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WO1998046689A1 - Encre d'impression ou liants de revetement durcissables a faible emission - Google Patents

Encre d'impression ou liants de revetement durcissables a faible emission Download PDF

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Publication number
WO1998046689A1
WO1998046689A1 PCT/EP1998/002085 EP9802085W WO9846689A1 WO 1998046689 A1 WO1998046689 A1 WO 1998046689A1 EP 9802085 W EP9802085 W EP 9802085W WO 9846689 A1 WO9846689 A1 WO 9846689A1
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WO
WIPO (PCT)
Prior art keywords
component
printing
binder
ink
solvent
Prior art date
Application number
PCT/EP1998/002085
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English (en)
Inventor
Rainer Blum
Dietmar Chmielewski
Original Assignee
Ppg Industries Ohio, Inc.
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 Ppg Industries Ohio, Inc. filed Critical Ppg Industries Ohio, Inc.
Priority to EP98919249A priority Critical patent/EP0975702A1/fr
Priority to AU72156/98A priority patent/AU7215698A/en
Priority to CA002280849A priority patent/CA2280849A1/fr
Publication of WO1998046689A1 publication Critical patent/WO1998046689A1/fr

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Classifications

    • 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
    • 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
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
    • 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
    • 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
    • C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D177/12—Polyester-amides

