WO2023200497A1 - Hydrosilylation curable polyether formulations - Google Patents
Hydrosilylation curable polyether formulations Download PDFInfo
- Publication number
- WO2023200497A1 WO2023200497A1 PCT/US2023/010994 US2023010994W WO2023200497A1 WO 2023200497 A1 WO2023200497 A1 WO 2023200497A1 US 2023010994 W US2023010994 W US 2023010994W WO 2023200497 A1 WO2023200497 A1 WO 2023200497A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- addition reaction
- units
- reaction curable
- average
- less
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- 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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
-
- 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
- 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
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
-
- 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
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
Definitions
- the present invention relates to an addition reaction curable polyether composition that does not require phenyl-functionalized silicone crosslinkers as a compatiblizing crosslinker.
- Silane modified polymers are a class of materials that consist of an organic polymer backbone terminated with silane groups. SMPs are useful in formulating adhesives and sealants, such as room temperature vulcanizable (RTV) sealants, utilizing the reactivity of the silane terminal groups for curing.
- RTV room temperature vulcanizable
- Two types of currently available SMPs are silane terminated poly ethers (STPE) and silane modified polyurethanes (STPU).
- STPE silane terminated poly ethers
- STPU silane modified polyurethanes
- Silane terminated polyethers tend to offer a lower modulus and better durability than silane terminated polyurethanes so they are often more desirable, particularly in sealant applications.
- SMP compositions cure through polycondensation so they require moisture to cure.
- polycondensation curing of SMP compositions utilizes atmospheric moisture to cure. That means there must be atmospheric moisture present to achieve curing. Additionally, it means that moisture must penetrate into the SMP composition to effect a thorough cure.
- cure rates of SMP compositions are dependent on the available moisture and the rate at which that moisture can penetrate into the SMP material.
- atmospheric moisture is low (such as arid geographies) curing is difficult to achieve. Even when atmospheric moisture is present, moisture penetration is typically slow into SMP materials so thorough curing can take anywhere from hours to days to achieve.
- VOCs volatile organic compounds
- an addition reaction curable polyether composition that does not require phenyl-functionalized silicone crosslinkers yet that has components that are compatible with one another and that cures at 80 degrees Celsius (°C) within 90 minutes and preferably within 24 hours at 25 °C.
- the present invention provides an addition reaction curable polyether composition that does not require phenyl-functionalized silicone crosslinkers yet that has components that are compatible with one another.
- the addition reaction curable polyether composition can cure at 80 degrees Celsius (°C) within 90 minutes and in some cases can cure within 24 hours at 25 °C. In fact, the entire composition can be free from phenyl-functionalized silicone crosslinkers, and can even be free of phenyl-functionalized components altogether.
- the present invention is a result of discovering that silyl hydride functional silicone resins that, relative to all siloxane units in the resin, comprises 90 mole-percent (mol%) or more and can comprise 95 mol% or more, even 99 mol% or more, even 100 mol% of a combination of SiO4/2, H(R 1 )2SiOi/2 and optionally (R ⁇ gSiOi ⁇ siloxane units, with mol% relative to total siloxane units and preferably all copolymerized units in the SiH functional polysiloxane, are compatible with alkenyl functional polyethers and suitable crosslinkers in phenyl-free silane modified polyether compositions that cure by addition chemistry rather than polycondensation.
- the present invention is an addition reaction curable polyether composition
- a poly ether with an average of 1.4 or more unsaturated carbon-carbon bonds per molecule (b) one or a combination of more than one silyl-hydride functional polysiloxane crosslinker that is free of phenyl groups and that comprises 90 mole-percent or more of a combination of the following siloxane units: H(R 3 )2SiOi/2, SiO 4 /2 and optionally (R 3 )3SiOi/2 where the average number per molecule of H(R 3 )2SiOi/2 units is 2 or more, the average number per molecule of SiO 4 /2 units is one or more and the average number per molecule of (R 3 )3SiOi/2 units is such that the number of (R 3 )3SiOi/2 units divided by the sum of H(R 3 )2SiOi/2 and (R 3 )3SiOi/2 units is less than
- the present invention is a process for using the addition reaction curable polyether composition of the previous aspect, the process comprising disposing the addition reaction curable polyether composition onto another material and then curing the addition reaction curable polyether composition by heating to 80 degrees Celsius or higher.
