WO2009080787A1 - Polymères urée-mélamine hyperramifiés - Google Patents

Polymères urée-mélamine hyperramifiés Download PDF

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WO2009080787A1
WO2009080787A1 PCT/EP2008/068098 EP2008068098W WO2009080787A1 WO 2009080787 A1 WO2009080787 A1 WO 2009080787A1 EP 2008068098 W EP2008068098 W EP 2008068098W WO 2009080787 A1 WO2009080787 A1 WO 2009080787A1
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alkylene
alkyl
radicals
iii
hydrogen
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PCT/EP2008/068098
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German (de)
English (en)
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Maxim Peretolchin
Eva RÜBA
Daniel SCHÖNFELDER
Bernd Bruchmann
Günter Scherr
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
    • C08G71/02—Polyureas
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/0644—Poly(1,3,5)triazines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/005—Hyperbranched macromolecules

Definitions

  • the present invention relates to a process for the preparation of highly branched urea-melamine polymers, which comprises condensing urea or a urea derivative, melamine and at least one amine, wherein the at least one amine comprises a diamine or polyamine having two primary amino groups.
  • the invention relates to the highly branched urea-melamine polymers obtainable by the process according to the invention and their use as adhesion promoters, thixotropic additives, rheology additives, solubilizers, as surface modifiers or as building blocks for the production of paints, coatings, adhesives, sealants, cast elastomers or foams.
  • hyperbranched polymers also referred to as hyperbranched polymers
  • their preparation is based on di or trifunctional monomers, which are reacted in a one-pot polycondensation reaction to high molecular weight and highly branched polymers.
  • Highly branched polymers in some way represent the transition between linear, unbranched polymers and fully branched dendrimers.
  • hyperbranched polymers provide an attractive alternative to the expensive to build and thus costly dendrimers.
  • the high functionality of highly branched polymers opens up numerous, very broad application possibilities.
  • these polymers as adhesion promoters, thixotropic agents, as building blocks for the production of paints, coatings, adhesives, sealants, cast elastomers or foams, as catalysts for the synthesis of polyurethane, as initiators for alkoxylations with alkylene oxides for the production of polyols, as vehicles, for example for catalysts or for medical purposes, eg.
  • catalysts for the synthesis of polyurethane as initiators for alkoxylations with alkylene oxides for the production of polyols
  • vehicles for example for catalysts or for medical purposes, eg.
  • drug delivery in the organism or complexation of various substances such as contrast agents, as a solubilizer, surface modifiers, etc. are used.
  • WO 2005/044897 describes highly functional, highly branched polyureas which are obtainable by reacting one or more carbonates with one or more amines having at least two primary and / or secondary amino groups.
  • WO 2005/075541 also describes highly functional, highly branched polyureas which are obtainable by reacting one or more ureas with one or more amines having at least two primary and / or secondary amino groups.
  • branching polyfunctional amines are needed, which are not readily synthetically accessible and therefore expensive.
  • the object of the present invention was therefore to provide highly functional, highly branched polymers which can be prepared from readily available and inexpensive starting materials.
  • the object is achieved by a process for the preparation of highly branched urea-melamine polymers, comprising the reaction of (i) urea and / or at least one urea derivative; (ii) melamine; and
  • At least one amine at least one amine, wherein the at least one amine (iii.1) contains 20 to 100 mol%, based on the total amount of the components (iii.1),
  • melamine derivative selected from benzoguanamine, substituted melamines and melamine condensates.
  • Ci-C4-alkyl is a linear or branched alkyl radical having 1 to 4 carbon atoms. These are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl.
  • Ci-C4-alkyl represents a linear alkyl radical having 1 to 4 carbon atoms. These are methyl, ethyl, n-propyl and n-butyl.
  • Ci-Ci2-alkyl is a linear or branched alkyl radical having 1 to 12 carbon atoms. Examples of these are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, 2-propylheptyl, 4 -Methyl-2-propyl hexyl, undecyl, dodecyl and their constitution isomers.
  • Aryl represents a carbocyclic aromatic radical having 6 to 14 carbon atoms, such as phenyl, naphthyl, anthracenyl or phenanthrenyl.
  • Aryl is preferably phenyl or naphthyl and in particular phenyl.
  • Aryl-Ci-C4-alkyl is Ci-C4-alkyl, which is as defined above, wherein a hydrogen atom is replaced by an aryl group. Examples are benzyl, phenethyl and the like.
  • C 1 -C 4 -alkylene is a linear or branched divalent alkyl radical having 1, 2, 3 or 4 carbon atoms. Examples are -CH 2 -, -CH 2 CH 2 -, -CH (CH 3 ) -, -CH 2 CH 2 CH 2 -, -CH (CH 3 ) CH 2 -, -CH 2 CH (CH 3 ) - , -C (CH 2 ) 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH (CH 3 ) CH 2 CH 2 -, -CH 2 CH 2 CH (CH 3 ) -, -C (CH 2 ) 2 CH 2 -, -CH 2 C (CHs) 2 - and -CH 2 CH 2 CH 2 CH 2 CH 2 -.
  • Linear or branched C 2 -Cs-alkylene is a linear or branched divalent alkyl radical having 2, 3, 4 or 5 carbon atoms. Examples are -CH 2 CH 2 -, -CH (CH 3 ) -, -CH 2 CH 2 CH 2 -, -CH (CH 3 ) CH 2 -, -CH 2 CH (CH 3 ) -, -C (CHs ) 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH (CH 3 ) CH 2 CH 2 -, -CH 2 CH 2 CH (CHs) -, -C (CH 2 ) 2 CH 2 -, -CH 2 C (CHs) 2 - and -CH 2 CH 2 CH 2 CH 2 CH 2 -.
  • Linear or branched C4-Cs-alkylene is a linear or branched divalent alkyl radical having 4 to 8 carbon atoms. Examples are -CH 2 CH 2 CH 2 CH 2 -, -CH (CH 3 ) CH 2 CH 2 -, -CH 2 CH 2 CH (CHs) -, -C (CH 2 ) 2 CH 2 -, -CH 2 C (CHs) 2 -, -CH 2 CH 2 CH 2 CH 2 CH 2 -, -CH 2 C (CH 2 ) 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 -, -CH 2 C (CH 2 ) 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 -, - (CH 2 ) 7 , - (CH 2 ) ⁇ - and positional isomers thereof.
