JP6515199B2 - 高分子 - Google Patents
高分子 Download PDFInfo
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- JP6515199B2 JP6515199B2 JP2017550450A JP2017550450A JP6515199B2 JP 6515199 B2 JP6515199 B2 JP 6515199B2 JP 2017550450 A JP2017550450 A JP 2017550450A JP 2017550450 A JP2017550450 A JP 2017550450A JP 6515199 B2 JP6515199 B2 JP 6515199B2
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- 239000000178 monomer Substances 0.000 claims description 130
- 229920000642 polymer Polymers 0.000 claims description 119
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 238000006116 polymerization reaction Methods 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 40
- 239000000126 substance Substances 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 33
- -1 acryloyloxy group Chemical group 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 24
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 23
- 229920002554 vinyl polymer Polymers 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 description 2
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- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
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Description
本出願は、高分子、その製造方法及びその高分子の用途に関する。
実施例又は比較例で製造された高分子溶液を約150℃の温度で約60分間維持し、溶媒を揮発させた。次に、溶媒を揮発させた高分子1gを採取する。次に、前記採取された1gの高分子を溶媒(ヘキサン、エチルアセテート、アセトン又は水)5gに入れ、常温で30分間撹拌した後、溶解されない残留高分子を除去した。残留高分子が除去された透明な溶液を分取し、150℃で30分間乾燥させて溶媒を除去し、質量比較を通じて固形分の含量を計算した。固形分の含量を通じて溶媒内にとけている高分子の濃度を測定して、その測定された羊を100gの溶媒に対する数値に換算して溶解度を求めた。残留高分子の除去後にも、溶液が透明でない場合、溶液をフィルター(0.45μm NYLON)に通過させて透明な溶液を得た後、前記過程を行った。
〈溶解度評価基準〉
A:溶解度が15以上の場合
B:溶解度が10超過且つ15未満の場合
C:溶解度が5超過且つ10以下の場合
D:溶解度が5以下の場合
重量平均分子量(Mw)及び分子量分布(PDI)は、GPCを使用して以下の条件で測定し、検量線の製作には、Agilent systemの標準ポリスチレンを使用して測定結果を換算した。
〈測定条件〉
測定器:Agilent GPC(Agilent 1200 series、U.S.)
カラム:PL Mixed B 2個 連結
カラム温度:40℃
溶離液:THF(Tetrahydrofuran)
流速:1.0mL/min
濃度:〜1mg/mL(100μL injection)
ガラス転移温度(Tg)は、単量体の組成によって下記数式に基づいて算出した。
〈数式〉
1/Tg=ΣWn/Tn
前記数式で、Wnは、高分子の各単量体の重量分率であり、Tnは、単量体が単独重合体を形成した場合に現われるガラス転移温度であり、前記数式の右辺は、使用された単量体の重量分率を、その単量体が単独重合体を形成した場合に示すガラス転移温度で分けた数値(Wn/Tn)を単量体別に計算した後、計算された数値をすべて合算した結果である。
溶媒としてイソドデカン(isododecane)に各製造例で製造された高分子を約10重量%の濃度で溶解させ、セレシン(ceresine)、合成ワックス(synthetic wax)及びマイクロクリスタルワックス(microcrystanlline wax)をそれぞれ7重量%、6重量%及び8重量%の濃度で約90℃の温度で溶解させて、組成物Aを製造する。次に、前記組成物Aにプロピレンカーボネート(propylene carbonate)及びジステアルジモニウムヘクトライト(disteardimonium hectorite)をそれぞれ8重量%及び2重量%の濃度で追加し、20分間均一に分散させて、組成物Bを製造する。次に、前記に酸化鉄(iron oxide(CI77499))を6重量%の濃度で追加した後、保存料(preservatives)を適量添加し、30分間分散させた後、約28℃程度に徐々に冷却させて、マスカラ剤形を製造する。
マスカラ剤形をスライドガラス(ガラス板)に30μmの厚さに塗布した後、室温で完全乾燥する。乾燥後、マスカラに水と皮脂をそれぞれ0.1g落として、20分間放置した後、化粧綿をその上に載置し、200gfの力で30回往復運動した後、化粧綿についた程度を比較し、下記基準によって評価する。
〈評価基準〉
