WO2006094850A1 - Compositions de substance de revetement aqueuses presentant une meilleure resistance aux projections de gravier - Google Patents

Compositions de substance de revetement aqueuses presentant une meilleure resistance aux projections de gravier Download PDF

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Publication number
WO2006094850A1
WO2006094850A1 PCT/EP2006/050231 EP2006050231W WO2006094850A1 WO 2006094850 A1 WO2006094850 A1 WO 2006094850A1 EP 2006050231 W EP2006050231 W EP 2006050231W WO 2006094850 A1 WO2006094850 A1 WO 2006094850A1
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WO
WIPO (PCT)
Prior art keywords
component
aqueous coating
compositions according
coating compositions
aqueous
Prior art date
Application number
PCT/EP2006/050231
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German (de)
English (en)
Other versions
WO2006094850A8 (fr
Inventor
Patrick GLÖCKNER
Andreas Wenning
Werner Andrejewski
Original Assignee
Degussa Gmbh
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 Degussa Gmbh filed Critical Degussa Gmbh
Publication of WO2006094850A1 publication Critical patent/WO2006094850A1/fr
Publication of WO2006094850A8 publication Critical patent/WO2006094850A8/fr

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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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/54—Polycondensates of aldehydes
    • C08G18/548—Polycondensates of aldehydes with ketones
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8048—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/34
    • 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
    • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
    • C09D161/02—Condensation polymers of aldehydes or ketones only

