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WO2025226433A1 - Revêtement antiadhésif au silicium présentant des propriétés de barrière contre la graisse et l'eau - Google Patents

Revêtement antiadhésif au silicium présentant des propriétés de barrière contre la graisse et l'eau

Info

Publication number
WO2025226433A1
WO2025226433A1 PCT/US2025/023409 US2025023409W WO2025226433A1 WO 2025226433 A1 WO2025226433 A1 WO 2025226433A1 US 2025023409 W US2025023409 W US 2025023409W WO 2025226433 A1 WO2025226433 A1 WO 2025226433A1
Authority
WO
WIPO (PCT)
Prior art keywords
coating composition
siloxane polymer
less
alkenyl
coating
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.)
Pending
Application number
PCT/US2025/023409
Other languages
English (en)
Inventor
Pierre Chevalier
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Silicones Corp
Original Assignee
Dow Silicones Corp
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 Dow Silicones Corp filed Critical Dow Silicones Corp
Publication of WO2025226433A1 publication Critical patent/WO2025226433A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • 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
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups

Definitions

  • the present invention relates to a silicone coating composition that can be used as a coating for substrates to impart grease, water, air barrier, abrasion resistance, and release properties.
  • Bakery paper typically comprises a cellulosic substrate coated with a substance to promote release properties and water resistance.
  • silicone emulsion coated cellulosic substrates are desirable bakery paper compositions.
  • Other less desirable bakery paper compositions comprise cellulosic substrates coated with chrome complexes or fluoro-polymers.
  • health concerns with heavy metal or fluorinated coatings make these latter options less desirable than silicone coated bakery paper compositions.
  • Silicone coated bakery papers are known for their release properties and water resistance. Silicones are known for water resistance, but not grease resistance. It is desirable to obtain a bakery paper that benefits from the healthier profile of silicones coated paper, but that has grease resistance in addition to water resistance and release properties.
  • compositions that can coat a substrate to form a silicone coated bakery paper that has the following target performance characteristics: (a) low extractables as evidenced by an immediate value of less than 15%, preferably less than 14% and a post-cure value (24-hr value) of less than 10%, preferably less than 9% in the x-ray fluorescence (XRF) test described hereinbelow; (b) abrasion resistance evidenced by 90% or higher performance in the abrasion test described herein below; (c) water barrier as evidenced by less than 18 grams per square meter (g/nT) in a Cobb60 test described herein below; (d) grease barrier as evidenced by a value of 6 or higher in a 3M KIT test as described herein below; (e) release/low baking residues as evidenced by less than 11 g/nT residue in the bakery test described hereinbelow; and (f) air resistance as evidenced by a value of 10,000 seconds or higher in the Gurley test described hereinbelow
  • EVOH ethylene vinyl alcohol
  • the present invention provides a coating composition that can coat a substrate to form a silicone coated bakery paper that has the following target performance characteristics: (a) low extractables as evidenced by an immediate value of less than 15%, even less than 14% and a 24- hour value of less than 10%, even less than 9% in the x-ray fluorescence (XRF) test described hereinbelow; (b) abrasion resistance evidenced by 90%or higher performance in the abrasion test described herein below; (c) water barrier as evidenced by less than 18 grams per square meter (g/m ) in a Cobb60 test described herein below; (d) grease barrier as evidenced by a value of 6 or higher in a 3M KIT test as described herein below; (e) release/low baking residues as evidenced by less than 11 g/m residue in the bakery test described hereinbelow; and (f) air resistance as evidenced by a value of 10,000 seconds or higher in the Gurley Air Permeability Test described hereinbelow. Moreover, the present invention can achieve these
  • the present invention is a result of discovering that including an alkyl and/or alkenyl succinic anhydride-modified starch (such as octenyl succinate starch, or sodium octenyl succinate starch) into a silicone-based coating for bakery paper increases the grease resistance of the resulting coating while also achieving the other target performance characteristics and without the need for EVOH.
  • an alkyl and/or alkenyl succinic anhydride-modified starch such as octenyl succinate starch, or sodium octenyl succinate starch
  • the present invention is a coating composition
  • a coating composition comprising the following components: (a) alkenyl-functional siloxane polymer with an average of at least two silicon- bonded alkenyl groups per molecule; (b) SiH-functional siloxane polymer containing an average of at least two SiH functionalities per molecule; (c) optionally, a non-reactive siloxane polymer; (d) hydrosilylation catalyst; (e) optionally, hydrosilylation reaction inhibitor; (f) surfactant; (g) an acid/base buffer that maintains a coating composition pH of less than 7 ; (h) alkyl and/or alkenyl succinic anhydride-modified starch; (i) water; (j) optionally, biocide; and (k) optionally, antifoam; where the molar ratio of SiH from component (b) to alkenyl groups from component (a) is in a range of 1.2 to 3.0.
  • the present invention is a process for making a non-stick coating, the process comprising combining the component of the coating composition of the first aspect together to form a mixture, coating a substrate with the mixture form a coating on the substrate, and then curing the coating.
  • the present invention is an article comprising a substrate coated with the coating composition of the first aspect, where the coating composition has undergone curing by a hydrosilylation reaction between the alkenyl-functional siloxane polymer and the SiH- functional siloxane polymer.
  • the coating composition of the present invention is useful for preparing coating on food packaging materials as well as packaging for any materials that benefit from water and oil barrier properties.
  • the coating composition is useful for coating substrates to form articles suitable for use as bakery paper, French fry containers, hamburger packaging, pizza boxes, petfood bags, candle packaging, and soap packaging.
  • 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.
  • Multiple means two or more.
  • “And/or” means “and, or as an alternative”. All ranges include endpoints unless otherwise indicated. The sum of components in a composition do not exceed 100 weight-percent or volume-percent based respectively on the weight or volume of the composition.
