WO2011042225A1 - A polymer washout solvent, and the use thereof for developing a flexographic printing plate - Google Patents

A polymer washout solvent, and the use thereof for developing a flexographic printing plate Download PDF

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Publication number
WO2011042225A1
WO2011042225A1 PCT/EP2010/058008 EP2010058008W WO2011042225A1 WO 2011042225 A1 WO2011042225 A1 WO 2011042225A1 EP 2010058008 W EP2010058008 W EP 2010058008W WO 2011042225 A1 WO2011042225 A1 WO 2011042225A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrocarbon component
solvent
alcoholic
polymer
washout solvent
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.)
Ceased
Application number
PCT/EP2010/058008
Other languages
English (en)
French (fr)
Inventor
Figen Aydogan
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.)
FLEXOCLEAN ENGINEERING BV
Original Assignee
FLEXOCLEAN ENGINEERING BV
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 FLEXOCLEAN ENGINEERING BV filed Critical FLEXOCLEAN ENGINEERING BV
Priority to CN201080029175.5A priority Critical patent/CN102472983B/zh
Priority to US13/378,328 priority patent/US8921035B2/en
Priority to JP2012532504A priority patent/JP5739893B2/ja
Priority to RU2012118570/05A priority patent/RU2523810C2/ru
Priority to CA2763951A priority patent/CA2763951C/en
Publication of WO2011042225A1 publication Critical patent/WO2011042225A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26Processing photosensitive materials; Apparatus therefor
    • G03F7/30Imagewise removal using liquid means
    • G03F7/32Liquid compositions therefor, e.g. developers
    • G03F7/325Non-aqueous compositions