Definitions

  • Aqueous coating compositions with improved stone chip protection are provided.
  • the invention relates to aqueous coating compositions with improved stone chip protection effect consisting of at least one binder, a modified ketone / aldehyde resin and optionally auxiliaries and additives for the coating of metals and plastics.
  • the coating compositions are used in particular for the
  • the coating compositions are characterized by a particularly high rate of drying and by a particularly high hardness with very good elasticity and adhesion properties. Particularly noteworthy is the excellent protective effect against mechanical damage due to intensive and short-term stress as it is mainly due to z. B. Rockfall can be caused.
  • Very good adhesion properties are indispensable for the permanent protection of the substrate. Especially with metal substrates, a very good adhesion is required, so that a high corrosion protection effect is achieved. For use in multicoat paint systems, excellent intercoat adhesion is of great importance. In addition, many durable goods are subject to constant mechanical stress, so that high demands are placed on a coating with regard to abrasion resistance and resistance to external influences.
  • Hard resins based on ketones and aldehydes are known to increase the hardness of coating materials.
  • water-soluble condensation products are listed, which are also obtained by joint reaction of ketones, aldehydes and acid groups introducing compounds. Examples of the latter are sulfites, amidosulfonic acid, aminoacetic acid and phosphorous acid salts.
  • EP 0 617 103 A1 describes the reaction of polyisocyanates (a) and
  • the polyurethane thus obtained is still with a compound (c) which contains in addition to NCO-reactive groups nor a überbowbare group in an ionic group, and optionally with diols or polyols (d) having a molecular weight of 60 to 500, which no further functional Wear groups (see page 4, lines 5 to 15), implemented. Then this will be
  • Reaction product reacted with a condensation resin and transferred to the aqueous phase.
  • EP 0838485 describes esterified products. It is known that ester groups hydrolyze, whereby polymer degradation takes place and the storage stability is adversely affected. In addition, a reaction or incompatibility with pigments can be caused by freely accessible acid groups.
  • EP 0838486 describes aqueous resin dispersions obtainable by reaction or proportionate reaction of
  • At least one hydrophilic modified isocyanate and / or polyisocyanate having at least one free NCO group obtainable by reacting at least one isocyanate and / or polyisocyanate with compounds which in addition to the hydrophilic or potentially hydrophilic group at least one isocyanate-reactive Have function and have one according to the Zerewitinoff test active hydrogen, as well as at least one hydrophilic group and / or a potentially hydrophilic group, and then mixing the neutralized resin with water.
  • the object of the present invention was to find aqueous coating compositions which give coatings which are characterized by very good adhesion properties and stone impact resistance.
  • the coatings should be largely free of formaldehyde. Also, the coating materials should have a high drying speed.
  • the invention relates to aqueous coating compositions, in particular for improving the stone impact resistance on different substrate substrates, substantially containing
  • composition A) The aqueous binders A) essential to the invention are used in amounts of from 20 to 98% by weight, preferably from 30 to 80% by weight.
  • aqueous binders from the group of polyurethanes, polyacrylates, polyethers, polyesters, alkyd resins, cellulose ethers, derivatives of cellulose, polyvinyl alcohols and
  • Alkali silicates eg waterglass
  • silicone resins used.
  • the aqueous binders may be foreign and / or self-crosslinking, air-drying (physically drying) and / or oxidatively curing.
  • the component B) essential to the invention is used in amounts of from 2 to 80% by weight, preferably from 4 to 60% by weight.
  • Suitable as component B) are aqueous resin dispersions obtainable by reaction or proportionate reaction of I. hydroxyl-containing ketone / aldehyde resins or their hydrogenated derivatives and II. At least one hydrophilic modified isocyanate and / or polyisocyanate with at least one free NCO group, obtainable by reacting at least one Isocyanate and / or polyisocyanate with compounds which in addition to the hydrophilic or potentially hydrophilic group have at least one isocyanate-reactive function, and subsequent mixing of the optionally neutralized resin with water.
  • Suitable ketones for the preparation of the ketone / aldehyde resins are all ketones, in particular acetone, acetophenone, methyl ethyl ketone, heptanone-2, pentanone-3, methyl isobutyl ketone, cyclopentanone, cyclododecanone, mixtures of 2,2,4- and 2, 4,4-trimethylcyclopentanone, cycloheptanone and cyclooctanone, cyclohexanone and all alkyl-substituted cyclohexanones having one or more alkyl radicals which contain a total of 1 to Have 8 hydrocarbon atoms, individually or in mixture.
  • alkyl-substituted cyclohexanones there can be mentioned 4-tert-amylcyclohexanone, 2-sec-butylcyclohexanone, 2-tert-butylcyclohexanone, 4-tert-butylcyclohexanone, 2-methylcyclohexanone and 3,3,5-trimethylcyclohexanone ,
  • ketones which have other functional groups, such as. B. amino and / or acid groups.
  • ketones usually all C-H-acidic ketones, can be used.
  • suitable ketones usually all C-H-acidic ketones.
