RU2484085C2 - Dialdimine, dialdimine-containing emulsion and two-component polyurethane composition and use thereof - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: invention relates to a dialdimine of formula

, where R is a radical of formula

, where R¹ and R² are either independently univalent hydrocarbon radicals with 1-6 C atoms; R³ is a hydrogen atom; R⁴ is a radical of formula

, where R⁵ is a linear or branched alkyl radical with 1-12 C atoms, A is a C₄-C₁₀ diamine group DA with two primary aliphatic amino groups after removal of both primary aliphatic amino groups and containing two ether groups, Q is a diisocyanate group DI after removal of both isocyanate groups; n equals 0 or an integer from 1 to 15; and where A and R do not contain groups which, in the absence of water, are capable of reacting with isocyanate groups. The invention also relates to a method of producing said dialdimine and use of dialdimine in emulsions for use as a curing or accelerating component for polymers with isocyanate groups.

EFFECT: invention provides two-component compositions which are fast-hardening and have exclusively high strength in the early period and do not have undesirable weak points.

22 cl, 2 tbl, 4 ex, 11 dwg

Description

Technical field

The invention relates to the field of polyaldimines, emulsions containing aldimines, as well as two-component polyurethane compositions.

State of the art

Aldimines have long been used as blocked amines. In particular, polyaldimines were introduced as latent hardeners into compositions that contained polymers with isocyanate groups and were used, for example, as adhesives or sealants. These compositions solidified upon contact with water, with aldehydes being released. These aldehydes in most cases were very odorous and interfered with work, therefore, significantly limited the possibility of using the compositions. In patent WO 2004/013200 A1, polyurethane compositions were proposed containing polyaldimines, which harden without an interfering odor.

One-component polyurethane compositions that contain polymers with isocyanate groups and cure with air moisture have long been used, for example, as adhesives or sealants or as coatings. Since these compositions usually cure slowly, it has been suggested many times to accelerate cure and achieve strength by mixing the second component, which contains water. However, these two-component compositions had a major drawback because they were prone to bubble formation. When mixing both components in layers, they give in most cases reduced mechanical strength, in particular, shortly after mixing. The second component, containing water, in practically suitable systems contains for the most part an organic VOC solvent, in particular N-alkylpyrrolidone, which is associated with major drawbacks due to toxicological and hygienic technological reasons.

WO 2005/037885 A1 discloses two-component polyurethane compositions in which a second component is mixed with a first component containing an isocyanate-group polyurethane prepolymer, which, along with water, contains a low odor polyaldimine. These compositions, although they provide a reduction (formation) of bubbles and accelerated curing, however, their curing and achievement of strength is still too slow for many applications.

SUMMARY OF THE INVENTION

The objective of the invention is therefore to create a two-component polyurethane composition, which overcomes the disadvantages of the modern level of technology and, in particular, provides high strength in the early period.

It has been unexpectedly found that an emulsion based on dialdimines of the formula (I) is widely applicable as a curing or accelerating component for polymers with isocyanate groups, in particular for polyurethanes with isocyanate groups. In particular, it is therefore possible to obtain paste-like curing or accelerating components that lead to very high strength in the early period, have good pumpability and can be formulated without a VOC solvent, in particular without N-alkylpyrrolidone. These components allow for excellent homogeneous or non-homogeneous, in particular, also layer-by-layer mixing with components containing polyurethanes with isocyanate groups, the bicomponent compositions obtained in this way quickly cure, have high strength in the early period and at the same time remain without interfering weak points, in particular , without weak spots in / or between layers, especially in those cases when the layers are relatively thick. Despite the rapid curing, these compositions with both layered and homogeneous mixing exhibit a sufficiently long exposure time, which allows, for example, to reliably perform bonding.

The dialdimines of formula (I) can be prepared in a simple manner from readily available dialdimines, diisocyanates and water.

Thus, the present invention relates to dialdimines of formula (I) according to paragraph 1, the method for their preparation according to paragraph 11, emulsions containing such aldimines according to paragraph 12, and their use as curing components or accelerating components for an adhesive, a sealing substance or coating substances that contain polymers with isocyanate groups, according to paragraph 14.

Additionally, the invention relates to two-component compositions according to paragraph 15, obtained from them mixed or partially mixed compositions according to paragraph 16, the use of two-component compositions as an adhesive, sealant, or coating, or layer according to paragraph 17, the method of bonding, sealing and obtaining a coating according to paragraphs 18, 19 and 20, as well as to the resulting products under paragraph 24.

Preferred embodiments of the invention are subject to dependent claims.

The implementation of the invention

The present invention relates to dialdimines of the formula (I)

where R is the ALD aldehyde residue after removal of the aldehyde group, and A is the diamine DA residue with two primary aliphatic amino groups after the removal of both primary amino groups. Moreover, residues A and R do not contain groups which, in the absence of water, are reactive with respect to isocyanate groups, in particular (do not contain) hydroxyl groups, primary or secondary amino groups, mercapto groups and other groups with an active (atom) hydrogen.

Q represents the remainder of the diisocyanate DI after removal of both isocyanate groups and n is 0 or an integer from 1 to 15.

The term “primary amino group” in the proposed document means an NH ₂ group that is linked to one organic radical, while the term “secondary amino group” means an NH group that is linked to two organic radicals, which together can also be part of a cycle .

As "aliphatic amino group" is meant an amino group that is bonded to an aliphatic, cycloaliphatic or arylaliphatic radical. Moreover, it differs from the "aromatic amino group", which is directly linked to an aromatic or heteroaromatic radical, such as, for example, in aniline or 2-aminopyridine.

The term "polymer" in the proposed document includes, on the one hand, a set of chemically uniform macromolecules, differing, however, with respect to the degree of polymerization, molar mass and chain length, which are obtained by the polymer formation reaction (polymerization, polyaddition, polycondensation). On the other hand, the concept also includes derivatives of the specified set of macromolecules and the (obtained) polymer formation reaction, that is, compounds that can be obtained by transformations, such as, for example, addition or substitution of functional groups of preformed macromolecules, and can be chemically uniform or chemically not uniform. The concept further includes the so-called prepolymers, which means reactive oligomeric foradducts whose functional groups are involved in the construction of macromolecules.

The term "polyurethane" includes all polymers that are obtained by the so-called method of polyaddition of diisocyanate. It also includes those polymers which are almost or completely free from urethane groups. For example, polyurethanes are polyether polyurethanes, polyester polyurethanes, polyether polyureas, polyureas, polyester polyureas, polyisocyanurates and polycarbodiimides.

"Room temperature" means a temperature of 25 ° C.

The names of substances beginning with "poly", such as polyaldimine, polyisocyanate, polyol or polyaldehyde, in the present document means substances that formally contain two or more functional groups in the molecule that are found in their name.

As the aldehyde ALD, all known aldehydes are fundamentally applicable. Said aldehydes may be aliphatic, cycloaliphatic, arylaliphatic or aromatic aldehydes and may be monoaldehydes or polyaldehydes.

Suitable aliphatic, cycloaliphatic or arylaliphatic ALD aldehydes are, for example, propionic aldehyde, butyric aldehyde, isobutyraldehyde, 2-methylbutyraldehyde, 2-ethylbutyraldehyde, isomederyldehyde, 2-methyldehyde-merdeyanide , 2-ethylhexanal, octanal, isooctanal, nonanal, decanal, undecanal, 2-methylundecanal, dodecanal, cyclopropanecarboxaldehyde, cyclopentanecarboxaldehyde, cyclohexylcarboxaldehyde, 1,2,3,6-tetra agidrobenzaldehyde, phenylacetaldehyde, 2-phenylpropionic aldehyde (hydratropic aldehyde) and 2-methyl-3-phenylpropionic aldehyde.

Suitable aromatic aldehydes ALD are, for example, benzaldehyde, 2-, 3- and 4-toluyl aldehydes,

4-ethyl-, 4-propyl- and 4-isopropyl- and 4-butylbenzaldehydes, 2,4-dimethylbenzaldehyde, 2,4,5-trimethylbenzaldehyde, 4-acetoxybenzaldehyde, 4-anisaldehyde, 4-ethoxybenzaldehyde, isomeric di- and trialkoxybenzaldehydes, 2-, 3- and 4-nitrobenzaldehydes, 2-, 3- and 4-formylpyridines, 2-furfural, 2-thiophenecarbaldehyde, 1- and 2-naphthylaldehydes, 3- and 4-phenoxybenzaldehydes; quinoline-2-carbaldehyde and its 3-, 4-, 5-, 6-, 7- and 8-positional isomers, anthracene-9-carbaldehyde, phthalaldehyde, isophthalic aldehyde and terephthalaldehyde.

It has been shown that, in particular, aldehydes suitable for the ALD aldehyde are those which in the α-position to the carbonyl group do not contain the CH group and therefore cannot form tautomeric enols.

Thus, the aldehyde ALD is, in particular, an aldehyde of the formula (II-a) or an aldehyde of the formula (II-b).

where R ¹ and R ² are either independently monovalent hydrocarbon radicals with from 1 to 12 C atoms, or together with a divalent hydrocarbon radical with from 4 to 20 C atoms, are part of, if necessary, a substituted carbocyclic ring with from 5 to 8, preferably with 6, C atoms;

Y ¹ represents a monovalent hydrocarbon radical, which, if necessary, contains at least one heteroatom, in particular oxygen in the form of an ether, carbonyl or ester group;

Y ² represents either a substituted or unsubstituted aryl or heteroaryl group with a ring size of 5 to 8, preferably 6 atoms, or a C (= O) -R ⁶ group in which R ⁶ is a hydrogen atom or an alkoxy group, or substituted or unsubstituted an alkenyl or arylalkenyl group with at least 6 C atoms.

