WO2022048728A1 - Substances réticulables sur la base de polymères terminés par organyloxysilane - Google Patents

Substances réticulables sur la base de polymères terminés par organyloxysilane Download PDF

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WO2022048728A1
WO2022048728A1 PCT/EP2020/074327 EP2020074327W WO2022048728A1 WO 2022048728 A1 WO2022048728 A1 WO 2022048728A1 EP 2020074327 W EP2020074327 W EP 2020074327W WO 2022048728 A1 WO2022048728 A1 WO 2022048728A1
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optionally
weight
radical
parts
formula
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PCT/EP2020/074327
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German (de)
English (en)
Inventor
Niklas WIENKENHÖVER
Volker Stanjek
Richard Weidner
Lars Zander
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Wacker Chemie Ag
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Priority to EP20764998.9A priority Critical patent/EP4208492A1/fr
Priority to PCT/EP2020/074327 priority patent/WO2022048728A1/fr
Publication of WO2022048728A1 publication Critical patent/WO2022048728A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • 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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups

Definitions

  • the invention preferably relates to one-component, crosslinkable masses of silane-crosslinking prepolymers, processes for their production and their use as adhesives, sealants and coating materials, in particular for bonding substrates.
  • adhesives based on alkoxysilane -crosslinking polymers in the cured state not only have good adhesion properties on many substrates, but also very good mechanical properties, since they can have tear strength sufficient for many applications and high elasticity.
  • Another advantage of silane-crosslinking systems compared to numerous other adhesive and sealant technologies eg compared to isocyanate-crosslinking systems is the toxicological harmlessness of the prepolymers.
  • one-component systems (1K systems) are preferred, which harden on contact with atmospheric moisture.
  • the decisive advantages of one-component systems are, above all, their very easy application, as here, unlike with two-component systems, the user does not have to mix different adhesive components.
  • the time and labor savings and the safe In order to avoid possible dosing errors, with one-component systems there is also no need to process the adhesive or sealant within a mostly very narrow time window, as is the case with multi-component systems after the two components have been mixed.
  • transparent formulations can also be implemented.
  • special resins i.e. pure phenyl silicone resins or phenyl-methyl silicone mixed resins
  • other commercial silicone resins such as conventional methyl silicone resins, could not previously be used because they are not compatible with the usual alkoxysilane-crosslinking polymers.
  • the resulting mixtures are cloudy and, on the other hand, they do not exhibit the excellent properties described in DE102011081264.
  • the use of other silicone resins would be desirable for reasons of availability and - in the case of methyl silicone resins - the expected high hardness of corresponding formulations for certain target applications (e.g. paint applications).
  • the object of the present invention was therefore to provide hard, crosslinkable compositions based on methyl silicone resins which no longer have the abovementioned restrictions. Surprisingly, it was found that other silicone resins can also be used to produce hard formulations if the polydispersity M w /M n of the silicone resin does not exceed a certain limit.
  • the invention relates to crosslinkable compositions containing (A) 100 parts by weight of compounds of the formula whereby
  • Y is an x-valent polymer radical bonded via nitrogen, oxygen, sulfur or carbon
  • R can be the same or different and is a monovalent hydrocarbon radical optionally substituted with one or more halogen atoms
  • R 1 can be the same or different and represents a hydrogen atom or a monovalent hydrocarbon radical which is optionally substituted by one or more halogen atoms and which can be attached to the carbon atom via nitrogen, phosphorus, oxygen, sulfur or a carbonyl group,
  • R 2 can be the same or different and represents a hydrogen atom or a monovalent hydrocarbon radical optionally substituted by one or more halogen atoms
  • x is an integer from 1 to 10, preferably 1, 2 or 3, particularly preferably 1 or 2
  • a can be the same or different and is 0, 1 or 2, preferably 0 or 1
  • b can be the same or different and an integer from 1 to 10, preferably 1, 3 or 4, particularly preferably 1 or 3, in particular 1, is, (B) 5 to 2000 parts by weight of silicone resins containing units of the formula wherein
  • R 3 can be the same or different and is a hydrogen atom, a monovalent, SiC-bonded, optionally substituted by halogen atoms C1-C20 hydrocarbon radical or a divalent, optionally substituted by halogen atoms, aliphatic C1-C20 hydrocarbon radical, the two units of Formula (II) bridged, represents,
  • R 4 can be the same or different and is hydrogen or a monovalent C1-C20 hydrocarbon radical optionally substituted with halogen atoms, c is 0, 1, 2 or 3 and d is 0, 1, 2 or 3, with the proviso that that the sum of c+d is less than or equal to 3, c is 0 or 1 in at least 40% of the units of the formula (II) and the silicone resin has a polydispersity M w /M n of less than 5.0, optionally (C ) organosilicon compounds containing basic nitrogen, optionally (D) fillers, optionally (E) non-reactive plasticizers, optionally (F) catalysts, optionally (G) adhesion promoters, optionally (H) water scavengers, optionally (I) additives and optionally (J) aggregates.
  • radicals R are alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl; hexyl radicals, such as the n-hexyl radical; heptyl radicals, such as the n-heptyl radical; octyl radicals, such as the n-octyl radical, iso-octyl radicals and the 2,2,4-triethylpentyl radical/nonyl radicals, such as the n-nonyl radical; decyl radicals, such as the n-decyl radical; dodecyl radicals, such as the n-dodecyl radical; octadecyl radicals
  • substituted radicals R are haloalkyl radicals, such as the 3,3,3-trifluoro-n-propyl radical, the 2,2,2,2',2',2'-hexafluoroisopropyl radical and the heptafluoroisopropyl radical, and haloaryl radicals, such as the o-, m- and p-chlorophenyl radical.
