DE19938758A1 - Oligomers and polymers based on diethyloctanediols, process for their preparation and their use - Google Patents

Abstract

The invention relates to oligomers and polymers which contain at least one positional isomer diethyl octanediol as a monomer unit. The invention also relates to a method for producing the same and to the use thereof for producing moulding compounds, adhesives and coating materials, especially lacquers. The invention especially relates to polyesters on the basis of 2,4-diethyloctane-1,5-diol and the use thereof in 2k-polyurethane lacquers.

Description

The present invention relates to new oligomers and polymers, the positional isomers Contain diethyloctanediols as monomer units. In addition, the present concerns Invention the use of the new oligomers and polymers for the production of Molding compounds, adhesives and coating materials, especially paints, and their Derived products, d. H. the molded parts, foils, fibers, adhesive layers and coatings, especially paintwork.

For making polyesters or copolymers containing polyester building blocks more flexible and moldings, adhesive layers and coatings produced therewith, in particular Coatings are usually the C6 building blocks hexanediol-1,6 and / or Adipic acid used. In addition, polyester and polyester co-polyurethane are the 2- Methyl-1,8-octanediol and optionally nonane-1,9-diol as C9 monomer units contained in condensed form from numerous Japanese patents such as JP-A-63182330, JP-A-01215876, JP-A-01242674, JP-A-02264082, JP-A-06329751, JP- A-0493316, JP-A-02264082, JP-A-02147238 or JP-A-02041379, the European Patent EP-A-0 562 577 or from British patent GB-A-2248844 known. A polyester is also known from the Japanese patent specification JP-A-09272731 which contains 2,7-dimethyl-1,8-octanediol as a C10 monomer unit.

These oligomers and polymers already have good application technology Properties, but one comes across when varying their property profile, For example, the further flexibilization, to a limit, when it is exceeded Make disadvantages noticeable, such as a reduction in hardness. So you want her further vary application properties and improve them so that they are new Purposes can be supplied and / or in their previous For new uses, it becomes necessary to use new monomer blocks and to provide new oligomers and polymers.

The object of the present invention is therefore to use new oligomers and polymers To provide an alternative to the previously known. The new polymers and Oligomers the advantageous properties of the known oligomers and polymers preserve and additionally offer new possibilities, the property profile in advantageous Way to vary widely so that they are also considered for new uses come.

Accordingly, the new oligomers and polymers have been found that have at least one Positionally isomeric diethyloctanediol contained as a monomer unit.

In the following, these new oligomers and polymers are called "according to the invention Oligomers and polymers ".

In addition, the new molding compounds, adhesives and coating materials were found, which contain at least one oligomer and / or polymer according to the invention. in the Following are these new molding compounds, adhesives and coating materials as "Molding compositions, adhesives and coating materials according to the invention" denotes.

Furthermore, new molded parts, foils and fibers were found, which from the Molding compositions according to the invention can be produced. In the following they are called "Moldings, foils and fibers according to the invention" referred to.

Furthermore, new adhesive layers have been found that consist of the adhesives according to the invention can be produced and are referred to below as "adhesive layers according to the invention" will.

Last but not least, new coatings have been found which result from the inventive Coating materials can be produced and hereinafter referred to as "according to the invention Coatings ".

In addition, new substrates have been found that have at least one according to the invention Have adhesive layer and / or at least one coating according to the invention and in hereinafter referred to as "substrates according to the invention".

In the context of the present invention, oligomers are compounds understood, which contain 2 to 15 recurring monomer units. Complementary on Römpp Lexikon Lacke und Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, page 425, »Oligomere«.

In contrast, in the context of the present invention under polymers Compounds understood that more than 10, in particular more than 15, recurring Contain monomer units. In addition, varnish and varnish are used on Römpp Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, page 464, »Polymers«, referred.

The essential component of the oligomers and polymers according to the invention is at least one positionally isomeric diethyloctanediol.

The positionally isomeric diethyloctanediol to be used according to the invention contain one linear C8 carbon chain.

Regarding the two ethyl groups, the C8 carbon chain shows the following Substitution patterns on: 2.3, 2.4, 2.5, 2.6, 2.7, 3.4, 3.5, 3.6 or 4.5. According to the invention it is advantageous if the two ethyl groups are in the 2,4-position, d. that is, it is 2,4-diethyloctanediols.

Regarding the two hydroxyl groups, the C8 carbon chain has the following Substitution pattern on: 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 2.3, 2.4, 2.5, 2.6, 2.7 , 2.8, 3.4, 3.5, 3.6, 3.7, 3.8, 4.5, 4.6, 4.8, 5.6, 5.7, 5.8, 6.7, 6.8 or 7.8. According to the invention it is from Advantage if the two hydroxyl groups are in the 1,5-position, i. that is, it is Diethyloctane-1,5-diols.

