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WO2009068865A1 - Nouvelles résines appropriées pour des encres d'impression et des vernis - Google Patents

Nouvelles résines appropriées pour des encres d'impression et des vernis Download PDF

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Publication number
WO2009068865A1
WO2009068865A1 PCT/GB2008/003934 GB2008003934W WO2009068865A1 WO 2009068865 A1 WO2009068865 A1 WO 2009068865A1 GB 2008003934 W GB2008003934 W GB 2008003934W WO 2009068865 A1 WO2009068865 A1 WO 2009068865A1
Authority
WO
WIPO (PCT)
Prior art keywords
dammar
product according
glycol
oil
resin
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/GB2008/003934
Other languages
English (en)
Inventor
Martin John Thompson
Douglas Frederick Pavey
Louis Papaspyrou
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.)
Sun Chemical Ltd
Original Assignee
Sun Chemical Ltd
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 Sun Chemical Ltd filed Critical Sun Chemical Ltd
Publication of WO2009068865A1 publication Critical patent/WO2009068865A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
    • 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
    • C09D11/08—Printing inks based on natural resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/08—Polyesters modified with higher fatty oils or their acids, or with resins or resin acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
    • C08L93/04—Rosin
    • 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
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
    • 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
    • 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
    • C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
    • C09D11/104—Polyesters
    • C09D11/105—Alkyd resins
    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
    • 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
    • C09D193/00—Coating compositions based on natural resins; Coating compositions based on derivatives thereof
    • 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
    • C09D193/00—Coating compositions based on natural resins; Coating compositions based on derivatives thereof
    • C09D193/04—Rosin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L93/00—Compositions of natural resins; Compositions of derivatives thereof