  • the radical R is preferably a monovalent C1-C6 hydrocarbon radical which is optionally substituted with at least one halogen atom, the radical R being particularly preferably a C1-C2-alkyl radical, the radical R being very particularly preferably a methyl radical.
  • radicals R 1 are a hydrogen atom, the radicals specified for R and optionally substituted hydrocarbon radicals bonded to the carbon atom via nitrogen, phosphorus, oxygen, sulfur, carbon or a carbonyl group.
  • the radical R 1 is preferably a hydrogen atom or a hydrocarbon radical having 1 to 20 carbon atoms, particularly preferably a hydrogen atom.
  • radical R 2 are hydrogen atom and the examples given for radical R.
  • the radical R 2 is preferably a hydrogen atom or an alkyl radical having 1 to 10 carbon atoms which is unsubstituted or substituted by halogen atoms, particularly preferably an alkyl radical having 1 to 4 carbon atoms, in particular the methyl and ethyl radical.
  • organic polymers on which the polymer radical Y is based are to be understood as meaning all polymers in which at least 50%, preferably at least 70%, particularly preferably at least 90%, of all bonds in the main chain are carbon-carbon , carbon-nitrogen or carbon-oxygen bonds.
  • polymer residues Y are polyesters, polyethers, polyurethanes, polyalkylenes and polyacrylates.
  • the polymer radical Y is preferably an organic polymer radical which, as the polymer chain, is polyoxyalkylene, such as polyoxyethylene, polyoxypropylene, polyoxybutylene, polyoxytetramethylene, polyoxyethylene-polyoxypropylene copolymer and polyoxypropylene-polyoxybutylene copolymer; hydrocarbon polymers such as polyisobutylene and copolymers of polyisobutylene with isoprene; polychloroprenes; polyisoprenes; polyurethanes; Polyester; polyamides; polyacrylates; polymethacrylates; Contain vinyl polymer or polycarbonate and preferably about to the group or groups are bonded, where R' are the same or can be different and has a meaning given for R or represents a group -CH(COOR")-CH 2 -COOR" in which R" can be the same or different and has a meaning given for R.
  • polyoxyalkylene such as polyoxyethylene, polyoxypropylene, polyoxy
  • R' is preferably a -CH(COOR")-CH2-COOR” group or an optionally halogen-substituted hydrocarbon radical having 1 to 20 carbon atoms, particularly preferably a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms or an optionally halogen-substituted aryl group having 6 to 20 carbon atoms.
  • radicals R' are cyclohexyl, cyclopentyl, n-propyl and isopropyl radicals and n-, iso- and t-butyl radicals, the various stereoisomers of the pentyl radical, hexyl radical or heptyl radical and the phenyl radical.
  • the radicals R" are preferably alkyl groups having 1 to 10 carbon atoms, particularly preferably methyl, ethyl or propyl radicals.
  • the component (A) can have the groups attached in the manner described at any point in the polymer, such as chain and/or terminal.
  • the radical Y in formula (I) is particularly preferably an x-valent organic polymer radical bonded via nitrogen, oxygen, sulfur or carbon and containing polyurethanes or polyoxyalkylenes as the polymer chain, in particular polyurethane radicals with groups attached at the ends or polyoxyalkylene radicals with groups attached at the ends where the radicals and indices have the meanings given above.
  • the radicals Y are preferably linear or have 1 to 3 branching points, with particular preference being linear.
  • the polyurethane radicals Y can preferably be produced from linear or branched polyoxyalkylenes, in particular from polypropylene glycols, and di- or polyisocyanates.
  • the radicals Y preferably have mean molar masses M n (number average) of 400 to 30,000 g/mol, preferably of 4000 to 20,000 g/mol.
  • Suitable processes for producing a corresponding component (A) and also examples of component (A) itself are, inter alia, in EP 1093 482 B1 (paragraphs [0014]-[0023], [0039]-[0055] and example 1 and comparative example
  • EP 1641 854 B1 paragraphs [0014]-[0035], examples 4 and 6 and comparative examples 1 and 2), which are included in the disclosure content of the present application.
  • the polyoxyalkylene radicals Y preferably have average molar masses M n of from 4000 to 30000 g/mol, preferably from 8000 to 20000 g/mol.
  • Suitable processes for preparing a corresponding component (A) and also examples of component (A) itself are, inter alia, in EP 1535 940 B1 (paragraphs [0005]-[0025] and examples 1-3 and comparative example 1-4) or EP 1 896 523 B1 (paragraphs [0008]-[0047]), which are part of the disclosure content of the present application.
  • the end groups of the compounds (A) used according to the invention are preferably those of the general formulas where the radicals and indices have one of the meanings given above.
  • the compounds (A) are polyurethanes, which is preferred, they preferably have one or more end groups where R' has the meaning given above. If the compounds (A) are polypropylene glycols, which is particularly preferred, they preferably have one or more end groups the latter two end groups being particularly preferred.
  • Component (A) preferably has an average molar mass M n in the range of at least 400 g/mol, particularly preferably at least 4000 g/mol, in particular at least 10000 g/mol, and preferably at most 30000 g/mol, particularly preferably at most 20000 g/mol. mol, in particular at most 19000 g/mol.
  • Component (A) preferably has a viscosity in the range of at least 0.2 Pa s, preferably at least 1 Pa s, particularly preferably at least 5 Pa s, and preferably at most 700 Pa s, preferably at most 100 Pa s, on, each measured at 23 °C.
  • the compounds (A) used according to the invention are commercially available products or can be prepared by processes customary in chemistry.