  • Linear or branched C 2 -C 10 -alkylene is a linear or branched divalent alkyl radical having 2 to 10 carbon atoms.
  • Examples are, in addition to the radicals mentioned above for C 2 -C 5 -alkylene, the higher homologues having 6 to 10 carbon atoms, such as hexylene, heptylene, octylene, nonylene and decylene.
  • Linear or branched C 2 -C 2 o-alkylene is a linear or branched divalent alkyl radical having 2 to 20 carbon atoms.
  • Examples are, in addition to the radicals mentioned above for C 2 -C 8 -alkylene, the higher homologues having 6 to 20 carbon atoms, such as hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, Nonadecylene and eicosyls.
  • Alkenylene is a linear or branched aliphatic mono- or polysubstituted, for example mono- or di-unsaturated, olefinically unsaturated bivalent radical having, for example, 2 to 20 or 2 to 10 or 4 to 8 carbon atoms. When the residue contains more than one carbon-carbon double bond, they are preferably non-vicinal, ie not allenic.
  • Alkynylene is a linear or branched aliphatic divalent radical of, for example, 2 to 20 or 2 to 10 or 4 to 8 carbon atoms containing one or more, eg 1 or 2 carbon-carbon triple bonds.
  • C 6 -C 8 cycloalkylene is a divalent monocyclic saturated hydrocarbon group of 5 to 8 carbon ring members.
  • Examples are cyclopentane-1, 2-diyl, cyclopentane-1, 3-diyl, cyclohexane-1, 2-diyl, cyclohexane-1, 3-diyl, cyclohexane-1, 4-diyl, cycloheptane-1, 2-diyl, Cycloheptane-1, 3-diyl, cycloheptane-1, 4-diyl, cyclooctane-1, 2-diyl, cyclooctane-1, 3-diyl, cyclooctane-1, 4-diyl and cyclooctane-1, 5-diyl.
  • pyrrolin-1-yl pyrazolin-1-yl, imidazoline-1, bonded via N-bonded 5- or 6-membered unsaturated non-aromatic heterocycle, which may additionally contain one or two further nitrogen atoms or another sulfur atom or oxygen atom as ring member.
  • pyrrole-1-yl, pyrazol-1-yl, imidazol-1-yl and triazole-1 bonded via N which may additionally contain a further nitrogen atom as ring member, are bonded via N or 5- or 6-membered unsaturated aromatic heterocycle. yl.
  • a primary amino group is meant a radical -NH2.
  • urea and / or a urea derivative are selected below
  • R 1 R 2 NC (OO) -NR 3 R 4 substituted ureas of the formula R 1 R 2 NC (OO) -NR 3 R 4 , in which R 1 , R 2 , R 3 and R 4 are independently selected from hydrogen, C 1 -C 12 -alkyl, aryl and aryl-ci C4-alkyl, wherein at least one of the radicals R 1 , R 2 , R 3 and R 4 is not for
  • R 1 and R 2 and / or R 3 and R 4 each together are C 2 -C 8 -alkylene, where a methylene group (ie a group CH 2 in the alkylene chain) may optionally be replaced by a carbonyl group; or R 1 and R 3 together represent C 2 -C 8 -alkylene, where a methylene group
  • R 1 and R 2 and / or R 3 and R 4 each together with the nitrogen atom to which they are attached form a 5- or 6-membered unsaturated aromatic or non-aromatic ring containing one or two further nitrogen atoms or a sulfur atom or Can contain oxygen atom as a ring member (ie, R 1 and R 2 or R 3 and R 4 together with the nitrogen atom to which they are attached, for a bonded via N 5- or 6-membered unsaturated aromatic or non-aromatic ring, the or two further nitrogen atoms or a sulfur atom or oxygen atom may contain as ring member);
  • R 11 , R 12 and R 13 are independently selected from hydrogen, C 1 -C 2 -alkyl, aryl and aryl-C 1 -C 4 -alkyl, where at least one of R 9 , R 10 , R 11 , R 12 and R 13 does not stand for hydrogen; or R 9 and R 10 and / or R 12 and R 13 each hen together represent C2-Cs alkylene STE, wherein a methylene group (ie a group Chb in the alkylene chain) may be optionally replaced by a carbonyl group; or R 9 and R 12 together represent C2-Cs-alkylene, wherein a methylene group (ie a group Chb in the alkylene chain) may optionally be replaced by a carbonyl group; or R 9 and R 10 and / or R 12 and R 13 each together with the nitrogen atom to which they are attached form a 5- or 6-membered unsaturated aromatic or non-aromatic ring additionally containing another nitrogen atom, sulfur atom or
  • Cs-alkylene stand.
  • R 2 and R 4 are hydrogen and R 1 and R 3 are identical or different and are C 1 -C 12 -alkyl, aryl or aryl-C 1 -C 4 -alkyl.
  • R 1 , R 2 , R 3 and R 4 are the same and are linear Ci-C 4 -AlkVl. Examples of these are N, N, N ', N'-tetramethylurea and N, N, N', N'-tetraethylurea.
  • R 1 and R 2 and R 3 and R 4 are each in each case taken together as C 2 -C 8 -alkylene, where a methylene group (Chb) in the alkylene chain may be replaced by a carbonyl group (CO); that is, R 1 and R 2 together form a C 2 -C 8 -alkylene group, wherein a methylene group (Chb) in the alkylene chain may be replaced by a carbonyl group (CO), and R 3 and R 4 together form a C 2 -C 5 -alkylene group.
  • Cs-alkylene group, wherein a methylene group (Chb) in the alkylene chain may be replaced by a carbonyl group (CO). Examples thereof are di (tetrahydro-1H-pyrrol-1-yl) -methanone, bis (pentamethylene) urea and carbonylbis- caprolactam.
  • R 2 and R 4 are hydrogen and R 1 and R 3 together form a C 2 -C 8 -alkylene group, where a methylene group may be replaced by a carbonyl group. Examples of these are ethyleneurea and 1, 2 or 1, 3-propyleneurea.
  • R 1 and R 2 and R 3 and R 4 together with the nitrogen atom to which they are attached form an unsaturated aromatic or non-aromatic heterocycle as defined above.
