CN112004853A - Aqueous composition containing uretdione groups and process for its preparation - Google Patents

Aqueous composition containing uretdione groups and process for its preparation Download PDF

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Publication number
CN112004853A
CN112004853A CN201980021604.5A CN201980021604A CN112004853A CN 112004853 A CN112004853 A CN 112004853A CN 201980021604 A CN201980021604 A CN 201980021604A CN 112004853 A CN112004853 A CN 112004853A
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CN
China
Prior art keywords
diisocyanate
polyol
groups
uretdione
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201980021604.5A
Other languages
Chinese (zh)
Other versions
CN112004853B (en
Inventor
D·格雷茨塔-弗兰茨
S·博伊克
S·德尔
H-J·拉斯
N·尤瓦
H-D·格维斯
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Covestro Deutschland AG
Covestro LLC
Original Assignee
Covestro Intellectual Property GmbH and Co KG
Covestro LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US15/933,470 external-priority patent/US11292864B2/en
Priority claimed from US15/933,487 external-priority patent/US20190292305A1/en
Priority claimed from US15/933,507 external-priority patent/US20190292294A1/en
Priority claimed from US15/933,475 external-priority patent/US11008416B2/en
Priority claimed from US15/933,495 external-priority patent/US11312881B2/en
Priority claimed from EP18163620.0A external-priority patent/EP3543269A1/en
Priority claimed from US15/933,511 external-priority patent/US11440988B2/en
Priority claimed from EP18163625.9A external-priority patent/EP3543271A1/en
Priority claimed from US15/933,570 external-priority patent/US10731051B2/en
Priority claimed from EP18163621.8A external-priority patent/EP3543270A1/en
Priority claimed from US15/933,553 external-priority patent/US10633477B2/en
Priority claimed from US15/933,527 external-priority patent/US20190292296A1/en
Priority claimed from US15/933,500 external-priority patent/US10696775B2/en
Priority claimed from EP18181876.6A external-priority patent/EP3590987A1/en
Priority claimed from EP18181877.4A external-priority patent/EP3590988A1/en
Application filed by Covestro Intellectual Property GmbH and Co KG, Covestro LLC filed Critical Covestro Intellectual Property GmbH and Co KG
Publication of CN112004853A publication Critical patent/CN112004853A/en
Publication of CN112004853B publication Critical patent/CN112004853B/en
Application granted granted Critical
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    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
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    • C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
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    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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    • C08G18/2036—Heterocyclic amines; Salts thereof containing one heterocyclic ring having at least three nitrogen atoms in the ring
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Abstract

The invention relates to aqueous uretdione group-containing compositions comprising or consisting of (A) at least one uretdione group-containing curing agent based on aliphatic, cycloaliphatic, araliphatic and/or aromatic polyisocyanates, which does not comprise chemically bonded hydrophilicizing groups; (B) at least one non-ionically hydrophilicized hydroxyl-containing polyol; (C) optionally a solvent; and (D) optionally auxiliaries and additives; wherein the amount ratio of components (A) and (B) is such that the molar ratio of NCO groups of curing agent (A) present as uretdiones to NCO-reactive groups of polyol (B) is from 3:0.5 to 0.5:3, and wherein A and B are present as a physical mixture. Furthermore, the present invention relates to a process for preparing a polyurethane layer using the aqueous uretdione group-containing composition of the invention, to a polyurethane layer obtained by this process, and to substrates coated or bonded with the polyurethane layer.

Description

Aqueous composition containing uretdione groups and process for its preparation
The invention relates to aqueous compositions containing uretdione groups, comprising or consisting of
(A) At least one uretdione group-containing curing agent based on aliphatic, cycloaliphatic, araliphatic and/or aromatic polyisocyanates, which does not contain chemically bonded hydrophilicizing groups;
(B) at least one non-ionically hydrophilicized hydroxyl-containing polyol;
(C) optionally a solvent; and
(D) optional auxiliaries and additives;
wherein the amount ratio of components (A) and (B) is such that the molar ratio of NCO groups of curing agent (A) present as uretdiones to NCO-reactive groups of polyol (B) is from 3:0.5 to 0.5:3, and wherein A and B are present as a physical mixture.
Furthermore, the present invention relates to a process for preparing a polyurethane layer using the aqueous uretdione group-containing composition of the invention, to a polyurethane layer obtained by this process, and to substrates coated or bonded with the polyurethane layer.
In recent years, the importance of aqueous paints and coating agents has increased dramatically due to increasingly stringent emission guidelines for solvents released when applying paints. Although there are aqueous lacquer systems available today for many fields of application, they often do not achieve the high quality levels of conventional solvent-containing lacquers in terms of solvent and chemical resistance or elasticity and mechanical load. In particular, up to now, no aqueous processable polyurethane-based coating agents are known which sufficiently meet the high requirements in practice. This statement applies both to DE 4001783A1, which is directed to specific anionically modified aliphatic polyisocyanates, and to systems of DE 2456469A1, DE 2814815A1, EP 0012348A1 and EP 0424697A1, which describe aqueous one-component stoving binders based on blocked polyisocyanates and organic polyhydroxyl compounds.
In recent years, further improvements to one-component stoving binders based on blocked polyisocyanates have been achieved, as described, for example, in EP 0576952A.
The one-component stoving varnish adhesives described above and corresponding to the prior art and based on blocked polyisocyanates have the disadvantage that, even if they are substantially solvent-free, the respective blocking agents are released during the baking of such lacquer adhesives, which in turn leads to emissions. There is therefore a long-felt need in the market place to develop aqueous, emission-free one-component stoving binders. There is no lack of attempts to prepare such stoving binders based on uretdione-containing polyisocyanates without dissociates (abspalters).