The two substitution patterns are combined with one another in any manner, ie that the diethyloctanediols to be used according to the invention are 2,3-diethyloctane-1,2-, -1,3-, -1,4-, -1,5- , -1.6-, -1.7-, -1.8-, -2.3-, -2.4-, -2.5-, -2.6-, -2.7-, - 2.8-, -3.4-, -3.5-, -3.6-, -3.7-, -3.8-, -4.5-, -4.6-, 4.7 -, -4.8-, -5.6 -, -5.7-, -5.8-, -6.7-, -6.8- or -7.8-diol,
2,4-diethyloctane-1,2-, -1,3-, -1,4-, -1,5-, -1,6-, -1,7-, -1,8-, -2, 3-, -2.4-, -2.5-, -2.6-, -2.7-, - 2.8-, -3.4-, -3.5-, -3.6- , -3.7-, -3.8, -4.5-, -4.6-, 4.7-, 4.8-, -5.6 -, -5.7-, -5.8 -, -6.7-, -6.8- or -7.8-diol,
2,5-diethyloctane-1,2-, -1,3-, -1,4-, -1,5-, -1,6-, -1,7-, -1,8-, -2, 3-, -2.4-, -2.5-, -2.6-, -2.7-, - 2.8-, -3.4-, -3.5-, -3.6- , -3.7-, -3.8 -, 4.5-, 4.6-, 4.7-, -4.8-, -5.6-, -5.7-, -5.8 -, -6.7-, -6.8- or -7.8-diol,
2,6-diethyloctane-1,2-, -1,3-, -1,4-, -1,5-, -1,6-, -1,7-, -1,8-, -2, 3-, -2.4-, -2.5-, -2.6-, -2.7-, -2.8-, -3.4-, -3.5-, -3.6- , -3.7-, -3.8-, -4.5-, -4.6-, -4.7-, -4.8-, -5.6 -, -5.7-, - 5, 8-, -6.7-, -6.8- or 7.8-diol,
2,7- diethyloctane-1,2-, -1,3-, -1,4-, -1,5-, -1,6-, -1,7-, -1,8-, -2, 3-, -2.4-, -2.5-, -2.6-, -2.7-, -2.8-, -3.4-, -3.5-, -3.6- , -3.7-, -3.8 -, -4.5-, -4.6-, -4.7-, -4.8-, -5.6-, -5.7-, - 5.8-, -6.7-, -6.8- or -7.8-diol,
3,4-diethyloctane-1,2-, -1,3-, -1,4-, -1,5-, -1,6-, -1,7-, -1,8-, -2, 3-, -2.4-, -2.5-, -2.6-, -2.7-, - 2.8-, -3.4-, -3.5-, -3.6- , -3.7-, -3.8, -4.5-, -4.6-, -4.7-, -4.8-, -5.6 -, -5.7-, -5 , 8-, -6.7-, -6.8- or -7.8-diol,
3,5-diethyloctane-1,2-, -1,3-, -1,4-, -1,5-, -1,6-, -1,7-, -1,8-, -2, 3-, -2.4-, -2.5-, -2.6-, -2.7-, - 2.8-, -3.4-, -3.5-, -3.6- , -3.7-, -3.8, -4.5-, -4.6-, -4.7-, -4.8-, -5.6 -, -5.7-, -5 , 8-, -6.7-, -6.8- or -7.8-diol,
3,6-diethyloctane-1,2-, -1,3-, -1,4-, -1,5-, -1,6-, -1,7-, -1,8-, -2, 3-, -2.4-, -2.5 -, -2.6-, -2.7-, - 2.8-, -3.4-, -3.5-, -3.6- , -3.7-, -3.8-, -4.5-, -4.6-, -4.7-, -4.8-, -5.6 -, -5.7-, - 5.8-, -6.7-, -6.8- or -7.8-diol or um
4,5-diethyloctane-1,2-, -1,3-, -1,4-, -1,5-, -1,6-, -1,7-, -1,8-, -2, 3-, -2.4-, -2.5-, -2.6-, -2.7-, - 2.8-, -3.4-, -3.5-, -3.6- , -3.7-, -3.8-, -4.5-, -4.6-, -4.7-, 4.8-, -5.6 -, -5.7-, -5 , 8-, -6.7-, -6.8- or -7.8-diol
acts.

The positionally isomeric diethyloctanediols to be used according to the invention can be used as individual compounds or as mixtures of two or more diethyloctanediols for the Production of the oligomers and polymers according to the invention can be used.

Particular advantages result from the use of 2,4-diethyloctane-1,5-diol.

The positionally isomeric diethyloctanediols to be used according to the invention are per se known compounds and can with the help of conventional and known synthetic methods of organic chemistry such as base-catalyzed aldol condensation or they fall as by-products of large chemical syntheses such as the production of 2- Ethyl hexanol.

Their proportion of the oligomers and polymers according to the invention can be extraordinary vary widely and depends on the intended use of the Oligomers and polymers according to the invention and their necessary for this Property profile. According to the invention, it is advantageous if they are in the Starting products of the oligomers and polymers according to the invention in an amount of, based on the starting products, 2 to 60% by weight, preferably 3 to 55% by weight, particularly preferably 5 to 50 wt .-% and in particular 7 to 45 wt .-% are included.

The oligomers and polymers according to the invention originate from the customary and known ones Classes of oligomers and polymers. In addition, varnish and varnish are used on Römpp Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, page 464, »Polymers«, referred. It is essential that the positional isomers to be used according to the invention Diethyloctanediols in the preparation of the oligomers and polymers according to the invention can be built into these as monomer modules.

The oligomers and polymers according to the invention are linear or branched. It is also possible that linear in the oligomers and polymers of the invention Chains are combined with highly branched chains. The oligomer and polymer chains have a block-like, comb-like or statistical structure with regard to the monomer units. Of course, these principles of construction can be combined with one another in any way be combined. Furthermore, the oligomers and Polymers have a core-shell structure and / or as crosslinked microparticles are available.

Accordingly, the number average molecular weight Mn and Inconsistency in the molecular weight Mw / Mn of the oligomers and Depending on the intended use and structure, polymers vary extremely widely. According to the invention, number average molecular weights Mn are from 700 to 2,000,000 Advantage. Within this range, number average molecular weights Mn of 1,000 up to 1,500,000, in particular 2,000 to 1,000,000, other special advantages. Here lies the non-uniformity of the molecular weight Mw / Mn advantageously from 1.1 to 20, preferably 1, 2 to 15 and in particular 1.3 to 10.

Examples of advantageous oligomers and polymers according to the invention are Polyaddition resins, polycondensation resins or resins obtained by polyaddition and Polycondensation can be produced. In addition, varnish and varnish are used on Römpp Printing colors, Georg Thieme Verlag, Stuttgart, New York, 1998, page 457, »Polyaddition« and "Polyaddition Resins (Polyadducts)", as well as pages 463 and 464, "Polycondensates", Reference is made to "polycondensation" and "polycondensation resins".

Examples of advantageous polyaddition resins according to the invention and / or Polycondensation resins are polyethers, polyesters, polycarbonates, polyurethanes, Polyureas, polyamides, polyimides or copolymers, the ether, ester, carbonate, Urethane, urea, amide and / or imide groups in the oligomer and / or Polymer chains included.

Examples of particularly advantageous polyaddition resins and / or Polycondensation resins are polyester, polyurethane, polyester co-polyether, polyester co-polycarbonate, polyester-co-polyurethane, polyester-co-polyamide, polyester-co- polyureas or polyester co-polyimides.

Of these, the polyesters, the polyurethanes and the polyester co- polyurethane is particularly advantageous.

From a methodological point of view, their manufacture has no peculiarities, but takes place according to the usual and known methods of producing polycondensation resins and polyaddition resins.

For example, the polyesters according to the invention can be obtained by reacting Polycarboxylic acids and those to be used according to the invention described above positionally isomeric diethyloctanediols and optionally further polyols and / or Monocarboxylic acids.

Examples of suitable polycarboxylic acids are aromatic polycarboxylic acids such as Terephthalic acid, isophthalic acid, phthalic acid, trimellitic acid or pyromellitic acid and their core substituted alkyl derivatives; cycloaliphatic polycarboxylic acids such as Tetrahydrophthalic acid, 1,2-cyclobutanedicarboxylic acid, 1,3-cyclobutanedicarboxylic acid, 1,2- Cyclopentanedicarboxylic acid, 1,3-cyclopentanedicarboxylic acid, hexahydrophthalic acid, 1,3- Cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, 4-methylhexahydrophthalic acid or tricyclodecane dicarboxylic acid, both in its cis and in its trans form and can be used as a mixture of both forms; or acyclic Polycarboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, Pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedicarboxylic acid or Dodecanedicarboxylic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid or dimer fatty acids.

