JP5989090B2 - 印刷インクにおける超分岐ポリエステル - Google Patents
印刷インクにおける超分岐ポリエステル Download PDFInfo
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- JP5989090B2 JP5989090B2 JP2014504331A JP2014504331A JP5989090B2 JP 5989090 B2 JP5989090 B2 JP 5989090B2 JP 2014504331 A JP2014504331 A JP 2014504331A JP 2014504331 A JP2014504331 A JP 2014504331A JP 5989090 B2 JP5989090 B2 JP 5989090B2
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- polyester
- hyperbranched polyester
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- C—CHEMISTRY; METALLURGY
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- C09D11/00—Inks
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- C09D11/104—Polyesters
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- C—CHEMISTRY; METALLURGY
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- C09D11/00—Inks
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Description
ポリマー材料のフィルム1の1つ
包装用印刷インクでの印刷又は被覆によって得られる印刷層の1つ
他のフィルム2の1つ
を含む、包装を製造するための多層材料であって、
前記包装用印刷インクは、少なくとも2つのバインダーを含み、
第一のバインダーが、OH基、COOH基及びCOOR基[ここでエステル化されたカルボキシル基における基Rは、炭素原子1〜60個を有する基を含み、かつ場合によりヘテロ原子又は他の置換基を含んでよい]からなる群から選択される官能基を含む少なくとも1つの超分岐ポリエステルを含み、
その際、前記超分岐ポリエステルは、
フタル酸、イソフタル酸、テレフタル酸、1,2−シクロヘキサンジカルボン酸、1,3−シクロヘキサンジカルボン酸、1,4−シクロヘキサンジカルボン酸及びメチルヘキサヒドロフタル酸又はそれらの誘導体からなる群から選択される少なくとも1つの脂環式又は芳香族ジカルボン酸(A2)又はそれらの誘導体と
トリメチロールプロパン、グリセロール及びペンタエリトリトールからなる群から選択されるOH基x個を含む、少なくとも1つの少なくとも三価の脂肪族アルコール(Cx)と
を反応させることによって得られ、
実質的にOH基2個を含む脂環式ジオール(B2)は存在せず、
前記ポリエステルの分子量Mnは、少なくとも300g/molであり、かつ多分散性Mw/Mnは1.2〜10であり、かつ
反応混合物における全ての成分の反応基の割合は、ヒドロキシル基とカルボキシル基又はそれらの誘導体とのモル比が2:1〜1:2であるように選択され、
第二のバインダーが、ポリビニルブチラール、ニトロセルロース、ポリアミド、ポリウレタン、ポリ塩化ビニル、ポリケトン、ポリカーボネート、ポリアクリレート及びポリアクリレートコポリマーからなる群から選択され、
その際、全てのバインダーの合計量に対する超分岐ポリエステルの質量比が少なくとも50質量%である、
多層材料によって達せられることを見出している。
DB(%)=(T+Z)/(T+Z+L)×100
によって定義され、その際
Tは末端結合モノマーの中間数であり、
Zはモノマーを生じる分岐の中間数であり、
Lは直鎖結合モノマーの中間数である。
エステル化カルボキシル基における基Rは、有利には炭素原子1〜60個を有する基を含む。前記基は、ヘテロ原子又は他の置換基を含んでもよい。
− モノマー又は他のポリマー形での対応する無水物
− モノアルキル又はジアルキルエステル、有利にはモノ−又はジ−C1〜C4アルキルエステル、より有利にはモノメチルエステルもしくはジメチルエステル又は対応するモノエチルエステルもしくはジエチルエステル、
