EP3080179A1 - Résines exemptes de formaldéhyde à base d'esters d'acide glyoxylique - Google Patents

Résines exemptes de formaldéhyde à base d'esters d'acide glyoxylique

Info

Publication number
EP3080179A1
EP3080179A1 EP13815704.5A EP13815704A EP3080179A1 EP 3080179 A1 EP3080179 A1 EP 3080179A1 EP 13815704 A EP13815704 A EP 13815704A EP 3080179 A1 EP3080179 A1 EP 3080179A1
Authority
EP
European Patent Office
Prior art keywords
amine
amide
formaldehyde
groups
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Withdrawn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
EP13815704.5A
Other languages
German (de)
English (en)
Inventor
Frank BÖRNER
Monika Jobmann
Mathias Hahn
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.)
Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
Original Assignee
Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
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 Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV filed Critical Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
Publication of EP3080179A1 publication Critical patent/EP3080179A1/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Withdrawn legal-status Critical Current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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
    • C08G12/32—Melamines
    • 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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/06—Amines
    • 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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds

Definitions

  • the present invention relates to a process for producing a formaldehyde-free resin and the resin obtainable by this process.
  • Synthetic resins or synthetic resins are relatively low molecular weight, curable materials obtained by reacting carbonyl compounds (in particular
  • Aldehydes such as formaldehyde
  • exemplary resins are amine resins, amide resins or resins of aromatic hydroxy compounds (e.g., phenolic resins).
  • Subsequent crosslinking (i.e., curing) of the resin yields a thermoset.
  • urea As components with amine or amide functionality z.
  • urea As urea, melamine, benzoguanamine, dicyandiamide and Acetylendihamstoff used, in particular urea and melamine resins are of industrial importance.
  • Suitable aromatic hydroxy compounds for the formation of resins are in particular phenols.
  • aldehyde component is preferably due to its high reactivity and low raw material price formaldehyde used. Resin synthesis often involves an excess of aldehyde to aid in the reactions between the two components. The residual contents of formaldehyde are correspondingly high. Formaldehyde can also be released by hydrolysis of the polycondensates.
  • a disadvantage is the formaldehyde outgoing health burden.
  • Formaldehyde is currently classified as a Category 2 carcinogenic hazardous substance under the European Regulation on classification, labeling and packaging of substances and mixtures. A classification into the category IB is planned. Because of this hazard potential, efforts have been made for many years to reduce the formaldehyde content. For this were different
  • formaldehyde scavengers that bind the free formaldehyde, such as.
  • amines urea, melamine
  • polyamines polyvinylamine
  • Pure glyoxylic acid-based amino resins also provide stable resins, but carry a high salt load since, prior to synthesis, they need to be neutralized to the amino resins with a base to cure. These salts readily absorb water and result in use (e.g., in
  • Wood materials to an increased swellability of the end products. Because the
  • Wood material production leads to long press times.
  • Resins based on dimethoxyglyoxal and melamine are also described for use in the microencapsulation of fragrances (WO2013 / 068255, US Pat.
  • Dialdehydes such as glyoxal provide even in the slightly basic addition of urea, melamine, benzoguanamine, Acetylendiharnstofff or dicyandiamide insoluble crosslinked gel structures. Because of this self-crosslinking already during the addition and the resulting high viscosities such resins have no technical relevance.
  • the invention has for its object to provide formaldehyde-free resins that are both stable on the one hand, but on the other hand can be well three-dimensional network setting appropriate curing conditions and thereby deliver end products that have the desired property profile in terms of strength, rigidity or resistance.
  • the present invention is to provide a process for producing a formaldehyde-free resin which satisfies the above-mentioned requirements.
  • the problem is solved by a process for producing a formaldehyde-free resin in which a glyoxylic acid ester with an amine, amide or aromatic
  • Glyoxylic acid ester based resins offer the advantage, compared to known resins, that the hydrophobicity of the resins can be adjusted by the type of ester. Since glyoxylic acid is either not or optionally used only in minor amounts, bring these resins in comparison to the Glyoxylklareharzen no or only a very low salt load in the final products.
