JPWO2021122574A5 - - Google Patents

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JPWO2021122574A5
JPWO2021122574A5 JP2022536615A JP2022536615A JPWO2021122574A5 JP WO2021122574 A5 JPWO2021122574 A5 JP WO2021122574A5 JP 2022536615 A JP2022536615 A JP 2022536615A JP 2022536615 A JP2022536615 A JP 2022536615A JP WO2021122574 A5 JPWO2021122574 A5 JP WO2021122574A5
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Prior art keywords
meth
acrylate
led
offset printing
printing ink
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JP2022536615A
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JP2023506825A (en
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Priority claimed from PCT/EP2020/086189 external-priority patent/WO2021122574A1/en
Publication of JP2023506825A publication Critical patent/JP2023506825A/en
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Claims (14)

基材にフィーチャをオフセット印刷するための、40℃及び1000s-1 で2.5~25Pa sの範囲の粘度を有するUV-LEDラジカル硬化性オフセット印刷インクであって、前記UV-LEDラジカル硬化性オフセット印刷インクが、
)10wt.%~80wt.%の、1種又は複数のラジカル硬化性(メタ)アクリレートオリゴマー及び1種又は複数のラジカル硬化性(メタ)アクリレートモノマーからなる1種又は複数のラジカル硬化性(メタ)アクリレート化合物であり、
前記ラジカル硬化性(メタ)アクリレートオリゴマーが、エポキシ(メタ)アクリレート、(メタ)アクリル化オイル、(メタ)アクリル化エポキシ化オイル、ポリエステル(メタ)アクリレート、脂肪族又は芳香族ポリウレタン(メタ)アクリレート、ポリアクリル酸(メタ)アクリレート、ポリアクリレートエステル(メタ)アクリレート、及びそれらの混合物からなる群から選択され、
前記ラジカル硬化性(メタ)アクリレートモノマーが、モノ(メタ)アクリレート、ジ(メタ)アクリレート、トリ(メタ)アクリレート、テトラ(メタ)アクリレート、ペンタ(メタ)アクリレート、ヘキサ(メタ)アクリレート及びそれらの混合物からなる群から選択される、1種又は複数のラジカル硬化性(メタ)アクリレート化合物
ii)4wt.%~20wt.%の式(I)の1種又は複数の光開始剤:

[式中、Qは以下の式(IIa)、(IIb)又は(IIc)を有する:


(式中、nは1以上であり、R1は互いに同一であるか又は異なり、水素及びC~Cアルキル基からなる群から選択され、R2は水素及びC~Cアルキル基からなる群から選択され、a+b+cの合計は3~12であり、d+e+f+gの合計は4~16である)]
iii)少なくとも400g/mol eq PSの重量平均分子量を有するアミノベンゾエート化合物、少なくとも400g/mol eq PSの重量平均分子量を有するアミン変性ポリエーテル系アクリレート、及びこれらの組合せからなる群から選択される、1wt.%~15wt.%の1種又は複数のアミノ含有化合物、並びに
iv)1wt.%~30wt.%の1種若しくは複数の無機顔料及び/又は1種若しくは複数の有機顔料、並びに
v)炭素繊維、タルク、マイカ、珪灰石、粘土、カオリン、炭酸塩、ケイ酸塩、硫酸塩、チタン酸塩、アルミナ水和物、シリカ、モンモリロナイト、グラファイト、ベントナイト、バーミキュライト、木粉、石英粉、天然繊維、合成繊維、及びそれらの組合せからなる群から選択される0.5wt.%~10wt.%の1種若しくは複数の充填剤及び/又は増量剤
を含み、重量パーセントがUV-LEDラジカル硬化性オフセット印刷インクの全重量に基づく、UV-LEDラジカル硬化性オフセット印刷インク。
2. at 40° C. and 1000 s −1 to offset print features on the substrate. A UV-LED radical-curable offset printing ink having a viscosity in the range of 5 to 25 Pa s, said UV-LED radical-curable offset printing ink comprising:
i ) 10wt . % ~80wt . % of one or more radically curable (meth)acrylate oligomers and one or more radically curable (meth)acrylate monomers,
The radical curable (meth)acrylate oligomer is epoxy (meth)acrylate, (meth)acrylated oil, (meth)acrylated epoxidized oil, polyester (meth)acrylate, aliphatic or aromatic polyurethane (meth)acrylate, selected from the group consisting of polyacrylic acid (meth)acrylate, polyacrylate ester (meth)acrylate, and mixtures thereof;
The radically curable (meth)acrylate monomer is mono(meth)acrylate, di(meth)acrylate, tri(meth)acrylate, tetra(meth)acrylate, penta(meth)acrylate, hexa(meth)acrylate, and mixtures thereof. one or more radically curable (meth)acrylate compounds selected from the group consisting of ii ) 4 wt. % ~20wt . % of one or more photoinitiators of formula (I):