  • examples of these are carbonyldipyrazole and carbonyldiimidazole.
  • R 6 and R 8 is hydrogen and R 5 and R 7 are identical or different and represent d- Ci2-alkyl, aryl or aryl-Ci-C4-alkyl.
  • R 5 and R 7 are identical or different and represent d- Ci2-alkyl, aryl or aryl-Ci-C4-alkyl.
  • R 5 and R 7 are identical or different and represent d- Ci2-alkyl, aryl or aryl-Ci-C4-alkyl.
  • R 5 and R 7 are identical or different and represent d- Ci2-alkyl, aryl or aryl-Ci-C4-alkyl. Examples of these are N, N'-dimethylthiourea, N, N'-diethylthiourea, N, N'-dipropylthiourea, N, N'-diisopropylthiourea, N, N'-di-n-butylthiourea, N, N'-di
  • R 5 , R 6 , R 7 and R 8 are the same and are linear Ci-C 4 -AlkVl. Examples of these are N, N, N ', N'-tetramethylthiourea and N, N, N', N'-tetraethylthiourea.
  • R 5 and R 6 and R 7 and R 8 each case together are C2-Cs alkylene, wherein a methylene group (CHB) in the alkylene chain may be substituted by a carbonyl group (CO) is replaced; that is, R 5 and R 6 form together form a C 2 -C 8 -alkylene group, where a methylene group (CH 2) in the alkylene chain may be replaced by a carbonyl group (CO), and R 7 and R 8 together form a C 2 -C 5 -alkylene group, where a methylene group (Chb) in the alkylene chain may be replaced by a carbonyl group (CO).
  • Examples thereof are di- (tetrahydro-1H-pyrrol-1-yl) -methanthione, bis (pentamethylene) thiourea and thiocarbonylbiscaprolactam.
  • R 6 and R 8 are hydrogen and R 5 and R 7 together form a C 2 -C 8 -alkylene group, where a methylene group may be replaced by a thiocarbonyl group.
  • Examples include ethylene thiourea and 1, 2 or 1, 3-propylene thiourea.
  • R 5 and R 6 and R 7 and R 8 together with the nitrogen atom to which they are attached form an unsaturated aromatic or non-aromatic heterocycle as defined above.
  • examples of these are thiocarbonyldipyrazole and thiocarbonyldiimidazole.
  • R 10 , R 11 and R 13 are hydrogen and R 9 and R 12 are identical or different and are C 1 -C 12 -alkyl, aryl or aryl-C 1 -C 4 -alkyl.
  • R 9 , R 10 , R 12 and R 13 are the same and are linear CrC 4 -AlkVl and R 11 is hydrogen or methyl and in particular hydrogen. Examples of these are N, N, N ', N'-tetramethylguanidine and N, N, N', N'-tetraethylguanidine.
  • R 9 and R 10 and R 12 and R 13 are each in each case taken together as C 2 -C 8 -alkylene, where a methylene group (Chb) in the alkylene chain may be replaced by a carbonyl group (CO); that is, R 9 and R 10 together form a C 2 -C 8 -alkylene group, wherein a methylene group (Chb) in the alkylene chain may be replaced by a carbonyl group (CO), and R 12 and R 13 together form a C 2 -C 5 Alkylene group, wherein a methylene group (Chb) in the alkylene chain by a carbonyl group (CO) may be replaced, and R 11 is hydrogen or methyl and especially hydrogen. Examples include
  • R 10 , R 11 and R 13 are hydrogen and R 9 and R 12 together form a C 2 -C 8 -alkylene group, where a methylene group may be replaced by a carbonyl group. Examples of these are ethylene guanidine and 1, 2 or 1, 3-Propylenguanidin.
  • An alternatively preferred embodiment forms R 9 and R 10 and R 12 and R 13 together with the nitrogen atom to which they are attached, an unsaturated aromatic or non-aromatic heterocycle as defined above and R 11 is hydrogen or methyl and especially hydrogen , Examples are iminodipyrazole and iminodiimidazole.
  • R 14 and R 15 are C 1 -C 4 -alkyl. Particularly preferably, both radicals are identical. Examples of these are dimethyl carbonate, diethyl carbonate, dipropyl carbonate, diisopropyl carbonate, di-n-butyl carbonate, di-sec-butyl carbonate, diisobutyl carbonate and di-tert-butyl carbonate. Preference is given here to dimethyl carbonate and diethyl carbonate.
  • R 14 and R 15 together are C 2 -C 6 -alkylene and preferably C 2 -C 3 -alkylene.
  • Examples of such carbonates are ethylene carbonate and 1, 2 and 1, 3-propylene carbonate.
  • the substituted ureas, thiourea, the substituted thioureas and the carbonic esters are preferred. More preferred are the substituted ureas, thiourea and the carbonic esters. Preferred among these are thiourea, N, N'-dimethylurea, N 1 N 1 -
  • urea itself is preferably used as component (i), if appropriate in combination with one of the abovementioned urea derivatives, and in particular only urea.
  • the at least one amine (iii) is preferably composed exclusively of the components (Ni.1), (iii.2) and (iii.3); that is, the proportions of these three components add up to 100 mole percent of component (iii).
  • the component (iii.1) is preferably used in an amount of 30 to 100 mol%, more preferably 50 to 100 mol%, and especially 75 to 100 mol%, based on the total amount of the components (iii. 1), (iii.2) and (iii.3).
  • Component (iii.2) is used in an amount of preferably 0 to 40 mol%, particularly preferably 0 to 30 mol% and in particular from 0 to 15 mol%, based on the total amount of components (Ni.1), (iii.2) and (iii.3).
  • the component (iii.3) is used in an amount of preferably 0 to 70 mol%, particularly preferably 0 to 50 mol% and in particular 0 to 25 mol%, based on the total amount of the components (Ni.1) , (iii.2) and (iii.3).
  • component (iii.2) when component (iii.2) is used, its amount used is preferably 1 to 50 mol%, e.g. 5 to 50 mol% or 10 to 50 mol%, particularly preferably 1 to 40 mol%, e.g. 5 to 40 mol% or 10 to 40 mol%, more preferably 1 to 30 mol%, e.g. 5 to 30 mol% or 10 to 30 mol%, and especially 1 to 15 mol%, e.g. 2 to 15 mol% or 5 to 15 mol%, based on the total amount of components (Ni.1), (iii.2) and (iii.3).