Suitable aldehydes of formula (II-a) are, for example, 2,2-dimethylpropanal (pivalic aldehyde), 2,2-dimethylbutanal, 2,2-diethylbutanal, 1-methylcyclopentanecarboxaldehyde, 1-methylcyclohexanecarboxaldehyde, as well as the ethers and esters described below. esters of 2,2-disubstituted 3-hydroxypropanals,

-butanal or similar higher aldehydes, in particular 2,2-dimethyl-3-hydroxypropanal.

Suitable aldehydes of the formula (II-b) are, for example, aromatic aldehydes already mentioned as ALD aldehyde, as well as glyoxal, glyoxylic acid esters such as glyoxylic acid methyl ester, cinnamaldehyde and substituted cinnamaldehydes.

In the first embodiment, dialdimines of the formula (I) in which the radicals R have the formula (II) are particularly suitable.

where R ³ represents a hydrogen atom, or an alkyl or arylalkyl group, in particular with 1 to 12 C atoms; and R ⁴ represents a hydrocarbon radical with from 1 to 30 C-atoms, optionally containing a heteroatom.

In a second embodiment, dialdimines of the formula (I) are particularly suitable in which the radicals R have the formula (III).

where R ⁵ represents either a linear or branched alkyl radical with from 1 to 30 C-atoms, optionally with cyclic components and, if necessary, with at least one heteroatom, in particular oxygen, in the form of an ether or a carbonyl or ester group, or a mono- or polyunsaturated linear or branched hydrocarbon radical with from 1 to 30 C atoms.

The specified radical R corresponds to the formula (II), in which R ⁴ has the formula (III ').

Dialdimines of the formula (I) are preferred which contain the radical R of the formula (II) or the formula (III) in which the radical R ⁴ is a hydrocarbon radical with from 11 to 30 C atoms; if necessary containing heteroatoms; or in which the R ⁵ moiety is a linear or branched alkyl radical with from 11 to 30 C atoms, optionally with cyclic components and, if necessary, with at least one heteroatom, in particular oxygen in the form of ether or a carbonyl or ester group, or a mono- or polyunsaturated linear or branched hydrocarbon radical with from 11 to 30 C atoms.

These preferred dialdimines of the formula (I) are characterized in that they themselves or the aldehydes formed upon their hydrolysis are odorless. The term “odorless” in this document is understood to mean a substance that smells so faintly that for most human individuals it is odorless, that is, it is not perceived by the nose.

Particularly preferred aldehydes of the formula (II-a) are, on the one hand, the aldehydes ALD1 of the formula (II-a '), i.e. aldehydes ALD with the remainder R of the formula (II).

Aldehydes ALD1 of the formula (II-a ') are ethers of aliphatic, arylaliphatic or cycloaliphatic 2,2-disubstituted 3-hydroxyaldehydes with alcohols or phenols of the formula R ⁴ -OH, for example, fatty alcohols or phenols. Suitable 2,2-disubstituted 3-hydroxyaldehydes, for their part, can be prepared by aldol condensation reactions, in particular cross-aldol condensation reactions, between primary and secondary aliphatic aldehydes, in particular formaldehyde, and secondary aliphatic, secondary aryl aliphatic or secondary aldehydes such as, for example, 2-methylbutyraldehyde, 2-ethylbutyric aldehyde, 2-methylvalerianic aldehyde, 2-ethylcapronylaldehyde, cyclopentanecarboxaldehyde, cycloh ksankarboksaldegid, 1,2,3,6-tetragidrobenzaldegid, 2-methyl-3-phenylpropionaldehyde, 2-phenylpropionaldehyde (gidrotropovy aldehyde) or diphenylacetaldehyde. Examples of suitable 2,2-disubstituted 3-hydroxyaldehydes are 2,2-dimethyl-3-hydroxypropanal, 2-hydroxymethyl-2-ethylbutanal, 2-hydroxymethyl-2-ethylbutanal, 2-hydroxymethyl-2-methylpentanal, 2-hydroxymethyl-2 ethylhexanal, 1-hydroxymethylcyclopentanecarboxaldehyde, 1-hydroxymethylcyclohexanecarboxaldehyde, 1-hydroxymethylcyclohex-3-enecarboxaldehyde, 2-hydroxymethyl-2-methyl-3-phenylpropanal, 3-hydroxy-2-methyl-2-phenylpropan and diphenylpropanal.

Examples of ALD1 aldehydes of formula (II-a ') are 2,2-dimethyl-3-phenoxypropanal, 3-cyclohexyloxy-2,2-dimethylpropanal, 2,2-dimethyl-3- (2-ethylhexyloxy) propanal, 2,2- dimethyl-3-lauroxypropanal; and 2,2-dimethyl-3-stearoxypropanal.

Particularly suitable aldehydes of the formula (II-a), on the other hand, are aldehydes ALD2 of the formula (II-a "), that is, ALD aldehydes with the remainder R of the formula (III).

ALD2 aldehydes of the formula (II-a ") are esters of the already described 2,2-disubstituted 3-hydroxyaldehydes with suitable carboxylic acids.

Examples of suitable carboxylic acids are saturated aliphatic carboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valerianic acid, caproic acid, 2-ethylcaproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic I am acid, arachinic acid; monounsaturated aliphatic carboxylic acids such as palmitoleic acid, oleic acid, erucic acid; polyunsaturated aliphatic carboxylic acids such as linoleic acid, linolenic acid, eleostearic acid, arachidonic acid; cycloaliphatic carboxylic acids, such as cyclohexanecarboxylic acid; arylaliphatic carboxylic acids such as phenylacetic acid; aromatic carboxylic acids such as benzoic acid, naphthoic acid, toluic acid, anisic acid; isomers of these acids; mixtures of fatty acids (obtained by) the technical saponification of natural oils and fats, such as, for example, rapeseed oil, sunflower oil, linseed oil, alemi oil, coconut oil, palm kernel oil and palm oil; as well as monoalkyl and aryl esters of dicarboxylic acids, which are obtained by simple esterification of dicarboxylic acids, such as succinic acid, glutaric acid, adipic acid, pimelic acid, pith acid, azelaic acid, sebacic acid, 1,12-dodecandicarboxylic acid, maleic acid, fumaric acid, hexahydrophthalic acid, hexahydroisophthalic acid, hexahydroterephthalic acid, 3,6,9-trioxaundecandicarboxylic acid and the like derivatives of polyethylene glycol, alcohols such as m ethanol, ethanol, propanol, butanol, higher homologues and isomers of these alcohols.

Preferred ALD2 aldehydes of formula (II-a ") are 3-benzoyloxy-2,2-dimethylpropanal, 3-cyclohexanoyloxy-2,2-dimethylpropanal, 2,2-dimethyl-3- (2-ethylhexyloxy) propanal, 2,2- dimethyl-3-lauroyloxypropanal, 2,2-dimethyl-3-myristoyloxypropanal, 2,2-dimethyl-3-palmitoyloxypropanal, 2,2-dimethyl-3-stearoyloxypropanal, as well as similar esters of other 2,2-disubstituted 3-hydroxyaldehydes.

In one particularly preferred embodiment, R ^{5 is} selected from the group consisting of phenyl, cyclohexyl, 2-ethylhexyl and C ₁₁ -, C ₁₃ -, C ₁₅ - and C ₁₇ -alkyl groups.

As the aldehyde ALD2 of formula (II-a "), 2,2-dimethyl-3-lauroloxypropanal is most preferred.

In one of the preferred methods for producing the aldehyde ALD2 of the formula (II-a "), 2,2-disubstituted 3-hydroxyaldehyde, in particular 2,2-dimethyl-3-hydroxypropanal, which, if necessary, can be obtained in situ, for example, from formaldehyde (or paraformaldehyde) and isobutyric aldehyde is reacted with a carboxylic acid to form the corresponding ester. This esterification can be carried out without using a solvent according to the known method described, for example, in Houben-Weyl, "Methoden der organischen Chemie", volume VIII, pages VIII 516-528.

Aldehydes ALD2 of the formula (II-a ') are preferable to aldehydes ALD1 of the formula (II-a') due to the simplicity of their preparation.

In a particularly preferred embodiment, the aldehyde ALD is odorless. Odor-free ALD aldehydes, on the one hand, are, in particular, ALD1 aldehydes of the formula (II-a '), in which the R ⁴ residue is a hydrocarbon radical with from 11 to 30 C atoms, which, if necessary, contains a heteroatom.

On the other hand, odor-free aldehydes ALD are, in particular, aldehydes ALD2 of formula (II-a "), in which the residue R ⁵ represents either a linear or branched alkyl group with from 11 to 30 carbon atoms, if necessary , with cyclic components and, if necessary, with at least one heteroatom, in particular with at least one ether, or a mono- or polyunsaturated linear or branched hydrocarbon chain with from 11 to 30 carbon atoms.

Examples of odorless aldehydes ALD2 of formula (II-a ") are the esterification products of the already mentioned 2,2-disubstituted 3-hydroxyaldehydes with carboxylic acids, such as, for example, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, arachinic acid, palmitoleic acid, oleic acid, erucic acid, linoleic acid, linolenic acid, eleostearic acid, arachidonic acid, and mixtures of fatty acids (resulting) from the technical saponification of natural oils and fats, such as, for example, rapeseed oil, sunflower oil, linseed oil, alemi oil, coconut oil, palm kernel oil and palm oil.

Preferred odorless ALD2 aldehydes are 2,2-dimethyl-3-lauroloxypropanal, 2,2-dimethyl-3-myristoyloxypropanal, 2,2-dimethyl-3-palmitoyloxypropanal and 2,2-dimethyl-3-stearoyloxypropanal. Especially preferred is 2,2-dimethyl-3-lauroloxypropanal.

Diamine DA with two primary aliphatic amino groups contains two primary amino groups that are associated with one aliphatic, cycloaliphatic or arylaliphatic residue.