[wherein Q has the following formula (IIa), (IIb) or (IIc):


(wherein n is 1 or more, R1 are the same or different from each other and are selected from the group consisting of hydrogen and C 1 -C 3 alkyl groups, and R 2 consists of hydrogen and C 1 -C 3 alkyl groups) selected from the group, the sum of a+b+c is 3 to 12 and the sum of d+e+f+g is 4 to 16)]
iii) selected from the group consisting of aminobenzoate compounds having a weight average molecular weight of at least 400 g/mol eq PS, amine-modified polyether-based acrylates having a weight average molecular weight of at least 400 g/mol eq PS, and combinations thereof , 1 wt. % ~ 15wt. % of one or more amino-containing compounds, and iv ) 1 wt. % ~30wt . % of one or more inorganic pigments and/or one or more organic pigments, and v) carbon fibers, talc, mica, wollastonite, clays, kaolin, carbonates, silicates, sulfates, titanates. , alumina hydrate, silica, montmorillonite, graphite, bentonite, vermiculite, wood flour, quartz powder, natural fibers, synthetic fibers, and combinations thereof . 5wt. % ~10wt . % of one or more fillers and/or extenders, the weight percentages being based on the total weight of the UV-LED radical curable offset printing ink.
1種又は複数の光開始剤が式(I)のものであり、Qが以下の式(IIb-1)、(IIb-2)又は(IIb-3):

(式中、nは1、2又は3に等しく、a+b+cの合計は3~12である)
を有する、請求項1に記載のUV-LEDラジカル硬化性オフセット印刷インク。
The one or more photoinitiators are of formula (I) and Q is of formula (IIb-1), (IIb-2) or (IIb-3):

(where n is equal to 1, 2 or 3 and the sum of a+b+c is 3 to 12)
The UV-LED radical curable offset printing ink according to claim 1, comprising:
1種又は複数のアミノ含有化合物が、少なくとも700g/mol eq PSの重量平均分子量を有するアミノベンゾエート化合物、少なくとも700g/mol eq PSの重量平均分子量を有するアミン変性ポリエーテル系アクリレート、及びこれらの組合せからなる群から選択される、請求項1又は2に記載のUV-LEDラジカル硬化性オフセット印刷インク。 The one or more amino-containing compounds are from aminobenzoate compounds having a weight average molecular weight of at least 700 g/mol eq PS, amine-modified polyether-based acrylates having a weight average molecular weight of at least 700 g/mol eq PS, and combinations thereof. The UV-LED radical curable offset printing ink according to claim 1 or 2, selected from the group consisting of: 1種又は複数のアミノ含有化合物が、アミノベンゾエート化合物を含むアミノ含有化合物からなる群から選択される、請求項1~3のいずれか一項に記載のUV-LEDラジカル硬化性オフセット印刷インク。 UV-LED radical curable offset printing ink according to any one of claims 1 to 3, wherein the one or more amino-containing compounds are selected from the group consisting of amino-containing compounds including aminobenzoate compounds. 1種又は複数のアミノ含有化合物が、式(III):

(式中、mは1より大きく、h+i+j+kの合計は3~12である)
を有するアミノベンゾエート化合物からなる群から選択される、請求項4に記載のUV-LEDラジカル硬化性オフセット印刷インク。
The one or more amino-containing compounds have the formula (III):

