WO2001064764A1 - Polymeres d'emulsion fortifies en resine pour encre a base d'eau et leur procede de preparation - Google Patents

Polymeres d'emulsion fortifies en resine pour encre a base d'eau et leur procede de preparation Download PDF

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Publication number
WO2001064764A1
WO2001064764A1 PCT/KR2000/000869 KR0000869W WO0164764A1 WO 2001064764 A1 WO2001064764 A1 WO 2001064764A1 KR 0000869 W KR0000869 W KR 0000869W WO 0164764 A1 WO0164764 A1 WO 0164764A1
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WO
WIPO (PCT)
Prior art keywords
water
resin
emulsion
styrene
fortified
Prior art date
Application number
PCT/KR2000/000869
Other languages
English (en)
Inventor
Hyun-Jae Ha
Seok-Heon Oh
Sae-Heun Kim
Young-Jun Park
Young-Sub Jin
Original Assignee
Hanwha Chemical Corporation
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 Hanwha Chemical Corporation filed Critical Hanwha Chemical Corporation
Publication of WO2001064764A1 publication Critical patent/WO2001064764A1/fr

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Classifications

    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/02—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of acids, salts or anhydrides
    • 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
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • 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
    • C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
    • C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof

Definitions

  • the present invention relates to a resin-fortified emulsion resin for water- borne inks and a method for preparing the same. More specifically, the present invention pertains to a resin-fortified emulsion resin having improved ink transfer efficiency and anti-foamability, and a method for synthesizing emulsion resins using water-soluble resins as emulsifiers.
  • a water-soluble resin like a conventional emulsifier, consists of a hydrophilic part and a hydrophobic part in terms of chemical structure. Accordingly, characteristics of the water-soluble resin are determined by the chemical structures of their hydrophilic part and hydrophobic part and their ratios.
  • the water-soluble resin is dissolved in water because of its hydrophilic part, but its behaviors in water are restricted by its hydrophobic part. The restriction in water makes it possible for water-soluble resins to form the aggregation of their hydrophobic parts and the aggregation is called a "micelle". Micelles are used as reaction sites for a unique emulsion polymerization reaction mechanism, in which polymers in the spherical forms are obtained.
  • the water-soluble resin employed in the polymerization reaction provides the polymerization site where emulsion polymerization can occur.
  • the water-soluble resin because of the nature of hydrophilic part, imparts structural and electrical static stability to polymer particles synthesized in such a manner.
  • the water-soluble resins are located on the surfaces of particles, compatibility between emulsion resins and pigments increases in fields of end uses such as water-borne ink.
  • the water-soluble resin has a number average molecular weight in the range of 500 to 20,000 g/mol so that the synthesized emulsion resins shows Newtonian-like flow characteristics.
  • the emulsion resins are synthesized by using conventional emulsifiers, the amount of acidic monomers is limited because of the strong hydrophilic properties of acidic monomers. Thus, the synthesized emulsion resins cannot be easily adjusted in acid number. However, in the case of using a water-soluble resin as an emulsifier, resin-fortified emulsion resins ranging from 25 to 80 in acid number can be easily synthesized by varying only the amount of the water-soluble resin. Accordingly, since the acid number is easily adjusted, physical properties of the synthesized emulsion resins such as adhesion force, compatibility with pigments, water resistance, and alcohol resistance, etc., can be efficiently adapted for the use in a variety of applications.
  • Korean Patent Laid-open No. 99-075204 discloses a preparing method for a resin-fortified emulsion with 50 % solid content in which non-ionic emulsifiers were added all at once before the initiation of emulsion polymerization reaction, and then the monomers were continuously added to a reactor to synthesize polymers.
  • the acid number of the water-soluble resin ranges from 130 to 200, and the amount of water-soluble resin used in the synthesis ranges from 18 to 24 % by weight, on the basis of monomer.
  • the acid number of final resin- fortified emulsion resins can be adjusted in the range of 25 to 50.
  • the reaction temperature is 80 °C and the monomers are used in the proportions of styrene (40%) / methyl methacylate (31%) / 2-ethyl hexyl acrylate (29%).
  • the glass transition temperature of the final synthesized polymers is 40 °C, and the viscosity is 100 cps.
  • preferred viscosity in ink preparation processes ranges from 800 to 2000cps. Therefore, additional thickeners must be used in order to increase the viscosity of emulsion resins.
  • the present inventors have done extensive research designed to prepare resin-fortified emulsion resins by use of water-soluble resins.
  • the water-soluble resins are added before the initiation of emulsion polymerization so that the water-soluble resins provide the sites where the polymerization reaction can take place.
  • a mixture comprising a non-ionic emulsifier and monomers is continuously added so that the viscosity of the emulsion resin is adjusted to the level of 1,000 cps suitable for ink preparation, without using additional thickeners or ionic emulsifiers. If an amount of water-soluble resin is adjusted, the emulsion resins with a variety of acid numbers can be obtained. Additionally, with a type and an amount of monomers varying, resins having various glass transition temperatures can be synthesized.
  • the method for preparing the resin-fortified emulsion resins through the reaction of styrene and acrylate monomers is provided, wherein styrene/acrylic water-soluble resin having an acid number of 210 to 230 is added at an amount of 20 to 35 % by weight on the basis of the monomers in advance before the initiation of emulsion polymerization reaction, and then a mixture comprising the non-ionic emulsifier and the monomers is continuously fed.
  • the present invention pertains to resin-fortified emulsion resins using water-soluble resins and a method for preparing such emulsion resins.
  • the monomer used in the present invention is styrene/acrylic monomer, and can be selected from the group consisting of acrylic acid, methacylic acid, ethyl methacylate, butyl methacylate, butyl acrylate, 2-ethyl hexyl acrylate, ethyl acrylate, hydroxy ethyl acrylate, hydroxy ethyl methacrylate and mixtures thereof.
  • styrene and 2-ethylhexyl acrylate are used in a ratio of 1 :0 to 0:1.
  • the water-soluble resin used in the present invention is styrene/acrylic water-soluble resin with the acid number of 210 to 230.