  • the polymers of component (A) can be prepared by known methods, such as addition reactions, such as hydrosilylation, Michael addition, Diels-Alder addition or reactions between isocyanate-functional compounds with compounds having isocyanate-reactive groups.
  • the component (A) used according to the invention can contain only one type of compound of the formula (I) as well as mixtures of different types of compounds of the formula (I).
  • Component (A) can contain exclusively compounds of the formula (I) in which more than 90%, preferably more than 95% and particularly preferably more than 98% of all the silyl groups bonded to the radical Y are identical.
  • a component (A) which at least partly contains compounds of the formula (I) in which different silyl groups are bonded to a radical Y can also be used as component (A) in which at least 2 different types of silyl groups bonded to radicals Y are present, but all silyl groups bonded to a radical Y are identical.
  • compositions according to the invention preferably contain component (A) in concentrations of at most 60% by weight, particularly preferably at most 40% by weight, and preferably at least 10% by weight, particularly preferably at least 15% by weight.
  • the compositions according to the invention preferably contain at least 10 parts by weight, particularly preferably at least 25 parts by weight, particularly preferably at least 50 parts by weight, of component (B). Based on 100 parts by weight of component (A), the compositions according to the invention preferably contain at most 1000 parts by weight, particularly preferably at most 800 parts by weight, in particular at most 400 parts by weight, of component (B).
  • Component (B) preferably consists of at least 90% by weight of units of the formula (II).
  • Component (B) particularly preferably consists exclusively of units of the formula (II).
  • radicals R 3 are those given above for R
  • radical R 3 can also be a divalent aliphatic radical which connects two units of the formula (II) to one another, such as, for example, alkylene radicals having 1 to 10 carbon atoms, such as methylene, ethylene, propylene or butylene radicals.
  • alkylene radicals having 1 to 10 carbon atoms such as methylene, ethylene, propylene or butylene radicals.
  • a particularly common example of a divalent aliphatic radical is the ethylene radical.
  • the radical R 3 is preferably an optionally halogen-substituted, monovalent, SiC-bonded hydrocarbon radical having 1 to 18 carbon atoms, particularly preferably an aliphatic hydrocarbon radical having 1 to 8 carbon atoms, in particular the methyl radical.
  • radical R 4 are hydrogen atom and the examples given for radical R.
  • the radical R 4 is preferably a hydrogen atom or an alkyl radical having 1 to 10 carbon atoms which is unsubstituted or substituted by halogen atoms, particularly preferably an alkyl radical having 1 to 4 carbon atoms, in particular the methyl or ethyl radical.
  • Silicone resins in which at least 90% of all the R 3 radicals are methyl radicals are preferably used as component (B).
  • silicone resins in which all the R 3 radicals are methyl radicals are used as component (B).
  • silicone resins in which at least 90% of all the R 4 radicals are methyl, ethyl, propyl or isopropyl radicals are preferably used as component (B).
  • Silicone resins in which the alkoxy content is at least 5% by weight, particularly preferably at least 10.0% by weight and particularly preferably at least 15.0% by weight, based on the total weight of the resin, are preferably used as component (B). (B) .
  • silicone resins are used as component (B) which have a maximum of 40%, particularly preferably a maximum of 20%, particularly preferably 0%, units of the formula (II) in which c is 0, based in each case on the total number of an Units of formula (II).
  • Silicone resins are preferably used as component (B) which, based in each case on the total number of units of the formula (II), have at least 20%, particularly preferably at least 30%, particularly preferably at least 40%, of units of the formula (II) in which the index d stands for the value 0 or 1.
  • silicone resins used as component (B) are organopolysiloxane resins which consist essentially, preferably exclusively, of units selected from (Q) units of the formulas and (T)-units of the formulas and (D) units of the formulas and and (M) units of the formula where Me represents a methyl radical, and R 4 represents a hydrogen atom or an alkyl radical with 1 to 10 which is unsubstituted or substituted with halogen atoms Carbon atoms, particularly preferably unsubstituted alkyl radicals having 1 to 4 carbon atoms, where the resin (B) preferably contains (T) units and per mole of (T) units preferably 0-2 moles of (Q) units, 0-2 mole (D) units and 0-2 mole (M) units.
  • silicone resins (B) used according to the invention are organopolysiloxane resins which essentially, preferably exclusively, consist of units selected from (T) units of the formulas MeSiOg / g,
  • MeSi and MeSi where Me for methyl radical and R 4 are hydrogen atom or optionally halogen-substituted alkyl radicals having 1 to 10 carbon atoms.
  • silicone resins used as component (B) are organopolysiloxane resins which essentially, preferably exclusively, consist of (T) units of the formulas and (D)- units of the formulas and consist, where Me is a methyl radical and R 4 is a hydrogen atom or an alkyl radical having 1 to 10 carbon atoms which is unsubstituted or substituted by halogen atoms, preferably unsubstituted alkyl radicals having 1 to 4 carbon atoms.
  • silicone resins used as component (B) are organopolysiloxane resins which preferably contain 90%, in particular exclusively, of (T) units of the formulas exist, where Me is a methyl radical and R 4 is a hydrogen atom or optionally halogen-substituted alkyl radicals having 1 to 10 carbon atoms, preferably unsubstituted Alkoxy radicals having 1 to 4 carbon atoms, particularly preferably methyl radicals, based in each case on the total number of units.
  • T is a methyl radical
  • R 4 is a hydrogen atom or optionally halogen-substituted alkyl radicals having 1 to 10 carbon atoms, preferably unsubstituted Alkoxy radicals having 1 to 4 carbon atoms, particularly preferably methyl radicals, based in each case on the total number of units.