Suitable diamine DA are aliphatic, cycloaliphatic or arylaliphatic diamines, for example, ethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 2-methyl-1,2-propanediamine, 2,2-dimethyl-1,3-propanediamine, 1,3-butanediamine, 1,4-butanediamine, 1,3-pentanediamine (DAMP), 1,5-pentanediamine, 1,5-diamino-2-methylpentane (MPMD), 1,6-hexanediamine, 2,5- dimethyl-1,6-hexanediamine, 2,2,4-trimethylhexamethylenediamine, 2,4,4-trimethylhexamethylenediamine, 1,7-heptanediamine, 1,8-octanediamine, 1,9-nonanediamine, 1,10-decanediamine, 1, 11-undecandiamine, 1.12-dodecandiamine and methyl bis- (3-aminopropyl) amine, 1,2-, 1,3- and 1 , 4-diaminocyclohexanes, bis- (4-aminocyclohexyl) methane, bis- (4-amino-3-methylcyclohexyl) methane, bis- (4-amino-3-ethylcyclohexyl) methane, bis- (4-amino-3, 5-dimethylcyclohexyl) methane, 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (= isophorondiamine or (IPDA), 2- and 4-methyl-1,3-diaminocyclohexanes and mixtures thereof, 1,3- and 1,4-bis- (aminomethyl) cyclohexanes, 1-cyclohexylamino-3-aminopropane, 2,5 (2,6) -bis- (aminomethyl) bicyclo [2.2.1] heptane (NBDA obtained from Mitsui Chemicals), 3 (4), 8 (9) -bis- (aminomethyl) tricyclo [5.2.1.0 ^2.6 ] decane, 1,4-diamino-2,2,6-trimethylcyclohexane (TMCDA), 3,9-bis- (3 -aminopropyl) -2,4,8,10-tetraoxaspiro [5 .5] undecane, as well as 1,3- and 1,4-xylylenediamines.

Aliphatic diamines containing ether groups, for example, bis (2-aminoethyl) ether, 3,6-dioxaoctane-1,8-diamine, 4,7-dioxadecane-1,10-diamine, are particularly suitable as diamine DA. 4,7-dioxadecane-2,9-diamine, 4,9-dioxadodecane-1,12-diamine, 5,8-dioxadodecane-3,10-diamine and higher oligomers of these diamines, as well as polyoxyalkylenediamines. The latter are the typical products of the amination polyoxyalkylenediols and can be prepared, for example, under the name Jeffamine ^® (from Huntsman Chemicals), called polyether amine (from BASF) or under the name MS Amine ^® (from Nitroil). Particularly suitable polyoxyalkylene diamines are Jeffamine ^® D-230, Jeffamine ^® D-400, Jeffamine ^® D-2000, Jeffamine ^® D-4000, Jeffamine ^® XTJ-511, Jeffamine ^® ED-600, Jeffamine ^® ED-900, Jeffamine ^® ED-2003, Jeffamine ^® XTJ-568, Jeffamine ^® XTJ-569, Jeffamine ^® XTJ-523, Jeffamine ^® XTJ-536, Jeffamine ^® XTJ-542, Jeffamine ^® XTJ-559, Polyetheramin D 230, Polyetheramin D 400 and Polyetheramin D 2000, PC Amine ^® DA 250, PC Amine ^® DA 400, PC Amine ^® DA 650, and PC Amine ^® DA 2000.

As diamine DA, aliphatic diamines containing ether groups are preferred, in particular, aliphatic diamines containing ether groups selected from the group consisting of bis (2-aminoethyl) ether, 3,6-dioxaoctane-1,8- diamine, 4,7-dioxadecane-1,10-diamine, 4,7-dioxadecane-2,9-diamine, 4,9-dioxadodecane-1,12-diamine, 5,8-dioxadodecane-3,10-diamine and higher oligomers of these diamines, as well as polyoxyalkylene diamines of the formula (V ').

where each of g, h and i is equal to 0 or an integer from 1 to 40, and the sum of g, h and i ≥1.

Preferably, the diamine DA of formula (V ′) has a molecular weight of from 200 to 5000 g / mol.

Examples of polyoxyalkylene diamines of the formula (V ') are commercially available types Jeffamine ^® D-230, Jeffamine ^® D-400, Jeffamine ^® D-2000, Jeffamine ^® D-4000, Jeffamine ^® XTJ-511, Jeffamine ^® ED-600, Jeffamine ^® ED-900 and Jeffamine ^® ED-2003 (all from Huntsman Chemical); Polyetheramin D 230, Polyetheramin D 400 and Polyetheramin D 2000 (all from BASF); as well as PC Amine ^® DA 250, PC Amine ^® DA 400, PC Amine ^® DA 650 and PC Amine ^® DA 2000 (all from Nitroil).

Diisocyanate DI is either a monomeric diisocyanate, or an oligomeric derivative thereof, or a polyurethane P containing an isocyanate group.

Suitable monomeric diisocyanates or their oligomeric derivatives are, for example, 1,6-hexamethylene diisocyanate (HDI), 2-methylpentamethylene-1,5-diisocyanate, 2,2,4- and 2,4,4-trimethyl-1,6-hexamethylenediisocyanates (TMDI), 1,10-decamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, lysine diisocyanates and lysine ester, cyclohexane-1,3-diisocyanate, cyclohexane-1,4-diisocyanate and any mixtures of these isomers, 1-methyl-2,4 - and -2,6-diisocyanatocyclohexanes and any mixtures of these isomers (HTDI or H ₆ TDI), 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (= isophore ondiisocyanate or IPDI), perhydro-2,4'-diphenylmethanediisocyanate and perhydro-4,4'-diphenylmethane diisocyanate (HMDI or H ₁₂ MDI), 1,4-diisocyanato-2,2,6-trimethylcyclohexane (TMCDI), 1,3 - and 1,4-bis (isocyanatomethyl) cyclohexanes, meta- and para-xylylenediisocyanates (m- and p-XDI), meta- and para-tetramethyl-1,3- and 1,4-xylylenediisocyanates (m- and p- TMXDI), bis- (1-isocyanato-1-methylethyl) -naphthalene, 2,4- and 2,6-toluene diisocyanates and any mixtures of these isomers (TDI), 4,4'-, 2,4'- and 2, 2'-diphenylmethanediisocyanates and any mixture of these isomers (MDI), 1,3- and 1,4-phenylenediisocyanates, 2,3,5,6-tetramethyl-1,4-diisocyanato benzene, naphthalene-1,5-diisocyanate (NDI), 3,3'-dimethyl-4,4'-diisocyanatodiphenyl (TODI), dianisidinediisocyanate (DADI), oligomers of the above isocyanates, for example, in the form of uretdiones, allophanates and oxadiazintes the form of adducts with short chain polyols, as well as any mixture of the above isocyanates and oligomers.

Preferred are MDI, TDI, HDI, and IPDI. Especially preferred are MDI and TDI.

Diisocyanate DI is preferably polyurethane P with isocyanate groups.

Suitable polyurethanes P with isocyanate groups contain two isocyanate groups and are the product of the interaction of at least one diol with at least one diisocyanate, in particular with at least one diisocyanate selected from the above-described monomeric diisocyanates. As a monomeric diisocyanate for this, in particular, an aromatic diisocyanate, in particular 2,4- or 2,6-toluene diisocyanate (TDI) or 4,4'-, 2,4'- or 2,2'-diphenylmethanediisocyanate ( MDI).

Diols suitable for conversion to polyurethane P with isocyanate groups are, in particular, polyether diols, polyester diols and polycarbonate diols, as well as mixtures of these diols.

Suitable polyether diols, also called polyoxyalkylenediols, are, in particular, those which are polymerization products of ethylene oxide, 1,2-propylene oxide, 1,2- or 2,3-butylene oxide, tetrahydrofuran or mixtures thereof, possibly polymerised using molecules initiators with two active hydrogen atoms, such as, for example, water, 1,2-ethanediol, 1,2- and 1,3-propanediol, neopentyl glycol, diethylene glycol, triethylene glycol, isomeric dipropylene glycols and tripropylene glycols, isomeric butanediols, pentanediols, hexane IOLs, heptanediols, octanediols, nonanediol, decanediols, undecanediol, 1,3- and 1,4-cyclohexanedimethanol, bisphenol A, hydrogenated bisphenol A, aniline and short chain polyether diols, and mixtures of the foregoing. They can be used as polyoxyalkylenediols which have a low degree of unsaturation (measured according to ASTM D-2849-69 and given in milliequivalents of unsaturation per gram of diol (mEq / g)) obtained, for example, using double metal cyanide complex catalysts (DMC catalysts) and polyoxyalkylenediols with a higher degree of unsaturation, obtained, for example, using anionic catalysts such as NaOH, KOH or alkali metal alkoxides.

Particularly suitable polyoxyalkylenediols are polyoxyethylene diols, as well as polyoxypropylenediols.

Particularly suitable are polyoxypropylenediols with a degree of unsaturation below 0.02 mEq / g and a molecular weight in the range from 1000 to 30000 g / mol, as well as polyoxypropylenediols with a molecular weight of from 400 to 8000 g / mol. By "molecular weight" in the proposed document is understood the average molecular weight M _n . In particular, polyoxypropylenediols with a degree of unsaturation below 0.02 mEq / g and a molecular weight in the range from 1000 to 12000 g / mol, in particular from 1000 to 8000 g / mol, are suitable. These polyether diols sold, e.g., under the trademark Acclaim ^® (firm) Bayer.

Similarly, the so-called "EO-terminal" (ethylene oxide-terminal) polyoxypropylenediols are suitable. The latter are special polyoxypropylene polyoxyethylene diols, which are obtained, for example, from pure polyoxypropylene diol after polypropoxylation by alkoxylation with ethylene oxide and (which) as a result contain primary hydroxyl groups.

Suitable polyester diols are polyesters carrying two hydroxyl groups, which are prepared in a manner known per se, in particular by polycondensation of hydroxycarboxylic acids or polycondensation of aliphatic and / or aromatic dicarboxylic acids with dihydric alcohols.