  • Preferred are ketone / aldehyde resins based on acetophenone, cyclohexanone, 4-tert-butylcyclohexanone, 3,3,5-trimethylcyclohexanone and heptanone alone or in a mixture.
  • aldehyde component of the ketone / aldehyde resins are in principle unsubstituted or branched aldehydes, such as.
  • formaldehyde acetaldehyde, n-butyraldehyde and / or iso-butyraldehyde, valeric aldehyde and dodecanal.
  • all the aldehydes mentioned in the literature as suitable for ketone / aldehyde resin syntheses can be used.
  • formaldehyde is used alone or in mixtures.
  • the required formaldehyde is usually used as about 20 to 40 wt .-% aqueous or alcoholic (eg, methanol or butanol) solution.
  • alcoholic eg, methanol or butanol
  • Other uses of formaldehyde such.
  • para-formaldehyde or trioxane are also possible.
  • Aromatic aldehydes, such as. B. benzaldehyde may also be included in admixture with formaldehyde.
  • ketone / aldehyde resins of component I particular preference is given to using acetophenone, cyclohexanone, 4-tert-butylcyclohexanone, 3,3,5-trimethylcyclohexanone and also heptanone alone or in a mixture and formaldehyde.
  • the resins of ketone and aldehyde can also be hydrogenated in the presence of a suitable catalyst with hydrogen at pressures of up to 300 bar. This is part of the Carbonyl groups of the ketone / aldehyde resin converted into secondary hydroxyl groups.
  • a suitable catalyst with hydrogen at pressures of up to 300 bar.
  • the possibly necessary hydrophilic modification takes place for.
  • a component IL consisting of at least one hydrophilic modified isocyanate and / or polyisocyanate having at least one free NCO group, obtainable by reacting at least one isocyanate and / or polyisocyanate with compounds in addition to the hydrophilic or potentially hydrophilic group - ie those groups which become hydrophilic only after neutralization - have at least one isocyanate-reactive function such as.
  • Examples of such compounds for the hydrophilic modification of (poly) isocyanates are amino acids, hydroxysulfonic acids, aminosulfonic acids and hydroxycarboxylic acids. Preference is given to using dimethylolpropionic acid or derivatives thereof.
  • the hydrophilic modification can also be carried out with non-ionic groups (eg with polyethers) or already neutralized compounds.
  • Hydroxycarboxylic acids in particular dimethylolpropionic acid, are therefore particularly preferred because they are neutralized with volatile bases, such as.
  • volatile bases such as.
  • amines show strong hydrophilic effect, after evaporation of the volatile base, however, this effect decreases greatly. Coatings therefore do not lose by z.
  • the dimethylolpropionic acid is also particularly preferred since it is capable of hydrophilically modifying (potentially) two hydrophobic polyisocyanates via its two hydroxyl groups.
  • Suitable polyisocyanates for the preparation of II. are preferably di- to tetrafunctional Polyisocyanates. Examples of these are cyclohexane diisocyanate, methylcyclohexane diisocyanate, ethylcyclohexane diisocyanate, propylcyclohexane diisocyanate, methyldiethylcyclohexane diisocyanate, phenylene diisocyanate, toluene diisocyanate, bis (isocyanatophenyl) methane, propane diisocyanate, butane diisocyanate, pentane diisocyanate, hexane diisocyanate, such as hexamethylene diisocyanate (HDI) or 1,5-diisocyanato-2-methylpentane (MPDI).
  • HDI hexamethylene diisocyanate
  • MPDI 1,5-diisocyanato-2-methylp
  • IPDI isophorone diisocyanate
  • NBDI 1,3-bis (isocyanatomethyl) cyclohexane (1,3-H 6 -XDI) or 1,4-bis (isocyanato-methyl) cyclohexane (1,4-H 6 -XDI) alone or in a mixture.
  • polyisocyanates are the compounds prepared by di- or trimerization, allophanatization, biuretization and / or urethanization of simple diisocyanates with more than two isocyanate groups per molecule, for example the
  • H 12 MDI with polyhydric alcohols (for example glycerol, trimethylolpropane, pentaerythritol) or polyhydric polyamines or the triisocyanurates obtainable by trimerization of the simple diisocyanates, such as, for example, IPDI, HDI and H 12 MDI.
  • polyhydric alcohols for example glycerol, trimethylolpropane, pentaerythritol
  • polyhydric polyamines or the triisocyanurates obtainable by trimerization of the simple diisocyanates, such as, for example, IPDI, HDI and H 12 MDI.
  • hydrophilically modified polyisocyanate of dimethylolpropionic acid or derivatives thereof and IPDI and / or TMDI and / or H 12 MDI and / or HDI in a molar ratio of 1: 2.
  • component B) is carried out in the melt or in solution of a suitable organic solvent, which - if desired - can be separated by distillation after preparation.
  • Preferred solids contents in the case of a reaction in solution are 30 to 95 wt .-%, particularly preferably 60 to 80 wt .-%.
  • Suitable auxiliary solvents are low-boiling inert solvents which do not form a miscibility gap with water over wide ranges, have a boiling point at atmospheric pressure below 100 ° C. and are therefore easily distilled to a residual content of less than 2% by weight and, if desired, by distillation less than 0.5% by weight, based on the finished dispersion or aqueous solution, and that it can be reused.
  • Suitable solvents of this type are for. As acetone, methyl ethyl ketone or tetrahydro-uranium. In principle, higher-boiling solvents such. As n-butyl glycol, di-n-butyl glycol and N-methylpyrrolidone, which then remain in the dispersion.
  • component B lies precisely in the fact that it is possible completely to dispense with organic solvents in the finished aqueous resin dispersion and still obtain solids-rich, stable dispersions.
