WO2023139218A1 - Élastomères à base de polysiloxane et leurs procédés de production - Google Patents

Élastomères à base de polysiloxane et leurs procédés de production Download PDF

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WO2023139218A1
WO2023139218A1 PCT/EP2023/051379 EP2023051379W WO2023139218A1 WO 2023139218 A1 WO2023139218 A1 WO 2023139218A1 EP 2023051379 W EP2023051379 W EP 2023051379W WO 2023139218 A1 WO2023139218 A1 WO 2023139218A1
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weight
parts
elastomer
organic
composition
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PCT/EP2023/051379
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English (en)
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René SØNDERBÆK-JØRGENSEN
Anders E. DAUGAARD
Anne LADEGAARD SKOV
Kim Dam-Johansen
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Danmarks Tekniske Universitet
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Publication of WO2023139218A1 publication Critical patent/WO2023139218A1/fr

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    • 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
    • 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
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • 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
    • C08G77/60—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/62—Nitrogen atoms

Definitions

  • kits of parts comprising a. a first composition comprising one or more hydroxyl functional polysiloxanes as disclosed herein; and b. a second composition comprising one or more organic polysilazane as disclosed herein; wherein said kit is for preparation of the elastomer as disclosed herein.
  • polysilazane is mean a polymer compound that includes an Si-N bond, such as for example repeating units of Si-N.
  • R1 substituents may vary in between the repeating units (see also the illustrated polysiloxanes and polysilazanes used in the examples).
  • the disclosed elastomers can be produced as bulk materials, allowing for casting of object with specific three-dimensional structures.
  • the elastomer composition of the current disclosure mainly constitute a polysiloxane- based binder system wherein organic polysilazane, used for promoting curing of the system, only constitutes a minor amount of the composition.
  • the elastomer composition may be prepared from a range of different combinations of reactive polysiloxanes and polysilazanes.
  • One embodiment of the present disclosure provides for an elastomer prepared at least from a composition comprising a polysiloxane based binder system, wherein said binder system comprises: a. one or more carbinol functional polysiloxanes; and b.
  • one or more organic polysilazanes wherein said one or more organic polysilazanes constitutes 0.5-25 parts (weight) relative to 100 parts (weight) of said one or more carbinol functional polysiloxanes, wherein the elastomer is self-supported.
  • said hydroxyl functional polysiloxane has the structure of formula (la), wherein n is an integer from 5 to 7500; and wherein each Ri are independently selected from methyl; or a 2-30-membered linear or branched saturated or unsaturated chain consisting of carbon atoms, optionally wherein one or more of said carbon atoms are replaced with a moiety independently selected from the group consisting of -O-, -S-, -N-, -N-C(O)-, -O-C(O)-, -N-C(O)-N- and -N-C(O)- O- ; or a 3-30-membered saturated or unsaturated ring system consisting of carbon atoms, optionally wherein one or more of said carbon atoms are replaced with a moiety independently selected from the group consisting of -O-, -S-, -N-, -N-C(O)-, -O-C(O)-, -N-C
  • said one or more hydroxyl functional polysiloxanes comprise: a. one or more carbinol functional polysiloxanes, and/or b. one or more silanol functional polysiloxanes.
  • said one or more hydroxyl functional polysiloxane comprises a1) one or more carbinol functional polysiloxane, and optionally a2) one or more silanol functional polysiloxane.
  • 91 % such as 91 to 92 %, such as 92 to 93 %, such as 93 to 94 %, such as 94 to 95
  • the binder system comprises one or more organic polysilazanes in an amount of 0.5 to 20.0 % by dry weight. In one embodiment, the binder system comprises one or more organic polysilazanes in an amount of 0.5 to 1.0 %, such as 1.0 to 1.5 %, such as 1.5 to 2.0 %, such as 2.0 to 2.5 %, such as 2.5 to 3.0 %, such as 3.0 to 3.5 %, such as 3.5 to 4.0 %, such as 4.0 to 4.5 %, such as 4.5 to 5.0 %, such as 5.0 to 5.5.
