EP1786846A1 - Produits de reactions a analogie polymere - Google Patents

Produits de reactions a analogie polymere

Info

Publication number
EP1786846A1
EP1786846A1 EP05769643A EP05769643A EP1786846A1 EP 1786846 A1 EP1786846 A1 EP 1786846A1 EP 05769643 A EP05769643 A EP 05769643A EP 05769643 A EP05769643 A EP 05769643A EP 1786846 A1 EP1786846 A1 EP 1786846A1
Authority
EP
European Patent Office
Prior art keywords
products
polymer
ketone
component
analogous reactions
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Withdrawn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
EP05769643A
Other languages
German (de)
English (en)
Inventor
Patrick GLÖCKNER
Friedrich Georg Schmidt
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 EP1786846A1 publication Critical patent/EP1786846A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • 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
    • C08G6/00—Condensation polymers of aldehydes or ketones only
    • C08G6/02—Condensation polymers of aldehydes or ketones only 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/38—Block or graft polymers prepared by polycondensation of aldehydes or ketones onto macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/02—Condensation polymers of aldehydes or ketones only
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00

Definitions

  • the invention relates to products of polymer-analogous reactions, a process for their preparation and their use.
  • Radiation-sensitive compounds which may optionally contain acetophenone as a sub-grouping or polymeric secondary products with acetophenone groups are described in EP 0 346 788, EP 0 377 199 and DE 102 06 987.
  • EP 0 346 788 describes ethylenically unsaturated, copolymerizable, radiation-sensitive organic compounds which carry at least one (meth) acrylic ester group.
  • EP 0 377 199 describes UV-crosslinkable compositions based on (meth) acrylic ester copolymers.
  • DE 102 06 987 describes vinyl ether derivatives.
  • Ketone aldehyde resins are used in coating materials, for. B. used as additive resins to improve certain properties such as gloss, hardness or scratch resistance.
  • ketone-aldehyde resins have hydroxy groups and can therefore only with z.
  • polyisocyanates or amine resins are crosslinked. These crosslinking reactions are usually initiated or accelerated thermally.
  • Other functional groups e.g. Amino and / or carboxy groups can be introduced only by specific monomers that are either difficult or impossible to obtain on an industrial scale.
  • the object of the present invention was the preparation of products of ketone-aldehyde resins and unsaturated monomers which, in addition to carbonyl and hydroxyl groups, possess further functional groups and are distinguished by altered solubility properties relative to the starting resins.
  • the products should be suitable for use in paints, adhesives, inks and inks, gel coats, polishes, glazes, pigment pastes, fillers, cosmetics and / or sealants and sealants.
  • Suitable ketone-aldehyde resins are polymeric reaction products of aldehydes of the general formula I and ketones of the general formula II, if appropriate using further ketones.
  • R H, unbranched or branched alkyl radical having 1 to 12 carbon atoms, aryl radical,
  • R 1 unbranched alkyl radical having 1 to 12 carbon atoms
  • R 3 to R 7 H, alkyl, OCH 3 , OC 2 H 5 , Cl, F, COO (C 1 -C 3 -alkyl).
  • R 4 to R 6 may be OH, SH.
  • Suitable unsaturated monomers are all unsaturated monomers which can be free-radically polymerized.
  • the invention therefore relates to polymeric reaction products, essentially comprising the reaction product
  • R H, unbranched or branched alkyl radical having 1 to 12 carbon atoms, aryl radical
  • R 1 unbranched alkyl radical having 1 to 12 carbon atoms
  • radicals R 3 to R 7 are H, alkyl, OCH 3 , OC 2 H 5 , Cl, F, COO (C 1 -C 3 -alkyl), R 4 to R 6 additionally OH, SH
  • aldehyde component A) for use as the main component, base component or additive component in coating materials, adhesives, printing inks and inks, gelcoats, polishes, glazes, pigment pastes, fillers, cosmetic articles and / or sealants and insulating materials.
  • aldehyde component A) according to formula I are in principle unsubstituted or branched aldehydes, such as. As formaldehyde, benzaldehyde, acetaldehyde, n-butyraldehyde and / or isobutyraldehyde, valeric aldehyde and dodecanal. In general, all the aldehydes mentioned in the literature as suitable for ketone-aldehyde resin syntheses can be used. However, preferably formaldehyde and benzaldehyde are 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.
  • ketones B) according to formula II are acetophenone, ring-substituted acetophenone derivatives, such as hydroxy, methyl, ethyl, tert-butyl, cyclohexyl-acetophenone.
  • ketones C) may be included in a mixture, e.g. Acetone, 4-tert-butyl methyl ketone, methyl naphthyl ketone, hydroxynaphthyl ketone, methyl ethyl ketone, heptanone-2, pentanone-3, methyl isobutyl ketone, propiophenone, 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 having a total of 1 to 8 hydrocarbon atoms, individually or in mixture.
  • a mixture e.g. Acetone, 4-tert-butyl methyl ketone, methyl naphthyl ketone, hydroxynaphthyl ketone,
  • alkyl-substituted cyclohexanones mention may be made of 4-tert-amylcyclohexanone, 2-sec-butylcyclohexanone, 2-tert-butylcyclohexanone, 4-tert-butylcyclohexanone, 2-methylcyclohexanone and 3,3,5-trimethylcyclohexanone.
  • Benzoin or alkyl ethers such as methyl, ethyl, propyl, iso-butyl ethers of benzoin can be used as component C) in the subordinate degree to max. 9.9 mol% based on the ketone component can be used.
  • suitable ketones usually all CH-acidic ketones, as additional ketone C
  • the reaction can be carried out using an auxiliary solvent.
  • auxiliary solvent As suitable, alcohols such. As methanol or ethanol proved. It is also possible as auxiliary solvent water-soluble ketones such. As methyl ethyl ketone or acetone, which then react in the resin with.
  • B) and optionally C) 0.05 to 10 mol% (based on the ketone used) of at least one base are used.
  • A) can vary between 1 to 0.9 to 1 to 4. However, a ketone / aldehyde ratio of 1 to 1 to 1 to 2.5 is preferred.