The esterifiable derivatives of the above are also suitable according to the invention Polycarboxylic acids, such as. B. their mono- or polyvalent esters with aliphatic alcohols with 1 to 4 carbon atoms or hydroxy alcohols with 1 to 4 carbon atoms. You can also the anhydrides of the above-mentioned polycarboxylic acids can also be used, provided that they exist.

Examples of suitable, optionally used monocarboxylic acids are 2- Ethylhexanoic acid, 3,3,5-trimethylhexanoic acid, isononanoic acid, pelargonic acid, fatty acids from coconut fat, fatty acids from natural oils, resin acids, benzoic acid or p-tert.- Butylbenzoic acid.

Examples of suitable polyols in addition to those to be used according to the invention Positionally isomeric diethyloctanediols for the purpose of further variation of the Property profile can be used as starting products, such as diols Ethylene glycol, 1,2- or 1,3-propanediol, methylpropane-1,3-diol, ether oligomers of Ethylene glycol and propylene glycol such as diethylene glycol or dipropylene glycol, 1,2-, 1,3- or 1,4-butanediol, 1,2-, 1,3-, 1,4- or 1,5-pentanediol, 1,2-, 1,3-, 1,4-, 1,5- or 1, 6- Hexanediol, hydroxypivalic acid neopentyl ester, neopentyl glycol, 1,2-, 1,3- or 1,4- Cyclohexanediol, 1,2-, 1,3- or 1,4-cyclohexanedimethanol, tricyclodecanedimethanol (TCD), trimethylpentanediol, ethyl butyl propanediol, octanediols, nonanediols, 2-butyl-2-ethylpropanediol-1,3, 2-butyl-2-methylpropanediol-1,3, 2-phenyl-2-methylpropanediol-1,3, 2-propyl-2-ethylpropanediol-1,3, 2-di-tert-butylpropanediol-1,3,2-butyl-2-propylpropanediol-1,3,1-dihydroxymethyl-bi cyclo [2.2.1] heptane, 2,2-diethylpropanediol-1,3,2,2-dipropylpropanediol-1,3 2-cyclo hexyl-2-methylpropanediol-1,3, 2,5-dimethyl-hexanediol-2,5, 2,5-diethylhexanediol-2,5, 2-ethyl-5-methylhexanediol-2,5, 2,4-dimethylpentanediol-2,4, 2,3-dimethylbutanediol-2,3, 1,4- (2'-hydroxypropyl) benzene, 1,3- (2'-hydroxypropyl) benzene or dimer diols Dimer fatty acids; or triols such as glycerol, trimethylolethane, trimethylolpropane, tris hydroxyethyl isocyanurate or pentaerythritol.

Here, the diols and the triols are used in a molar ratio that the desired degree of branching results.

The polyesters according to the invention are produced by the known methods esterification, as described, for example, in DE-A-40 24 204, page 4, lines 50 to 65, are described. The reaction usually takes place at temperatures between 180 and 280 ° C, optionally in the presence of a suitable esterification catalyst, such as B. lithium octoate, dibutyltin oxide, dibutyltin dilaurate or para-toluenesulfonic acid.

The polyesters according to the invention are usually prepared in the presence small amounts of a suitable solvent carried out as an entrainer. As Towing agents are e.g. B. aromatic hydrocarbons, such as in particular xylene and (cyclo) aliphatic hydrocarbons, e.g. B. cyclohexane or methylcyclohexane, used.

Do the polyesters according to the invention also contain at least one, preferably at least two and in particular two free hydroxyl groups, they can in particular advantageous way of producing further polymers according to the invention, d. H. Polyester copolymers are used, which is another very special advantage of polyester according to the invention.

For example, the polyurethanes according to the invention are customary and known methods of polyurethane chemistry from polyisocyanates and Positionally isomeric diethyloctanediols to be used according to the invention and optionally further compounds which have at least one, preferably at least contain two functional groups reactive towards isocyanate groups, available. Instead of the positionally isomeric diethyloctanediols or in addition to these, those described above are also particularly advantageous polyester according to the invention used, whereby the polyester-co- polyurethane result.

Examples of suitable polyisocyanates are isophorone diisocyanate (= 5-isocyanato-1- isocyanatomethyl-1,3,3-trimethyl-cyclohexane), 5-isocyanato-1- (2-isocyanatoeth-1-yl) - 1,3,3-trimethyl-cyclohexane, 5-isocyanato-1- (3-isocyanatoprop-1-yl) -1,3,3-trimethyl cyclohexane, 5-isocyanato- (4-isocyanatobut-1-yl) -1,3,3-trimethyl-cyclohexane, 1- Isocyanato-2- (3-isocyanatoprop-1-yl) cyclohexane, 1-isocyanato-2- (3-isocyanatoeth-1- yl) cyclohexane, 1-isocyanato-2- (4-isocyanatobut-1-yl) cyclohexane, 1,2- Diisocyanatocyclobutane, 1,3-diisocyanatocyclobutane, 1,2-diisocyanatocyclopentane, 1,3- Diisocyanatocyclopentane, 1,2-diisocyanatocyclohexane, 1,3-diisocyanatocyclohexane, 1,4- Diisocyanatocyclohexane, Dicyclohexyhnethan-2,4'-diisocyanate, liquid bis (4- isocyanatocyclohexyl) methane of a trans / trans content of up to 30 wt .-%, the can be obtained by phosgenation of isomer mixtures of bis (4- aminocyclohexyl) methane or by fractional crystallization of commercially available Bis (4-isocyanatocyclohexyl) methane, as described in the patents DE-A-44 14 032, GB- A-1220717, DE-A-16 18 795 or DE-A-17 93 785, Tri methylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, Hexamethylene diisocyanate, ethylethylene diisocyanate, trimethylhexane diisocyanate, Heptane methylene diisocyanate or diisocyanates derived from dimer fatty acids as they distributed by Henkel under the trade name DDI 1410 and in the Patent specifications DO 97/49745 and WO 97149747 are described, in particular 2- Heptyl-3,4-bis (9-isocyanatononyl) -1-pentyl-cyclohexane, or 1,2-, 1,4- or 1,3- Bis (isocyanatomethyl) cyclohexane, 1,2-, 1,4- or 1,3-bis (2-isocyanatoeth-1- yl) cyclohexane, 1,3-bis (3-isocyanatoprop-1-yl) cyclohexane, 1,2-, 1,4- or 1,3-bis (4- isocyanatobut-1-yl) cyclohexane, tolylene diisocyanate, xylylene diisocyanate, Bisphenylene diisocyanate, naphthylene diisocyanate or diphenylmethane diisocyanate.

Examples of suitable further compounds which may be used as starting products and contain at least one, preferably at least two functional groups which are reactive toward isocyanate groups are

• - Saturated and unsaturated high molecular and low molecular diols and in minor amounts of triplets to introduce branching, in particular the diols and triols described above,
• - polyamines,
• - aminolcohols and
• - Compounds through which stabilizing (potentially) ionic and / or non-ionic functional groups are introduced.