  • % such as 5.5 to 6.0 %, such as 6.0 to 6.5 %, such as 6.5 to 7.0 %, such as 7.0 to 7.5 %, such as 7.5 to 8.0 %. such as 8.0 to 8.5 %, such as 8.5 to 9.0 %, such as 9.0 to 9.5 %, such as 9.5 to 10.0 %, such as 10.0 to 11.0 %, such as 11.0 to 12.0 %, such as 12.0 to 13.0 %, such as 13.0 to 14.0 %, such as 15.0 to 16.0 %, such as 16.0 to 17.0 %, such as 17.0 to 18.0 %, such as 18.0 to 19.0 %, such as 19.0 to 20.0 %.
  • the binder system comprises one or more hydroxyl functional polysiloxanes in an amount of 50 to 99.5 % by dry weight. In one embodiment, the binder system comprises one or more hydroxyl functional polysiloxanes in an amount of 75 to 99.5 % by dry weight. In one embodiment, the binder system comprises one or more hydroxyl functional polysiloxanes in an amount of 50 to 55 %, such as 55 to 60 %, such as 60 to 65 %, such as 65 to 70 %, such as 70 to 75 %, such as 75 to 80 %, such as 80 to 85 %, such as 85 to 90 %, such as 90 to 95 %, such as 95 to 99.5 %.
  • said one or more organic polysilazane constitutes 1-25 parts (weight), such as 1-20 parts (weight), such as 1-15 parts (weight), such as 1-10 parts (weight), such as 2-10 parts (weight), such as 3-10 parts (weight), such as 4-10 parts (weight), such as or 0.5-9 parts (weight), such as 0.5-8 parts (weight), or 0.5-7 parts (weight), or 1-9 parts (weight), or 1-8 parts (weight), or 1-7 parts (weight) or 2-9 parts (weight), preferably 2-8 parts (weight), or 2-7 parts (weight) relative to 100 parts (weight) of said one or more hydroxyl functional polysiloxane.
  • the binder system comprises one or more polysiloxanes in amount of 75 to 99.5 % by dry weight, and one or more organic polysilazanes in an amount of 0.5 to 10.0 % by dry weight. In one embodiment, the binder system comprises one or more polysiloxanes in amount of 75 to 99.5 % by dry weight, and one or more organic polysilazanes in an amount of 0.5 to 20.0 % by dry weight.
  • said one or more organic polysilazanes constitute 1-25 parts (weight), such as 1-20 parts (weight), such as 1-15 parts (weight), such as 1-10 parts (weight), such as 2-10 parts (weight), such as 3-10 parts (weight), such as 4-10 parts (weight), such as 0.5-9 parts (weight), such as 0.5-8 parts (weight), such as 0.5-7 parts (weight), such 1-9 parts (weight), such as 1-8 parts (weight), such as 1-7 parts (weight) such 2-9 parts (weight), such as 2-8 parts (weight), such as 2-7 parts (weight) relative to 100 parts (weight) of said one or more hydroxyl functional polysiloxanes.
  • said carbinol functional polysiloxane has the structure of formula
  • said carbinol functional polysiloxane has the structure of formula (la), wherein n is an integer from 5 to 7500; and wherein each Ri are independently selected from methyl; or a 2-30-membered linear or branched saturated or unsaturated chain consisting of carbon atoms, optionally wherein one or more of said carbon atoms are replaced with a moiety independently selected from the group consisting of -O-, -S-, -N-, -N-C(O)-, -O-C(O)-, -N-C(O)-N- and -N-C(O)- O- ; or a 3-30-membered saturated or unsaturated ring system consisting of carbon atoms, optionally wherein one or more of said carbon atoms are replaced with a moiety independently selected from the group consisting of -O-, -S-, -N-, -N-C(O)-, -O-C(O)-, -N-
  • said carbinol functional polysiloxane has a molecular weight in the range of 750 to 500,000 g/mol.