  • component (iii.3) when component (iii.3) is employed, its amount used is preferably 1 to 80 mol%, e.g. 5 to 80 mol% or 10 to 80 mol%, particularly preferably 1 to 70 mol%, e.g. 5 to 70 mol% or 10 to 70 mol%, more preferably 1 to 50 mol%, e.g. 5 to 50 mol% or 10 to 50 mol%, and especially 1 to 25 mol%, e.g. 5 to 25 mol% or 10 to 25 mol%, based on the total amount of components (Ni.1), (iii.2) and (iii.3).
  • Komponeten (Ni.1) contains exactly two primary amino groups (-NH2).
  • the component (Ni.1) is a polyamine, it contains two primary amino groups (-NH2) and also contains one or more secondary (-NHR; R other than H) and / or tertiary (-NRR '; R and R 'other than H) amino groups, eg 1 to 20 or 1 to 10 or 1 to 4 secondary and / or tertiary amino groups.
  • the component (Ni.1) is a diamine, this contains no further amino functions besides the two primary amino groups.
  • the di- or polyamine of component (Ni.1) is preferably selected from amines of the formula
  • A is a divalent aliphatic, alicyclic, aliphatic-alicyclic, aromatic or araliphatic radical, wherein the abovementioned radicals are also interrupted by a carbonyl group or by a sulfone group may be and / or may be substituted by 1, 2, 3 or 4 radicals selected from C 1 -C 4 -alkyl; or for a bivalent radical of the formula stands; wherein
  • X is O or NR a wherein R a is H, Ci -C 4 -alkyl, C 2 C 4 hydroxyalkyl or -C 4 -alkoxy, and preferably represents H, Ci-C 4 alkyl or Ci-C 4 - Alkoxy;
  • B is C 2 -C 6 alkylene
  • a is a number from 1 to 100, preferably 1 to 80 and especially 1 to 20.
  • Divalent aliphatic radicals are those which contain no cycloaliphatic, aromatic or heterocyclic constituents. Examples are alkylene, alkenylene and alkynylene radicals.
  • Divalent alicyclic radicals may be one or more, e.g. contain one or two alicyclic radicals; however, they contain no aromatic or heterocyclic constituents.
  • the alicyclic radicals may be substituted by aliphatic radicals, but both binding sites for the Nhb groups are on the alicyclic radical.
  • Divalent aliphatic-alicyclic radicals contain both at least one divalent aliphatic and at least one divalent alicyclic radical, the two binding sites for the Nhb groups either being attached to the alicyclic radical (s) or both to the aliphatic radical (s) or one on an aliphatic and the other on an alicyclic radical.
  • Divalent aromatic radicals may be one or more, e.g. contain one or two aromatic radicals; however, they contain no alicyclic or heterocyclic constituents.
  • the aromatic radicals may be substituted by aliphatic radicals, but both binding sites for the Nhb groups are located on the aromatic radical (s).
  • Divalent araliphatic radicals contain at least one divalent aliphatic as well as at least one divalent aromatic radical, the two binding sites for the Nhb groups either being attached to the aromatic element (s). may see residue (s) or both on the aliphatic residue (s) or one on an aliphatic residue and the other on an aromatic residue.
  • the bivalent aliphatic radical A is linear or branched C 2 -C 20 -alkylene, particularly preferably linear or branched C 2 -C 10 -alkylene and, in particular, linear or branched C 4 -C -alkylene.
  • Examples of suitable amines in which the radical A has this meaning are 1, 2-ethylenediamine, 1, 2- and 1, 3-propylenediamine, 2,2-dimethyl-1,3-propanediamine , 1, 4-butylenediamine, 1, 5-pentylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, undecamethylenediamine, dodecamethylenediamine, tridecamethylenediamine, tetradecemethylenediamine, pentadecamethylenediamine, hexadecamethylenediamine, heptadecamethylenediamine, octadecamethylenediamine, nonadecamethylenediamine, eicosamethylenediamine , 2-butyl-2-ethyl-1, 5-pentamethylenediamine, 2,2,4- or 2,4,4-trimethyl-1,6
  • A is linear or branched C 2 -C 10 -alkylene, such as in 1, 2-ethylenediamine, 1, 2- and 1, 3-propylenediamine, 2,2-dimethyl-1, 3-propanediamine, 1, 4-butylenediamine, 1, 5-pentylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, 2,2,4- or 2,4,4-trimethyl-1,6-hexamethylenediamine, 1, 5-diamino 2-methylpentane, 1, 4-diamino-4-methylpentane and the like.
  • amines in which A is linear or branched C 4 -C 8 -alkylene, as in 2,2-dimethyl-1, 3-propanediamine, 1, 4-butylenediamine, 1, 5-pentylenediamine, hexamethylenediamine, heptamethylenediamine, Octamethylenediamine, 1, 5-diamino-2-methylpentane, 1, 4-diamino-4-methylpentane and the like.
  • amines are used in which A is linear or branched C4-Cs-alkylene, wherein in branched alkylene at most one branch originates from one carbon atom.
  • amines examples include 1, 4-butylenediamine, 1, 5-pentylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine and 1, 5-diamino-2-methylpentane, ie the amines listed above as particularly preferred except for 2,2-dimethyl -1, 3-propanediamine and 1, 4-diamino-4-methylpentane.
  • amines are used in which A is linear C 4 -C 8 -alkylene, such as 1,4-butylenediamine, 1,5-pentylenediamine, hexamethylenediamine, heptamethylenediamine and octamethylenediamine.
  • the divalent alicyclic radicals A are selected from Cs-Cs-cycloalkylene which may carry 1, 2, 3 or 4 C 1 -C 4 -alkyl radicals.