Further examples of highly suitable compounds of this type and processes for their preparation of polyurethanes, especially polyester-co-polyurethanes, are from the patents EP-A-0 073 517, EP-A-0 089 497, EP-A-0 228 003, EP-A-0 234 361, EP-A-0 543 817 or EP-A-0 574 417.

Further particular advantages result if the oligomers and Polymers with olefinically unsaturated monomers to form graft copolymers be implemented.

Examples of suitable olefinically unsaturated monomers are

• Essentially (meth) acrylic acid esters free of acid groups,
• - Monomers which carry at least one hydroxyl group per molecule and in are essentially free of acid groups, such as hydroxyalkyl esters of acrylic acid, Methacrylic acid or another alpha, beta-olefinically unsaturated carboxylic acid, which are derived from an alkylene glycol which is esterified with the acid, or by reacting the alpha, beta-olefinically unsaturated carboxylic acid with a Alkylene oxide are available
• - Monomers which have at least one acid group which is in the corresponding Acid anion group is convertible, carry per molecule,
• Vinyl esters of monocarboxylic acids branched in the alpha position with 5 to 18 Carbon atoms in the molecule,
• - Reaction products from acrylic acid and / or methacrylic acid with the Glycidyl ester of a monocarboxylic acid branched in the alpha position with 5 to 18 Carbon atoms per molecule,
• Cyclic and / or acyclic olefins such as ethylene, propylene, 1-butene, 1-pentene, Hex-1-ene, cyclohexene, cyclopentene, norbornene, butadiene, isoprene, cyclopentadiene and / or dicyclopentadiene, especially ethylene,
• - (meth) acrylic acid amides,
• - Monomers containing epoxy groups, such as the glycidyl esters, ethylenically unsaturated carboxylic acids,
• - vinyl aromatic hydrocarbons,
• - nitriles,
• Vinyl compounds, in particular vinyl and / or vinylidene dihalides, N Vinyl pyrrolidone, vinyl ester or vinyl ether,
• - Allyl compounds, especially allyl ethers and esters.

Further examples of suitable olefinically unsaturated monomers and suitable ones Methods of graft copolymerization are described, for example, in the patents EP-A-0 521 928, EP-A-0 730 613 or EP-A-0 787 159.

The oligomers and polymers according to the invention can have functional groups contain cross-linking reactions with complementary functional groups. The complementary functional groups in the invention can Oligomers and polymers themselves, which make them self-crosslinking. The complementary functional groups can, however, also be in compounds, which are separate from the oligomers and polymers of the invention. Of the Such mixtures are known to experts as externally crosslinking systems and the relevant ones Connections referred to as crosslinking agents. In these externally networked systems the oligomers and polymers according to the invention take on the function of Binder.

Examples of suitable complementary functional groups to be used according to the invention, which undergo crosslinking reactions, are summarized in the following overview. In the overview, the variable R stands for an acyclic or cyclic aliphatic, an aromatic and / or an aromatic-aliphatic (araliphatic) radical; the variables R ¹ and R ² represent the same or different aliphatic radicals or are linked to one another to form an aliphatic or heteroaliphatic ring.

Overview Examples of complementary functional groups in the Binder (self-crosslinking)

Binders and crosslinking agents or
Crosslinking agents and binders

Instead of or in addition to these complementary functional groups the oligomers and polymers according to the invention contain functional groups which are at the action of actinic radiation with each other or with other groups react. Examples of suitable groups of this type are the allyl groups listed above. and vinyl groups. Other examples of suitable groups are acrylate and Methacrylate groups, especially acrylate groups. With actinic radiation it can electromagnetic radiation such as X-rays, UV radiation, visible Light or near IR light (NIR) or around corpuscular radiation such as electron beams act.

The oligomers and polymers according to the invention described above are suitable excellent for the production of molding compounds, adhesives and coating materials, especially paints.

For the production of the molding compositions according to the invention, inventive liquid or solid oligomers and polymers are used, the de above functional groups described, so that they are more common and known Way by heating and / or by irradiation with actinic radiation thermosetting molded parts, films and fibers according to the invention are processed can. However, solid oligomers and Polymers used that have thermoplastic properties and no reactive functional groups have more, so that they in a conventional and known manner for example by extrusion followed by injection molding, film blowing or drawing from fibers to thermoplastic molded parts, films and fibers according to the invention can be processed.

The moldings, films and fibers according to the invention can be excellently glue with the adhesives according to the invention and / or with the inventive Coat or paint coating materials.

The molding compositions according to the invention consist of the oligomers according to the invention and polymers or they contain conventional and known plastic additives in effective Amounts.

For the production of adhesives according to the invention, which serve as contact adhesives, are preferably used oligomers and polymers according to the invention which do not or only a very small amount of the functional groups described above contain.

For the production of adhesives according to the invention, which serve as reactive adhesives, are preferably used oligomers and polymers according to the invention, which over have a larger amount of the functional groups described above, so that they can be cured thermally and / or with actinic radiation. Furthermore The adhesives according to the invention can be used for coating materials described additives included, provided that they are for use in adhesives in Come into consideration.

The adhesives according to the invention can be used to describe those described below Substrates, in particular the moldings, films and fibers according to the invention, in glue in an excellent way.

The oligomers and polymers according to the invention are very particularly preferred for the production of coating materials, especially paints, used. For for this purpose, oligomers and polymers are preferably used contain the functional groups described above. Here are the Coating materials according to the invention are self-crosslinking in the abovementioned sense or cross-linking, but especially cross-linking. Furthermore, they are thermally or with actinic radiation or thermally and with actinic radiation hardenable, the latter also referred to by experts as dual cure.

The selection of the respective complementary functional groups is based on the one hand after that they must not have any undesirable reactions during storage and / or, if necessary, do not interfere with curing with actinic radiation or inhibit, and on the other hand in which temperature range the thermal Hardening should take place.

Here, especially with regard to thermally sensitive substrates such as plastics, According to the invention, it is advantageous to choose a temperature range which is 100 ° C. in particular not exceeding 80 ° C. With regard to these framework conditions themselves hydroxyl groups and isocyanate groups or carboxyl groups and epoxy groups proved to be advantageous as complementary functional groups, which is why they are shown in the coating materials according to the invention, which as two or Multi-component systems are present, are preferably used according to the invention. Particular advantages result if the hydroxyl groups are functional groups in the binders and the isocyanate groups as functional groups in the Crosslinking agents are used.

Can higher crosslinking temperatures, for example from 100 ° C to 180 ° C, applied are also used as coating materials according to the invention One-component systems into consideration, in which the functional groups in the Binders preferably thio, amino, hydroxyl, carbamate, allophanate, carboxy, and / or (meth) acrylate groups, but especially hydroxyl groups, and the functional groups in the crosslinking agents, preferably anhydride, carboxy, Epoxy, blocked isocyanate, urethane, methylol, methylol ether, siloxane, amino, Hydroxy and / or beta-hydroxyalkylamide groups are.

