EP1765904A1 - Resines aqueuses fonctionnalisees - Google Patents

Resines aqueuses fonctionnalisees

Info

Publication number
EP1765904A1
EP1765904A1 EP05747885A EP05747885A EP1765904A1 EP 1765904 A1 EP1765904 A1 EP 1765904A1 EP 05747885 A EP05747885 A EP 05747885A EP 05747885 A EP05747885 A EP 05747885A EP 1765904 A1 EP1765904 A1 EP 1765904A1
Authority
EP
European Patent Office
Prior art keywords
resin dispersions
dispersions according
isocyanate
reaction
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.)
Withdrawn
Application number
EP05747885A
Other languages
German (de)
English (en)
Inventor
Werner Andrejewski
Patrick GLÖCKNER
Lutz Mindach
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.)
Evonik Operations GmbH
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 EP1765904A1 publication Critical patent/EP1765904A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
    • C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
    • C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes

Definitions

  • the present invention relates to functionalized, aqueous ketone, ketone / aldehyde or urea / aldehyde resin dispersions and to a process for their preparation.
  • 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 dihydroxy compounds (b) having a molecular weight of 500 to 5,000 which do not convert groups which can be converted into ionic groups (for example carboxylic acid groups), but other functional groups such as or ether groups (see page 3, lines 17-21).
  • the polyurethane thus obtained is still with a compound (c) which contains in addition to NCO-reactive groups nor a group which can be converted into 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.
  • this reaction product is reacted with a condensation resin and brought into the water.
  • the present invention underlying resins are not mentioned.
  • DE-OS 2408 865 describes melamine-formaldehyde-polyurethane resins which are water-dilutable or water-dispersible.
  • the base of the polyurethane resin is based on alkyd resin based polycondensation products (see page 2, first paragraph).
  • Alkyd resins are made from carboxylic acids, unsaturated fatty acids, diols and polyols.
  • DE-OS 34 06 473 and DE-OS 34 06 474 and EP-AO 154 835 describe processes for the preparation of stable aqueous dispersions of urea- ⁇ ldehyd resins or ketone / (aldehyde) resins, after which the resin melt or its highly concentrated solution in the presence of organic protective colloids optionally dispersed in water with the addition of emulsifiers.
  • a disadvantage of these processes is the fact that the organic protective colloids and emulsifiers interfere with the application of the aqueous ketone / (aldehyde) or urea / aldehyde resins in the coating sector.
  • the hydrophilic protective colloids and optionally emulsifiers remain in the coating and make them sensitive to moisture. The coating swells when exposed to moisture, loses its hardness and loses its anti-corrosion effect.
  • the object of the invention was to develop functionalized ketone, ketone / aldehyde or urea / aldehyde resin dispersions and a process for their preparation.
  • the resin dispersions should be stable to hydrolysis or storage and should not have the disadvantages described above.
  • the ketone-, ketone-aldehyde-, urea-acid-aldehyde resins of the invention thus modified give stable aqueous solutions, dilutions and dispersions.
  • aqueous systems according to the invention are completely resistant to hydrolysis in comparison with the systems already known from the prior art and contain no interfering additives, for example.
  • the present invention relates to aqueous resin dispersions, and a process for their preparation obtainable by reaction or proportionate reaction of
  • At least one 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
  • Suitable as component A) are all resins which are listed in DE-OS 102004005 208.5 and DE-OS 10 2004 005 204.7. Preference is given to hydroxyl-containing ketone
  • the hydrophilic modification of B) is carried out by reacting a (poly) isocyanate and / or mixtures of different (poly) isocyanates with compounds having (in addition to the hydrophilic or potentially hydrophilic group) at least one isocyanate-reactive function, eg.
  • OH OH, NH, and having at least one hydrophilic group and / or a potentially hydrophilic group, ie, the hydrophilic after neutralization
  • hydrophilic modification of the polyisocyanates are aminocarboxylic acids, hydroxysulfonic acids, aminosulfonic acids and hydroxycarboxylic acids.
  • the hydrophilic modification can also be done with already neutralized compounds.