  • silicone resins that have such a high proportion of silicon-bonded methyl groups leads to adhesives with a particularly high level of hardness.
  • the silicone resins used as component (B) preferably have an average molar mass (number average) M n of at least 200 g/mol and particularly preferably at least 300 g/mol, the average molar mass M n preferably being at most 400,000 g/mol, particularly preferably at most 10,000 g/mol, in particular at most 3000 g/mol.
  • Component (B) preferably has a polydispersity (Mw/Mn) of from 1.0 to 4.5, particularly preferably from 1.0 to 4.0, in particular from 1.0 to 3.5.
  • the silicone resins used as component (B) can be either solid or liquid at 23° C. and 1000 hPa, silicone resins (B) preferably being liquid.
  • the silicone resins (B) preferably have a viscosity in the range from 10 to 100,000 mPa.s, preferably in the range from 20 to 1000 mPa.s, particularly preferably in the range from 50 to 500 mPa.s, in each case at 25.degree.
  • the silicone resins used as component (B) can be used either in pure form or in the form of a mixture with a suitable solvent (BL).
  • solvents (BL) All compounds which are not reactive towards components (A) and (B) at room temperature and have a boiling point ⁇ 250° C. at 1013 mbar can be used as solvents (BL).
  • solvents (BL) that may be used are ethers (eg diethyl ether, methyl t-butyl ether, ether derivatives of glycol, THF), esters (eg ethyl acetate, butyl acetate, glycol ester), aliphatic hydrocarbons (eg pentane, cyclopentane, hexane, cyclohexane, heptane). , Done or long-chain branched and unbranched alkanes), ketones (e.g.
  • aromatics e.g. toluene, xylene, ethylbenzene, chlorobenzene
  • alcohols e.g. methanol, ethanol, glycol, propanol, isopropanol, glycerol, butanol , isobutanol, t-butanol.
  • silicone resins are used as component (B) which contain less than 0.1% by weight, preferably less than 0.05% by weight, particularly preferably less than 0.02% by weight, in particular less than 0.01% by weight aromatic solvents (BL).
  • silicone resins are used as component (B) which, with the exception of alcohols R 4 OH, contain less than 0.1% by weight, preferably less than 0.05% by weight, particularly preferably less than 0.02% by weight, in particular less than 0.01% by weight, of solvent (BL), where R 4 has the meaning given above.
  • resins are used as component (B) which, with the exception of alcohols R 4 OH, contain no solvents (BL) at all, where R 4 has the meaning given above.
  • the silicone resins used as component (B) are commercially available products or can be prepared by methods customary in silicon chemistry.
  • compositions according to the invention can contain all other substances which have also been used to date in crosslinkable compositions and which differ from components (A) and (B), such as (C) containing nitrogen organosilicon compounds, (D) fillers, (E) non-reactive plasticizers, (F) catalysts, (G) adhesion promoters, (H) water scavengers, (I) additives, and (J) aggregates.
  • the optionally used component (C) is preferably an organosilicon compound containing units of the formula wherein
  • R 6 can be the same or different and is a monovalent, optionally substituted SiC-bonded organic radical free from basic nitrogen,
  • R 7 can be the same or different and is a hydrogen atom or optionally substituted hydrocarbon radicals
  • D can be the same or different and is a monovalent, SiC-bonded radical with basic nitrogen, f is 0, 1, 2 or 3, preferably 1, g is 0, 1, 2 or 3, preferably 1, 2 or 3, especially preferably 1 or 3, and h is 0, 1, 2, 3 or 4, preferably 1, with the proviso that the sum of f+g+h is less than or equal to 4 and at least one radical D is present per molecule .
  • radical R 6 are the examples given for R.
  • the radical R 6 is preferably an optionally halogen-substituted hydrocarbon radical having 1 to 18 carbon atoms, particularly preferably a hydrocarbon radical having 1 to 5 carbon atoms, in particular the methyl radical.
  • the radicals R 7 are preferably a hydrogen atom or a hydrocarbon radical having 1 to 18 carbon atoms which is unsubstituted or substituted by halogen atoms, particularly preferably a hydrogen atom or a hydrocarbon radical having 1 to 10 carbon atoms, in particular a methyl or ethyl radical.
  • the radical D is preferably the
  • silanes of the formula (III) optionally used according to the invention are examples of the silanes of the formula (III) optionally used according to the invention.
  • the organosilicon compounds (C) can also assume the function of a curing catalyst or cocatalyst.
  • organosilicon compounds (C) can act as adhesion promoters and/or as water scavengers.
  • organosilicon compounds are commercially available products or can be prepared by processes customary in chemistry.
  • compositions according to the invention contain component (C), the amounts are preferably from 0.1 to 25 parts by weight, particularly preferably from 0.2 to 20 parts by weight, in particular from 0.5 to 15 parts by weight, based in each case on 100 parts by weight of component ( A).
  • the compositions according to the invention preferably contain component (C).
  • the fillers (D) optionally used in the compositions according to the invention can be any previously known fillers.
  • Examples of fillers (D) are non-reinforcing fillers, ie fillers with a BET surface area of preferably up to 50 m 2 /g, such as quartz, diatomaceous earth, calcium silicate, zirconium silicate, talc, kaolin, zeolite, metal oxide powder such as aluminum, titanium -, Iron or zinc oxides or their mixed oxides, barium sulfate, calcium carbonate, gypsum, silicon nitride, silicon carbide, boron nitride, glass and plastic powders such as polyacrylonitrile powder; reinforcing fillers, ie fillers with a BET surface area of more than 50 m 2 / g, such as fumed silica, precipitated
  • Silicic acid precipitated chalk and silicon-aluminum mixed oxides with large BET surface
  • Aluminum trihydrate, carbon black, hollow spherical fillers such as ceramic microspheres, elastic plastic beads, glass beads or fibrous fillers.