  • the ketone component and the aldehyde component can be added in pure form or in solvents as mentioned above or aqueous. It is particularly preferred that an aqueous or alcoholic formaldehyde solution, trioxane and / or paraformaldehyde and / or benzaldehyde is used.
  • the ketone component Based on the total amount of ketones B) and C) used, the ketone component
  • the ketone component C) can be used in the range of 0 to 90 mol%, preferably 0 to 80 mol%, particularly preferably 0 to 75 mol%.
  • reaction products of A), B) and optionally C) are polymer-analogously reacted with the component D) by irradiation by means of UV light.
  • component D are generally suitable all unsaturated monomers which can be polymerized free-radically.
  • Preferably used are maleic acid, fumaric acid, acrylic acid and / or methacrylic acid, C 1 - C 4 alkyl ester of o-and / or cycloalkyl esters of methacrylic acid and / or acrylic acid, hydroxyalkyl acrylates and / or hydroxyalkyl methacrylates, glycidyl methacrylate, glycidyl acrylate, 1,2-Epoxybutylacrylat, 1 , 2-epoxybutyl methacrylate, 2,3-
  • (meth) acryloyl chloride (meth) acryloyl isocyanate, ⁇ , ⁇ -dimethyl-3-isopropenylbenzyl isocyanate, (meth) acrylic alkyl isocyanate having alkyl spacers which have from 1 to 12, preferably 2 to 8, particularly preferably 2 to 6, carbon atoms, such as For example, methacrylethyl isocyanate, methacrylic butyl isocyanate.
  • di-, tri- and / or tetra-acrylates are examples.
  • DPGDA di- (DPGDA) or tripropylene glycol diacrylate
  • HDDA hexanediol diacrylate
  • trimethylolpropane triacrylate all of which can be used in the literature for free-radical reactions as suitable higher-functional acrylates.
  • the ratio of the reaction product from A), B) and optionally C) and the unsaturated monomers D) can vary between 99: 1 to 1: 99, preferably 99: 1 to 20:80, particularly preferably 99: 1 to 40 to 60% by mass.
  • reaction products of A), B) and, if appropriate, C) with the unsaturated monomers D) can also be reacted in a polymer-analogous manner.
  • reaction-relevant reaction products of the components A), B) and optionally C) and D) have, depending on the nature and ratio of the components to each other
  • Melting ranges between 0 and 200 ° C, preferably 30 and 150 ° C, particularly preferably 40 and 125 ° C,
  • Average molecular weights of from 300 to 100,000, preferably from 400 to 10,000, more preferably from 500 to 5,000 g / mol,
  • the invention also provides a process for the preparation of polymeric reaction products, essentially comprising the reaction product
  • R H, unbranched or branched alkyl radical having 1 to 12 carbon atoms, aryl radical
  • radicals R 3 to R 7 are H, alkyl, OCH 3 , OC 2 H 5 , Cl, F, COO (C 1 -C 3 -alkyl), R 4 to R 6 additionally OH, SH
  • reaction product of A), B) and optionally C) is mixed with the component D) and is subsequently reacted, preferably in an inert gas atmosphere, by means of UV light irradiation.
  • the preparation of the invention based resins is carried out in the melt or in solution of a suitable organic solvent.
  • the reaction may optionally be accelerated by the addition of photosensitizers as catalysts, e.g. tertiary amines.
  • photosensitizers as catalysts, e.g. tertiary amines.
  • the solution or melt of the reaction product of A), B) and optionally C) is the component D), optionally in the presence of a suitable catalyst. Then the irradiation with suitable radiation preferably takes place in an inert gas atmosphere.
  • the optional solvent may, if desired, be separated after completion of the reaction, in which case a powder or a melt of the product according to the invention is then generally obtained.
  • polymerizable acids such as acrylic acid, methacrylic acid, fumaric acid and / or maleic acid
  • polymers are obtained which, after neutralization with suitable neutralizing agents, are unsaponifiable and water-dilutable.
  • Water dilutability can also be achieved by using, for example, polyether groups, sulfonate group- and / or amino-group-carrying monomers, if appropriate after neutralization with a suitable neutralizing agent.
  • the invention also relates to the use of the products according to the invention as the main component, base component or additional component in coating materials, adhesives, printing inks and inks, gel coats, polishes, glazes, pigment pastes, fillers, cosmetic articles and / or sealing and insulating materials.
  • the coating materials, adhesives, printing inks and inks, gelcoats, polishes, glazes, pigment pastes, fillers, cosmetics and / or sealants and insulating materials may also contain auxiliaries and additives such as, for example, inhibitors, water and / or organic solvents, neutralizing agents, surface-active substances, Oxygen scavengers and / or radical scavengers, catalysts, light stabilizers, color brighteners, thixotropic agents, skin preventatives, defoamers, antistatics, thickeners, thermoplastic additives, dyes, pigments, fire retardants, internal release agents, fillers and / or blowing agents.
  • auxiliaries and additives such as, for example, inhibitors, water and / or organic solvents, neutralizing agents, surface-active substances, Oxygen scavengers and / or radical scavengers, catalysts, light stabilizers, color brighteners, thixotropic agents, skin preventatives, de
  • the products according to the invention in particular improve the gloss, the course and the hardness of coating materials, adhesives, printing inks and inks, gelcoats, polishes, Glazes, pigment pastes, fillers, cosmetics and / or sealants and insulating materials. In part, improved adhesion is also observed.
  • the aqueous phase is separated from the resin phase, the resin is washed neutral with water at 100 ° C and devolatilized to 150 ° C in vacuo.
  • the produced resin is mixed in a ratio of 1: 4 with hydroxyethyl acrylate and methyl methacrylate in a ratio of 1: 1.
  • the average molecular weight increases after separation of the volatile constituents from about 700 g-mol "1 to about 2 250 g-mol " 1 .
  • the OH number is 137 mg KOH / g.
  • Example 10 g of the reaction product from Example 1 are dissolved in 10 ml of butyl acetate and 5 g of Vestanat IPDI (Degussa AG) and also 0.1 g of dibutyltin dilaurate are added. The solution is applied with a pulling frame on a glass plate and stored for 60 min at 120 ° C. The previously soluble film is no longer soluble in butyl acetate.