  • Hydroxycarboxylic acids such as dimethylolpropionic acid, dimethylolbutyric acid, bis (hydroxyphenyl) valeric acid and / or hydroxypivalic acid are particularly preferred because they are neutralized with volatile bases such.
  • B. Coatings do not soften when exposed to moisture or start off white.
  • Dimethylolpropionic acid and 2 - [(2-aminoethyl) amino] -ethanesulfonic acid are also particularly preferred because they are capable of hydrophilically modifying (potentially) two hydrophobic polyisocyanates.
  • Suitable polyisocyanates for the preparation of B) are preferably di- to tetrafunctional polyisocyanates having a below 800 g / mol lying Poppy with aliphatic, (cyclo) aliphatic and / or cycloaliphatic bound isocyanate groups, such as are commonly used in the field of polyurethane coatings, as well as mixtures of these: 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate; IPDI), trimethylhexamethylene diisocyanate (TMDI), 1,6-diisocyanatohexane (HDI), bis (4-isocyanatohexyl) -methane (Hi 2 MDI), and Other polyisocyanates which are listed in DE-OS 24 56469, p.
  • Ebenfells suitable are oligomers obtainable from the monomeric polyisocyanates, whose recovery corresponds to the prior art and, for example, in the Journal of Practical Chemistry 336 (1994), 185-200 and Farb und Lack 100, 5 (1994), 330-335 and the literature cited therein. These are polyisocyanates with biuret, uretdione or isocyanurate structure, the latter obtainable by cyclotrimerization of the monomers. Also suitable are polyisocyanates as products of polyhydric alcohols and / or amines with monomeric isocyanates, such as. B. the product of trimethylolpropane and isophorone diisocyanate.
  • non-ionic hydrophilization may e.g. via polyethers, e.g. can be reacted with the above polyisocyanates and component A).
  • the introduction of the functional components (C) can be carried out by reacting a (poly) isocyanate and / or mixtures of different (poly) isocyanates with compounds having at least one isocyanate-reactive function, for. B. OH, NH and with at least one further functional group in the way that at least one NCO function is maintained and subsequent reaction with A) before or after reaction with B).
  • the preparation of the component C) can also be carried out in-situ during the pre-adduct preparation.
  • component C) it is possible in principle to use aliphatic or aromatic alcohols and / or amines or aromatic heteroaromatic ring systems which have a further functionality in addition to the NCO-reactive group.
  • Preferred examples of such compounds are dimethylaminopropylatnine, diethanolamine, pyrrolidone and / or hydroxypivalic acid.
  • reaction of A) with B) and / or C) can be carried out in bulk or preferably in the presence of a suitable auxiliary solvent.
  • Preferred solids contents are 50 to 95% by mass, particularly preferably 60 to 80% by mass, when using an auxiliary solvent.
  • Suitable Hüfslierestoff are either preferred those which have a boiling point below 100 0 C at 1013 hPa and can be removed by distillation from the final aqueous system again completely to a residual content of 0, mass% and re-use, such as acetone, methyl ethyl ketone or tetrahydrofuran , or possibly higher boiling, which remain in the aqueous system, such as butyl glycol, butyl diglycol or N-methylpyrrolidone.
  • the below 100 ° C boiling auxiliary solvents are therefore preferred because they allow the production of purely aqueous, solvent-free and therefore environmentally friendly dispersions.
  • An advantage of the method according to the invention 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.
  • component C e.g. an adduct of 1 mol of diisocyanate and 1 mol of a functional NCO-reactive component optionally prepared using a suitable solvent and a suitable catalyst.
  • component B e.g. an adduct of 2 moles of diisocyanate and 1 mole of dimethylolpropionic acid and / or 2 - [(2-aminoethyl) amino] ethanesulfonic acid or derivatives thereof are optionally prepared using a suitable solvent and a suitable catalyst.
  • the separately prepared products are added to a solution or melt of the hydroxyl-containing ketone, ketone-aldehyde, urea-aldehyde or their hydrogenated secondary products (A) and reacted.
  • the temperature of the reaction is selected. There have in all reaction steps, temperatures from 30 to 245 0 C, preferably between 50 and 140 ° C proved.
  • the solvent optionally present can be separated off after the reaction has ended, in which case a solution is usually obtained until the dispersion of the product according to the invention is obtained.
  • component B) z can be used as component B) z.