- the addition reaction curable polyether composition of the present invention is useful as a composition that can be used, for example, as a sealant or adhesive.
- Test methods refer to the most recent test method as of the priority date of this document when a date is not indicated with the test method number. References to test methods contain both a reference to the testing society and the test method number. The following test method abbreviations and identifiers apply herein: ASTM refers to American Society for Testing and Materials; EN refers to European Norm; DIN refers to Deutsches Institut fur Normung; and ISO refers to International Organization for Standards.
- propylene oxide units as[OCH2CH(CH3)], but is it to be understood and is intended that the chemical structure are not limited to that orientation of the propylene oxide.
- the propylene oxide units can be [OCH2CH(CH3)], [OCH(CH3)CH2], or a combination of the two orientations.
- Siloxane units can be characterized by the designation M, D, T or Q.
- M refers to a siloxane unit having the formula “(CH3)3SiOi/2”.
- D refers to a siloxane unit having the formula “(CH3)2SiO2/2 ”
- T refers to a siloxane unit having the formula “(CH3)SiO3/2”.
- Q refers to a siloxane unit having the formula “SiO4/2”.
- Non-oxygen groups bound to the silicon atom in M, D and T units are methyl groups unless otherwise stated or indicated.
- an oxygen atom having a multiple of “1/2” subscript indicates that the oxygen bridges the specified atom to a second atom where the second atom is also specified with an oxygen having a multiple of “1/2” subscript.
- ((CH ⁇ SiOi/i) (SiO4/2), or MQ refers to a M unit bound to a Q unit with an oxygen atom shared between the silicon atom of the M unit and a silicon atom o the Q unit.
- the multiplier of the Vi subscript indicates how many oxygen atoms are in such a shared bonding configuration with the silicon atom of the siloxane unit.
- siloxane unit designation with the suffix “-type” refers to the siloxane unit where any one or more than one methyl group is actually an R group where R is a group other than methyl such as hydroxyl, alkoxyl, or hydrocarbyl.
- the hydrocarbyl typically contains from one to 8 carbon atoms.
- R can be methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, or octyl.
- a siloxane unit can include as a superscript an indication of a group bound to that silicon atom in place of an alkyl group.
- M H -type unit refers to an M-type unit with one R group replaced with hydrogen: FR 1 JiHSiOi/i).
- M H ” unit refers to an M unit with one methyl replaced with a hydrogen atom GCH jiHSiO 1/2).
- T ph unit refers to a T unit with the methyl replaced with a phenyl group.
- Chemical formula designations for polysiloxanes using M,D,T,Q abbreviations typically have subscripts associated with the unit designator that can either refer to the average mole ratio of that siloxane unit relative to all siloxane units in the molecule or the average number of the associate siloxane units in the molecule.
- the subscript associated with a siloxane unit is greater than or equal to one, then the subscript refers to the average number of those siloxane units in the molecule.
- the subscript associated with a siloxane unit is less than one then the subscript refers to the average mole ratio of that siloxane unit relative to the number of moles of all siloxane units in the molecule.
- An absence of a subscript implies a subscript value of one.
- the addition reaction curable polyether composition of the present invention comprises a polyether having unsaturated carbon-carbon bonds, preferably in the form of allyl and/or methallyl functional groups.
- the polyether can be linear or branched, or be a combination of linear and branched polyethers.
- the polyether can be free of phenyl groups.
- the polyether has an average of 1.4 or more, preferably 1.6 or more, 1.7 or more, even 1.8 or more, and can have an average of 2.0 or more unsaturated carbon-carbon bonds per molecule while at the same time typically has an average of 5 or fewer, 4 or fewer, 3 or fewer, even 2 or fewer unsaturated carbon-carbon bonds per molecule.
