MOISTURE-CURING ONE-COMPONENT MASS AND METHOD FOR JOINING, POURING AND COATING USING THE MASS

Description

FIELD OF THE INVENTION

[0001] The present invention relates to radiation-activated moisture-curable one-component compositions and their use in bonding, molding, sealing and coating substrates.

[0002] Furthermore, the invention relates to a method for joining, coating, molding or casting substrates using the mass. TECHNICAL BACKGROUND

[0003] Single-component compositions crosslinkable by actinic radiation and moisture are known from EP 2 545 133 B1. These contain, in addition to moisture-curable silane-based compounds, also radically radiation-curable compounds and are particularly suitable for filling electro-optical components.

[0004] Moisture-curable, one-component silane-based compounds, whose moisture curing can be induced by irradiation or heat, are known, for example, from DE 10 2016 111 590 A1. These silane-based compounds contain a photolatent and / or heat-latent acid generator. After activation of the acid generator, the compounds remain liquid for a period of at least 24 hours without the ingress of additional moisture. Despite rapid initial strength, the compounds require longer times to fully cure, especially at higher layer thicknesses, because the ingress of moisture is diffusion-controlled.

[0005] US Pat. No. 3,979,344 A and EP 1 591 464 A1 describe the catalysis of silane crosslinking using metal-containing catalysts such as dibutyltin laurate (DBTL) or aminosilanes. Although these compounds catalyze silane crosslinking, the water content remains the limiting factor for the crosslinking reaction. Particularly with thick layers or component geometries that further impede moisture penetration, it can take several days to weeks for the silane-containing compounds to fully cure. Furthermore, the use of metal-containing catalysts based on tin is questionable from an ecological perspective.

[0006] One approach to equipping a moisture-curing polymer system with a water dispenser system is known from DE 10 2011 002 440 A1. Water is released from the reaction of a cyclic carboxylic acid anhydride with a primary amine at elevated temperatures. However, the disclosure stipulates that the composition is thermoplastically processed at temperatures well above 100 °C.

[0007] EP 2 170 986 B1 describes a process for releasing water from moisture-curing polyolefins through ring-closing dehydration reactions. Amino acids or dicarboxylic acids, for example, are used as water donors, which release water under ring-closing conditions. A disadvantage of this approach is that a metal-containing catalyst is mandatory.

[0008] WO 2009 058 545 A2 discloses a composition and a method for the in-situ generation of water from vicinal diols by an elimination reaction. The compositions optionally contain an acid to further catalyze the release of water. Elevated temperatures and melt processing of the composition are also provided.

[0009] US 2012 / 088188 A1 describes a method for forming a pattern in which an acid formed by irradiating a portion of a photosensitive layer diffuses into a sublayer comprising an acid-sensitive copolymer having acid-decomposable groups and linking groups that are covalently bonded to the surface of the substrate and / or form an interpolymer crosslink. The diffusion comprises heating the sublayer and the photosensitive layer. The acid-sensitive group reacts with the diffused acid to form a polar region on the sublayer that has the shape of the pattern. The photosensitive layer is removed, forming a self-assembling layer comprising a block copolymer with a first block having an affinity for the polar region and a second block having a lower affinity for the polar region.The first block forms a domain aligned with the polar region, and the second block forms another domain aligned with the first. Removing either domain exposes part of the sublayer.

[0010] EP 2 207 851 A2 discloses a polymer composition comprising a silane-functionalized polymer, e.g., a vinyltriethoxysilane-modified polyethylene, a polyfunctional alcohol, and optionally an acid, e.g., an alkylated aryldisulfonic acid. The use of polyfunctional alcohols in the absence of a strong acid results in photocrosslinking of the silane-functionalized polymer, which in turn yields a polymer melt with improved elongation properties such as elongational viscosity and melt strength. The use of a polyfunctional alcohol in combination with a blocked strong acid ensures a slow crosslinking rate during melt processing and a high degree of final crosslinking after the polymer composition has been molded or cast.

[0011] DE 10 2015 222 028 A1 discloses cationically polymerizable polyacrylates containing alkoxysilane groups and their use.

[0012] EP 2 344 107 B1 discloses a dental composition with fluorescent pigment.

[0013] WO 2018 / 119 067 A1 discloses a photopolymer ceramic dispersion for additive manufacturing.

[0014] WO 2004 / 104113 A1 relates to a process for producing nanostructured and / or nanoporous surfaces, coatings with a nanostructured and / or nanoporous surface and articles containing these coatings.

[0015] In addition, US 2008 / 0 152 926 A1 provides a conductive article and a method for producing the same, the conductive article comprising a substrate, a conductive composite material with a conductive material in a matrix containing one or more film-forming resins having at least one polymerizable functional group, one or more adhesion promoters and one or more compounds which are reactive with the film-forming resin and which also contain at least one acidic component.

[0016] Furthermore, DE 10 2007 017 842 A1 describes a device for activating a polymerizable mass.

[0017] A disadvantage of all the approaches described is that heat is required as a signal for water release. The temperatures are so high that sensitive components can be damaged even by brief contact with the compound. Most of the described methods for releasing water require processing the curable compound under injection molding conditions. The high amounts of energy required for this are also disadvantageous from an ecological perspective. Summary of the invention

[0018] The invention is based on the object of avoiding the disadvantages of the prior art compositions and providing radiation-activated, moisture-curable, storage-stable one-component compounds based on moisture-curable compounds that release water upon curing and thus cure reliably within a short time, even in thick layers. The curing rate of the compounds is largely independent of external moisture ingress.

[0019] Preferably, the release of water should take place under mild conditions without excessive heat input.

[0020] These objects are achieved according to the invention by a one-component moisture-curing composition according to claim 1.

[0021] Advantageous embodiments of the compositions according to the invention are specified in the subclaims, which can optionally be combined with one another.

[0022] The invention further relates to the use of the compositions according to the invention as adhesives or sealants for bonding, casting, molding, sealing and coating substrates.

[0023] The invention further relates to a method for bonding, casting, molding, sealing, and coating substrates using the compositions according to the invention. In particular, the compositions can be activated by irradiation in a flow-through apparatus.

[0024] The composition according to the invention comprises (A) one or more moisture-curable compounds selected from the group of alkoxysilanes, wherein the alkoxysilane of component (A) is at least difunctional with respect to alkoxysilane groups, (B) at least one acid generator which releases an acid under the action of actinic radiation, and (C) at least one carbonyl compound or a carbonyl derivative selected from the group of aldehydes, ketones, hemiacetals and / or hemiketals.

[0025] In addition, the compositions according to the invention may additionally contain an alcohol and / or a thiol (D), a catalyst for moisture curing (E), a radiation-curable compound (F), a photoinitiator for radical polymerization (G) and further additives (H). DESCRIPTION OF PREFERRED EMBODIMENTS

[0026] The invention is described in detail and by way of example below with reference to preferred embodiments, which, however, are not to be understood in a limiting sense.

[0027] "One-component" or "one-component mass" means in the sense of the invention that the mentioned components of the mass are present together.

[0028] "Liquid" in the sense of the invention means that at 23 °C the loss modulus G" determined by viscosity measurement is greater than the storage modulus G' of the mass in question.

[0029] The masses are considered processable if the viscosity of the respective mass changes by less than 100%, preferably by less than 50%, during storage at room temperature over a period of 7 days.