According to EP 1687354a1, uretdione-containing aqueous dispersion coatings can be prepared by combining a solid uretdione compound with a molten water-dispersible resin, if desired salifying the water-dispersible resin, and dispersing the resin mixture in water. The molten water-dispersible resin may have a functional group reactive with the uretdione compound, or the coating composition may contain another water-dispersible resin having a functional group reactive with the uretdione compound. However, in the examples, an epoxy resin was used. It is generally known that epoxy paints are inferior to polyurethane paints in most properties. According to EP 1687354A1, the use of further emulsifiers is also required for the preparation of these dispersion coatings, which further impairs the lacquer properties of the dispersion coatings. Furthermore, the preparation process described in EP 1687354a1 is associated with a very high thermal load for the uretdione groups, which in practice most probably leads to a loss of uretdione groups. Furthermore, the dispersions described in EP 1687354a1 are applied directly after preparation. Information on the stability of these dispersions is lacking in EP 1687354a 1.
US 2015232609a1 discloses hydrophilic uretdione-containing polyisocyanates which are dispersible in water and are obtainable by reaction of prepolymers carrying uretdione groups with emulsifiers containing ionizable groups having a pKa value > 8 or pKb > 8 in water at room temperature. Such uretdione-containing reaction products exhibit an improved storage stability of 8 weeks at room temperature, but this is still insufficient for practical use in industry, where long-distance transport often has to be taken into account.
The above problems are surprisingly solved by using a physical mixture of a specific curing agent of the present invention and a polyol. In particular, dispersions having improved storage stability compared to compositions known in the prior art can be obtained.
The invention relates in particular to:
1. aqueous compositions containing uretdione groups, comprising or consisting of
(A) At least one uretdione group-containing curing agent based on aliphatic, cycloaliphatic, araliphatic and/or aromatic polyisocyanates, preferably based on aliphatic, cycloaliphatic and/or araliphatic polyisocyanates, particularly preferably based on aliphatic and/or cycloaliphatic polyisocyanates, which does not contain chemically bonded hydrophilicizing groups;
(B) at least one non-ionically hydrophilicized hydroxyl-containing polyol;
(C) optionally a solvent; and
(D) optional auxiliaries and additives;
wherein the quantitative ratios of components (A) and (B) are metered such that the molar ratio of NCO groups of curing agent (A) present as uretdiones to NCO-reactive groups of polyol (B) is from 3.0:0.5 to 0.5:3.0, preferably from 2.5:1.0 to 1.0:2.5, particularly preferably from 2.0:1.0 to 1.0:2.0, and wherein (A) and (B) are present as a physical mixture.
2. The aqueous composition containing a uretdione group according to aspect 1, characterized in that,
the at least one uretdione group-containing curing agent (a) is obtained by reaction of a monomeric isocyanate comprising or consisting of at least one monomeric isocyanate selected from: tetramethylene diisocyanate, cyclohexane-1, 3-diisocyanate and cyclohexane-1, 4-diisocyanate, pentamethylene diisocyanate, Hexamethylene Diisocyanate (HDI), 1-isocyanato-3, 3, 5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI), dicyclohexylmethane-2, 4 '-diisocyanate and/or dicyclohexylmethane-4, 4' -diisocyanate, tetramethylxylylene diisocyanate (TMXDI), triisocyanatononane, Tolylene Diisocyanate (TDI), diphenylmethane-2, 4 '-diisocyanate and/or diphenylmethane-4, 4' -diisocyanate (MDI), triphenylmethane-4, 4' -diisocyanate or naphthalene-1, 5-diisocyanate or mixtures thereof, preferably selected from isophorone diisocyanate, dicyclohexylmethane-2, 4' -diisocyanate and/or dicyclohexylmethane-4, 4' -diisocyanate or hexamethylene diisocyanate.
3. The aqueous composition containing a uretdione group according to aspect 1 or 2, characterized in that,
hydroxyl group-containing monomers and/or polymers are used as starting materials for the at least one uretdione group-containing curing agent (A).
4. The aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that,
the at least one uretdione group-containing curing agent (A) has a free NCO content of less than 5% by weight and a uretdione group content of from 1 to 18% by weight,as C2N2O2The molecular weight was calculated to be 84 g/mol.
5. The aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that,
the acid number of the aqueous composition is from 1 to 100 mg KOH/g, preferably from 1 to 50 mg KOH/g, particularly preferably from 1 to 5 mg KOH/g, preferably measured according to DIN EN ISO 2114:2002-06 with acetone and ethanol in a weight ratio of 2:1 as solvents and calculated on the basis of the solids content.
6. The aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that,
the at least one nonionically hydrophilicized hydroxyl-containing polyol (B) is obtained by reaction of the following components
A1) At least one polyisocyanate,
A2) at least one polyalkoxy ether derivative containing at least one-OH group, and
A3) optionally at least one polyol different from A2,
preferably in the presence of a catalyst, to obtain at least one non-ionically hydrophilized hydroxyl group-containing polyol (B); wherein the acid number of the polyol (B) is preferably up to 5 mg KOH/g, in accordance with DIN EN ISO 2114:2002-06, the weight ratio of 2:1 as solvents and calculated based on solids content.
7. The aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that,
the at least one hydroxyl group-containing polyol (B) has an OH content of more than 1% by weight-a molecular weight of 17 g/mol-and/or a number-average molecular weight Mn of from 500 to 20000 g/mol, calculated as OH groups on a solids content basis.