- the polyether is not particularly limited, and various polyethers can be used. Typical examples thereof include polyethers having a main chain of recurring ( - R 1 -0- ) units, where -R 1 - represents a bivalent alkylene group.
- the polyether may have one kind of recurring unit or multiple kinds of recurring units, that is, R 1 may be the same or different in recurring units.
- the polyether may be a linear polymer or a branched polymer.
- the polyether can, and typically does, contain a small amount of other units that may or may not be reoccurring along the polymer chain.
- the other units can be from initiator used to synthesize the polymer for instance.
- Initiators can be any chemical species that can be catalyzed to polymerize poly ether precursors. Examples of suitable initiators include glycerol and 1,4- butane diol.
- the main chain of the poly ether is favorably polyoxypropylene (that is, -R 1 - above is -CH2CH(CH3)-).
- Poly ethers having polyoxypropylene as the main chain are favorable from the points of commercial availability and processability. All of the regions of the polyether other than those of unsaturated carbon-carbon bond groups preferably have polyoxyalkylene skeletons, but the region may contain other structural units too. In such a case, the total amount of the polyether skeleton in the polymer is preferably 80 wt % or more, more preferably 90 wt % or more relative to weight of the polyether.
- the numberaverage molecular weight of the polyether is preferably 3000 or more, even 5000 or more while at the same time is typically 50000 or less, preferably 40000 or less, from the points of processability at room temperature and adhesive properties.
- a polyether having a number-average molecular weight of less than 3000 often gives a cured product that is more brittle, while a polyether having a number- average molecular weight of more than 50000 is more viscous, leading to deterioration in processability.
- the addition reaction curable polyether composition can comprise a combination of polyethers having different molecular weights, which can be desirable when properties of a broad molecular weight distribution are needed or desired.
- the molecular weight above is the number-average molecular weight as polystyrene that is determined by gel permeation chromatography (GPC).
- the bond of the unsaturated carbon-carbon double bond group to the polyether is not particularly limited, and examples thereof include direct bond of alkenyl group ether, ester bond, carbonate bond, urethane bond, urea bond, and the like.
- the polyether can, for example, be a linear or branched allyl or a methallyl capped polypropylene oxide or a combination thereof.
- the polymer is selected from any one or any combination of more than one of the following three exemplary poly ethers: First, a tri-branched polypropylene oxide having an average chemical structure (I):
- the value of m is the average number of propylene oxide units in a given polyether segment and can be the same or different for each of the three polyether segments provided that the value for m is greater than zero in each of the three segments and the average value of the sum of all three m values is 60 or more, 80 or more, 100 or more, 125 or more, 150 or more, 200 or more, 250 or more, 300 or more, 350 or more, 375 or more, 385 or more, even 400 or more, while at the same time 1000 or less, 750 or less, 700 or less, 600 or less, 500 or less, 400 or less, or even 385 or less or less; and
- R 2 is a trivalent hydrocarbyl group, meaning it is a hydrocarbyl group with the three polyether chains attached thereto.
- R 2 can have the chemical structure -CH(CH 2 -)- with a polyether chain attached at each
- R 4 is a divalent hydrocarbyl preferably containing one or more and can contain 2 or more 3 or more 4 or more, 5 or more, 6 or more, 7 or more, even 8 or more while at the same time typically contains 10 or fewer, 9 or fewer, 8 or fewer, 7 or fewer, 6 or fewer, 5 or fewer, 4 or fewer, even 3 or fewer carbon atoms; and subscript n is the average number of propylene oxide units in each of the two polypropylene oxide groups extending off from R 4 and can independently in each occurrence have an average value of 10 or more, 20 or more, 50 or more, 60 or more, 75 or more, 100 or more, even 125 or more while at the same time typically has an average value of 1600 or less, 1400 or less, 1200 or less, 1000 or less, 750 or less, 500 or less, 250 or less, 200 or less, and can
- R 4 is a divalent hydrocarbyl preferably containing one or more and can contain 2 or more 3 or more 4 or more, 5 or more, 6 or more, 7 or more, even 8 or more while at the same time typically contains 10 or fewer, 9 or fewer, 8 or fewer, 7 or fewer, 6 or fewer, 5 or fewer, 4 or fewer, even 3 or fewer carbon atoms; and subscript o is the average number of propylene oxide units in each of the two polypropylene oxide groups extending off from R 4 and can independently in each occurrence have an average value of 10 or more, 20 or more, 50 or more, 60 or more, 65 or more, 75 or more, 100 or more, even 125 or more while at the same time typically has an average value of 1600 or less, 1400 or less, 1200 or less, 1000 or less, 750 or less, 500 or less, 250 or less
- the addition reaction curable polyether composition also comprises one or a combination of more than one silyl-hydride (SiH) functional polysiloxane crosslinkers.