[0030] Where the indefinite article "ein" or "eine" is used, this also includes the plural form "ein oder mehrere" unless this is expressly excluded.

[0031] "At least difunctional" means that each molecule contains two or more units of the respective functional group.

[0032] Unless otherwise stated, all weight proportions listed below refer to the total weight of the mass of components (A) to (H).

[0033] The compositions of the invention are liquid at room temperature and, when activated by radiation, curable by moisture without the need for external moisture. The compositions can be activated by irradiation with actinic radiation in such a way that a sufficient amount of water is released within the composition itself for moisture curing. The release of water occurs exclusively in areas accessible to the irradiation.

[0034] In a first preferred embodiment, the compositions comprise at least one moisture-curable compound (A) based on an at least difunctional alkoxysilane compound (A1). In addition, the compositions contain at least one photolatent acid (B), at least one carbonyl compound or carbonyl derivative (C) selected from the group of aldehydes, ketones, hemiacetals, and / or hemiketals, and optionally at least one alcohol and / or thiol (D). The composition of the first preferred embodiment contains no other catalysts customary for the moisture curing of alkoxysilanes, such as, for example, aminosilanes, tin compounds, or organic acids.

[0035] In a second preferred embodiment, the compositions comprise, in addition to the components of the first embodiment, at least one catalyst (E) for the moisture curing of the alkoxysilanes, so that the composition also cures reliably in areas that cannot be irradiated with actinic radiation but to which external moisture can penetrate.

[0036] In a third preferred embodiment, the compositions comprise, in addition to the components of the first and / or second embodiment, at least one radically curable compound (F) based on (meth)acrylates and a radical photoinitiator (G).

[0037] In all the above-mentioned embodiments, the compositions may additionally contain further additives (H) which are familiar to the person skilled in the art for use in moisture-curable compositions.

[0038] The components of the compositions according to the invention are described in detail below. The respective components can be combined with each other and with each other in any technically reasonable manner within the meaning of the invention. Component (A): Moisture-curing compounds (A1): Difunctional alkoxysilane compound

[0039] The moisture-curable compound of component (A) comprises one or more at least difunctional alkoxysilane compounds (A1).

[0040] The at least difunctional alkoxysilane compound with at least two alkoxysilane groups (A1) preferably corresponds to the general formula (I): in which R 1< is at least a divalent organic radical, each R 2< is independently a monovalent radical selected from the group consisting of hydrogen, linear, branched, cyclic, saturated, unsaturated and aromatic hydrocarbons, which may optionally be halogen-substituted and / or interrupted by 1 to 3 heteroatoms, each R 3< is independently a monovalent radical selected from the group consisting of linear, branched, cyclic, saturated, unsaturated and aromatic hydrocarbons, and which may optionally be halogen-substituted or interrupted by 1 to 3 heteroatoms, each R 4< is independently a monovalent radical selected from the group consisting of hydrogen, linear, branched, cyclic, saturated, unsaturated and aromatic hydrocarbons, which may optionally be halogen-substituted or interrupted by 1 to 3 heteroatoms, X is a heteroatom-containing di- or trivalent radical which may be substituted by a heteroatom, in particular oxygen,Nitrogen or sulfur, to which the group -CR 2< 2 -SiR 3< n (OR 4< ) (3-n) is bonded, m is at least 2, preferably 2 to 9, more preferably 2 to 4; and n = 0 to 2. ,

[0041] The compounds of general formula (I) are so-called α-(alkoxy)silane compounds, which are characterized by the (alkoxy)silane groups being located in the α-position to a heteroatom such as oxygen, sulfur, or nitrogen. The alkoxysilane group is separated from the heteroatom by a substituted or unsubstituted methylene group.

[0042] According to a preferred embodiment, R 1< is a radical selected from the group consisting of (i) linear or branched, saturated or unsaturated alkyl radicals having 1 to 8 C atoms, optionally interrupted by 1 to 3 heteroatoms, (ii) saturated or unsaturated cycloalkyl radicals having 3 to 9 C atoms, optionally interrupted by 1 to 3 heteroatoms, (iii) aromatic radicals having 5 to 10 C atoms or (iv) polyolefins, polyethers, polyamides, polyesters, polycarbonates, polyurethanes, polyureas, polybutadienes, hydrogenated polybutadienes, polysiloxanes or polyacrylates, where R 1< may in each case be unsubstituted or may carry further substituents.

[0043] More preferably, R 1< is a polymeric radical of the aforementioned group (iv), preferably with terminal alkoxysilane groups according to formula (I).

[0044] The radical R 1< particularly preferably represents a polymer backbone or copolymer backbone based on a polyether, polyester, polycarbonate, polyurethane, polyamide or polyurea, and more preferably a polyurethane or polyether radical.

[0045] The heteroatom-containing radical X preferably denotes a heteroatom-containing divalent radical, such as, for example, -O-, -S-, -N(R)-, -C(O)-O-, -OC(O)-O-, -OC(O)-ON(R)-, -N(R)-C(O)-O-, -S(O)-, -S(O) 2 -, -S(O)-O-, -S(O) 2 -O-, -OS(O) 2 -O-, -C(O)-N(R)-, -S(O) 2 -N(R)-, -S(O) 2 -N[C(O)R]-, -OS(O) 2 -N(R)-, -N(R)-S(O) 2 -O-, -P(O)(OR)-O-, -OP(O)(OR)-, -OP(O)(OR)-O-, -P(O)(OR)-N(R)-, -N(R)-P(O)(OR)-, -OP(O)(OR)-N(R)-, -N(R)-P(O)(OR)-O-, -N[C(O)R]-, -N=C(R)-O-, -C(R)=NO-, -C(O)-N[C(O)R]-, -N[S(O) 2 R']-, -C(O)-N[S(O) 2 R']- or -N[P(O)R" 2 ]-, where R is hydrogen or optionally substituted C 1 -C 20 alkyl or C 6 -C 20 aryl radicals, R' is an optionally substituted C 1 -C 20 alkyl or C 6 -C 20 aryl radical, and R" is an optionally substituted C 1 -C 20 alkyl, C 6 -C 20 aryl, C 1 -C 20 alkoxy or C 6 -C 20 aryloxy radical.

[0046] Particularly preferably, X in the general formula (I) represents an oxygen or nitrogen atom or a carboxy, carbamate, carbonate, ureido, urethane or sulfonate bond.

[0047] R 2< is preferably hydrogen. R 3< is preferably C 1 -C 6 alkyl, especially methyl or ethyl, or phenyl.

[0048] The radical R 4< in general formula (I) preferably represents a methyl or ethyl group. Preferably, n = 0 or 1. Furthermore, two radicals R 4< can be bridged to form a ring.

[0049] According to a further preferred embodiment, the radical R 2< is hydrogen, R 3< and R 4< are methyl groups and n = 1.

[0050] The at least difunctional α-alkoxysilane compounds preferably have an average molecular weight of 2,000 to 50,000 g / mol, very particularly preferably about 10,000 to 20,000 g / mol.

[0051] The preparation of α-alkoxysilane-terminated compounds is described in detail in WO 03 / 014226 A1, among others. In addition, many of the preferred α-silanes based on polyethers or polyurethanes are commercially available from Wacker Chemie AG. These are marketed under the brand name GENIOSIL STP-E. Examples include the types STP-E10 and STP-E30.