  • Another advantage of using glyoxylic acid esters is that a small amount of glyoxylic acid is released upon curing by hydrolysis. This can act as a catalyst, so that no further catalysts must be added during curing.
  • the reactivity of the resins based on glyoxal acid esters is comparable to that of UF resins, which makes them more reactive than the classic formaldehyde-based melamine resins.
  • the glyoxylic acid ester is a
  • Glyoxylklarealkylester in particular a Glyoxylklare Ci_4-Alkylester.
  • Glyoxylic acid esters can be prepared by conventional methods known to the person skilled in the art
  • Synthetic methods are prepared or are commercially available.
  • glyoxylic acid esters can be obtained by esterification of the glyoxylic acid with an alcohol. If the esterification does not proceed quantitatively, glyoxylic acid is present in addition to the glyoxylic acid ester. In the method according to the invention can also be
  • glyoxylic acid is still present in the resin, in a preferred embodiment it can be neutralized with a base.
  • the amine, amide or aromatic hydroxy compound which is reacted with the glyoxylic acid ester to produce a formaldehyde-free resin may be those commonly used in the art
  • the starting amine or Struktur desipramine can for example 2-3 amine or
  • Amide groups i.e., diamines or diamide or triamine or triamide.
  • amines or amides having more than 3 amine or amide groups for example polyamide, polyacrylamide.
  • an aminotriazine, urea is used as the amine or amide
  • Diamidoalkan a polyacrylamide or a mixture of these compounds in question.
  • vegetable / animal amines / amides such as proteins, gelatin can be used.
  • Suitable aminotriazines are in particular amino-l, 3,5-triazines such as melamine, acetoguanamine and benzoguanamine.
  • suitable urea derivatives there may be mentioned, for example, alkylated ureas such as methyl urea or cyclic ureas such as acetylene diurea or ethylene urea.
  • suitable Thiourea derivatives may include, for example, cyclic thioureas such as
  • Ethylene thiourea As suitable imino urea derivatives, for example, cyclic imino ureas can be mentioned. As a suitable cyanamide, for example, dicyandiamide or cyanamide may be mentioned. Diamino-C 1-8 alkanes, for example, may be mentioned as suitable diaminoalkanes. Diamido-C 1-8 -alkanes, for example, may be mentioned as suitable diamidoalkanes.
  • Suitable aromatic hydroxy compounds are, for example, phenol (i.e., only one hydroxy group) or phenolic compounds having at least two
  • phenol groups For example, catechol, resorcinol, hydroquinone, phloroglucinol, hydroxyhydroquinone, pyrogallol or a mixture of at least two of these phenol compounds may be mentioned as preferred phenolic compounds.
  • the resin synthesis is carried out with an amine or amide, the molar ratio of the Glyoxylklareesters to the amine groups of the amine or the
  • Amide groups of the amide can be varied over a wide range.
  • the molar ratio of the glyoxylic ester to the amine groups of the amine or amide groups of the amide is preferably in the range of 0.5 / 3 to 3/3, more preferably 1/5 / 3 to 2.5 / 3 or 1, 8/3 to 2.2 / 3.
  • the molar ratio of the glyoxylic acid ester to the amine groups of the amine or the amide groups of the amide is preferably in the range from 0.2 / 2 to 2/2, more preferably 0.3 / 2 to 1, 5/2, more preferably 0.5 / 2 to 1, 5/2. If the resin synthesis is carried out with an aromatic hydroxy compound, the molar ratio of the Glyoxylklareesters to the aromatic
  • Hydroxy compound can be varied over a wide range. If the aromatic hydroxy compound has, for example, 3 hydroxyl groups, then the molar ratio of the glyoxylic acid ester to the aromatic one is
  • Hydroxy compound preferably in the range of 0.5 / 1 to 1/3, more preferably 1/1 to 1/2. If the aromatic hydroxy compound has, for example, 2 hydroxy groups, then the molar ratio of the glyoxylic acid ester to the aromatic one is
  • Hydroxy compound preferably in the range of 0.5 / 1 to 1/4, more preferably 1/1 to 1/2.
  • Glyoxylic acid ester reacts. Alternatively, however, it may be preferable that at least one amine group of the amine or an amide group of the amide or a reactive ring position of the aromatic hydroxy compound is not reacted with the glyoxylic acid ester.
  • a further aldehyde preferably a dialdehyde or a trialdehyde.
  • this gives a resin which still has free aldehyde groups.
  • Ring positions are present, these would be in a subsequent Reaction step directly accessible for reaction with the dialdehyde or trialdehyde. Suitable process conditions to ensure this are known to those skilled in the art.
  • Hydroxy compound can be added.
  • Suitable solvents for the reaction of the glyoxylic acid ester with the amine, the amide or the aromatic hydroxy compound are known in principle to the person skilled in the art.
  • an aqueous solvent is used.
  • hydrogen bond-breaking polar solvents can be used.
  • reaction conditions such as reaction temperature and pH
  • reaction temperature and pH Suitable reaction conditions for the reaction of the glyoxylic acid ester with the amine, amide or hydroxy aromatic compound are known in the art.
