WO2003000813A1 - Carbamat- und/oder allophanatgruppen enthaltende, thermisch und mit aktinischer strahlung härtbare gemische - Google Patents
Carbamat- und/oder allophanatgruppen enthaltende, thermisch und mit aktinischer strahlung härtbare gemische Download PDFInfo
- Publication number
- WO2003000813A1 WO2003000813A1 PCT/EP2002/006703 EP0206703W WO03000813A1 WO 2003000813 A1 WO2003000813 A1 WO 2003000813A1 EP 0206703 W EP0206703 W EP 0206703W WO 03000813 A1 WO03000813 A1 WO 03000813A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dual
- groups
- carbamate
- cure
- mixtures according
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 87
- 230000005855 radiation Effects 0.000 title claims abstract description 56
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title claims abstract description 28
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- 125000000524 functional group Chemical group 0.000 claims abstract description 32
- 239000000470 constituent Substances 0.000 claims abstract description 29
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 25
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- 239000003365 glass fiber Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
- 229940094522 laponite Drugs 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- KCAMXZBMXVIIQN-UHFFFAOYSA-N octan-3-yl 2-methylprop-2-enoate Chemical compound CCCCCC(CC)OC(=O)C(C)=C KCAMXZBMXVIIQN-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000004753 textile Chemical class 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000004924 water-based lacquer Substances 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
- 239000002023 wood Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09D201/025—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
Definitions
- the present invention relates to the use of the new coating materials containing carbamate and / or AUophanat phenomenon, curable thermally and with actinic radiation, as clearcoats, in particular for the production of clearcoats in the context of color and / or effect multi-coat coatings.
- actinic radiation includes electromagnetic radiation, such as near infrared, visible light, UV radiation or X-rays, in particular UV radiation, and
- Thermally curable coating materials comprising low molecular weight compounds, oligomers and / or polymers containing carbamate groups are known from patent applications EP 0 710 707 A 2, WO 87/00851, EP 0 594 068 A 1, EP 0 594 142 A 1, WO 94 / 10211 and DE 199 46 048 A 1 or the patent EP 0 636 660 B1.
- the coatings produced from the known coating materials are characterized by a high etch resistance and chemical resistance. The dual-cure crosslinking of these coating materials is not described in the literature.
- the known dual-cure mixtures can contain reactive diluents curable with actinic radiation, such as di- or highly functional (meth) acrylates such as trimethylolpropane tri (meth) acrylate. These additives must be selected from a long list of suitable additives.
- the dual-cure mixtures can be used as coating materials, adhesives and sealants.
- the object of the present invention is to provide new dual-cure mixtures containing carbamate and / or AUophanat phenomenon, thermally and with actinic radiation, which can be used as dual-cure coating materials, adhesives and sealants, these being the high to reach the technological level of the state of the art, if not to exceed it.
- the new carbamate and / or AUophanat phenomenon containing thermal and actinic radiation curable coating materials, adhesives and sealants should provide coatings, adhesive layers and seals that achieve, if not exceed, the high technological level of the prior art, and at the same time have high scratch resistance and very good reflow behavior.
- the coatings, adhesives and seals, in particular coatings, produced from the dual-cure mixtures according to the invention had high scratch resistance and very good reflow behavior at high hardness because hardness and scratch resistance are frequently opposing parameters.
- the content of the constituents (A) in the dual-cure mixtures according to the invention can vary very widely and depends on the requirements of the particular intended use.
- the dual-cure mixtures according to the invention preferably contain the constituents (A) in an amount of, based on the solids of the dual-cure mixture according to the invention, 10 to 90, preferably 12 to 85, particularly preferably 14 to 80, very particularly preferably 16 to 75 and in particular 18 to 75% by weight.
- solid is understood to mean the sum of the constituents of the respective dual-cure mixture according to the invention, which build up the coatings, adhesive layers or seals after the thermal curing.
- the dual-cure mixtures according to the invention further contain at least one constituent (B) selected from the group consisting of low molecular weight compounds, oligomers and polymers containing allophanate and / or carbamate-reactive functional groups.
- the low molecular weight compounds are preferred (B) used, which are also referred to as crosslinking agents.
- the crosslinking agents (B) are used when the constituents (A) contain no carbamate- and / or allophanate-reactive functional groups, ie are not self-crosslinking.