[0052] In a further embodiment, component (A1), optionally in addition to or instead of the silane compound of formula (I) having at least two α-alkoxysilane groups, may also comprise one or more at least difunctional alkoxysilane compounds of general formula (II): wherein R 1< , R 2< , R 3< and R 4< have the meanings given above for formula (I); X is a heteroatom-containing di- or trivalent radical which is bonded to the group -(CR 2< 2 ) y -SiR 3< n (OR 4< ) (3-n) through a heteroatom, in particular oxygen, nitrogen or sulfur, n = 0 to 2, q is at least 2, preferably 2 to 9, more preferably 2 to 4; and y is a number from 2 to 6.

[0053] In the preferred compounds of the general formula (II), y = 3. These compounds are so-called γ-alkoxysilanes, in which the heteroatom of the radical X is separated from the silicon atom of the alkoxysilane group by an optionally substituted propylene unit.

[0054] The preparation of γ-alkoxysilanes is described in detail, for example, in US Pat. No. 5,364,955 A and the documents cited therein. γ-alkoxysilanes of the general formula (II) with at least two alkoxysilane-containing end groups are commercially available from Wacker Chemie AG. Such γ-silane-terminated polyethers are available under the names Geniosil STP-E15 and STP-E35.

[0055] Component (A1) may be composed of one or more compounds of the general formulas (I) and / or (II). Component (A2): Monofunctional silane compound

[0056] In addition to component (A1), the compositions of the invention may additionally contain at least one monofunctional silane compound (A2) having only one alkoxysilane group and / or derivatives thereof. In particular, component (A2) may comprise partially condensed or bridged, particularly cyclically bridged, derivatives of the monofunctional silane compound, which are obtainable by partial hydrolysis of the alkoxysilane groups or by reacting the alkoxysilane groups with dihydric alcohols.

[0057] Component (A2) preferably comprises compounds of the general formula (III): wherein R 3< and R 4< have the meanings given above in connection with formula (I); R 5< is independently a monovalent organic radical which is selected from the group of linear, branched, cyclic, saturated, unsaturated and aromatic hydrocarbons and can optionally be substituted by heteroatoms and / or interrupted by heteroatoms and is different from R 3<; R 6< is a Si radical to which further radicals according to formula (III) can be linked, o is an integer from 0 to 3, p is an integer from 1 to 3, s is an integer from 0 to 3 and r is an integer from 0 to 2, where the sum of o + p + r + s = 4.

[0058] Preferably, o is 0 or 1, p is 2 or 3, s is 1 and r is 0 or 1.

[0059] Also included are partially condensed or bridged silane compounds of formula (III).

[0060] The monofunctional silane compound of component (A2) protects the compositions according to the invention from penetrating moisture during production and storage and additionally contributes to the build-up of adhesion during curing of the compositions.

[0061] In addition to classical alkoxyvinylsilanes, various monofunctional, preferably monomeric, α- or γ-alkoxysilanes can be used as component (A2).

[0062] Preferred examples from the group of α-silanes include (methacryloxymethyl)methyldimethoxysilane, methacryloxymethyltrimethoxysilane, N-trimethoxysilylmethyl-O-methylcarbamate and N-dimethoxy(methyl)silyl-methyl-O-methylcarbamate.

[0063] Examples of commercially available monofunctional α-alkoxysilanes include products from Wacker Chemie AG. Corresponding methacrylate- or carbamate-functionalized α-alkoxysilanes are available under the names GENIOSIL XL 32, XL 33, XL 63, or XL 65.

[0064] Partially condensed monofunctional silanes can also be used as moisture scavengers. For this purpose, monofunctional silanes such as Geniosil XL10 (VTMO) are reacted with a defined amount of water. Such products are commercially available, for example, under the name Dynasylan 6490 from Evonik Industries AG.

[0065] Alkoxysilanes, optionally cyclically bridged with difunctional alcohols, can also be used as component (A2). Such products are commercially available from Momentive under the name Silquest Y-15866.

[0066] Furthermore, the use of silanes as component (A2) is preferred, as they can fulfil a multiple function as moisture scavengers and adhesion promoters.

[0067] A combination of several different silanes according to the general formula (III) and their partially condensed or bridged derivatives is also within the meaning of the invention.

[0068] However, the use of silanes, which act as crosslinking catalysts in the presence of moisture and thus catalyze the curing of the composition, is not preferred. This group includes, in particular, aminosilanes, as described, for example, in EP 1 421 129 A. Examples include γ-aminopropyltrimethoxysilane or N-aminoethyl-3-aminopropyltrimethoxysilane. Therefore, the composition according to the invention is preferably free of aminosilanes.

[0069] In addition to compounds (A1) and (A2), poly(organo)siloxanes with curable alkoxysilane groups and / or curable acetyl groups (A3) can also be used in the moisture-curable component (A). These are not further restricted in their chemical structure and include, for example, cyclic polysiloxanes, linear polysiloxanes, crosslinked and branched polysiloxanes.

[0070] In the compositions of the present invention, component (A), based on the total weight of the composition comprising components (A) to (H), is preferably present in a range from 5 to 99.5 wt.%, more preferably from 10 to 99 wt.% and particularly preferably from 20 to 98 wt.%. Component (B): Acid former

[0071] In addition to the moisture-curable compounds of component (A), the compositions of the invention additionally contain at least one acid generator (B). The acid generator preferably comprises compounds capable of releasing a strong acid upon exposure to actinic radiation. Such compounds are also referred to below as photolatent acids. The released acid catalyzes the hydrolysis and crosslinking of the moisture-curing moieties present in the composition. In addition, the released acid also catalyzes the formation of acetals / ketals, thioacetals, and / or thioketals by reacting component (C) with alcohols or thiols present in the formulation and / or released from the moisture-curable compounds of component (A) by hydrolysis.The conversion of component (C) to acetals or ketals releases water from the mass, which in turn is available for moisture curing of component (A). This allows for complete curing within a short time, even of thick layers. The release of water occurs only in areas accessible to irradiation.

[0072] Suitable photolatent acids are known, among other things, from cationically polymerizable systems. Aromatic arylsulfonium salts, as described in WO 2003 / 072567 A1 or WO 2003 / 008404 A1, or aryliodonium salts, as described in WO 1998 / 002493 A1 or US Pat. No. 6,306,555 A, can be used.

[0073] Onium salts suitable as photolatent acids are also described by JV Crivello and K. Dietliker in "Photoinitiators for Free Radical, Cationic & Anionic Photopolymerisation", Volume III of "Chemistry & Technology of UV & EB Formulation for Coatings, Inks & Paints", 2nd Ed., J. Wiley and Sons / SITA Technology (London), 1998.

[0074] Examples of different anions of the sulfonium or iodonium salts are HSO 4 -< , PF 6 -< , SbF 6 -< , AsF 6 -< , Cl -< , Br, I -< , ClO 4 -< , PO 4 -< , SO 3 CF 3 -< , tosylate or a borate anion, such as BF 4 -< and B(C 6 F 5 ) 4 -<.

[0075] Also suitable are photolatent acids based on aluminate anions as disclosed in EP 3 184 569 A1 or WO 2017 035 551 A1.

[0076] Triarylsulfonium-based photoinitiators commercially available as photolatent acids are available under the brand names Chivacure 1176 from Chitech, Irgacure PAG 290 from BASF, or UVI-6976 and UVI-6974 from Dow Chemical Co.