  • the reaction temperature may be, for example, in the range of 20 ° C to 100 ° C, more preferably in the range of 40 to 65 ° C.
  • the pH can vary over a wide range.
  • the pH may be, for example, in the range of 6 to 10, more preferably 7 to 8.5.
  • resins can also be stabilized without problems even at high solids contents (eg 60% by weight) (ie high storage stability).
  • the addition of stabilizing additives is not required.
  • the resin of the invention can For example, have a solids content of at least 40% by weight or even at least 55% by weight.
  • aldehyde is preferably a dialdehyde, a trialdehyde
  • Glyoxylic acid glycolaldehyde or furfural or a mixture of at least two of these aldehydes.
  • storage-stable resins can also be prepared with dialdehydes or trialdehydes if the amine or amide or the aromatic hydroxy compound is first reacted with the
  • Glyoxylic acid is reacted. In a known manner, while the
  • Process step prevents that it comes in the reaction with the dialdehyde or trialdehyde to an undesirable significant crosslinking.
  • Hemiacetal group represents a reactive group that is responsible for a later
  • Crosslinking reaction can be used, in this first reaction step, a "reactive protecting group" attached to the amine or amide group (ie a Group, on the one hand in a subsequent reaction with a di- or trialdehyde initially prevents unwanted premature crosslinking, but on the other hand has a reactive group, the later desired
  • one or more amine groups of the amine or amide groups of the amide or one or more positions of the aromatic phenol ring are initially blocked by a reactive protective group derived from the glyoxylic acid ester. If, in a further step, the dialdehyde or trialdehyde is added, it can initially react only with N atoms or reactive positions of the aromatic ring which have not yet been blocked with a protective group in the first step. In addition, since the reaction of the glyoxylic acid ester with the amine or amide is an equilibrium reaction in the first step, the dialdehyde or trialdehyde in the second step can partially replace the protective groups derived from the glyoxylic acid ester.
  • the resin has free aldehyde groups.
  • the presence of free aldehyde groups can increase the reactivity in the setting of suitable conditions and thus the production of a crosslinked
  • Dialdehydes or trialdehydes which can be reacted with amines or amides or aromatic hydroxy compounds are known per se to a person skilled in the art.
  • glyoxal or a dialdehyde of the formula OHC- (CH 2 ) i_ 3 -CHO ie malonaldehyde, succinic dialdehyde, glutaraldehyde
  • a suitable trialdehyde for example, 2,4,6-tris (p-formylphenoxy) -1, 3,5-triazine can be mentioned.
  • dialdehyde or trialdehyde it is possible for the dialdehyde or trialdehyde to be added to the product from the first step, which is preferably present in an aqueous solution.
  • the product from the first step e.g., in the form of an aqueous solution
  • the product from the first step is added to the
  • Dialdehyde or trialdehyde is added. In both cases, it is preferred that one component of the other component is continuously metered. While added slowly enough in the first case, so that in the reaction medium during the reaction always only a low concentration of not
  • the product from the first step is preferably not isolated, but used in the form of the aqueous solution in which it was prepared in the first step, for the reaction with the dialdehyde or trialdehyde in the second step.
  • the amount of dialdehyde or trialdehyde added in the second step can be varied over a wide range.
  • the molar ratio of the dialdehyde or trialdehyde to the amine groups or amide groups is preferably in the range from 0.1 / 3 to 5/3, more preferably 0.5 / 3 to 3 / 3 or 0.8 / 3 to 2.2 / 3.
  • the molar ratio of the dialdehyde or trialdehyde to the amine groups or amide groups is preferably in the range from 0.1 / 3.9 to 3.9 / 0.1, more preferably 0, 3 / 1.7 to 1.7 / 0.3, more preferably 0.5 / 1.5 to 1.5 / 0.5.
  • the molar ratio of the dialdehyde or trialdehyde added in the second step to the glyoxylic acid ester added in the first step can be, for example, in the range from 1 / 0.01 to 1/3 or 1/0, 2 to 1/2 or even 1 / 0.5 to 1 / 1.5. If the amine or amide has three amine or amide groups, then the molar ratio of the dialdehyde or trialdehyde added in the second step to the glyoxylic acid ester added in the first step can be in the range from 1 / 0.01 to 1/5 or 1.5 / 0.2 to 1.5 / 2 or even 2 / 0.3 to 2/1.
  • the molar ratio of the dialdehyde or trialdehyde to the aromatic one is
  • Hydroxy compound preferably in the range of 1 / 0.1 to 1 / 2.5, more preferably 1 / 0.1 to 1 / 1.5. If the aromatic hydroxy compound has 2 hydroxyl groups, then the molar ratio of the dialdehyde or trialdehyde to the aromatic one is Hydroxy compound preferably in the range of 1 / 0.1 to 1 / 3.5, more preferably 1 / 0.1 to 1/2.
  • reaction conditions such as reaction temperature and pH
  • reaction temperature and pH for the reaction of an amine or amide or an aromatic
  • Hydroxy compound with the dialdehyde or trialdehyde are known in principle to the person skilled in the art.