  • the fillers mentioned can be made hydrophobic, for example by treatment with organosilanes or. - siloxanes or with stearic acid or by etherification of hydroxyl groups to alkoxy groups.
  • the optionally used fillers (D) are preferably calcium carbonate, magnesium carbonate and/or calcium-magnesium mixed carbonates, talc, aluminum trihydroxide or silicic acid.
  • Preferred types of calcium carbonate are ground or precipitated and optionally surface-treated with fatty acids such as stearic acid or salts thereof.
  • the preferred silica is preferably pyrogenic silica.
  • the fillers (D) are preferably additives which are suitable for transparent applications, such as silicate or metal oxide compounds.
  • the preferred fillers for transparent applications are fumed silica or titanium dioxide.
  • Any fillers (D) used have a moisture content of preferably less than 1% by weight, particularly preferably less than 0.5% by weight.
  • compositions according to the invention contain fillers as component (D), the amounts involved are preferably 10 to 1000 parts by weight, particularly preferably 40 to 500 parts by weight, in particular 80 to 300 parts by weight, based in each case on 100 parts by weight of component (A).
  • the compositions according to the invention preferably contain fillers (D).
  • any non-reactive plasticizers which have also hitherto been used in crosslinkable organopolysiloxane compositions can be used as optional component (E).
  • non-reactive plasticizers optionally used as component (E) are preferably organic compounds selected from the groups of substances consisting of
  • Polystyrenes • polybutadienes, polyisobutylenes, • polyesters and • polyethers.
  • non-reactive plasticizers optionally used as component (E) are preferably those which do not react with water or with components (A) and (B) at temperatures of ⁇ 80°C, are liquid at 20°C and 1013 hPa and have a boiling point of > 250°C at 1013 hPa.
  • carboxylic acid ester (E) examples include phthalic acid esters such as dioctyl phthalate, diisooctyl phthalate, diisononyl phthalate, diisodecyl phthalate and diundecyl phthalate; perhydrogenated phthalic acid esters such as diisononyl 1,2-cyclohexanedicarboxylate and dioctyl 1,2-cyclohexanedicarboxylate; adipic acid esters such as dioctyl adipate; benzoic acid esters; esters of trimellitic acid, glycol esters; Esters of saturated alkanediols, e.g.
  • polyethers (E) are polyethylene glycols, poly-THF and polypropylene glycols with molar masses M n of preferably 200 to 20,000 g/mol.
  • non-reactive plasticizers with molar masses or, in the case of polymeric plasticizers, average molar masses M n of at least 200 g/mol, particularly preferably greater than 500 g/mol, in particular greater than 900 g/mol. They preferably have molar masses or average molar masses M n of not more than 20,000 g/mol, particularly preferably not more than 10,000 g/mol, in particular not more than 8000 g/mol.
  • phthalic ester-free plasticizers such as perhydrogenated phthalic esters, esters of trimellitic acid, polyesters or polyethers
  • component (E) is particularly preferably polyethers, in particular polyethylene glycols, poly-THF and polypropylene glycols, in their entirety particularly preferably polypropylene glycols.
  • the preferred polyethers have molar masses M n preferably in a range from 400 to 20000 g/mol, particularly preferably in a range from 800 to 12000 g/mol, in particular in a range from 1000 to 8000 g/mol.
  • compositions according to the invention contain non-reactive plasticizers as component (E), the amounts involved are preferably 5 to 300 parts by weight, particularly preferably 10 to 200 parts by weight, in particular 20 to 150 parts by weight, based in each case on 100 parts by weight of component (A).
  • the compositions according to the invention preferably contain non-reactive plasticizers (E).
  • the catalysts (F) optionally used in the compositions according to the invention can be any previously known catalysts for compositions which cure by silane condensation.
  • metal-containing curing catalysts (F) are organic titanium and tin compounds, for example titanic acid esters such as tetrabutyl titanate, tetrapropyl titanate, tetraisopropyl titanate and titanium tetraacetylacetonate; Tin compounds such as dibutyltin dilaurate, dibutyltin maleate, dibutyltin diacetate, dibutyltin dioctanoate,
  • metal-free curing catalysts (F) are basic compounds such as triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, amidines such as 1,5-diazabicyclo[4.3.0]non-5- en or 1,8-diazabicyclo[5.4.0]undec-7-ene, guanidines such as tetramethylguanidine, N,N-bis(N,N-dimethyl-2-aminoethyl)- methylamine, N,N-dimethylcyclohexylamine, N,N-dimethylphenylamine and N-ethylmorpholinine.
  • basic compounds such as triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, amidines such as 1,5-diazabicyclo[4.3.0]non-5- en or 1,8-diazabicyclo[5.4.0]undec-7
  • Acidic compounds can also be used as component (F), such as phosphoric acid and its partially esterified derivatives, toluenesulfonic acid, sulfuric acid, nitric acid or else organic carboxylic acids, for example acetic acid and benzoic acid.
  • component (F) such as phosphoric acid and its partially esterified derivatives, toluenesulfonic acid, sulfuric acid, nitric acid or else organic carboxylic acids, for example acetic acid and benzoic acid.
  • compositions according to the invention contain catalysts (F), the amounts involved are preferably from 0.01 to 20 parts by weight, particularly preferably from 0.05 to 5 parts by weight, based in each case on 100 parts by weight of component (A).