In the context of the present invention is a one-component (1K) system thermally curing coating material to understand, in which the binder and Crosslinking agents side by side, d. H. in one component. requirement this is because the two components only at higher temperatures and / or at Crosslink radiation with actinic radiation.

The coating material of the invention can also be a two-component (2K) or multi-component (3K, 4K) system.

In the context of the present invention, this is to be understood as a coating material in which in particular the binder and the crosslinking agent are separated from one another in at least two components are present, which are only shortly before application be put together. This form is chosen when binders and Crosslinking agents react with each other at room temperature. Coating materials This type is used primarily for coating thermally sensitive substrates, especially used in car refinishing.

Last but not least, the coating materials of the invention can be physically curing be d. that is, by solvent release from the applied coating materials and / or crosslink by coalescing the binder particles. The link within the Painting is done by looping the polymer chains of the binders. Complementary is on Römpp Lexikon Lacke und Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, pages 274 and 275, "Hardening".

The coating material of the invention is used to produce decorative and / or protective coatings, especially paints such as transparent ones Clear coats, primers, in particular stone chip protection primers and Filler, or color and / or effect coatings, especially top coats and basecoats. The paintwork can be a or be multilayered.

For these purposes, the coating material of the invention in general paint additives added in effective amounts. Type and amount of Additives depend primarily on the intended use of the invention Coating material. Preferably these additives are among the processing and Application conditions of the coating material of the invention are not volatile.

If the coating materials of the invention are used as a topcoat or basecoat, it contains color and / or effect pigments in customary and known amounts. The Pigments can and can consist of inorganic or organic compounds be effect and / or color. The coating material of the invention ensures therefore due to this large number of suitable pigments, a universal range of applications Coating materials and enables the realization of a variety of colors and optical effects.

Furthermore, the coating material of the invention can be organic and inorganic Contain fillers in usual and known, effective amounts. examples for suitable fillers are chalk, calcium sulfate, barium sulfate, silicates such as talc or Kaolin, silicas, oxides such as aluminum hydroxide or magnesium hydroxide or organic fillers such as textile fibers, cellulose fibers, polyethylene fibers or wood flour.

These additives are omitted if the coating materials according to the invention are used as clear lacquers be used.

Examples of suitable additives which can be present in both the clearcoats and topcoats of the invention are

• - Common and known oligomeric and polymeric binders such as thermally curable linear and / or branched and / or block-like hydroxyl groups, comb-like and / or randomly constructed poly (meth) acrylates or Acrylate copolymers, polyesters, alkyds, aminoplast resins, polyurethanes, acrylated polyurethanes, acrylated polyesters, polylactones, polycarbonates, polyethers, Epoxy resin-amine adducts, (meth) acrylate diols, partially saponified polyvinyl esters or polyureas or (meth) acrylic functional curable with actinic radiation (Meth) acrylate copolymers, polyether acrylates, polyester acrylates, unsaturated Polyester, epoxy acrylates, urethane acrylates, amino acrylates, melamine acrylates, Silicone acrylates and the corresponding methacrylates;
• - Usual and known thermally and / or curable with actinic radiation Reactive diluents as the diethyloctanediols to be used according to the invention as such, di- or higher functional (meth) acrylates or (meth) acrylate groups containing polyisocyanates;
• - UV absorbers and light stabilizers such as benzotriazoles, triazines or oxalanilides;
• - radical scavengers such as HALS compounds;
• - Thermolabile free radical initiators such as organic peroxides, organic Azo compounds or C-C-cleaving initiators such as dialkyl peroxides, Peroxocarboxylic acids, peroxodicarbonates, peroxide esters, hydroperoxides, Ketone peroxides, azodinitriles or benzpinacol silyl ether;
• - Crosslinking catalysts such as dibutyltin dilaurate or lithium decanoate;
• - Photoinitiators such as those of the Norrish II type, whose mechanism of action an intramolecular variant of the hydrogen abstraction reactions, as they occur in a variety of ways in photochemical reactions (For example, here on Römpp Chemie Lexikon, 9th expanded and revised Edition, Georg Thieme Verlag Stuttgart, Vol. 4, 1991, referenced) or cationic Photoinitiators (examples here are on Römpp Lexicon lacquers and printing inks, Georg Thieme Verlag Stuttgart, 1998, pages 444 to 446, referenced), in particular Benzophenones, benzoins or benzoin ethers or phosphine oxides;
• - Silp additives;
• - polymerization inhibitors such as phosphites;
• - defoamer,
• - Emulsifiers, especially non-ionic emulsifiers such as alkoxylated alkanols and polyols, phenols and alkylphenols or anionic emulsifiers such as Alkali salts or ammonium salts of alkane carboxylic acids, alkane sulfonic acids, and Sulphonic acids of alkoxylated alkanols and polyols, phenols and Alkylphenols;
• Wetting agents such as siloxanes, fluorine-containing compounds, carboxylic acid semiesters, Phosphoric acid esters, polyacrylic acids and their copolymers or polyurethanes;
• - adhesion promoters such as tricyclodecane dimethanol;
• - leveling agent;
• - high-boiling organic solvents ("long solvents");
• - film-forming aids such as cellulose derivatives;
• - transparent fillers based on silicon dioxide, aluminum oxide or Zirconium oxide; In addition, the Römpp Lexicon Lacke and Druckfarben, Georg Thieme Verlag, Stuttgart, 1998, pages 250 to 252, referenced;
• - Sag control agents such as ureas, modified ureas and / or silicas, as for example in the references EP-A-192 304, DE-A-23 59 923, DE- A-18 05 693, WO 94/22968, DE-C-27 51 761, WO 97/12945 or "color + lacquer", 11/1992, pages 829 ff.
• Rheology-controlling additives such as those from the patent specifications WO 94/22968, EP A-0 276 501, EP-A-0 249 201 or WO 97/12945; cross-linked polymers Microparticles as disclosed, for example, in EP-A-0 008 127; inorganic layered silicates such as aluminum-magnesium silicates, Sodium magnesium and sodium magnesium fluorine lithium layered silicates of the Montmorillonite type; Silicas such as aerosils; or synthetic polymers with ionic and / or associative groups such as polyvinyl alcohol, Poly (meth) acrylamide, poly (meth) acrylic acid, polyvinyl pyrrolidone, Styrene-maleic anhydride or ethylene-maleic anhydride copolymers and their derivatives or hydrophobically modified ethoxylated urethanes or polyacrylates;
• - flame retardants and / or
• - matting agents.

Further examples of suitable paint additives (G) are given in the textbook »Paint Additives« by Johan Bieleman, Wiley-VCH, Weinheim, New York, 1998.

These additives are used in conventional and known effective amounts added.