Particularly suitable are polyester diols derived from dihydric alcohols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, neopentyl glycol, 1,4-butanediol, 1,5-pentanediol, 3-methyl-1,5-hexanediol 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, 1,12-hydroxystearyl alcohol, 1,4-cyclohexanedimethanol, dimeric fatty acid diol (dimeric diol), neopentyl glycol ether hydroxypivalic acids, or mixtures of the above alcohols with organic dicarboxylic acids or their anhydrides or esters, such as, for example, succinic acid, glutaric acid, adipic acid, trimethyladipic acid, cork acid, azelaic acid, sebacic acid, dodecandicarboxylic acid, maleic acid, fumaric acid, dimeric fatty acid, phthalic acid, phthalic acid , isophthalic acid, terephthalic acid, dimethyl terephthalate, hexahydrophthalic acid, or mixtures of the above acids, as well as polyester diols from lactones, such as, for example, ε-caprolactone, and Tori, such as, for example, the above dihydric alcohols.

Particularly suitable polyester diols are those derived from adipic acid, adelaic acid, sebacic acid, dodecandicarboxylic acid, dimeric fatty acid, phthalic acid, isophthalic acid and terephthalic acid as dicarboxylic acid, ethylene glycol, diethylene glycol 1 4-butanediol, 1,6-hexanediol, dimeric fatty acid diol and 1,4-cyclohexanedimethanol as the dihydric alcohol. In particular, polyester diols derived from ε-caprolactone and one of the above dihydric alcohols as an initiator are also suitable.

Polyester diols have a molecular weight of from 1000 to 15000 g / mol, in particular from 1500 to 8000 g / mol, in particular from 1700 to 5500 g / mol.

In particular, liquid, amorphous, semi-crystalline and crystalline polyester diols are suitable. Especially suitable are liquid polyether diols at room temperature, as well as mixtures of amorphous and liquid polyester diols at room temperature.

Suitable polycarbonate diols are those which are available through polycondensation, for example, the abovementioned - applicable for the synthesis of polyether diols - dihydric alcohols with dialkyl carbonates such as dimethyl carbonate, diaryl carbonates such as diphenyl carbonate or phosgene.

Especially suitable are liquid at room temperature or amorphous polycarbonate diols.

Diols, which are block copolymers carrying two hydroxyl groups, are additionally suitable for conversion to polyurethanes P with isocyanate groups. which contain at least two different blocks with a simple polyester, complex polyester and / or polycarbonate structure of the type described above.

Preferred diols for conversion to isocyanate-group polyurethanes P are polyoxyalkylenediols, in particular polyoxyethylene diols, polyoxypropylene diols and polyoxypropylene polyoxyethylene diols.

The preparation of polyurethanes P with isocyanate groups is carried out by known methods either directly from diisocyanates and diols, or by stepwise addition methods, which are also known as chain extension reactions.

In one preferred embodiment, the polyurethane P with isocyanate groups is prepared by reacting at least one diisocyanate with at least one diol, the isocyanate groups being in stoichiometric excess with respect to hydroxyl groups. Advantageously, the ratio between the isocyanate and hydroxyl groups was from 1.3 to 2.5, in particular from 1.5 to 2.2.

The dialdimine of formula (I) preferably has a molecular weight of from 1,000 to 30,000 g / mol, in particular from 2,000 to 30,000 g / mol, preferably from 4,000 to 30,000 g / mol, most preferably from 6,000 to 20,000 g / mol.

The dialdimine of the formula (I) can be obtained by the following described method, which is an additional aspect of the invention.

The method comprises the step of reacting a diisocyanate DI with a diamine of formula (IV), in particular of formula (IV ′) or formula (IV ″) in the presence of water.

Residues R, A, R^one, R², R³ and R^fourand R⁵already described.

Moreover, this conversion is carried out so that the molar ratio [diisocyanate DI] / [dialdimine of the formula (IV) or (IV ') or (IV ")] has a value <1, in particular from 0.9 to 0.5, preferably from 0.8 to 0. Further, the amount of water is selected so that the molar ratio [water] / [diisocyanate DI] is ≥2, preferably ≥10.

In this case, the selected value of the molar ratio [diisocyanate DI] / [dialdimine of the formula (IV) or (IV ') or (IV ")] directly determines the average chain length, that is, the value of n in formula (I) and, thus, the average molecular weight of dialdimine of formula (I). The closer the ratio is to 1, the greater the chain elongation and the higher the average molecular weight of dialdimine of formula (I).

Advantageously, in preparing dialdimines of formula (I), diisocyanate DI is first mixed with dialdimine of formula (IV) or (IV ′) or (IV ″) and then water is added.

At this conversion, at least one ALD aldehyde of formula R-CHO was released.

Dialdimine of the formula (I) was used, in particular, in the form of an emulsion.

An additional aspect of the invention relates, therefore, to an emulsion containing aldimine.

The aldimine-containing emulsion includes

a) at least one dialdimine of the formula (I) as described above;

b) water and

c) if necessary, at least one surfactant.

It is also possible that the emulsion containing aldimine consists of a), b) and, if necessary, c).

Advantageously, the aldimine-containing emulsion includes at least one surfactant.

As a surfactant, natural and synthetic substances can be used, which in solutions reduce the surface tension of water or other liquids. As surfactants, also called wetting agents, can be used anionic, cationogenic, nonionic or ampholytic surfactants or mixtures thereof.

Examples of anionic surfactants are compounds containing carboxylate, sulfate, phosphate or sulfonate groups, such as, for example, fatty alcohol ether sulfates, fatty alcohol sulfates, soaps, alkyl sulfonates, olefin sulfonates, aryl sulfonates, arylalkyl sulfonates and alkyl sulfates.

Examples of cationic surfactants are quaternary ammonium or phosphonium compounds, such as, for example, tetraalkylammonium salts, dimethyldystearylammonium salts and N-alkylpyridinium salts, in particular their chlorides.

Nonionic surfactants, the so-called nio-surfactants, include, for example, alcohol ethoxylates, phenols, alkyl phenols, amines, fatty amines, fatty acid amides, polysiloxanes and fatty acid esters, as well as simple alkyl or alkyl phenyl polyglycol ethers, such as, for example, polyglycol ether of fatty alcohol or fatty acid amides, alkyl glycosides, sugar esters, sorbitol ester, polysorbates or trialkyl amine oxides, as well as poly (meth) acrylic acid esters and amides with polyalkylene glycols or amine polyols lkilenglikolyami, which on one hand can be terminated with alkyl groups.

Ampolytic or amphoteric surfactants include amphoteric electrolytes, so-called ampholytes, such as, for example, aminocarboxylic acids and betaines.

Surfactants of this kind are widely available.

Particularly suitable are anionic surfactants.

Advantageously, the aldimine-containing emulsion is prepared by mixing with stirring the dialdimine of formula (I), water, and also, if necessary, a surfactant.

It will be apparent to those skilled in the art that the aldimine-containing emulsion can be prepared in another way.

Although one skilled in the art knows that upon receipt of an emulsion, various parameters, such as temperature, mixing speed, and the type and geometry of the mixer, have an important influence on the quality of the emulsion, it is also noted that these parameters are not critical in the preparation of the aldimine-containing emulsion discussed here. So aldimine-containing emulsion of good quality was able to quickly and reproducibly be obtained with various mixing devices without the need for coordination of mixing parameters.

An additional advantage may be that the aldimine-containing emulsion includes additional components. In particular, co-emulsifiers, anti-foaming agents, stabilizers, biocides such as fungicides, bactericides or algaecides, adhesion promoters, a solvent, a plasticizer, catalysts, fillers and a rheological excipient, in particular a thickener and thixotropic, should be mentioned as additional components additive.

The aldimine-containing emulsion may or may not contain an organic solvent. If an organic solvent is used, it is preferred that it is not a VOC solvent (VOC = Volatile Organic Compound). However, there are many different definitions for “volatile organic compounds” or “VOC”. For example, according to EU-Richtline 2004 / 42EG, VOC is defined as an organic compound with a boiling point of at most 250 ° C. at a standard pressure of 101.3 kPa. According to Schweizer Verordnung uber die Lenkungsangabe, VOC volatile organic compounds are defined as organic compounds with a vapor elasticity of at least 0.1 mbar at 20 ° C or a boiling point of at most 240 ° C at 1013.25 mbar. In the proposed document, “volatile organic compounds” or “VOC” are considered organic compounds that have a boiling point of at most 250 ° C. at normal pressure (1013 mbar) or a vapor elasticity of at least 0.1 mbar at 20 ° C.

In particular, in the case of solvents that are not VOC, we are talking about esters of carboxylic acids.

The aldimine-containing emulsion is preferably free of N-alkylpyrrolidones. In particular, the aldimine-containing emulsion does not contain N-methylpyrrolidone (NMP).

As catalysts, tertiary amines, in particular trialkylamines, such as, for example, triethylamine, as well as derivatives of morpholine ether, such as dimorpholine diethyl ether, tetramethyldimorpholine diethyl ether, polyethylene glycoldimorpholine ether and the like, are particularly suitable.

Particularly advantageous is an alimin-containing emulsion, which, along with at least one dialdimine of the formula (I) and water, further comprises at least one surfactant, at least one filler, in particular chalk or pyrogenic silicic acid. Additionally, the aldimine-containing emulsion preferably contains at least one catalyst.

Advantageously, the aldimine-containing emulsion has a pasty consistency, that is, it does not spread itself.

The aldimine-containing emulsion is stable and can be packaged and stored. However, during storage of the aldimine-containing emulsion, care should be taken that the temperature does not fall below its freezing temperature, since otherwise there is a danger of emulsion destruction. A broken emulsion when used can cause serious damage.

The described aldimine-containing emulsion is widely applicable. In one preferred embodiment, the aldimine-containing emulsion was used as a curing component or as an accelerating component for an adhesive, sealant or coating material that contain polymers with isocyanate groups, in particular polyurethanes with isocyanate groups.

In an additional aspect, the present invention relates to two-component compositions, which consist of two components K1 and K2.