- crosslinking agent (B) and low molecular weight compounds, the oligomers and / or polymers (A1) so that in the dual-cure mixtures according to the invention the ratio of complementary reactive functional groups in the crosslinking agent (B ) and reactive functional groups in the constituents (A1) between 2: 1 to 1: 2, preferably 1.5: 1 to 1: 1, 5, particularly preferably 1.2: 1 to 1: 1, 2 and in particular 1, 1: 1 to 1: 1, 1.
- the dual-cure mixtures according to the invention contain at least one constituent (C) which on average contains at least one reactive functional group with at least one bond which can be activated with actinic radiation in the molecule.
- component (C) may also contain at least one allophanate and / or carbamate reactive functional group.
- the content of the constituents (C) of the dual-cure mixtures according to the invention can likewise vary widely.
- the dual-cure mixtures according to the invention can also contain at least one rheology aid (D) with pseudoplastic behavior.
- the rheology aid (D) is preferably selected from the group consisting of urea derivatives and silicas.
- the content of the rheology aids (D) in the dual-cure mixtures according to the invention can vary very widely.
- the dual-cure mixtures according to the invention preferably contain the rheology aids (D) in an amount of 0.1 to 10, preferably 0.2 to 9, particularly preferably 0, based on the solids of the dual-cure mixture according to the invention, 3 to 8, very particularly preferably 0.4 to 7 and in particular 0.5 to 6% by weight.
- the dual-cure mixtures according to the invention can also contain at least one wetting agent (E).
- the wetting agents (E) in the dual-cure mixtures according to the invention are preferably in an amount of 0.01 to 5, preferably 0.02 to 4, based on the solids of the dual-cure mixture according to the invention preferably 0.03 to 3, very particularly preferably 0.04 to 2, in particular 0.05 to 1% by weight.
- the dual-cure mixtures according to the invention can also contain customary and known pigments (F) and / or additives (G).
- EP 0 710 707 A 2 page 4, lines 1 to 27, or EP 0 915 113 A 1st page 2, lines 44 to 48, and page 6, lines 21 to 25,
- Suitable binders (A) come from the polymer classes of the random, alternating and / or block-like linear and / or branched and / or comb-like (co) polymers of ethylenically unsaturated monomers, or polyaddition resins and / or polycondensation resins. These terms are supplemented by Römpp Lexikon Lacke und Druckmaschine, Georg Thieme Verlag, Stuttgart, New York, 1998, page 457, "Polyaddition” and “Polyadditionharze (polyadducts)", and pages 463 and 464, "Polycondensates”, “Polycondensation” and “Polycondensation Resins”.
- Examples of highly suitable (co) polymers (A) are (meth) acrylate copolymers and partially saponified polyvinyl esters, in particular (meth) acrylate copolymers.
- Polycondensation resins (A) are polyesters, alkyds, polyurethanes, polylactones, polycarbonates, polyethers, epoxy resin-amine adducts, polyureas, polyamides or polyimides, in particular polyesters.
- the oligomers and / or polymers (A) very particularly preferably originate from the polymer classes of the (meth) acrylate copolymers and polyester.
- Oligomers and polymers (A) containing AUophanate groups and which originate from the abovementioned polymer classes are described in German patent application DE 198 39 453 A1, page 2, line 65, to page 6, line 34, and page 7, lines 25 to 53, known.
- the oligomers and / or polymers (A) are preferably prepared by using a monomer mixture which contains at least one olefinically unsaturated carboxylic acid, for example methacrylic acid, in the presence of a glycidyl ester of Versatic ⁇ acid (cf.Römpp Lexikon Lacke und Druckmaschine, Georg Thieme Verlag, Stuttgart New York, 1998 "Versatic ⁇ acids", pages 605 and 606) copolymerized, after which the resulting hydroxyl group-containing
- Suitable allophanate and / or carbamate-reactive functional groups (i) are N-methylol groups and N-methylol ether groups, preferably the methyl, ethyl, n-propyl and / or n-butyl ether.
- the constituents (A2) in question, in particular the oligomers and / or polymers (A2), are then partially or completely self-crosslinking, which is why the use of crosslinking agents (B) can be dispensed with completely or largely in this case.
- Suitable dispersing groups (ii) are anion-forming groups, such as carboxylic acid, sulfonic acid or phosphonic acid groups, or anionic groups, such as carboxylate, sulfonate or phosphonate groups, cation-forming groups such as primary, secondary or tertiary amino groups, or cationic groups, For example, ammonium groups, such as primary secondary, tertiary or quaternary ammonium groups, sulfonium groups and phosphononium groups, or polyalkylene oxide groups, such as polyethylene oxide groups, which can be incorporated in the oligomers and polymers (A) in a lateral, terminal and / or chain position (cf.Römpp Lexikon Lacke and Druckmaschine, Georg Thieme Verlag, Stuttgart, New York, 1998, "Water-dispersible binders", page 619, and “Water-soluble binders", pages 626 and 625).