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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)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne des produits obtenus par des réactions à analogie polymère de produits constitués d'aldéhydes et de cétones et de monomères à polymérisation radicalaire. L'invention concerne également un procédé pour fabriquer ces produits et l'utilisation de ces produits.
EP05769643A 2004-08-26 2005-07-28 Produits de reactions a analogie polymere Withdrawn EP1786846A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004041196A DE102004041196A1 (de) 2004-08-26 2004-08-26 Produkte aus polymeranalogen Umsetzungen
PCT/EP2005/053677 WO2006021478A1 (fr) 2004-08-26 2005-07-28 Produits de reactions a analogie polymere

Publications (1)

Publication Number Publication Date
EP1786846A1 true EP1786846A1 (fr) 2007-05-23

Family

ID=35124335

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05769643A Withdrawn EP1786846A1 (fr) 2004-08-26 2005-07-28 Produits de reactions a analogie polymere

Country Status (10)

Country Link
EP (1) EP1786846A1 (fr)
KR (1) KR20070047312A (fr)
CN (1) CN1878803A (fr)
AU (1) AU2005276517A1 (fr)
BR (1) BRPI0514277A2 (fr)
CA (1) CA2577773A1 (fr)
DE (1) DE102004041196A1 (fr)
MA (1) MA29985B1 (fr)
TN (1) TNSN07072A1 (fr)
WO (1) WO2006021478A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2905598B1 (fr) * 2006-09-13 2009-12-04 Oreal Vernis a ongle comprenant une resine
US8914063B2 (en) 2007-05-15 2014-12-16 Lg Electronics Inc. Mobile terminal equipped with mode setting key and method of controlling the mobile terminal

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2438712A1 (de) * 1974-08-12 1976-02-26 Huber Fa Michael Muenchen Strahlungshaertende druckfarben
DE3820463A1 (de) * 1988-06-16 1989-12-21 Basf Ag Strahlungsempfindliche, ethylenisch ungesaettigte, copolymerisierbare verbindungen und verfahren zu deren herstellung
DE10338560A1 (de) * 2003-08-22 2005-03-17 Degussa Ag Strahlenhärtbare Harze auf Basis hydrierter Keton- und Phenol-Aldehydharze und ein Verfahren zu ihrer Herstellung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006021478A1 *

Also Published As

Publication number Publication date
WO2006021478A1 (fr) 2006-03-02
TNSN07072A1 (en) 2008-06-02
MA29985B1 (fr) 2008-12-01
CA2577773A1 (fr) 2006-03-02
CN1878803A (zh) 2006-12-13
DE102004041196A1 (de) 2006-03-02
AU2005276517A1 (en) 2006-03-02
KR20070047312A (ko) 2007-05-04
BRPI0514277A2 (pt) 2009-03-10

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