  • the present invention is a coating composition.
  • the coating composition is desirably aqueous continuous and can be an emulsion and/or dispersion.
  • the coating composition comprises the following components: (a) alkenyl-functional siloxane polymer; (b) silylhydride (SiH)-functional siloxane polymer; (c) optionally, a non-reactive siloxane polymer; (d) hydrosilylation catalyst; (e) optionally, hydrosilylation reaction inhibitor; (f) surfactant; (g) an acid/base buffer that maintains a coating composition pH of less than 7 ; (h) alkyl and/or alkenyl succinic anhydride-modified starch; (i) water; (j) optionally, biocide; and (k) optionally, antifoam.
  • the molar ratio of SiH from the SiH-functional siloxane polymer to alkenyl groups from the alkenyl-functional siloxane polymer is in a range of 1.2-3.0.
  • the coating composition can be free of ethylene vinyl alcohol (EVOH).
  • EVOH ethylene vinyl alcohol
  • the coating composition can be free of any organic copolymer comprising at least two types of repeating units: (i) an alkyl group comprising 2 to 12 carbon atoms; and (ii) an alkyl group with 2 to 12 carbon atoms and at least one pendant alcohol.
  • the coating composition can be free of ethylene- vinyl ester copolymers.
  • the alkenyl-functional siloxane polymer preferably has at least two silicon-bonded alkenyl-functional groups per molecule.
  • the alkenyl group is preferably linear having up to 6 carbon atoms, as exemplified by hexenyl, vinyl, allyl or pentenyl, or may be cycloalkenyl such as cyclohexenyl. Vinyl groups may be desirable for cost and regulations reasons, especially for food related uses.
  • the organopolysiloxane containing alkenyl groups can contain terminal and/or pendant alkenyl groups. If the organopolysiloxane has terminal alkenyl groups it is an alkenyl-terminated polydiorganosiloxane.
  • the alkenyl-functional siloxane polymer can for example be a linear organopolysiloxane having the general formula:
  • each X denotes independently a phenyl group or an alkyl or cycloalkyl group having from 1 to 10 carbon atoms, for example, methyl, ethyl, propyl, butyl or cyclohexyl; each Y denotes an alkenyl group; subscript x typically has a value of zero or more, preferably 20 or more, 40 or more, 60 or more, 80 or more, 100 or more, even 120 or more while at the same time is typically 500 or less, and can be 250 or less, 200 or less, 150 or less, 140 or less, 130 or less, even 120 or less; subscript y typically has a value of zero or more, preferably 20 or more, 40 or more, 60 or more, 80 or more, 100 or more, even 120 or more while at the same time is typically 500 or less, and can be 250 or less, 200 or less, 150 or less,
  • the organopolysiloxane containing alkenyl groups can be a linear vinyl end-capped siloxane polymer such as a dimethylvinylsiloxy-terminated polydiorganosiloxane, or a hexenyl terminated polydiorganosiloxane, such as a dimethyl (5-hexenyl)siloxy-terminated polydiorganosiloxane.
  • at least 50% of all the X substituents of the alkenyl-functional siloxane polymer are methyl groups, most preferably all being methyl groups. It is possible but not preferred that small amounts (preferably less than 10% of all the substituents present) of other substituents are present, for example hydroxyl groups.
  • the organopolysiloxane containing alkenyl groups is free of substituents extending from the polysiloxane backbone other than hydrocarbyl groups.
  • a suitable linear organopolysiloxane containing alkenyl groups is a linear vinyl end-capped polydimethylsiloxane having an average of 120 dimethylsiloxane units, which is commercially available from Gelest under the name DMS-V22.
  • the alkenyl-functional siloxane polymer can be a branched siloxane comprising one or more Q units of the formula (SiC>4/2), from 15 to 995 D units of the formula R b 2SiO2/2 and M units of the formula R a R b 2SiOi/2.
  • the R a and R b substituents are selected from alkyl groups having 1 to 6 carbon atoms and alkenyl groups having 2 to 6 carbon atoms.
  • the R b substituents are alkyl groups, most preferably methyl groups.
  • At least two, and preferably at least three, R a substituents in such a Q-branched siloxane are alkenyl groups, as described in EP- A- 1070734.
  • Vinyl groups can be present as methylvinylsiloxane units.
  • Such a siloxane may for example be a poly(dimethylsiloxane-silicate) copolymer having at least three vinyldimethylsilyl-terminated siloxane branches.
  • the branched siloxane can also incorporate other terminal groups such as terminal trimethylsilyl (SiMe 3 ) and/or terminal hydroxy dimethylsilyl (SiMe2OH) groups.
  • the Q branched siloxane can contain other additional branching groups, for example it can also incorporate units. Branched siloxanes have the advantage that they allow faster cure than linear polymers with similar viscosities.
  • the alkenyl-functional siloxane polymer is typically present at a concentration of 2 wt% or more, 4 wt% or more, 6 wt% or more, 8 wt% or more, 9 wt% or more, even 10 wt% or more while at the same time is typically 20 wt% or less, 18 wt% or less, 16 wt% or less, 14 wt% or less, 12 wt% or less, 10 wt% or less, or even 9.5 wt% or less with wt% values based on coating composition weight.
  • the silylhydride (SiH)-functional siloxane polymer generally contains an average of at least 2 or 3 SiH groups per molecule.
  • the SiH-functional siloxane polymer can have the general formula:
  • each R l can be an alkyl group having 1 to 4 carbon atoms or hydrogen, d and e are 0 or any number such that d+e is from 8 to 400.
  • the SiH-functional siloxane polymer comprises at least two or three methylhydrogensiloxane units.