− さらにモノビニルエステル及びジビニルエステル、並びに
− 混合エステル、有利には種々のC1〜C4アルキル成分を有する混合エステル、より有利には混合メチルエチルエステル
を意味する。
C1〜C20アルキル基、例えばメチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、sec−ブチル、tert−ブチル、n−ペンチル、イソペンチル、sec−ペンチル、ネオペンチル、1,2−ジメチルプロピル、イソアミル、n−ヘキシル、イソヘキシル、sec−ヘキシル、n−ヘプチル、イソヘプチル、n−オクチル、2−エチルヘキシル、n−ノニル、n−デシル、n−ドデシル、n−ヘキサデシル又はn−オクタデシル
C3〜C12シクロアルキル基、例えばシクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、シクロノニル、シクロデシル、シクロウンデシル及びシクロドデシル、有利にはシクロペンチル、シクロヘキシル及びシクロヘプチル
から選択することができる。
一般の方法:
分子量を、ゲル透過クロマトグラフィー(GPC)によって測定した;溶出液:テトラヒドロフラン(THF);参考材料:PMMA。
酸数(AN)を、前記DIN 53402に従って測定した。
ヒドロキシル価(OH価)を、DIN 53240、第2部に従って測定した。
DBTL=ジブチルスズジラウレート
TMP=トリメチロールプロパン
HPAA=1,2−シクロヘキサンジカルボン酸無水物(CAS 85−42−7)。
比較例1(US 2005/0147834号A1の実施例1の生成物に類似):
機械撹拌機、温度計、ガス入口及び収集フラスコを有する蒸留装置を備えた2リットルの丸底フラスコ中に、アジピン酸680g(4.65mol)及びTMP520g(3.88mol)を置いた。DBTL0.36gを触媒として添加し、そして反応混合物を撹拌下で160℃まで加熱した。その混合物を、160℃で3時間撹拌し、そして反応水を収集した。反応は酸数に従い、酸数87mg KOH/g(ポリマー)を得た場合に、周囲温度まで冷却することによって反応を停止した。
機械撹拌機、温度計、ガス入口及び収集フラスコを有する蒸留装置を備えた2リットルの丸底フラスコ中に、アジピン酸680g(4.65mol)及びTMP520g(3.88mol)を置いた。DBTL0.36gを触媒として添加し、そして反応混合物を撹拌下で160℃まで加熱した。その混合物を、160℃で4時間撹拌し、そして反応水を収集した。反応は酸数に従い、酸数100mg KOH/g(ポリマー)を得た場合に、周囲温度まで冷却することによって反応を停止した。
機械撹拌機、温度計、ガス入口及び収集フラスコを有する蒸留装置を備えた2リットルの丸底フラスコ中に、HPAA580g(3.76mol)、及びTMP420g(3.13mol)を置いた。DBTL0.3gを触媒として添加し、そして反応混合物を撹拌下で160℃まで加熱した。その混合物を、180℃で6時間撹拌し、そして反応水を収集した。反応は酸数に従い、酸数92mg KOH/g(ポリマー)を得た場合に、周囲温度まで冷却することによって反応を停止した。
機械撹拌機、温度計、ガス入口及び収集フラスコを有する蒸留装置を備えた1リットルの丸底フラスコ中に、HPAA348g(2.26mol)、及びTMP252g(1.88mol)を置き、そして180℃で5.5時間加熱し、そしてその反応水をその時間除去した。反応は酸数に従い、酸数93mg KOH/g(ポリマー)を得た場合に、周囲温度まで冷却することによって反応を停止した。
機械撹拌機、温度計、ガス入口及び収集フラスコを有する蒸留装置を備えた2リットルの丸底フラスコ中に、1,2−フタル酸無水物551g(3.7mol)、及びTMP500g(3.7mol)を置いた。DBTL0.3gを触媒として添加し、そして反応混合物を7時間の撹拌下で180℃まで加熱し、そして反応水を収集した。反応は酸数に従い、酸数40mg KOH/g(ポリマー)を得た場合に、周囲温度まで冷却することによって反応を停止した。
印刷工業において印刷されたフィルム上のインク接着を調べる一般の方法は、テープ接着(ASTM F 2252−03)である。測定を、インクを1時間室温でドローダウンした後に実施し、溶剤が完全に蒸発されたか確認した。結果を1〜5の尺度で評価する:5は、フィルムからはがれたインクがなく、1は、フィルムから100%はがれた。