  • the reaction temperature in the second step may be, for example, in the range of 20 ° C to 100 ° C, more preferably 40 ° C to 65 ° C.
  • the pH may be, for example, in the range of 6 to 10, more preferably 7 to 8.5.
  • oligomers can be formed with very short sequences and the resins can also be stabilized without problems even at high solids contents (eg 60% by weight) , Even in the case of readily soluble compounds such as urea or guanidine, the reaction products remain so low in viscosity due to the reactive protective group derived from the glyoxylic acid ester that stabilization takes place even at high levels
  • the resin is characterized by having free aldehyde groups which increase the reactivity in setting suitable conditions and thus assist in the production of a crosslinked final product.
  • the reactivity of the resin is also due to the presence of the reactive
  • the produced resins can be stabilized, for example by
  • Cooling e.g., to a temperature below 30 ° C, more preferably
  • the present invention relates to a process for producing a crosslinked material, comprising
  • Suitable conditions for the crosslinking of a resin for the production of a crosslinked material are basically known to the person skilled in the art. As already mentioned above, another advantage of using
  • Glyoxylklaestern in that when hardening a small amount of glyoxylic acid is released by hydrolysis. This can act as a catalyst, so that no further catalysts must be added during curing. In a preferred embodiment, therefore, according to the
  • thermosets resin for curing no external catalyst supplied. Since there are many hydrogen bonds in the material, it is also suitable for microwave treatment during the cross-linking step (eg in the form of micro wave postcuring).
  • Crosslinked materials are also referred to as thermosets.
  • the presence of free primary amide groups can increase the reactivity of the resin.
  • the urea or polyamide or the formaldehyde-free resin before and / or during crosslinking can increase the reactivity of the resin.
  • Polyacrylamide (preferably each in the form of a solution) was added.
  • the addition of the amide is carried out in an amount such that the number of free primary amide groups is less than the number of free aldehyde groups.
  • the present invention relates to a formaldehyde-free resin obtainable by the above-described process, that is, by reacting a glyoxylic acid ester with an amine or an amide or an aromatic hydroxy compound.
  • the resin has free aldehyde groups.
  • the resin according to the invention in the resin according to the invention:
  • Embodiment may have free aldehyde groups.
  • the solids content of the resin can be varied over a wide range.
  • the solids content is at least 40% by weight.
  • the concentration or the solids content of the resin is in the range of 40 to 80% by weight or 55 to 70% by weight.
  • the resin of the invention shows good storage stability even at high solids content. Stabilizing additives are not required.
  • the resin does not contain a polymeric additive.
  • the present invention relates to a crosslinked material obtainable from the above-described resin.
  • the crosslinked material is obtained by curing the resin appropriately, i. is subjected to crosslinking.
  • foams or foamed materials or also fibers can be mentioned.
  • a further advantage of products based on the glyoxylic acid ester resins is that the partial hydrolysis of the ester groups can generate acidic and thus fungicidally active surfaces. At the same time, this acidic surface can catalyze the resin system because the condensation catalyst (acid) is permanently present in the final products. In the case of mechanical damage or hydrolysis in the event of water, a self-healing effect can therefore be achieved by renewed condensation even at room temperature.
  • Example 7 For the resin synthesis in Example 7, the isopropanol of the organic phase was distilled off after the phase separation. The product was made with 100g of water
  • the temperature-dependent viscosity curve of a conventional melamine-formaldehyde resin (MF resin) is shown in FIG.
  • curing began at a temperature of 110 ° C.
  • the onset of cure could be shifted to a significantly lower temperature, although no acid was added as a curing catalyst.
  • the resin contains free aldehyde groups and has a high storage stability at room temperature.
  • the free aldehyde groups in the curing of these resins in addition to the condensation and an addition reaction allows, which increases the reactivity.
  • Example 5 Synthesis of Resin 3 - Glyoxylic Acid Ester / Glyoxylic Acid Resins Based on Melamine (Esters from Example 2)
  • the resin contains free aldehyde groups and has a high storage stability at room temperature.
  • the free aldehyde groups in the curing of these resins in addition to the condensation and an addition reaction allows, which increases the reactivity.
  • Glyoxylic acid isopropyl ester was neutralized after addition with 100 g of water with (2 drops) of potassium carbonate solution and treated with 8.46 g (0.067 mol) of melamine. After stirring at 56 ° C. for 1.5 h, a highly viscous resin was obtained.