  • suitable amines in which the radical A has this meaning are cyclopentylenediamine, such as 1,2-diaminocyclopentane or 1,3-diaminocyclopentane, cyclohexyllenediamine, such as 1,2-diaminocyclohexane, 1,3-diaminocyclohexane or 1 , 4-diaminocyclohexane, 1-methyl-2,4-diaminocyclohexane, 1-methyl-2,6-diaminocyclohexane, cycloheptylenediamine, such as 1,2-diaminocycloheptane, 1, 3
  • Diaminocycloheptane or 1,4-diaminocycloheptane, and cyclooctylenediamine such as 1,2-diaminocyclooctane, 1,3-diaminocyclooctane, 1,4-diaminocyclooctane or 1,5-diaminocyclooctane.
  • the amino groups may be cis or trans to each other.
  • the divalent aliphatic-alicyclic radicals A are selected from C 5 -C 8 -cycloalkylene-C 1 -C 4 -alkylene, C 5 -C 8 -cycloalkylene-C 1 -C 4 -alkylene-C 6 -C 8 -cycloalkylene and C 1 -C 4 -alkylene C 5 -C 8 -cycloalkylene-C 1 -C 4 -alkylene, where the cycloalkylene radicals may carry 1, 2, 3 or 4 C 1 -C 4 -alkyl radicals.
  • Suitable amines in which the radical A has the meaning are diamodicyclohexylmethane, isophoronediamine, bis (aminomethyl) cyclohexane, such as 1, 1-bis (aminomethyl) cyclohexane, 1, 2-bis (aminomethyl) cyclohexane, 1, 3-bis (aminomethyl) cyclohexane or 1,4-bis (aminomethyl) cyclohexane, 2-aminopropylcyclohexylamine, 3 (4) -aminomethyl-1-methylcyclohexylamine and the like.
  • the groups attached to the alicyclic radical can assume any relative position (cis / trans) to one another.
  • the divalent aromatic radicals A are selected from phenylene, biphenylene, naphthylene, phenylene-sulfone-phenylene and phenylene-carbonyl-phenylene, where the phenylene and naphthylene radicals can carry 1, 2, 3 or 4 C 1 -C 4 -alkyl radicals ,
  • Suitable amines in which the radical A has this meaning are phenylenediamine, such as o-, m- and p-phenylenediamine, toluenediamine, such as o-, m- and p-phenylenediamine, toluenediamine, such as o-, m- and p-phenylenediamine, toluenediamine, such as o-, m- and p-
  • Toluenediamine xylylenediamine, naphthylenediamine, such as 1, 2, 1, 3, 1, 4, 1, 5, 1, 8, 2,3, 2,6 and 2,7-naphthylene, diaminodiphenyl sulfone, such as 2,2'-, 3,3'- and 4,4'-diaminodiphenylsulfone, and diaminobenzophenone such as 2,2'-, 3,3'- and 4,4'-diaminobenzophenone.
  • diaminodiphenyl sulfone such as 2,2'-, 3,3'- and 4,4'-diaminodiphenylsulfone
  • diaminobenzophenone such as 2,2'-, 3,3'- and 4,4'-diaminobenzophenone.
  • the divalent araliphatic radicals A are selected from phenylene-C 1 -C 4 -alkylene and phenylene-C 1 -C 4 -alkylene-phenylene, where the phenylene radicals may carry 1, 2, 3 or 4 C 1 -C 4 -alkyl radicals.
  • Suitable amines in which the radical A has the meaning are diamodiphenylmethane, such as 2,2'-, 3,3'- and 4,4'-diaminodiphenylmethane, and the like.
  • X is O.
  • a is preferably a number from 2 to 100, particularly preferably from 2 to 80, more preferably from 2 to 20, even more preferably from 2 to 10 and in particular from 2 to 6.
  • amine-terminated polyoxyalkylene polyols for example Jeff amines, such as 4,9-dioxadodecane-1, 12-diamine and 4,7,10-trioxatridecan-1, 13- diamine, or more regular amine-terminated polyoxyalkylene polyols, such as amine-terminated polyethylene glycols, amine-terminated polypropylene glycols or amine-terminated polybutylene glycols.
  • the three last mentioned amines (amine-terminated polyalkylene glycols) preferably have a molecular weight of 200 to 3000 g / mol.
  • X is NR a .
  • R a is preferably H or C 1 -C 4 -alkyl, particularly preferably H or methyl and in particular H.
  • H is in particular C 2 -C 3 -alkylene, such as 1, 2-ethylene, 1, 2
  • a is preferably a number from 1 to 10, particularly preferably from 1 to 6 and in particular from 1 to 4.
  • Suitable amines in which the radical A has the meaning are diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethylene lenheptamine, heptaethyleneoctamine, octaethyleneenenamine, higher polyimines, bis (3-aminopropyl) amine, bis (3-aminopropyl) methylamine and the like.
  • Preferred diamines having two primary amino groups are those of the formula NH 2 -A-NH 2, where A is a divalent aliphatic, alicyclic, aliphatic-alicyclic, aromatic or araliphatic radical, where the abovementioned radicals may also be interrupted by a carbonyl group or by a sulfone group and / or may be substituted by 1, 2, 3 or 4 radicals which are selected from Ci-C 4 -AlkVl, and wherein the aforementioned radicals of course do not contain amino groups; or for a bivalent radical of the formula stands; wherein X is O; B is C 2 -C 6 alkylene; and a is an integer from 1 to 100, preferably 1 to 80 and especially 1 to 20.
  • Particularly preferred diamines having two primary amino groups are those of the formula NH 2 -A-NH 2, where A is a divalent aliphatic radical and preferably linear or branched C 2 -C 20 -alkylene.
  • suitable amines in which the radical A has this meaning are 1, 2-ethylenediamine, 1, 2-and 1, 3-propylenediamine, 2,2-dimethyl-1,3-propanediamine , 1, 4-butylenediamine, 1, 5-pentylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, undecamethylenediamine, dodecamethylenediamine, tridecamethylenediamine, tetradecamethylenediamine, pentadecamethylenediamine, hexadecamethylenediamine, heptadecamethylenediamine, octadecamethylenedi
  • a in the diamines having two primary amino groups is linear or branched C 2 -C 10 -alkylene.
  • suitable amines in which the radical A has this meaning are 1, 2-ethylenediamine, 1, 2 and 1, 3-propylenediamine, 2,2-dimethyl-1,3-propanediamine , 1, 4-butylenediamine, 1, 5-pentylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, 2,2,4- or 2,4,4-trimethyl-1,6-hexamethylenediamine, 1, 5-diamino 2-methylpentane, 1, 4-diamino-4-methylpentane and the like.