Definitions

  • the invention relates to low-emission, curable binders for coatings or printing inks, to processes for their preparation, to coating materials and printing inks comprising them, to polyesters used for their preparation, and to the use thereof for coating, printing and/or impregnating substrates or shaped articles, especially metallic vessels, packaging or parts thereof.
  • the coating or coloring of different shaped articles and packaging is carried out using low-solvent or solvent-free coatings binders based on oligomeric polyesters.
  • curable hydroxy resin compositions which consist of hydroxyl -containing polyesters, polyglycol monoethers, amino resins and catalysts. Customary commercial polyesters are employed.
  • polyglycol monoether use is made, for example, of propylene glycol monomethyl ether.
  • DE-A-2721989 describes liquid coating compositions with a low-solvent or solvent-free base. They comprise amino resins and at least bifunctional polyesters which are built up from polyols and dicarboxylic acids.
  • EP-B-0 002 718 describes the use of a coating material based on epoxy resin and on a trimellitic anhydride ester mixture for the interior coating of metal containers for foodstuffs or beverages.
  • a diester is prepared from trimellitic anhydride and ethylene glycol and is dissolved, together with an epoxy resin, in an organic solvent.
  • Low-solvent or solvent-free coating materials and printing inks have not met the technical requirements placed on them. When used in conjunction with metal packaging, especially for foodstuffs, they are required to exhibit high levels of adhesion, abrasion resistance, deformability and sterilizability, since beverage cans,' for example, after coating or printing are filled, shaped and sterilized under hot conditions. In the course of coating or printing the articles, the solvent employed in the coating materials and printing inks used to date escapes and can in general not be recovered. However, for reasons of environment and economics there is a need for low-solvent or solvent-free coating materials and printing inks.
  • polyesters from 30 to 98* by weight of polyesters, as component A, which can be prepared by reacting
  • al3 at least one monofunctional hydroxy compound and/or amino compound and/or monocarboxylic acid as component A13,
  • component A12 being employed in an excess of equivalents relative to All, so that hydroxyl- and/or amino-terminated oligomers are formed even in the case of complete condensation
  • a2 at least one polyanhydride compound having at least two carboxylic anhydride groups, as component A2,
  • a3 at least one monoanhydride of a polycarboxylic acid, as component A3,
  • polyesters used to date are generally solid or of very high viscosity and have to be dissolved in organic solvents.
  • the known crossl inkable polyesters which are liquid at room temperature have a limited degree of condensation. They are linear or branched and carry terminal functional groups. They are crossl inked by way of these terminal functionalities.
  • the printing-ink or coatings binders provided in accordance with the invention include, as component A, polyesters which are functionalized in the molecule chain and not just terminally.
  • Component A is present in the novel low-solvent or solvent-free printing- ink or coatings binders in an amount of from 30 to 98, preferably from 40 to 90 and, in particular, from 60 to 90* by weight.
  • polyesters of component A can be prepared by reacting a mixture of the following components Al, A2 and, if desired, A3.
  • Component Al is a mixture of the following components Al, A2 and, if desired, A3.
  • Components Al are hydroxyl- and/or amino-terminated oligomers which are built up from the following components All, A12 and, if desired, A13.
  • Suitable polyfunctional carboxylic acids are di-, tri- and higher polybasic carboxylic acids, preferably dicarboxylic acids. Depending on the desired properties the polyfunctional carboxylic acid can be aliphatic, aromatic or mixed aliphatic/aromatic. Examples of suitable polyfunctional carboxylic acids are phthalic acid in its isoeric forms and linear, terminal C 3 . 12 -, preferably C 4 . 10 -alkylenedicarboxylic acids, especially adipic acid.
  • acids examples include suberic acid, tetrahydrophthalic acid, endomethylenetetrahydrophthalic acid, hexahydrophthalic acid, fumaric acid, maleic acid, itaconic acid, citraconic acid, tri ellitic acid and pyromellitic acid.
  • Components A12 are at least one polyfunctional hydroxy compound and/or amino compound.
  • the polyfunctional hydroxy compound and/or amino compound in this case has 2 or more, preferably 2 to 4, hydroxyl and/or amino groups.
  • Examples of compounds suitable as component A12 are linear aliphatic terminal diols, such as C 2 . 12 -. preferably C 2 . 6 -diols, especially ethylene glycol and 1,6-hexanediol . It is also possible to employ aromatic or mixed aromatic/aliphatic hydroxy and/or amino compounds.
  • alkoxylated OH-functional substances such as the ethoxylation and propoxyl ation products of the above-described polyols, and also polyalkylene oxide polyols, polytetrahydrofurandiols and polycaprol actonediol s.
  • component A13 there may be present as component A13, if desired, at least one monofunctional hydroxy compound and/or amino compound and/or monocarboxylic acid.
  • amide and imide structures is also possible. This is described, for example, in DE-A-1570273 and DE-A-1720323.
  • suitable starting materials it is possible to alter the properties of the hydroxyl - and/or amino-terminated oligomers.