The material composition of the coating materials according to the invention can vary extremely widely depending on their intended use, which is a further essential advantage of the coating materials. In general, it is advisable to use the amounts of binders, crosslinking agents and additives known from the prior art. Coating materials according to the invention are advantageous here

• 1 to 90% by weight, preferably 2 to 80% by weight, particularly preferably 3 to 75% by weight % and in particular 4 to 70 wt .-% of at least one of the invention Oligomers and polymers,
• 0 to 60% by weight, preferably 1 to 50% by weight, particularly preferably 2 to 45% by weight % and in particular 4 to 40% by weight of at least one crosslinking agent and
• 0 to 90% by weight, preferably 0.1 to 80% by weight, particularly preferably 0.5 to 75 % By weight and in particular 1 to 70% by weight of at least one additive,

where the percentages refer to the solids content of the concerned coating material according to the invention and add up to 1% by weight.

The coating material can be in various forms.

So he can with appropriate choice of his components described above as liquid coating material is present, which is essentially free of organic Solvents and / or water (100% system).

However, the coating material can be a solution or dispersion of the Components described above in organic solvents and / or water act. Another advantage of the coating material is that it contains solids up to more than 80% by weight, based on the coating material can.

Furthermore, the coating material can be selected as above described components be a powder coating. For this purpose, the Crosslinking agents can be microencapsulated if it is a polyisocyanate. This powder coating can then, if appropriate, be dispersed in water, resulting in a Powder slurry paint results.

The coating material can furthermore be a two- or Be a multi-component system in which at least the crosslinking agent is separate from the other ingredients stored and added to them shortly before use becomes. In this case, the coating material of the invention can also be aqueous the crosslinking agent preferably in a solvent-containing one Component is present.

Furthermore, the coating material can be part of a so-called mixing system or be a modular system, as described, for example, in the patents DE-A-41 10 520, EP-A-0 608 773, EP-A-0 614 951 or EP-A-0 471 972.

The production of the coating material from its components has none Special features, but takes place in the usual and known manner by mixing the components in suitable mixing units such as stirred tanks, dissolvers or extruders according to the methods suitable for the production of the respective coating materials.

The coating material of the invention is used to produce the coating material of the invention Paint finishes, especially multi-layer paint finishes ML, on primed or unprimed substrates.

All surfaces to be painted, which are hardened by the paints thereon using heat and / or actinic Radiation are not damaged, which are e.g. B. the invention Molded parts, foils and fibers, metals, plastics, wood, ceramics, stone, textiles, Fiber composites, leather, glass, glass fibers, glass and rock wool, mineral and resin-bound building materials, such as gypsum and cement boards or roof tiles, as well as composites of these materials. Accordingly, the multi-layer coating according to the invention is also for Applications outside of automotive painting, especially automotive painting suitable. Here she comes in particular for the painting of furniture and the industrial painting, including coil coating and container coating. in the As part of industrial painting, it is suitable for painting practically everyone Parts for private or industrial use such as radiators, household appliances, Small parts made of metal such as screws and nuts, hubcaps, rims, packaging or electrotechnical components such as motor windings or transformer windings.

In the case of electrically conductive substrates, primers can be used which are in be produced in a customary and known manner from electrocoat materials (ETL). Therefor come both anodic (ATL) and cathodic (KTL) electrocoat, but especially KTL.

With the multi-layer coating according to the invention, primers can also be primed or non-primed plastics such. B. ABS, AMMA, ASA, CA, CAB, EP, UF, CF, MF, MPF, PF, PAN, PA, PE, HDPE, LDPE, LLDPE, UHMWPE, PET, PMMA, PP, PS, SB, PUR, PVC, RF, SAN, PBT, PPE, POM, PUR-RIM, SMC, BMC, PP-EPDM and UP (Short designations according to DIN 7728T1). The plastics to be painted can of course also polymer blends, modified plastics or fiber be strong plastics. It can also be used in vehicle construction, especially Automotive engineering, plastics used are used.

In the case of non-functionalized and / or non-polar substrate surfaces, these can before coating in a known manner, a pretreatment, such as with a plasma or with flame treatment, or with a hydro primer.

The multilayer coatings ML according to the invention can be used in different ways getting produced.

In a first preferred variant, the process according to the invention comprises the following process steps:

• A) producing a filler lacquer layer by applying a filler to the substrate,
• B) curing the filler lacquer layer, resulting in the filler layer,
• C) producing a solid-color topcoat by applying a solid-color topcoat to the Filler layer and
• D) hardening of the solid-color topcoat, resulting in the solid-color topcoat.

Another preferred variant of the method according to the invention comprises the method steps:

• A) producing a basecoat layer by applying a basecoat to the Substrate,
• B) drying the basecoat film,
• C) producing a clear coat by applying a clear coat to the Basecoat and
• D) joint curing of the basecoat layer and the clearcoat layer, as a result of which Basecoat and clearcoat result (wet-on-wet process).

A third preferred variant of the method according to the invention comprises the method steps:

• A) producing a filler lacquer layer by applying a filler to the substrate,
• B) curing the filler lacquer layer, resulting in the filler layer,
• C) producing a basecoat layer by applying a basecoat to the Filler layer,
• D) drying the basecoat film,
• E) producing a clear coat by applying a clear coat on the Basecoat and
• F) joint curing of the basecoat layer and the clearcoat layer, whereby the Basecoat and clearcoat result (wet-on-wet process).

Which preferred variant is chosen depends on the intended use of the Multilayer coatings ML according to the invention. So in particular the third one Variant particularly preferred for automotive series painting.

Accordingly, the multilayer coatings ML according to the invention can be one have different structures.

In a first preferred variant of the multilayer coating ML according to the invention

• 1. a mechanical energy absorbing filler layer and
• 2. a color and / or effect top coat

on top of each other in the given order.

In a second preferred variant of the multilayer coating ML according to the invention

• 1. a mechanical energy absorbing filler layer,
• 2. a color and / or effect basecoat and
• 3. a clear coat

on top of each other in the given order.

In a third preferred variant of the multilayer coating ML according to the invention

• 1. a color and / or effect basecoat and
• 2. a clear coat

on top of each other in the given order. The third preferred variant is used especially in plastic painting.

The application of the coating material of the invention can be done by all the usual methods Application methods, such as B. spraying, knife coating, brushing, pouring, dipping, watering, Dribbling or rolling take place. The substrates to be coated can be used as such rest, with the application device or system being moved. However, this can also be done substrate to be coated, in particular a coil, are moved, the Application system rests relative to the substrate or is moved in a suitable manner. Spray application methods are preferably used, such as. Compressed air spraying, airless spraying, high rotation, electrostatic spray application (ESTA), possibly connected with hot spray application such as hot air Hot spray. The applications can be used at temperatures of max. 70 to 80 ° C be carried out so that suitable application viscosities are achieved without a change in the briefly acting thermal load or Damage to the coating material and its possibly to be reprocessed Enter overspray. So the hot spraying can be designed so that the Coating material is heated only very briefly in or just before the spray nozzle.