  • each Ri is independently selected from unsubstituted methyl or an unsubstituted 2-10 membered linear or branched saturated or unsaturated chain consisting of carbon atoms, optionally wherein one or more of said carbon atoms are replaced with a moiety independently selected from the group consisting of -O-, -S-, -N- C(O)-, -C-O-C(O)- and -N-C(O)-O-.
  • said linker is -O-.
  • Ri and R2 are as defined for compound (la); and any R2 substituent on R is denoted R2’, and R and R2’ are as defined R1 and R2 in compound (la) with the proviso that at least one of R and/or R2’ is having at least one carbinol functional group and none of R1 and R2 can have a carbinol functional group.
  • At least two of R and/or R2’ are having at least one carbinol functional group, or at least three of R and/or R2’ are having at least one carbinol functional group, or at least one of R and/or R2’ is having at least two carbinol functional groups, or at least one of R and/or R2’ are having at least three carbinol functional groups, or at least two of R and/or R2’ are having with at least two carbinol functional groups.
  • the remaining of R and/or R2’ are all selected from unsubstituted Ci-Ce alkyl, preferably unsubstituted methyl.
  • R1 are all selected independently from unsubstituted Ci-Ce alkyl, preferably all R1 are unsubstituted methyl.
  • silanol functional polysiloxane is represented by formula (lb): formula (lb)
  • said silanol functional polysiloxane is represented by formula (lb’) below having a molecular weight in the range of 750 to 500,000 g/mol: formula (lb’) wherein (m+m’+m”) is an integer from 5 to 7500; and wherein (m’+m”) is an integer from 0-50, and each R3 and each R3’ are independently selected from hydroxyl, methyl or linear or branched C1-C30 alkyl, linear or branched C2-C30 alkenyl, C3-C30 cycloalkyl or aryl; R3 is as defined for compound (lb); with the proviso that at least two R3’ groups are hydroxyl groups.
  • the molecular weight of the compound of formula (lb’) is in the range of 1000 to 500,000 g/mol, such as 1000 to 100,000 g/mol, 5000 to 100,000 g/mol or 5000 to 50,000 g/mol.
  • At least two R3’ are hydroxyl, and the remaining R3’ are selected independently from linear or branched Ci-Ce, preferably all the remaining R3’ are methyl, and all R3 are selected independently from Ci-Ce alkyl, preferably all R3 are methyl.
  • linear, branched, or cyclic structures is meant that a plurality of the moieties of formula (II) are connected as to form a linear backbone, a branched backbone, or a cyclic backbone, or a combination of any of these three structures.
  • the polysilazane may be appropriately selected according to characteristics required for a cured product. Mixtures of one or more polysilazane may be used.
  • the catalyst is selected from the group consisting of trimethylamine, triethylamine, tributylamine, 1,5-diazabicyclo[4.3.0]nonene-5 (DBN), 1 ,8-diazabicyclo[5.4.0]undecene-7 (DBU), 1 ,1,3,3-tetramethylguanidine, dimethylaminopyridine (DMAP), an azole, imidazole, an imidazole derivative, benzotriazole or a benzotriazole derivative.
  • the catalyst is a conjugated amine, such as a cyclic, conjugated amine.
  • the catalyst is a strained amine, e.g. ring-strain, such as a cyclic strained amine, such as a bicyclic strained amine, such as DBU.
  • said one or more catalysts comprise a metal catalyst.
  • said one or more metal catalysts is an organic metal catalyst.
  • the one or more catalysts constitute 0.001 to 0.5 parts relative to 100 parts (weight) of said one or more hydroxyl functional polysiloxanes. In one embodiment, the one or more catalysts constitute 0.01 to 0.1 parts relative to 100 parts (weight) of said one or more hydroxyl functional polysiloxanes.
  • the elastomers of the present disclosure may further comprise fillers, pigments, additives, and/or solvents. Fillers can assist in lowering the cost of materials while retaining the properties of the elastomer, or they may tune the mechanical or chemical properties of the elastomer. Pigments and fillers are in the present context viewed in conjunction as constituents that may be included in the elastomer composition to further modify its properties. “Pigments” are normally characterised in that they render the final elastomer nontransparent and non-translucent, whereas “fillers” normally are characterised in that they do not render the elastomer non-translucent.