- anion-forming groups such as carboxylic acid, sulf
- groups (i) can be introduced by polymerizing in olefinically unsaturated monomers containing N-methylol ether groups or by means of polymer-analogous reactions of pendant and / or terminal amino groups with formaldehyde.
- Groups (ii) can, for example, by polymerizing in olefinically unsaturated carboxylic acids such as acrylic acid or methacrylic acid or by polymer-analogously reacting hydroxyl groups with carboxylic acid anhydrides such as maleic anhydride or
- Suitable crosslinking agents (B) are aminoplast resins.
- the constituents (C) curable with actinic radiation contain on average at least one reactive functional group, preferably at least two, particularly preferably at least three and in particular three reactive functional groups in the molecule, which contains at least one, in particular one, bond which can be activated with actinic radiation, or contain.
- constituents (C) can contain at least one of the allophanate and / or carbamate-reactive functional groups described above.
- bonds which can be activated with actinic radiation are carbon-hydrogen single bonds or carbon-carbon, carbon-oxygen, carbon-nitrogen, carbon-phosphorus or carbon-silicon single bonds or double bonds.
- double bonds in particular the carbon-carbon double bonds (hereinafter referred to as "double bonds") are preferably used.
- Suitable double bonds are, for example, in (meth) acrylate, ethacrylate, crotonate, cinnamate, vinyl ether, vinyl ester, ethenylarylene, dicyclopentadienyl, norbomenyl, isoprenyl, isoprenyl, isopropenyl, allyl or butenyl groups; Ethenylarylene, dicyclopentadienyl, norbomenyl, isoprenyl, isopropenyl, allyl or butenyl ether groups or ethenylarylene, dicyclopentadienyl, norbomenyl, isoprenyl, isopropenyl, allyl or butenyl ester groups.
- (meth) acrylate groups, in particular acrylate groups are of particular advantage and are therefore used with very particular preference in accordance with the invention.
- suitable constituents (C) which contain six or more double bonds in the molecule are (meth) acrylic-functional (meth) acrylic copolymers, polyether acrylates, polyester acrylates, unsaturated polyesters, epoxy acrylates, urethane acrylates, amino acrylates, acrylated amino resins such as melamine acrylates, silicone acrylates and the corresponding methacrylates.
- the urethane (meth) acrylates (C) are advantageous and are therefore used with particular preference.
- Suitable constituents (C) are known from German patent application DE 198 18 735 A1, column 2, lines 24 to 36, column 3, line 16, to column 6, line 33, and column 6, lines 34 to 68 .
- Well-suited examples are pentaerythritol triacrylate, which is sold under the brand Sartomer ⁇ 444 D by Cray Valley, France, and dipentaerythritol pentaacrylate, which is sold under the brand Sartomer ⁇ 399 by the same company.
- the rheology aids (D) are selected from the group consisting of urea derivatives and silicas.
- Suitable rheological aids (D) are colored, for example, in the references EP 0 192 304 A1, DE 23 59 923 A1, DE 18 05 693 A1, WO 94/22968, DE 27 51 761 C2, WO 97/12945 and " + lack ", 11/1992, pages 829 ff., WO 00/31194, WO 00/37520, DE 199 24 172 A1, DE 199 24 171 A1 or DE 199 24 170 A1.
- Rheology aids (D) are preferably used which can be prepared by reacting at least one amine and / or water with at least one isocyanate, in the presence of at least one aminoplast resin and / or at least one of the above-described oligomers and / or polymers (A).
- the amines are preferably used for their preparation.
- the amines are preferably selected from the group consisting of acyclic aliphatic, aliphatic-aromatic, cycloaliphatic, aliphatic-cycloaliphatic and cycloaliphatic-aromatic primary and secondary monoamines and polyamines.
- Examples of suitable monoamines are from German patent applications DE 199 24 172 A1, page 3, lines 3 to 10, or DE 199 24 171 A1, page 3, lines 35 to 42, or international patent applications WO 00/31194, page 11 , Lines 14 to 29, and WO 00/37520, page 3, line 15, to page 4, line 5.
- Methoxypropylamine, benzylamine and / or n-hexylamine are particularly preferably used.