  • unbranched compounds such as hexanediol or adipic acid
  • branched compounds such as neopentyl glycol
  • aromatic compounds such as isomers of phthalic acid, or hydrogenated bisphenol A, leads to end products which are more scratch-resistant and temperature-stable.
  • the starting materials can be selected in accordance with these generally known aims and/or properties.
  • polyesters having amide structures It is advantageous in many cases to start from the esters of the carboxylic acids and to prepare the polyesters by transesterification at elevated temperatures, since these transesterifications proceed in some cases more readily and more rapidly than direct esterification.
  • polyfunctional amines it is also possible to obtain polyesters having amide structures.
  • the amounts of components All, A12 and A13 are chosen so that the resulting oligomers are hydroxyl- and/or amino- terminated.
  • the molar fraction of the hydroxy or amino compounds is therefore higher than that of the acid compounds.
  • the excess of equivalents of hydroxyl and/or amino components relative to carboxyl components is from 5 to 200, preferably from 5 to 100 and, with particular preference, from 20 to 50*.
  • hydroxy compounds and a ine compounds are calculated together.
  • the products obtained, even in the case of complete polycondensation, are only of relatively low molecular mass, ie. are oligomers, which are hydroxyl - terminated or, if amine compounds are used as well, are both hydroxyl- and amino-terminated.
  • monofunctional carboxy or hydroxy compounds allows further regulation of the degree of condensation and control of the functionalization of the oligomers.
  • polyfunctional natural substances or derivatives thereof such as linseed oil fatty acid, coconut fatty acid, castor oil, castor oil fatty acid and dimeric and polymeric fatty acids.
  • these oligomeric polyesters are functionalized only at the ends.
  • polyfunctional starting materials such as triols
  • branches are in fact introduced into the polymer backbone and may, in turn, be functionally terminated. Direct functionalization of a polymer main chain, however, is not achieved by this means.
  • the average molecular weight of the oligomers is from 200 to 5000, preferably from 300 to 1000.
  • novel polyesters attain their valuable properties by functionalization in the polymer main chain.
  • the hydroxyl- and/or amino- terminated oligomers of component Al are reacted with polyanhydride compounds of component A2.
  • component A2 use is made of at least one polyanhydride compound having at least two carboxylic anhydride groups.
  • the polyanhydride compound has at least four carboxyl groups, forming two carboxylic anhydride groups.
  • the compound may have further carboxyl groups, present as such or in the form of anhydride groups. It is preferred to employ the anhydrides of aromatic or partly aromatic tetracarboxylic acids. For example, compounds of the formula (I)
  • A is a C 2 . 20 radical which can contain aromatic, aliphatic and/or cycloaliphatic radicals, 0, NR 1 , S and/or S0 2 in the chain or can be substituted by one or more of the organic radicals or halogen atoms,
  • X is 0, NR 2 or S
  • R 1 and R 2 independently are H, C ⁇ -alkyl, C 6 . 12 -aryl, C 7 . 13 -aralkyl or C 3 - alkaryl .
  • the compounds of the formula (I) have units which are derived from trimellitic acid. These units can be linked by way of ester, thioester or amide bonds to the radical A to form a molecule.
  • the radical A is an organic C 2 . 20 radical. It is composed of aromatic, aliphatic and/or cycloaliphatic radicals which can contain 0, NR 1 , S and/or S0 2 as heteroatoms in the chain. They may be substituted, moreover, by one or aromatic, aliphatic and/or cycloaliphatic radicals, and by halogen atoms.
  • A can be a linear unbranched alkyl radical which is attached by way of the terminal carbon atoms to the radicals X.
  • Such a radical preferably has 1 to 12, particularly preferably 1 to 6 carbon atoms.
  • the simplest example of an aromatic radical is a phenylene radical.
  • Examples of combined aliphatic and aromatic radicals are radicals derived from bisphenol A.
  • Preferred radicals are alkyl radicals from C 2 to C 6 .
  • Compounds of the formula (I) can be obtained by reacting trimellitic anhydride with diols, dithiols or diamines.
  • trimellitic anhydride examples of anhydrides of this kind which can be employed in accordance with the invention are described in EP-A-0002718, US 3,435,002 and US 3,749,722.
  • B is -CO-, a single bond, -0-. -S-, S0 2 -, -O-Ph-0-, -C(CH 3 ) 2 -, -CH 2 - or -C0-NH-. Ph here is phenylene.
  • Suitable compounds are benzophenonetetracarboxylic dianhydride, pyromellitic dianhydride, oxydiphthalic dianhydride, diphenyl sulfone tetracarboxylic dianhydride, biphenyltetracarboxylic dianhydride, methylbiscyclohexanetetracarboxylic dianhydride and diphenyl - ethanetetracarboxyl ic dianhydride.
  • tetracarboxylic dianhydrides examples include pyromellitic dianhydride, benzophenonetetracarboxylic dianhydride, biphenyltetracarboxylic dianhydride and oxydiphthalic dianhydride, and also partial esters and/or partial amides of polycarboxylic acids which also contain at least two anhydride functions in the molecule.
  • partial esters or partial amides can be obtained, for example, by reacting tetracarboxylic dianhydrides with a stoichioetric deficit, based on the anhydride groups, of poly-hydroxyl- or -amino-functional substances.