[0077] Diaryliodonium-based photoinitiators commercially available as photolatent acids are available, among others, under the brand names UV1242 or UV2257 from Deuteron and Bluesil 2074 from Bluestar.

[0078] In addition to photolatent acids based on iodonium and sulfonium ions, non-ionic photolatent acids can also be used in the compositions of the invention. Such compounds based on oxime esters and oximesulfonic acid esters are described in WO 2013 / 083505 A1 and EP 1 124 832 A1. Commercially available non-ionic photolatent acids based on oximesulfonic acid esters are available from BASF under the names Irgacure PAG 103, Irgacure PAG 121, Irgacure PAG 203, and CGI 1907, among others.

[0079] Furthermore, trichloromethyl triazine compounds or benzoin esters can also be used as non-ionic photolatent acids as component (B).

[0080] The photolatent acid used as acid generator in the compositions according to the invention is preferably activatable by actinic radiation having a wavelength of 200 to 480 nm, particularly preferably at a wavelength of 320 to 480 nm. If necessary, the photolatent acid can be combined with a suitable sensitizer.

[0081] Particularly preferred in the present invention is the use of the described non-ionic photolatent acids as component (B).

[0082] The above lists are to be seen as examples for the acid former (B) and should not be understood as limiting.

[0083] It has been shown that even very low concentrations of component (B) are sufficient to activate the compound with the release of water and subsequently achieve complete curing. This represents a further advantage given the high cost of the corresponding acid generators. Furthermore, even small amounts of released acid are sufficient to catalyze moisture curing by crosslinking component (A). Additional catalysts for moisture curing are therefore not absolutely necessary, but can be used optionally.

[0084] In the moisture-curable compositions of the present invention, the acid generator (B), based on the total weight of the composition comprising components (A) to (H), is preferably present in a proportion of 0.0001 to 5% by weight, but particularly preferably in proportions of at least 0.001% by weight, and / or preferably of at most 3% by weight, further preferably of at most 1% by weight or of at most 0.5% by weight and very particularly preferably of at most 0.3% by weight.

[0085] The use of particularly low concentrations of the acid generator (B) is particularly advantageous when non-ionic photoinitiators are used

[0086] It is also possible to use more than one photolatent acid generator in the compositions according to the invention. Component (C): Carbonyl compound

[0087] In addition to components (A) and (B), the compositions of the invention further contain, as component (C), at least one carbonyl compound or carbonyl derivative selected from the group of aldehydes, ketones, hemiacetals, and / or hemiketals. These can release water under acid catalysis in the presence of alcohols and / or thiols.

[0088] According to a preferred embodiment, component (C) comprises at least one carbonyl compound from the group of aldehydes and ketones. The aldehydes and ketones according to the invention are not further restricted in their chemical structure and functionality. Aliphatic, cycloaliphatic, aromatic aldehydes or ketones bearing one or more carbonyl groups can be used.

[0089] Examples of suitable aldehydes include formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde, caproaldehyde, enanthaldehyde, caprylaldehyde, decanal, 2-ethylhexanal, 2-methylpentanal, 3-formylpinane, glyoxal, glutaraldehyde, pivaldehyde, acrolein, furfural, benzaldehyde, anisaldehyde, cinnamaldehyde, citral, citronellal, cuminaldehyde, dimethylbenzaldehyde, veratraldehyde, farnesal, 3-(2-furyl)acrolein, α-hexylcinnamaldehyde, hydroxycitronellal, methional, 5-methyl-2-phenyl-2-hexenal, piperonal, salicylaldehyde and safranal, as well as combinations thereof.

[0090] Examples of suitable ketones include acetone, diethyl ketone, cyclopentanone, cyclohexanone, 2-octanone, acetanisole, acetoin, acetophenone, acetovanillone, benzophenone, benzylideneacetone, 2-butanone, butyrophenone, camphor, 2-decanone, ethyl acetoacetate, ethyl pyruvate, ionone, isophorone, mesityl oxide and 2,3-pentanedione, as well as combinations thereof.

[0091] The carbonyl compounds mentioned are often compounds used in the flavor and fragrance industry. They are therefore characterized by high availability and often low toxicity. Furthermore, they possess an olfactory note.

[0092] The use of aldehydes in component (C) is particularly preferred, as they exhibit higher reactivity than ketones in acetal formation and release water more rapidly in the compositions of the invention. The use of aldehydes can thus significantly shorten the time required for curing the compositions of the invention. In particular, moisture-curable compositions can be provided that completely cure in the irradiated areas within 24 hours after irradiation, in particular within a maximum of six hours.

[0093] In addition to aldehydes and ketones as component (C), their derivatives in the form of partial reaction products with alcohols and / or thiols (hemiacetals or hemiketals) can also be used.

[0094] Examples of suitable hemiacetals and / or hemiketals of component (C) are carbohydrates, in particular sugars.

[0095] The combination of several carbonyl compounds (C) with each other or with hemiacetals and / or hemiketals is also within the meaning of the invention.

[0096] To reduce the proportion of low-molecular-weight components in the compositions according to the invention that can outgas from the compositions, the use of higher-molecular-weight carbonyl compounds is also conceivable. For example, polymers bearing reactive aldehyde and / or ketone groups can also be used.

[0097] Likewise, hybrid compounds can be used which have both silane functionalities and suitable carbonyl groups in order to reduce the outgassing of component (C) from the compositions according to the invention, since these can be incorporated into the silane network.

[0098] In the compositions of the present invention, component (C), based on the total weight of the composition comprising components (A) to (H), is preferably present in a range from 0.1 to 20 wt.%, more preferably from 0.3 to 15 wt.% and particularly preferably from 0.5 to 10 wt.%. Component (D): Alcohol and / or Thiol

[0099] In addition to components (A) to (C), the compositions of the invention may optionally contain an alcohol and / or a thiol. The presence of component (D) accelerates the release of water and thus further shortens the time required for the compositions to cure after activation.

[0100] The alcohols or thiols which can be used in the compositions according to the invention are not further restricted in their chemical structure; they can be aliphatic, cycloaliphatic or aromatic.

[0101] The use of difunctional aliphatic short-chain alcohols and / or thiols is particularly preferred. The use of 1,2- and 1,3-substituted dialcohols, which are capable of forming cyclic acetals, is particularly preferred. Aliphatic alcohols with 1 to 12 carbon atoms are particularly preferred.

[0102] Examples of suitable alcohols and thiols include the following compounds: methanol, ethanol, propanol, isopropanol, ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 2-ethylhexanol, 2-ethyl-1,3-hexanediol, 1-octanol, glycerin, 1,2-ethylene glycol, 1-propanethiol, 2-propanethiol, thiophenol, ethanethiol, octanethiol, dodecanethiol, mercaptoethanol, and ethanedithiol.

[0103] Higher molecular weight alcohols and / or thiols are also within the scope of the invention. For example, alcohols based on polycarbonates, polyesters, or preferably polyethers can be used. These are commercially available under the trade names Synalox or Acclaim from Dow Chemical or Covestro. Such higher molecular weight alcohols can also function as plasticizers in the formulation.

[0104] The combination of several thiols and / or alcohols is also within the meaning of the invention.