化粧綿についた程度によって0〜5の範囲内で尺度で比較したとき、化粧綿にマスカラが全然つかない場合を5にし、下記比較例1の高分子を適用した場合を対照群(reference)として3にし、前記対照群に比べて優れた水準をサンプル間の相対比較で小数点の第一桁まで数値化した。
製造されたマスカラ剤形を被実験者のまつげに塗布した後、6時間後に映像を撮影して比較し、下記基準に基づいて評価する。
〈評価基準〉
6時間経過後、映像を撮影し、広がり面積を映像分析することによって、数値で示す。映像分析時に、広がりの面積をピクセル(pixel)単位で数値化して示した。
前記製造されたマスカラ剤形をスライドガラス(ガラス板)に30μmの厚さに塗布した後、室温で完全乾燥させ、乾燥したサンプルを常温で水に約30分間沈積させた後に取り出して、質量減少率(=100×(1−B/A)、単位:%、前記Aは、マスカラ剤形が塗布されたスライドガラス全体質量であり、Bは、前記を水に沈積させた後に取り出した後、水気を除去してから測定したスライドガラス全体質量である)によって下記基準に基づいて耐水性を評価する。
〈評価基準〉
A:質量減少率が5%以下の場合
B:質量減少率が5%を超過する場合
実施例又は比較例で製造された高分子溶液を0.1g採取し、下記NMR用溶媒1mLに溶解させ、下記分析機器を使用して製造社のマニュアルによって1H−NMRを測定し、これを通じて高分子の成分及び転換率を確認できる。例えば、重合されない単量体が存在する場合、1H−NMRスペクトルで二重結合末端の=CH2に由来した−Hピークが約5.7ppm〜6.4ppm付近で確認され、各高分子構造に由来した−Hピークの面積を通じて製造高分子の成分を確認できる。
〈測定条件〉
分析機器:500MHz NMR(Varian UnityInova500)、1H−NMR
濃度:10〜20mg/mL、溶媒:CDCl3
温度:25℃
高分子の製造のための単量体は、下記表1に示された種類及び比率で適用した。表1に示されたように、単量体を混合した後、溶媒であるイソドデカン(Isododecane)に単量体の濃度が35重量%になるように投入し、さらに、適正量の熱開始剤(V−65、2、2’−azobis(2、4−dimentyl valeronitrile)を投入した後、反応器を密封する。次に、撹拌と共に常温で約30分間窒素でバブリングし、溶存酸素を除去し、酸素が除去された反応混合物を70℃程度の温度に昇温しつつ、約40分間窒素バブリングをさらに進行する。前記過程を通じて温度が70℃まで上昇すると、溶媒に溶解されていた熱開始剤により重合反応が進行される。約24時間程度反応を進行した後、温度を常温に低めて終了させる。下記表に示された組成及び前記記述した方式に従って高分子を重合させた結果、比較例1の場合、単量体間の重合が適切に行われず、単量体などが重合過程で析出され、高分子の合成が不可能であった。
実施例1の高分子に対するNMR評価結果、二重結合末端の=CH2に由来した1Hピークは確認されないことが分かり、これから重合が効果的に行われたことを確認できる。また、高分子で形成されたEHMA及びIBOMAの−COO−隣接した−CH2−及び−CH−ピークとPEGMAの−OCH2CH2−O及び−OCH3に由来したピークが5.0ppm〜2.8ppm領域で、面積値は14と確認された。また、NVPの−NCH2−に由来したピークが5.0ppm〜2.8ppm領域で、面積値は11と確認された。一方、高分子主鎖に由来した−CH2CH−及び−CH2CH2−から確認される1H面積値は、1.5ppm〜0.5ppmで51であった。
実施例の各高分子に対して物性を測定した結果を下記表2にまとめて記載した。但し、比較例の場合、高分子の製造過程で単量体などが析出され、重合が行われないため、物性評価を進行することができなかった。下記結果から、本出願の要件を満足する高分子の場合、極性溶媒(水、アセトン)と非極性溶媒(ヘキサン)に対しては低い溶解度を示し、その中間特性を有する溶媒(エチルアセテート)に対しては、優れた溶解度を示すことを確認できる。また、このような高分子を適用した場合には、耐水性が確保されながらも、皮脂広がりテストにおいても優れた皮脂抵抗性が確認された。
Claims (10)
- 単一高分子の溶解度パラメータが10(cal/cm3)1/2未満である第1単量体の重合単位と;単一高分子の溶解度パラメータが10(cal/cm3)1/2以上である第2単量体の重合単位と;ビニル系単量体の重合単位とを含む高分子であって、
第1単量体は、下記化学式1で表示される化合物であり:
第2単量体は、下記化学式2又は3で表示される化合物であり:
ビニル系単量体が下記化学式6で表示され:
第1単量体の重合単位70重量%以上、第2単量体の重合単位を前記第1単量体の重合単位100重量部に対して0.1〜30重量部、及びビニル系単量体の重合単位を前記第1単量体の重合単位100重量部に対して0.1〜40重量部を含む高分子。 - 第1単量体の単一高分子は、5(cal/cm3)1/2〜9.5(cal/cm3)1/2の範囲内の溶解度パラメータを有する、請求項1に記載の高分子。
- 第2単量体の単一高分子は、10.0(cal/cm3)1/2〜15.0(cal/cm3)1/2の範囲内の溶解度パラメータを有する、請求項1に記載の高分子。
- 誘電定数(25℃)が1〜3の範囲内である溶媒に対する常温においての溶解度が10以下であり、誘電定数(25℃)が75〜85の範囲内である溶媒に対する常温においての溶解度が10以下である、請求項1に記載の高分子。
- 誘電定数(25℃)が4〜15の範囲内である溶媒に対する常温においての溶解度が20以上である、請求項1に記載の高分子。
- 単一高分子の溶解度パラメータが10.0(cal/cm3)1/2未満である第1単量体と、単一高分子の溶解度パラメータが10.0(cal/cm3)1/2以上である第2単量体と、ビニル系単量体とを含む単量体混合物を溶媒内で溶液重合させる過程を含む、請求項1〜6のいずれか一項に規定の高分子の製造方法。
- 溶媒は、誘電定数(25℃)が1〜3の範囲内にある、請求項7に記載の高分子の製造方法。
- 溶媒は、液体パラフィンである、請求項7に記載の高分子の製造方法。
- 請求項1〜6のいずれか一項に規定の高分子を含むフィルム形成剤。
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