WO2010072541A1 - Réticulation d'un composé organopolysiloxane présent sur un substrat au moyen d'un réactif aldéhyde gazeux - Google Patents

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

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Publication number
WO2010072541A1
WO2010072541A1 PCT/EP2009/066373 EP2009066373W WO2010072541A1 WO 2010072541 A1 WO2010072541 A1 WO 2010072541A1 EP 2009066373 W EP2009066373 W EP 2009066373W WO 2010072541 A1 WO2010072541 A1 WO 2010072541A1
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WO
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Prior art keywords
groups
hydrocarbon radical
organopolysiloxane compound
interrupted
substituted
Prior art date
Application number
PCT/EP2009/066373
Other languages
German (de)
English (en)
Inventor
Timo Hagemeister
Wolfgang Schattenmann
Original Assignee
Wacker Chemie Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wacker Chemie Ag filed Critical Wacker Chemie Ag
Publication of WO2010072541A1 publication Critical patent/WO2010072541A1/fr

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Classifications

    • 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
    • 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
    • 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
    • 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
    • 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
    • D21H17/63—Inorganic compounds
    • D21H17/67—Water-insoluble compounds, e.g. fillers, pigments
    • D21H17/675—Oxides, hydroxides or carbonates
    • 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

Definitions

  • the present invention relates to a process for crosslinking organopolysiloxane compound having amino groups on a substrate with gaseous 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 modification and
  • silicones or silicone-containing formulations are superior to purely organic films, coatings and coatings in many respects.
  • the use of silicone products leads to an extensive improvement of otherwise unavailable but generally desirable properties such as flow behavior, 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 relates to a process for the crosslinking of organopolysiloxane compound (S) present on a substrate which comprises at least one group of the general formula (1)
  • organopolysiloxane compound (S) is reacted with gaseous aldehyde reagent (A) of the general formula (2)
  • R is a divalent hydrocarbon radical having 1 to 20 carbon atoms, wherein the carbon chain interrupted by non-adjacent - (CO) -, -0-, -S- or -NR groups and with -CN or - Halogen may be substituted;
  • R is a hydrogen atom, a hydrocarbon radical having 1 to 20
  • 8 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 and may be covalently linked to R;
  • 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 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
  • Organopolysiloxane compound (S) coated as well as impregnated substrates Since the organopolysiloxane compound (S) first on the substrate with the gaseous aldehyde reagent (A) in
  • Organopolysiloxane compound (S) as a reactive polymer component and gaseous aldehyde reagent (A) as a crosslinking component ensure unlimited storage stability of the organopolysiloxane compound (S). The critical in other processes pot lives for coating or impregnation with
  • Organopolysiloxane compound (S) are also completely bypassed.
  • aldehyde reagents (A) can be used, for example. at 20 ° C or elevated temperatures monomer present forms of aldehydes, such as formaldehyde gas, for example, developed from aqueous or organic solution or other latent formaldehyde sources such as paraformaldehyde, trioxane or other formaldehyde condensates. Also, an aldehyde derivative such as glyoxal can be used.
  • aldehyde gas for example, developed from aqueous or organic solution or other latent formaldehyde sources such as paraformaldehyde, trioxane or other formaldehyde condensates.
  • an aldehyde derivative such as glyoxal can be used.
  • R is preferably a hydrogen atom or alkyl or aryl radicals each having 1 to 10 C atoms, more preferably a methyl radical or a hydrogen atom.
  • 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 alkyl, cycloalkyl, alkenyl, aryl or
  • Arylalkyl in particular an alkyl radical having 1 to 6 carbon atoms, more preferably a methyl radical.
  • the organopolysiloxane compound (S) used preferably contains units of the general formula (3)
  • g 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, in each case at 25 ° C.
  • the organopolysiloxane compounds (S) used are preferably substantially linear polysiloxanes having terminal and / or pendant monovalent radicals A and / or chain-containing bivalent radicals A, where A is the has the abovementioned meaning.
  • A is the 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.
  • Crosslinking of the organopolysiloxane compound (S) with the gaseous aldehyde reagent (A) leads to crosslinking units
  • Crosslinking can be carried out, for example, after application of the organopolysiloxane compound (S) by customary methods of application by gassing with the aldehyde reagent (A).
  • This contacting can be carried out at any temperature, preferably at 20 ° C or higher temperatures, more preferably at temperatures of at least 80 ° C, especially at least 100 ° C and preferably at most 180 ° C.
  • the contacting with the aldehyde reagent (A) preferably lasts at most 200 seconds, more preferably at most 10 seconds.
  • the contacting as well as the networking can be just as static under a mobile atmosphere of gaseous
  • Aldehyde reagent (A) take place.
  • the contacting as well as the crosslinking can be carried out under any pressure of the atmosphere of gaseous aldehyde reagent (A), preferably at pressures of 0.01 to 1 MPa, in particular under normal pressure (0, 10 MPa).
  • the aldehyde reagent (A) containing atmosphere may consist of gaseous aldehyde in pure form as well as other gaseous components.
  • gaseous components for example, air, nitrogen, argon or steam can be used.
  • organopolysiloxane compound (S) may also be advantageous to the organopolysiloxane compound (S) to add a catalyst for the crosslinking reaction.
  • a catalyst for the crosslinking reaction.
  • all Lewis and Bronsted acids are suitable as catalyst. These can be added directly to the silicone or applied as a separate component.
  • 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 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 invention also provides the substrate containing the organopolysiloxane compound (S) crosslinked by the process with gaseous aldehyde reagent (A).
  • the respective (aminoalkyl) polydimethylsiloxane (see Figure 1) is applied with a 20 ⁇ m doctor blade to the respective corona-pretreated film substrate (see Tables 3 - 5).
  • the coated film is then heated for 30 s at 90, 105 or 130 ° C. (see Tables 3 -5) in a gassing chamber with a continuous stream of gaseous formaldehyde and argon, generated from an aqueous solution of formaldehyde (37%) with the aid of a passed through argon stream, contacted.
  • the formaldehyde mass flow is 200 mg / min.
  • the curing takes place immediately.
  • the resulting siliconized films are tested according to standard FINAT methods (see Tables 3 - 5).
  • Table 3 Application test on HDPE film according to FINAT (company orbit) at 90 0 C.