  • component A3 it is possible, if desired, to employ at least one monoanhydride of a polycarboxylic acid.
  • This monoanhydride can be derived from a polycarboxylic acid having more than 2 carboxyl groups.
  • the polycarboxylic acid can be aliphatic, aromatic or mixed aliphatic/- aromatic.
  • suitable monoanhydrides are phthalic anhydride, maleic anhydride, malonic anhydride and, preferably, trimellitic anhydride.
  • Further suitable monoanhydrides are the anhydrides of partial esters of tetracarboxylic acids. Further influence over the end properties of the coatings can be exerted by way of the ester radical of these compounds.
  • component A3 it is preferred to employ phthalic anhydride, maleic anhydride, malonic anhydride or trimellitic anhydride, preferably trimellitic anhydride.
  • Reaction of the polyanhydride compound of component A2 with the oligomer of component Al opens the anhydride groups, and bonding to the oligomers of component Al takes place by way of in each case one of the carboxyl groups of each anhydride function. In this way there are carboxyl groups within the chain of the polyesters. It is therefore possible to obtain polyesters whose chain contains free carboxyl groups which are capable of reaction.
  • the polyesters of component A have a degree of condensation such that they are in liquid form at room temperature (25°C). At 25°C they preferably have a viscosity of not more than 100,000 mPas, preferably not more than 20,000 mPas and, with particular preference, 5000 mPas.
  • the molar ratio of the functional groups in A2 and A3 to functional groups in Al is preferably set such that it is predominantly or exclusively terminal carboxyl groups and/or anhydride groups which are present.
  • the carboxyl groups in the polymer main chain, and possibly present as end groups, are highly suitable functional groups for crossl inking with the crossl inkers of component B that are employed in accordance with the invention.
  • the free carboxyl groups present may be partially or completely neutralized with bases. Neutralization increases the water-solubility of the compounds employed.
  • aqueous binder formulations it is also possible, if desired, to prepare aqueous binder formulations.
  • component A components Al, A2 and, if present, A3 are reacted preferably under conditions in which acid anhydride groups present, but essentially no free carboxyl groups, are reacted.
  • the appropriate components are heated together, for example, at from 60 to 140°C, preferably from 60 to 100°C and, in particular, from 60 to 80°C.
  • the reactions in this case can also be accelerated by means of known esterification catalysts, such as tertiary amines or tin compounds. Such catalysts are often used for oligoester and polyester condensation as well and are therefore present in any case in the reaction mixtures.
  • the amount of component A2 co-reacted determines the number of chain linkages and thus the ultimate molecular weight of the polyesters A. Through the selection of the co-reacted component A2 it is possible to determine the arrangement of the carboxyl groups in the chain.
  • the invention also relates to these polyesters of component A, to the process described for their preparation and their use in the printing-ink or coatings binders, as to coating materials and printing inks as described herein.
  • All compounds suitable for crossl inking with component A can be employed as component B. These are preferably amino resins, highly methylolated and highly etherified mel amines, benzoguanamines, polyfunctional epoxides, polyfunctional blocked or nonblocked isocyanates, or mixtures thereof.
  • the nature of the crossl inker of component B may depend on the nature of the functional groups which are still present in the polyester of component A. This may also influence the properties of the novel low- solvent or solvent-free printing-ink or coatings binders.
  • polyesters of component A having free hydroxyl groups polyisocyanates for two- component applications which cure even at room temperature are suitable.
  • blocked isocyanates are particularly suitable.
  • polyfunctional epoxy resins are suitable crossl inkers for formulating coating materials of limited storage life.
  • the preferred crossl inkers of component B are highly methylolated and highly etherified ureas, mel amines and benzoguanamines.
  • appropriate commercial products are those from the product lines Cymel ® from American Cyanamid, Luwipal ® and Plastopal ® from BASF AG, or hexamethylolmel amine hexamethyl ether (H M), which is marketed by various manufacturers .
  • Crossl inkers of component B such as epoxy resins or isocyanates, which enter into a defined chemical reaction are judiciously employed in chemically equivalent proportions to the functional groups of components A.
  • Crossl inkers with a less specific action such as HMM, are employed in proportions which should be determined empirically relative to the polyester of component A that is to be crossl inked. In general, these proportions are from 2 to 60* by weight of component B based on component A. It is also technically logical to employ mixtures of the abovementioned crossl inkers of component B in order to direct particular properties of the coatings.
  • Crossl inkers for these mixtures are then, for example, blocked polyisocyanates in a mixture with crossl inkers of the HMM type. Owing to the differences in reactivity, stoving forms interpenetrating networks of predominantly urethane-crossl inked hydroxy polyesters and of predominantly HMM-crossl inked carboxy polyesters.
