WO2010066686A2

WO2010066686A2 - Novel triazine polymers, method for the production and use thereof

Info

Publication number: WO2010066686A2
Application number: PCT/EP2009/066543
Authority: WO
Inventors: Martin Burger; René Dicke; Andreas Endesfelder; Christoph Hahn
Original assignee: Borealis Agrolinz Melamine Gmbh
Priority date: 2008-12-09
Filing date: 2009-12-07
Publication date: 2010-06-17
Also published as: WO2010066686A3; DE102008061137A1

Abstract

The present invention relates to novel aldehyde-free triazine polymers of general formula (I) or mixtures thereof, and to a method for the production and use thereof.

Description

Novel triazine polymers, process for their preparation and their use

The present invention relates to triazine polymers according to claim 1, a process for their preparation according to claim 15 and their use according to claim 16.

The most well-known triazine-containing polymers are aminoplasts such as melamine-formaldehyde resins or melamine-urea-formaldehyde resins [Ullmanns Encyclopedia of Industrial Chemistry (1987), Vol. A2, 130-131]. These are mainly used in the woodworking industry. A disadvantage of these compounds is the use of formaldehyde, which has a high toxic potential.

For this reason, numerous attempts have been made to replace formaldehyde with other aldehydes. Thus, WO 03/101973 and WO 04/085506 describe the use of glyoxylic acid derivatives for polymer production. US 1654215 and DE 918780 describe the use of acrolein. In all cases, however, the synthesized polymers had less favorable properties than the aminotriazine-formaldehyde resins.

Triazine-containing polymers, which are prepared without the use of aldehydes, are so far only rarely found in the literature.

From DE2121 184 melamine derivatives are removable which carry an ester group on the amino nitrogen in a side group and which can be used for the production of polyesters. However, the preparation of these melamine derivatives is very expensive. In addition, the properties of the polymers prepared from the thus modified melamine derivatives are not shown.

WO96 / 28490 relates to the use of alkyl- and hydroxyalkyl-modified melamine derivatives in epoxy resins, the melamine derivatives being incorporated into the polymer network in the form of crosslinkers. The epoxy compositions thus prepared are characterized by a high chemical and thermal resistance.

US Pat. No. 3,145,523 describes triazine derivatives which contain double bonds and hydroxyl groups. These modified triazine derivatives are polymerized alone or in the presence of acrylonitrile or ethylenic compounds. The triazine derivatives can be prepared, for example, by reacting the triazine with ethylenic acids or their anhydrides, such as, for example, maleic acid. The aim of the invention was now the provision of novel triazine polymers without the use of formaldehyde or other aldehydes and a process for their preparation and their uses.

This object is achieved by triazine polymers having the features of claim 1.

Thereafter, the triazine polymers according to the invention by the general formula I.

(I)

or mixtures thereof, wherein

A ¹ and A ² independently of one another denote O, NH or NR ¹⁴

R ¹ = a linear or branched Ci-C ₂ oo-alkyl, a cyclic substituent in the form of a C ₅ - C ₂ o-cycloalkyl, a C ₂ -C ₂ -alkenyl, C ₂ -C ₂ alkynyl, a C ₅ -C _2oo aryl, a Ci-C ₂₀₀ - alkyl-substituted C ₅ -C _2O o-aryl, C ₂ -C ₂₀ -alkenylsubstituiertes C ₅ -C _2O o-aryl, C ₂ -C ₅₀ - heterocycle, a Ci-C _2O o-alkyl-substituted C ₂ -C ₅₀ heterocycle, a C ₂ -C ₂₀ - alkenyl-C ₂ -C ₅₀ -heterocycle, where the radicals, by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted nitrogen atoms by double bonds, siloxane groups and / or by one or more groups of the type -C (O) O-, -OC (O) -, -C (O) -, -NHC (O) O-, -OC (O) NH - and / or -OC (O) O-, and / or one or more functional groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups, carboxylic acid ester groups, Carboxylic acid amide groups, carbonate groups, halogens, epoxy groups, trialkoxy-silane groups, sulfonic acid groups and carbamate groups,

or a group selected from the formulas (II) to (IV)

and wherein the molar mass of the radical R ^{1 is} between 200 and 8000 g / mol, and where the radical R ¹ in the polymer may be identical or different,

R 1 = -H, Q ¹ , -CO-A-R -A -X, -CO-A-R ¹¹ or a radical of the general formula (V)

(V)

where Q ^{1 is in} each case a linear or branched CrC ₅₀ -alkyl, C ₅ -C ₂₀ -cycloalkyl, C ₅ -C ₂₀ -aryl,

-C ₅₀ -alkyl-substituted C ₅ -C ₂₀ aryl, C ₂ -C ₂₀ heterocycle, C ₂ -C ₂₀ -alkenylsubstituiertes C ₂ -C ₂₀ heterocycle, -C ₅₀ alkyl-substituted C ₂ -C ₂₀ heterocycle, C ₂ - C ₂₀ -alkenyl, C ₂ -C ₂₀ -alkenyl, a C ₂ -C ₂₀ alkenyl substituted C ₅ -C ₂₀ -Aryls, C ₂ -C ₂ alkynyl, or C ₂ - C ₂₀ -alkenylsubstituiertes C ₅ -C ₂₀ - Aryl is, in each case by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted

Nitrogen atoms, by double bonds, siloxane groups and / or by one or more groups of the type -C (O) O-, -OC (O) -, -C (O) -, -NHC (O) O-, -OC (O ) NH- and / or -OC (O) O-, and / or one or more functional groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups, carboxylic acid ester groups, carboxylic acid amide groups,

Carbonate groups, halogens, epoxy groups, trialkoxy-silane groups,

May have sulfonic acid groups and carbamate groups,

R ³ , R ^3a = OH, Q ² or a with its central nitrogen atom to a C atom of the triazine ring of the structure of the formula (I) bonded radical of the formula R ¹² -NR ¹³ , wherein