[0105] Likewise, hybrid compounds containing both silane functionalities and suitable alcohol and / or thiol groups can be used as component (D) to reduce the outgassing of low-molecular-weight compounds from the compositions of the invention. Due to the silane functionality, the hybrid compounds can be easily incorporated into the silane network.

[0106] In the compositions of the present invention, component (D), based on the total weight of the composition comprising components (A) to (H), is preferably present in a range from 0 to 50% by weight, more preferably from 0 to 30% by weight and particularly preferably from 0 to 20% by weight, or from 0.1 to 20% by weight. Component (E): Catalyst

[0107] In the second preferred embodiment, the compositions according to the invention additionally comprise, as component (E), at least one catalyst for silane crosslinking.

[0108] Organometallic compounds based on lead, iron, titanium, zinc, tin, bismuth, cobalt, zirconium, vanadium, and nickel can be used as catalysts. Compounds such as dibutyltin laurate, dibutyltin diacetate, dibutyltin oxide, tetrabutyl titanate, iron acetylacetonate, cobalt naphthenate, and lead dioctate are particularly suitable.

[0109] Acidic catalysts such as carboxylic acids, phosphoric acids, boric acids, and sulfonic acids can also be used as catalysts. Lewis acids such as trimethylsilyltrifluoromethanesulfonic acid or trimethylsilyl chloride can also be used. (Meth)acrylic acid, maleic acid, acetic acid, toluenesulfonic acid, trifluoromethanesulfonic acid, and itaconic acid are particularly suitable.

[0110] Furthermore, polymeric compounds with corresponding acid groups are also suitable as catalysts (E).

[0111] The acid strength of the acid catalyst (E) is preferably at least three p K s units weaker than the acid strength of the acid formed from the acid generator (B) after irradiation.

[0112] Less preferred are basic catalysts, for example those based on amines, since these can trap the acid released from the photolatent acid (B) and thus hinder the release of water.

[0113] The above list is intended as an example and not exhaustive. The use of multiple catalysts is also within the scope of the invention.

[0114] In the second embodiment of the compositions according to the invention, preferably 0.01 to 20 percent by weight, particularly preferably 0.1 to 5 percent by weight of component (E) are used, here based on the total weight of the composition comprising components (A) to (H). Component (F): Radiation-curable compound

[0115] In a third preferred embodiment, the compositions of the invention additionally comprise at least one radiation-curing compound (F). This compound is not further restricted with regard to its basic chemical structure (e.g., aromatic, aliphatic, cycloaliphatic). Preferably, the radiation-curing compound (F) comprises at least one (meth)acrylate.

[0116] The term "(meth)acrylate" and equivalent terms here and below refer to derivatives of acrylic acid, methacrylic acid, and mixtures thereof.

[0117] Suitable radiation-curable compounds (F) include, for example: isobornyl acrylate, stearyl acrylate, tetrahydrofurfuryl acrylate, cyclohexyl acrylate, 3,3,5-trimethylcyclohexanol acrylate, behenyl acrylate, 2-methoxyethyl acrylate and other mono- or polyalkoxylated alkyl acrylates, isobutyl acrylate, isooctyl acrylate, lauryl acrylate, tridecyl acrylate, isostearyl acrylate, 2-(o-phenylphenoxy)ethyl acrylate, acryloylmorpholine, N,N-dimethylacrylamide, 4-butanediol diacrylate, 1,6-hexanediol diacrylate, 1,10-decanediol diacrylate, tricyclodecanedimethanol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, polybutadiene diacrylate, cyclohexanedimethanol diacrylate, diurethane acrylates of monomeric, oligomeric or polymeric diols and polyols, trimethylolpropane triacrylate (TMPTA), and dipentaerythritol hexaacrylate (DPHA), and combinations thereof. Higher-functional acrylates derived from multiply branched or dendrimeric alcohols can also be used advantageously.

[0118] The analogous methacrylates are also within the meaning of the invention.

[0119] As higher molecular weight radiation-curable compounds, urethane acrylates based on polyesters, polyethers, polycarbonate diols and / or (hydrogenated) polybutadiene diols can be used as component (F).

[0120] (Meth)acrylates with free acid groups can act both as radiation-curable component (F) in the compositions according to the invention and as acid catalyst (E) to catalyze silane crosslinking.

[0121] A combination of several radiation-curable compounds is also within the meaning of the invention.

[0122] The radiation-curing compound (F) is preferably present in the compositions of the third embodiment according to the invention in a proportion of 3 to 80 percent by weight, particularly preferably in a proportion of 5 to 50 percent by weight, based on the total weight of the composition comprising components (A) to (H). Component (G): Radical photoinitiator

[0123] In addition to the radiation-curable compound (F), the compositions of the third embodiment of the invention also contain a photoinitiator (G) for activating the radical polymerization. The usual, commercially available compounds can be used as radical photoinitiators, such as α-hydroxyketones, benzophenone, α,α'-diethoxyacetophenone, 4,4-diethylaminobenzophenone, 2,2-dimethoxy-2-phenylacetophenone, 4-isopropylphenyl-2-hydroxy-2-propyl ketone, 1-hydroxycyclohexylphenyl ketone, isoamyl-p-dimethylaminobenzoate, methyl-4-dimethylaminobenzoate, methyl-o-benzoylbenzoate, benzoin, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-isopropylthioxanthone, dibenzosuberone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bisacylphosphine oxides, wherein the photoinitiators mentioned can be used alone or in combination of two or more of the mentioned compounds can be used.

[0124] The IRGACURE ™< grades from BASF SE can be used as UV photoinitiators, for example the grades IRGACURE 184, IRGACURE 500, IRGACURE 1179, IRGACURE 2959, IRGACURE 745, IRGACURE 651, IRGACURE 369, IRGACURE 907, IRGACURE 1300, IRGACURE 819, IRGACURE 819DW, IRGACURE 2022, IRGACURE 2100, IRGACURE 784, IRGACURE 250, IRGACURE TPO, IRGACURE TPO-L. Furthermore, the DAROCUR ™< grades from BASF SE can be used, such as the grades DAROCUR MBF, DAROCUR 1173, DAROCUR TPO and DAROCUR 4265.

[0125] The radical photoinitiator used as component (G) in the compositions according to the invention is preferably activatable by actinic radiation having a wavelength of 200 to 600 nm, particularly preferably 320 to 480 nm. If necessary, the photoinitiator can be combined with a suitable sensitizer.

[0126] The photoinitiator (G) is preferably present in the compositions according to the invention of the third embodiment in a proportion of 0.01 to 5% by weight, based on the total weight of the composition comprising components (A) to (H). Component (H): Additives

[0127] The described compositions may further contain optional components as additives (H). The additives (H) are preferably selected from the group of fillers, dyes, pigments, anti-aging agents, fluorescent agents, stabilizers, accelerators, photosensitizers, adhesion promoters, moisture scavengers, crosslinkers, flow improvers, wetting agents, thixotropic agents, diluents, flexibilizers, polymeric thickeners, flame retardants, corrosion inhibitors, plasticizers, and tackifiers.

[0128] The above list of additives is to be considered as exemplary and in no way limiting.