Definitions

  • the present invention relates to novel resins which incorporate dammar batu or similar gums, which can be used for printing inks and varnishes, and which are of particular use for offset printing, although they can also be used, with advantage, in printing inks for printing by other methods.
  • Oleoresinous varnishes which are blends or reaction products of drying oils with resins, have been known since at least the early twentieth century [see, for example, "Coating and Ink Resins: A Technological Study” by W. Krumbhaar, published by Reinhold Publishing Corporation in 1947].
  • the simplest consist merely of an oil cooked with a resin, the reaction product of linseed oil with rosin being an example of this.
  • a resole into the formulation has brought many advantages, such as the ability to increase the molecular weight of the resin while retaining its solubility.
  • Resoles are prepared from phenol or a derivative thereof, such as an alkylphenol, and formaldehyde. There is however growing concern over the health and safety and environmental acceptability of these reagents.
  • the alkylphenols are generally endocrine disruptors, t-butylphenol being harmful and corrosive, while formaldehyde is toxic and corrosive and a possible carcinogen.
  • dammar resin preferably of a fossil grade such as dammar batu.
  • dammar gums Further information on the dammar gums can be found in The Chemistry of Dammar Resin. J.S. Mills and A.E.A. Werner. Journal of the Chemical Society, 1955, pp 3132-3140 and "Printing Ink Technology" by E.A. Apps, published in 1958 by Leonard Hill
  • the present invention consists in the reaction product of rosin modified with an ethylenically unsaturated polybasic acid and a further resin, the modified resin being esterified with a polyol, characterised in that the further resin is a dammar resin, preferably a fossil grade of dammar gum.
  • Rosin is a well-known, commercially available material. Chemically, it is mainly a mixture of C20 tricyclic fused-ring, mono-carboxylic acids, typically abietic acid. Various grades of rosin are available and may be used, including wood rosin, gum rosin and tall oil rosin. Rosin may be obtained from a number of countries, including the US, Canada, Portugal, China, Greece, Brazil, Spain and the Scandinavian countries, and there will be minor variations in properties between the different grades and the same grade from different countries. However, these are well known in the art and the skilled person knows well the adjustments that need be made to accommodate the different grades and nationalities of rosin.
  • rosin refers to rosin from any source, including tall oil rosin, gum rosin and wood rosin, or country.
  • the term “rosin” also includes treated rosin, which may have been treated, for example, by disproportionation and/or hydrogenation reactions.
  • the term “rosin” also includes dimerised rosin. These materials are all well known in the art, as is their use in coating compositions, such as printing inks and varnishes. Rosin is typically characterized by its acid number, and rosins having acid numbers ranging from about 160 to about 180 mg KOH/ gram are preferred for use in the present invention.
  • the ethylenically unsaturated polybasic acid or derivative thereof is a compound capable of undergoing a Diels-Alder reaction with the rosin. Such compounds are well known in the art and any commonly used in the art may equally be used in the present invention.
  • suitable ethylenically unsaturated polybasic acids include: maleic acid, fumaric acid and itaconic acid (methylenesuccinic acid), of which maleic acid is preferred.
  • appropriate reactive derivatives of the acids such as the anhydrides or reactive esters, e.g. methyl and ethyl esters, may be used.
  • suitable polyols include ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, trimethylene glycol, glycerol, 2,2-propanediol, polyethylene glycol, polypropylene glycol, polybutylene glycol, trimethylolpropane, di-trimethylolpropane, pentaerythritol, dipentaerythritol, tripentaerythritol, trimethylolethane, trimethylolpropane, mannitol and sorbitol, of which pentaerythritol is preferred.
  • Dammar is the name given to a group of resins obtained from trees of the Dipterocarpaceae family. Fresh dammar gum is obtained directly from the trees. However, this invention preferably uses the fossil grades of dammar, which are commonly said to be obtained from the ground, but are actually obtained from the region of the roots of the trees. Several types of so-called semi-fossil dammars are known, such as Daging, Batu, Sengai and Hitam, and any of these may be used in the present invention. However, the preferred dammar resins used are dammar batu. Surprisingly, these grades of dammar gum can act as a direct replacement for the resole resins and have the advantage of eliminating from use such unpleasant materials as the alkylphenols and formaldehyde.
  • the fossil grades of these gums are derived from fresh gums by natural processes, which can be replicated synthetically, and so the terms "fossil” and "semi- fossil” cover such grades of gum whether derived by natural or synthetic processes.
  • the preferred order of reaction is rosin plus polybasic acid, then add the dammar gum and finally add the polyol. Since the first of these reactions has an optimum reaction temperature lower than that of the second and third reactions and the second reaction has an optimum reaction temperature lower than that of the third reaction, this reaction order allows the reactions to be carried out, as is preferred, as a one pot reaction (i.e.
  • dammar gum is a straight replacement for the resole used in the prior art, any order of reaction used in the prior art may equally be used here.
  • reaction may be carried out in the presence of a solvent, if desired.
  • a solvent such as xylene, may be used as the solvent.
  • a solvent will not be needed, and is therefore best avoided.
  • the temperature at which the reactions are carried out is not critical to of the present invention. In general, the reactions are carried out at temperatures within the range from 180 to 270°C. However, as noted above, the reactions are preferably carried out at steadily increasing temperatures, as is well known in the art.
  • the reaction of the rosin with the polybasic acid may take place at a temperature in the range from 180 to 190°C; the reaction of this product with the dammar gum may take place at a temperature from 200 to 250 0 C; and the reaction with the polyol may take place at a temperature in the range from 250 to 27O 0 C.
  • the final reaction that with the polyol, is carried out until the desired acid value, preferably from 15 to 50 mg KOH/ gram, more preferably from 15 to 30 mg KOH/ gram, is achieved.
  • the proportions of the various reagents may vary widely, as is known for the comparable resole-based resins. However, in general, we prefer from 30 to 80%, more preferably from 45 to 60%, by weight of rosin; from 1 to 10%, more preferably from 4 to 6%, by weight of polybasic acid; from 10 to 40%, more preferably from 25 to 35%, by weight of dammar gum; and from 5 to 20%, more preferably from 7 to 15%, of polyol.
  • the resulting resins may be used for the formulation of various coating compositions, particularly inks and varnishes, as a direct replacement for the known resole-based resins.
  • the present invention also provides a coating composition
  • a coating composition comprising a resin of the present invention and a solvent therefor, and optionally a colorant, such as a pigment or dye.
  • the invention further provides a coating method in which a substrate is coated with a coating composition of the present invention.
  • the solvent may be any such material used in the prior art.
  • a drying oil such as linseed oil, tung oil, poppy seed oil, perilla oil or walnut oil, is preferred.
  • those formulations which are rich in semi-drying oils may have sufficient drying potential to exclude the need for a drying oil.
  • solvents examples include the alkyl esters of semi-drying oils such as soya, rapeseed, sunflower, peanut, sesame and safflower oil, preferably the methyl esters (e.g. methyl soyate), including also those solvents derived from mixed vegetable esters solvents (e.g. of rapeseed, soya and palm ), which may include small proportions ofnon drying oils.
  • semi-drying oils such as soya, rapeseed, sunflower, peanut, sesame and safflower oil
  • methyl esters e.g. methyl soyate
  • solvents derived from mixed vegetable esters solvents e.g. of rapeseed, soya and palm
  • solvents which may be used include a mineral oil distillate preferably having a boiling range within the limits 200°C - 320°C, and toluene.
  • composition of the present invention is to be used as an ink, it will include a pigment or dye. There is no restriction on the nature of these, and any such material commonly used in the prior art may equally be used here.
  • the coating compositions of the present invention are especially suited for varnishes and inks, especially printing inks, including lithographic inks and especially inks for use in offset litho printing.
  • These typically comprise, as additional components to those referred to above, one or more of stabilisers, plasticisers, pigments, waxes, slip aids, levelling aids, adhesion promoters, surfactants and fillers, for example as described in "Printing Ink Manual", fourth edition, Leach R. H. et al (eds.), Van Nostrand Reinhold, Wokingham, (1988), the disclosure of which is incorporated herein by reference.
  • a manufacturing loss of 5% by weight is expected.
  • the resin was manufactured by heating the gum rosin to 180°C under an atmosphere of inert gas (nitrogen) and then reacting it via a Diels Alder reaction with the maleic anhydride. The temperature was raised to 200°C, and dammar batu was added portionwise. After 1 A hour at 200°C, the temperature is raised to 210°C, and pentaerythritol was added. Esterification was carried out at 260°C until an acid value below 30mg KOH/ gram was achieved.
  • inert gas nitrogen
  • Viscotek 250 Dual detector which includes refractive index and viscometry.
  • Linseed oil (alkali refined) 12.4%
  • An offset ink was prepared using a varnish prepared as described in Example 7, with the resin of Example 1.
  • Hydrocarbon distillate (aromatic content 3.5% -1%; bp range 240°-270°C)
  • Example 9 ink was found to have drying properties similar to the standard inks to which it was compared.