  • a in the diamines with two primary amino groups is linear or branched C 4 -Cs-Al kylene.
  • suitable amines in which the radical A has this meaning are 2,2-dimethyl-1,3-propanediamine, 1, 4
  • amines are used in which A is linear or branched C4-Cs-alkylene, wherein in branched alkylene at most one branch originates from one carbon atom.
  • amines examples include 1,4-butylenediamine, 1,5-pentylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine and 1,5-diamino-2-methylpentane, ie the amines except those listed above as being particularly preferred up to 2,2-dimethyl- 1, 3-propanediamine and 1, 4-diamino-4-methylpentane. More preferred among these are amines in which A is linear C 4 -C 8 -alkylene, such as in 1, 4-butylenediamine, 1, 5-pentylenediamine, hexamethylenediamine, heptamethylenediamine and octamethylenediamine. Specifically, the diamine having two primary amino groups is hexamethylenediamine.
  • a polyamine having at least three primary amino groups (component iii.2), which is different from melamine, can optionally be used in the process according to the invention.
  • This component (iii.2) contains three or more primary amino groups and may also contain one or more secondary and / or tertiary amino groups.
  • amines are 3- (2-aminoethyl) aminopropylamine, N, N-bis (3-aminopropyl) ethylenediamine, N, N-bis (3-aminopropyl) butanediamine, N, N, N'N '-Tetra- (3-aminopropyl) ethylenediamine, N, N, N'N'-tetra- (3-aminopropyl) -butylenediamine, tris (aminoethyl) amine, tris (aminopropyl) amine, tris (aminohexyl) amine, trisaminohexane , 4-aminomethyl-1, 8-octamethylenediamine, tris-aminononan or tri- or higher-functional amine-terminated polyoxyalkylene polyols (eg, Jeffamine, for example, polyetheramine T403 or polyetheramine T5000) having a molecular weight of preferably
  • tris (aminoethyl) amine tris (aminopropyl) amine and Jeffamine, such as polyetheramine T403 or polyetheramine T5000.
  • this component (iii.2) in the process according to the invention is particularly useful if a higher degree of branching of the polymers should be set than with the di- or polyamine (Ni.1) alone is possible, because polyamines with at least three primary In addition to the obligatory use of melamine (ii), amino groups open up further branching possibilities.
  • the secondary and / or tertiary amino groups contained in the polyamine (Ni.1) are less reactive than the primary amino groups and under the reaction conditions of the process according to the invention, if at all, then usually only to a small extent able to undergo condensation and thus a branch point to build. In any case, they are capable of forming branching points to a much lesser extent than component (iii.2).
  • This component is an amine having a single primary amino function and optionally one or more secondary and / or tertiary amino groups.
  • primary amines without further secondary / tertiary amino functions are compounds of the formula R-NH 2, in which R is an aliphatic, alicyclic, aliphatic-alicyclic, aromatic or araliphatic radical which of course contains no amino groups.
  • Examples of these are methylamine, ethylamine, propylamine, isopropylamine, n-butylamine, sec-butylamine, isobutylamine, tert-butylamine, pentylamine, hexylamine, ethanolamine, propanolamine, isopropanolamine, pentanolamine, (2-methoxyethyl) amine, (2-ethoxyethyl) amine, (3-methoxypropyl) amine, (3-ethoxypropyl) amine, [3- (2-ethylhexyl) propyl] amine, 2- (2-aminoethoxy) ethanol, cyclohexylamine, aminomethylcyclohexane, aniline, benzylamine and like.
  • Examples of primary amines having one or more secondary and / or tertiary amino functions are N-methylethylene-1,2-diamine, N, N-dimethylethylene-1,2-diamine, N-ethylethylene -1, 2-diamine, N, N-diethylethylene-1,2-diamine, N-methylpropylene-1,3-diamine, N, N-dimethylpropylene-1,3-diamine, N-ethylpropylene-1,3-diamine , N, N-diethylpropylene-1,3-diamine, N-methylbutylene-1,4-diamine, N, N-dimethylbutylene-1,4-diamine, N-methylpentylene-1,5-diamine, N, N-dimethylpentylene -1, 5-diamine, N-methylhexylene-1,6-diamine, N, N-dimethylhe
  • At least one melamine derivative is used in the process according to the invention as further starting material (component iv).
  • the melamine derivative is selected from benzoguanamine, substituted melamines and melamine condensates.
  • the melamine condensates are preferably selected from melam, Meiern, melon and higher condensates.
  • Melam empirical formula C ⁇ -HgNu
  • Meiern empirical formula C ⁇ H ⁇ Mio
  • Melon empirical formula C6H3N9 is also a heptazine.
  • the molar ratio of component (i) to component (N) is preferably 50: 1 to 1:50, more preferably 10: 1 to 1:10, more preferably 8: 1 to 1: 8, even more preferably 4: 1 to 1 : 8, especially 2: 1 to 1: 5 and especially 1: 1 to 1: 5.
  • the molar ratio of component (i) to component (iii) is preferably 10: 1 to 1:50, more preferably 2: 1 to 1:50, more preferably 2: 1 to 1:25, even more preferably 1: 1 to 1 : 20, especially 1: 2.5 to 1:15 and especially 1: 5 to 1:15.
  • the molar ratio of components (i) and (ii) is preferably in the ranges indicated above.
  • component (iv) is used in the process according to the invention, it preferably replaces a part of component (i). It is preferably used in amounts such that it replaces from 1 to 75 mol%, particularly preferably from 1 to 50 mol% and in particular from 1 to 25 mol% of component (i).
  • reaction of the components (i), (ii), (iii) and optionally (iv) takes place in the process according to the invention preferably in the presence of an acidic catalyst.
  • Suitable Brönsted acids are both inorganic acids, such as mineral acids, e.g. For example, hydrofluoric acid, hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid or sulfamic acid, but also ammonium salts such as ammonium fluoride, ammonium chloride, ammonium bromide or ammonium umsulfat, as well as organic acids such as methanesulfonic acid, acetic acid, trifluoroacetic acid and p-toluenesulfonic acid.
