WO2010072531A1 - Réticulation thermique d'un composé organopolysiloxane présent sur un substrat au moyen d'un réactif aldéhyde - Google Patents

Réticulation thermique d'un composé organopolysiloxane présent sur un substrat au moyen d'un réactif aldéhyde Download PDF

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Publication number
WO2010072531A1
WO2010072531A1 PCT/EP2009/066318 EP2009066318W WO2010072531A1 WO 2010072531 A1 WO2010072531 A1 WO 2010072531A1 EP 2009066318 W EP2009066318 W EP 2009066318W WO 2010072531 A1 WO2010072531 A1 WO 2010072531A1
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groups
substrate
hydrocarbon radical
interrupted
substituted
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PCT/EP2009/066318
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German (de)
English (en)
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Timo Hagemeister
Daniel Schildbach
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Wacker Chemie Ag
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Publication of WO2010072531A1 publication Critical patent/WO2010072531A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • 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
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/07—Aldehydes; Ketones
    • 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
    • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/10—Coatings without pigments
    • D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
    • D21H19/24—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H19/32—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming a linkage containing silicon in the main chain of the macromolecule
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/59—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon

Definitions

  • the present invention relates to a process for thermal crosslinking of substances present on a substrate
  • Organopolysiloxane compound having amino groups with aldehyde reagent.
  • Silicone or silicone-containing formulations and composites are known and are used in the form of films, coatings and coatings in large quantities for the modification and equipment of various materials and fibers. In their range of properties, silicones or silicone-containing formulations are superior to purely organic films, coatings and coatings in many respects. So leads the
  • silicone products to a vast extent not otherwise available but usually desirable properties such as flow, gas permeability, abrasion resistance, hydrophobicity, smoothness, feel or gloss of the treated substrate.
  • the coating can be removed either simply mechanically, for example by rubbing or rubbing, or by chemical stress, for example contact with various solvents and / or exposure to certain pH environments (as occur, for example, in washing processes), can solve again from the substrate.
  • One approach to solving the problem of lack of permanence is to crosslink the individual silicone polymer chains both with each other and with the substrate to be treated, thus increasing the mechanical and chemical resistance and thus the permanence of the overall system.
  • Crosslinking and binding to the substrate can be effected both by non-covalent interactions and by covalent bonds.
  • thermoplastic silicone elastomers with each other for increased network density and by interaction with also hydrogen bond forming groups of the substrate (e.g., hydroxy moieties on cellulose surfaces) also for some fixation.
  • the preparation and use of such thermoplastic silicone elastomers are described in detail, inter alia, in EP 0 606 532 A1 and EP 0 342 826 A2.
  • Another noncovalent crosslinking mechanism is based on acid-base interactions between Lewis basic / Lewis acidic groups of the silicone polymer with Lewis acidic / Lewis basic groups of the substrate or polymer.
  • these are amino-functional silicone oils which, as is known, have a positive influence in particular on hydrophobicity and softness of textiles and, because of their Lewis-basic amino functionalities, have the property of being 'absorbed' onto the Lewis acidic fibers.
  • Such silicone amine oils and their applications are described for example in EP 1555011 A. Both mechanisms have in common that their produced permanence is only temporary and inadequate and the coating can be easily removed both mechanically and chemically,