- the statistical average of the polyamines contains at least two primary and / or secondary amino groups in the molecule. Examples of suitable polyamines are known from international patent application WO 00/37520, page 4, lines 6 to 19.
- Monoisocyanates and polyisocyanates are suitable as isocyanates.
- the monoisocyanates are used for the reaction with the polyamines and the polyisocyanates for the reaction with the monoamines.
- the polyisocyanates and the monoamines are preferably used for the preparation of the rheological aids (D).
- Polyisocyanates are preferably used which have a statistical average of at least 1.8, preferably at least 2 and in particular 2 isocyanate groups in the molecule.
- suitable polyisocyanates and diisocyanates are described in international patent applications WO 00/31194, page 11, line 30, to page 12, line 26, and WO 00/37520, page 5, line 4, to page 6, line 27, or German Patent applications DE 199 24 172 A1, page 3, lines 11 to 23, DE 199 24 170 A1, column 3, line 61, to column 6, line 68, or DE 199 24 171 A1, page 3, lines 43, to page 5, line 34, described in detail.
- Hexamethylene diisocyanate and its oligomers, especially trimers, are particularly preferably used.
- Suitable oligomers and polymers (A) are those described above.
- the amount of constituents (A) which is introduced into the dual-cure mixtures according to the invention by the rheology aids (D) is included in their content of binders (A).
- the weight ratio of aminoplast resin and / or oligomer and / or polymer (A) to rheological aid (D) can be 100: 1, preferably 90: 1, preferably 80: 1, particularly preferably 70: 1, very particularly preferably 60: 1 and in particular 50: 1.
- Aminoplast resins (B) which contain rheology aids (D) prepared in this way are customary and known and are marketed, for example, under the Setamine® XL 1268 brand by Akzo Nobel.
- the silicas used as rheology aids (D) are selected from the group consisting of modified pyrogenic, hydrophilic and hydrophobic, transparent silicas.
- Hydrophobic fumed silicon dioxides are particularly preferably used, the agglomerates and aggregates of which have a chain-like structure and which can be produced by flame hydrolysis of silicon tetrachloride in a detonating gas flame. They preferably have a primary particle size of 2 to 20 nm. They are sold, for example, by Degussa under the brand Aerosil ®.
- Precipitated water glasses such as nanohectorites, which are sold, for example, by Südchemie under the Optigel ® brand or by Laporte under the Laponite ® brand, are also used with particular preference.
- suitable silicas are known from German patent application DE 199 24 172 A1, page 3, lines 28 to 32.
- a further example of suitable hydrophilic, transparent silicas is Aerosil ⁇ 380 with an inner surface of 380 m 2 / g (measured according to BET according to DIN 66131).
- Wetting agents (E) i. See the definition of Römpp Lexikon Lacke und Druckmaschine, Georg Thieme Verlag, Stuttgart, New York, 1998 »Wetting Agents (Wetting Agents)», page 409.
- Wetting agents (E) are preferably selected from the group consisting of siloxanes, fluorine-containing compounds, carboxylic acid half-esters, phosphoric acid esters, polyacrylic acids and their copolymers and polyurethanes. Polyurethanes are preferably used.
- Well-suited wetting agents (E) are, for example, the commercial products
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Sealing Material Composition (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT02743223T ATE432326T1 (de) | 2001-06-21 | 2002-06-18 | Carbamat- und/oder allophanatgruppen enthaltende, thermisch und mit aktinischer strahlung härtbare gemische |
EP02743223A EP1406980B1 (de) | 2001-06-21 | 2002-06-18 | Carbamat- und/oder allophanatgruppen enthaltende, thermisch und mit aktinischer strahlung härtbare gemische |
JP2003507205A JP4553234B2 (ja) | 2001-06-21 | 2002-06-18 | カルバメート基及び/又はアロファネート基を含有する、熱及び化学線により硬化可能な混合物 |
US10/473,728 US7129280B2 (en) | 2001-06-21 | 2002-06-18 | Mixtures which contain carbamate groups and/or allophanate groups and can be cured thermally and by using actinic radiation |