The spray booth used for the application can be used, for example, with a optionally temperature-controlled circulation can be operated with a suitable Absorbent medium for the overspray, e.g. B. the coating material itself, operated becomes.

If the coating material contains components with actinic radiation can be networked, the application becomes one when illuminated with visible light Wavelength of over 550 nm or in the absence of light. This will a material change or damage to the coating material and the overspray avoided.

Generally the filler coat, top coat, basecoat and Clear coat applied in a wet coat thickness that after curing layers with the necessary and advantageous layer thicknesses for their functions result. in the In the case of the filler layer, this layer thickness is 10 to 150, preferably 15 to 120, particularly preferably 20 to 100 and in particular 25 to 90 microns, in the case of Topcoat is 5 to 90, preferably 10 to 80, particularly preferably 15 to 60 and in particular 20 to 50 µm, in the case of the basecoat it is 5 to 50, preferably 10 to 40, particularly preferably 12 to 30 and in particular 15 to 25 μm, and in the case of the clearcoats it is 10 to 100, preferably 15 to 80, particularly preferably 20 to 70 and in particular 25 to 60 microns.

According to the invention, the filler coat, top coat, basecoat and Depending on its material composition, the clear coat is thermal, with actinic Radiation or be cured thermally and with actinic radiation. According to the invention, it is advantageous to apply the basecoat before the application of the Cure the clearcoat layer only partially or only to harden it together harden with the clear coat (wet-on-wet method).

Curing can take place after a certain period of rest. It can last for 30 s to 2 h, preferably 1 min to 1 h and in particular 1 min to 30 min. The Rest time is used, for example, for the course and for degassing the paint layers or for Evaporation of volatile components such as solvents, water or carbon dioxide if the coating material was applied with supercritical carbon dioxide as a solvent is. The rest period can be supported by using elevated temperatures up to 80 ° C and / or be shortened, provided that no damage or changes to the Coatings of lacquer occur, such as premature complete networking.

The thermal hardening has no special features in terms of method, but takes place according to the usual and known methods such as heating in a forced air oven or Irradiate with IR lamps. The thermal hardening can also be carried out in stages respectively. The thermal curing advantageously takes place at a temperature of 50 to 100 ° C, particularly preferably 80 to 100 ° C and in particular 90 to 100 ° C during a time of 1 min to 2 h, particularly preferably 2 min to 1 h and in particular 3 min to 30 min. Substrates that can withstand high thermal loads can be used thermal crosslinking can also be carried out at temperatures above 100 ° C. In general, it is advisable to use temperatures of 180 ° C., preferably 160 ° C. and in particular not to exceed 140 ° C.

The thermal hardening can with the appropriate material composition of the Coating material are supplemented by curing with actinic radiation, wherein in particular UV radiation and / or electron beams can be used. If necessary, it can use actinic radiation from other radiation sources be carried out or supplemented. In the case of electron beams is preferred worked under an inert gas atmosphere. This can be done, for example, by feeding Guaranteed carbon dioxide and / or nitrogen directly to the surface of the paint layer will.

Even in the case of curing with UV radiation, the formation of ozone can increase avoid working under inert gas.

For curing with actinic radiation, the usual and known Radiation sources and optical auxiliary measures applied. Examples of suitable ones Radiation sources are high or low pressure mercury vapor lamps, which are optionally doped with lead to open a radiation window up to 405 nm, or Electron beam sources. Their arrangement is known in principle and can Conditions of the workpiece and the process parameters can be adjusted. At Completely shaped workpieces such as automobile bodies cannot be more direct Areas accessible to radiation (shadow areas) such as cavities, folds and others design-related undercuts with point, small area or All-round spotlights connected to an automatic movement device for the Irradiation of cavities or edges can be cured.

The facilities and conditions of these hardening methods are described in R. Holmes, »U. V. and E. B. Curing Formulations for Printing Inks, Coatings and Paints, SITA Technology, Academic Press, London, United Kindom 1984.

The curing can take place in stages, i. H. by multiple exposure or Irradiation with actinic radiation. This can also take place alternately, i. that is alternately cured with UV radiation and electron radiation.

Thermal curing and curing are combined with actinic radiation applied (dual cure), these methods can be used simultaneously or alternately will. If the two hardening methods are used alternately, can for example, started with thermal curing and with actinic curing Radiation to be ended. In other cases, using the Begin hardening with actinic radiation and end with it. The specialist can the hardening method, which is particularly well suited for each individual case his general knowledge, possibly with the help of simpler Determine preliminary tests.

The multilayer coatings ML according to the invention have an outstanding Property profile based on the mechanics, optics, corrosion resistance and Liability is very well balanced. So the invention Multilayer coatings ML the high optical quality and required by the market Interlayer liability and no problems like lack of Condensation layers resistant to condensation, cracking (mud cracking) in the Basecoats or flow disorders or surface structures in the Clear coats.

In particular, the multilayer coating ML according to the invention has one excellent metallic effect, an excellent D.O.I. (distinctiveness of the reflected image) and excellent surface smoothness. It is weather stable, resistant to chemicals and bird droppings and scratch resistant and shows a very good Reflow behavior.

Another major advantage is the very good paintability of the Multilayer coating ML according to the invention also without sanding. That way she can easily with common and known highly scratch-resistant coating materials on the basis organically modified ceramic materials are coated.

Last but not least, it proves to be a very special advantage that with the help of A multi-layer coating can be realized using the method described above, which is based exclusively on the coating materials of the invention.

Accordingly, the substrates according to the invention also have particular advantages such as one longer service life, a better aesthetic impression on the viewer and a better technological usability.

Examples example 1 The Production of the Polyester 1 According to the Invention

In a 4 liter stainless steel reactor equipped with a stirrer, reflux condenser, Water separator and adjustable heating, were 195 parts by weight of hexanediol-1,6, 720 Parts by weight of trimethylolpropane, 334 parts by weight of 2,4-diethyloctane-1,5-diol, 131 Parts by weight of isononanoic acid, 1272 parts by weight of hexahydrophthalic anhydride and 104 Weighed parts by weight of xylene. The resulting mixture was slowly maximized Heated to 225 ° C and at this temperature up to an acid number of 16 mg KOH / g and a viscosity of 12 dPas (60% in solvent naphtha) condensed. The resulting one The reaction mixture was then allowed to cool and at 130 ° C. at 1530 Parts by weight of solvent naphtha dissolved. The resulting solution of the invention Polyester had a solids content of 58.5 wt .-%, an acid number of 16.3 mg KOH / g and a viscosity of 11 dPas (original).