Definitions

  • a polymer washout solvent, and the use thereof for developing a flexographic printing plate are provided.
  • the present invention relates to a polymer washout solvent and the use thereof for developing a flexographic printing plate .
  • flexographic printing plates are flexible, polymeric plates which have a relief corresponding to an image to be printed.
  • the relief is present on top of a basic layer.
  • photopolymerizable material which can be hardened under influence of light.
  • the front side of the plate is exposed to UV/A light according to a certain pattern. This is usually done by applying at the front side a mask with openings which is the negative of the pattern to be printed. The light passing through the openings of the mask thus hardens specific regions of the front side of the plate.
  • the not hardened regions can be removed in various ways, to obtain a so called developed flexographic plate. Usually the removal of not hardened polymer is performed by washing the plate in a solvent, a so called polymer washout solvent.
  • Nylosolv A was introduced in 1988 to substitute earlier solvents based on perchloroethylene (a CFC, an
  • a major ingredient (25- 50 wt%) in Nylosolv A is a heavy fraction of hydrated distillate of mineral oil. Also Haku (obtained from Kluthe) contains such a heavy fraction distillate (50-100 wt%, including aromatics) . This
  • naphta is classified as hazardous.
  • Nylosolv A contains cyclohexanol (25-50 wt.%) and m-diisopropyl benzene (10-25 wt%) .
  • Haku contains benzylalcohol (10-25wt.%). These components are also classified as hazardous.
  • Biesterveld B.V. which contains heavy fraction distillate and benzylalcohol.
  • the known solvents are hazardous compositions, and are harmful in the sense that they present a threat to man and environment. For that reason, it is not allowed to keep in stock large amounts of these solvents, unless strict and cost-consuming measures are taken to prevent any accidents. Besides these unwanted properties, the solvents have an unpleasant odor. This unpleasant odor is also transmitted to the printing plates after washing with the solvent, which compromises the quality of the end-product. Furthermore, different sheets of soft photopolymerizable material, require different types of washout solvent to achieve the best washout result.
  • washout solvent should be able to achieve a similar result in regard of the
  • the objective of the invention is to provide a less hazardous and less harmful polymer washout solvent which achieves at the same time one or more of the above indicated goals.
  • a polymer washout solvent for developing a flexographic printing plate which comprises:
  • the washout solvent contains no heavy fraction
  • distillates i.e. naphta
  • the solvent - as will be shown below - achieves a reduction of the time needed when washing and drying a flexographic plate.
  • the solvent of the invention is only slightly absorbed in hardened regions so that swelling during the washing step is absent or very low. Obviously, this has a positive effect on the subsequent drying time, in that the time needed is reduced.
  • the solvent is suitable for a wide range of different soft photopolymerizable materials, it is not longer required to keep stocks of different washout solvents, as they can be replaced by the single washout solvent of the invention.
  • the solvent is a stable mixture, as it showed no precipitation effects during normal shelf life.
  • the solvent is after use as wash-out solvent, fit for re-use by distilling off used solvent (regeneration) , because no major adjustments to the specific ratio of the components in the distilled solvent are needed. Furthermore, because of the relatively low number of components, the solvent is easily adjusted, if needed.
  • Nylosolv is to be regenerated sooner, as it shows precipitation of particles of washed out polymer. This indicates that the solvent of the invention has a higher solubility value for the polymers to be washed out than known solvents.
  • the solvent of the invention comprises
  • ester hydrocarbon component comprises a compound chosen from the group of ester compounds of a C1-C5 alkyl, a benzyl or a benzyl derivative and a C1-C5 alkanoate, as well as mixtures of these ester compounds.
  • the C1-C5 groups may be branched or straight hydrocarbons, and preferred are straight
  • the ester hydrocarbon component includes acetate as alkanoate, and preferably benzyl or a benzylderivat ive .
  • the ether hydrocarbon component comprises a di- ether of an C1-C8 alkane derived from a diol, and two C1-C3 alkoxy groups .
  • the ether hydrocarbon component comprises a di-ether of an alkane having an internal ether group, and preferably two methoxy groups.
  • a di-ether such as dipropylene glycol dimethyl ether.
  • alcoholic hydrocarbon component comprises a compound chosen from the group of C1-C10 alcoholic compounds, as well as mixtures of these alcoholic compounds.
  • the C1-C10 groups may be branched or straight hydrocarbons. Again, such solvents prove to be effective in achieving the goals of the
  • the alcoholic hydrocarbon component Preferably, the alcoholic hydrocarbon component
  • alcoholic group is present, and more preferably the
  • hydrocarbon chain is straight.
  • n- butanol and/or n-pentanol are especially preferred.
  • a solvent of the invention wherein the alcoholic hydrocarbon component comprises a compound containing a secondary alcoholic group, possibly also containing an ether group.
  • the alcoholic compound is a propanol, preferably propan-2-ol and/or l-methoxypropan-2-ol .
  • the washout solvent according to the invention contains additives for improving the odor of the solvent.
  • additives for improving the odor of the solvent for example known fragrances are used to mask any unwanted odor from the solvent.
  • D-Limonene is used as an additive.
  • the invention relates to the use of a polymer washout solvent according to the invention, for developing a flexographic printing plate in a washing step.
  • a polymer washout solvent according to the invention for developing a flexographic printing plate in a washing step.
  • the developing of a flexographic printing plate becomes less time consuming, in regard of the washing step, as well as the subsequent drying step.
  • Example below shows a polymer washout solvent according to the invention, and its use for developing a flexographic printing plate.
  • the obtained mixture, a washout solvent according to the invention has a boiling point of 116°C, a flash point of 48°C and a density of 0,92 kg/liter.
  • the solvent is
  • the washout solvent was used in a wash-out apparatus
  • the time needed for the subsequent drying step was 15- 30 minutes, which is a reduction by 1.5 to 2 hours compared to using a known solvent.
  • the used solvent with the washed off non-hardened polymer was distilled off to recover the solvent.
  • the distilled solvent showed to have a ratio of components similar to the solvent before use, and is thus regenerable without the need of major adjustments to the relative amounts of the components.
  • known solvents need major adjustment of the relative amounts of the components, after distilling off after their use.
  • the components have to be added in specific amounts to the distillate in order to obtain a suitable regenerated washout solvent for re-use. According to specific tables the amounts to be added have to be calculated in order to regenerate the solvent correctly.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Printing Plates And Materials Therefor (AREA)
  • Manufacture Or Reproduction Of Printing Formes (AREA)
  • Detergent Compositions (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Printing Methods (AREA)
PCT/EP2010/058008 2009-10-09 2010-06-08 A polymer washout solvent, and the use thereof for developing a flexographic printing plate Ceased WO2011042225A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN201080029175.5A CN102472983B (zh) 2009-10-09 2010-06-08 聚合物冲洗溶剂及其用于显影柔性印刷版的用途
US13/378,328 US8921035B2 (en) 2009-10-09 2010-06-08 Polymer washout solvent, and the use thereof for developing a flexographic printing plate
JP2012532504A JP5739893B2 (ja) 2009-10-09 2010-06-08 フレキソ印刷版を現像するためのポリマーウォッシュアウト溶剤、およびその使用
RU2012118570/05A RU2523810C2 (ru) 2009-10-09 2010-06-08 Растворитель для вымывания полимера и его применение для обработки флексографической печатной формы
CA2763951A CA2763951C (en) 2009-10-09 2010-06-08 A polymer washout solvent, and the use thereof for developing a flexographic printing plate