  • pigments are grades of titanium dioxide, red iron oxide, zinc oxide, carbon black, graphite, yellow iron oxide, red molybdate, yellow molybdate, zinc sulfide, antimony oxide, sodium aluminium sulfosilicates, quinacridones, phthalocyanine blue, phthalocyanine green, black iron oxide, indanthrone blue, cobalt aluminium oxide, carbazole dioxazine, chromium oxide, isoindoline orange, bis-acetoacet-o-tolidiole, benzimidazolon, quinaphtalone yellow, isoindoline yellow, tetrachloroisoindolinone, quinophthalone yellow.
  • kits of parts comprising: a. a first composition comprising one or more hydroxyl functional polysiloxanes as disclosed herein; and b. a second composition comprising one or more organic polysilazanes as disclosed herein; wherein said kit is for preparation of the elastomer disclosed herein.
  • said first composition further comprises one or more catalysts as disclosed herein; or b. said kit further comprises a third composition comprising one or more catalysts as disclosed herein.
  • One embodiment of the present disclosure provides for a product comprising the elastomer disclosed herein.
  • the first composition, the second composition, and/or the third composition as described herein may be provided in a first container, a second container, and/or a third container, respectively.
  • the elastomer of the present disclosure can be manufactured using the methods disclosed herein.
  • the elastomer composition may be prepared by any suitable technique that is commonly used within the field of elastomer production.
  • the various constituents may be mixed together utilizing a mixer, a high speed disperser, a ball mill, a pearl mill, a grinder, a three-roll mill etc.
  • the elastomer compositions may be prepared and shipped as two- or three-component systems that should be combined and thoroughly mixed immediately prior to use.
  • the disclosure also relates to a kit of parts comprising two or three containers comprising components for the elastomer composition.
  • the elastomer composition is a one- component composition. Whether shipment must be performed in separate containers depends on the exact combination of polysiloxane and polysilazane.
  • the elastomer composition is typically prepared by mixing two or more components e.g. two pre-mixtures, one pre-mixture comprising the one or more reactive polysiloxane and the optional catalyst, and one pre-mixture comprising the one or more polysilazane. Both pre-mixtures may optionally comprise components selected from solvents, additives, fillers and pigments.
  • elastomer composition refers to the mixed composition comprising all constituents including the polysiloxane and the polysilazanes and optional catalyst and solvent, additives, fillers, pigments. Furthermore, all amounts stated as % by dry weight of the elastomer composition should be understood as % by dry weight of the mixed elastomer composition ready to be applied, i.e. the weight apart from the solvents (if any).
  • One embodiment provides for a method of preparing a self-supported elastomer, said method comprising mixing one or more hydroxyl functional polysiloxanes as disclosed herein and one or more of organic polysilazanes as disclosed herein, wherein said one or more organic polysilazanes constitutes 0.5-25 parts (weight) relative to 100 parts (weight) of said one or more hydroxyl functional polysiloxanes.
  • said one or more organic polysilazanes constitute 1-25 parts (weight), such as 1-20 parts (weight), such as 1-15 parts (weight), such as 1-10 parts (weight), such as 2-10 parts (weight), such as 3-10 parts (weight), such as 4-10 parts (weight), such as 0.5-9 parts (weight), such as 0.5-8 parts (weight), such as 0.5-7 parts (weight), such 1-9 parts (weight), such as 1-8 parts (weight), such as 1-7 parts (weight) such 2-9 parts (weight), such as 2-8 parts (weight), such as 2-7 parts (weight) relative to 100 parts (weight) of said one or more hydroxyl functional polysiloxanes.
  • said method further comprises adding a catalyst as disclosed herein.
  • said method does not comprise adding a catalyst, such as a catalyst disclosed herein. In one embodiment, said method further comprises adding a solvent.