  • Suitable solvents as component C are all solvents which do not interact with but are capable of dissolving components A and B. Furthermore, the carboxyl -modified components A, after (partial) neutralization, are highly compatible with water, so that water is a suitable solvent as well.
  • the printing-ink or coatings binders described above are prepared by reacting components All, A12 and, if present, A13 to give component Al and then reacting Al, A2 and, if present, A3 to give component A, followed by mixing component A and B, followed if appropriate by at least partial neutralization of free carboxyl groups with bases, components All, A12, A13, Al, A2, A3, A and B being as defined above and the reaction of Al, A2 and, if present, A3 being conducted preferably under conditions in which acid anhydride groups present, but essentially no free carboxyl groups, are reacted.
  • Appropriate reaction conditions have been given above.
  • the starting materials for the reaction can be processed without solvent or in a solvent. In each reaction step it is possible for all the starting materials to be introduced together as a mixture and then reacted. Alternatively, they can be metered individually into a reaction mixture. Appropriate methods are known to the skilled worker.
  • the carboxyl groups present can be neutralized preferably with amines. By neutralization it is possible to increase the solubility or dispersibility of the printing-ink or coatings binders in water.
  • the above-described printing-ink or coatings binders can be employed without solvent or in low-solvent mixtures.
  • Low-solvent mixtures are those having a solvent content of from 1 to 40*. preferably from 5 to 10*. by weight, based on the overall printing-ink or coatings binder.
  • the solvent content is preferably very low; in particular, no solvent is used. By this means it is possible very greatly to reduce, or, respectively, to avoid, emissions in the course of processing and curing the printing-ink or coatings binders without impairing the processing properties and the characteristics of the resulting coatings or prints.
  • the coating compositions obtained in accordance with the invention are, consequently, low in or free from solvent, produce an extremely low level of emissions, and can be cured, for example, by stoving or designed so as to be self- curing at room temperature.
  • Novel printing-ink or coatings binders described above can be incorporated into coating materials or printing inks.
  • Novel coating materials or printing inks comprise, as binder, mixtures of
  • component A as described above and b: component B as described above and optionally
  • e from 0 to 70* by weight of water as component E, based on the sum of components A, B, D and, if used, C.
  • customary additives as component D are dyes, fillers and/or color pigments, and also fibrous, matting or gloss-enhancing additives.
  • Further additives are auxiliaries, such as catalysts for crosslinking, surfactants, flow promoters, viscosity regulators, silicone additives, additives for improving the lubricity (mobility) and abrasion, synthetic and natural waxes, and other auxiliaries.
  • Water as the diluent of component E serves to disperse the other components, and these aqueous dispersions can be used as coating compositions.
  • the novel printing- ink and coatings binders are preferably neutralized, at least partially, and are employed alone or in conjunction with a solvent.
  • the invention also relates to the use of the above-described printing-ink or coatings binders, or coating materials and printing inks, for coating, printing and/or impregnating substrates or shaped articles, especially metallic vessels, packaging or parts thereof.
  • the coatings obtained from the novel printing-ink or coatings binders and, respectively, from the novel printing inks or coating materials are pasteurizable and sterilizable. They can also be overprinted or overcoated with excellent intercoat adhesion. In addition, they adhere so firmly that the substrates can be deformed without the coating becoming detached. They are used in particular for coating and/or impregnating two-dimensional or multidimensional, compact, porous, fibrous or particulate substrates, especially of wood, wood materials, metals, glass, including glass fibers, or mineral fibers.
  • a preferred use is in the coating and/or printing of metal packaging, especially of 2-, 3- or multi-part cans for foodstuffs and nonfoods, beverage cans, jar closures, other lids and crown corks made from metallic materials, such as aluminum or tin-plated, zinc-plated or otherwise coated iron or steel .
  • Thermal curing can be carried out with infrared radiation, in stoving ovens or in hot-air tunnels.
  • Oligoester with terminal hydroxyl groups 730.8 g of adipic acid (5 mol ) , 416.7 g of neopentyl glycol (4 ol ) and 472.8 g of hexanediol (4 mol ) were heated to 200°C in 7 hours under a gentle stream of nitrogen in a stirred flask with distil lation device. Cool ing gave a l iquid, sl ightly yel lowish resin having an acid number of 2 mg of KOH/g and an OH number of 197.3 mg of KOH/g. The resin had a viscosity of 910 mPas at 25°C and virtual ly Newtonian flow behavior.
  • binders from Examples 2 and 4 were applied with a doctor blade having a gap height of 25 ⁇ m onto bright aluminum panels and the coated panels were stoved at 160°C for 45 minutes in a convection oven. Cooling gave smooth, glossy films which could be rubbed 50 times with an acetone-soaked cotton pad without showing any traces of attack.