- SiH functional polysiloxane crosslinkers are free of phenyl groups.
- the SiH functional polysiloxane crosslinkers comprise 90 mole-percent (mol%) or more and can comprise 95 mol% or more, even 99 mol% or more, even 100 mol% of a combination of the following siloxane units, with mol% relative to total siloxane units and preferably all copolymerized units in the SiH functional polysiloxane crosslinker: SiO4/2, H(R 3 )2SiOi/2 and optionally (R 3 )3SiOi/2-
- Each R 3 is independently in each occurrence selected from hydrocarbyl groups having one or more and can have 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, even 7 or more while at the same time typically has 8 or fewer, 7 or fewer, 6 or fewer, 5 or fewer, 4 or fewer, 3 or fewer, or even 2 or fewer carbon atoms.
- Each R 3 can be the same or there can be different R 3 groups in the same molecule. Desirably,
- the SiH functional polysiloxane crosslinker contains on average one or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 10 or more 15 or more, even 20 or more while at the same time typically 40 or fewer, 30 or fewer, 25 or fewer, 20 or fewer, even 15 or fewer SiO4/2 siloxane units per molecule.
- the SiH functional polysiloxane crosslinker contains on average 2 or more and can contain 3 or more, 4 or more, 5 or more, 6 or more, 10 or more, 15 or more, even 20 or more while at the same time typically contains 40 or fewer and can contain 30 or fewer, 25 or fewer, 20 or fewer, 15 or fewer, 10 or fewer, 8 or fewer, 7 or fewer, 6 or fewer, even 5 or fewer H(R 3 )2SiOi/2 units per molecule.
- the SiH functional polysiloxane crosslinker contains on average zero or more, one or more and can contain 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 10 or more, even 20 or more while at the same time typically contains 30 or fewer and can contain 20 or fewer, 15 or fewer, 10 or fewer, 8 or fewer, 7 or fewer, 6 or fewer, even 5 or fewer (R 3 )3SiOi/2 units per molecule provided that the average number per molecule of (R 3 )3SiOi/2 units is such that the number of (R 3 )3SiOi/2 units divided by the sum of H(R 3 )2SiOi/2 and (R 3 )3SiOi/2 units is less than 0.7, and can be 0.6 or less, 0.5 or less, 0.4 or less, 0.3 or less, 0.2 or less, 0.1 or less, or even zero.
- Siloxane “resins” contain T-type and Q-type siloxane units and typically contain non-fully condensed Q-type, T-type and sometimes D-type siloxane units with “-OZ” groups where Z is selected from H or an alkyl group having one or more, or two or more and at the same time 8 or fewer, typically 6 or fewer carbon atoms.
- concentration of -OZ groups in a siloxane resin is 5 mole-percent (mol%) or less based on moles of siloxane units in the resin.
- “resins” are presumed to contain up to 5 mol% based on moles of siloxane units in the resin even if the -OZ component is not specified in a formula for the resin.
- the addition reaction curable polyether composition further comprises a hydrosilylation catalyst.
- the hydrosilylation catalyst is a platinum-based hydrosilylation catalyst.