  • said method further comprises adding a filler, a pigment, an additive, or a solvent as disclosed herein.
  • the elastomer is cured in a mould. In one embodiment, said method further comprises a step of liberating the elastomer from the mould. In one embodiment, the method comprises using a mould-release agent to facilitate separation of the elastomer from the mould.
  • the elastomer is cured at a temperature between 0 and 220 °C. In one embodiment, the elastomer is cured at a temperature between 0 and 80 °C.
  • the elastomer is cured without heating the composition.
  • the composition can itself develop heat from the curing reaction.
  • “without heating” is understood as not providing any additional heat, such as by heating with a heating element or a flame.
  • the method comprises a first curing period and a second curing period.
  • the method comprises the steps of: a. carrying out a first curing of the mixture for a first curing period to obtain a semicured elastomer, b. stretching or compressing the semi-cured elastomer, and c. carrying out a second curing of the semi-cured elastomer for a second curing period.
  • the first curing is carried out at a first temperature
  • the second curing is carried out at a second temperature
  • the second temperature is higher than the first temperature.
  • Pigments, fillers and solvents applied in the compositions are listed below:
  • Polysiloxanes were speed-mixed with solvent and catalyst for one minute at 3500 rpm. Thereafter polysilazane was mixed in by speed-mixing another 30 seconds.
  • Polysiloxane(s) were weighed in a large speed-mixing cup along with the hydrophobic silica filler. Filler to be added in increments, if above 10%. The two components were mixed at 3500rpm for 2 min to homogenize. This was followed by the addition of xylene and mixing for 1 min. Next step involved the addition of polysilazane and mixing for 30 sec. Next more xylene was added (0.5 mL) along with the catalyst Benzotriazole and mixing for 30 seconds. The composition is to be cast immediately after. Application (casting) of the elastomer:
  • a clean Teflon mould was kept on a level surface, determined by the spirit level.
  • the freshly prepared composition was poured into the mould and allowed to take its shape.
  • the mould was covered with a tissue cut out to cover the top and secured by tape on four sides.
  • the composition was kept under the fume hood for 48 hours. After this, the formed film was de-moulded and transferred onto a Teflon film before being placed in an oven at 80°C for 24 hours.
  • composition D presented below in Table 3 was prepared following the description under preparation of coating compositions.
  • Table 4 indicates that it is possible to adjust the curing speed by varying the type and amount of catalyst and thereby obtain a curable composition that can meet the various demands.
  • Tables 5a-f illustrate a variety of coating compositions.
  • the coating compositions follow the general preparation of pure binder and coating compositions previously described. Curing after 24 hours (yes/no) was evaluated by inspecting the films visually and by touch. A yes was given to coherent films, a no as given to compositions still in a liquid or viscous state.
  • Table 5a Exemplified elastomer compositions.
  • Table 5b exemplified compositions
  • Tables 5a and 5b shows that the various hydroxyl functional siloxane polymers can be used to obtain the curable polysiloxane composition of this disclosure.
  • Tables 5c, 5d, and 5e indicates that multiple variations in common coating ingredients that can be used without compromising the curable polysiloxane-based composition.
  • Table 5f indicates that various polysilazanes can be used to obtain a curable polysiloxane composition containing polysilazane.
  • Samples were cured at ambient conditions in a Teflon mould (size) and cut in 25 mm discs of approx. 500 pm thickness. Measurements was obtained on a TA Instruments Discovery HR-1 Hybrid Rheometer with a 25 mm parallel steel plate geometry on a Peltier temperature controlled plate. Temperature was set for 25 °C and gap was software controlled to a constant axial force of 3 N. LVE region was determined with a strain sweep at 2.5 Hz between 0.1 to 10%. Frequency sweep was recorded in a logarithmic sweep between 100 and 0.01 Hz. Strain was set at 2.5% for softer samples and 0.5% for harder samples.