[0129] The additives of component (H) are preferably present in the compositions according to the invention in a proportion of 0 to 70% by weight, based on the total weight of components (A) to (H). Formulation of the compositions according to the invention

[0130] The one-component compositions according to the invention preferably have the following composition, based in each case on the total weight of components (A) to (H): (A) at least one moisture-curable compound in a proportion of 10 to 99 wt. %, wherein the moisture-curable compound comprises at least one difunctional alkoxysilane (A1) and optionally one monofunctional alkoxysilane (A2); (B) at least one acid generator in a proportion of 0.0001 to 3 wt. %, preferably 0.001 to 1 wt. %; (C) at least one carbonyl compound and / or a carbonyl derivative in a proportion of 0.3 to 15 wt. %; (D) at least one compound from the group of alcohols and / or thiols in a proportion of 0 to 30 wt. %, or preferably 0.1 to 20 wt. %; (E) at least one catalyst for silane crosslinking in a proportion of 0 to 20 wt. %, preferably 0.1 to 5 wt. %; more preferably in the form of an acidic catalyst; (F) at least one radiation-curable compound in a proportion of 0 to 50 wt.%, preferably 5 to 50 wt.%; (G) at least one radical photoinitiator in a proportion of 0 to 5 wt.%.-%, preferably 0.01 to 5 wt.%; and (H) at least one additive (H) in a proportion of 0 to 70 wt.%; preferably selected from the group of fillers, dyes, pigments, photosensitizers, age inhibitors, fluorescent agents, stabilizers, moisture scavengers, accelerators, adhesion promoters, crosslinkers, flow improvers, wetting agents, thixotropic agents, diluents, flexibilizers, polymeric thickeners, flame retardants, corrosion inhibitors, plasticizers and tackifiers, alone or in combination with one another.

[0131] A formulation of the one-component composition according to the invention in a first preferred embodiment comprises the following components, each based on the total weight of components (A) to (H): (A) 10 to 99 wt.% of the moisture-curable compound, wherein the moisture-curable compound comprises at least one difunctional alkoxysilane (A1) and optionally one monofunctional alkoxysilane (A2); (B) 0.0001 to 3 wt.%, preferably 0.001 to 1 wt.%, of the at least one acid generator (B); (C) 0.3-15 wt.% of the at least one carbonyl compound (C); (D) 0 to 30 wt.% of the at least one alcohol (D), or preferably 0.1 to 20 wt.%; and (H) 0 to 70 wt.% of the at least one additive.

[0132] The composition according to the invention of the first embodiment is preferably free of catalysts (E) for silane crosslinking and also contains no radiation-curing compound (F) and no radical photoinitiator (G). The composition thus preferably consists of components (A), (B), (C), and optionally at least one of components (D) and (H).

[0133] A formulation of the one-component composition according to the invention according to a second preferred embodiment comprises the following components, each based on the total weight of components (A) to (H): (A) 10 to 99 wt.% of the moisture-curable compound (A), wherein the moisture-curable compound comprises at least one difunctional alkoxysilane (A1) and optionally one monofunctional alkoxysilane (A2); (B) 0.0001 to 3 wt.%, preferably 0.001 to 1 wt.%, of the at least one acid generator (B); (C) 0.3-15 wt.% of the at least one carbonyl compound (C); (D) 0 to 30 wt.% of the at least one alcohol (D), or preferably 0.1 to 20 wt.%; (E) 0.01 to 20 wt.% of the at least one catalyst (E), preferably an acidic catalyst; and (H) 0 to 70 wt.% of the at least one additive.

[0134] A formulation of the one-component composition according to the invention according to a third preferred embodiment comprises the following components, each based on the total weight of components (A) to (H): (A) 10 to 90 wt. % of the moisture-curable compound (A), wherein the moisture-curable compound comprises at least one difunctional alkoxysilane (A1) and optionally one monofunctional alkoxysilane (A2); (B) 0.0001 to 3 wt. %, preferably 0.001 to 1 wt. %, of the at least one acid generator (B); (C) 0.3-15 wt. % of the at least one carbonyl compound (C); (D) 0 to 20 wt. % of the at least one alcohol (D), or preferably 0.1 to 20 wt. %; (E) 0 to 20 wt. % of the at least one catalyst for silane crosslinking (E), preferably an acidic catalyst; (F) 5 to 50 wt. % of the at least one radiation-curable compound (F) based on (meth)acrylates; (G) 0.01 to 5 wt.% of the at least one photoinitiator (G) for the radical polymerization; and (H) 0 to 70 wt.% of the at least one additive.

[0135] The compositions according to the invention preferably consist of the components specified above for the respective embodiments.

[0136] Surprisingly, it has been found that the compositions of the invention exhibit rapid moisture curing even in high layer thicknesses without an additional alcohol and / or a thiol (D). Radiation-induced hydrolysis of the alkoxysilane groups of component (A) results in the release of the corresponding alcohols from the alkoxy groups, which are subsequently available for the acetalization or ketalization of the carbonyl compound (C).

[0137] By adding alcohols and / or thiols as a separate component (D), the moisture curing of the compositions according to the invention can be further accelerated. Use of the compositions according to the invention

[0138] The compositions of the invention can be activated by actinic radiation and cured by moisture. In contrast to the prior art, the compositions of the invention cure largely independently of the ambient humidity and the applied layer thickness. These compositions are distinguished from the prior art in that water release is possible efficiently by irradiation, without additional heat input. Of course, the crosslinking reaction can be further accelerated by optional heat input.

[0139] The release of an acid from component (B) by irradiation induces both the release of water in the masses and the crosslinking of the moisture-curable alkoxysilane groups.

[0140] After irradiation, the compounds cure within seven days at room temperature; preferably within 24 hours and most preferably within 6 hours, even if external moisture is excluded.

[0141] The curing rate depends significantly on the equivalent ratio of all silane-bonded alkoxy groups in the moisture-curable components (A) to the equivalents of the carbonyl compounds in component (C). The compositions according to the invention are preferably formulated such that, per equivalent of silane-bonded alkoxy groups in component (A), there are 0.01 to 3 equivalents of carbonyl groups in component (C), preferably 0.05 to 2 equivalents, and particularly preferably 0.1 to 1 equivalent of carbonyl groups.

[0142] Preferably, the masses are activated immediately before application or after application to a substrate.

[0143] Activation of the mass immediately before application can be achieved by irradiating the mass in a flow-through activation apparatus. Suitable dosing devices for flow-through activation of the masses by irradiation are described in DE 3 702 999 A and DE 10 2007 017 842 A1.

[0144] It is essential that the residence time of the mass after activation in a dosing device does not exceed the open time of the activated mass.

[0145] According to a preferred embodiment, a method for bonding, molding, sealing and coating substrates using the composition according to the invention is provided, which comprises the following steps a) Dosing the mass onto a first substrate; b) activating the mass by irradiating it with actinic radiation of a suitable wavelength for a sufficiently long period of time so that an acid is released from the acid generator; c) optionally adding a second substrate to the activated mass within an open time to form a substrate composite; d) maintaining a waiting time until the mass reaches an initial strength on the substrate or in the substrate composite.

[0146] The described process can also be carried out in a flow-through activation apparatus or a radiant storage vessel. In these cases, step b) takes place before step a). It is important that the irradiated mass is not exposed to excessive standing times within the apparatus or storage vessel, as otherwise the mass can harden in the apparatus even without moisture ingress.

[0147] In the case of two or more joining partners, of which at least one is transmissible, the activation step b) can also be carried out after step c).