8. The aqueous uretdione dispersion according to one of the preceding aspects, characterized in that,
the solvent is selected from the group consisting of acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, heavy benzenes such as commercially available Solvesso 100 or Solvesso 150, propylene glycol mono-n-butyl ether, dipropylene glycol dimethyl ether, methoxypropyl acetate, diesters or mixtures thereof.
9. The aqueous uretdione dispersion according to one of the preceding aspects, characterized in that,
the auxiliaries and additives are selected from levelling agents, such as silicone polymers (polysilicones) or acrylates, photoprotectors, such as sterically hindered amines, catalysts, such as tin (II) 2-ethylhexanoate or dibutyltin dilaurate, fillers, and pigments, such as titanium dioxide, or mixtures thereof.
10. The aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that,
(A) the sum of the proportions by weight of (A), (B) and (D) being from 30 to 60% by weight, based on the solids content of the entire aqueous composition.
11. Method for producing a polyurethane layer, comprising the following steps
i) Providing an aqueous composition containing uretdione groups according to one of aspects 1 to 10;
ii) applying the mixture obtained in i) to a substrate;
iii) drying the mixture from step ii), and
iv) heating to 40 ℃ to 180 ℃ for up to 180 minutes to cure the mixture from step iii).
12. The method according to aspect 11, characterized in that the uretdione group-containing aqueous composition is obtained by mixing the uretdione group-containing curing agent (a) with the at least one polyol (B) in the absence of water, followed by dispersing with water.
13. Polyurethane layer, in particular a polyurethane film, obtainable by the process according to aspect 11 or 12.
14. A substrate coated or bonded with a polyurethane layer according to aspect 13.
Unless otherwise specifically stated, the molecular weight in the present invention is determined by means of GPC (gel permeation chromatography) using polystyrene standards. According to the invention, the average molecular weight is defined as the number average molecular weight Mn. Mn is measured in tetrahydrofuran as solvent at 23 ℃. The measurement was carried out in accordance with DIN 55672-1:2007-08 "gel permeation chromatography with part 1-tetrahydrofuran as eluent" using SECURITY GPC-system of PSS Polymer Service at a flow rate of 0.6 ml/min.
Unless explicitly stated otherwise, the weight percents in the present invention are based on the total weight of the respective system or the total weight of the respective component. For example, a copolymer may comprise a particular monomer given in weight percent, in which case the weight percent will be based on the total weight of the copolymer.
Unless otherwise specifically stated, the expression "at least one" refers to a species of compound, rather than a single molecule. For example, at least one copolymer is understood to mean a copolymer comprising at least one species, but which is contained in the composition in any number of molecules. Thus, it is also possible that two or more kinds of copolymers, each in any number if not in defined amounts, are present.
In a preferred embodiment, the aqueous uretdione group-containing composition is substantially free of other coemulsifiers (other than component (B)). The term "substantially free" is defined according to the invention in such a way that the proportion of the respective compound comprised is preferably less than 1% by weight, more preferably less than 0.25% by weight, even more preferably less than 0.1% by weight, most preferably less than 0.01% by weight, or completely absent, each based on the total weight of the uretdione group-containing aqueous composition.
The aqueous uretdione group-containing composition of the invention is preferably a polyurethane-based composition.
Polyisocyanates containing uretdione groups which are suitable as starting compounds for component (a) are polyisocyanates containing at least one isocyanate group and at least one uretdione group. They are prepared by reaction of suitable starting isocyanates (a 1), as described, for example, in WO 02/92657A 1 or WO 2004/005364A 1. In this case, a portion of the isocyanate groups are converted into uretdione groups under catalytic action, for example using triazolate or 4-Dimethylaminopyridine (DMAP) as catalyst. Examples of isocyanates (a 1) for the construction of uretdione-containing structural units are tetramethylene diisocyanate, cyclohexane-1, 3-diisocyanate and cyclohexane-1, 4-diisocyanate, pentamethylene diisocyanate, Hexamethylene Diisocyanate (HDI), 1-isocyanato-3, 3, 5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate IPDI), dicyclohexylmethane-2, 4' -diisocyanate and/or dicyclohexylmethane-4, 4' -diisocyanate, tetramethylxylylene diisocyanate (TMXDI), triisocyanatononane, Tolylene Diisocyanate (TDI), diphenylmethane-2, 4' -diisocyanate and/or diphenylmethane-4, 4 '-diisocyanate (MDI), triphenylmethane-4, 4' -diisocyanate or naphthalene-1, 5-diisocyanate, and also any mixtures of such isocyanates. Preference is given to isophorone diisocyanate, dicyclohexylmethane-2, 4 '-diisocyanate and/or dicyclohexylmethane-4, 4' -diisocyanate or hexamethylene diisocyanate.
In addition to the isocyanate groups and uretdione groups, component (a) may also have isocyanurate structures, biuret structures, allophanate structures, urethane structures and/or urea structures.
The conversion of these polyisocyanates carrying uretdione groups into curing agents (A) having uretdione groups comprises the reaction of the free NCO groups of the abovementioned polyisocyanates with a polyol component (b 1), optionally together with the use of a polyol component (b 2).
The polyol component (b 1) preferably has a hydroxyl functionality of 2 or more and a molecular weight Mn of from 62 to 500 g/mol, preferably from 62 to 400 g/mol, particularly preferably from 62 to 300 g/mol. The polyol component (b 1) preferably comprises a 2-to 6-membered polyol component having a molecular weight Mn of from 62 to 500 g/mol, preferably from 62 to 400 g/mol, particularly preferably from 62 to 300 g/mol. Preferred polyol components (b 1) are, for example, 1, 4-butanediol and/or 1, 3-butanediol, 1, 6-hexanediol, 2,2, 4-trimethyl-1, 3-pentanediol, trimethylolpropane, polyester polyols and/or polyether polyols having an average molecular weight Mn of less than or equal to 500 g/mol.