  • any catalysts (F) used are metal-containing
  • Curing catalysts preferably tin-containing catalysts.
  • This embodiment of the invention is particularly preferred when component (A) consists entirely or at least partially, ie at least 90% by weight, preferably at least 95% by weight, of compounds of the formula (I) in which index b is not equal to 1.
  • metal-containing catalysts (F), and in particular tin-containing catalysts can preferably be dispensed with if component (A) is completely or at least partially, ie at least 10% by weight, preferably at least 20% by weight % by weight, consists of compounds of the formula (I) in which the index b is 1 and the radical R 1 has the meaning of a hydrogen atom.
  • component (A) is completely or at least partially, ie at least 10% by weight, preferably at least 20% by weight % by weight, consists of compounds of the formula (I) in which the index b is 1 and the radical R 1 has the meaning of a hydrogen atom.
  • This embodiment of the invention without metal and in particular without tin-containing catalysts is particularly preferred.
  • the adhesion promoters (G) optionally used in the compositions according to the invention can be any adhesion promoters previously described for systems curing by silane condensation.
  • adhesion promoters are epoxysilanes, such as glycidoxypropyltrimethoxysilane, glycidoxypropylmethyldimethoxysilane, glycidoxypropyltriethoxysilane or glycidoxypropylmethyldiethoxysilane, 2-(3-triethoxysilylpropyl)maleic anhydride, N-(3-trimethoxysilylpropyl)urea, N-(3- Triethoxysilylpropyl) urea, N-(trimethoxysilylmethyl) urea, N-(methyldimethoxysilylmethyl) urea, N-(3-triethoxysilylmethyl)urea, N-(3-methyldiethoxysilylmethyl)urea, O-methylcarbamatomethyl- methyldimethoxysilane, O-methylcarbamatomethyl-trimethoxysilane, O-ethylcarbamato
  • compositions of the invention contain adhesion promoters (G), the amounts involved are preferably from 0.5 to 30 parts by weight, more preferably from 1 to 10 parts by weight, based in each case on 100 parts by weight of crosslinkable composition.
  • the water scavengers (H) optionally used in the compositions according to the invention can be any water scavengers described for systems curing by silane condensation.
  • water scavengers (H) are silanes such as vinyltrimethoxysilane, vinyltriethoxysilane, vinylmethyldimethoxysilane, tetraethoxysilane, O-methylcarbamatomethylmethyldimethoxysilane, O-methylcarbamatomethyltrimethoxysilane, 0-ethylcarbamatomethylmethyldiethoxysilane, 0-
  • compositions of the invention contain water scavengers (H), the amounts involved are preferably from 0.5 to 30 parts by weight, more preferably from 1 to 10 parts by weight, based in each case on 100 parts by weight of crosslinkable composition.
  • the compositions according to the invention preferably contain water scavengers (H).
  • the additives (I) optionally used in the compositions according to the invention can be any additives typical of silane-crosslinking systems known hitherto.
  • the additives (I) are compounds other than the previously mentioned components, preferably antioxidants, UV stabilizers such as so-called HALS compounds, fungicides, commercially available defoamers, for example from BYK (Wesel, Germany) , commercially available wetting agents, eg from BYK (Wesel, Germany) or pigments.
  • compositions according to the invention contain additives (I), the amounts involved are preferably from 0.01 to 30 parts by weight, particularly preferably from 0.1 to 10 parts by weight, based in each case on 100 parts by weight of component (A).
  • the compositions according to the invention preferably contain additives (I).
  • Any additives (J) used are preferably tetraalkoxysilanes, for example tetraethoxysilane, and/or their partial condensates, reactive plasticizers, rheological additives, flame retardants or organic solvents.
  • Preferred reactive plasticizers (J) are compounds which contain alkyl chains with 6 to 40 carbon atoms and have a group which is reactive towards the compounds (A).
  • Examples are isooctyltrimethoxysilane, isooctyltriethoxysilane, N-octyltrimethoxysilane, N-octyltriethoxysilane,
  • decyltrimethoxysilane decyltriethoxysilane
  • the rheological additives (J) are preferably polyamide waxes which are solid at room temperature, hydrogenated castor oils or stearates.
  • Flame retardants (J) which can be used are all typical flame retardants as are typical for adhesive and sealant systems, in particular halogenated compounds and derivatives, in particular (partial) esters, of phosphoric acid.
  • organic solvents (J) are the compounds already mentioned above as solvents (BL), preferably alcohols.
  • compositions according to the invention contain one or more components (J), these are in each case amounts of preferably 0.5 to 200 parts by weight, particularly preferably 1 to 100 parts by weight, in particular 2 to 70 parts by weight, based in each case on 100 parts by weight of component ( A).
  • compositions according to the invention are preferably those containing (A) 100 parts by weight of compounds of the formula (I),
  • C 0.1 to 25 parts by weight of organosilicon compounds containing basic nitrogen, optionally fillers (D), optionally non-reactive plasticizers (E), optionally catalysts (F), optionally adhesion promoters (G), optionally water scavengers (H), optionally additives (I ) and optionally additives (J).
  • compositions according to the invention are particularly preferably those containing
  • the masses according to the invention are particularly preferably those containing them
  • the components used according to the invention can each be one type of such a component or a mixture of at least two types of a respective component.
  • compositions according to the invention preferably contain no components other than components (A) to (J).
  • the materials according to the invention are particularly preferably transparent materials.
  • the masses according to the invention are preferably liquid to pasty masses with viscosities in the range from 500 to 3000,000 mPa.s, particularly preferably in the range from 1000 to 1500,000 mPa.s, in each case at 23.degree.