  • the SiH-functional siloxane polymer can for example be a poly(methylhydrogensiloxane) having trimethylsilyl terminal units or a dimethylsiloxane methylhydrogensiloxane copolymer having trimethylsilyl terminal units.
  • the crosslinking agent can alternatively contain SiH groups in a linked cyclic polyorganosiloxane structure.
  • Such linked cyclic polyorganosiloxanes can be produced by reacting a cyclic polysiloxane containing at least two SiH groups with a compound having aliphatic unsaturation or containing a hydroxy group, for example a silane or polyorganosiloxane having aliphatic unsaturation or containing a hydroxy group as described in US7378482.
  • the SiH-functional siloxane polymer can be an MQ resin consisting of units of the general formula SiC>4/2 and R q 3SiOi/2 wherein at least three R q substituents in the MQ resin molecule are hydrogen atoms and the remainder are alkyl groups, or may be a rake or comb polymer comprising a polydiorganosiloxane chain containing one or more T or Q unit having a subchain of diorganosiloxane and organohydrogensiloxane units attached thereto.
  • the SiH-functional siloxane polymer has a viscosity of from 5 to 1000 mm 2 /s at 25° C, more preferably 20 to 350 mm /s, most preferably 50 to 300 mnr/s.
  • the SiH-functional siloxane polymer is preferably present in an amount such that the molar ratio of the total number of H groups in the coating composition to alkenyl groups in the coating composition is from 0.9: 1 to 8:1, preferably 1.1:1 to 4:1, more preferably 1.2: 1 to 3.0: 1, and most preferably 1.5:1 to 3: 1.
  • the SiH-functional siloxane polymer is typically present at a concentration of 0. 1 wt% or more, 0.2 wt% or more, 0.3 wt% or more, 0.4 wt% or more, 0.5 wt% or more, 0.6 wt% or more, 0.7 wt% or more, 0.8 wt% or more, 0.9 wt% or more, even 1.0 wt% or more while at the same time is typically 4.0 wt% or less, 3.0 wt% or less, 2.0 wt% or less, 1.0 wt% or less, 0.8 wt% or less, 0.6 wt% or less, or even 0.5 wt% or less, with wt% values based on coating composition weight.
  • the non-reactive siloxane polymer is an optional component. It can be desirable to include the non-reactive siloxane polymer to, for example, serve as a surface lubricating agent useful in industrial processes where friction and shear apply. It can also be desirable to minimize or avoid use of non-reactive siloxane polymers because they can be extractable components from resulting cured coating, which can be undesirable particularly in food applications.
  • the non-reactive siloxane polymer is free of reactive groups such as SiH groups, alkenyl groups, and hydroxyl groups. Typically, the non-reactive siloxane polymer has only hydrocarbyl groups bound the silicon atoms of the siloxane polymer.
  • Typical non-reactive siloxane polymer for use in the present invention are linear trimethyl end-blocked polydimethylsiloxanes.
  • the non-reactive siloxane polymer can have the following average structure:
  • DOWSILTM 200 fluid products are examples of suitable linear trimethyl end-blocked poly dimethylsiloxanes.
  • a suitable linear trimethyl end- blocked polydimethylsiloxane has an average viscosity of 12,500 mm 2 /s and is available under the name DOWSILTM 200 Fluid 12,500 cSt from The Dow Chemical Company (DOWSIL is a trademark of The Dow Chemical Company).
  • the concentration of non-reactive siloxane polymer in the coating composition is typically zero wt% or more and can be 0.2 wt% or more, 0.3 wt% or more, 0.4 wt% or more, even 0.5 wt% or more, while at the same time is typically 5 wt% or less, and can be 4 wt% or less, 3 wt% or less, 2 wt% or less, one wt% or less, 0.8 wt% or less, 0.6 wt% or less, or even 0.5 wt% or less, with wt% values based on coating composition weight.
  • the hydrosilylation catalyst preferably comprises a platinum group metal that is a group VIII metal such as platinum, ruthenium, rhodium, palladium, osmium or indium.
  • Suitable hydrosilylation catalysts include complexes or compounds of these platinum group metals, particularly platinum compounds or complexes including chloroplatinic acid, either in hexahydrate form or anhydrous form, and or a platinum-containing catalyst which is obtained by a method comprising reacting chloroplatinic acid with an aliphatically unsaturated organosilicon compound such as divinyltetramethyldisiloxane, platinum acetylacetonate, complexes of platinous halides with unsaturated compounds, for example, ethylene, propylene, organovinylsiloxanes and styrene, hexamethyldiplatinum, alkene-platinum-silyl complexes such as (COD)Pt(SiMeC12)2, where COD
  • Platinum-based hydrosilylation catalysts include compounds and complexes such as platinum (0)-l,3-divinyl-l,l,3,3-tetramethyldisiloxane (Karstedt’s catalyst), I LPtCL,, di-p.- carbonyl di-.7i.-cyclopentadienyldinickel, platinum-carbonyl complexes, platinum- divinyltetramethyldisiloxane complexes, platinum cyclovinylmethylsiloxane complexes, platinum acetylacetonate (acac), 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 hydrosilylation catalyst can be part of a solution that includes complexes of platinum with low molecular weight organopolysiloxanes that include 1,3-diethenyl-l, 1,3,3- tetramethyldisiloxane complexes with platinum. These complexes may be microencapsulated in a resin matrix.
  • the catalyst can be 1,3-diethenyl- 1,1,3, 3 -tetramethyldisiloxane complex with platinum.
  • the concentration of hydrosilylation catalyst is desirably sufficient to increase the reaction rate of a hydrosilylation reaction between the alkenyl-functional siloxane polymer and the SiH-functional siloxane polymer.
  • concentration of actual catalyst compound will vary depending on what catalyst compound is in the coating composition.