The first component, component K1, contains at least one polymer with isocyanate groups, in particular at least one polyurethane P with isocyanate groups, as described above, or consists of them.

The second component, component K2, contains dialdimine of formula (I) as described above, or an aldimine-containing emulsion as described above, or consists of them.

Component K1 advantageously contains at least one filler. The filler affects, for example, both the consistency of the uncured composition and the mechanical properties of the hardened composition. Suitable fillers are inorganic and organic fillers, for example, natural, ground or precipitated calcium carbonates, which, if necessary, are coated with fatty acids, in particular stearates, calcined kaolin, alumina, aluminum hydroxide, barite (BaSO ₄ , also called barite ), silicic acid, in particular highly dispersed silicic acid from pyrolysis processes, carbon black, in particular carbon black obtained in the industry (hereinafter referred to as "carbon black"), PVC powder or hollow balls. Preferred fillers are calcium carbonate, kaolin, pyrogenic silicic acid and carbon black. It may be useful to introduce a mixture of various excipients.

A suitable amount of filler is, for example, from 10 to 70 wt.%, Preferably from 20 to 60 wt.%, Based on the total weight of component K1.

Advantageously, component K1 further comprises at least one catalyst that accelerates the reaction of isocyanate groups and / or hydrolysis of the aldimine groups.

Catalysts that accelerate the interaction of isocyanate groups with water are metal compounds, for example zinc compounds, such as dibutylzinc diacetate, dibutylzinc dilaurate, dibutylzinc distearate, dibutylzinc diacetyl acetate, dioctylzinc dibutyl zinc dichloride, dibutyl zinc dibutyl zinc dichloride, such as lauryl stannoxane, bismuth compounds such as bismuth (III) octoate, bismuth (III) neodecanoate or bismuth (III) oxinate; as well as tertiary amines, for example, 2,2'-dimorpholino-diethyl ether and other derivatives of simple morpholinoethers.

Catalysts that accelerate the hydrolysis of aldimino groups are, in particular, acids or compounds hydrolyzable to acids, for example, organic carboxylic acids such as benzoic acid, salicylic acid or 2-nitrobenzoic acid, organic carboxylic acid anhydrides such as phthalic anhydride or hexahydrophthalic anhydride, silyl esters of organic carboxylic acids, organic sulfonic acids such as methanesulfonic acid, para-toluenesulfonic acid or 4-dodecylbenzenesulfonic acid, or others f organic or inorganic acids.

Combinations of these catalysts may also exist, in particular a mixture of acids and metal compounds, or metal compounds and tertiary amines, or acids and tertiary amines, or acids and metal compounds and tertiary amines.

A typical catalyst content is from 0.005 to 1 wt.% Based on the entire component K1, it is usually clear to the skilled person how much catalyst is appropriate in this case.

Advantageously, component K1 further comprises at least one plasticizer. Suitable plasticizers are, for example, organic carboxylic acid esters or their anhydrides, for example phthalates, such as dioctyl phthalate, diisononyl phthalate or diisodecyl phthalate, adipates, such as dioctyl adipate, azelainates or sebacinates; esters of organic phosphoric and sulfonic acids and polybutenes.

Additional possible components of component K1 are, inter alia, the following excipients and additives:

- solvents, in particular, solvents that are not VOC;

- fibers, for example, of polyethylene;

- pigments, for example, titanium dioxide or iron oxides;

- additional catalysts common in the chemistry of polyurethanes;

rheology modifiers, such as, for example, thickeners or thixotropic additives, for example, urea compounds, polyamide waxes, bentonites or pyrogenic silicic acid;

reactive diluents or binders, for example, oligomers or polymers of diisocyanates, such as MDI, PMDI, TDI, HDI, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3- or 1,4-diisocyanate, IPDI, perhydro-2, 4'- and -4,4'-diphenylmethanediisocyanates (H ₁₂ MDI), 1,3- and 1,4-teramethylxilylene diisocyanates, in particular, isocyanurates, carbodiimides, urethanimines, biurets, allophanates and iminooxadiazinedio diisocyanates, adducts of polyisocyanates , dihydrazide adipic acid and other dihydrazides, as well as blocked hardeners in the form of polyaldimines, polyketimines, oxazolidines or polyoxazolidines;

- drying agents, such as, for example, molecular sieves, calcium oxide, highly reactive isocyanates, such as paratosyl isocyanate, orthoformate, alkoxysilanes, such as tetraethoxysilane, organoalkoxysilanes, such as vinyltrimethoxysilane, and organoalkoxysilanes to the silane group contain a functional group;

an adhesion promoter, in particular organoalkoxysilanes, hereinafter referred to as "silanes", such as, for example, epoxysilanes, vinylsilanes, (meth) acrylsilanes, isocyanatosilanes, carbamatosilanes, S- (alkylcarbonyl) mercaptosilanes and aldiminosilanes, as well as oligos;

- stabilizers against (action) of heat, light and UV radiation;

- flame retardants;

- surfactants, such as, for example, wetting agents, spill aids, deaeration agents and anti-foaming agents;

- biocides, such as, for example, algicides, fungicides or agents that inhibit the growth of fungi;

as well as additional substances commonly used in one-component polyurethane compositions.

The advantages of the present invention are especially clearly visible in cases where the K1 component contains both fillers and polyaldimines as additional constituents.

Advantageously, all of the aforementioned constituent parts, which are included, if necessary, in component K1, in particular, filler, catalyst, and plasticizer, are selected so that the storage stability of component K1 does not deteriorate as a result of the introduction of such a component, which means that component K1 does not change or only slightly changes its properties, in particular, coating properties and curing properties. This leads to the absence of reactions, in particular, isocyanate groups, leading to the chemical curing of component K1, during storage on a noticeable scale. Therefore, in particular, it is important that the named components do not release during storage or do not contain or contain at most traces of water. It may be appropriate to physically or chemically dry the desired constituents before mixing them to component K1.

Component K1 was obtained and stored with exclusion of moisture. In a suitable packaging or room, which is stable in various climatic conditions, such as, for example, a barrel, vessel or cartouche, it exhibits exceptional storage stability. The definitions of "storage stability" and "storage stability" in connection with the content of the proposed document means the state of affairs in which the viscosity of the composition at a given temperature of application and at a suitable exposure in the considered period of time does not increase, or at most, to such an extent that the composition remains applicable in the manner specified.

Typically, component K1 is a wet curable, one-component polyurethane adhesive or sealant, which are widely commercially available. For example, this type of adhesives offered under the names Sikaflex ^® or Sika Tack ^® company Sika Schweiz AG.

Component K1 reacts on its own alone, that is, without component K2, with air moisture and, due to this, is cured. The indicated cure however (is) very slow; in addition, with this kind of curing, random bubble formation occurs. However, as a result of the described application of the second (aldimine-containing) component K2, curing is greatly accelerated and bubble formation is suppressed.

Component K2 may contain additional components, in particular those presented above for component K1, provided that these additional components are stable during storage with other components of component K2. Upon receipt, component K2 is placed in a suitable package or device, such as, for example, a barrel, vessel or cartouche, and it can be stored and transported in the package.

Packages of components K1 and K2 may also be related to each other. So, for example, components K1 and K2 can be poured into the chambers of one double cartridge. This, for example, can be the so-called coaxial cartouche or double cartouche. Packages of this kind, which contain components K1 and K2 in the chambers that are locally separated from each other, are advantageous because the two components during storage and transportation remain together inseparable or not lost and, therefore, for applying the two-component composition should not first be assembled or composed.

The two components K1 and K2 are mixed with each other before or during application of the two-component composition. Mixing can be carried out in any way or manner.

In particular, the mixing can be carried out continuously homogeneous or non-homogeneous. The mixing of the two components is preferably carried out with a static mixer or a dynamic mixer. The result is a mixed or partially mixed two-component composition.

Figures 1a through 1f show some examples of such mixtures. Figures 2a through 2f show examples of mixers with which these kinds of mixtures can be obtained.

In one embodiment, the mixing of both components K1 and K2 is carried out mainly homogeneously.

This can be achieved, in particular, by using dynamic mixers. But you can also achieve mostly homogeneous mixing using static mixers with many mixing elements.

As is known to those skilled in the art, the term “homogeneously mixed” in the context of pasty adhesives and sealants, as discussed herein, should not be understood absolutely. The term in normal use means precisely that the boundaries of the mixture are no longer visible to the eye, while they can still be quite (visible), for example, in an electron microscope. Based on the experimental data, it can be assumed that when using Sulzer Quadro® type static mixers (available from Sulzer Chemtech) with 18 or more elements of a static mixer, there is basically a homogeneous mixing of the two pasty components.

In a further embodiment, the mixing of both components K1 and K2 is generally inhomogeneous, for example, in the form of layerwise or jet mixing.

Layer-by-layer mixing can be achieved, in particular, by using static mixers, moreover, they have a limited number of elements of a static mixer. For this, for example, a metering adapter can be used, such as described in patent WO95 / 24556 A1, the entire contents of which are hereby included in the disclosure of the present invention, by which component K2 is mixed with component K1.

The number of elements of the static mixer is, in particular, from 6 to 16, preferably from 6 to 12.

Jet mixing is carried out in one embodiment in such a way that one or more branches of component K2 is coated with a shell of component K1. This can be achieved by a coating apparatus, such as described in patent EP 1728840 A1. The entire contents of this document is included in the disclosure of the invention. In another embodiment, the branch of components K1 and K2 mixed with each other is coated with a shell of component K1. This option has the advantage that in the core of the roller, which is called where the components K1 and K2 are mixed, rapid curing occurs, while the surface of the roller hardens mainly due to air moisture, since there is no K2 component there. This leads to the fact that the open period (limited by the formation of a film) of this kind of roller is longer compared to the same period of the roller, which consists of mixed components K1 and K2 in the whole diameter, so that the advantage of a longer open period is combined with fast curing. The possibility of achieving this kind of shell coating is provided by the static mixer proposed in patent WO 02/32562 A1, the entire contents of which are included in the disclosure of the invention.