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP09172718A EP2309331B1 (en) 2009-10-09 2009-10-09 A polymer washout solvent and the use thereof for developing a flexographic printing plate
EP09172718.0 2009-10-09

Publications (1)

Publication Number Publication Date
WO2011042225A1 true WO2011042225A1 (en) 2011-04-14

Family

ID=41508761

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2010/058008 Ceased WO2011042225A1 (en) 2009-10-09 2010-06-08 A polymer washout solvent, and the use thereof for developing a flexographic printing plate

Country Status (16)

Country Link
US (1) US8921035B2 (https=)
EP (1) EP2309331B1 (https=)
JP (1) JP5739893B2 (https=)
CN (1) CN102472983B (https=)
AT (1) ATE543124T1 (https=)
CA (1) CA2763951C (https=)
CY (1) CY1112700T1 (https=)
DK (1) DK2309331T3 (https=)
HR (1) HRP20120094T1 (https=)
PL (1) PL2309331T3 (https=)
PT (1) PT2309331E (https=)
RS (1) RS52204B (https=)
RU (1) RU2523810C2 (https=)
SI (1) SI2309331T1 (https=)
WO (1) WO2011042225A1 (https=)
ZA (1) ZA201205692B (https=)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8632961B2 (en) * 2010-01-28 2014-01-21 Eastman Kodak Company Flexographic processing solution and use
US8349185B2 (en) * 2010-10-20 2013-01-08 E I Du Pont De Nemours And Company Method for rebalancing a multicomponent solvent solution
CA2914134A1 (en) * 2013-06-14 2014-12-18 Flint Group Germany Gmbh Flexographic printing element which can be digitally imaged and has a polar, ultra-thin barrier layer
JP2021525388A (ja) * 2018-05-25 2021-09-24 ビーエイエスエフ・ソシエタス・エウロパエアBasf Se 50nm以下のライン間寸法を有するパターン化材料を処理したときのパターン倒壊を回避するための溶媒混合物を含む組成物を使用する方法
CN109706007A (zh) * 2018-12-18 2019-05-03 珠海顺泽科技股份有限公司 一种印刷网板清洗液组合物

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57108851A (en) * 1980-12-25 1982-07-07 Nec Corp Formation of resist image
EP0355789A2 (en) * 1988-08-23 1990-02-28 E.I. Du Pont De Nemours And Company Process for the production of flexographic printing reliefs
US5354645A (en) * 1988-08-23 1994-10-11 E. I. Du Pont De Nemours And Company Process for the production of flexographic printing reliefs
EP1085003A1 (en) * 1999-03-31 2001-03-21 DAICEL CHEMICAL INDUSTRIES, Ltd. High-purity 1,3-propanediol derivative solvent, process for producing the same, and use thereof
WO2002061506A2 (de) * 2001-01-29 2002-08-08 Basf Drucksysteme Gmbh Entwicklerflüssigkeit enthaltend dipropylenglycoldialkylether
WO2003046666A1 (en) * 2001-11-27 2003-06-05 Nupro Technologies, Inc. Developing solvent for photopolymerizable printing plates
US20060040218A1 (en) * 2004-08-18 2006-02-23 Wyatt Marion F Terpene ether solvents