Q ^{2 is} a linear or branched C ₁ -C ₅₀ -alkyl or a cyclic substituent in the form of a C ₅ -C ₂₀ -cycloalkyl, a C ₅ -C ₂₀ -aryl, C ₂ -C ₂₀ -heterocycle, C ₂ -C ₂₀ -alkenyl-substituted C ₂ -C ₂₀ heterocycle, -C ₅₀ alkyl-substituted C ₂ -C ₂₀ - heterocycle, a CrC ₅₀ alkyl-substituted C ₅ -C ₂₀ -Aryls, C ₂ -C ₂₀ -alkenyl, a C ₂ - C ₂₀ alkenyl substituted C -Aryls ₅ -C _20, C ₂ -C ₂ alkynyl, or an imide of cyclic saturated or unsaturated carboxylic acids, the unsubstituted in each case by one or more oxygen atoms, sulfur atoms, substituted and / or Nitrogen atoms, by double bonds, siloxane groups and / or by one or more groups of the type -C (O) O-, -OC (O) -, -C (O) -, -NHC (O) O-, -OC (O ) NH- and / or -OC (O) O-, and / or one or more functional groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups, carboxylic acid ester groups, carboxamide groups,

Carbonate groups, halogens, epoxy groups, trialkoxy-silane groups,

May have sulfonic acid groups and carbamate groups,

R ⁴ , R ¹⁰ , R ^10a , R ¹² , R ¹³ , R ¹⁴ independently of one another have the meanings of R ²

R ⁵ , R ⁸ , R ⁹ independently of one another have the meanings of R ³ ,

R ⁶ and R ⁷ independently of one another linear or branched CrC ₅ o-alkyl or a cyclic substituent in the form of a C ₅ -C ₂ o-cycloalkyl, C ₂ -C ₂ o-alkenyl, C ₂ -C ₂ -alkynyl, a C ₅ -C ₂₀ -Aryls, a Ci-C ₅₀ alkyl-substituted C ₅ -C ₂₀ -Aryls, a C ₂ -C ₂₀ - alkenyl-C ₅ -C ₂₀ -Aryls, C ₂ -C ₂₀ heterocycle, C ₅₀ alkyl-substituted C ₂ -C ₂₀ heterocycle, C ₂ -C ₂₀ -alkenyl substituted C ₂ -C ₂₀ heterocycle, each by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted nitrogen atoms, by double bonds, siloxane groups and / or by one or more groups of the type -C (O) O-, -OC (O) -, -C (O) -, -NHC (O) O-, -OC (O) NH- and / or -OC ( O) O-, and / or one or more functional groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups,

Carboxylic acid ester groups, carboxamide groups, carbonate groups, halogens, epoxy groups, trialkoxy-silane groups, sulfonic acid groups and carbamate groups,

R ¹¹ -C ₅₀ linear or branched alkyl or a cyclic substituent in the form of a C ₅ -C ₂₀ -Cycloalkyls, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂ alkynyl, a C ₅ -C ₂₀ -Aryls, a -C ₅₀ - alkyl-substituted C ₅ -C ₂₀ -Aryls, a C ₂ -C ₂₀ alkenyl substituted C ₅ -C ₂₀ -Aryls, C ₂ -C ₂₀ - heterocycle, Ci-C ₅₀ alkyl-substituted C ₂ -C ₂₀ heterocycle, C ₂ -C ₂₀ -alkenylsubstituiertes C ₂ - C ₂₀ heterocycle which in each case by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted nitrogen atoms by double bonds, siloxane groups and / or by one or more groups of the type -C ( O) O-, -OC (O) -, - C (O) -, -NHC (O) O-, -OC (O) NH- and / or -OC (O) O- may be interrupted, and / or one or more functional groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups, carboxylic ester groups, carboxylic acid amide groups groups, carbonate groups, halogens, epoxy groups, trialkoxy-silane groups, sulfonic acid groups and carbamate groups

X = H ₁ Q ¹ or a radical of the general formula (VI)

means

Y has the meaning of Q ¹ ,

and n and m are independently> 1, where n = 1 can only be the case if R ^{1 is} a triazine ring residue.

The radical R ¹ is preferably a linear or branched CrCi ₅ o-alkyl, particularly preferably a Ci-Cioo-alkyl.

It is also advantageous if the radical R ^{1 is selected} from a group comprising radicals of a polyester, polyether, polyester ether, polycarbonate, polyester carbonate, polyether carbonate, polyacetal, polyolefin, polyacrylate or polysiloxane diol / polyol or diamines / polyamine or a -aminols having a molecular weight of 200 to 8000 g / mol is selected.

In a particularly preferred embodiment, the radical R ^{1 is} selected from a group comprising glycol, butanediol, hexanediol, ethylenediamine, butanediamine, hexanediamine and poly-THF. As used herein, the term "Ci-C ₂ oo-alkyl" refers to radicals such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, amyl, t-amyl, hexyl , Heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and longer chain radicals.

The term "C ₅ -C ₂ o-cycloalkyl" includes inter alia the groups cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl and higher-membered rings.

The term "C ₅ -C ₂ oo-aryl" as used herein refers to aromatic hydrocarbons, for example, phenyl, benzyl, naphthyl, or anthryl.

The term "C ₂ -C ₅ o heterocycle" refers to optionally substituted rings of 2-50 carbon atoms containing from 1 to 4 heteroatoms, such as oxygen, sulfur and / or nitrogen, especially nitrogen, either alone or in conjunction with These rings may be saturated or fully unsaturated or partially unsaturated, with fully saturated rings being preferred Preferred heterocyclic rings include piperidinyl, morpholinyl, piperazinyl, 2-amino-imidazoyl, tetrahydrofurano, pyrrolo, tetrahydrothiophenyl.

The term "C ₂ -C ₂ o-alkenyl" refers to a radical comprising a double bond, which may be substituted or unsubstituted The stereoisomerism is not essential and all stereoisomers may be used for a particular substituted alkenyl.

The term "C ₂ -C ₂ -alkynyl" as used herein refers to a radical of the formula C ₂ -C ₂ - = C- Examples of C ₂ -C ₂ alkynyls include:. Ethynyl, propynyl or propargyl, 2-butynyl, 2-pentynyl, 3-pentynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 2-heptynyl, 3-heptynyl, 4-heptynyl, 5-heptynyl, as well as octynyl, nonynyl, decynyl, undecynyl, dodecynyl and di- and tri-enes of straight and branched alkyl chains, preference being given to those alkynyl radicals in which the triple bond is terminal.