  • Samples were left to cure for 2 h, and then matured for 16 h at 100 °C. Samples were cut in dog bone shapes with a thickness of 60 mm length, 6 mm width and 0.5 mm before testing. Sample tensile stress-strain behavior was tested using an Instron 3340 materials testing system at room temperature, initially separated by a distance of 30 mm. The test specimen was elongated uniaxially at 20 mm min -1 .
  • Table 6b exemplified compositions
  • Figure 1 shows the storage modulus of each elastomer composition from rheology measurements.
  • Figure 2 shows tensile measurements of selected elastomer compositions. The compositions and the storage moduli before and after post curing of the four samples at 180°C for one hour are shown in table 7 below.
  • Table 7 Storage modulus for various compositions
  • the tested compositions show elastomeric properties and that the chemical composition can be used to vary the mechanical properties of the elastomers.
  • filled systems have the expected effects as reinforcing agents and can be applied as for normal silicone systems.
  • Table 7 shows that higher amounts of the polysilazane in the composition can lead to a two-stage curing profile - compare AX, AY, and AZ. This is particularly beneficial for curing of elastomers, where a two-stage curing can be exploited to perform and fix a pre-stretch of the elastomer.
  • initial curing allows handling and stretching of the material, while a subsequent second stage curing of the stretched elastomer at higher temperature (or alternatively allowing ambient atmosphere postcuring) will add a second level of crosslinks to the elastomer.
  • This system which is reliant on only a single curing agent (polysilazane) can prove advantageous over other known systems, which may rely on two different curing agents to achieve curing in two stages.
  • said one or more hydroxyl functional polysiloxanes comprise: a. one or more carbinol functional polysiloxanes, and/or b. one or more silanol functional polysiloxanes.
  • said one or more organic polysilazanes constitute 1-25 parts (weight), such as 1-20 parts (weight), such as 1-15 parts (weight), such as 1-10 parts (weight), such as 2-10 parts (weight), such as 3-10 parts (weight), such as 4-10 parts (weight), such as 0.5-9 parts (weight), such as 0.5-8 parts (weight), such as 0.5-7 parts (weight), such 1-9 parts (weight), such as 1-8 parts (weight), such as 1-7 parts (weight) such 2-9 parts (weight), such as 2-8 parts (weight), such as 2-7 parts (weight) relative to 100 parts (weight) of said one or more hydroxyl functional polysiloxanes.
  • carbinol functional polysiloxane has the structure of formula (la) having a molecular weight in the range of 750 to 500,000 g/mol: wherein n is an integer from 5 to 7500; and wherein each Ri are independently selected from methyl; or a 2-30-membered linear or branched saturated or unsaturated chain consisting of carbon atoms, optionally wherein one or more of said carbon atoms are replaced with a moiety independently selected from the group consisting of -O-, -S-, -N-, -N-C(O)-, -O-C(O)-, -N-C(O)-N- and -N-C(O)- O- ; or a 3-30-membered saturated or unsaturated ring system consisting of carbon atoms, optionally wherein one or more of said carbon atoms are replaced with a moiety independently selected from the group consisting of -O
  • the elastomer according to any one of the preceding items wherein the molecular weight of the compound having the structure of formula (la) is in the range of 1000 to 500,000 g/mol, such as 1000 to 100,000 g/mol, 5000 to 100,000 g/mol or 5000 to 50,000 g/mol.
  • each optionally substituted R1 is having a molecular weight of less than 450 g/mol, such as less than 400 g/mol, such as less than 350 g/mol, such as less than 300 g/mol.
  • n is an integer from 5 to 5000; such as from 5 to 4000, such as from 5 to 3000, such as from 5 to 2000, preferably from 5 to 1000, such as from 20 to 1000, such as from 20 to 500.
  • each R1 is independently selected from unsubstituted methyl or an unsubstituted 2-10 membered linear or branched saturated or unsaturated chain consisting of carbon atoms, optionally wherein one or more of said carbon atoms are replaced with a moiety independently selected from the group consisting of -O-, -S-, -N-C(O)-, -C- O-C(O)- and -N-C(O)-O-.