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

Abstract

L'invention porte sur un produit de réaction de colophane modifiée par un acide polyvalent à insaturation éthylénique et d'une autre résine, la résine modifiée étant estérifiée par un polyol. Ce produit peut être utilisé comme composant principal d'une encre ou d'un vernis. L'autre résine, de façon classique un résol, est remplacée par une résine dammar, de préférence une telle résine de qualité fossile.
PCT/GB2008/003934 2007-11-27 2008-11-25 Nouvelles résines appropriées pour des encres d'impression et des vernis Ceased WO2009068865A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0723219.2 2007-11-27
GB0723219A GB2455093A (en) 2007-11-27 2007-11-27 Novel resins suitable for printing inks and varnishes

Publications (1)

Publication Number Publication Date
WO2009068865A1 true WO2009068865A1 (fr) 2009-06-04

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PCT/GB2008/003934 Ceased WO2009068865A1 (fr) 2007-11-27 2008-11-25 Nouvelles résines appropriées pour des encres d'impression et des vernis

Country Status (2)

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GB (1) GB2455093A (fr)
WO (1) WO2009068865A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110066599A (zh) * 2019-05-09 2019-07-30 闽江学院 食品级漆酚基桐油复合涂料及其制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1950467B (zh) * 2004-04-22 2010-05-05 大日本油墨化学工业株式会社 平版油墨清漆用改性松香酯树脂组合物的制造方法及平版油墨清漆的制造方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2197047A (en) * 1939-01-07 1940-04-16 Hercules Powder Co Ltd Coating composition
GB1166249A (en) * 1965-09-21 1969-10-08 Vianova Kunstharz Ag Electrophoretic Coating Process.
US4250066A (en) * 1980-01-07 1981-02-10 Inmont Corporation Modified phenolic resinates and inks
EP0041838A2 (fr) * 1980-06-05 1981-12-16 Dainippon Ink And Chemicals, Inc. Compositions de résines phénoliques modifiées par des résines naturelles/acides résiniques ainsi que leur préparation
US5073623A (en) * 1988-09-14 1991-12-17 Basf Lacke+Farben Aktiengesellschaft Condensation products based on rosin
JP2004155908A (ja) * 2002-11-06 2004-06-03 Arakawa Chem Ind Co Ltd ポリエステル樹脂、その製造法、印刷インキ用バインダーおよび印刷インキ

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GB645914A (en) * 1947-08-13 1950-11-08 British Cellophane Ltd Improvements in or relating to moistureproofing heat-sealing coating compositions, and in or relating to articles coated therewith
US2819983A (en) * 1954-02-01 1958-01-14 Eastman Kodak Co Wood finishing lacquer systems
DE19831141C2 (de) * 1998-07-11 2003-02-27 Dmc2 Degussa Metals Catalysts Edelmetallpräparat und dessen Verwendung zur Herstellung von Edelmetalldekoren durch Direkt- und Indirektdruck
DE10050949A1 (de) * 2000-10-13 2002-04-18 Dmc2 Degussa Metals Catalysts Edelmetallpräparat und dessen Verwendung zur Herstellung von Edelmetalldekoren durch Direkt- und Indirektdruck

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2197047A (en) * 1939-01-07 1940-04-16 Hercules Powder Co Ltd Coating composition
GB1166249A (en) * 1965-09-21 1969-10-08 Vianova Kunstharz Ag Electrophoretic Coating Process.
US4250066A (en) * 1980-01-07 1981-02-10 Inmont Corporation Modified phenolic resinates and inks
EP0041838A2 (fr) * 1980-06-05 1981-12-16 Dainippon Ink And Chemicals, Inc. Compositions de résines phénoliques modifiées par des résines naturelles/acides résiniques ainsi que leur préparation
US5073623A (en) * 1988-09-14 1991-12-17 Basf Lacke+Farben Aktiengesellschaft Condensation products based on rosin
JP2004155908A (ja) * 2002-11-06 2004-06-03 Arakawa Chem Ind Co Ltd ポリエステル樹脂、その製造法、印刷インキ用バインダーおよび印刷インキ

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 200449, Derwent World Patents Index; AN 2004-509652, XP002513855 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110066599A (zh) * 2019-05-09 2019-07-30 闽江学院 食品级漆酚基桐油复合涂料及其制备方法

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GB2455093A (en) 2009-06-03
GB0723219D0 (en) 2008-01-09

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