CA002443455A CA2443455A1 (en) | 2001-06-21 | 2002-06-18 | Mixtures which contain carbamate groups and/or allophanate groups and can be cured thermally and by using actinic radiation |
DE50213575T DE50213575D1 (de) | 2001-06-21 | 2002-06-18 | Carbamat- und/oder allophanatgruppen enthaltende, thermisch und mit aktinischer strahlung härtbare gemische |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10129969.9 | 2001-06-21 | ||
DE10129969A DE10129969A1 (de) | 2001-06-21 | 2001-06-21 | Carbamat- und/oder Allophanatgruppen enthaltende, thermisch und mit aktinischer Strahlung härtbare Gemische |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003000813A1 true WO2003000813A1 (de) | 2003-01-03 |
Family
ID=7688972
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/006703 WO2003000813A1 (de) | 2001-06-21 | 2002-06-18 | Carbamat- und/oder allophanatgruppen enthaltende, thermisch und mit aktinischer strahlung härtbare gemische |
Country Status (7)
Country | Link |
---|---|
US (1) | US7129280B2 (de) |
EP (1) | EP1406980B1 (de) |
JP (1) | JP4553234B2 (de) |
AT (1) | ATE432326T1 (de) |
CA (1) | CA2443455A1 (de) |
DE (2) | DE10129969A1 (de) |
WO (1) | WO2003000813A1 (de) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7019042B2 (en) | 2000-08-26 | 2006-03-28 | Basf Coatings Ag | Thixotropic agent that can be activated using actinic radiation, a method for its production and the use thereof |
WO2009090003A1 (de) | 2008-01-16 | 2009-07-23 | Bayer Materialscience Ag | Silikahaltige uv-vernetzbare hardcoatbeschichtungen mit urethanacrylaten |
US8686090B2 (en) | 2003-12-10 | 2014-04-01 | Basf Coatings Gmbh | Use of urea crystals for non-polymeric coatings |
CN111234255A (zh) * | 2020-03-10 | 2020-06-05 | 齐鲁工业大学 | 一种水性聚氨酯用超支化有机硅润湿剂及其制备方法 |
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2002
- 2002-06-18 JP JP2003507205A patent/JP4553234B2/ja not_active Expired - Fee Related
- 2002-06-18 CA CA002443455A patent/CA2443455A1/en not_active Abandoned
- 2002-06-18 DE DE50213575T patent/DE50213575D1/de not_active Expired - Lifetime
- 2002-06-18 US US10/473,728 patent/US7129280B2/en not_active Expired - Fee Related
- 2002-06-18 WO PCT/EP2002/006703 patent/WO2003000813A1/de active Application Filing
- 2002-06-18 EP EP02743223A patent/EP1406980B1/de not_active Expired - Lifetime
- 2002-06-18 AT AT02743223T patent/ATE432326T1/de not_active IP Right Cessation
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WO2001023484A2 (en) * | 1999-09-30 | 2001-04-05 | Basf Corporation | Carbamate-functional resins having improved adhesion, method of making the same, and method of improving intercoat adhesion |
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US7019042B2 (en) | 2000-08-26 | 2006-03-28 | Basf Coatings Ag | Thixotropic agent that can be activated using actinic radiation, a method for its production and the use thereof |
US8686090B2 (en) | 2003-12-10 | 2014-04-01 | Basf Coatings Gmbh | Use of urea crystals for non-polymeric coatings |
WO2009090003A1 (de) | 2008-01-16 | 2009-07-23 | Bayer Materialscience Ag | Silikahaltige uv-vernetzbare hardcoatbeschichtungen mit urethanacrylaten |
US8101673B2 (en) | 2008-01-16 | 2012-01-24 | Bayer Materialscience Ag | Silica-containing UV-crosslinkable hardcoat coatings comprising urethane acrylates |
US11629259B2 (en) | 2019-12-23 | 2023-04-18 | Ricoh Company, Ltd. | Active energy ray curable composition, active energy ray curable ink composition, active energy ray curable inkjet ink composition, composition container, image forming device, image forming method, cured matter, and decorated matter |
CN111234255A (zh) * | 2020-03-10 | 2020-06-05 | 齐鲁工业大学 | 一种水性聚氨酯用超支化有机硅润湿剂及其制备方法 |
CN111234255B (zh) * | 2020-03-10 | 2021-11-02 | 齐鲁工业大学 | 一种水性聚氨酯用超支化有机硅润湿剂及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
DE50213575D1 (de) | 2009-07-09 |
CA2443455A1 (en) | 2003-01-03 |
EP1406980B1 (de) | 2009-05-27 |
JP4553234B2 (ja) | 2010-09-29 |
ATE432326T1 (de) | 2009-06-15 |
JP2004532350A (ja) | 2004-10-21 |
EP1406980A1 (de) | 2004-04-14 |
DE10129969A1 (de) | 2003-01-09 |
US7129280B2 (en) | 2006-10-31 |
US20040068025A1 (en) | 2004-04-08 |
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