  • mineral acids e.g.
  • ammonium salts such as ammonium fluoride, ammonium chloride, ammonium bromide or ammonium umsulfat
  • organic acids such as methanesulfonic acid, acetic acid, trifluoroacetic acid and p-toluenesulfonic acid.
  • Suitable Bronsted acids are also the ammonium salts of organic amines, such as ethylamine, diethylamine, propylamine, dipropylamine, butylamine, dibutylamine, aniline, benzylamine or melamine, and also the ammonium salts of urea.
  • Suitable Lewis acids are any metal or semimetallic halides in which the metal or metalloid has an electron pair gap.
  • Examples include BF3, BCB, BBr 3, AlF 3, AlCl 3, AlBr 3, ethylaluminum dichloride, diethylaluminum chloride, TiF 4, TiCl 4, TiBr 4, VCI 5, FeF 3, FeCl 3, FeBr 3, ZnF 2, ZnCl 2, ZnBr 2, Cu (I) F, Cu (I) Cl, Cu (I) Br,
  • Bronsted acids preference is given to using Bronsted acids.
  • the reaction of the components is preferably carried out at elevated temperature.
  • the reaction temperature is preferably 40 to 300 0 C, particularly preferably 100 to 250 0 C and in particular 150 to 230 ° C.
  • the reaction can be carried out both at atmospheric pressure and at elevated pressure, for. B. at a pressure of 1 to 20 bar or 1 to 15 bar or 10 to 15 bar.
  • the pressure is often built up exclusively by the ammonia liberated in the course of the reaction in the condensation of the components (i), (ii), (iii) and optionally (iv); that is, the pressure increases with the progress of the reaction and can then be adjusted to the desired value.
  • the pressure may also be passed through an inert gas, e.g. by introducing nitrogen, argon or carbon dioxide, preferably nitrogen. This is particularly useful when the reaction is from the beginning, i. before any appreciable pressure can be produced by the ammonia formed, should be carried out under elevated pressure.
  • the reaction pressure is given in particular by the type of amines used (component iii).
  • the reaction can be carried out at atmospheric pressure when the at least one amine used has a boiling point which is above the reaction temperature.
  • the boiling point is below the reaction temperature, it is of course advantageous to carry out the reaction at elevated pressure.
  • the pressure adjustment can be carried out by discharging the ammonia, which is not required for the adjustment of the desired pressure, out of the reaction zone, for example by passing it through a pressure relief valve, which is set to the corresponding value.
  • the setting is made ment of the desired pressure via conventional control devices, for example via pressure valves.
  • the reaction can be carried out in a suitable solvent.
  • suitable solvents are inert, ie they do not react with the starting materials, intermediates or products under the given reaction conditions and are not degraded even under the given reaction conditions, for example by thermal decomposition.
  • solvents examples include chlorinated aliphatic or aromatic hydrocarbons, such as methylene chloride, chloroform, dichloroethane, trichloroethane, chlorobenzene, chlorotoluene and o-dichlorobenzene, open-chain and cyclic ethers, such as diethyl ether, dipropyl ether, tert-butyl methyl ether, tert-butyl ethyl ether, tetrahydrofuran and 1,4-dioxane, polar aprotic solvents, such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide and acetonitrile, and polar protic solvents, eg Polyols or polyether polyols, such as ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol or polyethylene glycol. Preferred solvents are the abovementioned polyo
  • the reaction is carried out in bulk, that is without additional solvent.
  • the amine (component iii) serves as a solvent, especially if it is used in excess.
  • the reaction can be carried out in such a way that all components are mixed and reacted by heating to the desired reaction temperature. Alternatively, some of the components may also be added first and the remaining ingredients gradually added, the order of addition being of minor importance. However, since melamine is usually the most difficult to dissolve component, it has proven useful in practice, the other components, that is component (i), component (iii), optionally component (iv), optionally the acidic catalyst and optionally the Solvent, undeventuell also present a portion of the melamine, bring to the desired reaction temperature and the remaining melamine gradually fed continuously or in portions.
  • component (i) in particular when it is urea, not fully present, but gradually fed continuously or in portions.
  • the addition of the individual reactants takes place in such a way that their complete dissolution is ensured so that their conversion in the condensation reaction is as complete as possible.
  • the reaction is generally carried out in reaction vessels customary for such condensation reactions, for example in heatable stirred reactors, stirred pressure vessels or stirred autoclave.
  • the reaction mixture is usually allowed to react until a desired maximum viscosity is reached.
  • the viscosity can be determined by sampling and determination by conventional methods, for example with a viscometer; However, it often appears optically in the course of the reaction when the viscosity increases greatly, for example as a result of foaming of the reaction mixture.
  • the reaction is terminated when the reaction mixture has a viscosity of at most 100,000 mPas, for example from 250 to 100,000 mPas, or from 500 to 100,000 mPas, or preferably from 750 to 100,000 mPas (at 100 0 C) special, DERS preferably of at most 50,000 mPas, for example from 250 to 50,000 mPas or from 500 to 50,000 mPas or preferably from 750 to 50,000 mPas (at 100 ° C.), and in particular not more than 10,000 mPas, for example from 250 to 10,000 mPas or from 500 to 10,000 mPas or preferably 750 to 10,000 mPas (at 100 ° C).
  • the reaction is preferably stopped by lowering the temperature, preferably by lowering the temperature to ⁇ 100 °, z. B. 20 to ⁇ 100 °, preferably to ⁇ 50 0 C, z. B. to 20 to ⁇ 50 0 C.
  • the workup / purification can be carried out by conventional methods, for example by deactivating or removing the catalyst and / or by removing solvent and unreacted educts.
  • the reaction product obtained can be treated, for example, with a base, for example with sodium hydroxide solution or potassium hydroxide solution.
  • the precipitated salts are advantageously subsequently removed, for example by filtration. If the viscosity of the product is very high, for example more than 5000 mPa.s (at 25 ° C), this processing can take place at elevated temperature, for example at least 50 0 C, or at least 75 0 C, or at least 100 0 C. Alternatively, or additionally, the filtration can be carried out under reduced pressure. For many applications, however, the degree of purity of the polycondensate obtained is sufficient, so that no further work-up or purification must be carried out and the product can be fed directly to its further intended use.