  • the concentration of the catalyst composition is typically 0.01 wt% or more, 0.02 wt% or more, 0.03 wt% or more, 0.04 wt% or more, 0.05 wt% or more, 0.06 wt% or more, 0.07 wt% or more, 0.08 wt% or more, 0.09 wt% or more, even 0.10 wt% or more, while at the same time is typically 0.50 wt% or less, 0.40 wt% or less, 0.30 wt% or less, 0.20 wt% or less, or even 0.10 wt% or less, with wt% values based on coating composition weight.
  • Hydrosilylation inhibitor can be used for altering when and/or how fast the hydrosilylation reaction occurs.
  • Hydrosilylation inhibitor can be, for example, one or more than one material selected from a group consisting of an acetylenic alcohol, an acetylenic alcohol, an ene-yne compound, a triazole, a phosphine, a mercaptan, a hydrazine, an amine, a fumarate, a maleate, an ether, carbon monoxide, an alkenyl -functional siloxane oligomer, and a combination of two or more thereof.
  • Acetylenic alcohols are exemplified by 3,5-dimethyl-l-hexyn-3-ol, l-butyn-3-ol, 1- propyn-3-ol, 2-methyl-3-butyn-2-ol, 3-methyl-l-butyn-3-ol, 3 -methyl- l-pentyn-3-ol, 3-phenyl- l-butyn-3-ol, 4-ethyl-l-octyn-3-ol, 3,5-dimethyl-l-hexyn-3-ol, and 1-ethynyl-l -cyclohexanol, and a combination thereof.
  • the acetylenic alcohol can be a silylated acetylenic compound. Without wishing to be bound by theory, it is thought that adding a silylated acetylenic compound reduces yellowing of the reaction product prepared from hydrosilylation reaction as compared to a reaction product from hydrosilylation of starting materials that do not include a silylated acetylenic compound or that include an organic acetylenic alcohol inhibitor, such as those described above.
  • Silylated acetylenic compounds are exemplified by (3 -methyl- l-butyn-3- oxy)trimethylsilane, ((1 ,l-dimethyl-2-propynyl)oxy)trimethylsilane, bis(3-methyl-l-butyn-3- oxy)dimethylsilane, bis(3-methyl-l-butyn-3-oxy)silanemethylvinylsilane, bis((l,l-dimethyl-2- propynyl)oxy)dimethylsilane, methyl(tris(l,l-dimethyl-2-propynyloxy))silane, methyl(tris(3- methyl-l-butyn-3-oxy))silane, (3-methyl-l-butyn-3-oxy)dimethylphenylsilane, (3-methyl-l- butyn-3-oxy)dimethylhexenylsilane, (3-methyl-l-butyn-3-oxy
  • silylated acetylenic compound useful as the inhibitor herein may be prepared by methods known in the art, for example, U.S. Patent 6,677,407 to Bilgrien, et al. discloses silylating an acetylenic alcohol described above by reacting it with a chlorosilane in the presence of an acid receptor.
  • Ene-yne compound include 3-methyl-3-penten-l-yne; 3,5-dimethyl-3-hexen-l-yne; and a combinations thereof.
  • Triazole include benzotriazole.
  • Amines are exemplified by tetramethyl ethylenediamine, 3-dimethylamino-l-propyne, n- methylpropargylamine, propargylamine, 1-ethynylcyclohexylamine, or a combination thereof.
  • Fumarates include dialkyl fumarates such as diethyl fumarate, dialkenyl fumarates such as diallyl fumarate, dialkoxyalkyl fumarates such as bis-(methoxymethyl)ethyl fumarate.
  • Maleates include dialkyl maleates such as diethyl maleate, dialkenyl maleates such as diallyl maleate, and dialkoxyalkyl maleates such as bis-(methoxymethyl)ethyl maleate.
  • the inhibitor may comprise an alkenyl-functional siloxane oligomer, which may be cyclic or linear such as methylvinylcyclosiloxanes exemplified by 1,3, 5, 7-tetramethyl-l, 3, 5, 7- tetravinylcyclotetrasiloxane, 1,3, 5, 7-tetramethyl-l, 3, 5, 7-tetrahexenylcyclotetrasiloxane, 1,3- divinyl-l,3-diphenyl-l,3-dimethyldisiloxane; l,3-divinyl-l,l,3,3-tetramethyldisiloxane; and a combination of two or more thereof.
  • an alkenyl-functional siloxane oligomer which may be cyclic or linear such as methylvinylcyclosiloxanes exemplified by 1,3, 5, 7-tetramethyl-l, 3, 5, 7- tetravinylcyclot
  • the concentration of hydrosilylation reaction inhibitor in the coating composition is typically zero wt% or more, 0.01 wt% or more, 0.02 wt% or more, 0.03 wt% or more, even 0.04 wt% or more, while at the same time is typically 0.08 wt% or less, 0.07 wt% or less, 0.06 wt% or less, 0.05 wt% or less, or even 0.04 wt% or less, with wt% values based on coating composition weight.
  • Surfactants are useful for stabilizing the components of the present invention as an emulsion and/or dispersion in a water-continuous phase.
  • the surfactant can be nonionic and/or ionic.
  • the surfactant is nonionic.
  • Suitable surfactants can be selected from those that are known and the art and are commercially available.
  • Suitable nonionic surfactants include alkylphenols, fatty alcohols or fatty acids with alkylene oxide groups, such as ethylene oxide or propylene oxide groups.
  • Suitable ionic surfactants include anionic surfactants such as sulfates, sulfonates, phosphates, and sulfosuccinates.
  • Suitable surfactants for use herein are exemplified by those described as surfactant (G) in U.S. Patent Application Publication 2007/0099007 at paragraphs [0167] to [0176].