  • the reaction of I and II is preferably allowed to proceed so far that a residual NCO content of 1% NCO (determined according to DIN 53185) is exceeded, and particularly preferably progress so far that the residual NCO content of the product I and II im
  • NCO functions can be, according to the prior art, either too
  • Chain extension reactions e.g. B. by adding polyamines or water, or possibly a chain termination by addition to NCO groups monofunctional
  • Initiate compounds eg monoalcohols, monoamines.
  • the products according to the invention can be mixed with a suitable neutralizing agent, which then gives water-dilutable, water-dispersible or water-soluble products.
  • the neutralization of the potentially hydrophilic groups of the resins according to the invention can be carried out with inorganic and / or organic bases, such as.
  • inorganic and / or organic bases such as.
  • ammonia or organic amines Preferably used are primary, secondary and / or tertiary amines, such as. For example, ethylamine, propylamine, dimethylamine, dibutylamine, cyclohexylamine, benzylamine, morpholine, piperidine and triethanolamine.
  • volatile, tertiary Amines in particular dimethylethanolamine, diethylethanolamine, 2-dimethylamino-2-methyl-l-propanol, triethylamine, tripropylamine and tributylamine in the case of anionic potential groups.
  • cationic potential ionic groups can be neutralized with inorganic and / or organic acids, such as. As acetic acid, formic acid, phosphoric acid, hydrochloric acid, etc.
  • the degree of neutralization is preferably 50 to 130% of the neutralization amount necessary for stoichiometric neutralization.
  • the neutralized hydrophilic resin or the resin solution is either passed into water or it is preferably mixed with water while stirring.
  • the reaction product of I and II may optionally be combined with other non-hydrophilic resins or other components and then dispersed together.
  • a technically advantageous high solids content of the dispersions of over 45 wt .-% can be achieved.
  • the solids content ranges between 20 and 70 wt .-%, preferably between 25 and 60 wt .-%.
  • the organic auxiliary solvent can preferably be removed in vacuo and, if appropriate, worked up again.
  • Component C) is used in amounts of from 0 to 75% by weight, preferably from 5 to 60% by weight.
  • auxiliaries and additives such as inhibitors, organic solvents, surface-active substances, oxygen and / or radical scavengers, catalysts, light stabilizers, color brighteners, photosensitizers and initiators, additives for influencing theological properties such.
  • thixotropic and / or thickening agents leveling agents, anti-skinning agents, defoamers, antistatic agents, plasticizers, lubricants, wetting and dispersing agents, preservatives such.
  • thermoplastic additives dyes, pigments, Matting agents, fire retardants, internal release agents, fillers, isocyanate hardeners and / or blowing agents.
  • the coating compositions are prepared by intensive mixing of the components at temperatures of from 20 to 80 ° C. ("Lehrbuch der Lacktechnologie", Th. Brock, M. Groteklaes, P. Mischke, ed V. Zorll, Vincentz Verlag, Hannover, 1998, page 229 ff.) If necessary, non-liquid components are first dissolved in suitable solvents or water before mixing, then the remaining components are added with stirring. As pigments and / or fillers is carried out a dispersion.
  • the formaldehyde content of the coating compositions is below 100 ppm, preferably below 50 ppm and more preferably below 10 ppm.
  • the claimed aqueous coating compositions have a solids content of from 15% to 80%, preferably from 20% to 60%.
  • the claimed, aqueous coating compositions are particularly suitable for the coating of objects made of metals and plastics. They have a high rate of drying and thus very high blocking resistance.
  • the dried, cured or crosslinked films have a high hardness with good elasticity and adhesion properties, which is expressed in good to very good values in the scratch adhesion, cross-cut test, pendulum or Buchholzhärte and the Erichsentiefung.
  • the claimed, aqueous coating compositions have a perfect course on the substrates used and are free from Surface disorders, such as craters and wetting disorders.
  • the coating compositions of the invention are used as fillers, paints such.
  • Isophorone diisocyanate added so that the exothermic reaction remains well manageable. It is heated to 60 ° C and held this temperature up to an NCO number of 9.2%.
  • the solution prepared under 1) is added with stirring 3300 g of a 55 wt .-% strength acetone solution of a hydrogenated acetophenone / formaldehyde resin (synthetic resin SK Degussa AG), neutralized at room temperature with stirring with 89 g of dimethylaminoethanol and dispersed by adding the solution of 4400 g of demineralized water with stirring.
  • the auxiliary solvent acetone and water as a proportion are removed in vacuo and obtain a storage-stable whitish dispersion having a solids content of about 50 wt .-%.
  • the dispersions A and B according to point 2) were examined for storage stability with regard to changes in the pH, the viscosity and the visual appearance.
  • the formaldehyde content of both coating materials is less than 1 ppm.
  • Test panels Coating structure (spray application) on phosphated steel sheet: cathodic dip coating, primer according to Example, metallic basecoat, clearcoat Drying conditions: Flash off time approx. 10 min, then 20 min 160 ° C