- Platinum-based hydrosilylation catalysts include compounds and complexes such as platinum (0)-l,3-divinyl-l,l,3,3-tetramethyldisiloxane (Karstedt’s catalyst), platinum-carbonyl complexes, platinum cyclovinylmethylsiloxane complexes, platinum acetylacetonate (acac), cyclopentadienyl alky platinum, platinum black, platinum compounds such as chloroplatinic acid, chloroplatinic acid hexahydrate, a reaction product of chloroplatinic acid and a monohydric alcohol, platinum bis(ethylacetoacetate), platinum bis(acetylacetonate), platinum dichloride, and complexes of the platinum compounds with olefins or low molecular weight organopolysiloxanes or platinum compounds
- the catalyst can be a supported Pt catalysts with Pt metal particles or compounds adsorbed onto or absorbed into a support material such as carbon or alumina.
- the hydrosilylation catalyst can be part of a solution that includes complexes of platinum with low molecular weight organopolysiloxanes that include l,3-diethenyl-l,l,3,3-tetramethyldisiloxane complexes with platinum. These complexes may be microencapsulated in a resin matrix.
- Other transition or noble metal compounds can also be used as hydrosilylation catalysts, for example, di-p.-carbonyl di- .71.- cyclopentadienyl dinickel.
- the addition reaction curable polyether composition can further comprise, or be free of, a chain extender component that contains an average of two SiH groups per molecule and that is free of SiO4/2 siloxane units.
- the chain extender can comprise or be free of phenyl groups.
- the chain extender can have an average chemical composition: HR 2SiOPh2SiOSiR 2H where “Ph” refers to a phenyl group and R is as defined above, and is preferably methyl.
- the concentration of chain extender is typically 2 wt% or less, and can be 1.8 wt% or less, 1.6 wt% or less, 1.4 wt% or less, 1.2 wt% or less, 1.0 wt% or less, 0.8 wt% or less, 0.6 wt% or less, 0.3 wt% or less, 0.1 wt% or less or even 0 wt% of the addition reaction curable polyether composition weight.
- the addition reaction curable polyether composition can further comprise, or be free of, a hydrosilylation catalyst inhibitor.
- suitable hydrosilylation catalyst inhibitors include any one or any combination of more than one of acetylene-type compounds such as 2-methyl-3-butyn-2-ol; 3-methyl-l-butyn-3-ol; 3,5-dimethyl- l-hexyn-3- ol; 2-phenyl-3-butyn-2-ol;3-phenyl- l-butyn-3-ol; 1-ethynyl-l-cyclohexanol; 1,1-dimethyl- 2-propynyl)oxy)trimethylsilane; and methyl(tris(l,l-dimethyl-2-propynyloxy))silane; ene- yne compounds such as 3-methyl-3-penten-l-yne and 3,5-dimethyl-3-hexen-l-yne; triazols such as benzo triazole;
- the concentration of hydrosilylation catalyst inhibitor as a mole-ratio relative to platinum from the catalyst can be zero or more, 0.5 or more, 1.0 or more, 5.0 or more, 10 or more, 20 or more, 30 or more, 40 or more, 50 or more, even 100 or more while at the same time is typically 200 or less, 100 or less, 50 or less, 40 or less, 30 or less, 20 or less, 10 or less, 5 or less, and can be 1.0 or less.
- the addition reaction curable polyether composition can further comprise, or be free of, an “additional” SiH functional crosslinker containing an average of 2 or more, preferably 3 or more SiH functional groups per molecule where the additional SiH functional crosslinker does not meet the qualification of the SiH functional polysiloxane crosslinker described hereinabove.
- the additional SiH functional crosslinker can contain Ph groups or be free of Ph groups.
- the SiH functional crosslinker can comprise SiO4/2 siloxane units or be free of SiO4/2 siloxane units.
- the addition reaction curable polyether composition can be free of SiH functional polysiloxane having phenyl functionality.
- the SiH functional crosslinker can be cyclic or non-cyclic.
- the additional SiH functional crosslinker can also be non-cyclic.
- the addition reaction curable polyether composition can be free of cyclic SiH functional crosslinkers.
- the present invention further includes a process for using the addition reaction curable polyether composition.
- the process comprises disposing the addition reaction curable polyether composition onto another material, a substrate for example, and then curing the addition reaction curable polyether composition by heating it, preferably to a temperature of 80 degrees Celsius (°C) or higher.
