hz、6.5Hz)、4.81(dd、2H、J=1.5Hz、13.5Hz)、6.73(dd、2H、J=6.5Hz、13.5Hz)、7.13−7.83(m、20H)
(化合物4)1H−NMR(CDCl3):3.10(s、3H)、4.34(t、2H、J=3.6Hz)、4.49(dd、1H、J=1.2Hz、5.2Hz)、4.62(t、2H、J=3.6Hz)、4.81(dd、1H、J=1.2Hz、11.2Hz)、6.73(dd、1H、J=5.2Hz、11.2Hz)、7.06−7.83(m、20H)
合成例3で得られた反応液を、水で洗浄した後に、加熱減圧下で乾燥し、残留物をトルエンに溶解し、メタノールへ滴下して再沈殿を行い、化合物1の粗生成物を得た。HPLCによる分析の結果、この粗生成物において、化合物1の含有量は90.9質量%であった。
合成例4で得た粗生成物をシリカゲルカラムクロマトグラフィーに供して分離精製を実施し、化合物1の精製物を得た。HPLCによる分析の結果、この精製物において、化合物1の含有量は98.7質量%であった。
合成例2において、化合物2の精製物の代わりに化合物2の粗生成物(着色粉末、1.00g、0.0022mol)を用いた以外は、合成例1〜5と同様にして、化合物1の精製物を得た。
目視により観察したところ、合成例1〜5で得られた化合物1は白色粉末であったが、比較合成例1で得られた化合物1は赤色粉末であった。この結果から、化合物2の粗生成物からエタノールにより着色物質を除去することで、上記一般式(1)で表されるビニル基含有化合物である化合物1を白色粉末として得ることができることが確認された。
上記で得られた化合物1をプロピレングリコールモノメチルエーテルアセテートに溶解して20質量%の溶液を調製した。この溶液をガラス基板にスピンコーターを用いて塗布し、100℃で120秒間プリベークを行い、乾燥塗膜を形成した。この乾燥塗膜を230℃で20分間焼成して、焼成膜(膜厚2.0μm)を得た。得られた焼成膜の400nmにおける光透過率を測定したところ、合成例1〜5で得られた化合物1由来の焼成膜については、光透過率が95%以上であった。これに対し、比較合成例1で得られた化合物1由来の焼成膜については、光透過率が90%以下であった。この結果から、化合物2の粗生成物からエタノールにより着色物質を除去して得た化合物2の精製物由来の化合物1からは、透明性に優れる膜を得ることができることが確認された。
上記で得られた化合物1をプロピレングリコールモノメチルエーテルアセテートに溶解して20質量%の溶液を調製した。この溶液をシリコーン基板にスピンコーターを用いて塗布し、100℃で120秒間プリベークを行い、乾燥塗膜を形成した。この乾燥塗膜を230℃で20分間焼成して、焼成膜(膜厚0.25μm)を得た。屈折率計を用いて、得られた焼成膜の波長633nmでの屈折率を測定したところ、合成例1〜5で得られた化合物1由来の焼成膜及び比較合成例1で得られた化合物1由来の焼成膜のいずれについても、屈折率は1.74であった。
Claims (5)
- 下記一般式(3)で表される水酸基含有化合物を含む粗生成物からアルコールにより着色物質を除去して、前記水酸基含有化合物を含む精製物を得る脱色工程と、
前記精製物から、下記一般式(1)で表されるビニル基含有化合物を得る反応工程とを含むビニル基含有化合物の製造方法。
- 前記反応工程は、遷移元素化合物触媒及び無機塩基の存在下、下記一般式(13)で表されるビニルエステル化合物と、前記精製物とを反応させることにより、上記一般式(1)で表されるビニル基含有化合物を得る反応工程である請求項1に記載のビニル基含有化合物の製造方法。
R6−CO−O−CH=CH2 (13)
(式中、R6は、水素原子又は有機基を示す。) - 前記反応工程は、前記精製物から、下記一般式(5)で表される脱離基含有化合物を経由して、上記一般式(1)で表されるビニル基含有化合物を得る反応工程である請求項1に記載のビニル基含有化合物の製造方法。
- 前記環Zがベンゼン環又はナフタレン環である請求項1から3のいずれか1項に記載のビニル基含有化合物の製造方法。
- 前記R1が単結合である請求項1から4のいずれか1項に記載のビニル基含有化合物の製造方法。
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002363119A (ja) * | 2001-04-24 | 2002-12-18 | Ferrania Spa | 高純度9.9−ビス−(ヒドロキシフェニル)−フルオレンならびにその調製および精製方法 |
CN1939900A (zh) * | 2005-09-26 | 2007-04-04 | 中国科学院广州化学研究所 | 2,7-二磺酸基-9,9-二(4-羟基苯基)芴及其制备方法 |
JP2013028574A (ja) * | 2011-07-29 | 2013-02-07 | Maruzen Petrochem Co Ltd | 芳香族ビニルエーテルの製造方法 |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002363119A (ja) * | 2001-04-24 | 2002-12-18 | Ferrania Spa | 高純度9.9−ビス−(ヒドロキシフェニル)−フルオレンならびにその調製および精製方法 |
CN1939900A (zh) * | 2005-09-26 | 2007-04-04 | 中国科学院广州化学研究所 | 2,7-二磺酸基-9,9-二(4-羟基苯基)芴及其制备方法 |
JP2013028574A (ja) * | 2011-07-29 | 2013-02-07 | Maruzen Petrochem Co Ltd | 芳香族ビニルエーテルの製造方法 |
Non-Patent Citations (1)
Title |
---|
HIRABAYASHI, TOMOTAKA ET AL.: "Iridium-catalyzed synthesis of vinyl ethers from alcohols and vinyl acetate", ORGANIC SYNTHESES, vol. (2005), 82, 55-58, JPN6018011897, 2005, ISSN: 0003771504 * |
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