  • an adduct of 2 moles of diisocyanate and 1 mole of dimethylolpropionic acid and / or 2 - [(2-aminoethyl) amino] ethanesulfonic acid or derivatives thereof are optionally prepared using a suitable solvent and a suitable catalyst.
  • the product is added to a solution or melt of the hydroxyl-containing ketone, ketone-aldehyde, urea-aldehyde or their hydrogenated secondary products (A) and the component C) and further polyisocyanate and reacted.
  • the solvent optionally present can be separated off after the reaction has ended, in which case a solution is usually obtained until the dispersion of the product according to the invention is obtained.
  • a suitable catalyst for the preparation of the resins of the invention can be used.
  • Suitable are all known in the literature compounds that accelerate an NH or OH-NCO reaction, such as. B. diazabicyclooctane (DABCO) or dibutyltin dilaurate (DBTL), titanic acid esters, bismuth salts.
  • DABCO diazabicyclooctane
  • DBTL dibutyltin dilaurate
  • titanic acid esters bismuth salts.
  • hydrophilicizing agent forms a potentially hydrophilic group, e.g. As a carboxyl group or a tertiary amino group introduced into the polyisocyanate, it can be converted by subsequent neutralization in an ionic hydrophilic group.
  • Embodiments 1) and 2) can be carried out with inorganic and organic bases, such as.
  • ammonia or organic amines Preference is given to using primary, secondary and tertiary amines, such as. Ethylamine, propylamine, dimethylamine, dibutylamine,
  • Cyclohexylamine, benzylamine, morpholine, piperidine and triethanolamine Particular preference is given to volatile tertiary amines, in particular dimethylethanolamine, diethylethanolamine, 2-
  • the amount of neutralization depends on the content of potentially neutralisable groups in the hydrophilically modified polyisocyanate and is preferably 50 to 130% of the
  • Amount of neutralization necessary for stoichiometric neutralization is neutralized in the same way with suitable acids, such as acetic acid, formic acid, benzoic acid or lactic acid.
  • reaction product of A, B and C may optionally be combined with other non-hydrophilic resins or other water-soluble or water-dilutable components and then dispersed together.
  • This measure makes it technically advantageous to achieve a high solids content of the dispersions of more than 35% by mass, preferably from 35 to 40% by mass, to about 50% by mass.
  • the resin dispersions of the invention have good storage stabilities and are suitable as resins or additional resins in BescMchtungsstoffen, ballpoint pen inks and inks, polishes, glazes, fillers, cosmetics and / or sealing and insulating materials. Also for use in adhesives, such. As for the bonding of textiles, leather, paper and similar materials, such resin dispersions are suitable.
  • the resin dispersions of the invention are at least 6 weeks at 50 0 C sedimentation stable.
  • DMPS dimethylolpropionic acid
  • the two precursors are combined in a nitrogen atmosphere, with 544 g of a hydroxyl-containing ketone / aldehyde resin (OHZ 310 mg KOH / g, resin SK, Degussa AG), which is dissolved in 508 g of acetone, and with 1.24 g of a 10% DBTL solution in acetone. It is stirred at reflux temperature until an NCO content of less than 0.15% is reached.
  • a hydroxyl-containing ketone / aldehyde resin (OHZ 310 mg KOH / g, resin SK, Degussa AG)
  • Resin dispersion having a solids content of about 24.8% by mass, a pH of 8.0 and a viscosity of about 90 mPas.
  • 253 g of isophorone diisocyanate are added with stirring to a mixture of 51 g of dimethylolpropionic acid (DMPS), 253 g of acetone and 0.3 g of a 10% by mass solution of dibutyltin dilaurate (DBTL) in acetone so quickly that the exothermic reaction is readily controllable remains.
  • DMPS dimethylolpropionic acid
  • DBTL dibutyltin dilaurate
  • the precursor After cooling to room temperature in nitrogen atmosphere, the precursor with 480 g of a hydroxyl-containing ketone / Aldehydhatzes (OHZ 310 mg KOH / g, resin SK, Degussa AG), which is dissolved in 400 g of acetone, and with 0.5 g of a 10% DBTL solution in acetone
  • the mixture is stirred at reflux temperature until an NCO content of less than 1.3% is reached.
  • 38.3 g of diethanolamine dissolved in 31.2 g of acetone are added, and it is stirred to an NCO content below 0.15%.
  • 250 g of the solution prepared under 1) are neutralized at room temperature with stirring by adding 6.3 g of triethylamine and dispersed by introducing 335 g of deionized water with vigorous stirring.
  • the auxiliary solvent acetone and proportional water are removed in vacuo, and there is a storage-stable, finely divided, slightly opalescent resin dispersion having a solids content of about 29.5% by mass, a pH of 8.6 and a viscosity of about 520 mPas received.