- Table 1 identifies components used in the following examples. Me refers to methyl and Ph refers to phenyl.
- DOWSIL is a trademark of The Dow Chemical Company.
- SYL-OFF is a trademark of Dow Silicones Corporation.
- Components for the sample compositions are in the tables below. Dry the polyether component under vacuum at 110 degrees Celsius (°C) for 12 hours and store in a glovebox. Combine the polyether with the catalyst component inside a glovebox using a Flacktec SpeedMixerTM (Flacktek SpeedMixer is a trademark of Flacktec, Inc.) at 2500 revolutions per minute (RPM) for 30 seconds. Add the SiH Crosslinker component while inside the glovebox and mix using a Flacktek SpeedMixerTM at 2500 RPM for 30 seconds.
- Flacktec SpeedMixerTM Fracktek SpeedMixer is a trademark of Flacktec, Inc.
- Compatibility Assess compatibility of the components of a composition by visual inspection of the composition mixture in a glass vial. “Transparent”, or “T”, mixtures indicate complete compatibility. “Hazy”, or “H”, mixtures indicate particle compatibility. “Opaque”, or “O”, mixtures indicate immiscible incompatibility.
- Cure Results Curing assessments are done for each composition after curing 30 minutes and 90 minutes at 80 °C in order to determine the state of curing.
- a value of “1” is assigned to samples that are “well cured” to a solid piece of material that is visually uniform from top to bottom with hardened surfaces evident from poking the surface with a spatula.
- a value of “2” is assigned to samples that are “cured but sticky”, which are cured compositions that have a sticky surface.
- a value of “3” is assigned to samples that have a viscosity increase but are not cured to a solid piece of material.
- a value of “4” is assigned to samples that remail fluid without significant change of viscosity and are deemed “noncured” samples.
- Tables 2 and 3 list the components for each sample in grams (hydrosilylation catalyst in weight parts per million weight parts composition) as well as evaluation results for compatibility and curing.
- the only compositions in Table 2 that achieve compatibility and full cure even in 80 minutes are compositions that contain only SiH-functional crosslinkers that include phenyl functionality.
- compositions in Table 3 demonstrate compatible components and full cure within 80 minutes, with some reaching full cure in only 30 minutes.
- compositions in Table 3 use an SiH functional crosslinker that does not contain phenyl functionality and that comprise 90 mole-percent or more of a combination of the following siloxane units: H(R 3 )2SiOi/2, SiO4/2 and optionally (R 3 )3SiOi/2 where the average number per molecule of H(R 3 )2SiOi/2 units is 2 or more, the average number per molecule of SiO4/2 units is one or more and the average number per molecule of (R 3 )3SiOi/2 units is such that the number of (R 3 )3SiOi/2 units divided by the sum of H(R 3 )2SiOi/2 and (R 3 )3SiOi/2 units is less than 0.7; where R 3 is independently in each occurrence selected from hydrocarbyl groups having from one to 8 carbon atoms.
