JPH01139554A - 芳香族α−アミノケトン - Google Patents

芳香族α−アミノケトン

Info

Publication number
JPH01139554A
JPH01139554A JP63250739A JP25073988A JPH01139554A JP H01139554 A JPH01139554 A JP H01139554A JP 63250739 A JP63250739 A JP 63250739A JP 25073988 A JP25073988 A JP 25073988A JP H01139554 A JPH01139554 A JP H01139554A
Authority
JP
Japan
Prior art keywords
alk
formula
alkyl
compd
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP63250739A
Other languages
English (en)
Other versions
JPH0248536B2 (ja
Inventor
Louis Felder
ルイス　フェルダー
Rudolf Kirchmayr
ルドルフ　キルヒメイヤー
Rinaldo Huesler
リナルド　ヒスラー
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of JPH01139554A publication Critical patent/JPH01139554A/ja
Publication of JPH0248536B2 publication Critical patent/JPH0248536B2/ja
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/07—Aldehydes; Ketones
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing
    • Y10S430/117—Free radical
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing
    • Y10S430/12—Nitrogen compound containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing
    • Y10S430/12—Nitrogen compound containing
    • Y10S430/121—Nitrogen in heterocyclic ring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing
    • Y10S430/122—Sulfur compound containing

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymerisation Methods In General (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)

Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。

Description

【発明の詳細な説明】 本発＃Ｊは、α−位においてアεノ基によって置換され
た新規芳香−脂肪族ケトンに関する。
該化合物は不飽和化合物の光重合開始剤として有用であ
る。
新規な化合物は、次式■ （式中、 ＡｒはＯＨ％ａｔｋ　１−ａｔｋｌ−０フエニル、もし
くは−５ａｔｋにより置換されたフェニル基を表わし、 Ｒ１およびＲ２は独立して炭素原子数１ないし８のアル
キル基を表わすかまたはＲ１およびＲ２は一緒になって
−（ＣＨ２）Ｓ−を表わし、そしてＲ４およびＲ５は独
立して炭素原子数１ないし１２のアルキル基を表わすか
もしくは一０ａｔｋにより置換された炭素原子数２ない
し４のアルキル基を表わすか、または Ｒ４およびＲ５は一緒になって一〇−１−ＮＨ−１もし
くは−Ｎａｔｋ−によって中断されうる炭素原子数４ま
たは５のアルキレン基を表わし、 ａｔｋは炭素原子数１ないし４のアルキル基を表わす。
）で表わされる化合物である。
式■で表わされる化合物は、次の反応段階により芳香−
脂肪族ケトンから製造することができる。
ＨｓＯＮａ Ａｒ−ＣＯ−ＣＨＲ’Ｒ”　＋　Ｂｒ２−＋　Ａｒ−Ｃ
ｏ−ＣＢｒＲ’Ｒ”　−一→次の方法により単一の段階
を遂行することもできる。
当該ケトンを不活性溶媒中、好ましくは四基に窒素を・
導入する。最後に溶媒を蒸留で除去する。ブロモケトン
の精製は必要とされない。
段階Ｂ−エポキシド中間体の製造 ブロモケトンをメタノール中に溶解しそしてメタノール
中のナトリウムメトキシド１モル溶液を還流温度にて滴
下する。次いでメタノールを蒸留で除きそして残留物を
氷水中に注入しそしてエーテルで抽出する。エーテル性
溶液を水で洗浄し、Ｎａ　２　ＳＯ４上で乾燥しそして
濃縮する。
残渣は再結晶または真空蒸留によシ謂裂することができ
る。しかし、次の段階で使用するためには精製は何ら必
要とされない。
段階Ｃ−α−アミノケトンの製造 原料エボキクドを、溶媒を用いずにまたは少量のトルエ
ンもしくはキシレンを添加して１モルの第二アミンで処
理し、そして１００−２００℃にて約１０ないし２０時
間の間反応させる。低沸点アミン、例えばジメチルアミ
ンまたはジエチルアミンを使用する場合、反応をオート
クレーブ中で行う。反応混合物をベンゼンで希釈しそし
て希塩酸で抽出する。その酸性水溶液をＮａＯＨでアル
カリ性にしそしてエーテルで抽出する。エーテル性溶液
を水で洗浄し、Ｎａ２ＳＯ４上で乾燥しそして濃縮する
。粗生成物を蒸留、結晶化またはＡｔ２０３カラムでの
クロマトグラフィーにより精製する。
以下のα−アミノケトンは、これら反応段階によって合
成されたものである。
式Ｉで表わされる化合物はエチレン性不飽和化合物の光
重合開始剤として使用することができる。その不飽和化
合物は、例えばアクリル酸もしくはメタアクリル酸のモ
ノ−もしくはポリエステル、ビニルエステル、アリルエ
ステルまたは不飽和ポリエステル樹脂であってよい。か
かる不飽和化合物の混合物は光重合性組成物としてよく
使用される。かかる光１合性組成物は、一般に薄層中に
、例えば塗料層または印刷インク層中に使用される。工
業的用途において光硬化の速度は重要な要素でありそれ
は主に光開始剤の活性に依存する。式Ｉで表わされる化
合物は、次の試験において示されるように高い重合活性
を有する。
試験例 次の成分からなる混合物を製造した。
エボキクアクリレート　　　　　　　　６９部（エベク
リル（Ｅｂｅｃｒｙｌ　）　６０８　、ベルギー国ＵＣ
Ｂ社製）オリゴマー　トリスアクリレート　　　　　　
　　３０部（ＯＴＡ４８０．ＵＣＢ社裂〕 シリコーン　ジアクリレート　　　　　　　　　　　　
　１部（エペクリル（Ｅｂｅｃｒｙｌ　）　３５０　、
ＵＣＢ社裂）光開始剤　　　　　　　　　　　　　　２
部（部は全て重量部を表わす。） 混合物をガラス板上に５０μｍの厚さにナイフで塗布す
る。試料を８０ワツトの電球を２個備えたＰＰＧ装置（
紫外線照射装置）中で照射する。試料が照射装置を通過
した後、フィルムのふき取り堅牢度を紙ハンカチでこす
ることにより試験した。通過速度を上昇させそして耐ふ
き取り性フィルムを得るための最大速度を求めた。
それを表５に示す。
表３ １）ベンゾイン　イソグロビルエーテル２）ベンジル　
ジメチルケタール 表３に示すように式■で表わされる化合物の光硬化活性
は市販の光開始剤Ｖｉｃｕｒｅ　５０　（５ｔａｎ−ｆ
ｆｅｒ　Ｃｏｒｐ−の製品）またはＩｒｇａｃｕｒｅ　
６５１　（チバーカイギー　ＡＧの製品）のそれに比し
て顕著により高い。

Claims (1)

    【特許請求の範囲】
  1. （１）次式 I ▲数式、化学式、表等があります▼（ I ） （式中、 ＡｒはＯＨ、ａｌｋ、−ａｌｋ、−Ｏフェニル、もしく
    は−Ｓａｌｋにより置換されたフェニル基を表わし、 Ｒ＾１およびＲ＾２は独立して炭素原子数１ないし８の
    アルキル基を表わすかまたはＲ＾１およびＲ＾２は一緒
    になって−（ＣＨ＿２）＿５−を表わし、そしてＲ＾４
    およびＲ＾５は独立して炭素原子数１ないし１２のアル
    キル基を表わすかもしくは−Ｏａｌｋにより置換された
    炭素原子数２ないし４のアルキル基を表わすか、または Ｒ＾４およびＲ＾５は一緒になって−Ｏ−、−ＮＨ−、
    もしくは−Ｎａｌｋ−によって中断されうる炭素原子数
    ４または５のアルキレン基を表わし、ａｌｋは炭素原子
    数１ないし４のアルキル基を表わす。）で表わされる化
    合物。
JP63250739A 1977-12-22 1988-10-04 芳香族α−アミノケトン Granted JPH01139554A (ja)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CH15884/77 1977-12-22
CH1588477 1977-12-22
CH251878 1978-03-08
CH2518/78 1978-03-08
CH9723/78-1 1978-09-18
CH972378 1978-09-18