Example 2 The Production of the Polyester 2 According to the Invention

In a 4 liter stainless steel reactor equipped with a stirrer, reflux condenser, Water separator and adjustable heating, 383 parts by weight of trimethylolpropane, 355 parts by weight of 2,4-diethyloctane-1,5-diol, 69 parts by weight of isononanoic acid, 676 Weighing in parts by weight of hexahydrophthalic anhydride and 59 parts by weight of xylene and slowly heated to a maximum of 225 ° C and at this temperature up to an acid number of 17 mg KOH / g and a viscosity of 12 dPas (60% in solvent naphtha) condensed. The resulting reaction mixture was then allowed to cool and dissolved at 130 ° C with 840 parts by weight of solvent naphtha. The resulting solution of the polyester according to the invention had a solids content of 59.5% by weight, a Acid number of 17.1 mg KOH / g and a viscosity of 13 dPas (original).

Example 3 The Production of the Clearcoat 1 According to the Invention

In a stirred vessel with a mechanical stirrer 68.6 parts by weight of the Polyester 1 according to the invention according to Example 1, 1.0 part by weight of Tinuvin® 292 (Light stabilizer from Ciba-Geigy), 1.5 parts by weight of Tinuvin® 1130 (Light stabilizer from Ciba-Geigy), 10 parts by weight of butyl diglycol acetate, 9 Parts by weight of butyl glycol acetate, 7 parts by weight of methoxypropylacetate, 9.3 parts by weight Weighed in butyl acetate and 0.2 part by weight of BYK® 310 (leveling agent from Byk) and mixed. The resulting mixture was added 24.1 shortly before application Parts by weight of a crosslinking agent based on hexamethylene diisocyanate given, after which the two-component system was homogenized.

Example 4 The production of the multilayer coating ML 1 according to the invention

For the production of the multilayer coating ML according to the invention, customary and known test boards made of steel, which are coated with an electrodeposition coating, made from a commercially available electrocoat and with a filler layer, made from a standard fountain pen that was painted. Was on the filler layer in the usual and known manner a commercially available waterborne basecoat from BASF Coatings AG applied with a layer thickness of 12-15 microns and 10 minutes at 80 ° C. vented. Finally, the clearcoat material 1 of Example 3 according to the invention was coated with a Layer thickness of 40-45 microns applied, after which the basecoat and the clearcoat for 20 Minutes at 140 ° C (wet-on-wet method).

The multilayer coating ML according to the invention proved to be extraordinary Resistant to condensed water: constant water condensation test according to DIN 50017 and 53209: no bubbles, index 0.

The interlayer adhesion was also excellent: cross cut with tesa tear according to DIN EN ISO 2409: according to DIN EN ISO 2409: GT 0.

The deformability of the paint according to DIN EN ISO 1520: 1995-04 was also very high good: Erichsen depression: 6.2 mm.

These values demonstrate the advantageousness of the multi-layer coating according to the invention, the clearcoat of the invention and the polyester of the invention.

Example 5 The Production of the Clearcoat 2 According to the Invention

Example 3 was repeated, except that instead of the polyester 1 according to the invention Examples 1 of the polyester 2 according to the invention from Example 2 was used.

Example 6 The production of the multilayer coating ML 2 according to the invention

Example 4 was repeated, only that instead of the clearcoat material 1 according to the invention Example 3 the clearcoat material 2 according to the invention was used in accordance with Example 5. It the same beneficial results resulted.

Claims (20)

1. Oligomers and polymers containing at least one positionally isomeric diethyloctanediol included as a monomer unit. 2. Oligomers and polymers according to claim 1, characterized in that the Positionally isomeric diethyloctanediol is a 2,3-, 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6- or 4,5-diethyloctanediol. 3. Oligomers and polymers according to claim 2, characterized in that the Positionally isomeric diethyloctanediol is a 2,4-diethyloctanediol. 4. Oligomers and polymers according to one of claims 1 to 3, characterized characterized in that the positionally isomeric diethyloctanediol is a diethyloctane-1,2- 1,3-, -1,4-, -1,5-, -1,6-, -1,7-, -1,8-, -2,3-, -2,4-, -2, 5-, -2.6-, -2.7-, -2.8-, -3.4-, -3.5-, -3.6-, -3.7-, -3.8-, -4.5-, 4.6-, -4.7-, -4.8-, -5.6-, -5, 7-, -5.8-, -6.7-, -6.8- or - 7,8-diol. 5. Oligomers and polymers according to claim 4, characterized in that the Positionally isomeric diethyloctanediol is a diethyloctane-1,5-diol. 6. Oligomers and polymers according to claim 5, characterized in that the Positionally isomeric diethyloctanediol is 2,4-diethyloctane-1,5-diol. 7. Oligomers and polymers according to one of claims 1 to 6, characterized characterized in that it is polyaddition resins and / or Polycondensation resins. 8. Oligomers and polymers according to claim 7, characterized in that the Polyaddition resins and / or polycondensation resins polyethers, polyesters, Polycarbonates, polyurethanes, polyureas, polyamides, polyimides or Are copolymers containing ether, ester, carbonate, urethane, urea, amide and / or imide groups in the oligomer and / or polymer chains. 9. Oligomers and polymers according to claim 8, characterized in that the Polyaddition resins and / or polycondensation resins polyesters, polyurethanes, Polyester co-polyether, polyester co-polycarbonate, polyester co-polyurethane, Polyester-co-polyamides, polyester-co-polyureas or polyester-co-polyimides are. 10. Oligomers and polymers according to one of claims 1 to 9, characterized characterized in that they are linear and / or branched and / or block-like, comb-like and / or are constructed statistically, have a core-shell structure and / or are present as cross-linked microparticles. 11. Oligomers and polymers according to one of claims 1 to 10, characterized in that they

• functional groups which undergo crosslinking reactions with complementary functional groups which are located in the oligomers and polymers themselves and / or in compounds present separately therefrom, and / or
• functional groups which react with one another or with other groups when exposed to actinic radiation,

exhibit. 12. Oligomers and polymers according to one of claims 1 to 12, characterized characterized in that they are grafted with olefinically unsaturated monomers. 13. Use of the oligomers and polymers according to one of claims 1 to 12 for the production of molding compounds, adhesives and coating materials, especially paints. 14. Molding compositions, adhesives and coating materials, characterized in that they at least one oligomer and / or polymer according to one of claims 1 to 12 contain. 15. Use of the molding compositions, adhesives and coating materials according to Claim 14, for the production of molded parts, films, fibers, adhesive layers and decorative and / or protective coatings, in particular Paintwork. 16. Molded parts, films and fibers, producible from molding compositions according to claim 14. 17. adhesive layers, producible from adhesives according to claim 14. 18. Coatings, in particular paints, producible from coating materials, in particular paints, according to claim 14. 19. Substrates which have at least one adhesive layer according to claim 17 and / or at least one coating, in particular painting, according to claim 18 exhibit. 20. Substrates according to claim 19, characterized in that they are molded parts, Films and fibers according to claim 16, motor vehicle bodies, industrial Components, including electrical components, coils and packaging, or furniture acts.