It has been shown, especially in the case of wet-hardening polyurethane adhesives with a high modulus of elasticity as a component K1 - primarily those that contain polyaldimine - that the composition obtained after inhomogeneous mixing of component K2 has an extremely good processing ability, as well as high final strength. This is a difference from compositions that are used in a similar application of the K2 components of the state of the art, especially K2 components containing N-alkylpyrrolidone. In these cases, often after a short time after mixing component K2, the processing ability is insufficient, which, for example, is revealed by the fact that the composition has a noticeable scraping of a granular appearance. Further, the final strength of the cured composition remains limited. Perhaps this boils down to insufficient bonding of the components containing the K2 component to the polyurethane matrix, which leads to the fact that the cured composition cracks under a force load inside the previous layers of the K2 component.

The described two-component composition can be used as an adhesive, sealant or coating or lining.

When used as an adhesive, a two-component composition is used for bonding a substrate S1 and a substrate S2. Bonding is preferably carried out in the following manner.

The specified method for bonding substrates S1 and S2 includes the steps of:

i) applying the above two-component composition during mixing or after mixing the two components K1 and K2 on the substrate S1;

ii) contacting the applied composition with the substrate S2;

or

i ') applying the above two-component composition during mixing or after mixing the two components K1 and K2 on the substrate S1;

ii ') applying the above two-component composition during mixing or after mixing the two components K1 and K2 on the substrate S2;

iii ') contacting the composition deposited on the substrate S1 with the composition deposited on the substrate S2.

Moreover, the substrates S1 and S2 are the same or different from each other.

When used as a sealant, a two-component composition is used for sealing substrates. Sealing is mainly carried out according to the following method.

The specified method of sealing includes a stage

i ") applying the above two-component composition during mixing or after mixing the two components K1 and K2 between the substrate S1 and the substrate S2.

Moreover, the substrates S1 and S2 are the same or different from each other.

When used as a sealant, the composition is used as a sealant between two substrates S1 and S2. Typically, the seal is pressed at the junction.

The coating is preferably carried out according to the following method.

The specified method of obtaining a coating includes a stage

i '' ') applying the above two-component composition during mixing or after mixing the two components K1 and K2 on the substrate S1.

In these three methods, the mixing of the two components K1 and K2 in one of the embodiments is carried out mainly homogeneously. In another embodiment, the mixing of the two components K1 and K2 is carried out mainly inhomogeneous. In particular, inhomogeneous mixing is carried out in such a way that a layered, jet or spiral pattern of the mixture is formed.

If necessary, steps ii), iii ′), i ″) or I ″ ″) can be completed with a moisture curing step.

Suitable substrates S1 or S2 are, for example, inorganic substrates such as glass, glass ceramics, concrete, mortar, baked brick, brick, gypsum and natural stone such as granite or marble; metals or alloys such as aluminum, steel, non-ferrous metals, galvanized metals; organic substrates such as wood; polymers such as PVC, polycarbonates, PMMA, polyesters, epoxies; coated substrates, such as metals or powder coated alloys; as well as paints and varnishes. Preferably, the substrate S1 and / or S2 is selected from the group consisting of concrete, cement, mortar, baked brick, brick, gypsum, natural stone, asphalt, metal, metal alloy, wood, ceramic, glass, polymer, powder coating, paint, and varnish.

If necessary, the substrates can be pretreated before applying the two-component composition. Such pretreatments include, in particular, physical and / or chemical cleaning methods, for example, grinding, sandblasting, brushing or the like, or treatment with cleaning agents or solvents or applying an adhesion promoter, a solution of an adhesion promoter or a primer.

Particularly preferred is the use of a vitrification method for disks in vehicles, in particular in automobiles.

As a result of one of the described methods of bonding, or sealing, or coating receive the product.

The product may be a building or structure of ground construction or underground construction, an industrially manufactured product or consumer product, in particular a window, a household machine or a vehicle, in particular a rolling stock unit, or a part of a vehicle.

The described two-component composition has great advantages, on the one hand, providing excellent early strength and high final strength and, on the other hand, composing it without VOC solvents, in particular, without N-alkylpyrrolidones, so that it meets high standards in relation to ecological and working hygienic properties.

Brief Description of the Drawings

Further, selected embodiments of the invention are better clarified with the help of the drawings. In different figures, the same elements are provided with the same standard notation. The direction of the forces or movement is indicated by arrows.

Show:

FIG. 1a-d is a schematic transverse image of a triangular roller 1 across the direction of the roller;

figa - image of the jet mixture with one branch K2;

fig.1b - image of the jet mixture with several branches K2;

figs - image of the jet mixture from the branch K1 / K2 with a shell of K1;

fig.1d - image of a layered mixture;

FIG. 1e-f is a schematic transverse view of a triangular roller 1 in the direction of the roller;

fige - image of the jet mixture with one branch K2;

fig.1f - image of a spiral mixture with one branch K2;

FIG. 2a-f is a schematic transverse image along the longitudinal axis z through a mixing device;

FIG. 2a is a mixing device leading to the kind of mixture shown in FIG. 1a);

FIG. 2b is a mixing device leading to the kind of mixture shown in FIG. 1b);

FIG. 2c is a mixing device leading to the kind of mixture shown in FIG. 1c);

FIG. 2d is a mixing device leading to the kind of mixture shown in FIG. 1d);

FIG. 2f is a mixing device leading to the kind of mixture shown in FIG. 1f);

FIG. 2f '- part of the tip 14.

Only the basic elements for a direct understanding of the invention are shown. For example, collections and parts for supplying components K1 and K2 are not presented.

Figure 1a is a schematic cross-sectional view of a triangular roller 1 across the direction of the roller after partial mixing of the components K1 and K2 of a two-component composition that was applied to the substrate S1. In this example, partial mixing was carried out in such a way that a jet mixing pattern appeared, in which one branch of component K2 was covered with a shell of component K1.

A mixing pattern of this kind can be achieved, for example, using a mixing device, which is schematically shown in figure 2A.

Figure 1b is a schematic cross-sectional view of a triangular roller 1 across the direction of the roller after partial mixing of the components K1 and K2 of the two-component composition that was applied to the substrate S1. In this example, partial mixing was carried out in such a way that a jet mixing pattern appeared, in which several branches of component K2 were covered with a shell of component K1.

A mixing pattern of this kind can be achieved, for example, using a mixing device, which is schematically shown in figure 2b.

Figure 1c is a schematic cross-sectional view of a triangular roller 1 across the direction of the roller after partial mixing of components K1 and K2 of a two-component composition that was applied to the substrate S1. In this example, partial mixing was carried out in which the mixing region 2, in which the components K1 and K2 are fully or partially mixed with each other, is coated with an unmixed component K1. In the indicated embodiment, the mixing in the mixing region 2 is layered.

A mixing pattern of this kind can be achieved, for example, using a mixing device, which is schematically shown in figure 2C.

Figure 1d is a schematic cross-sectional view of a triangular roller 1 across the direction of the roller after partial mixing of the components K1 and K2 of a two-component composition that was applied to the substrate S1. In this example, partial mixing was carried out in layers.

A mixing pattern of this kind can be achieved, for example, using a mixing device, which is schematically shown in figure 2d.

Figure 1e is a schematic cross-sectional view of a triangular roller 1 in the direction of the roller after partial mixing of the components K1 and K2 of a two-component composition that was applied to the substrate S1. In this example, partial mixing was carried out in the form of a branch K2, which is covered by a shell K1 and which is oriented linearly with the roller in such a way that a pattern of jet mixing occurs.

A mixing pattern of this kind can be achieved, for example, using a mixing device, which is schematically shown in figure 2A.

Figure 1f is a schematic cross-sectional view of a triangular roller 1 in the direction of the roller after partial mixing of the components K1 and K2 of the two-component composition that was applied to the substrate S1. In this example, partial mixing was carried out in the form of a branch K2, which is covered by a shell K1 and which is oriented in a spiral in the glue roller so that a spiral mixing pattern appears.

A mixing pattern of this kind can be achieved, for example, using a mixing device, which is schematically shown in figure 2f.

Figure 2a schematically shows a cross section along the longitudinal axis z of the mixing device 3, which leads to a jet mixing pattern, as shown in figure 1a. The mixing device 3 has a supply line 4 for the component K1, which limits the tubular inner space 9 into which the component K1 enters. Into said interior space 9, a supply line 6 for component K2 is included. When applying or mixing, component K1 is supplied under pressure through the supply line 4 and component K2 through the supply line 6. After passing the outlet 8 of the supply line for component K2, the two components K1 and K2 contact each other in the flow direction, and the two components partially mix . When leaving the outlet 7 of the mixing device, there is a jet mixing pattern in which the component K2 is covered by the shell of the component K1.

Figure 2b schematically shows a cross section along the longitudinal axis z of the mixing device 3 ', which leads to a jet mixing pattern, as shown in figure 1b. The mixing device 3 'is a variant of the mixing device 3, which is discussed above in figure 2A. In the indicated embodiment, the supply line 6 for component K2 entering the interior space 9 has several outlet openings 8 of the supply line 6. When leaving the outlet 7 of the mixing device, a mixing pattern is obtained, as shown in figure 1b, in which several branches of component K2 are covered shells of component K1.

Figure 2c schematically shows a cross section along the longitudinal axis z of the mixing device 3 ", which leads to a mixing pattern, as shown in figure 1c. The mixing device 3" has a feed line 4 for component K1, which delimits the tubular interior space 9, which enters component K1. Into said interior space 9, a supply line 6 for component K2 is included. When applying or mixing, component K1 is supplied under pressure through the supply line 4 and component K2 through the supply line 6. After passing the outlet 8 of the supply line for component K2, the two components K1 and K2 are in contact with each other in the flow direction and mixed with each other by several mixing elements 11 of the static mixer, which are located in the static mixer 10. From each mixing element 11 of the static mixer there was a layer of flow of the mixture and after leaving the outlet 12 of the static About the mixer in the mixing area 2, a layered mixing pattern arose. Due to the fact that the static mixer 10 is located centrally in the feed line for component K1, a part of component K1 flows like a shell over the static mixer and, after the outlet 12 of the static mixer 10 flows downstream through the static mixer, covers the mixed branch 2 of components K1 and K2. When leaving the outlet 7 of the mixing device, a mixing pattern appears, as shown in FIG. 1c.