The terms "by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted nitrogen atoms and / or by one or more groups of the type -C (O) O-, -OC (O) -, -C (O) -, - NHC (O) O-, -OC (O) NH- and / or -OC (O) O- "preferably comprises the radicals -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -, -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -, -CH ₂ -CH ₂ -S- CH ₂ -CH ₂ -, -CH ₂ -CH ₂ -NH-CH ₂ -CH ₂ - , -CH ₂ -CH ₂ -N (CH 3) -CH ₂ -CH ₂ -, -CH ₂ -CH ₂ -CO-CH ₂ -CH ₂ , - CH ₂ -CH ₂ -COO-CH ₂ -CH ₂ The term "substituted", when used with "alkyl", "alkenyl", etc., refers to the substitution of one or more atoms, typically H atoms, by one or more of the following substituents, preferably by one or two of the following substituents : Halogen, hydroxy, protected hydroxy, oxo, protected oxo, C ₃ -C ₇ -cycloalkyl, phenyl, naphthyl, amino, protected amino, monosubstituted amino, protected monosubstituted amino, disubstituted amino, Other substituents are generally conceivable. Aryl groups, alkenyl groups, may be substituted once or several times, and preferably 1 or 2 times, with the same or different substituents.

The polymers according to the invention have molar masses between 400 and 50,000 g / mol, in particular between 500 and 20,000 g / mol.

The triazine polymers of the general formula (I) according to the invention can be prepared by reacting at least one compound of the general formula (VII) or (VIII)

where Y ¹ and Y ² independently of one another have the meaning of Q ¹ ,

R ¹⁵ = R ³ or a radical of the formula R ² -NC (O) OY attached to its central nitrogen atom to the C atom of the triazine ring of the structure of the formula (VII), and R ¹⁶ = R ³ or -NCO,

with at least one compound of the general formula (IX) HA ¹ -R ¹ -A ² -H

(IX).

The other radicals not explicitly defined here have the meaning described above.

Particularly suitable examples of compounds of the general formula (VII) are [4-amino-6- (methoxycarbonylamino) -1, 3,5-triazin-2-yl] -carbamic acid methyl ester, [4-amino-6- (butoxycarbonylamino) -i , 3,5-triazin-2-yl] -carbaminsäurebutylester; [4,6-bis (methoxycarbonylamino) -1, 3,5-triazin-2-yl] -carbamic acid methyl ester, [4,6-bis (butoxycarbonylamino) -1, 3,5-triazine-2 -yl] -carbamic acid butyl ester, [4-methylamino-6- (methoxycarbonyl-methyl-amino) -1, 3,5-triazin-2-yl] -methylcarbamic acid methyl ester, [4-methylamino-6-

(butoxycarbonyl-methyl-amino) -1,3,5-triazin-2-yl] -methylcarbamic acid butyl ester, [4,6-bis (methoxycarbonyl-methyl-amino) -i, 3,5-triazin-2-yl] methyl methylcarbamate, [4,6-bis (butoxycarbonylmethyl-amino) -1, 3,5-triazin-2-yl] -methylcarbamic acid butyl ester, [4-dimethylamino-6- (methoxycarbonylamino) -1, 3.5- triazin-2-yl] -carbamic acid methyl ester, [4-dimethylamino-6- (butoxycarbonylamino) -1, 3,5-triazin-2-yl] -carbamic acid butyl ester, [4

Dimethylamino-θ-dimethoxycarbonyl-amino-amino-methylamino, -dimethylamino---dibutoxycarbony-amino-amino-ε-triazine-α-butylcarbamate, [4-dimethylamino-6- (methoxycarbonyl-methyl-amino) -1,3,5-triazin-2-yl] -methylcarbamic acid methyl ester, [4-dimethylamino-6- (butoxycarbonyl-methyl-amino) -1,3,5-triazine-2-one yl] - methylcarbamic acid butyl ester, [4-methylamino-6- (methoxycarbonyl-methyl-amino) -1, 3,5-triazin-2-yl] -carbamic acid methyl ester, [4-methylamino-6- (butoxycarbonyl-methyl-amino ) - 1, 3,5-triazin-2-yl] -carbamic acid butyl ester, [4,6-bis (methoxycarbonyl-methyl-amino) -1, 3,5-triazin-2-yl] -carbamic acid methyl ester or [4, 6-Bis- (butoxycarbonyl-methyl-amino) -1,3,5-triazin-2-yl] -carbamic acid butyl ester.

The compounds of the general formula (VII) are, inter alia, by the reaction of at least one triazine derivative of the general formula (X)

(X)

with at least one chloroformate of the general formula (XI)

O

he ^ o - R ^{2 '}

(XI)

and / or the general formula (XII)

OO

(XII)

in the presence of at least one alkali or alkaline earth metal compound is possible, wherein preferably the alkali or alkaline earth metal compound is not present in the form of an alcoholate.

In the general formulas (X) to (XII) mean

R ^{1 '} , R ⁵ ', R ⁶ ', R ^7' and R ^{8 '} independently of one another H, Q ^2' , -CO-OR ^{2 '} , -CO-R ^9' or -CO-O-

R ^{10 ',} wherein - Q ² each ^represent a linear or branched Ci-C ₅ -alkyl, C ₅ -C ₂ o-cycloalkyl, C ₅ -C ₂₀ -

Aryl, Ci-C ₅₀ -alkyl-substituted C ₅ -C ₂₀ -aryl, C ₂ -C ₂₀ -heterocycle, C ₂ -C ₂₀ -alkenyl-substituted C ₂ -C ₂₀ -heterocycle, Ci-C ₅₀ alkyl-substituted C ₂ -C ₂₀ - is heterocycle, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂ alkynyl or C ₂ -C ₂₀ alkenyl-substituted C ₅ - C ₂₀ aryl, each by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted Nitrogen atoms, by double bonds,

Siloxane groups and / or by one or more groups of the type -C (O) O-, -OC (O) -, -C (O) -, -NHC (O) O-, -OC (O) NH- and / or -OC (O) O-, and / or comprising one or more functional groups from the class Hydroxyl groups, mercapto groups, carboxylic acid groups,

Carboxylic acid ester groups, carboxylic acid amide groups, carbonate groups, halogens, epoxy groups, trialkoxy-silane groups, sulfonic acid groups and carbamate groups,

R ^{2 'is} a linear or branched Ci-C ₅₀ alkyl, C ₅ -C ₂ o-cycloalkyl, C ₅ -C ₂₀ aryl, -C ₅₀ - alkyl-substituted C ₅ -C ₂₀ aryl, C ₂ -C ₂₀ -heterocycle , C ₂ -C ₂₀ -alkenyl-substituted C ₂ -C ₂₀ -

Heterocycle, -C ₅₀ alkyl-substituted C ₂ -C ₂₀ heterocycle, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂ -

Alkynyl or C ₂ -C ₂₀ -alkenyl-substituted C ₅ -C ₂₀ -aryl, each by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted

Nitrogen atoms, by double bonds, siloxane groups and / or by one or more groups of the type -C (O) O-, -OC (O) -, -C (O) -, -NHC (O) O-, -OC (O ) NH- and / or -OC (O) O- may be interrupted and / or has one or more halogen atoms as substituents,

R ^{3 '} Q ¹ or a with its central nitrogen atom to a C atom of the triazine ring of the structure of the formula (I) bonded radical of the formula R ⁵ -NR ⁶ , wherein - Q ^{1 is} a linear or branched CrC ₅₀ alkyl or a cyclic substituents in the form of a C ₅ -C ₂₀ cycloalkyl, a C ₅ -C ₂₀ aryl, C ₂ -C ₂₀ heterocycle, C ₂ -C ₂₀ alkenyl substituted C ₂ -C ₂₀ heterocycle, C ₁ -C ₅₀ alkyl substituted C ₂ -C ₂₀ -

Heterocycle, a CrC ₅₀ alkyl-substituted C ₅ -C ₂₀ -Aryls, C ₂ -C ₂₀ -alkenyl, a C ₂ - C ₂₀ alkenyl substituted C ₅ -C ₂₀ -Aryls, C ₂ -C ₂ alkynyl, or an imide of cyclic saturated or unsaturated carboxylic acids, each by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted nitrogen atoms, by double bonds, siloxane groups and / or by one or more groups of the type -C (O) O-, -OC (O ) -, -C (O) -, -NHC (O) O-, -OC (O) NH- and / or -OC (O) O-, and / or one or more functional groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups, carboxylic acid ester groups, carboxamide groups, carbonate groups, halogens, epoxy groups, trialkoxy-silane groups,

May have sulfonic acid groups and carbamate groups,

R Q or one with the nitrogen atom to a C atom of the triazine ring of the structure of

Formula (I) bonded radical of the formula R ^{7 '} -NR ^8' ,

R ^{9 'is} a radical of the general formula (XIII)

(XIII)

means

R ^{10 'is} a radical of the general formula (XIV)

in which

- R ^{11 'are} each a linear or branched Ci-C ₅ o-alkyl, C ₅ -C ₂ o-cycloalkyl, C ₅ -C ₂₀ - aryl, dC ₅ o-alkyl-substituted C ₅ -C ₂₀ -aryl, C ₂ -C ₂₀ heterocycle, C ₂ -C ₂₀ - alkenyl-C ₂ -C ₂₀ -heterocycle, Ci-C ₅₀ alkyl-substituted C ₂ -C ₂₀ - heterocycle, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂ alkynyl or C ₂ -C ₂₀ -alkenylsubstituiertes C ₅ - C ₂₀ aryl, which (in each case by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted nitrogen atoms by double bonds, siloxane and / or the type -C by one or more groups O) O-, -OC (O) -, -C (O) -, -NHC (O) O-, -OC (O) NH- and / or -OC (O) O- may be interrupted, and / or one or more functional groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups,

Carboxylic acid ester groups, carboxylic acid amide groups, carbonate groups, halogens, epoxy groups, trialkoxy-silane groups, sulfonic acid groups and carbamate groups, The compounds of general formula (VII) are also obtained by the reaction of at least one triazine derivative of general formula (X) with at least one acyclic carbonate of formula (XV)

O

A ^r Cf ^ OR ^{2 "}

(XV)

and / or at least one carbamate of the formula (XVI)

(XVI)

where R ^{1 is} the meaning of R ^{1 '} , R ^{2 is} the meaning of R ² , R ^{3 is} the meaning of R ³ and R ⁴ "has the meaning of R ⁴ , and A ¹ ' is Q ² or a radical of a substituted or unsubstituted Alcohol means

with continuous removal of the compound A ¹ '-OH formed during the reaction from the reaction equilibrium with the preferred proviso that no basic compound is added to the reaction mixture.

Examples of suitable compounds of the formula (VIII) are, for. B. 2,4,6-triisocyanato-1, 3,5-triazine, 2-amino-4,6-diisocyanato-1, 3,5-triazine, 2- (dimethylamino) -4,6-diisocyanato-1, 3,5-triazine, 2- (diethylamino) -4,6-diisocyanato-1, 3,5-triazine and / or 2- (dibutylamino) -4,6-diisocyanato-1,3,5-triazine

Examples of compounds of the general formula (IX) which are suitable for the preparation of polymers of the formula (I) HA ¹ -R ¹ -A ² -H

(IX)

are polyether, polyester and polycarbonate diols or polyols of the prior art. These compounds are well known in polyurethane chemistry. A selection of possible polyether and polyester polyols is z. For example, described in K. Schauerte, P. Gupta, Plastics Handbook Volume 7 Polyurethane, 3rd edition, Carl Hanser Verlag 1993, pp 57-75 or in K. UhNg, polyurethane paperback, Carl Hanser Verlag 2001, p 120- 127th

Suitable polycarbonate diols or polyols can be prepared by the reaction of carbonic acid derivatives, such as. As diphenyl carbonate, dimethyl carbonate, phosgene or the like, with diol components, such as. B. 1, 4-butanediol, 1, 3-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 1, 8-octanediol, 1, 12-dodecanediol, neopentyl glycol, 1, 4-bishydroxymethylcyclohexane, 2-methyl 1, 3-propanediol, trimethylpentanediol-1, 3 or similar diols produce.

In an analogous manner, it is also possible to prepare suitable diamines and polyamines, as well as aminoles.

It is also possible to use any desired mixtures of these compounds for polymer production.

The polymeric diols / polyols or diamines / polyamines used preferably have a molecular weight of 200-8000 g / mol, especially a molecular weight of 200-4000 g / mol, in particular 250-2000 g / mol.