耐ブロッキング性を、スプリング式プレス、Koehler Instrument社製のK53000 I.C.ブロック試験器を使用して測定する。この試験は、熱及び圧力を有する貯蔵条件下で印刷したフィルムのロールを評価することである。ブロッキング試験を、10psi、50℃、16時間で設定する。評価は1〜5の尺度である;5はインクはがれがなく良好であり、1はフィルムから100%はがれた。
積層インクについての重大な性能は、印刷されたフィルムと、通常低い融点を有するポリオレフィン、例えばLDPE、低密度ポリエチレンであるシーラントフィルムとを結合する接着剤の使用で完全な積層品を形成する能力である。Tycel(登録商標)UR7975/UR6029(Liofol Corporation社製)を接着剤として使用した。積層品試料の結合強度を、Instron(登録商標)、引張試験機によって評価した。最も一般の構成は、"T"形成をもたらす共に接着されている基材の2つのストリップを引き離すことを含む、標準T−peelである(ASTM D1876)。
Claims (12)
- 少なくとも
ポリマー材料のフィルム1の1つ
包装用印刷インクでの印刷又は被覆によって得られる印刷層の1つ
他のフィルム2の1つ
を含む、包装を製造するための多層材料であって、
前記包装用印刷インクが、少なくとも2つのバインダーを含み、
第一のバインダーが、OH基、COOH基及びCOOR基[ここでエステル化されたカルボキシル基における基Rは、炭素原子1〜60個を有する基を含み、かつ場合によりヘテロ原子又は他の置換基を含んでもよい]からなる群から選択される官能基を含む少なくとも1つの超分岐ポリエステルを含み、
その際、前記超分岐ポリエステルが、
フタル酸、イソフタル酸、テレフタル酸、1,2−シクロヘキサンジカルボン酸、1,3−シクロヘキサンジカルボン酸、1,4−シクロヘキサンジカルボン酸及びメチルヘキサヒドロフタル酸又はそれらの誘導体からなる群から選択される少なくとも1つの脂環式又は芳香族ジカルボン酸(A2)又はそれらの誘導体と
トリメチロールプロパン、グリセロール及びペンタエリトリトールからなる群から選択されるOH基x個を含む、少なくとも1つの少なくとも三価の脂肪族アルコール(Cx)と
を反応させることによって得られ、
OH基2個を含むジオール(B2)は存在せず、
前記ポリエステルの分子量Mnが、少なくとも300g/molであり、かつ多分散性Mw/Mnは1.2〜10であり、かつ
反応混合物における全ての成分の反応基の割合が、ヒドロキシル基とカルボキシル基又はそれらの誘導体とのモル比が2:1〜1:2であるように選択され、
第二のバインダーが、ポリビニルブチラール、ニトロセルロース、ポリアミド、ポリウレタン、ポリ塩化ビニル、ポリケトン、ポリカーボネート、ポリアクリレート及びポリアクリレートコポリマーからなる群から選択され、
全てのバインダーの合計量に対する超分岐ポリエステルの質量比が少なくとも50質量%である、前記多層材料。 - フィルム1が、ポリエチレン、ポリプロピレン、ポリスチレン、ポリエステル及びポリアミドからなる群から選択されることを特徴とする、請求項1に記載の多層材料。
- フィルム2が、ポリエチレン、ポリプロピレン、ポリスチレン、ポリエステル、ポリアミド、及びアルミニウム箔からなる群から選択されることを特徴とする、請求項1に記載の多層材料。
- 前記超分岐ポリエステルのガラス転移温度が20〜60℃であることを特徴とする、請求項1に記載の多層材料。
- 前記ジカルボン酸(A2)が、1,2−シクロヘキサンジカルボン酸又は1,2−シクロヘキサンジカルボン酸無水物であることを特徴とする、請求項1に記載の多層材料。
- 前記OH基x個を含む少なくとも三価の脂肪族アルコール(Cx)が、トリメチロールプロパンであることを特徴とする、請求項1に記載の多層材料。
- 前記第二のバインダーが、ニトロセルロース及びポリウレタンからなる群から選択されることを特徴とする、請求項1に記載の多層材料。
- 前記包装用印刷インクが、さらに、バインダーとしてニトロセルロースを含み、その際全樹脂に対する超分岐ポリエステルの質量比が、少なくとも50質量%であり、100質量%未満であることを特徴とする、請求項1に記載の多層材料。
- 以下、
フタル酸、イソフタル酸、テレフタル酸、1,2−シクロヘキサンジカルボン酸、1,3−シクロヘキサンジカルボン酸、1,4−シクロヘキサンジカルボン酸及びメチルヘキサヒドロフタル酸又はそれらの誘導体からなる群から選択される少なくとも1つの脂環式又は芳香族ジカルボン酸(A2)と