  • the resin is selected from the group consisting of styrene, alpha-methyl styrene and acrylic acid. It is desirable that the resin is used at an amount of 20 to 35 % by weight. If the amount of the water-soluble resin is less than 20 % by weight, a sufficient ink- stability cannot be obtained due to deficiency in the acid number of the resulting emulsion particles. On the other hand, if the used amount thereof exceeds 3 ' 5 % by weight, the water-soluble resins which are not adsorbed onto polymer particles and exist in water phase, may impair the stability of the resulting polymer particles.
  • the water-soluble resins are added in advance before the initiation of emulsion polymerization reaction and provide the sites where the polymerization reaction can take place. Accordingly, additional emulsifiers, especially anionic emulsifiers and thickeners are not required. However, only a small amount of the non-ionic emulsifier is used for the purpose of stabilization of the polymer particles so that resin-fortified emulsion resins with small particle sizes and high solid content can be synthesized.
  • the emulsion resins thus synthesized have superior anti-foamability and ink transfer efficiency to those of emulsion resins that are synthesized by adding the water-soluble resin simultaneously with non-ionic emulsifier as showing in U.S. pat. No. 4,820,762.
  • the non-ionic emulsifier used in the present invention is selected from the group consisting of polyethylene oxide, polypropylene oxide and mixtures thereof.
  • a mixture comprising the non-ionic emulsifier and the monomers is continuously fed to a reactor.
  • the non-ionic emulsifier is mixed in the amount of 1 to 4 parts by weight, based on 100 part by weight of monomer. If the amount thereof is less than 1 parts by weight, the resulting polymer particles have insufficient stability. On the other hand, if the emulsifier exceeds 4 parts by weight, problems associated with reduced anti-foamability and transfer efficiency can occur.
  • the non-ionic emulsifier/monomer mixture is slowly and continuously fed to the reactor for 120 to 180 minutes. It is preferred that the reaction temperature is 60 to 90 °C.
  • the final emulsion resin that is prepared through the method of the present invention has a viscosity of 800 to 2000 cps.
  • the produced emulsion resins have an acid number of 45 to 80.
  • the composition of the monomer may be easily changed so that resin-fortified emulsion resins ranging from -50 to 100 °C in glass transition temperature can be synthesized and used in a variety of applications. A better understanding of the present invention may be obtained in light of the following examples which are set forth to illustrate, but are not to be construed to limit the present invention.
  • the ratio of styrene and 2-ethylhexyl acrylate was varied freely so that the resin-fortified emulsion resins having various glass transition temperatures were prepared.
  • the physical properties of the emulsion resin such as acid number, particle size, and viscosity, were little changed.
  • Resin-fortified emulsion resins were synthesized in the same manner as Examples 1 and 3, except that 22 g of the non-ionic emulsifier, together with the water-soluble resin was simultaneously added to the reactor before the initiation of polymerization reaction.
  • the water-soluble resins provided the emulsion polymerization sites before the introduction of the emulsifiers.
  • the physical properties of polymers for example, glass transition temperature, composition, and acid number were the same or little changed, while the viscosity of the latex finally could be easily adjusted. Accordingly, the emulsion resins which are synthesized in accordance with the method of the present invention are employed in water-borne inks without additives such as additional thickeners .
  • the amount of water-soluble resin was varied in 270 to 580 g so that resin-fortified emulsion resins that have a variety of acid numbers of 45 to 80 could be prepared.
  • Polymers were synthesized in the same manner as Example 6, except that 2 wt% based on monomer ratios of an anionic emulsifier, sodium lauryl sulfate, was further used.
  • the transfer efficiency and anti-foamability of the synthesized polymers were measured through methods as follow:
  • Transfer efficiency refers to the physical property of the transferability of the ink on the substrate (primarily, paper etc.) through the roller of a printer, and is defined as the weight ratio between the amount of the inlc used and the amount of the inlc transferred on the substrate.
  • the foams attributed to the water-soluble resin and emulsifiers that are employed in emulsion polymerization are generated.
  • anti-foamability refers to the physical property of preventing foams from being generated. It is measured as follows: the prepared ink is poured into 100 ml of mass cylinder and the height of the generated foam in the cylinder is measured in relation to the period of time. The smaller the measured values, the better the anti-foamability.
  • the viscosity of the resin-fortified emulsion resins is too low to be used in water-borne ink preparations unless additives such as thickeners are employed.
  • additives such as thickeners are employed.
  • the present invention only the manner of addition of the non-ionic emulsifiers is changed so that the viscosity of the latex can be adjusted.
  • the resin-fortified emulsions are therefore used in water-borne inks preparations without any additional efforts. Because the water-soluble resin provides the reaction sites by addition thereof prior to the initiation of the emulsion polymerization reaction, the anionic emulsifiers which result in impairing the anti- foamability and transfer efficiency of water-borne inks, are not required.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polymerisation Methods In General (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne des résines d'émulsion fortifiées en résine destinées à des encres à base d'eau ainsi qu'un procédé permettant de les préparer. Lors de leur préparation, on ajoute au préalable une résine soluble dans l'eau acide styrène-acrylique avant le lancement de la polymérisation d'émulsion. La résine soluble dans l'eau fournit les sites où la réaction peut survenir comme des agents émulsifiants classiques. En conséquence, les résines d'émulsion convenant à des encres à base d'eau peuvent être réalisées sans utilisation d'émulsifiants ioniques supplémentaires. En outre, des résines d'émulsion fortifiées en résine peuvent être utilisées dans de nombreuses applications compte tenu du large éventail de leur nombre acide et température de transition vitreuse.
PCT/KR2000/000869 2000-02-28 2000-08-07 Polymeres d'emulsion fortifies en resine pour encre a base d'eau et leur procede de preparation WO2001064764A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR2000/9833 2000-02-28
KR20000009833A KR100341140B1 (ko) 2000-02-28 2000-02-28 수성 잉크용 수지 보강 에멀젼 수지 및 이의 제조방법