Suitable diols which can be used as the compound of general formula (IX) HA ¹ -R ¹ -A ² -H are aliphatic, alicyclic or aromatic compounds such. For example, ethylene glycol, diethylene glycol, 1, 2-propanediol, 1, 3-propanediol, 1, 4-butanediol, 1, 3-butylene glycol, cyclohexanediol, 1, 4-cyclohexanedimethanol, 1, 6-hexanediol, neopentyl glycol, Hydrochinondihydroxyethylether, bisphenol A. , hydrogenated bisphenol A, α-hydroxybutyl-ε-hydroxy-caproic acid ester, ω-hydroxyhexyl-γ-hydroxybutyric acid ester, adipic acid (β-hydroxyethyl) ester or terephthalic acid bis (β-hydroxyethyl) ester. Suitable diamines which can be used as the compound of the general formula (IX) HA ¹ -R ¹ -A ² -H are aliphatic, alicyclic or aromatic compounds, such as. As ethylenediamine, propylenediamine, hexamethylenediamine-1, 6, 1, 4-bis (aminomethyl) cyclohexane, 4,4'-diamino-3,3'-dimethyldicyclohexylmethane or 4,4'-diamino-3,5-diethyl-3 ', 5'-diisopropyldicyclohexyl-methane.

Suitable diols or polyols for the preparation of polymers of formula (I) are also hydroxyalkyl-functionalized triazine derivatives such. 2- [4-amino-6- (2-hydroxyethylamino) -1,3,5-triazin-2-ylamino] -ethanol, 2 - [(4,6-diamino-1,3,5-triazine) 2-yl) - (2-hydroxyethyl) amino] ethanol, 2- [4,6-bis (2-hydroxyethylamino) -1, 3,5-triazin-2-ylamino] ethanol, 2 - [[ 4-Amino-6- (2-hydroxyethylamino) -1, 3,5-triazin-2-yl] - (2-hydroxyethyl) amino] ethanol, 2 - [{4-amino-6-bis-bis ( 2-hydroxyethyl) amino] -1, 3,5-triazin-2-yl} - (2-hydroxyethyl) amino] ethanol, 2- [4- [bis (2-hydroxyethyl) amino] -6 - (2-hydroxyethylamino) -1, 3,5-triazin-2-ylamino] ethanol, 2- {4,6-bis [bis (2-hydroxyethyl) amino] -1, 3,5-triazine -2-ylamino} -ethanol, 2 - [{4,6-bis [bis (2-hydroxyethyl) amino] -1, 3,5-triazin-2-yl} - (2-hydroxyethyl) -amino] ethanol, 2- [4-amino-6- (2-hydroxyethyl-methylamino) -1, 3,5-triazin-2-ylmethylamino] -ethanol, 2- [4,6-bis ( 2-hydroxyethylmethylamino) -1, 3,5-triazin-2-ylmethylamino] ethanol, 2- [4-amino-6- (2-hydroxyethyl-butylamino) -1, 3,5-triazine-2 -ylbutylamino] ethanol, 2- [4,6-bis (2-hydroxyethyl-butylamino) -1, 3,5-triazin-2-yl-butylamino] -ethanol, 2 - [4-amino-6- (2-hydroxyethyl-hexylamino) -1, 3,5-triazin-2-yl-hexylamino] -ethanol, 2- [4,6-bis (2-hydroxyethyl-hexylamino) -1, 3,5-triazin-2-yl-hexylamino] -ethanol, 2- (2- {4-amino-6- [2- (2-hydroxy-ethoxy) -ethyl-amino] -1, 3,5-triazin-2-ylamino} - ethoxy) - ethanol or 2- (2- {4,6-bis- [2- (2-hydroxyethoxy) -ethylamino] -1, 3,5-triazin-2-ylamino} -ethoxy) -ethanol.

Also suitable as a component of the formula (IX) HA ¹ -R ¹ -A ² -H are also those compounds of general structure (VII) in which R ² and R ^{4 are} simultaneously H or one of R ² or R ⁴ is H and at the same time the radical R ¹⁵ is NHR or NH ₂ . This leads to a self-condensation of compounds of general formula (VII) and thus quasi to a triazine homopolymer.

The preparation of the polymers of the general formula (I) takes place at the reaction conditions known from polyurethane production.

The process for preparing the triazine polymers of the formula (I) comprises the following process steps: a) mixing at least one compound of the formula (VII) or (VIII) with at least one compound of the formula (IX), if appropriate in the presence of a solvent, for example N-methylpyrrolidine (NMP), dimethylformaind (DMF) or dimethylacetamide (DMAc), b) optionally adding a catalyst, and c) heating the mixture to temperatures between 40 and 180 ^° C.

After the reaction has ended, the mixture is cooled and the polymer formed is isolated in a manner known to a person skilled in the art.

Optionally, known catalysts or other auxiliaries can be added. Examples of catalysts or further auxiliaries to be used according to the invention are described in P. Haas, K. UhNg, Kunststoff Handbuch, Volume 7 Polyurethane, 3rd edition, Carl Hanser Verlag 1993, pp. 104-126.

Preferred field of application of the polymers according to the invention is e.g. the use as a binder in paints and varnishes for metal, plastic, wood and paper coatings.

A particularly preferred use is in the form of baked enamels.

Further fields of use are the use of the polymers as hard and soft foams, in particular in the form of block products, plates, integral foam, one-component foam and / or pipe insulation, components in adhesives and sealants, in particular in the construction industry, packaging industry, shoe industry, as elastomers, in particular Form of TPU's, fibers and / or casting elastomers, and as a binder, in particular for wood products, casting cores and / or rubber particles.

The invention will be discussed below with reference to several embodiments.

Example 1 :

1, 2 mol of 2,2-Dimethylmelamindiisocyanat is reacted with 1 mole of PEG 200 at 40 ⁰ C and added to the reaction, the reaction product in dimethylacetamide. Subsequently, 0.3 mol of butanediol are added and stirred at 80 ° C for 20h. Upon cooling, the polymer precipitates out of the solvent. The polymer is filtered off and dried in vacuo. The GPC analysis gives an M _w of 4500 g / mol with a broad molecular weight distribution. Example 2:

1, 1 mol of 2,2-Dibutylmelamindiisocyanat is reacted with 1 mol of PEG 1000 at 60 ⁰ C and added to the reaction, the reaction product in N-methylpyrrolidone. Subsequently, 0.15 mol of ethylenediamine are added and stirred at 60 ⁰ C for 1 h. The solution is added dropwise in 10 times the amount of methanol and the precipitated polymer is then filtered off with suction and dried in vacuo. The GPC analysis gives an M _w of 18,700 g / mol with a broad molecular weight distribution.

Example 3:

1, 2mol [4-dimethylamino-6- (butoxycarbonylamino) -1, 3,5-triazin-2-yl] -carbaminsäurebutyl- ester is reacted with 1 mol of polypropylene glycol diol 600 at 75 ° C for 3h and the reaction product taken up in N-methylpyrrolidone. Then 0.25 mol of 1, 6-hexanediol are added and stirred at 100 ⁰ C for 3h. The solution is added dropwise to 10 times the amount of methanol and the precipitated polymer is then filtered off with suction and dried in vacuo. The GPC analysis gives an M _w of 23,000 g / mol with a broad molecular weight distribution.