Figure 2d schematically shows a cross section along the longitudinal axis z of the mixing device 3 ″, which leads to a jet mixing pattern, as shown in figure 1d. The mixing device 3 ″ ″ is a variant of the mixing device 3 ″, which is discussed in connection with figure 2c. In contrast to the embodiment in figure 2c, the total flow of component K1 with component K2 is mixed through several static elements 11. As a result, upon exiting the mixing device’s outlet 7 produces a mixing pattern as shown in figure 1d, a similar result is also achieved if a static mix is placed at the outlet 7 of the mixing device 3, as shown in figure 2a s, corresponding to the state of the art.

Figure 2f schematically shows a cross section along the longitudinal axis z of the mixing device 3 ″ ″, which leads to a mixing pattern, as shown in figure 1a or figure 1f. The mixing device 3 ″ ″ has a supply line 4 for component K1, which limits the tubular interior space 9 into which component K1 enters. Into said interior space 9 of width d _B includes a feed line 6 for component K2. In such an embodiment, said rotatable feed line acts as part of a rotary member 13 of width d _T. The feed line ends laterally with the rotational element 13. In the embodiment shown here, a tip 14 is shown, which is shown in detail in figure 2f ', which is the end of the feed line 6 of component K2. The tip 14 has a drilled hole 15, which connects the feed line with the outlet 8. The tip through the thread 16 is connected to the rest of the feed line 6 and is fixed by a latch 17. Due to the rotation of the rotational element 13 and, thus, the feed line 6, the outlet 8 in the inner space 9 describes a circular motion. When applying or mixing, components K1 and K2 are simultaneously unloaded and a spiral branch is formed from component K2 covered by component K1. As a result, when the mixing device exits the outlet 7 of the mixing device, a mixing pattern is formed, as shown in figure 1a or figure 1f.

It will be apparent to those skilled in the art that the embodiments described herein are illustrative only and should in no way be construed as limiting. It goes without saying that various options are possible. In particular, the mixing of the two components can be optimized by using a larger number of mixing elements 11 of the static mixer or by using dynamic mixing elements or dynamic mixers, and quasi-homogeneous or homogeneous mixtures of both components can be obtained.

List of digital notation

1 - roller

2 - mixing area

3, 3 ', 3 ", 3' '', 3 '' '' '- mixing device

4 - the outer wall of the mixer

5 - the internal space of the feed line component K2

6 - feed line component K2

7 - outlet of the mixing device

8 - outlet of the supply line of component K2

9 - the internal space of the feed line component K1

10 - static mixer

11 - element of a static mixer

12 - outlet of the static mixer

13 - rotation element

14 - tip of the flow line of component K2

15 - drilled hole through the tip 14

16 - thread in the tip 14

17 - clamp

EXAMPLES

Description of measurement methods

Infrared spectra were measured on a FT-IR 1600 Perkin-Elmer device (horizontal unit with ZnSe crystal). Samples were applied undiluted as a film. Absorption lines are given in wave numbers (cm ^-1 ) (measurement window: 4000-650 cm ^-1 ).

The amine content in the obtained dialdimines, which means the content of protected amino groups in the form of aldimino groups, was determined titrimetrically (with 0.1 N HClO ₄ in glacial acetic acid on a crystal violet) and given in mmol N / g.

a) Obtaining dialdimines of the formula (IV)

Polyaldimine A1

55.0 g (0.19 mol) of distilled 2,2-dimethyl-3-lauroloxypropanal were placed in a round bottom flask under nitrogen atmosphere. With vigorous stirring, 13.7 g (0.18 mol N) of 3,6-dioxaoctane-1,8-diamine (Jeffamine ^® XTJ-504, Huntsman; amine content 13.34 mmol N / g) was slowly added from the dropping funnel, moreover, the mixture was heated. Then the volatiles were removed in vacuo (10 mbar, 80 ° C). Yield: 65.1 g of a clear, colorless oil with an amine content of 2.81 mmol N / g. IR: 2954, 2920, 2852, 1736 (C = O), 1668 (C = N), 1466, 1419, 1394, 1373, 1366, 1351, 1340sh, 1282sh, 1248, 1232, 1156, 1114, 1057, 1020, 998, 932, 917sh, 876sh, 837, 791, 767, 722.

Dialdimin A2

74.3 g (0.26 mol) of distilled 2,2-dimethyl-3-lauroloxypropanal were placed in a round bottom flask under a nitrogen atmosphere. With vigorous stirring, 30.0 g (0.25 mol N) of polyether diamine (polyoxypropylene diamine with an average molecular weight of about 240 g / mol; Jeffamine ^® D-230, Huntsman; amine content of 8.32 mmol N / g was slowly added from a dropping funnel ), the mixture being heated and cloudy. Then the volatiles were removed in vacuo (10 mbar, 80 ° C). Yield: 99.3 g of a clear, colorless oil with an amine content of 2.53 mmol N / g.

b) Obtaining polyurethane emulsions

Emulsion E1

An emulsion containing dialdimine of the formula (I) with an average molecular weight of about 11,000 was prepared as follows. In a vacuum mixer, 72.7 g of polyurethane P1, the preparation of which is described below, 17.3 g of dialdimine A1, 0.3 g of a solution of salicylic acid (5 wt.% In dioctyl adipate) and 90.0 g of polyethylene glycol dibutyl ether ( Polyglycol BB 300, Clariant; average molecular weight 300) and heated to 60 ° C. 76.2 g of water was added and the mixture was stirred at 60 ° C for 20 minutes. A milky white fluid emulsion was obtained with a water content of 29.5 wt.%.

Polyurethane P1 was prepared as follows.

4000 g of polyoxypropylenediol (Acclaim ^® 4200 N, Bayer; OH number 28.5 mg KOH / g) and 520 g of 4,4'-methylenediphenyldiisocyanate (MDI; Desmodur ^® 44 MC L, Bayer) at 80 ° C were converted to polyurethane with terminal isocyanate groups with the content of free isocyanate groups (determined titrimetrically) of 1.86 wt. %

Emulsion E2

An emulsion of an organic polymer with ionic groups and an average molecular weight of about 20,000 was obtained in a known manner by polyaddition of isophorone diisocyanate (IPDI; Vestanat ^® , IPDI, Degussa) with Caradol ^® ED56-11 polyol (Shell), aminoethylethanolamine and 2,2-bis (hydroxymethyl) propionic acid in N-methylpyrrolidone (NMP), followed by neutralization with triethylamine and the addition of water to a content of 29.5 wt.%. Received milk emulsion.

Emulsion E3

They tried to obtain an emulsion similar to E2 emulsion, but without NMP, containing an organic polymer with ionic groups, moreover, in the process described for E2 emulsion, replace N-methylpyrrolidone with diethylene glycol dimethyl ether (Clariant), which is a regular NMP substitute. However, with the addition of aminoethylethanolamine, the polymer solidified and failed to emulsify.

c) Obtaining accelerators K2

Accelerator BK1

85 g of E1 emulsion were placed in a vacuum mixer and mixed with 1 g of technical sodium dodecylbenzenesulfonate (Rhodacal ^® DS-10, Rhodia), 1 g of sodium tallate (Dresinate ^® TX, Eastman), 0.5 g of triethylamine, 7.5 g of dibutyl ether polyethylene glycol (Polyglycol BB 300, Clariant; weight average molecular weight 300), 5 g of a hydrophilic pyrogenic silica (Aerosil ^® 200, Degussa) and 5 g of hydrophobic pyrogenic silicic acid (Aerosil ^® R972, Degussa) to form a thin creamy paste.

Accelerator VK2

85 g of emulsion E2 were placed in a vacuum mixer and mixed with 10 g of hydrophilic pyrogenic silicic acid (Aerosil^® 200, Degussa) and 5 g of chalk (Omya^® 5 GU, Omya) to form a thin creamy paste.

Accelerator VK3

83.5 g of dialdimine A2, 6.2 g of water, 10 g of hydrophilic pyrogenic silicic acid (Aerosil ^® 200, Degussa) and 0.3 g of a solution of salicylic acid (5 wt.% In dioctyl adipate) were mixed in a vacuum mixer to form homogeneous paste.

d) Obtaining a one-component polyurethane composition (corresponding to component K1)

Composition Z1

In a vacuum mixer, 180 g of P2 polyurethane, which is described below, 97 g of diisodecyl phthalate (DIDP; Palatinol ^® Z, BASF), 18 g of hydrophobic pyrogenic silicic acid (Aerosil ^® R972, Degussa), 54 g of carbon black, 90 g of calcined kaolin, 1.3 g of 3-glycidoxypropyltrimethoxysilane (Silquest ^® A-187, GE Advanced Materials), 0.9 g of Desmodur ^® CD (Bayer) and 9 g of a solution of 10 wt.% of 2,2'-dimorpholindiethyl ether ( DABCO ^® DMDEE Catalyst, Air Products), and 2 wt.% in DIDP dibutyl zinc dilaurate to form a homogeneous paste, the mixture was poured into internally lacquered aluminum cartouche and tightly closed Is it the absence of air. The composition had an isocyanate group content of 0.20 mmol NCO / g and a density of 1.26 g / cm ³ .

Polyurethane P2 was prepared as follows.