Suitable linear difunctional polyols (b 2) are selected from polyethers, polyesters, polycaprolactone diols and/or polycarbonates. The polyol component (b 2) preferably comprises at least one diol which contains ester groups and has a molecular weight Mn of from 350 to 4000 g/mol, preferably from 350 to 2000 g/mol, particularly preferably from 350 to 1000 g/mol. This is the average molecular weight which can be calculated from the hydroxyl number. Ester diols are generally mixtures in which individual components having molecular weights below or above these limits may also be present in minor amounts. These are the polyester diols known per se which are built up from diols and dicarboxylic acids.
Suitable diols are, for example, 1, 4-dimethylolcyclohexane, 1, 4-butanediol or 1, 3-butanediol, 1, 6-hexanediol, neopentyl glycol, 2,2, 4-trimethyl-1, 3-pentanediol, trimethylolpropane and pentaerythritol, or mixtures of these diols. Suitable dicarboxylic acids are, for example, aromatic dicarboxylic acids, such as phthalic acid, isophthalic acid and terephthalic acid; alicyclic dicarboxylic acids such as hexahydrophthalic acid, tetrahydrophthalic acid; endomethylenetetrahydrophthalic acid or anhydride thereof; and aliphatic dicarboxylic acids, which are preferably used, such as succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid and sebacic acid or anhydrides thereof.
Polyester diols based on adipic acid, phthalic acid, isophthalic acid and tetrahydrophthalic acid are preferably used as component (b 2). Preferred diols are, for example, 1, 4-butanediol or 1, 3-butanediol, 1, 6-hexanediol or trimethylolpropane and mixtures thereof.
Likewise preferred as component (b 2) is a polycaprolactone diol having an average molecular weight of from 350 to 4000 g/mol, preferably from 350 to 2000 g/mol, particularly preferably from 350 to 1000 g/mol, which is prepared in a manner known per se from a diol or diol mixture of the type mentioned by way of example above as starter and a lactone, such as β -propiolactone, γ -butyrolactone, γ -and-valerolactone, caprolactone, 3,5, 5-and 3,3, 5-trimethylcaprolactone, or any mixture of these lactones. Particularly preferred are such polycaprolactone diols prepared by polymerization of caprolactone.
As linear polyol component (b 2), it is also possible to use (co) polyethers made of ethylene oxide, propylene oxide and/or tetrahydrofuran, which are composed of less than 30 mol% of ethylene oxide units. Preference is given to polyethers having an average molecular weight Mn of from 500 to 2000 g/mol, such as polypropylene oxide or polytetrahydrofuran diol.
Suitable as (b 2) are also hydroxyl-containing polycarbonates, preferably with average molecular weights Mn of 400 to 4000 g/mol, preferably 400 to 2000 g/mol, such as hexanediol polycarbonates and polyester carbonates.
It is also possible to use, as polyol component (b 2) in the preparation of curing agents (A) having uretdione groups, diols having low molecular weight ester groups, the average molecular weight of which, as calculated from the functionality and the hydroxyl number, is from 134 to 349 g/mol, preferably from 176 to 349 g/mol. These are, for example, diols known per se having ester groups or mixtures of these diols, which can be prepared, for example, by reaction of the alcohols with substoichiometric amounts of dicarboxylic acids, of the corresponding dicarboxylic anhydrides, of the corresponding dicarboxylic esters of lower alcohols or of lactones. Examples of suitable acids are succinic acid, adipic acid, sebacic acid, phthalic acid, isophthalic acid, phthalic anhydride, tetrahydrophthalic acid, maleic anhydride, dimethyl terephthalate and diethylene terephthalate. Suitable lactones for preparing these ester diols are, for example, β -propiolactone, γ -butyrolactone, γ -and-valerolactone, caprolactone, 3,5, 5-and 3,3, 5-trimethylcaprolactone or any mixtures of these lactones.
Amino-functional compounds can also be used in the preparation of the curing agents (A) having uretdione groups. Examples of suitable low molecular weight amino-functional compounds are aliphatic and cycloaliphatic amines and aminoalcohols having primary and/or secondary bonded amino groups, such as cyclohexylamine, 2-methyl-1, 5-pentanediamine, diethanolamine, monoethanolamine, propylamine, butylamine, dibutylamine, hexylamine, monoisopropanolamine, diisopropanolamine, ethylenediamine, 1, 3-diaminopropane, 1, 4-diaminobutane, isophoronediamine, diethylenetriamine, ethanolamine, aminoethyl-ethanolamine, diaminocyclohexane, hexamethylenediamine, methyliminodipropylamine, iminodipropylamine, bis (aminopropyl) piperazine, aminoethylpiperazine, 1, 2-diaminocyclohexane, triethylenetetramine, tetraethylenepentamine, bis (4-aminocyclohexyl) methane, bis (4-amino-3-methylcyclohexyl) methane, bis (4-amino-3, 5-dimethylcyclohexyl) methane, bis (4-amino-2, 3, 5-trimethylcyclohexyl) methane, 1, 1-bis (4-aminocyclohexyl) propane, 2, 2-bis (4-aminocyclohexyl) propane, 1, 1-bis (4-aminocyclohexyl) ethane, 1, 1-bis (4-aminocyclohexyl) butane, 2, 2-bis (4-aminocyclohexyl) butane, 1, 1-bis (4-amino-3-methylcyclohexyl) ethane, 2, 2-bis (4-amino-3-methylcyclohexyl) propane, 1, 1-bis (4-amino-3, 5-dimethylcyclohexyl) ethane, 2, 2-bis (4-amino-3, 5-dimethylcyclohexyl) propane, 2, 2-bis (4-amino-3, 5-dimethylcyclohexyl) butane, 2, 4-diaminodicyclohexylmethane, 4-aminocyclohexyl-4-amino-3-methylcyclohexylmethane, 4-amino-3, 5-dimethylcyclohexyl-4-amino-3-methylcyclohexylmethane and 2- (4-aminocyclohexyl) -2- (4-amino-3-methylcyclohexyl) methane.