  • a covalent crosslinking can be carried out, for example, by the fact that the silicone polymers already in the preparation by
  • Such subsequent fixation / crosslinking may be effected, for example, by the presence of alkoxysilyl groups in the silicone polymer which provide better permanence by hydrolysis and condensation with hydroxy groups of the substrate or hydroxy groups of other silicone polymers.
  • alkoxysilyl-containing silicone polymers are described for example in EP 1544223 Al.
  • a formation of comparatively stable siloxane bonds Si On the other hand, O-Si as a rule again requires prior treatment of the substrate with corresponding silanes.
  • the historically preferred form is mechanistically based on condensation crosslinking. This type of crosslinking takes place by reaction of SiOH groups of corresponding silicone polymers, which are crosslinked with SiH-containing crosslinkers to form hydrogen, generally tin-catalyzed.
  • the systems can be solvent-based, solvent-free or water-based. Due to the improved environmental and safety-relevant processing, solvent-free systems are to be preferred. Water-based systems are without alternative in the direct siliconization during papermaking, since the aqueous production process requires an analogous water-based silicone system. Industrial emulsions are used.
  • ⁇ / -methylol groups can in principle be prepared by reacting amines units with formaldehyde, as a rule, however, the reaction leads to polymeric condensation products, so that polymeric networks ultimately result via imine intermediates.
  • This reaction of amines with formaldehyde has already been described: US Pat. No. 3,461,100 describes condensation products of aldehydes and primary diamines and monoamines. The resulting high polymer condensation products are discussed as protective coatings.
  • DE 10047643 A1 describes polymeric condensation products of aldehydes and silicon amines, which are, however, exclusively high polymer and highly crosslinked. In both documents, the product is already high polymer after implementation. It is thus no longer a reactive form, as it is the monoaddition product of a formaldehyde molecule to an amine, and is therefore no longer available for subsequent reactions on substrates or post-crosslinking reactions with each other.
  • stabilized silicone emulsions or stabilized silicone solutions containing ⁇ / -methylolated structural units are basically capable of post-crosslinking in the sense described above.
  • US Pat. No. 3,433,536 A describes the ⁇ / methylolation of terminal and lateral amidoalkyl-polysiloxanes by treating them with aqueous formaldehyde solution in the presence of methanol, thereby producing both the corresponding ⁇ / -methylolamidoalkyl-polysiloxanes and the corresponding ⁇ / -methylol-methyl ethers to be obtained.
  • such amide based ⁇ / -methylols and especially their ethers often have significantly reduced reactivities in the subsequent crosslinking and / or substrate fixation in comparison with N-methylols derived from corresponding amines, carbamates or ureas.
  • the invention provides a process for crosslinking organopolysiloxane compound (S) which contains at least one group of the general formula (1)
  • a liquid (F) is prepared in a first step with organopolysiloxane compound (S) and aldehyde reagent (A), in a second step the liquid (F) is applied to a substrate and in a third step the substrate is heated,
  • R is a divalent hydrocarbon radical having 1 to 20 carbon atoms, wherein the carbon chain may be interrupted by non-adjacent - (CO) -, -0-, -S- or -NR groups and may be substituted by -CN or -halogen;
  • R is a hydrogen atom, a hydrocarbon radical having 1 to 20
  • R is a hydrogen atom, a hydrocarbon radical having 1 to 20
  • Q adjacent (CO), -0-, -S- or -NR groups may be interrupted and substituted with -CN or -halogen;
  • R is a hydrocarbon radical having 1 to 20 carbon atoms, wherein the carbon chain may be interrupted by non-adjacent - (CO) -, -0-, -S or NR groups and may be substituted by -CN or -halogen;
  • R is a hydrogen atom, a hydrocarbon radical having 1 to 20 carbon atoms, wherein the carbon chain may be interrupted by non-adjacent - (CO) -, -0-, -S- or -NR groups and may be substituted by -CN or -halogen as well as with
  • R is a hydrogen atom, a hydrocarbon radical having 1 to 20