トリメチロールプロパン、グリセロール及びペンタエリトリトールからなる群から選択されるOH基x個を含む少なくとも1つの少なくとも三価の脂肪族アルコール(Cx)と
を反応させることによって得られる超分岐ポリエステルであって、
OH基2個を含むジオール(B2)は存在せず、
前記ポリエステルの分子量Mnが少なくとも300g/molであり、かつ多分散性Mw/Mnが1.1〜20であり、かつ
反応混合物における全ての成分の反応基の割合が、ヒドロキシル基とカルボキシル基又はそれらの誘導体とのモル比が2:1〜1:2であるように選択される、
前記超分岐ポリエステルの、印刷インクにおけるバインダーとしての使用。 - 以下、
− 第一のバインダーとして、
フタル酸、イソフタル酸、テレフタル酸、1,2−シクロヘキサンジカルボン酸、1,3−シクロヘキサンジカルボン酸、1,4−シクロヘキサンジカルボン酸及びメチルヘキサヒドロフタル酸又はそれらの誘導体からなる群から選択される少なくとも1つの脂環式又は芳香族ジカルボン酸(A2)と
トリメチロールプロパン、グリセロール及びペンタエリトリトールからなる群から選択されるOH基x個を含む少なくとも1つの少なくとも三価の脂肪族アルコール(Cx)と
を反応させることによって得られる少なくとも1つの超分岐ポリエステルであって、
OH基2個を含むジオール(B2)は存在せず、
前記ポリエステルの分子量Mnが少なくとも300g/molであり、かつ多分散性Mw/Mnが1.1〜20であり、かつ
反応混合物における全ての成分の反応基の割合が、ヒドロキシル基とカルボキシル基又はそれらの誘導体とのモル比が2:1〜1:2であるように選択される、超分岐ポリエステル
− ポリビニルブチラール、ニトロセルロース、ポリアミド、ポリウレタン、ポリ塩化ビニル、ポリケトン、ポリカーボネート、ポリアクリレート及びポリアクリレートコポリマーからなる群から選択される第二のバインダー、
− 少なくとも1つの溶剤、
− 場合によりさらに少なくとも1つの着色剤、
− 場合によりさらに、添加剤及び助剤からなる群から選択される少なくとも1つの化合物
を含む印刷インクであって、
全てのバインダーの合計量に対する超分岐ポリエステルの質量比が少なくとも50質量%である、前記印刷インク。 - 包装用印刷インクにおける揮発性有機化合物(VOC)の含有率を減少させ及び/又は顔料装填量を増加させるための超分岐ポリエステルの使用であって、
前記超分岐ポリエステルが、OH基、COOH基及びCOOR基[ここでエステル化されたカルボキシル基における基Rは、炭素原子1〜60個を有する基を含み、かつ場合によりヘテロ原子又は他の置換基を含んでもよい]からなる群から選択される官能基を含み、
前記超分岐ポリエステルが、
フタル酸、イソフタル酸、テレフタル酸、1,2−シクロヘキサンジカルボン酸、1,3−シクロヘキサンジカルボン酸、1,4−シクロヘキサンジカルボン酸及びメチルヘキサヒドロフタル酸又はそれらの誘導体からなる群から選択される少なくとも1つの脂環式又は芳香族ジカルボン酸(A2)又はそれらの誘導体と
トリメチロールプロパン、グリセロール及びペンタエリトリトールからなる群から選択されるOH基x個を含む、少なくとも1つの少なくとも三価の脂肪族アルコール(Cx)と
を反応させることによって得られ、
OH基2個を含むジオール(B 2 )は存在せず、
前記ポリエステルの分子量Mnが、少なくとも300g/molであり、かつ多分散性Mw/Mnは1.1〜20であり、かつ
反応混合物における全ての成分の反応基の割合が、ヒドロキシル基とカルボキシル基又はそれらの誘導体とのモル比が2:1〜1:2であるように選択され、
前記包装用印刷インクが少なくとも2つのバインダーを含み、第一のバインダーが少なくとも1つの前記超分岐ポリエステルを含み、第二のバインダーがポリビニルブチラール、ニトロセルロース、ポリアミド、ポリウレタン、ポリ塩化ビニル、ポリケトン、ポリカーボネート、ポリアクリレート及びポリアクリレートコポリマーからなる群から選択され、
全てのバインダーの合計量に対する超分岐ポリエステルの質量比が少なくとも50質量%であって100質量%未満である、前記超分岐ポリエステルの使用。 - 前記包装用印刷インクが包装を製造するための多層材料に使用され、
前記多層材料が、少なくとも
ポリマー材料のフィルム1の1つ
包装用印刷インクでの印刷又は被覆によって得られる印刷層の1つ
他のフィルム2
を含む、請求項11に記載の使用。
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