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

Abstract

L'invention concerne des liants de revêtement ou une encre d'impression à faible teneur en solvent ou exempts de solvents. Ces produits comprennent (a) entre 30 et 98 % en poids de polyesters, comme composant A, pouvant être obtenus en faisant réagir (a1) des oligomères à terminaison hydroxyle et/ou aminée, comme composant A1, (a2) au moins un composé polyanhydride présentant au moins deux groupes d'anhydride carboxylique, comme composant A2, avec ou sans (a3) au moins un monoanhydride d'un acide polycarboxylique, comme composant A3, (b) entre 70 et 2 % en poids d'un agent de réticulation pour réticuler les polyesters du composant A, comme composant B, et (c) entre 0 et 30 % en poids, en fonction de la somme des quantités des composants A et B, d'au moins un solvent.
PCT/EP1998/002085 1997-04-15 1998-04-09 Encre d'impression ou liants de revetement durcissables a faible emission WO1998046689A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP98919249A EP0975702A1 (fr) 1997-04-15 1998-04-09 Encre d'impression ou liants de revetement durcissables a faible emission
AU72156/98A AU7215698A (en) 1997-04-15 1998-04-09 Low-emission curable printing-ink or coatings binders
CA002280849A CA2280849A1 (fr) 1997-04-15 1998-04-09 Encre d'impression ou liants de revetement durcissables a faible emission

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19715695.9 1997-04-15
DE19715695A DE19715695A1 (de) 1997-04-15 1997-04-15 Emissionsarme härtbare Lack- oder Druckfarbenbindemittel

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WO1998046689A1 true WO1998046689A1 (fr) 1998-10-22

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AU (1) AU7215698A (fr)
CA (1) CA2280849A1 (fr)
DE (1) DE19715695A1 (fr)
WO (1) WO1998046689A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
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WO2001051574A1 (fr) * 2000-01-11 2001-07-19 Sun Chemical Corporation Encres pouvant etre sechees par energie et procedes de preparation associes
EP1375613A1 (fr) * 2002-06-28 2004-01-02 Carl Kühne KG(GmbH & Co.) Fermeture de récipient pourvue d'une couche antidérapante
WO2007019144A1 (fr) * 2005-08-03 2007-02-15 Ppg Industries Ohio, Inc. Revêtements de boîtes de conserve, procédés destinés au revêtement d’une boîte de conserve et boîtes de conserve ainsi revêtues
US7659341B2 (en) 2003-10-02 2010-02-09 Bayer Materialscience Ag Aqueous compositions for can coating
WO2011047869A1 (fr) * 2009-10-22 2011-04-28 Sig Technology Ag Procédé de production de produit alimentaire autoclavé dans un récipient formé d'un composite de forme plane présentant une couche polymère extérieure réticulée colorée pouvant être obtenue par haute pression
WO2011113453A1 (fr) * 2009-10-22 2011-09-22 Sig Technology Ag Procédé pour préparer des aliments autoclaves dans un récipient formé à partir d'un composite plat et présentant une couche polymère extérieure réticulée colorée pouvant être obtenue par impression en creux
US10273330B2 (en) 2012-06-21 2019-04-30 Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. High-toughness materials based on unsaturated polyesters

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10236349A1 (de) * 2002-08-08 2004-02-19 Basf Coatings Ag Beschichtungsstoffe und ihre Verwendung zur Herstellung schweissbarer Beschichtungen
DE102005046272A1 (de) 2005-09-27 2007-03-29 Wipak Walsrode Gmbh & Co. Kg Individuell markierbare Polymerfolie, Verfahren zu deren Herstellung und zugehörige Produkte
DE102006059115A1 (de) * 2006-12-14 2008-06-19 W.R. Grace & Co.-Conn. Metallsubstratbeschichtungsverfahren