  • C atoms wherein the carbon chain may be interrupted by non-adjacent - (CO) -, -0-, -S- or -NR groups and substituted with -CN or -halogen, and may be covalently linked to R;
  • R is a hydrocarbon radical having 1 to 20 carbon atoms, wherein the carbon chain by non-adjacent - (CO) -, -0-, -
  • S- or -NR groups may be interrupted and substituted with -CN or -halogen;
  • R is a hydrocarbon radical having 1 to 20 C atoms
  • the process allows easy and rapid crosslinking on the substrate without the use of a noble metal catalyst.
  • the process is suitable both for impregnation and for coating with organopolysiloxane compound (S).
  • the organopolysiloxane compound (S) may already partially react with the aldehyde reagent (A) in the liquid (F), but the crosslinking reaction occurs on the coated or impregnated substrate.
  • aldehyde reagents (A) can be used, e.g. monomeric forms of formaldehyde, such as formaldehyde gas and aqueous or organic solutions of aldehydes, as well as formaldehyde in condensed form such as paraformaldehyde, trioxane, or other aldehyde condensates.
  • formaldehyde can also be present in latent form and first released in situ during the thermal crosslinking in the third step. All aldehyde-releasing agents are suitable for this purpose.
  • aldehyde derivative such as glyoxal can be used.
  • R is preferably a hydrogen atom or
  • R is a divalent alkyl group
  • R is preferably a hydrogen atom or an alkyl, cycloalkyl, alkenyl, aryl or arylalkyl radical
  • NR R group more preferably around the hydrogen atom.
  • R is preferably an alkyl, cycloalkyl, alkenyl, aryl or arylalkyl radical, in particular alkyl radical having 1 to 6 C atoms, particularly preferably the methyl radical.
  • R and / or R are preferably hydrogen atoms or alkyl, cycloalkyl, alkenyl, aryl or arylalkyl radicals, in particular alkyl radicals each having 1 to 6 C atoms, more preferably the hydrogen atom.
  • R is preferably alkyl, cycloalkyl,
  • Alkenyl, aryl or arylalkyl radicals in particular alkyl radical having 1 to 6 C atoms, particularly preferably the methyl radical.
  • R is preferably an alkyl, cycloalkyl, alkenyl, aryl or arylalkyl radical, in particular an alkyl radical having 1 to 6 C atoms, particularly preferably a methyl radical.
  • the organopolysiloxane compound (S) used preferably contains units of the general formula (3)
  • R is a hydrocarbon radical having 1 to 20 carbon atoms, wherein the carbon chain may be interrupted by non-adjacent - (CO) -, -0-, -S or -NR groups and may optionally be substituted by -CN or -halogen; R has the above meanings, a is 0, 1, 2 or 3, b is 0, 1, 2 or 3 and
  • A represents a group of the general formula (1), with the proviso that the sum a + b is less than or equal to 3 and the organopolysiloxane compound (S) has at least one unit of the general formula (3) with b different zero.
  • R is preferably alkyl, cycloalkyl,
  • Alkenyl, aryl or arylalkyl radicals preferably alkyl or aryl radicals each having 1 to 6 C atoms, more preferably the methyl, ethyl, vinyl or phenyl radical.
  • a is preferably 2 or 1 and b is preferably 0 or 1.
  • Halogen radicals in the context of the present invention are preferably fluorine, chlorine, bromine.
  • the organopolysiloxane compound (S) comprises both polymeric, oligomeric and dimeric organopolysiloxane compounds.
  • the viscosity of the organopolysiloxane compounds (S) is preferably at least 50, more preferably at least 100 mPa. s and preferably at most 5000, more preferably at most 1500 mPa.s, each at 25 ° C.
  • the organopolysiloxane compounds (S) used are preferably essentially linear polysiloxanes having terminal and / or pendant monovalent radicals A and / or chain-containing bivalent radicals A, where A has the abovementioned meaning.
  • the substantially linear polysiloxanes preferably at most 5%, in particular at most 1%, of the siloxane units are branching units.
  • a and R have the meanings given above; e is 0 or 1; m is 0 or an integer of 1 to 200; n is 0 or an integer of 1 to 200, and m + n is 0 or an integer of 1 to 400; with the proviso that at least one radical A is present per molecule.
  • m + n is preferably at least 5, more preferably at least i, and preferably at most 500, most preferably at most 250.
  • the ratio of the groups A: R is preferably at least 1: 10,000, in particular at least 1: 1000 and preferably at most 1: 5, in particular at most 1: 30.
  • Organopolysiloxane compound (S) it may also be advantageous that liquid (F) contains a catalyst for the crosslinking reaction.