- Table 3 includes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Silicon Polymers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18/850,096 US20250215163A1 (en) | 2022-04-13 | 2023-01-18 | Hydrosilylation curable polyether formulations |
| EP23706155.1A EP4508117A1 (en) | 2022-04-13 | 2023-01-18 | Hydrosilylation curable polyether formulations |
| JP2024558209A JP2025512293A (ja) | 2022-04-13 | 2023-01-18 | ヒドロシリル化硬化型ポリエーテル配合物 |
| KR1020247037009A KR20250003709A (ko) | 2022-04-13 | 2023-01-18 | 하이드로실릴화 경화성 폴리에테르 제형 |
| CN202380029413.XA CN119013332A (zh) | 2022-04-13 | 2023-01-18 | 可氢化硅烷化固化的聚醚制剂 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202263330348P | 2022-04-13 | 2022-04-13 | |
| US63/330,348 | 2022-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2023200497A1 true WO2023200497A1 (en) | 2023-10-19 |
Family
ID=85284006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2023/010994 Ceased WO2023200497A1 (en) | 2022-04-13 | 2023-01-18 | Hydrosilylation curable polyether formulations |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20250215163A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP4508117A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2025512293A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20250003709A (cg-RX-API-DMAC7.html) |
| CN (1) | CN119013332A (cg-RX-API-DMAC7.html) |
| TW (1) | TW202340378A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2023200497A1 (cg-RX-API-DMAC7.html) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021126516A1 (en) * | 2019-12-16 | 2021-06-24 | Dow Silicones Corporation | Low isomer hydrosilylation |
-
2023
- 2023-01-18 US US18/850,096 patent/US20250215163A1/en active Pending
- 2023-01-18 EP EP23706155.1A patent/EP4508117A1/en active Pending
- 2023-01-18 WO PCT/US2023/010994 patent/WO2023200497A1/en not_active Ceased
- 2023-01-18 CN CN202380029413.XA patent/CN119013332A/zh active Pending
- 2023-01-18 KR KR1020247037009A patent/KR20250003709A/ko active Pending
- 2023-01-18 JP JP2024558209A patent/JP2025512293A/ja active Pending
- 2023-03-08 TW TW112108573A patent/TW202340378A/zh unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021126516A1 (en) * | 2019-12-16 | 2021-06-24 | Dow Silicones Corporation | Low isomer hydrosilylation |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20250003709A (ko) | 2025-01-07 |
| EP4508117A1 (en) | 2025-02-19 |
| CN119013332A (zh) | 2024-11-22 |
| TW202340378A (zh) | 2023-10-16 |
| US20250215163A1 (en) | 2025-07-03 |
| JP2025512293A (ja) | 2025-04-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4167737B2 (ja) | シリコーン接着剤組成物 | |
| JP7170105B2 (ja) | 反応性有機ケイ素揺変剤、有機ケイ素パッケージ接着剤及びled素子 | |
| JP7263616B2 (ja) | 二重硬化性組成物 | |
| EP2276794A1 (en) | Silicon-containing polymer, method of manufacturing thereof, and curable polymer composition | |
| EP4508117A1 (en) | Hydrosilylation curable polyether formulations | |
| EP4073143A1 (en) | Rapid hydrosilylation cure composition | |
| JP7203197B2 (ja) | 架橋性オルガノシロキサン組成物 | |
| EP4010406B1 (en) | Organopolysiloxane cluster polymer for rapid air cure | |
| US9045599B2 (en) | Amphiphilic resin-linear organosiloxane block copolymers | |
| CN118843652A (zh) | 制备聚醚官能有机硅化合物 | |
| EP3581607B1 (en) | Novel mesogen-silicon compound (co)polymer and thermoplastic elastomer | |
| CN113227237A (zh) | 粘接性聚有机硅氧烷组合物 | |
| WO2025106161A1 (en) | Hydrosilylation pressure sensitive adhesive composition with 1-cod | |
| EP4592300A1 (en) | Cyclic organopolysiloxane, silicone composition, adhesion promoter, and adhesive | |
| WO2025194325A1 (en) | Silicone optically clear adhesive with high substrate adhesion | |
| WO2025179440A1 (en) | Silicone optically clear adhesive with high substrate adhesion and high shock absorbance | |
| WO2023191962A1 (en) | Rapid low temperature curing moldable silicone compositions | |
| WO2026016121A1 (en) | Shock absorbing silicone elastomer composition | |
| CN118591593A (zh) | 可固化硅酮组合物及其经固化的产物 | |
| WO2022097510A1 (ja) | 有機ケイ素化合物及び接着助剤 | |
| TW201035174A (en) | Beta-ketoester group-containing organopolysiloxane compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 23706155 Country of ref document: EP Kind code of ref document: A1 |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 202380029413.X Country of ref document: CN |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 18850096 Country of ref document: US |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 2024558209 Country of ref document: JP |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 1020247037009 Country of ref document: KR |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 2023706155 Country of ref document: EP |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| ENP | Entry into the national phase |
Ref document number: 2023706155 Country of ref document: EP Effective date: 20241113 |
|
| WWP | Wipo information: published in national office |
Ref document number: 18850096 Country of ref document: US |