Example 4:

1, 5mol [4-dimethylamino-6- (methoxycarbonylamino) -1, 3,5-triazin-2-yl] -carbaminsäure- methyl ester with 1 mol of 2- [4-amino-6- (2-hydroxyethylamino) -1 , 3,5-triazin-2-ylamino] - ethanol reacted in dimethylformamide at 80 ° C for 5h. To accelerate the reaction, the resulting methanol is distilled off. The product is precipitated in 10 times the amount of isopropanol and dried after isolation in vacuo. The polymer has an M _w of 3350 g / mol. Standard bars produced in this way achieve the level VO in the UL94 test.

Example 5:

A mixture of 100 parts of a polyether of propylene oxide and ethylene oxide, 0.5 part of water and 0.5 part of DABCO is thoroughly mixed with 40 parts of 2,2-diethyl melamine diisocyanate and poured into a mold. The mold is heated for 24 h at 80 ° C and removed the moldings. The test specimens produced therefrom show a tensile strength of 6.3 MPa and an elongation at break of 570%. Example 6:

A mixture of 1 mol equivalent of [4,6-bis (methoxycarbonyl-methyl-amino) -1, 3,5-triazine

2-yl] -methylcarbamic acid butyl ester, 0.7 molar equivalent of 2 - [(4,6-diamino-1,3,5-triazin-2-yl) - (2-hydroxyethyl) amino] ethanol and 0.3 mol equivalent of butanediol is thoroughly mixed at 110 ⁰ C and stirred until the viscosity has risen to 5 Pa ^* s.

Subsequently, this mixture is mounted on a preheated steel plate with a spiral blade and annealed at 130 ⁰ C for 3 h. Now the temperature rises within 1 h

Increased 160 ° C and leave the steel plate for another 1 h in a warming cabinet. The resulting paint film shows a flexibility (depth test according to DIN EN ISO 1520) of 0.8 mm and a

Hardness (pendulum hardness according to DIN EN ISO 1522 / method according to KÖNIG) of 245s.

Claims

claims

1) Triazine polymers of the general formula (I)

(I)

or mixtures thereof, wherein

A ¹ and A ² independently of one another denote O, NH or NR ¹⁴

R ¹ = a linear or branched Ci-C ₂ oo-alkyl, a cyclic substituent in the form of a C ₅ - C ₂ o-cycloalkyl, a C ₂ -C ₂ -alkenyl, C ₂ -C ₂ alkynyl, a C ₅ -C _2oo aryl, a Ci-C ₂₀₀ - alkyl-substituted C ₅ -C _2O o-aryl, C ₂ -C ₂₀ -alkenylsubstituiertes C ₅ -C _2O o-aryl, C ₂ -C ₅₀ - heterocycle, a Ci-C _2O o-alkyl-substituted C ₂ -C ₅₀ heterocycle, a C ₂ -C ₂₀ - alkenyl-C ₂ -C ₅₀ -heterocycle, where the radicals, by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted nitrogen atoms by double bonds, siloxane groups and / or by one or more groups of the type -C (O) O-, -OC (O) -, -C (O) -, -NHC (O) O-, -OC (O) NH and / or -OC (O) O- and / or one or more functional groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups, carboxylic acid ester groups, carboxamide groups, carbonate groups, halogens, epoxy groups, trialkoxy silane groups, May have sulfonic acid groups and carbamate groups,

or a group of the formulas (II) to (IV)

wherein the molar mass of the radical R ^{1 is} between 200 and 8000 g / mol, and where the radical R ¹ in the polymer may be the same or different,

means, where

- Q ¹ are each a linear or branched Ci-C ₅ -alkyl, C ₅ -C ₂ o-cycloalkyl, C ₅ -C ₂₀ aryl, C ₅ o-alkyl-substituted C ₅ -C ₂₀ aryl, C ₂ -C ₂₀ heterocycle, C ₂ -C ₂₀ alkenyl substituted C ₂ -C ₂ o-heterocycle, C ₁ -C ₅₀ -alkyl-substituted C ₂ -C ₂ o-heterocycle, C ₂ -C ₂ o-alkenyl, C ₂ -C ₂ o-alkenyl, a C ₂ -C ₂ o- alkenyl-C ₅ -C ₂ o-aryl, C ₂ -C ₂ alkynyl, or C ₂ - C ₂₀ -alkenylsubstituiertes C ₅ -C ₂₀ -aryl, which in each case by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted nitrogen atoms , by double bonds, siloxane groups and / or by one or more groups of the type -C (O) O-, -OC (O) -, -C (O) -, -NHC (O) O-, -OC (O) NH- and / or -OC (O) O- and / or one or more functional groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups, carboxylic acid ester groups, carboxylic acid amide groups, carbonate groups, halogens, epoxy groups, trialkoxy-silane groups,

May have sulfonic acid groups and carbamate groups,

R ³ , R ^3a = OH, Q ² or one with its central nitrogen atom to a C atom of the TTrriiaazziinnringes the structure of the formula (I) bonded radical of the formula R ¹² -NR ¹³ , wherein

Q ^{2 is} a linear or branched C 1 -C ₅₀ -alkyl or a cyclic substituent in the form of a C ₅ -C ₂₀ -cycloalkyl, a C ₅ -C ₂₀ -aryl, C ₂ -C ₂₀ -heterocycle, C ₂ -C ₂₀ - alkenyl-C ₂ -C ₂₀ -heterocycle, _Ci-50 alkyl-substituted C C ₂ -C ₂₀ - heterocycle, a _Ci-50 alkyl-substituted C ₅ -C ₂₀ -Aryls C, C ₂ -C ₂₀ -alkenyl, a C ₂ - alkenyl substituted C ₂₀ C ₅ -C ₂₀ -Aryls, C ₂ -C ₂ alkynyl, or an imide of cyclic saturated or unsaturated carboxylic acids, which in each case by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted nitrogen atoms by double bonds , Siloxangruppen and / or by one or more groups of the type -C (O) O-, -OC (O) -, -C (O) -, -NHC (O) O-, -OC (O) NH- and / or -OC (O) O- may be interrupted, and / or one or more functional

Groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups, carboxylic ester groups, carboxylic acid amide groups, carbonate groups, halogens, epoxy groups, trialkoxy-silane groups,

May have sulfonic acid groups and carbamate groups,

R ⁵ , R ⁸ , R ⁹ independently of one another have the meanings of R ³

R ⁶ and R ⁷ independently of one another linear or branched CrC ₅₀ alkyl or a cyclic substituent in the form of a C ₅ -C ₂₀ cycloalkyl, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂ alkynyl, a C ₅ -C ₂₀ -aryls, a Ci-C ₅₀ -alkyl-substituted C ₅ -C ₂₀ -aryl, a C ₂ -C ₂₀ - alkenyl-substituted C ₅ -C ₂₀ -aryl, C ₂ -C ₂₀ -heterocycle, Ci-C ₅₀ alkyl-substituted C ₂ -C ₂₀ - Heterocycle, C ₂ -C ₂ o-alkenyl-substituted C ₂ -C ₂ o-heterocycle, each by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted nitrogen atoms, by double bonds, siloxane groups and / or by one or more groups of Type -C (O) O-, -OC (O) -, -C (O) -, -NHC (O) O-, -OC (O) NH- and / or -OC (O) O- can, and / or one or more functional groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups,

R ¹¹ linear or branched CrC ₅ o-alkyl or a cyclic substituent in the form of a C ₅ -C ₂ o-cycloalkyl, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂ alkynyl, a C ₅ -C ₂₀ aryl , a -C ₅₀ - alkyl-substituted C ₅ -C ₂₀ -Aryls, a C ₂ -C ₂₀ alkenyl substituted C ₅ -C ₂₀ -Aryls, C ₂ -C ₂₀ - heterocycle, Ci-C ₅₀ alkyl-substituted C ₂ -C ₂₀ - heterocycle, C ₂ -C ₂₀ -alkenylsubstituiertes C ₂ - C ₂₀ heterocycle which in each case by one or more oxygen atoms, sulfur atoms, substituted and / or unsubstituted nitrogen atoms by double bonds, siloxane and / or of the type with one or more groups - C (O) O-, -OC (O) -, - C (O) -, -NHC (O) O-, -OC (O) NH- and / or -OC (O) O- may be interrupted, and / or one or more functional groups from the class comprising hydroxyl groups, mercapto groups, carboxylic acid groups, carboxylic acid ester groups, carboxylic acid amide groups, carbonate groups, halogens, epoxy groups, trialkoxy-silane groups, sulfonic acid groups and carbamate groups

X = H ₁ Q ¹ or a radical of the general formula (VI)

means

Y has the meaning of Q ¹ and n and m independently of one another are ≥ 1, where n = 1 can only be the case if R ^{1 represents} a residue with triazine ring.

2. triazine polymers according to claim 1, characterized in that the radical R ^{1 is} selected from a group comprising radicals of a polyester, polyether, polyester, polycarbonate, polyester, polyether, polyacetal, polyolefin, polyacrylate or polysiloxane - Diols / polyols or diamine / polyamine or a -aminols having a molecular weight of 200 to 8000 g / mol.

3. triazine polymers according to claim 1 or 2 characterized by a molecular weight between 400 to 50,000 g / mol, in particular 500 to 20,000 g / mol.

4. triazine polymers according to one of the preceding claims preparable by reacting at least one compound of general formula (VII) or (VIII)

where Y ¹ and Y ² independently of one another have the meaning of Q ¹ ,

R ¹⁵ = R ³ or a radical of the formula R ² -NC (O) OY attached to its central nitrogen atom to the C atom of the triazine ring of the structure of the formula (VII), and R ¹⁶ = R ³ or -NCO, the further radicals having the meaning in one of the preceding claims,

with at least one compound of the general formula (IX) HA ¹ -R ¹ -A ² -H

(IX).

5. triazine polymers according to claim 4, characterized in that as compounds of general formula (VII) [4-amino-6- (methoxycarbonylamino) -1, 3,5-triazin-2-yl] - carbamic acid, [4-amino- 6- (butoxycarbonylamino) -1, 3,5-triazin-2-yl] -carbamic acid butyl ester; [4,6-Bis (methoxy-carbonylamino) -1, 3,5-triazin-2-yl] -carbamic acid methyl ester, [4,6-bis (butoxycarbonylamino) -1, 3,5-triazine -2-yl] -carbamic acid-butyl ester, [4-methylamino-6- (methoxycarbonyl-methyl-amino) -1, 3,5-triazin-2-yl] -methylcarbamic acid methyl ester, [4-methylamino-6 - (butoxycarbonyl-methyl-amino) -1, 3,5-triazin-2-yl] -methyl-butylcarbamate, [4,6-bis (methoxycarbonyl-methyl-amino) -1, 3,5-triazin-2-yl ] - methylcarbamic acid methyl ester, [4,6-bis (butoxycarbonyl-methyl-amino) -1, 3,5-triazin-2-yl] -methyl-carbamic acid butyl ester, [4-dimethylamino-6- (methoxycarbonylamino) -1, 3 Methyl 5-triazin-2-yl] -carbamate, [4-dimethylamino-6- (butoxycarbonylamino) -1, 3,5-triazin-2-yl] -carbamic acid butyl ester, [4-dimethylamino-6 - ({dimethoxycarbonyl} amino ) -1, 3,5-triazin-2-yl] -carbamic acid methyl ester, [4-dimethylamino-6 - ({dibutoxycarbonyl} amino) -1, 3,5-triazin-2-yl] -carbamic acid butyl ester, [4-dimethylamino -6- (methoxycarbonyl-methyl-amino) -1, 3,5-triazin-2-yl] -m ethylcarbamic acid methyl ester, [4-dimethylamino-6- (butoxycarbonylmethylamino) -1, 3,5-triazin-2-yl] -methylcarbamic acid butyl ester, [4-methylamino-6- (methoxycarbonylmethylamino) -1, 3,5-triazin-2-yl] - carbamic acid methyl ester, [4-methylamino-6- (butoxycarbonyl-methyl-amino) -1, 3,5-triazin-2-yl] -carbamic acid butyl ester, [4 , 6-bis

(methoxycarbonyl-methyl-amino) -1, 3,5-triazin-2-yl] -carbamic acid methyl ester or [4,6-bis (butoxycarbonyl-methyl-amino) -i, 3,5-triazin-2-yl] - Carbamic acid butyl ester can be used.