A solvent may optionally be used in the preparation of the curing agent (A) having a uretdione group. Suitable solvents for the curing agents (A) having uretdione groups are all liquid substances which do not react with the other contents, for example acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, heavy benzenes, such as the commercially available Solvesso 100 and Solvesso 150, propylene glycol mono-n-butyl ether, dipropylene glycol dimethyl ether, methoxypropyl acetate, diesters or mixtures thereof.
The curing agents (A) having uretdione groups are substantially free of ionic or nonionic chemically bonded hydrophilicizing compounds. Ionic hydrophilicizing groups are understood by those skilled in the art to mean groups which are capable of forming anions or cations. Groups capable of forming anions or cations are those which can be converted into anionic or cationic groups by chemical reaction, in particular by neutralization.
The curing agent (A) having uretdione groups is preferably free of carboxyl group-containing polyols or diols capable of forming anions, for example dihydroxycarboxylic acids, such as alpha, alpha-dihydroxyalkyl alkanoic acids, in particular alpha, alpha-dimethylol alkanoic acids, such as 2, 2-dimethylol acetic acid, 2, 2-dimethylol propionic acid, 2, 2-dimethylol butyric acid, 2, 2-dimethylol valeric acid, dihydroxysuccinic acid or polyhydroxy acids, such as gluconic acid. In addition, the curing agent (A) having a uretdione group is preferably free of an amino group-containing compound capable of forming an anion, such as α, Ω -diaminopentanoic acid or 2, 4-diaminotoluene sulfonic acid. The curing agent (A) having a uretdione group is likewise preferably free of sulfonic acid groups capable of anion formation.
Furthermore, the curing agent (a) having a uretdione group is preferably free of compounds capable of forming cations selected from tertiary amino compounds or ammonium compounds, such as tris (hydroxyalkyl) amines, N '-bis (hydroxyalkyl) alkylamines, N-hydroxyalkyldialkylamines, triaminoalkylamines, N' -bisaminoalkylamines, N-aminoalkyldialkylamines and mixtures thereof.
The curing agents (a) having uretdione groups are furthermore preferably free of nonionically hydrophilicizing compounds, such as polyalkylene oxide polyether alcohols or polyalkylene oxide polyether amines. In particular, the curing agents (A) having uretdione groups preferably contain no polyethylene oxide polyethers or mixed polyalkylene oxide polyethers, the alkylene oxide units of which consist at least 30 mol% of ethylene oxide units.
Preferred curing agents (A) having uretdione groups have a free NCO content of less than 5% by weight and an uretdione group content of from 1 to 18% by weight (as C)2N2O2Calculated, molecular weight 84 g/mol). In addition to uretdione groups, the curing agents (A) may also have isocyanurate-, biuret-, allophanate-, urethane-and/or urea structures.
The composition likewise comprises at least one polyol (component (B)).
The polyols can be obtained here by reacting polyisocyanates (a 1) with component (a 2), optionally with the use of a polyol component (A3).
Examples of suitable polyisocyanates (A1) are tetramethylene diisocyanate, cyclohexane-1, 3-diisocyanate and cyclohexane-1, 4-diisocyanate, pentamethylene diisocyanate, Hexamethylene Diisocyanate (HDI), 1-isocyanato-3, 3, 5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI), dicyclohexylmethane-2, 4' -diisocyanate and/or dicyclohexylmethane-4, 4' -diisocyanate, tetramethylxylylene diisocyanate (TMXDI), triisocyanatononane, Tolylene Diisocyanate (TDI), diphenylmethane-2, 4' -diisocyanate and/or diphenylmethane-4, 4 '-diisocyanate (MDI), triphenylmethane-4, 4' -diisocyanate or naphthalene-1, 5-diisocyanate, and also any mixtures of such isocyanates. Preference is given to isophorone diisocyanate, dicyclohexylmethane-2, 4 '-diisocyanate and/or dicyclohexylmethane-4, 4' -diisocyanate or hexamethylene diisocyanate.
In addition to the isocyanate groups, component (a 1) may also have isocyanurate-, biuret-, allophanate-, urethane-and/or urea structures.
A2 is a polyalkoxy ether derivative having at least one, preferably two-OH groups, more preferably a compound of formula (I):
Figure 603649DEST_PATH_IMAGE001
wherein
X is H or alkyl, preferably H or C1-20Alkyl, more preferably H or C2-10An alkyl group;
r is C1-4An alkylene group;
p is an integer from 2 to 50;
in each cell p
n is independently 0 or 1, and
m is independently 0 or 1,
with the proviso that in each cell p at least one of n or m is 1,
preferably characterized in that
X is H, methyl, ethyl or propyl, preferably ethyl;
r is methyl;
p is an integer from 5 to 25;
in each cell p
n is independently 0 or 1, and
m is independently 0 or 1,
provided that at least one of n or m is 1 and the number n ≧ m, preferably the total number of n is at least 2 x m, more preferably n is at least 3 x m, most preferably only n is present, in each cell p.