  • polyvinyl alcohol can be a primary surfactant and a poly(oxy- 1 ,2-ethanediyl) can be a co-surfactant.
  • surfactants for use in the present invention include those available under the names PVA 40 TAD from BIM Kemi AB and LUTENSOL TM XP100 (LUTENSOL is a trademark of BASF SE).
  • the concentration of surfactants in the coating composition is typically greater than zero, preferably 0.5 wt% or more, 1.0 wt% or more, 2.0 wt% or more, 3.0 wt% or more, 3.5 wt% or more, 4.0 wt% or more, 5.0 wt% or more, 6.0 wt% or more, even 7.0 wt% or more, while at the same time is typically 10.0 wt% or less, 9.0 wt% or less, 8.0 wt% or less, 7.0 wt% or less, 6.0 wt% or less, 5.0 wt% or less, even 4.0 wt% or less, with wt% values based on coating composition weight.
  • the coating composition of the present invention includes an acid/base buffer, which is a combination of acid and a base compounds that serves as a buffer to maintain the coating composition at a pH of less than 7.
  • the acid/base buffer can be any acid/base buffer.
  • the acid/base buffer typically comprises a mono or polyprotic acid and its conjugate base.
  • a suitable buffer comprises HCOf/COs 2 ’ and H2PO4 /HPO4 2 ’ as described as agent F in U.S. Patent Application Publication 2007/0099007 at paragraphs [00145] to [00147] may be used herein.
  • the buffer can comprise NaCOr and NaHCCh.
  • the buffer can comprise citric acid and a citrate salt such as potassium citrate or sodium citrate.
  • the acid/base buffer can be formed by combining a polyprotic acid (such as citric acid) with a base (such as sodium hydroxide) at a molar ratio such that fewer than all of the polyprotic acid is neutralized.
  • a polyprotic acid such as citric acid
  • a base such as sodium hydroxide
  • One of ordinary skill can choose appropriate relative concentrations of selected acids and bases as well as the required amount of total buffer necessary to achieve a buffer that maintains a pH of less than 7 for a given coating composition.
  • the buffer maintains the coating composition at a pH of 7 or less, but it can maintain it at a pH of 6 or less, while at the same time the buffer desirably maintains the coating composition at a pH of one or more, 2 or more, even 3 or more, or 4 or more.
  • the amount of the acid/base buffer is typically greater than 0 wt%, alternatively 0.02 wt% or more, 0.03 wt% or more, 0.04 wt% or more, 0.05 wt% or more, 0.06 wt% or more, 0.07 wt% or more, 0.08 wt% or more, 0.1 wt% or more, 0.2 wt% or more, 0.3 wt% or more, 0.4 wt% or more, even 0.5 wt% or more, and at the same time is typically 2.0 wt% or less, 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, 0.5 wt% or less, 0.4 wt% or less, 0.3 wt% or less, 0.2 wt% or less less
  • the alkyl and/or alkenyl succinic anhydride-modified starch is a starch compound that has been modified with an alkyl and/or alkenyl succinic anhydride compound. “Modified” means that the starch compound has undergone esterification reactions with alkyl and/or alkenyl succinic anhydride compounds.
  • esterification or “modification”
  • the extent of esterification (or “modification”) of the starch is presumably not critical as long as it is modified. It is possible to characterize the extent of modification by designating a degree of substitution using a nuclear magnetic resonance (NMR) method such as that taught in the article: M.C.
  • NMR nuclear magnetic resonance
  • the degree of substitution (DS) for the alkyl and/or alkenyl succinic anhydride-modified starch of the present invention is desirably greater than zero, preferably 0.01 or more, more preferably 0. 1 or more, 0.12 or more, even 0.18 or more, while at the same time can be 2.5 or less, 2 or less, one or less, 0.80 or less, 0.60 or less, 0.40 or less, 0.20 or less, even 0.18 or less.
  • DS refers to the average number of alkyl and/or alkenyl succinic anhydride groups per glucose unit in the alkyl and/or alkenyl succinic anhydride modified starch material.
  • starch In the broadest scope of the present invention, the type of starch is not critical.
  • the starch comprises 50% or more, 60% or more, 80% or more, 90% or more, even 95% or more amylopectin content.
  • Amylopectin content can be classically determined by one of ordinary skill in the art by way of potentiometric analysis of iodine absorbed by amylose to form a complex.
  • the starch is maize starch.
  • the starch can be a waxy starch, such as waxy maize starch.
  • the alkyl and/or alkenyl succinic anhydride is one or more than one compound having the following chemical structure: where there can be one R s or two groups bound to carbons of the succinic anhydride that are not directly bound to oxygen, and each R s is independently selected from alkyl and alkenyl groups.
  • the alkyl and/or alkenyl succinic anhydride compound contain one such R s group per molecule.
  • the alkyl and alkenyl groups are selected from those having 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, 9 or more, 10 or more, 11 or more, 12 or more, 13 or more, 14 or more, 15 or more, 16 or more, 17 or more, 18 or more, even 19 or more carbon atoms while at the same time typically containing 20 or fewer, 19 of fewer, 18 or fewer, 17 or fewer, 16 or fewer, 15 or fewer, 14 or fewer, 13 or fewer, 12 or fewer, 11 or fewer, 10 or fewer, 9 or fewer, 8 or fewer, 7 or fewer, 6 or fewer, 5 or fewer, even 4 or fewer carbon atoms.
  • R s groups examples include allyl, octenyl groups, octyl groups, dodecyl groups, dodecenyl groups, hexadecenyl groups, and 2-methyl-2-propenyl groups.
  • the alkyl and/or alkenyl succinic anhydride is desirably octenyl succinic anhydride (OSA).