6. Triazinpolymere according to claim 4 or 5, characterized in that as compounds of formula (VIII) 2,4,6-triisocyanato-1, 3,5-triazine, 2-amino-4,6-diisocyanato- 1, 3, 5-triazine, 2- (dimethylamino) -4,6-diisocyanato-1, 3,5-triazine, 2- (diethylamino) -4,6-diisocyanato-1, 3,5-triazine and / or 2- (dibutylamino ) -4,6-diisocyanato-1, 3,5-triazine can be used.

7. Triazine polymers according to any one of claims 4 to 6, characterized in that are used as compounds of formula (IX) diols, polyether, polyester, polycarbonate, polyols, diamine and / or polyamines.

8. Triazinpoylmere according to claim 7, characterized in that the polycarbonate diols and / or polyols used by reaction of carbonic acid derivatives, in particular of diphenyl carbonate, dimethyl carbonate and / or phosgene with diol components, in particular of 1, 4-butanediol, 1, 3-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 1, 8-octanediol, 1, 12-dodecanediol, neopentyl glycol, 1, 4

Bishydroxymethylcyclohexane, 2-methyl-1, 3-propanediol and / or trimethylpentanediol-1, 3 are available.

9. triazine polymers according to claim 7, characterized in that as diols aliphatic, alicyclic and aromatic diols, in particular ethylene glycol, diethylene glycol, 1, 2

Propanediol, 1,3-propanediol, 1,4-butanediol, 1,3-butylene glycol, cyclohexanediol, 1,4-cyclohexanedimethanol, 1,6-hexanediol, neopentyl glycol, hydroquinone dihydroxyethyl ether, bisphenol A, hydrogenated bisphenol A, α-hydroxybutyl-ε hydroxy-caproic acid ester, ω-hydroxyhexyl-γ-hydroxybutyric acid ester, adipic acid (β-hydroxyethyl) ester and terephthalic acid bis (β-hydroxyethyl) ester.

10. triazine polymers according to claim 7, characterized in that as diamines aliphatic, alicyclic and / or aromatic compounds, in particular ethylenediamine, propylenediamine, hexamethylenediamine-1, 6, 1, 4-bis (aminomethyl) cyclohexane, 4,4'-diamino 3,3'-dimethyldicyclohexylmethane and / or 4,4'-diamino-3,5-diethyl-3 ', 5'-diisopropyldicyclohexylmethane.

1 1. triazine polymers according to claim 7, characterized in that as diols or polyols hydroxyalkyl-functionalized triazine derivatives in particular 2- [4-amino-6- (2-hydroxyethylamino) -1, 3,5-triazin-2-ylamino] ethanol, 2 - [(4,6-diamino-1,3,5-triazin-2-yl) (2-hydroxyethyl) amino] ethanol, 2- [4,6-bis (2-hydroxyethylamino) -1, 3,5-triazin-2-ylamino] - ethanol, 2 - [[4-amino-6- (2-hydroxyethylamino) -1, 3,5-triazin-2-yl] - (2-hydroxyethyl) -amino] ethanol, 2 - [{4-amino-6- [bis (2-hydroxyethyl) amino] -1, 3,5-triazin-2-yl} - (2-hydroxyethyl) amino] ethanol, 2 - [4- [bis (2-hydroxyethyl) amino] -6- (2-hydroxyethylamino) -1, 3,5-triazin-2-ylamino] ethanol, 2- {4,6-bis [bis - (2-hydroxyethyl) amino] -1, 3,5-triazin-2-ylamino} ethanol, 2- [{4,6-bis [bis (2-hydroxyethyl) amino] -1 , 3,5-triazin-2-yl} (2-hydroxyethyl) amino] ethanol, 2- [4-amino-6- (2-hydroxy-ethyl-methylamino) -1, 3,5-triazine 2-ylmethylamino] ethanol, 2- [4,6-bis (2-hydroxyethylmethylamino) -1, 3,5-triazin-2-ylmethylamino] ethanol, 2- [4-amino-6- (2 - H y-hydroxyethyl-butyl-amino) -1, 3,5-triazin-2-yl-butylamino] -ethanol, 2- [4,6-bis- (2-hydroxy-ethyl-butylamino) -1, 3,5-triazin-2-yl-butylamino ] -ethanol, 2- [4-amino-6- (2-hydroxyethyl-hexylamino) -1,3,5-triazin-2-yl-hexylamino] -ethanol, 2- [4,6-bis (2-hydroxyethyl- hexylamino) -1, 3,5-triazine-2 ylhexylamino] ethanol, 2- (2- {4-amino-6- [2- (2-hydroxyethoxy) ethylamino] -1, 3,5-triazine-2-ylamino} -ethoxy) ethanol and / or 2 - (2- {4,6-bis [2- (2-hydroxyethoxy) ethylamino] -1, 3,5-triazin-2-ylamino} -ethoxy) -ethanol.

12. Triazinpolymere according to one of claims 4 to 6, characterized in that as the compound of formula (IX) compounds of general formula (VII) in which R ² and R ^{4 are} simultaneously H or one of R ² or R ⁴ is H and at the same time the radical R ¹⁵ is NHR or NH ₂ used.

13. triazine polymers according to any one of claims 4 to 12, characterized in that the compounds of formula (IX) has a molecular weight of 200 - 8000 g / mol, preferably a molecular weight of 200 - 4000 g / mol, particularly preferably a molecular weight of 250- 2000 g / mol.

14. Triazine polymers according to any one of claims 4 to 13, characterized in that the reaction of at least one compound of formula (VII) or (VIII) with the at least one compound of formula (IX) takes place at temperatures between 80 and 140 ° C.

15. A process for preparing triazine polymers according to any one of the preceding claims comprising the following process steps: a) mixing at least one compound of formula (VII) or (VIII) with at least one compound of formula (IX), b) optionally adding a catalyst, and c) heating the mixture to temperatures between 40 and 180 ^° C.

16. Use of triazine polymers according to any one of claims 1 to 14 as binders in paints and varnishes for metal, plastic, wood and paper coatings, in particular in baking finishes.

17. Use of triazine polymers according to one of claims 1 to 14 as hard and soft foams, in particular in the form of block goods, plates, integral foam, one-component foam and / or pipe insulation, as constituents in adhesives and sealants, in particular in the construction industry, packaging industry, shoe industry , as elastomers, in particular in the form of TPU's, fibers and / or cast elastomers, and as binders, in particular for wood products, casting cores and / or rubber particles.