Suitable compounds A3 are selected from at least one polyol which is different from A2, preferably from polyester polyols, polyether polyols, polyurethane polyols, polyacrylate polyols, polymethacrylate polyols, polycarbonate polyols or mixtures thereof, particularly preferably A3 is selected from polyester polyols, polyether polyols, polycarbonate polyols, polyurethane polyols, polyacrylate polyols, polymethacrylate polyols, C having at least two hydroxyl groups2 -C10Hydrocarbons, or mixtures thereof, particularly preferably, a3 is a polyester polyol. Preferred compounds of a3 are the compounds described above under (b 1) and (b 2).
In a preferred embodiment, the polyol (B) is prepared from the following components: from 5 to 80% by weight, preferably from 10 to 60% by weight, of component (A1),
2 to 50% by weight, preferably 3 to 20% by weight, of (A2), and
from 10 to 80% by weight, preferably from 40 to 70% by weight, of component (A3), based on the total weight of polyol (B).
The polyurethane resins used according to the invention are preferably prepared in such a way that the polyol (B) is homogeneously mixed with at least one uretdione group-containing curing agent (a) based on aliphatic, (cyclo) aliphatic, araliphatic and/or aromatic polyisocyanates which does not contain chemically bonded hydrophilicizing groups in a nonaqueous system and dispersed with deionized water.
Suitable as solvents under (C) are all liquid substances which do not react with the other contents. Preferred are acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, heavy benzenes such as commercially available Solvesso 100 and Solvesso 150, propylene glycol mono-n-butyl ether, dipropylene glycol dimethyl ether, methoxypropyl acetate, diesters or mixtures thereof. Subsequently, the solvent used can optionally be distilled off.
According to the invention, additives (D) customary in lacquer and adhesive technology, such as levelling agents, for example silicone polymers or acrylates, photoprotectors, for example sterically hindered amines, catalysts, for example tin (II) 2-ethylhexyl octoate or dibutyltin dilaurate, or other auxiliaries, for example those described in EP 0669353, may be contained in a total amount of preferably from 0.05 to 5% by weight. Fillers and pigments such as titanium dioxide may be added to the aqueous composition in amounts up to 50% by weight.
Example (b):
the raw materials used are as follows:
remer N120-Linear, bifunctional TMP-initiated polyethylene glycol monomethyl ether having an OH number of 100-120 mg KOH/g, obtainable from Perstorp
Desmodur W-monomeric cycloaliphatic diisocyanate having an NCO content of about 32% by weight, CAS number 5124-30-1, available from Covestro.
Polyester 1
Polyester from 2446 g trimethylolpropane, 6381 g tetrahydrophthalic anhydride and 4429 g neopentyl glycol; the acid number was <3 mg KOH/g and the OH number was 250 mg KOH/g.
Polyester 2
Polyesters from 1774 g of trimethylolpropane, 744 g of phthalic anhydride, 1099 g of isophthalic acid, 551 g of neopentyl glycol and 775 g of benzoic acid; the acid number was <3 mg KOH/g and the OH number was 250 mg KOH/g.
The analytical method used was:
all viscosity measurements were carried out with a Physica MCR 51 rheometer from Anton Paar Germany GmbH (DE) according to DIN EN ISO 3219: 1994-10.
The NCO content was determined by titration in accordance with DIN EN ISO 11909: 2007-05.
OH numbers were determined by titration in accordance with DIN EN ISO 4629-2: 2015-02.
The acid number is determined by titration in accordance with DIN EN ISO 2114: 2002-06.
The solids content is determined in accordance with DIN EN ISO 3251:2008-06, method B, with the aid of a circulating air furnace.
The mean particle size (MTG) is determined in accordance with DIN ISO 13321:2004-10 using a Zetasizer Nano from Malvern (DE).
pH value according to DIN ISO 976:2008-07 with a pH meter, with distilled water at a ratio of 1: 4 was measured at dilution.
The residual monomer content was determined by gas chromatography with internal standard according to DIN EN ISO 10283.
Pendulum hardness was measured according to DIN EN ISO 1522:2007-04 with a K baby pendulum on a standardized coil test panel (coil coating black-CS 200570, Heinz Zanders Pr uf-Blech-Logitik).
Chemical resistance was measured on standardized coil test panels (coil coating black-CS 200570, Heinz Zanders Pr uf-Blech-Logitik). A cotton ball soaked with the test substance (xylene or water) was placed on the paint surface and covered with a watch glass. After a given loading time, the cotton soaked with the test substance is removed, the loaded site is wiped dry and immediately examined. The paint surface was evaluated for softening or discoloration. The evaluation was carried out according to DIN EN ISO 4628-1 as follows:
0 none, i.e. no apparent damage
1 very little, i.e. small, just a significant amount of damage
2 little, i.e. small, but significant amount of damage
3 moderate to high degree of damage
4 considerable number of breakdowns
5 very much damage.
All% data refer to weight percent unless explicitly stated otherwise.
Preparation of a crosslinking agent containing uretdione groups (crosslinking agent 1, preparation example)
1000g (4.50 mol) of isophorone diisocyanate (IPDI) were admixed, at room temperature, with dry nitrogen and with stirring, in succession with 10g (1%) of triisodecyl phosphite and 20 g (2%) of 4-Dimethylaminopyridine (DMAP) as catalyst. After 20 hours, the reaction mixture having an NCO content of 28.7% (corresponding to an oligomerization degree of 21.8%) was freed of volatile constituents by means of a thin-film evaporator at a temperature of 160 ℃ and a pressure of 0.3 mbar without prior addition of catalyst poison. A pale yellow uretdione polyisocyanate was obtained with a free NCO group content of 17.0%, a monomeric IPDI content of 0.4% and a viscosity of more than 200000 mPas.