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
JP16090978A Division JPS5499185A (en) 1977-12-22 1978-12-22 Photopolymerization initiator and photopolymerizable composition

Publications (2)

Publication Number Publication Date
JPH01139554A true JPH01139554A (ja) 1989-06-01
JPH0248536B2 JPH0248536B2 (ja) 1990-10-25

Family

ID=27173751

Family Applications (3)

Application Number Title Priority Date Filing Date
JP16090978A Granted JPS5499185A (en) 1977-12-22 1978-12-22 Photopolymerization initiator and photopolymerizable composition
JP63250739A Granted JPH01139554A (ja) 1977-12-22 1988-10-04 芳香族α−アミノケトン
JP1061101A Granted JPH01308404A (ja) 1977-12-22 1989-03-15 光重合開始剤

Family Applications Before (1)

Application Number Title Priority Date Filing Date
JP16090978A Granted JPS5499185A (en) 1977-12-22 1978-12-22 Photopolymerization initiator and photopolymerizable composition

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP1061101A Granted JPH01308404A (ja) 1977-12-22 1989-03-15 光重合開始剤

Country Status (15)

Country Link
US (4) US4318791A (ja)
EP (1) EP0003002B1 (ja)
JP (3) JPS5499185A (ja)
AR (1) AR226169A1 (ja)
AT (1) AT369392B (ja)
AU (1) AU529495B2 (ja)
BR (1) BR7808406A (ja)
CA (1) CA1234242A (ja)
DD (1) DD141320A5 (ja)
DK (1) DK157083C (ja)
FI (1) FI64169C (ja)
GR (1) GR71655B (ja)
HU (1) HU181680B (ja)
PL (1) PL117576B1 (ja)
SU (1) SU948300A3 (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8217095B2 (en) 2004-10-29 2012-07-10 Dainippon Ink And Chemicals, Inc. Active energy ray-curable ink-jet printing ink

Families Citing this family (332)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2722264C2 (de) * 1977-05-17 1984-06-28 Merck Patent Gmbh, 6100 Darmstadt Verwendung von substituierten Oxyalkylphenonen als Photosensibilisatoren
DE3107087A1 (de) * 1980-02-29 1981-12-24 CIBA-GEIGY AG, 4002 Basel "photopolymerisierbare gemische und verfahren zur photopolymerisation von kationisch polymerisierbaren verbindungen"
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US8217095B2 (en) 2004-10-29 2012-07-10 Dainippon Ink And Chemicals, Inc. Active energy ray-curable ink-jet printing ink

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ATA917678A (de) 1982-05-15
DK157083B (da) 1989-11-06
FI64169C (fi) 1983-10-10
US4315807A (en) 1982-02-16
FI64169B (fi) 1983-06-30
GR71655B (ja) 1983-06-20
FI783919A (fi) 1979-06-23
HU181680B (en) 1983-11-28
BR7808406A (pt) 1980-05-20
JPH0134242B2 (ja) 1989-07-18
JPH0257081B2 (ja) 1990-12-04
PL117576B1 (en) 1981-08-31
AU529495B2 (en) 1983-06-09
US4308400A (en) 1981-12-29
JPH01308404A (ja) 1989-12-13
EP0003002B1 (de) 1984-06-13
DK576278A (da) 1979-06-23
SU948300A3 (ru) 1982-07-30
US4321118A (en) 1982-03-23
JPH0248536B2 (ja) 1990-10-25
CA1234242A (en) 1988-03-15
US4318791A (en) 1982-03-09
EP0003002A3 (en) 1980-01-09
PL212042A1 (pl) 1979-09-10
JPS5499185A (en) 1979-08-04
EP0003002A2 (de) 1979-07-11
AU4277578A (en) 1979-06-28
AT369392B (de) 1982-12-27
DD141320A5 (de) 1980-04-23
AR226169A1 (es) 1982-06-15
DK157083C (da) 1990-03-19

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