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Publication number Priority date Publication date Assignee Title
JPH0625865B2 (ja) * 1985-09-27 1994-04-06 三菱製紙株式会社 カラー画像記録材料
DE3807929A1 (de) * 1988-03-10 1989-09-28 Basf Ag Verfahren zur herstellung von reliefformen
DE4020372A1 (de) * 1990-06-27 1992-01-02 Basf Ag Verfahren zur herstellung photopolymerer flexographischer reliefdruckplatten
DE4020373A1 (de) * 1990-06-27 1992-01-02 Basf Ag Verfahren zur herstellung photopolymerer flexographischer reliefdruckplatten
JPH05249695A (ja) * 1991-11-15 1993-09-28 Asahi Chem Ind Co Ltd 感光性エラストマー組成物の現像剤及びそれを用いた製版方法
JP3233708B2 (ja) * 1992-12-10 2001-11-26 日本電子精機株式会社 感光性フレキソ版溶出剤及び印刷用洗浄剤
AU2102499A (en) * 1998-01-09 1999-07-26 Nupro Technologies, Inc. Developer solvent for photopolymer printing plates and method
JP2004538517A (ja) 2001-08-03 2004-12-24 ビーエーエスエフ ドルクズュステーメ、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツング 感光性フレキソ印刷材料、及び新聞用フレキソ印刷版の製造方法
ITMI20031131A1 (it) * 2003-06-05 2004-12-06 Omet Srl Metodo e dispositivo per la pulizia di un cilindro di
US20100068651A1 (en) * 2008-09-16 2010-03-18 Bradford David C Developing solution for flexographic printing plates
US8632961B2 (en) * 2010-01-28 2014-01-21 Eastman Kodak Company Flexographic processing solution and use

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57108851A (en) * 1980-12-25 1982-07-07 Nec Corp Formation of resist image
EP0355789A2 (en) * 1988-08-23 1990-02-28 E.I. Du Pont De Nemours And Company Process for the production of flexographic printing reliefs
US5354645A (en) * 1988-08-23 1994-10-11 E. I. Du Pont De Nemours And Company Process for the production of flexographic printing reliefs
EP1085003A1 (en) * 1999-03-31 2001-03-21 DAICEL CHEMICAL INDUSTRIES, Ltd. High-purity 1,3-propanediol derivative solvent, process for producing the same, and use thereof
WO2002061506A2 (de) * 2001-01-29 2002-08-08 Basf Drucksysteme Gmbh Entwicklerflüssigkeit enthaltend dipropylenglycoldialkylether
WO2003046666A1 (en) * 2001-11-27 2003-06-05 Nupro Technologies, Inc. Developing solvent for photopolymerizable printing plates
US20060040218A1 (en) * 2004-08-18 2006-02-23 Wyatt Marion F Terpene ether solvents

Also Published As

Publication number Publication date
HRP20120094T1 (hr) 2012-02-29
CA2763951A1 (en) 2011-04-14
PT2309331E (pt) 2012-02-23
CY1112700T1 (el) 2016-02-10
SI2309331T1 (sl) 2012-04-30
ATE543124T1 (de) 2012-02-15
JP2013507644A (ja) 2013-03-04
RU2012118570A (ru) 2013-11-20
DK2309331T3 (da) 2012-05-21
US20120196231A1 (en) 2012-08-02
RU2523810C2 (ru) 2014-07-27
ZA201205692B (en) 2013-04-24
EP2309331B1 (en) 2012-01-25
EP2309331A1 (en) 2011-04-13
CN102472983A (zh) 2012-05-23
RS52204B (sr) 2012-10-31
JP5739893B2 (ja) 2015-06-24
US8921035B2 (en) 2014-12-30
CA2763951C (en) 2014-08-05
PL2309331T3 (pl) 2012-07-31
CN102472983B (zh) 2017-07-21

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