  • the most preferred alkyl and/or alkenyl succinic anhydride compound is OSA-modified starch, preferably OSA-modified maize starch, more preferably OSA-modified waxy maize starch, even more preferably what is called an acid and sodium OSA treated waxy maize starch.
  • OSA-modified maize starch preferably OSA-modified maize starch, more preferably OSA-modified waxy maize starch, even more preferably what is called an acid and sodium OSA treated waxy maize starch.
  • One desirable acid and sodium OSA treated waxy maize starch is commercially available under the name STABILYSTM BA25 from Roquette, which has a DS of 0.022 corresponding to having an average of 0.022 OSA units bound to the OSA-modified maize starch per glucose unit in the OSA-modified maize starch.
  • STABILYSTM BA25 from Roquette
  • Other suitable acid and sodium OSA treated waxy maize starch materials are similar but
  • the concentration of the alkyl and/or alkenyl succinic anhydride modified starch in the coating composition is typically one wt% or more, and can be 2 wt% or more, 3 wt% or more, 4 wt% or more, 5 wt% or more, 6 wt% or more, 7 wt% or more, 8 wt% or more, 9 wt% or more, 10 wt% or more, 1 1 wt% or more, 12 wt% or more, 1 wt% or more, 14 wt% or more, even 15 wt% or more, while at the same time is typically 25 wt% or less, 20 wt% or less, 18 wt% or less, 16 wt% or less, 14 wt% or less, even 12 wt% or less, with wt% values based on coating composition weight.
  • Water serves as a continuous phase in the coating composition of the present invention.
  • the water is not generally limited, and may be utilized neat (that is, absent any carrier vehicles/solvents), and/or pure (that is, free from or substantially free from minerals and/or other impurities).
  • the water may be processed or unprocessed before use in the process described above. Examples of processes that may be used for purifying the water include distilling, filtering, deionizing, and combinations of two or more thereof, such that the water may be deionized, distilled, and/or filtered.
  • the water may be unprocessed (e.g. may be tap water provided by a municipal water system or well water, used without further purification).
  • the water may be purified before use in the process.
  • the concentration of water in the coating composition is typically 20 wt% or more, 30 wt% or more, 40 wt% or more, and can be 50 wt% or more, 60 wt% or more, 70 wt% or more, even 80 wt% or more, while at the same time is typically 95 wt% or less, 90 wt% or less, 85 wt% or less, 82 wt% or less, 80 wt% or less, even 75 wt% or less, with wt% values based on coating composition weight.
  • Biocide is desirable in the present coating composition to inhibit growth of undesirable organisms in the coating composition. It is particularly desirable considering the presence of the alkyl and/or alkenyl succinic anhydride-modified starch component.
  • the coating composition can contain multiple biocides as the biocide component.
  • Suitable biocides include any biocides known in the art.
  • the biocide can be a fungicide, an herbicide, a pesticide, an antimicrobial agent, or a combination of two or more thereof.
  • Exemplary biocides are disclosed, for example, in U.S. Patent 9,221,041.
  • Specific examples of suitable biocides for use in the present invention include those available under the names KATHONTM LXE (KATHON is a trademark of Nutrition & Biosciences USA2, LLC) and BIOBANTM 1530 (BIOBAN is a trademark of Lanxess Corporation).
  • the concentration of biocide in the coating composition is typically zero wt% or more and can be 0.005 wt% or more, 0.01 wt% or more, 0.02 wt% or more, 0.03 wt% or more, 0.04 wt% or more, 0.05 wt% or more, while at the same time is typically 0.30 wt% or less, 0.20 wt% or less, 0.10 wt% or less, 0.08 wt% or less, 0.06 wt% or less, or even 0.04 wt% or less, with wt% values based on coating composition weight.
  • Antifoam components can be desirable in the present coating composition to prevent undesirable frothing of the coating composition during formulating and use.
  • anti-foaming components examples include emulsions containing silica and polydimethylsiloxanes.
  • suitable anti-foaming components include those available under the tradenames DOWSILTM 7989, SYL-OFFTM EM 25 7989 ANTIFOAM, XIAMETERTM AFE-0100, XIAMETERTM AFE-1510, XIAMETERTM AFE-1520, and XIAMETERTM AFE-1530.
  • DOWSIL is a trademark of The Dow Chemical Company.
  • XIAMETER and SYL-OFF are trademarks of Dow Silicones Corporation.
  • the concentration of antifoam in the coating composition is typically zero wt% or more, and can be 0.01 wt% or more, 0.02 wt% or more, 0.03 wt% or more, 0.04 wt% or more, 0.05 wt% or more, 0.06 wt% or more, even 0.07 wt% or more, while at the same time is typically 0.20 wt% or less, and can be 0.10 wt% or less, 0.08 wt% or less, 0.06 wt% or less, even 0.05 wt% or less, with wt% values based on coating composition weight.
  • the coating composition of the present invention desirably comprises: (a) a water at a concentration in a range of 20 to 95 weight-percent (wt%); (b) a concentration of siloxane polymer components (components (a), (b) and (c)) that is in a range of 2 to 20 wt%, and that is preferably 2 wt% or more, 4 wt% or more, 8 wt% or more, even 9 wt% or more, while at the same time is 20 wt% or less, 18 wt% or less, 16 wt% or less, 14 wt% or less, 12 wt% or less, or even 10 wt% or less; and (c) a concentration of alkyl and/or alkenyl succinic anhydride-modified starch that is in a range of 0.45 to 18 wt%, and that is preferably 0.45 wt% or more, 0.50 wt% or more, 1.0 wt% or more
  • the coating composition of the present invention can consist of a single mixture of all of the components together as a single emulsion or dispersion.
  • the coating composition can comprise multiple mixtures each containing a selection of the components. Multiple mixtures can be desirable to, for instance, separate the catalyst from reactants so that the coating composition remains stable until such time as it is ready to be used when the mixtures can be combined into a single mixture.