Abstract

La présente invention concerne un procédé pour préparer une résine exempte de formaldéhyde, un ester d'acide glyoxylique réagissant avec une amine, un amide ou un composé hydroxy aromatique, ainsi qu'une résine obtenue par ce procédé.
EP13815704.5A 2013-12-12 2013-12-12 Résines exemptes de formaldéhyde à base d'esters d'acide glyoxylique Withdrawn EP3080179A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2013/076367 WO2015086073A1 (fr) 2013-12-12 2013-12-12 Résines exemptes de formaldéhyde à base d'esters d'acide glyoxylique

Publications (1)

Publication Number Publication Date
EP3080179A1 true EP3080179A1 (fr) 2016-10-19

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EP13815704.5A Withdrawn EP3080179A1 (fr) 2013-12-12 2013-12-12 Résines exemptes de formaldéhyde à base d'esters d'acide glyoxylique

Country Status (2)

Country Link
EP (1) EP3080179A1 (fr)
WO (1) WO2015086073A1 (fr)

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DE102020114289A1 (de) 2020-05-28 2021-12-02 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein Funktionalisierte Aminoharz-haltige Partikel
CN113563193A (zh) * 2020-08-24 2021-10-29 江苏禾本生化有限公司 一种溴螨酯新的制备方法

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