337 g of 1, 4-butanediol, 108 g of 2-ethylhexanol and 569 g e-caprolactone are mixed at room temperature under dry nitrogen, 0.3 g of tin (II) octanoate are added and stirred at 160 ℃ for 5 hours, followed by cooling to room temperature. 1850g of the previously described uretdione group-containing polyisocyanates based on IPDI heated to 80 ℃ are then added to this mixture over the course of 30 minutes. The reaction mixture is stirred at a temperature of up to 100 ℃ until the NCO content of the reaction mixture has fallen to a value of 0.8% after 7 to 8 hours. To solidify it, the reaction mixture was poured onto a metal plate, pulverized, and then dissolved in acetone, thereby producing a solution having a solid proportion of 70 wt%.
Preparation of a non-Ionically hydrophilicized polyester polyurethane 1 (precursor 1)
5258g of polyester 1 are dissolved in 4200g of acetone. To 1025g of this solution was added 200g of Ymer N120; 1.3g of tin (II) 2-ethylhexanoate and 211.5g of acetone, and the mixture is homogenized at 50 ℃ for about 1 hour. To the homogeneous solution was added 230g Desmodur W at 50 ℃ to raise the temperature to reflux temperature. The reaction mixture is kept at this temperature until the NCO content is < 0.05%, then cooled and charged into a suitable container.
Preparation of a non-Ionically hydrophilicized polyester polyurethane 2 (precursor 2)
5258g of polyester 2 were dissolved in 3886g of acetone. To 1026g of this solution was added 200g of YMER N120; 1.3g of tin (II) 2-ethylhexanoate and 211.5g of acetone, and the mixture is homogenized at 50 ℃ for about 1 hour. To this homogeneous solution was added 210g Desmodur W at 50 ℃ to bring the temperature to reflux temperature. The reaction mixture is kept at this temperature until the NCO content is < 0.05%, then cooled and charged into a suitable container.
Example 1
To 1000g of precursor 2, 391g of crosslinker 1 in acetone are added and homogenized at 40 ℃ for 1 hour with stirring. 874g of distilled water were added to the homogeneous solution. The acetone was then removed under vacuum. A storage-stable dispersion was obtained with the following characteristic numbers:
solids content 54% by weight
Acid value (100%) 2.2 mg KOH/g
MTG: 168 nm
Viscosity 670 mPas
pH value: 4.2
The dispersion was stable at 23 ℃ for 5 months.
Example 2
To 500g of precursor 1, 250g of a solution of crosslinker 1 in acetone are added and homogenized at 40 ℃ for 1 hour with stirring. To the homogeneous solution was added 655g of distilled water. The acetone was then removed under vacuum. A storage-stable dispersion was obtained with the following characteristic numbers:
solids content 54% by weight
Acid value (100%) 2.4 mg KOH/g
MTG: 198 nm
Viscosity 740 mPas
pH value: 4.5
The dispersion was stable at 23 ℃ for 5 months.
Paint technology test:
a varnish was prepared from the following composition (all weights are in g):
TABLE 1 examples 4 to 5 according to the invention
Examples 4 5
From example 1 10.00
From example 2 10.00
The dispersion was mixed in a Speed Mixer at 2000 rpm for 1 minute and applied to a coil-metal plate with a doctor blade in a layer thickness of 180 μm (wet). The panels with the applied wet paint were air dried at room temperature for 5 minutes, baked at 180 ℃ for 30 minutes and subsequently stored at room temperature for 4 days. The stored films were evaluated in terms of application technology (table 2).
TABLE 2
Examples 4 5
Appearance of paint (visual inspection) Satisfaction Satisfaction
Layer thickness (dry, mu) 60 60
Pendulum hardness(s) 130 136
Two-agentBenzene tolerance (5 minutes) 0 2
Deionized water (1 hour) 0 0
As can be seen from table 2, the uretdione-containing dispersions of the invention lead to hard and resistant paints.
Comparative example 6
247g (1.00 eq) of the abovementioned polyisocyanate containing uretdione groups and having a free isocyanate group content, based on IPDI, of 17.0% and a content of uretdione groups of 20.8% determined by calculation are heated to 80 ℃ under dry nitrogen and 500g (1.00 eq) of methoxypolyethylene glycol 500 are incorporated. Subsequently, stirring is carried out at a reaction temperature of at most 70 ℃ until the NCO content of the reaction mixture has fallen to a value of less than 0.1%. A pale yellow coloured liquid was obtained which was then dispersed in water to a solids content of 30% by weight, transferred to a 500 ml bottle with a water filled riser and allowed to stand at 23 ℃. The volume displacement of water in the riser has been observed after one day, indicating that CO is produced2And thus indicate that the polyisocyanates containing uretdione groups thus hydrophilicized are not sufficiently stable in storage (Table 3).
TABLE 3
Figure 317527DEST_PATH_IMAGE002
。

Claims (14)

1. Aqueous compositions containing uretdione groups, comprising or consisting of
(A) At least one uretdione group-containing curing agent based on aliphatic, cycloaliphatic, araliphatic and/or aromatic polyisocyanates, which does not contain chemically bonded hydrophilicizing groups;
(B) at least one nonionically hydrophilicized hydroxyl-containing polyol;
(C) optionally a solvent; and
(D) optional auxiliaries and additives;
wherein the amount ratio of components (A) and (B) is such that the molar ratio of NCO groups of curing agent (A) present as uretdiones to NCO-reactive groups of polyol (B) is from 3.0:0.5 to 0.5:3.0 and wherein A and B are present as a physical mixture.