  • compositions according to the invention can be produced in any manner known per se, for example by methods and mixing processes which are customary for the production of moisture-curing compositions.
  • the order in which the various components are mixed with one another can be varied as desired.
  • Another object of the present invention is a process for producing the compositions of the invention by mixing the individual components in any order.
  • This mixing can take place at room temperature and the pressure of the surrounding atmosphere, ie in a range from about 900 to 1100 hPa. If desired, however, this mixing can also take place at higher temperatures, e.g. at temperatures in the range from 30 to 130 °C. Furthermore, it is possible to mix intermittently or continuously under reduced pressure, such as 30 to 500 hPa absolute pressure, to remove volatile compounds and/or air.
  • the mixing according to the invention preferably takes place with the exclusion of moisture.
  • compositions according to the invention are preferably one-component compositions which can be stored in the absence of water and can be crosslinked at room temperature when exposed to water.
  • compositions according to the invention can also be part of two-component crosslinking systems in which OH-containing compounds, such as water, are added in a second component.
  • compositions according to the invention are preferably crosslinked at room temperature.
  • it can also be carried out at temperatures higher or lower than room temperature, e.g. at -5°C to 15°C or at 30°C to 50°C and/or by means of water concentrations exceeding the normal water content of the air.
  • the crosslinking is preferably carried out at a pressure in the range from 100 to 1100 hPa, in particular at the pressure of the surrounding atmosphere, ie in a range from 900 to 1100 hPa.
  • Another object of the present invention are moldings produced by crosslinking the compositions of the invention.
  • the moldings according to the invention preferably have a tear strength of at least 4.0 MPa, particularly preferably at least 5.0 MPa, in particular at least 8.0 MPa, measured in each case according to DIN EN 53504-S1.
  • the moldings according to the invention can be any moldings, such as seals, pressed articles, extruded profiles, coatings, impregnations, potting, lenses, prisms, polygonal structures, laminate or adhesive layers.
  • Another object of the invention is a method for producing material composites, in which the composition according to the invention is applied to at least one substrate and then crosslinked.
  • Examples include coatings, potting, the manufacture of molded articles, composite materials, and composite molded parts.
  • Composite molded parts are to be understood here as meaning a uniform molded article made from a composite material which is composed of a crosslinked product of the compositions according to the invention and at least one substrate such that there is a firm, permanent connection between the two parts.
  • the composition according to the invention can also be vulcanized between at least two identical or different substrates, such as in the case of adhesive bonds, laminates or encapsulations.
  • substrates that can be bonded or sealed according to the invention are plastics including PVC, metals, concrete, wood, mineral substrates, glass, ceramics and painted surfaces.
  • compositions according to the invention can be used for all purposes for which storage is carried out in the absence of water. capable masses which crosslink to form elastomers when exposed to water at room temperature can be used.
  • compositions according to the invention have the advantage that they are easy to produce.
  • crosslinkable compositions of the invention have the advantage that they are notable for very high storage stability and a high crosslinking rate.
  • crosslinkable compositions according to the invention have the advantage that they have an excellent adhesion profile.
  • crosslinkable masses according to the invention have the advantage that they are easy to process.
  • GENIOSIL ® STP-E 10 cx-silane-terminated polyether with a dynamic viscosity at 25 °C of approx. 10000 mPa ⁇ s, available from Wacker Chemie AG, D-Munich.
  • GENIOSIL® STP-E 15 ⁇ -silane-terminated polyether with a dynamic viscosity at 25° C. of about 10,000 mPa ⁇ s, available from Wacker Chemie AG, D-Munich.
  • GENIOSIL ® STP-E 30 ⁇ -silane-terminated polyether with a dynamic viscosity at 25 °C of approx.
  • GENIOSIL® STP-E 35 ⁇ -silane-terminated polyether with a dynamic viscosity at 25° C. of about 30,000 mPa ⁇ s, available from Wacker Chemie AG, D-Munich.
  • SILRES ® MSE 100 Methoxy-functional methylpolysiloxane resin, available from Wacker Chemie AG, D-Munich, with a kinematic viscosity of 20-35 mm 2 /s and a polydispersity of approx. 9.5, measured according to the point 1.4 named Process (Resin VB1).
  • the mass-average molar mass M w is determined by means of size exclusion chromatography (SEC) against polydimethylsiloxane standards, in toluene, at 35° C., flow rate 0.7 ml/min and detection with RI (refractive index detector ) determined on a column set Meso Pore - Oligo Pore (Agilent, Germany) with an injection volume of 10 ⁇ .
  • SEC size exclusion chromatography
  • viscosities of high-viscosity materials were measured after heating to 23° C. using a DV 3 P rotational viscometer from A. Paar (Brookfield systems), determined using spindle 5 at 2.5 rpm according to ISO 2555.
  • the alkoxy group content was determined by means of 1 H nuclear magnetic resonance spectroscopy ( 1 H NMR; Bruker Avance III HD 500 ( 1 H: 500.2 MHz) spectrometer with BBO 500 MHz S2 probe head; 50 mg of the respective sample in 500 ⁇ l CD 2 CI 2 ).
  • Table 1 lists the information on the MeO/T ratio of resins Bl-B7 and VBl-VB5.
  • the resin VB1 was fractionated by distillation in a laboratory thin layer. This was done in three consecutive experiments, in which the materials were fractionated at fixed temperatures and pressures in two runs each. In each of the 3 experiments, 2 thin-layer steps were carried out in such a way that the residue from the first thin-layer run was put back into the thin-layer and distilled. The two distillate fractions thus obtained (at the same temperature and pressure) were then combined. All of the analytical data are summarized in Table 1.