  • the composition comprises at least two separate parts that remain distinct from one another until blended to form a single coating composition.
  • One of the two parts comprises: (i) water; (ii) surfactant; (iii) alkenyl-functional siloxane polymer; (iv) SiH-functional siloxane polymer; and (v) optionally, non-reactive siloxane polymer.
  • Another of the two parts comprises: (i) water; (ii) surfactant; and at least one component selected from (iii) alkenyl- functional siloxane polymer; (iv) SiH-functional siloxane polymer; and (v) non-reactive siloxane polymer.
  • the anhydride-modified starch can be a separate part, or can be included in one of the other parts.
  • the hydrosilylation catalyst is either maintained as a separate third part or combined into the second part as long as the second part does not contain both alkenyl-functional siloxane polymer and SiH-functional siloxane polymer.
  • hydrosilylation catalyst is included in the second part, it is desirable for the second part to also contain the hydrosilylation reaction inhibitor.
  • the remaining components can be in either one or both of the first or second part, or can be one or more additional separate part.
  • the antifoam component when present can desirably be an antifoam emulsion and can be its own part or combined with one of the other parts.
  • the present invention is a process for making a non-stick coating
  • the process comprises combining the component of the coating composition of the first aspect of the present invention together to form a mixture, coating a substrate with the mixture to form a coating on the substrate, and then curing the coating.
  • the process also includes drying the coating after it is on the substrate and before, during or after curing it.
  • Curing involves hydrosilylation reaction between the alkenyl-functional siloxane polymer and the SiH-functional siloxane polymer.
  • curing and drying occur at the same time by exposing the coating on the substrate to a temperature in a range of 110 to 180 degrees Celsius (°C).
  • the process can comprise providing the coating composition of the first aspect as multiple parts and then combining them together to form the mixture used to coat a substrate.
  • the present invention is an article comprising a substrate coated with the coating composition of the first aspect , where the coating composition has undergone curing by hydrosilylation between the alkenyl- functional siloxane polymer and the SiH-functional polymer.
  • the article can be made according to the process of the second aspect.
  • Table 1 identifies the components for use in making the samples that follow. “Me” refers to a methyl group. “Vi” refers to a vinyl group.
  • SYL-OFF is a trademark of Dow Silicones Corporation.
  • DOWSIL is a trademark of The Dow Chemical Company.
  • XIAMETER is a trademark of Dow Corning Corporation.
  • SURFYNOL is a trademark of Evonik Operation s GMBH.
  • LUTENSOL is a trademark of BASF SE.
  • KATHON is a trademark of Nutrition & Biosciences USA 2, LLC.
  • BIOBAN is a trademark of Lanxess Corporation.
  • STABILYS is a trademark of Roquette.
  • Table 2 provides the composition of the Base Emulsion, with amounts for the components listed in wt% relative to the Base Emulsion weight.
  • aqueous acid/base buffer solution by blending the water, Buffer Acid G, and Base G components together. Weigh out separately the Vinyl Siloxane A, SiH Siloxane B, and Non-reactive siloxane C and then mix them together to form a polymer mix. Weigh out separately the surfactants and mix them together to form a polymer mix. Slowly add the surfactant mix to the polymer mix while emulsifying using a high pressure sonolator at 100 bars until obtaining a Dv0.9 particle size between 1.0 and 2.5 micrometers, preferably between 1.5 and 2.0 micrometers. Determine DV0.9 particle size using laser diffraction spectroscopy with a Malvern Mastersizer 3000 instrument. To the emulsion add the buffer solution, inhibitors and biocides while continuing to emulsify. The resulting emulsion is the Base Emulsion.
  • Table 3 provides the composition of the Catalyst Emulsion, with amounts for the components listed in wt% relative to the Catalyst Emulsion weight. Table 3.
  • aqueous acid/base buffer solution by blending the water, Buffer Acid G, and Base G components together. Weigh out separately the Vinyl Siloxane A and Catalyst D, and then mix them together to form a polymer mix. Weigh out separately the surfactants and mix them together to form a polymer mix. Slowly add the surfactant mix to the polymer mix while emulsifying using a high pressure sonolator at 100 bars until obtaining a Dv0.9 particle size between 1.0 and 2.5 micrometers, preferably between 1.5 and 2.0 micrometers. Determine DV0.9 particle size using laser diffraction spectroscopy with a Malvern Mastersizer 3000 instrument. To the emulsion add the buffer solution and biocides while continuing to emulsify. The resulting emulsion is the Catalyst Emulsion.
  • Modified Starch Solution A which contains 20 wt% Modified Starch H.
  • Modified Starch Solution B which contains 5 wt% Modified Starch H2
  • Modified Starch Solution C which contains 5 wt% Modified Starch H3;
  • XRF X-Ray fluorescence
  • MIBK methyl isobutyl ketone
  • TAPPI Cobb Test Determine the water resistance of samples using the conventional Cobb test for absorption described in TAPPI 441 om-04 test method (TAPPI Cobb Test). Expose coated substrate samples to water for 45 seconds, then remove from the water over 15 seconds and then measure the mass of water absorbed after the full 60 seconds (mass after water absorption - mass before water absorption).
  • the Cobb60 value is the mass of water absorbed after 60 seconds divided by the area of the sample in square meters and is reported in units of grams water per square meter of sample (g/m ). For the present invention it is desirable to have a Cobb60 value that is less than 18 g/m 2 .
  • CE1 presents a base curable coating composition without any starch. It fails to meet coating performance targets for 3M KIT and Gurley.
  • CE2 presents the base curable coating composition with OSA but no starch. It fails to meet coating performance targets for 3M KIT, Gurley, and Baking Residue.