[0148] The compositions according to the invention are particularly suitable as adhesives or sealants for bonding, molding, sealing and coating any substrates. Measurement methods and definitions used Irradiation

[0149] A DELOLUX 20 LED lamp from DELO Industrie Klebstoffe GmbH & Co. KGaA with a wavelength of 460 nm was used for irradiation. The compounds were irradiated in the cartridge at an intensity of 200 ± 20 mW / cm². The cartridge was irradiated from two sides for 60 s each. Curing

[0150] "Crosslinking" or "curing" is defined as a polymerization, condensation, or addition reaction beyond the gel point. The gel point is the point at which the storage modulus G' becomes equal to the loss modulus G". To assess curing (solid vs. liquid), the activated compound in the cartridges is squeezed out and subjected to a haptic test with a plastic spatula. If it was no longer possible to squeeze out the compound, the consistency of the compound was tested using a toothpick via the cartridge tip. Room temperature

[0151] Room temperature is defined as 23 ± 2 °C. viscosity

[0152] The viscosity of the compounds was measured using an Anton Paar Physica MCR302 rheometer equipped with a standardized PP20 measuring cone with a 200 µm gap at 23 °C and a shear rate of 10 / second. To assess storage stability, the viscosity measurement was repeated at room temperature after 7 days of storage of the compounds at room temperature, protected from light and moisture. A viscosity change of less than 10% from the initial value is considered excellent (++), less than 25% is considered very good (+), less than 50% is considered good (○), less than 100% is considered sufficient (-), and greater than 100% is considered unsatisfactory (--). cartridges

[0153] The cartridges used were 5 ml translucent SEMCO cartridges from PPG Industries. Evidence and extent of water release

[0154] The extent of water release was determined in accordance with DIN 53715. A test system consisting of 15 parts by weight of benzaldehyde, 36.2 parts of methanol, 0.1 part of a photolatent acid (Irgacure PAG 103), and 48.7 parts of toluene was prepared under the exclusion of light below 500 nm, and the components were mixed together. The system was free of moisture-curing compounds. The clear, yellow solution was first subjected to a Karl Fischer analysis without prior irradiation. A sample was then irradiated with light with a wavelength of 400 nm (DELOLUX 80 irradiation lamp) and an intensity of 1000 mW / cm² for 4 minutes while stirring. Further Karl Fischer analyses were performed on the irradiated sample immediately afterward and after 2 hours. The water content was 0.11 wt% before irradiation and 1.46 wt% immediately after irradiation and 1.54 wt% after 2 h.

[0155] This shows that in a system consisting of photolatent acid, carbonyl compound and alcohol, a significant amount of water can be generated by irradiation. Manufacturing examples

[0156] The following components were used to produce the one-component masses according to the examples given below: Component (A): moisture-curing compounds (A1): Difunctional silane compound (A1-1) Geniosil STP-E 10 (available from Wacker Chemie AG) (A1-2) Geniosil STP-E 15 (available from Wacker Chemie AG) (A2): Monofunctional silane compound (A2-1) Geniosil XL 33 (available from Wacker Chemie AG) (A2-2) Dynasylan VTMO (available from Evonik Industries AG) (AS-3) Geniosil XL 63 (available from Wacker Chemie AG) Component (B): Acid former (B1) Irgacure PAG 121 (available from BASF SE) Component (C): Carbonyl compound (C1) Benzaldehyde (available from Sigma Aldrich) (C2) Acetone (available from Sigma Aldrich) Component (D): alcohol, thiol(D1) Methanol (available from Sigma Aldrich) (D2) 1,3-Propanediol (available from Sigma Aldrich) Component (E): Catalyst (E1) Acrylic acid (available from Sigma Aldrich) Component (F): radiation-curable compound (F1) Isobornyl acrylate (IBOA; available from Sartomer) Component (G): Radical photoinitiator (G1) Speedcure TPO-L (available from Lambson) Component (H): Additives (H1) Plasticizer: OXSOFT TOTM (available from Oxea) (H2) Stabilizer: Irganox 1135 (available from BASF SE)

[0157] To prepare the compositions according to the invention, components (A) were initially introduced into a reaction vessel in the absence of light with wavelengths below 500 nm, and the acid generator (B) was dissolved at 50 °C for 15 minutes. Finally, the remaining components were added and incorporated using a dissolver. Comparative examples were prepared in an analogous manner.

[0158] The composition of the compositions according to the invention and the comparative examples is given in the following tables. The proportions are in each case percentages by weight based on the total weight of the composition comprising components (A) to (H).

[0159] Formulation of the compositions according to the invention Table 1 Components Comparison Examples according to the invention e.g. 1 1< 2 3 4 5 6 7 8 9 10 11 12 13 (A) Silane (A1-1) 65 98,4 94,15 65 65 65 65 65 65 65 65 65 - Silane (A1-2) - - - - - - - - - - - - 70 Silane (A2-1) 5 - - 5 5 5 5 5 5 5 5 5 - Silane (A2-2) 1,5 1,5 1,5 1,5 1,5 1,5 1,5 1,5 1,5 1,5 1,5 1,5 1,5 (B) (B1) 0,1 0,1 0,1 0,1 0,1 0,1 0,1 0,1 0,1 0,1 0,1 0,1 0,1 (C) Aldehyde (C1) - - 4,25 8,49 6,37 4,25 2,12 1,06 0,53 - - - 4,25 Ketone (C2) - - - - - - - - - 3,48 2,32 1,16 - (H) (H1) 28 - - 19,51 21,63 23,75 25,88 26,94 27,47 24,52 25,68 26,84 23,75 (H2) 0,4 - - 0,4 0,4 0,4 0,4 0,4 0,4 0,4 0,4 0,4 0,4 Properties of the masses Time to cure in the cartridge after irradiation (2*60s 460nm) at room temperature > 7 d, liquid > 7 d, liquid 140 minutes 30 minutes 50 minutes 140 minutes 240 minutes 24 h 7 d 21,5 h 45,5 h 7 d 24 h Storage stability Viscosity change after storage for 7 days at room temperature ++ ++ ++ ++ ++ ++ ++ ++ ++ ++ ++ ++ ++ 1< see DE 10 2016 111 590 A1 Table 2 Components Reference examples Comparison Examples according to the invention e.g. 7 12 14 15 16 17 18 19 20 (A) Silane (A1-1) 65 65 65 65 65 65 65 65 65 Silane (A2-1) 5 5 5 5 5 5 5 5 5 Silane (A2-2) 1,5 1,5 1,5 1,5 1,5 1,5 1,5 1,5 1,5 (B) (B1) 0,1 0,1 0,1 0,1 0,1 0,1 0,1 0,1 0,1 (C) Aldehyde (C1) 2,12 - - 2,12 2,12 2,12 2,12 2,12 - Ketone (C2) - 1,16 - - - - - - 1,16 (D) (D1) - - - 0,32 0,96 - - - - (D2) - - 2,28 - - 0,76 1,14 2,28 2,28 (H) (H1) 25,88 26,84 25,72 25,56 24,92 25,12 24,74 23,6 24,56 (H2) 0,4 0,4 0,4 0,4 0,4 0,4 0,4 0,4 0,4 Properties of the masses Time to cure in the cartridge after irradiation (2*60s 460nm) at room temperature 240 minutes 7 d > 7 d, liquid 180 minutes 180 minutes 30 minutes 10 minutes 20 minutes 30 minutes Storage stability ++ ++ ++ ++ ++ + + ++ ++ Viscosity change after storage for 7 days at room temperature Table 3 Components Examples according to the invention Comparison e.g. 21 22 23 (A) Silane (A1-1) 65 65 65 Silane (A2-1) 5 1 1 Silane (A2-2) 1,5 1,5 1,5 Silane (A2-3) - 0,5 0,5 (B) (B1) 0,1 0,1 0,1 (C) (C1) 4,25 4,25 - (E) (E1) 3 3 3 (F) (F1) - 7 7 (G) (G1) - 0,6 0,6 (H) (H1) 20,75 16,65 20,9 (H2) 0,4 0,4 0,4 Properties of the masses Time to cure in the cartridge after irradiation (2*60s 460nm) at room temperature 1 h 30 minutes > 7 d, liquid Storage stability + 0 ++ Viscosity change after storage for 7 days at room temperature Skin formation when stored open at 23°C / 50% relative humidity without irradiation 16 h 6 h 6 h