  • 150 g of GENIOSIL ® STP-E10 are mixed in a laboratory planetary mixer from PC-LaborSystem, equipped with two bar mixers, at approx. 25°C with 150 g of the respective resins B4 and B5 and 6 g of stabilizer (commercially available under the name TINUVIN ® 123 at BASF AG, Germany; GAS NO: 129757-67-1) for 2 minutes at 200 rpm. Thereafter, 284.5 g of aluminum trihydroxide with a BET surface area of 3-5 m 2 /g and a d50 value of 1.7-2.1 ⁇ m (commercially available under the name “Martinal OL 104” from Albemarie Corp.) with stirring for one minute at 600 rpm.
  • N-(2-aminoethyl)-3-aminopropyl-methyl-dimethoxysilane are mixed in for 1 minute at 200 rpm. Finally, for 2 Minutes at 600 rpm and for 1 minute at 200 rpm at a pressure of 100 mbar and stirred without bubbles.
  • the formulation is filled into 310 ml PE cartridges and stored at 25° C. for one day before the examination.
  • compositions were each spread out to a depth of 2 mm on milled Teflon plates and cured for 2 weeks at 23° C. and 50% relative atmospheric humidity.
  • sample quantities for smaller sample quantities (resin B3), the above mixing procedure was scaled down as follows, while observing the mass ratios used above. 20 g of GENIOSIL ® STP-E10 were mixed in a DAG speed mixer
  • the formulation is filled into a 55 ml PE cartridge and stored at 25° C. for one day before the examination.
  • the mass was spread out onto a milled Teflon plate to a depth of 2 mm and cured at 23° C. and 50% relative atmospheric humidity for 2 weeks.
  • the Shore A hardness, the tensile strength and the elongation at break were determined for each of the specimens shown (presented using the laboratory planetary mixer or speed mixer).
  • the Shore A hardness was determined according to DIN 53505, the tensile strength according to DIN 53504-S1 and the elongation at break according to DIN 53504-S1.
  • the assignments of the test specimens are in Table 5, the application data of the moldings are summarized in Table 6.

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  • Organic Chemistry (AREA)
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Abstract

L'invention concerne des substances réticulables contenant : (A) 100 parties en poids de composés de formule Y - [(CR12)b- SiRaOR2)3-a]x (I) ; (B) 5 à 2000 parties en poids de résines de silicone contenant des motifs de formule R3 C(R4O)dSiO(4-c-d)/2 (II), dans lesquelles les groupes fonctionnels et les indices présentent les significations indiquées dans la revendication 1, à condition que la somme de c+d soit inférieure ou égale à 3, que dans au moins 40 % des motifs de formule (II) c soit égal à 0 ou 1 et que la résine de silicone présente une polydispersité Mw/Mn inférieure à 5,0 ; éventuellement (C) des composés organosiliciés comprenant de l'azote basique ; éventuellement (D) des charges ; éventuellement (E) des plastifiants non réactifs ; éventuellement (F) des catalyseurs ; éventuellement (G) des promoteurs d'adhérence ; éventuellement (H) des pièges d'eau ; éventuellement (I) des additifs ; et éventuellement [J] des substances supplémentaires. L'invention concerne également un procédé pour leur production et leur utilisation en tant que substances adhésives, d'étanchéité et de revêtement, en particulier pour le collage de substrats.
PCT/EP2020/074327 2020-09-01 2020-09-01 Substances réticulables sur la base de polymères terminés par organyloxysilane WO2022048728A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1093482B1 (fr) 1998-03-25 2004-08-18 Henkel Kommanditgesellschaft auf Aktien Polyurethane et preparation contenant du polyurethane
EP1641854B1 (fr) 2003-07-04 2007-01-31 Consortium für elektrochemische Industrie GmbH Prepolymeres a groupes terminaux alcoxysilane
EP1535940B1 (fr) 2003-11-27 2007-06-13 Wacker Chemie AG Procédé pour la préparation de polymères ayant comme groups terminaux organyloxysilyle.
EP1896523B1 (fr) 2005-06-23 2010-10-27 Wacker Chemie AG Transformation continue de polymeres analogues de monomeres de silane reactifs avec des polymeres fonctionnalises
DE102011081264A1 (de) 2011-08-19 2013-02-21 Wacker Chemie Ag Vernetzbare Massen auf Basis von organyloxysilanterminierten Polymeren
DE102014207508A1 (de) * 2014-04-17 2015-10-22 Wacker Chemie Ag Vernetzbare Massen auf Basis von organyloxysilanterminierten Polymeren

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1093482B1 (fr) 1998-03-25 2004-08-18 Henkel Kommanditgesellschaft auf Aktien Polyurethane et preparation contenant du polyurethane
EP1641854B1 (fr) 2003-07-04 2007-01-31 Consortium für elektrochemische Industrie GmbH Prepolymeres a groupes terminaux alcoxysilane
EP1535940B1 (fr) 2003-11-27 2007-06-13 Wacker Chemie AG Procédé pour la préparation de polymères ayant comme groups terminaux organyloxysilyle.
EP1896523B1 (fr) 2005-06-23 2010-10-27 Wacker Chemie AG Transformation continue de polymeres analogues de monomeres de silane reactifs avec des polymeres fonctionnalises
DE102011081264A1 (de) 2011-08-19 2013-02-21 Wacker Chemie Ag Vernetzbare Massen auf Basis von organyloxysilanterminierten Polymeren
DE102014207508A1 (de) * 2014-04-17 2015-10-22 Wacker Chemie Ag Vernetzbare Massen auf Basis von organyloxysilanterminierten Polymeren

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