  • the elastomer according to any one of the preceding items wherein the molecular weight of the compound of formula (lb) is in the range of 1000 to 500,000 g/mol, such as 1000 to 100,000 g/mol, such as 5000 to 100,000 g/mol, such as 5000 to 50,000 g/mol.
  • m is an integer from 5 to 5000; such as from 5 to 4000, such as from 5 to 3000, such as from 5 to 2000, such as from 5 to 1000, such as from 20 to 1000, such as from 20 to 500.
  • said one or more organic polysilazane comprises a compound having the structure of formula (II), wherein the compound has a linear or branched or cyclic structure: wherein p is an integer from 5 to 100; wherein each R4 are independently selected from hydrogen, linear or branched Ci-Ce alkyl or linear or branched Ci-Ce alkenyl; and each R5 are independently selected from hydrogen, linear or branched Ci-Ce alkyl or linear or branched Ci-Ce alkenyl; wherein at least one R4 is not hydrogen.
  • the composition further comprising one or more catalysts.
  • organic amine is selected from the group consisting of trimethylamine, triethylamine, tributylamine, 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8- diazabicyclo[5.4.0]undec-7-ene (DBU), 1 ,1,3,3-tetramethylguanidine, 4- dimethylaminopyridine (DMAP), an azole, imidazole, an imidazole derivative, benzotriazole, and a benzotriazole derivative.
  • said polysiloxane-based binder system constitutes at least 40 % by dry weight, such as 40-98 % by dry weight, such 45-95 % by dry weight, such as 50-95 % by dry weight, such as 50-90 % by dry weight, such as 55-90 % by dry weight, such as 60- 90 % by dry weight, of the elastomer.
  • elastomer according to any one of the preceding items, wherein the elastomer further comprises one or more of a filler, a pigment, an additive, or a solvent.
  • kits of parts comprising: a. a first composition comprising one or more carbinol functional polysiloxanes according to any one of the preceding items; and b. a second composition comprising one or more organic polysilazane according to any one of the preceding items; wherein said kit is for preparation of the elastomer according to any one of the preceding items.
  • a kit of parts comprising: a. a first composition comprising one or more hydroxyl functional polysiloxanes according to any one of the preceding items; and b. a second composition comprising one or more organic polysilazane according to any one of the preceding items; wherein said kit is for preparation of the elastomer according to any one of the preceding items.
  • a. said first composition further comprises one or more catalysts according to any one of the preceding items; or b. said kit further comprises a third composition comprising one or more catalysts according to any one of the preceding items.
  • kits of parts comprising a. a first composition comprising one or more carbinol functional polysiloxane according to any one of the preceding items; and one or more organic polysilazanes according to any one of the preceding items; and b. a second composition comprising one or more catalysts according to any one of the preceding items; wherein said kit is for preparation of the elastomer according to any one of the preceding items.
  • kits of parts comprising a. a first composition comprising one or more hydroxyl functional polysiloxane according to any one of the preceding items; and one or more organic polysilazanes according to any one of the preceding items; and b. a second composition comprising one or more catalysts according to any one of the preceding items; wherein said kit is for preparation of the elastomer according to any one of the preceding items.
  • a product comprising the elastomer according to any one of the preceding items.
  • a method of preparing the self-supported elastomer according to any one of the preceding items comprising mixing one or more of the hydroxyl functional polysiloxanes according to any one of the preceding items and one or more of the organic polysilazanes according to any one of the preceding items, wherein said one or more organic polysilazanes constitutes 0.5-25 parts (weight) relative to 100 parts (weight) of said one or more hydroxyl functional polysiloxanes.
  • a method of preparing a self-supported elastomer comprising mixing one or more carbinol functional polysiloxanes according to any of the preceding items and one or more of organic polysilazanes according to any one of the preceding items, wherein said one or more organic polysilazanes constitutes 0.5-25 parts (weight) relative to 100 parts (weight) of said one or more carbinol functional polysiloxanes.