  • CE3 presents a non-curable coating of just water and starch. It fails to meet coating performance targets for COBB60, 3M KIT and Baking Residue.
  • CE4 presents CE3 with OSA. It fails to meet coating performance targets for COBB60, 3M KIT and Baking Residue.
  • CE5 presents a non-curable coating of just water and an alkenyl succinic anhydride- modified starch. It fails to meet coating performance targets for COBB60, 3M KIT, Gurley, and Baking Residue.
  • CE6 presents the base curable coating composition with non-modified starch. It fails to meet coating performance targets for 3M KIT.
  • CE7 presents CE6 with twice as much non-modified starch. It fails to meet coating performance targets for abrasion resistance and 3M KIT.
  • CE8 presents CE6 with three times as much non-modified starch. It fails to meet coating performance targets abrasion resistance and baking residue.
  • CE9 presents CE8 with OSA included with non- modified starch, but not bound to the non-modified starch as a modifier. It fails to meet coating performance targets for abrasion resistance.
  • CE10 presents a sample similar to CE1 except with a lower coat-weight. It fails to meet 3M KITT and Gurley performance targets.
  • CE1 1 , CE 12, and CE13 present formulations of the various modified starch components at increasing DS values but without including a silicone base.
  • the samples show that the starch coatings fail to meet the performance targets for Cobb60, 3M Kitt, Gurley, and Baking Residue.
  • Ex 1 , Ex 2 and Ex 3 present three compositions of the base curable coating composition, but with three levels of an alkenyl succinic anhydride-modified starch included. Each of those coating compositions meet all of the coating performance targets.
  • Ex 4, Ex 5, Ex 6, Ex 7, and Ex 8 present compositions of the present invention that contain alkenyl succinic anhydride-modified starch with different degrees of substitution (DS) values. Each of those coating compositions meet all of the coating performance targets.

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Abstract

L'invention concerne une composition de revêtement qui contient les composants suivants : (a) un polymère de siloxane à fonction alcényle comportant en moyenne au moins deux groupes alcényle liés au silicium par molécule ; (b) un polymère de siloxane à fonction SiH contenant en moyenne au moins deux groupes SiH par molécule ; (c) facultativement, un polymère de siloxane non réactif ; (d) un catalyseur d'hydrosilylation ; (e) facultativement, un inhibiteur de réaction d'hydrosilylation ; (f) un tensioactif ; (g) un tampon acido-basique qui maintient le pH de la composition de revêtement au-dessous de 7 ; (h) un amidon modifié par un anhydride alkyl- et/ou alcényl-succinique ; (i) de l'eau ; (j) facultativement, un biocide ; et (k) facultativement, un agent antimousse ; le rapport molaire de SiH du composant (b) aux groupes alcényle du composant (a) étant compris entre 1,2 et 3,0.
PCT/US2025/023409 2024-04-23 2025-04-07 Revêtement antiadhésif au silicium présentant des propriétés de barrière contre la graisse et l'eau Pending WO2025226433A1 (fr)

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Citations (9)

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Publication number Priority date Publication date Assignee Title
EP1070734A2 (fr) 1999-07-23 2001-01-24 Dow Corning Corporation Compositions de revêtement de silicone anti-adhésives
US6677407B1 (en) 1996-08-28 2004-01-13 Dow Corning Corporation Coating with organopolysiloxane, organohydrogensilicon, platinum catalyst and silylated acetylenic compound
US20070099007A1 (en) 2000-02-15 2007-05-03 Jean-Paul Benayoun Use of hydrophilic (co) polymers in crosslinkable aqueous silicone emulsions
US7378482B2 (en) 2002-05-01 2008-05-27 Dow Corning Corporation Compositions having improved bath life
US9221041B2 (en) 2011-09-20 2015-12-29 Dow Corning Corporation Iridium containing hydrosilylation catalysts and compositions containing the catalysts
US9714345B2 (en) * 2010-12-13 2017-07-25 Bluestar Silicones France Sas Silicone elastomer material suitable for use in particular for making dental impressions
US10053543B2 (en) * 2013-12-17 2018-08-21 Wacker Chemie Ag Polyorganosiloxane gels having glycoside groups
US10723891B2 (en) * 2016-04-25 2020-07-28 Dow Silicones Corporation Aqueous coating composition
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Publication number Priority date Publication date Assignee Title
US6677407B1 (en) 1996-08-28 2004-01-13 Dow Corning Corporation Coating with organopolysiloxane, organohydrogensilicon, platinum catalyst and silylated acetylenic compound
EP1070734A2 (fr) 1999-07-23 2001-01-24 Dow Corning Corporation Compositions de revêtement de silicone anti-adhésives
US20070099007A1 (en) 2000-02-15 2007-05-03 Jean-Paul Benayoun Use of hydrophilic (co) polymers in crosslinkable aqueous silicone emulsions
US7378482B2 (en) 2002-05-01 2008-05-27 Dow Corning Corporation Compositions having improved bath life
US9714345B2 (en) * 2010-12-13 2017-07-25 Bluestar Silicones France Sas Silicone elastomer material suitable for use in particular for making dental impressions
US9221041B2 (en) 2011-09-20 2015-12-29 Dow Corning Corporation Iridium containing hydrosilylation catalysts and compositions containing the catalysts
US10053543B2 (en) * 2013-12-17 2018-08-21 Wacker Chemie Ag Polyorganosiloxane gels having glycoside groups
US10723891B2 (en) * 2016-04-25 2020-07-28 Dow Silicones Corporation Aqueous coating composition
WO2023051954A1 (fr) * 2021-09-29 2023-04-06 Roquette Freres Revetement barriere flexible resistant au rainurage et au pliage a base d'amidon fluidifie et de polyol

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