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102234345A (zh) * 2010-04-29 2011-11-09 上海拜道化学有限公司 一种水性油墨用环保型乳液的制备方法
JP2013537570A (ja) * 2010-07-12 2013-10-03 ハンワ ケミカル コーポレイション 伝導性塗料組成物及びそれを用いた伝導膜の製造方法
US9785063B2 (en) 2012-04-27 2017-10-10 Hewlett-Packard Indigo B.V. Liquid electrophotographic ink
US20170292026A1 (en) * 2014-08-15 2017-10-12 Basf Se Composition comprising silver nanowires and styrene/(meth)acrylic copolymers for the preparation of electroconductive transparent layers
US20180105713A1 (en) * 2015-04-09 2018-04-19 Basf Se Composition comprising silver nanowires in an alcohol/water mixture and dispersed styrene/(meth)acrylic copolymers for the preparation of electroconductive transparent layers
US10053571B2 (en) 2014-07-14 2018-08-21 Hanwha Chemical Corporation Polymer emulsion having heat sealability for blister package and preparation method thereof
EP3487895B1 (fr) 2016-07-20 2023-02-01 Basf Se Procédé de préparation d'une dispersion polymère aqueuse ayant une résistance améliorée aux produits chimiques
CN115746633A (zh) * 2022-11-14 2023-03-07 西安元创化工科技股份有限公司 一种水性ptp铝箔op保护剂及其制备方法