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3247756A1 (de) * 1982-12-23 1984-06-28 Herberts Gmbh, 5600 Wuppertal Waessriges ueberzugsmittel
JPS62240318A (ja) * 1986-04-10 1987-10-21 Nippon Synthetic Chem Ind Co Ltd:The カルボキシル基を有するポリエステル樹脂の製法
JPH04220477A (ja) * 1990-12-21 1992-08-11 Toyo Ink Mfg Co Ltd 無触媒型熱硬化性塗料
US5262510A (en) * 1989-12-28 1993-11-16 Korea Chemical Co., Ltd. Process for preparing polyester resins cured at low temperature and powder coating composition thereof
JPH061839A (ja) * 1992-06-22 1994-01-11 Teijin Ltd ポリエステル水性液
KR940003867B1 (ko) * 1990-12-31 1994-05-04 고려화학 주식회사 저온 경화형 폴리에스테르 수지의 제조방법 및 이를 함유하는 분체도료 조성물
JPH06184485A (ja) * 1992-12-18 1994-07-05 Toyo Ink Mfg Co Ltd 水性印刷インキ
JPH0753717A (ja) * 1993-08-18 1995-02-28 Kanegafuchi Chem Ind Co Ltd 新規な共重合体とその製造方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3247756A1 (de) * 1982-12-23 1984-06-28 Herberts Gmbh, 5600 Wuppertal Waessriges ueberzugsmittel
JPS62240318A (ja) * 1986-04-10 1987-10-21 Nippon Synthetic Chem Ind Co Ltd:The カルボキシル基を有するポリエステル樹脂の製法
US5262510A (en) * 1989-12-28 1993-11-16 Korea Chemical Co., Ltd. Process for preparing polyester resins cured at low temperature and powder coating composition thereof
JPH04220477A (ja) * 1990-12-21 1992-08-11 Toyo Ink Mfg Co Ltd 無触媒型熱硬化性塗料
KR940003867B1 (ko) * 1990-12-31 1994-05-04 고려화학 주식회사 저온 경화형 폴리에스테르 수지의 제조방법 및 이를 함유하는 분체도료 조성물
JPH061839A (ja) * 1992-06-22 1994-01-11 Teijin Ltd ポリエステル水性液
JPH06184485A (ja) * 1992-12-18 1994-07-05 Toyo Ink Mfg Co Ltd 水性印刷インキ
JPH0753717A (ja) * 1993-08-18 1995-02-28 Kanegafuchi Chem Ind Co Ltd 新規な共重合体とその製造方法

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 9607, Derwent World Patents Index; AN 96-067424, XP002071744 *
PATENT ABSTRACTS OF JAPAN vol. 012, no. 117 (C - 487) 13 April 1988 (1988-04-13) *
PATENT ABSTRACTS OF JAPAN vol. 016, no. 566 (C - 1009) 8 December 1992 (1992-12-08) *
PATENT ABSTRACTS OF JAPAN vol. 018, no. 201 (C - 1188) 8 April 1994 (1994-04-08) *
PATENT ABSTRACTS OF JAPAN vol. 018, no. 528 (C - 1258) 6 October 1994 (1994-10-06) *
PATENT ABSTRACTS OF JAPAN vol. 95, no. 5 30 June 1995 (1995-06-30) *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001051574A1 (fr) * 2000-01-11 2001-07-19 Sun Chemical Corporation Encres pouvant etre sechees par energie et procedes de preparation associes
US6605652B1 (en) 2000-01-11 2003-08-12 Sun Chemical Corporation Energy curable inks and methods of preparing same
EP1375613A1 (fr) * 2002-06-28 2004-01-02 Carl Kühne KG(GmbH & Co.) Fermeture de récipient pourvue d'une couche antidérapante
US7659341B2 (en) 2003-10-02 2010-02-09 Bayer Materialscience Ag Aqueous compositions for can coating
WO2007019144A1 (fr) * 2005-08-03 2007-02-15 Ppg Industries Ohio, Inc. Revêtements de boîtes de conserve, procédés destinés au revêtement d’une boîte de conserve et boîtes de conserve ainsi revêtues
US7475786B2 (en) 2005-08-03 2009-01-13 Ppg Industries Ohio, Inc. Can coatings, methods for coating can and cans coated thereby
WO2011047869A1 (fr) * 2009-10-22 2011-04-28 Sig Technology Ag Procédé de production de produit alimentaire autoclavé dans un récipient formé d'un composite de forme plane présentant une couche polymère extérieure réticulée colorée pouvant être obtenue par haute pression
WO2011113453A1 (fr) * 2009-10-22 2011-09-22 Sig Technology Ag Procédé pour préparer des aliments autoclaves dans un récipient formé à partir d'un composite plat et présentant une couche polymère extérieure réticulée colorée pouvant être obtenue par impression en creux
CN102666302A (zh) * 2009-10-22 2012-09-12 Sig科技公司 在具有着色交联外侧聚合物层的面状复合结构构成的容器内通过高压制备高压灭菌食品的方法
CN102666302B (zh) * 2009-10-22 2016-03-02 Sig科技公司 在具有着色交联外侧聚合物层的面状复合结构构成的容器内通过高压制备高压灭菌食品的方法
EA024369B1 (ru) * 2009-10-22 2016-09-30 Сиг Текнолоджи Аг Способ получения автоклавированных пищевых продуктов в контейнере из листового композита с внешним слоем из окрашенного сшитого полимера высокого давления
US10273330B2 (en) 2012-06-21 2019-04-30 Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. High-toughness materials based on unsaturated polyesters

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