2. Composition according to claim 1, characterized in that,
the at least one uretdione group-containing curing agent a is obtained by reaction of a monomeric isocyanate comprising or consisting of at least one monomeric isocyanate selected from: tetramethylene diisocyanate, cyclohexane-1, 3-diisocyanate and cyclohexane-1, 4-diisocyanate, pentamethylene diisocyanate, Hexamethylene Diisocyanate (HDI), 1-isocyanato-3, 3, 5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI), dicyclohexylmethane-2, 4 '-diisocyanate and/or dicyclohexylmethane-4, 4' -diisocyanate, tetramethylxylylene diisocyanate (TMXDI), triisocyanatononane, Tolylene Diisocyanate (TDI), diphenylmethane-2, 4 '-diisocyanate and/or diphenylmethane-4, 4' -diisocyanate (MDI), triphenylmethane-4, 4' -diisocyanate or naphthalene-1, 5-diisocyanate or mixtures thereof.
3. Composition according to claim 1 or 2, characterized in that,
hydroxyl group-containing monomers and/or polymers are used as starting materials for the at least one uretdione group-containing curing agent A.
4. Composition according to any one of the preceding claims, characterized in that,
the at least one uretdione group-containing curing agent A has a free NCO content of less than 5% by weight and a uretdione group content of from 1 to18% by weight of C2N2O2The molecular weight was calculated to be 84 g/mol.
5. Composition according to any one of the preceding claims, characterized in that,
the acid value of the aqueous composition is from 1 to 100 mg KOH/g.
6. Composition according to any one of the preceding claims, characterized in that,
the at least one polyol (B) is obtained by reaction of the following components
A1) At least one polyisocyanate,
A2) at least one polyalkoxy ether derivative containing at least one-OH group, and
A3) optionally at least one polyol different from A2,
preferably in the presence of a catalyst, to obtain at least one non-ionically hydrophilized hydroxyl group-containing polyol (B); wherein the acid number of the polyol (B) is preferably up to 5 mg KOH/g, in accordance with DIN EN ISO 2114:2002-06, the weight ratio of 2:1 as solvents and calculated based on solids content.
7. Composition according to any one of the preceding claims, characterized in that,
the at least one polyol (B) has an OH content of more than 1% by weight, calculated as OH groups on the solids content, and a molecular weight of 17 g/mol and/or a number-average molecular weight Mn of 500 to 20000 g/mol.
8. Composition according to any one of the preceding claims, characterized in that the solvent is chosen from acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, heavy benzene, propylene glycol mono-n-butyl ether, dipropylene glycol dimethyl ether, methoxypropyl acetate, diesters or mixtures thereof.
9. Composition according to any one of the preceding claims, characterized in that the auxiliaries and additives are chosen from levelling agents, photoprotectants, catalysts, fillers, and pigments or mixtures thereof.
10. Composition according to any one of the preceding claims, characterized in that the sum of the proportions by weight of (A), (B) and (D) is from 30 to 60% by weight, based on the solids content of the entire aqueous composition.
11. Method for producing a polyurethane layer, comprising the following steps
i) Providing an aqueous uretdione group-containing composition according to any one of claims 1 to 10;
ii) applying the mixture obtained in i) to a substrate;
iii) drying the mixture from step ii), and
iv) heating to 40 ℃ to 180 ℃ for up to 180 minutes to cure the mixture from step iii).
12. The process according to claim 11, characterized in that the uretdione group-containing aqueous composition is obtained by mixing the uretdione group-containing curing agent a with the at least one polyol B in the absence of water, followed by dispersion with water.
13. Polyurethane layer, in particular a polyurethane film, obtainable by a process according to claim 11 or 12.
14. A substrate coated or bonded with a polyurethane layer according to claim 13.
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US15/933,487 US20190292305A1 (en) 2018-03-23 2018-03-23 Uretdione based polyurethane compositions
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EP18163620.0A EP3543269A1 (en) 2018-03-23 2018-03-23 Uretdione-containing polyurethane-dispersions comprising hydrophilic groups
US15/933475 2018-03-23
US15/933,511 US11440988B2 (en) 2018-03-23 2018-03-23 Polyuretdione-containing resin blend compositions
EP18163625.9A EP3543271A1 (en) 2018-03-23 2018-03-23 Compositions containing uretdione groups and method for their preparation
US15/933,570 US10731051B2 (en) 2018-03-23 2018-03-23 Basecoat acid neutralization through inorganic salts
US15/933495 2018-03-23
EP18163621.8A EP3543270A1 (en) 2018-03-23 2018-03-23 Catalyst system for uretdion dispersions
US15/933,470 US11292864B2 (en) 2018-03-23 2018-03-23 Compositions using polyuretdione resins
US15/933511 2018-03-23
US15/933507 2018-03-23
US15/933487 2018-03-23
US15/933,495 US11312881B2 (en) 2018-03-23 2018-03-23 One component polyurethane/allophanate formulations with reactive reducer
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US15/933,475 US11008416B2 (en) 2018-03-23 2018-03-23 Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate
US15/933,500 US10696775B2 (en) 2018-03-23 2018-03-23 Curing for polyallophanate compositions through undercoat acid neutralization
US15/933,527 US20190292296A1 (en) 2018-03-23 2018-03-23 Polyol acid neutralization for low temperature uretdione curing
US15/933553 2018-03-23
US15/933,553 US10633477B2 (en) 2018-03-23 2018-03-23 Extended pot-life for low temperature curing polyuretdione resins
US15/933,507 US20190292294A1 (en) 2018-03-23 2018-03-23 One component allophanate formulations through basecoat catalyst migration
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