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne des compositions de substance de revêtement aqueuses présentant une meilleure résistance aux projections de gravier, comprenant au moins un liant, une résine cétone/aldéhyde modifiée, et éventuellement des adjuvants et des additifs, et servant à revêtir des métaux et des plastiques.
PCT/EP2006/050231 2005-03-10 2006-01-16 Compositions de substance de revetement aqueuses presentant une meilleure resistance aux projections de gravier WO2006094850A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200510010947 DE102005010947A1 (de) 2005-03-10 2005-03-10 Wässrige Beschichtungsstoffzusammensetzungen mit verbessertem Steinschlagschutz
DE102005010947.0 2005-03-10

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WO2006094850A1 true WO2006094850A1 (fr) 2006-09-14
WO2006094850A8 WO2006094850A8 (fr) 2006-11-09

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DE (1) DE102005010947A1 (fr)
WO (1) WO2006094850A1 (fr)

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CN103073975B (zh) * 2012-10-15 2016-03-02 怀远县巨龙机械制造有限公司 一种醇酸树脂汽车底漆及其制备方法
US8946351B2 (en) 2012-11-19 2015-02-03 King Saud University Environmental friendly poly(ether-fattyamide) resin composition
CN103351772B (zh) * 2013-05-30 2016-06-15 蚌埠市时代电子有限公司 一种耐酸碱散热涂料及其制备方法
CN103333540A (zh) * 2013-05-30 2013-10-02 蚌埠市时代电子有限公司 一种抗老化的散热涂料及其制备方法
CN103351773B (zh) * 2013-05-30 2016-06-29 蚌埠市时代电子有限公司 一种抗紫外线的散热涂料及其制备方法
CN103333594A (zh) * 2013-05-30 2013-10-02 蚌埠市时代电子有限公司 一种自清洁散热涂料及其制备方法
CN103468113A (zh) * 2013-08-16 2013-12-25 安徽快来防水防腐有限公司 一种耐侯性聚氨酯防水涂料

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3075935A (en) * 1959-12-17 1963-01-29 Shawinigan Resins Corp Coating compositions of aqueous vinyl acetate polymer emulsions modified with ketone-aldehyde resins
US4288477A (en) * 1977-10-24 1981-09-08 Moplefan S.P.A. Readily thermoweldable films of polyolefins coated with lacquers based on ketonic resins
EP0617103A1 (fr) * 1993-03-20 1994-09-28 BASF Aktiengesellschaft Dispersion aqueuse d'un polyuréthane et d'une résine de condensation
EP0838486A1 (fr) * 1996-10-23 1998-04-29 Hüls Aktiengesellschaft Dispersions aqueuses de résine
EP0908486A2 (fr) * 1997-10-06 1999-04-14 Vianova Resins Aktiengesellschaft Résines diluables dans l'eau, procédé pour leur préparation et leur utilisation
US5977227A (en) * 1997-09-30 1999-11-02 Ncr Corporation Method for forming aqueous dispersions of ketone resins
EP1063250A2 (fr) * 1999-06-21 2000-12-27 Vianova Resins AG Résines diluables dans l'eau, procédé pour leur préparation et leur utilisation
WO2006005644A1 (fr) * 2004-07-15 2006-01-19 Degussa Ag Resines aqueuses fonctionnalisees

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3075935A (en) * 1959-12-17 1963-01-29 Shawinigan Resins Corp Coating compositions of aqueous vinyl acetate polymer emulsions modified with ketone-aldehyde resins
US4288477A (en) * 1977-10-24 1981-09-08 Moplefan S.P.A. Readily thermoweldable films of polyolefins coated with lacquers based on ketonic resins
EP0617103A1 (fr) * 1993-03-20 1994-09-28 BASF Aktiengesellschaft Dispersion aqueuse d'un polyuréthane et d'une résine de condensation
EP0838486A1 (fr) * 1996-10-23 1998-04-29 Hüls Aktiengesellschaft Dispersions aqueuses de résine
US5977227A (en) * 1997-09-30 1999-11-02 Ncr Corporation Method for forming aqueous dispersions of ketone resins
EP0908486A2 (fr) * 1997-10-06 1999-04-14 Vianova Resins Aktiengesellschaft Résines diluables dans l'eau, procédé pour leur préparation et leur utilisation
EP1063250A2 (fr) * 1999-06-21 2000-12-27 Vianova Resins AG Résines diluables dans l'eau, procédé pour leur préparation et leur utilisation
WO2006005644A1 (fr) * 2004-07-15 2006-01-19 Degussa Ag Resines aqueuses fonctionnalisees

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DE102005010947A1 (de) 2006-09-14
CN1942544A (zh) 2007-04-04
WO2006094850A8 (fr) 2006-11-09

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