  • a method of preparing a self-supported elastomer comprising mixing one or more hydroxyl functional polysiloxanes according to any one of the preceding items and one or more of organic polysilazanes according to any one of the preceding items, wherein said one or more organic polysilazanes constitutes 0.5-25 parts (weight) relative to 100 parts (weight) of said one or more hydroxyl functional polysiloxanes.
  • said one or more organic polysilazanes constitute 1-25 parts (weight), such as 1-20 parts (weight), such as 1-15 parts (weight), such as 1-10 parts (weight), such as 2-10 parts (weight), such as 3-10 parts (weight), such as 4-10 parts (weight), such as 0.5-9 parts (weight), such as 0.5-8 parts (weight), such as 0.5-7 parts (weight), such 1-9 parts (weight), such as 1-8 parts (weight), such as 1-7 parts (weight) such 2-9 parts (weight), such as 2-8 parts (weight), such as 2-7 parts (weight) relative to 100 parts (weight) of said one or more hydroxyl functional polysiloxanes.
  • said solvent is selected from the group consisting of aliphatic solvents, cycloaliphatic solvents, and aromatic hydrocarbons, such as white spirit, cyclohexane, toluene, xylene and naphtha solvent, esters such as methoxypropyl acetate, n-butyl acetate and 2- ethoxyethyl acetate, water, and mixtures thereof.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Silicon Polymers (AREA)

Abstract

L'invention concerne des élastomères préparés au moins à partir d'une composition comprenant un système de liant à base de polysiloxane, ledit système de liant comprenant un ou plusieurs polysiloxanes à fonction hydroxyle et un ou plusieurs polysilazanes organiques. L'invention concerne également des procédés de production de tels élastomères.
PCT/EP2023/051379 2022-01-21 2023-01-20 Élastomères à base de polysiloxane et leurs procédés de production WO2023139218A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0384183A2 (fr) * 1982-02-17 1990-08-29 General Electric Company Mélanges comprenant des polydiorganosiloxanes ayant des groupes silanols terminaux et procédés de préparation
US4987155A (en) * 1989-07-26 1991-01-22 Shin-Etsu Chemical Co., Ltd. Foamable organopolysiloxane composition
WO2000077102A1 (fr) 1999-06-11 2000-12-21 J.C. Hempel's Skibsfarve-Fabrik A/S Composition de peinture antisalissures marine autopolissante comprenant des copolymeres qui contiennent du silicium et des fibres
JP2012153849A (ja) 2011-01-28 2012-08-16 Yokohama Yushi Kogyo Kk 新規コーティング剤
US9676946B2 (en) 2013-07-02 2017-06-13 Az Electronic Materials (Luxembourg) S.A.R.L. Coating composition
EP3733801A1 (fr) 2017-12-26 2020-11-04 ThreeBond Co., Ltd. Composition formant un film de revêtement

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0384183A2 (fr) * 1982-02-17 1990-08-29 General Electric Company Mélanges comprenant des polydiorganosiloxanes ayant des groupes silanols terminaux et procédés de préparation
US4987155A (en) * 1989-07-26 1991-01-22 Shin-Etsu Chemical Co., Ltd. Foamable organopolysiloxane composition
WO2000077102A1 (fr) 1999-06-11 2000-12-21 J.C. Hempel's Skibsfarve-Fabrik A/S Composition de peinture antisalissures marine autopolissante comprenant des copolymeres qui contiennent du silicium et des fibres
JP2012153849A (ja) 2011-01-28 2012-08-16 Yokohama Yushi Kogyo Kk 新規コーティング剤
US9676946B2 (en) 2013-07-02 2017-06-13 Az Electronic Materials (Luxembourg) S.A.R.L. Coating composition
EP3733801A1 (fr) 2017-12-26 2020-11-04 ThreeBond Co., Ltd. Composition formant un film de revêtement

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BAROSSO ET AL.: "Polysilazane-Based Coatings with Anti-Adherent Properties for Easy Release of Plastics and Composites from Metal Molds", ADV. MATER. INTERFACES, vol. 7, 2020, pages 1901952

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