  • the products obtained by the process according to the invention are highly branched and essentially non-crosslinked.
  • Highly branched polymers in the context of the present invention are understood to be macromolecules which are structurally as well as molecularly nonuniform. Depending on the reaction, you can on the one hand, starting from a central molecule analogous to dendrimers, but with uneven chain length of the branches, be constructed. On the other hand, they can also start from linear molecules and be built up with branched functional side groups. "Highly branched” in the context of the present invention also means that the degree of branching (DB) is 10 to 99.9%, preferably 20 to 99% and in particular from 20 to 95%.
  • DB degree of branching
  • the degree of branching is the mean number of dendritic linkages plus the average number of end groups per molecule divided by the sum of the average number of dendritic links, the average number of linear links, and the average number of endpoints multiplied by 100.
  • dendritic is understood in this context that the degree of branching at this point in the molecule is 99.9 to 100%.
  • degree of branching see also H. Frey et al., Acta. Polym. 1997, 48, 30.
  • substantially non-crosslinked or “uncrosslinked” in the sense of the present invention means that a degree of crosslinking of less than 15 wt .-%, preferably less than 10 wt .-% is present, wherein the degree of crosslinking over the insoluble portion of the polymer is determined.
  • the insoluble portion of the polymer is, for example, by extraction for 4 hours with the same solvent as used for gel permeation chromatography (GPC), that is, preferably dimethylacetamide or hexafluoroisopropanol, depending on the solvent in which the polymer is more soluble Soxhlet apparatus and, after drying the residue to constant weight, weighing the remaining residue determined.
  • GPC gel permeation chromatography
  • the polymers obtained by the process according to the invention have a number average molecular weight M n of preferably 500 to 200,000, particularly preferably from 500 to 100,000 and in particular from 500 to 50,000 g / mol.
  • the weight-average molecular weight M w is preferably at most 750,000, particularly preferably at most 500,000, more preferably at most 100,000 and in particular at most 75,000.
  • the polydispersity (PD quotient of M w and M n ) is preferably at least 1, 1, more preferably at least 1, 5 and in particular at least 2.
  • the molecular weights (M n , M w ) and polydispersity given in the context of the present invention refer to values which are obtained by gel permeation chromatography (GPC) in hexafluoroisopropanol as solvent with PMMA calibration.
  • Another object of the invention are highly branched urea-melamine polymers, which are obtainable by the method according to the invention.
  • the above statements on the polymers obtainable by the process according to the invention are hereby incorporated by reference.
  • the invention relates to the use of the polymers of the invention as adhesion promoters, thixotropic additives, rheology additives, solubilizers (solubilizers), for the surface modification of organic or inorganic material or as building blocks for the production of paints, coatings, adhesives, sealants, casting elastomers or foams.
  • Interfaces are surfaces that separate two miscible phases (gas-liquid, gas-solid, liquid-solid, liquid-liquid, solid-solid). These include the adhesive, adhesive or density effect, the flexibility, scratch or break resistance, wettability or wetting ability, sliding property, frictional force, corrodibility, dyeability, printability or gas permeability, etc. of the application media.
  • the use of the polymers according to the invention is for the surface modification of organic materials.
  • organic materials are plastics, especially in the form of plastic films, cellulose, for example in the form of paper or cardboard, textiles made of natural or synthetic fibers, leather, wood, mineral oil products, etc.
  • suitable inorganic materials are inorganic pigments, metal, glass and basic inorganic materials such as cement, gypsum or calcium carbonate.

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Abstract

La présente invention concerne un procédé de fabrication de polymères urée-mélamine hautement ramifiés, selon lequel de l'urée ou un dérivé d'urée, de la mélamine et au moins une amine sont condensés. Selon l'invention, la ou les amines comprennent une diamine ou une polyamine contenant deux groupes amino primaires. L'invention concerne également les polymères urée-mélamine hautement ramifiés qui peuvent être obtenus par le procédé selon l'invention, ainsi que leur utilisation en tant qu'adhésifs, additifs thixotropes, additifs rhéologiques, agents de solubilisation, en tant qu'agents de modification de surfaces ou en tant que constituants pour la fabrication de laques, de revêtements, d'adhésifs, de matériaux d'étanchéité, d'élastomères coulables ou de mousses.
PCT/EP2008/068098 2007-12-20 2008-12-19 Polymères urée-mélamine hyperramifiés WO2009080787A1 (fr)

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WO2011073246A1 (fr) 2009-12-16 2011-06-23 Basf Se Polymères mélamine-polyamine hautement ramifiés fonctionnalisés
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WO2011107365A1 (fr) 2010-03-04 2011-09-09 Basf Se Matériaux lignocellulosiques ayant de bonnes propriétés mécaniques
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US8623501B2 (en) 2010-03-04 2014-01-07 Basf Se Lignocellulose materials having good mechanical properties
US8466221B2 (en) 2010-03-09 2013-06-18 Basf Se Polyamides that resist heat-aging
CN102791798A (zh) * 2010-03-09 2012-11-21 巴斯夫欧洲公司 耐热老化性聚酰胺
CN102791798B (zh) * 2010-03-09 2015-09-09 巴斯夫欧洲公司 耐热老化性聚酰胺
WO2011110508A1 (fr) 2010-03-09 2011-09-15 Basf Se Polyamides résistant au vieillissement thermique
WO2011141266A1 (fr) 2010-04-15 2011-11-17 Basf Se Procédé de fabrication de mousses de polyuréthane ignifugées
DE102011079112A1 (de) 2010-08-09 2013-01-03 Basf Se Wässrige Beschichtungsformulierung
WO2013021039A1 (fr) 2011-08-11 2013-02-14 Basf Se Composition absorbant les microondes
EP3127950A1 (fr) 2015-08-03 2017-02-08 Basf Se Composition de résines amino nanoporeux pour l'aborption-désorption de gaz acide
CN107935441A (zh) * 2017-10-16 2018-04-20 广东盛瑞科技股份有限公司 一种醚醇类复合发泡剂及其制备方法
CN113980269A (zh) * 2021-07-22 2022-01-28 西南林业大学 三聚氰胺-二胺或多胺-尿素三元共缩聚热固型树脂及其制备方法和应用

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