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101270932B1 (ko) 2010-08-05 2013-06-11 한화케미칼 주식회사 탄소소재를 이용한 고효율 방열도료 조성물
CN102702852B (zh) * 2012-06-13 2014-07-30 中山市中益油墨涂料有限公司 用于玻璃基材印刷的uv油墨及其制备方法
CN114752016B (zh) * 2022-05-12 2023-04-25 北京化工大学 一种耐乙醇稀释的核壳型自交联聚丙烯酸酯乳液及其制备方法
KR20240063757A (ko) 2022-10-31 2024-05-10 주식회사 엘엑스엠엠에이 전 아크릴계 내수성 코팅 조성물 및 이의 제조방법

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JPS62179504A (ja) * 1986-01-31 1987-08-06 Arakawa Chem Ind Co Ltd 水性フレキソインキ用樹脂バインダ−の製造方法
KR980002090A (ko) * 1996-06-20 1998-03-30 이종학 고형분 함량이 높은 수성잉크 및 수성도료용 스티렌/아크릴계 수용성 수지의 제조방법
KR19990024685A (ko) * 1997-09-05 1999-04-06 이종학 고(Ｈｉｇｈ) 고형분형 스티렌/아크릴계 수용성 수지의 제조방법
KR19990075204A (ko) * 1998-03-18 1999-10-15 이종학 수용성 수지를 이용한 수지보강 에멀젼의 중합방법

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US4839413A (en) * 1986-08-22 1989-06-13 S.C. Johnson & Son, Inc. Resin-fortified emulsion polymers and methods of preparing the same
JPH072928B2 (ja) * 1987-12-14 1995-01-18 株式会社日本触媒 コーティング剤
JP3394828B2 (ja) * 1994-12-21 2003-04-07 サカタインクス株式会社 紙用水性印刷インキ組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62179504A (ja) * 1986-01-31 1987-08-06 Arakawa Chem Ind Co Ltd 水性フレキソインキ用樹脂バインダ−の製造方法
KR980002090A (ko) * 1996-06-20 1998-03-30 이종학 고형분 함량이 높은 수성잉크 및 수성도료용 스티렌/아크릴계 수용성 수지의 제조방법
KR19990024685A (ko) * 1997-09-05 1999-04-06 이종학 고(Ｈｉｇｈ) 고형분형 스티렌/아크릴계 수용성 수지의 제조방법
KR19990075204A (ko) * 1998-03-18 1999-10-15 이종학 수용성 수지를 이용한 수지보강 에멀젼의 중합방법

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102234345A (zh) * 2010-04-29 2011-11-09 上海拜道化学有限公司 一种水性油墨用环保型乳液的制备方法
JP2013537570A (ja) * 2010-07-12 2013-10-03 ハンワ ケミカル コーポレイション 伝導性塗料組成物及びそれを用いた伝導膜の製造方法
US9785063B2 (en) 2012-04-27 2017-10-10 Hewlett-Packard Indigo B.V. Liquid electrophotographic ink
US10053571B2 (en) 2014-07-14 2018-08-21 Hanwha Chemical Corporation Polymer emulsion having heat sealability for blister package and preparation method thereof
US20170292026A1 (en) * 2014-08-15 2017-10-12 Basf Se Composition comprising silver nanowires and styrene/(meth)acrylic copolymers for the preparation of electroconductive transparent layers
US20180105713A1 (en) * 2015-04-09 2018-04-19 Basf Se Composition comprising silver nanowires in an alcohol/water mixture and dispersed styrene/(meth)acrylic copolymers for the preparation of electroconductive transparent layers
US10526501B2 (en) * 2015-04-09 2020-01-07 Basf Se Composition comprising silver nanowires in an alcohol/water mixture and dispersed styrene/(meth)acrylic copolymers for the preparation of electroconductive transparent layers
EP3487895B1 (fr) 2016-07-20 2023-02-01 Basf Se Procédé de préparation d'une dispersion polymère aqueuse ayant une résistance améliorée aux produits chimiques
CN115746633A (zh) * 2022-11-14 2023-03-07 西安元创化工科技股份有限公司 一种水性ptp铝箔op保护剂及其制备方法
CN115746633B (zh) * 2022-11-14 2024-04-02 西安元创化工科技股份有限公司 一种水性ptp铝箔op保护剂及其制备方法

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Publication number Publication date
KR100341140B1 (ko) 2002-06-20
KR20010084640A (ko) 2001-09-06

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