  • a catalyst for the crosslinking reaction In principle, all Lewis and Bronsted acids are suitable as catalyst. These can be added directly to the silicone or applied as a separate component.
  • solubilizer which is inert to organopolysiloxane compound (S) and aldehyde reagent (A) is preferably added in their preparation.
  • solubilizers are ethers, such as tetrahydrofuran and dioxane, hydrocarbons, such as toluene and xylene, chlorinated hydrocarbons, ketones, such as acetone and methyl ethyl ketone and esters, and mixtures thereof.
  • Solubilizers having a boiling point or boiling range of up to 120 ° C. at 0.1 MPa are preferred.
  • the liquid (F) is preferably a solution or a
  • organopolysiloxane compound (S) and aldehyde reagent (A) each containing the organopolysiloxane compound (S) and aldehyde reagent (A).
  • liquid (F) is an emulsion or suspension
  • its preparation with aldehyde reagent (A) is carried out by methods familiar to the person skilled in the art.
  • organopolysiloxane compound (S) and aldehyde reagent (A) are preferably emulsified or suspended in a solvent inert to organopolysiloxane compound (S) and aldehyde reagent (A).
  • organopolysiloxane compound (S) is first emulsified or suspended and then the aldehyde reagent (A) is metered in.
  • the solvent the abovementioned solubilizers and water are preferred.
  • Formula (1) are used for liquids (F) which are an emulsion or suspension or solution, preferably at least 0.3, in particular at least 0.7, aldehyde groups of the general formula (2). Based on all NH units in the groups of general
  • Formula (1) are used for liquids (F) which are an emulsion or suspension or solution, preferably at most 5, in particular at most 1.3 aldehyde groups of the general formula (2).
  • liquids (F) especially those which are a solution, stabilizers are added, which prevent the premature crosslinking.
  • aliphatic alcohols having 1 to 10 carbon atoms, preferably having a boiling point or boiling range of up to 150 ° C at 0.1 MPa, such as methanol, ethanol, isopropanol and n-butanol.
  • the substrates impregnated or coated with the crosslinked organopolysiloxane compound (S), preferably papers and films, can be used for example for all classical release applications.
  • label applications, baking paper, medical sector, adhesive tapes, hygiene and graphic area are to be mentioned.
  • the substrates impregnated or coated with the crosslinked organopolysiloxane compound (S) may, for example, also be textiles and leather.
  • the liquid (F) can already be applied to the still wet paper directly after the paper making process.
  • the substrates impregnated or coated with the organopolysiloxane compound (S) may also be finely divided, e.g. Powder or granules, and be connected by the organopolysiloxane compound (S) as a binder to a shaped body.
  • the substrate is preferably heated to at least 80 ° C, in particular at least 100 ° C and preferably at most 180 ° C.
  • the heating preferably lasts at least 10 seconds, in particular at least 30 seconds and preferably at most 10 minutes.
  • the invention also provides the substrate containing the organopolysiloxane compound (S) crosslinked by the process with aldehyde reagent (A).
  • Emulsions from example 1 are applied with a 20 ⁇ m doctor blade to a glassine paper substrate (see Table 2). Subsequently, the coated papers are cured at 150 ° C for 120 s (1.1) or 240 s (1.2) in an oven and freed from water. The resulting siliconized papers are tested according to standard FINAT methods (see Table 2). Table 2: Application test of silicone emulsions on glassine paper Silca Classic (Ahlstrom company)
  • Example 2 The solutions of Example 2 are coated with a 20 ⁇ m doctor blade on a glassine paper substrate (see Table 3). Subsequently, the coated paper is cured for 2 min at 150 ° C in an oven and freed from the volatile components. The resulting siliconized papers are tested according to standard FINAT methods (see Table 3).
  • Example 4.2 Film coating
  • the silicone solution from Example 2.1 is applied using a 20 ⁇ m doctor blade to various corona-pretreated film substrate types (see Table 4). Subsequently, the coated films are cured for 30 s at 95 ° C in an oven and freed of the volatile components. The resulting siliconized films are tested according to standard FINAT methods (see Table 4).