1300 g of polyoxypropylene diol (Acclaim ^® 4200 N, Bayer; OH number of 28.5 mg KOH / g), 2600 g of polyoxypropylene polyoxyethylene triol (Caradol ^® MD34-02, Shell; OH number of 35.0 mg KOH / g), 600 g 4 , 4'-methylenediphenyldiisocyanate (MDI; Desmodur ^® 44 MC L, Bayer) and 500 g of diisodecyl phthalate (DIDP; Palatinol ^® Z, BASF) at 80 ° C were converted to isocyanate-terminated polyurethane with 2.05 wt.% Free isocyanate groups. %

f) Obtaining and testing two-component polyurethane adhesives (consisting of components K1 and K2).

Example 1 and comparative examples 2 and 3

For each example, the corresponding components K1 and K2 were mainly homogeneously mixed in the volume ratios given in Table 1 and their curing properties were tested.

The mixing of both components K1 and K2 was carried out continuously during application, in which the polyurethane adhesive was applied with a two-component spray gun with a static mixer type Sulzer Quadro ^® (available from Sulzer Chemtech) with 24 mixing elements.

To study the curing properties, a two-component polyurethane adhesive was tested, on the one hand, for the curing speed and, on the other hand, for the ability to cut after application.

To test curing rate was measured tensile strength and shear the following method: for each measurement were prepared by two glass plates 6 mm thick, 25 mm wide and 75 mm long (Floatglas; firm Rocholl, Schönbrunn, Germany) from Sika ^® activator (available from Sika Schweiz AG). After blowing with air for 10 minutes, the plates were placed in a vertical position 4 mm apart from each other using a suitable PTFE mold so that they overlap 12 mm at the head parts. The overlap area between the plates was filled with glue, the latter being placed on the activated sides of the plates. In this way, the plates glued to each other were left to lie at 23 ° C and 50% relative humidity; after 2 or 4 or 24 hours, using a tensile testing machine, at a constant speed of the transverse beam of 20 mm / min, they were pulled apart from each other with a force of DIN EN 1465 until failure and the tensile strength was measured in MPa (N / mm ² ). The values shown are average values from three measurements.

To determine the ability to be cut, an adhesive in the form of a triangular roller with a main surface of about 1 cm was applied to an LDPE film, the film was left at 23 ° C and 50% relative humidity for 2 hours, and then cut with a knife in the longitudinal direction. Then, the adhesive was evaluated as being cut if the knife blade remained unpolluted during cutting of the roller, which meant that the adhesive was so bound that when cutting did not leave any unbound material.

The results of the tests are shown in table 1.

Table 1 Example one 2 (comparative) 3 (comparative) Component K1 Z1 Z1 Z1 Component K2 Bk1 Bk2 Bk3 Volumetric ratio K1 / K2 98/2 98/2 95/5 Early strength after 2 hours (MPa) > 5 > 5 0.3 Early strength after 4 hours (MPa) > 5 > 5 0.9 Early strength after 24 hours (MPa) > 5 > 5 3.6 Cutting ability after 2 hours Yes Yes (yes) ^a NMP content No Yes No Table 1: Composition of two-component polyurethane adhesives of example 1 and comparative examples 2 and 3.
^but very soft

Example 4 and comparative examples 5 and 6

For each example, the corresponding components K1 and K2 were basically mixed in layers in the volume ratios given in Table 2 and their curing properties were tested.

The mixing of both components K1 and K2 was carried out continuously during application, in which the polyurethane adhesive was applied with a two-component spray gun with a static mixer with 10 mixing elements (type TAN-510, GLT, Germany).

To study the curing properties, a two-component polyurethane adhesive was tested, on the one hand, for strength in the early period and, on the other hand, for the ability to cut after application, as described in example 1. The results of the tests are presented in table 2.

table 2 Example four 5 (comparative) 6 (comparative) Component K1 Z1 Z1 Z1 Component K2 Bk1 Bk2 Bk3 Volumetric ratio K1 / K2 98/2 98/2 95/5 Early strength after 2 hours (MPa) 1,6 > 5 not from. ^but Early strength after 4 hours (MPa) 1.9 > 5 0.7 Early strength after 24 hours (MPa) 2.7 > 5 2.0 Cutting ability after 2 hours Yes Yes No NMP content No Yes No Table 2: Composition of two-component polyurethane adhesives of example 4 and comparative examples 5 and 6.
^not measured

Comparison of the proposed example 1 with comparative example 2, which is based on the VK2-containing NMP accelerator, which corresponds to the state of the art, shows that, when the mixture is mostly homogeneous, excellent strength was obtained in the early period. The VK2 accelerator, corresponding to an NMP-free accelerator, cannot be obtained, since gelation already occurs upon receipt of the corresponding E3 emulsion (as described above).

Further, the results from tables 1 and 2 show that the proposed examples 1 and 4, in contrast to comparative examples 3 and 6, which are based on the VK3 accelerator, which corresponds to the current state of the art, exhibit much improved early strength and better ability to cut.

Claims (22)

1. Dialdimine of the formula (I)

where R represents a radical of the formula (II)

where R ¹ and R ² are either independently monovalent hydrocarbon radicals with from 1 to 6 C atoms;
R ³ represents a hydrogen atom;
R ⁴ represents a radical of formula (III ')

where R ⁵ represents a linear or branched alkyl radical with from 1 to 12 C-atoms,
A is a C ₄ -C ₁₀ diamine DA group with two primary aliphatic amino groups after the removal of both primary aliphatic amino groups and containing two ether groups,
Q represents a group of diisocyanate DI after removal of both isocyanate groups;
n is 0 or an integer from 1 to 15; and
moreover, A and R do not contain groups which, in the absence of water, are capable of reacting with isocyanate groups. 2. Dialdimine according to claim 1, characterized in that the radicals A and R do not contain hydroxy groups, secondary amino groups, mercapto groups and other groups with active hydrogen. 3. Dialdimine according to claim 1, characterized in that the diisocyanate DI is a polyurethane P with isocyanate groups. 4. Dialdimine according to claim 1, characterized in that the polyurethane R with isocyanate groups is obtained by reacting at least one diol with at least one monomeric diisocyanate. 5. Dialdimine according to claim 4, characterized in that the monomeric diisocyanate is an aromatic diisocyanate, in particular 2,4- or 2,6-toluene diisocyanate (TDI) or 4,4'-, 2,4'- or 2,2 'diphenylmethanediisocyanate (MDI). 6. Dialdimine according to claim 4, characterized in that the diol is a polyoxyalkylene diol, in particular polyoxyethylene diol, polyoxypropylene diol or polyoxypropylene polyoxyethylene diol. 7. Dialdimine according to any one of claims 1 to 6, characterized in that the dialdimine of formula (I) has a molecular weight of from 1000 to 30,000 g / mol, in particular from 2,000 to 30,000 g / mol, preferably from 4,000 to 30,000, most preferably from 6000 to 20,000 g / mol. 8. Dialdimine according to claim 1, characterized in that the diamine DA is selected from the group consisting of, 3,6-dioxaoctane-1,8-diamine, 4,7-dioxadecane-1,10-diamine, 4,7-dioxadecane -2,9-diamine, 4,9-dioxadodecane-1,12-diamine, 5,8-dioxadodecane-3,10-diamine. 9. A method of producing a dialdimine of formula (I) according to any one of claims 1 to 8, comprising the step of reacting a diisocyanate DI with a dialdimine of formula (IV) in the presence of water

where the diisocyanate DI and dialdimine of the formula (IV) are used in the molar ratio [diisocyanate DI] [dialdimine of the formula (IV)] <1, and the amount of water is chosen so that the molar ratio [water] / [diisocyanate DI] is> 2. 10. The method according to claim 9, characterized in that the molar ratio of diisocyanate DI] [dialdimine of formula (IV)] is from 0.9 to 0.5, preferably from 0.8 to 0.5. 11. The method according to claim 9, characterized in that the molar ratio [water] / [diisocyanate DI] is> 10. 12. The aldimine-containing emulsion used as a curing or accelerating component for polymers with isocyanate groups, containing
a) at least one dialdimine of the formula (I) according to one of claims 1 to 8;
b) water and
c) optionally at least one surfactant. 13. The aldimine-containing emulsion according to claim 12, characterized in that the emulsion is free of organic VOC solvents, in particular N-alkylpyrrolidones. 14. The use of the aldimine-containing emulsion according to claim 12 or 13 as a curing component or accelerator for glue, a sealant or a coating substance that contain a polymer with isocyanate groups. 15. A two-component composition for glue, sealing, coating or layer, consisting of two components K1 and K2, where
component K1 contains or consists of at least one polymer with isocyanate groups, in particular at least one polyurethane with isocyanate groups;
and
component K2 contains or consists of dialdimine of the formula (I) according to one of claims 1 to 8 or the aldimine-containing emulsion according to claim 12 or 13. 16. The use of the two-component composition according to item 15 as an adhesive, sealant or coating or lining. 17. A method for bonding substrates S1 and S2, comprising the steps of:
i) applying the two-component composition according to claim 15 during mixing or after mixing the two components K1 and K2 on the substrate S1;
ii) contacting the applied composition with the substrate S2
or
i ') applying the two-component composition according to clause 15 during mixing or after mixing the two components K1 and K2 on the substrate S1;
ii ') applying the two-component composition according to claim 15 during mixing or after mixing the two components K1 and K2 on the substrate S2;
iii ') contacting the composition applied to the substrate S1 with the composition applied to the substrate S2;
moreover, the substrates S1 and S2 are the same or different from each other. 18. The method according to 17, characterized in that the mixing of the two components K1 and K2 is carried out mainly homogeneously. 19. The method of compaction, including stage
i '') applying the two-component composition according to clause 15 during mixing or after mixing the two components K1 and K2 on the substrate S1 and the substrate S2,
moreover, the substrates S1 and S2 are the same or different from each other. 20. The method according to claim 19, characterized in that the mixing of the two components K1 and K2 is carried out mainly homogeneously. 21. A method for producing a coating, in particular a floor covering, comprising the step of
i ''') applying the two-component composition according to claim 15 during mixing or after mixing the two components K1 and K2 onto the substrate S1. 22. The method according to item 21, wherein the mixing of the two components K1 and K2 is carried out mainly homogeneously.

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