[0160] Inventive examples 3 to 9 in Table 1 contain an aldehyde as component (C). These formulations cure after irradiation within up to 7 days, even in the absence of external moisture, whereas comparative examples 1 and 2 remain liquid even after seven days in the absence of external moisture. The rate of curing can be controlled by the amount of aldehyde added. As shown in Examples 10 to 12, ketones also enable curing in the absence of external moisture. In addition to α-silane polymers, compositions containing exclusively γ-silane polymers as moisture-curable compounds can also be used, as shown in Example 13.

[0161] Table 2 shows the curing acceleration by adding alcohols as component (D). While a monofunctional alcohol in inventive examples 15 and 16 shows a slight acceleration compared to inventive example 7, the acceleration effect of a difunctional alcohol (D2), which is capable of forming a cyclic acetal, is clearly visible in examples 17 to 20. The addition of an alcohol in the absence of a carbonyl compound (C) shows no acceleration of moisture curing (Comparative Example 14).

[0162] Surprisingly, it is also possible to use a non-latent acid as catalyst (E) in the compositions according to the invention, as shown in Example 21, without significantly impairing storage stability (see Table 3). Here, too, after activation of the composition by irradiation, curing can occur within 1 hour with the exclusion of external moisture. However, this composition also cures without irradiation, but upon exposure to external moisture.

[0163] The composition of Example 22 additionally contains a radiation-curable compound (F) and a photoinitiator (G). The proportion of the radiation-curable compound (F) is selected such that the composition is still liquid shortly after irradiation and then cures within 30 minutes, whereas the composition according to Comparative Example 23, which does not contain a carbonyl compound as component (C), remains liquid under these conditions. Those skilled in the art will, of course, recognize that the proportions of the radiation-curable compounds (F) can also be selected such that the composition can be cured directly by the radical process, and moisture curing in the already gelled material progresses until the final strength is reached.

Claims

1. A moisture-curable one-pack composition that can be activated by irradiation with actinic radiation, comprising one or more moisture-curable compounds (A) selected from the group of alkoxy silanes, the alkoxy silane of component (A) being at least bifunctional with respect to alkoxy silane groups; at least one acid generator (B) releasing an acid when exposed to actinic radiation; and at least one carbonyl compound and / or carbonyl derivative (C) selected from the group of aldehydes, ketones, hemiacetals or hemiketals.

2. The one-pack composition according to claim 1, characterized in that the one-pack composition cures without the ingress of external moisture after activation of the composition by irradiation.

3. The one-pack composition according to claim 1 or 2, characterized in that the at least bifunctional alkoxy silane of component (A) comprises a bifunctional α-alkoxy silane.

4. The one-pack composition according to any one of the preceding claims, characterized in that the one-pack composition additionally comprises at least one catalyst (E) for silane crosslinking, preferably an acidic catalyst.

5. The one-pack composition according to any one of the preceding claims, characterized in that the one-pack composition additionally comprises at least one radiation-curable compound (F) and at least one radical photoinitiator (G).

6. The one-pack composition according to any one of the preceding claims, characterized in that the one-pack composition comprises at least one compound from the group of alcohols and / or thiols (D), preferably an aliphatic alcohol and / or an aliphatic thiol, more preferably a dialcohol and / or a dithiol, particularly preferably 1,2-dialcohols, 1,3-dialcohols, 1,2-dithiols or 1,3-dithiols, and mixtures thereof.

7. The one-pack composition according to any one of the preceding claims, comprising: (A) at least one moisture-curable compound in a proportion of 10 to 99 wt.%, wherein the moisture-curable compound comprises at least one bifunctional alkoxy silane (A1) and optionally a monofunctional alkoxy silane (A2); (B) at least one acid generator in a proportion of 0.0001 to 3 wt.%, preferably 0.001 to 1 wt.%; (C) at least one carbonyl compound and / or carbonyl derivative in a proportion of 0.3 to 15 wt.%; (D) at least one compound from the group of alcohols and / or thiols in a proportion of 0 to 30 wt.% or preferably 0.1 to 20 wt.%; (E) at least one catalyst for silane crosslinking in a proportion of 0 to 20 wt.%, preferably 0.1 to 5 wt.%; more preferably in the form of an acidic catalyst; (F) at least one radiation-curable compound in a proportion of 0 to 50 wt.%, preferably 5 to 50 wt.%; (G) at least one radical photoinitiator in a proportion of 0 to 5 wt.%, preferably 0.01 to 5 wt.%; and (H) at least one additive (H) in a proportion of 0 to 70 wt.%; preferably selected from the group of fillers, colorants, pigments, photosensitizers, anti-ageing agents, fluorescent agents, stabilizers, moisture scavengers, accelerators, adhesion promoters, crosslinking agents, flow improvers, wetting agents, thixotropic agents, diluents, flexibilizers, polymeric thickeners, flame retardants, corrosion inhibitors, plasticizers and tackifiers, alone or in combination with each other; each based on the total weight of components (A) to (H).

8. The one-pack composition according to claim 7, characterized in that the composition consists of components (A), (B), (C) and optionally at least one of components (D) and (H).

9. The one-pack composition according to claim 7, characterized in that the one-pack composition contains the at least one radiation-curable compound (F) in a proportion of 5 to 50 wt.% and the radical photoinitiator (G) in a proportion of 0.01 to 5 wt.%.

10. The one-pack composition according to any one of the preceding claims, characterized in that the composition, after activation by irradiation, cures in less than 7 days, preferably within 24 h and particularly preferably within at most 6 h.

11. The one-pack composition according to any one of the preceding claims, characterized in that the viscosity of the one-pack composition changes by less than 100% after a 7-day storage at room temperature, the viscosity being measured as defined in the description.

12. A use of the one-pack composition according to any of claims 1 to 11 as an adhesive or sealant for the bonding, casting, molding, sealing and coating of substrates.

13. A method for the bonding, molding, sealing and coating of substrates using the one-pack composition according to any of claims 1 to 11, comprising the following steps: a) dosing the one-pack composition onto a first substrate; b) activating the one-pack composition by irradiation with actinic radiation of a suitable wavelength during a sufficiently long period of time such that an acid is released from the acid generator (B); c) optionally supplying a second substrate to the activated one-pack composition within an open time while forming a substrate composite; and d) maintaining a waiting time until a first strength of the composition on the first substrate or in the substrate composite is achieved.

14. The method according to claim 13, characterized in that activation of the one-pack composition is performed in a flow apparatus.