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Silicon Polymers (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne un procédé de réticulation d'un composé organopolysiloxane (S) présentant au moins un groupe représenté par la formule (1) -R1-NHR2, au moyen d'un réactif aldéhyde (A) représenté par la formule (2) O=CH-R3. Dans une première étape, un liquide (F) est fabriqué au moyen de l'organopolysiloxane (S) et du réactif aldéhyde (A); dans une deuxième étape, le liquide (F) est appliqué sur un substrat; et dans une troisième étape, le substrat est chauffé, R1, R2 et R3 ayant les significations données dans la revendication 1. L'invention concerne également le substrat contenant le composé organopolysiloxane (S) réticulé au moyen du réactif aldéhyde (A) à l'aide du procédé selon l'invention.
PCT/EP2009/066318 2008-12-15 2009-12-03 Réticulation thermique d'un composé organopolysiloxane présent sur un substrat au moyen d'un réactif aldéhyde WO2010072531A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008054671A DE102008054671A1 (de) 2008-12-15 2008-12-15 Thermische Vernetzung von auf einem Substrat vorliegender Organopolysiloxanverbindung mit Aldehydreagens
DE102008054671.2 2008-12-15

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WO2010072531A1 true WO2010072531A1 (fr) 2010-07-01

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015003957A1 (fr) * 2013-07-08 2015-01-15 Wacker Chemie Ag Membranes à porosité symétrique en élastomère de silicone thermoplastique réticulé au moyen d'un aldéhyde
WO2021012048A1 (fr) * 2019-07-22 2021-01-28 Mcmaster University Élastomères de silicone à durcissement rapide, exempts de catalyseur

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GB1076259A (en) * 1963-07-12 1967-07-19 Pfersee Chem Fab Siloxane condensation polymers
US3432536A (en) * 1965-05-27 1969-03-11 Gen Electric Organopolysiloxane fluids substituted with methylolated amidoalkyl groups
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JPH0268303A (ja) * 1988-08-31 1990-03-07 Toray Ind Inc 超速乾水泳用具
DE10047643A1 (de) * 2000-09-26 2002-04-11 Basf Ag Polymere Aldehyd/Siloxan-Amin-Netzwerke
DE102006022842A1 (de) * 2006-05-16 2007-11-22 Wacker Chemie Ag Über Methylolgruppen vernetzbare Siliconpolymere
DE102007016990A1 (de) * 2007-04-11 2008-10-16 Wacker Chemie Ag Methylolgruppen enthaltende Siloxane

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DE3328456A1 (de) 1983-08-06 1985-02-21 Hoechst Ag, 6230 Frankfurt Formaldehydfreie waessrige kunststoffdispersionen auf basis eines vernetzbaren polymerisats, verfahren zu ihrer herstellung und ihre verwendung
JPS6327560A (ja) 1986-07-21 1988-02-05 Shin Etsu Chem Co Ltd 離型用シリコ−ン組成物
GB8811868D0 (en) 1988-05-19 1988-06-22 Ici Plc Release film
US5356706A (en) 1992-12-14 1994-10-18 Shores A Andrew Release coating for adhesive tapes and labels
US7238745B2 (en) 2003-12-15 2007-07-03 Bayer Materialscience Llc Aqueous polyurethane/urea dispersions containing alkoxysilane groups
EP1555011A1 (fr) 2004-01-07 2005-07-20 L'oreal Compositions cosmétiques detergentes comprenant une silicone aminée et un polymère de haut poids moleculaire et utilisation de ces dernieres

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Publication number Priority date Publication date Assignee Title
GB1076259A (en) * 1963-07-12 1967-07-19 Pfersee Chem Fab Siloxane condensation polymers
US3432536A (en) * 1965-05-27 1969-03-11 Gen Electric Organopolysiloxane fluids substituted with methylolated amidoalkyl groups
JPS60209206A (ja) * 1984-04-04 1985-10-21 Toray Ind Inc 気体分離用複合膜およびその製造方法
JPH0268303A (ja) * 1988-08-31 1990-03-07 Toray Ind Inc 超速乾水泳用具
DE10047643A1 (de) * 2000-09-26 2002-04-11 Basf Ag Polymere Aldehyd/Siloxan-Amin-Netzwerke
DE102006022842A1 (de) * 2006-05-16 2007-11-22 Wacker Chemie Ag Über Methylolgruppen vernetzbare Siliconpolymere
DE102007016990A1 (de) * 2007-04-11 2008-10-16 Wacker Chemie Ag Methylolgruppen enthaltende Siloxane

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015003957A1 (fr) * 2013-07-08 2015-01-15 Wacker Chemie Ag Membranes à porosité symétrique en élastomère de silicone thermoplastique réticulé au moyen d'un aldéhyde
WO2021012048A1 (fr) * 2019-07-22 2021-01-28 Mcmaster University Élastomères de silicone à durcissement rapide, exempts de catalyseur

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