Landscapes

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

Abstract

L'invention concerne des dispersions aqueuses de résines fonctionnalisées obtenues par réaction ou réaction partielle de A) résines urée/aldéhyde, cétone/aldéhyde, cétone contenant des groupes hydroxyle ou leurs produits de réaction hydrogénés et B) au moins un isocyanate et/ou polyisocyanate modifié comportant au moins un groupe NCO libre, pouvant être obtenu par réaction d'au moins un isocyanate et/ou d'un polyisocyanate avec des composés qui possèdent, outre un groupe hydrophile ou potentiellement hydrophile, au moins une fonction réactive vis-à-vis des groupes isocyanate, ainsi qu'au moins un groupe hydrophile et/ou un groupe potentiellement hydrophile, C) au moins un composé présentant une fonction réactive vis-à-vis des groupes isocyanate et d'autres groupes fonctionnels, puis par mélange de la résine éventuellement neutralisée avec de l'eau. L'invention concerne également un procédé pour la production desdites dispersions de résines.
EP05747885A 2004-07-15 2005-05-23 Resines aqueuses fonctionnalisees Withdrawn EP1765904A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200410034303 DE102004034303A1 (de) 2004-07-15 2004-07-15 Funktionalisierte, wässrige Harze
PCT/EP2005/052350 WO2006005644A1 (fr) 2004-07-15 2005-05-23 Resines aqueuses fonctionnalisees

Publications (1)

Publication Number Publication Date
EP1765904A1 true EP1765904A1 (fr) 2007-03-28

Family

ID=35170186

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05747885A Withdrawn EP1765904A1 (fr) 2004-07-15 2005-05-23 Resines aqueuses fonctionnalisees

Country Status (9)

Country Link
EP (1) EP1765904A1 (fr)
CN (1) CN1918206A (fr)
BR (1) BRPI0513339A (fr)
CA (1) CA2573724A1 (fr)
DE (1) DE102004034303A1 (fr)
MX (1) MX2007000437A (fr)
RU (1) RU2007105542A (fr)
TN (1) TNSN07008A1 (fr)
WO (1) WO2006005644A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005006296A1 (de) * 2005-02-11 2006-08-24 Degussa Ag Wässrige Zusammensetzungen
DE102005010947A1 (de) * 2005-03-10 2006-09-14 Degussa Ag Wässrige Beschichtungsstoffzusammensetzungen mit verbessertem Steinschlagschutz
EP2316868A1 (fr) * 2009-10-27 2011-05-04 Cytec Surface Specialties Austria GmbH Polyuréthanne dispersible dans l'eau
CN109111559A (zh) * 2018-07-25 2019-01-01 禾丰新材料科技有限公司 水性聚酮树脂乳液及其制备方法和应用
CN114149556B (zh) * 2021-11-18 2023-10-27 广东西顿新材料科技有限公司 一种醛酮改性自消光水性聚氨酯分散体及其制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4309079A1 (de) * 1993-03-20 1994-09-22 Basf Ag Wäßrige Dispersion eines Polyurethan und eines Kondensationsharzes
DE19643704A1 (de) * 1996-10-23 1998-04-30 Huels Chemische Werke Ag Wäßrige Harzdispersionen
ES2216764T3 (es) * 1999-06-21 2004-11-01 Surface Specialties Austria Gmbh Resinas diluibles con agua, procedimiento para su preparacion y su utilizacion.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006005644A1 *

Also Published As

Publication number Publication date
CA2573724A1 (fr) 2006-01-19
TNSN07008A1 (en) 2008-06-02
MX2007000437A (es) 2007-03-07
BRPI0513339A (pt) 2008-05-06
CN1918206A (zh) 2007-02-21
DE102004034303A1 (de) 2006-02-09
WO2006005644A1 (fr) 2006-01-19
RU2007105542A (ru) 2008-08-20

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