(In the formula, m is greater than 1, and the sum of h+i+j+k is 3 to 12)
5. The UV-LED radical curable offset printing ink according to claim 4, selected from the group consisting of aminobenzoate compounds having:
1種又は複数の無機顔料及び1種又は複数の有機顔料が、粒度分析ゲージを使用して測定した場合に5μm以下の粒径を独立的に有する、請求項1~5のいずれか一項に記載のUV-LEDラジカル硬化性オフセット印刷インク。 Any one of claims 1 to 5, wherein the one or more inorganic pigments and the one or more organic pigments independently have a particle size of 5 μm or less when measured using a particle size analysis gauge. The UV-LED radical curable offset printing ink described in . ラフィンワックス、ポリエチレンワックス、フルオロカーボンワックス、ポリテトラフルオロエチレンワックス、カルナウバワックス、及びそれらの混合物からなる群から選択される1種又は複数のワックスをさらに含む、請求項1~6のいずれか一項に記載のUV-LEDラジカル硬化性オフセット印刷インク。 Any one of claims 1 to 6, further comprising one or more waxes selected from the group consisting of paraffin wax, polyethylene wax, fluorocarbon wax, polytetrafluoroethylene wax, carnauba wax, and mixtures thereof. The UV-LED radical curable offset printing ink described in 2. オフセット印刷方法によってフィーチャを基材に印刷するための方法であって、
a)請求項1~7のいずれか一項に記載のUV-LEDラジカル硬化性オフセット印刷インクをオフセット印刷によって塗布し、インク層を形成するステップ、及び
b)少なくとも150mJ/cm 線量でインク層をUV光に曝露し、前記インク層をUV-LED源によって硬化するステップ
を含む、方法。
A method for printing features on a substrate by an offset printing method, the method comprising:
a) applying the UV-LED radical curable offset printing ink according to any one of claims 1 to 7 by offset printing to form an ink layer, and b) the ink at a dose of at least 150 mJ/ cm2 . A method comprising exposing a layer to UV light and curing said ink layer with a UV-LED source.
ステップb)が、インク層を355nm~415nmの1つ又は複数の波長に曝露することからなる、請求項8に記載の方法。 9. The method of claim 8, wherein step b) consists of exposing the ink layer to one or more wavelengths from 355 nm to 415 nm. 40℃及び1000s-1 で2.5~25Pa sの範囲の粘度を有するUV-LEDラジカル硬化性オフセット印刷インクを生成するための、4wt.%~20wt.%の量の請求項1又は2に記載の1種又は複数の光開始剤、及び1wt.%~15wt.%の量の請求項1、3、4又は5に記載の1種又は複数のアミノ含有化合物の使用であって、
前記UV-LEDラジカル硬化性オフセット印刷インクが、セキュリティ文書に1つ又は複数のフィーチャを印刷するのに好適であり、前記UV-LEDラジカル硬化性オフセット印刷インクが、10wt.%~80wt.%のラジカル硬化性(メタ)アクリレート化合物、1wt.%~30wt.%の1種若しくは複数の無機顔料及び/又は1種若しくは複数の有機顔料、並びに0.5wt.%~10wt.%の1種若しくは複数の充填剤及び/又は増量剤を含み、重量パーセントがUV-LEDラジカル硬化性オフセット印刷インクの全重量に基づく、使用。
2 at 40°C and 1000 s -1 . 4 wt. to produce a UV-LED radical curable offset printing ink with a viscosity in the range of 5 to 25 Pa s. % ~20wt . % of one or more photoinitiators according to claim 1 or 2, and 1 wt. % ~ 15wt. % of one or more amino-containing compounds according to claim 1, 3, 4 or 5 ,
The UV-LED radical curable offset printing ink is suitable for printing one or more features on a security document, and the UV-LED radical curable offset printing ink has an amount of 10 wt. % ~80wt . % radically curable (meth)acrylate compound , 1 wt. % ~30wt . % of one or more inorganic pigments and/or one or more organic pigments and 0 . 5wt. % ~10wt . % of one or more fillers and/or extenders, the weight percentages being based on the total weight of the UV-LED radical curable offset printing ink.
請求項1~7のいずれか一項に記載のUV-LEDラジカル硬化性オフセット印刷インク硬化物であるインク層からなる印刷フィーチャ。 A printed feature comprising an ink layer that is a cured product of the UV-LED radical-curable offset printing ink according to any one of claims 1 to 7. 基材及び請求項11に記載の1つ又は複数の印刷フィーチャを含むセキュリティ文書。 A security document comprising a substrate and one or more printed features according to claim 11. 1つ又は複数の印刷フィーチャが、50%以上の全表面を有し、%が前記1つ又は複数の印刷フィーチャが存在する基材の全表面に基づく、請求項12に記載のセキュリティ文書。 13. The security document of claim 12, wherein the one or more printed features have a total surface of 50 % or more , where % is based on the total surface of the substrate on which the one or more printed features are present. . 基材が非蛍光基材である、請求項12又は13に記載のセキュリティ文書。 The security document according to claim 12 or 13, wherein the substrate is a non-fluorescent substrate.
JP2022536615A 2019-12-18 2020-12-15 UV-LED radical curable offset printing ink and printing method Pending JP2023506825A (en)

Applications Claiming Priority (3)

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EP19217484 2019-12-18
EP19217484.5 2019-12-18
PCT/EP2020/086189 WO2021122574A1 (en) 2019-12-18 2020-12-15 Uv-led radically curable offset printing inks and printing processes

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JPWO2021122574A5 true JPWO2021122574A5 (en) 2023-11-24

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KR (1) KR20220114601A (en)
CN (1) CN114829511B (en)
AR (1) AR120745A1 (en)
AU (1) AU2020405994A1 (en)
BR (1) BR112022011671A2 (en)
CA (1) CA3164478A1 (en)
MX (1) MX2022007693A (en)
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