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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)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Silicon Polymers (AREA)

Abstract

L'invention concerne un procédé de réticulation d'un composé organopolysiloxane (S) présent sur un substrat, contenant au moins un groupe représenté par la formule générale (1): -R1-NHR2. Selon le procédé, le composé organopolysiloxane (S) est mis en contact avec un réactif aldéhyde gazeux (A) représenté par la formule générale (2): O=CH-R3, 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 procédé selon l'invention, selon les revendications 1 à 6, à l'aide du réactif aldéhyde gazeux (A).
PCT/EP2009/066373 2008-12-15 2009-12-03 Réticulation d'un composé organopolysiloxane présent sur un substrat au moyen d'un réactif aldéhyde gazeux WO2010072541A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200810054679 DE102008054679A1 (de) 2008-12-15 2008-12-15 Vernetzung von auf einem Substrat vorliegender Organopolysiloxanverbindung mit gasförmigen Aldehydreagens
DE102008054679.8 2008-12-15

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WO2010072541A1 true WO2010072541A1 (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
WO2015003880A1 (fr) * 2013-07-08 2015-01-15 Wacker Chemie Ag Membranes à porosité asymétrique 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

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013213321A1 (de) 2013-07-08 2015-01-08 Wacker Chemie Ag Symmetrisch poröse Membranen aus aldehydvernetztem thermoplastischen Siliconelastomer

Citations (4)

* Cited by examiner, † Cited by third party
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
JPH0734381A (ja) * 1993-07-22 1995-02-03 Kanebo Ltd セルロース系繊維構造物の防皺加工方法
DE102007016990A1 (de) * 2007-04-11 2008-10-16 Wacker Chemie Ag Methylolgruppen enthaltende Siloxane

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Publication number Priority date Publication date Assignee Title
US3461100A (en) 1964-07-02 1969-08-12 Tracor Condensation products of aldehydes or ketones with diamines and monoamines
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
DE10047643A1 (de) 2000-09-26 2002-04-11 Basf Ag Polymere Aldehyd/Siloxan-Amin-Netzwerke
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
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
JPH0734381A (ja) * 1993-07-22 1995-02-03 Kanebo Ltd セルロース系繊維構造物の防皺加工方法
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
WO2015003880A1 (fr) * 2013-07-08 2015-01-15 Wacker Chemie Ag Membranes à porosité asymétrique 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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