WO2009120424A1 - Procédé de réduction de dépôt de poussières et de salissures - Google Patents

Procédé de réduction de dépôt de poussières et de salissures Download PDF

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Publication number
WO2009120424A1
WO2009120424A1 PCT/US2009/034201 US2009034201W WO2009120424A1 WO 2009120424 A1 WO2009120424 A1 WO 2009120424A1 US 2009034201 W US2009034201 W US 2009034201W WO 2009120424 A1 WO2009120424 A1 WO 2009120424A1
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WO
WIPO (PCT)
Prior art keywords
component
parts
groups
resin
mole
Prior art date
Application number
PCT/US2009/034201
Other languages
English (en)
Inventor
Stephanie Gathman
Randall Gene Schmidt
Original Assignee
Dow Corning Corporation
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 Corning Corporation filed Critical Dow Corning Corporation
Publication of WO2009120424A1 publication Critical patent/WO2009120424A1/fr

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Classifications

    • 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
    • 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
    • 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
    • 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
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing 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
    • C08G77/70—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 a method of reducing dust and dirt settlement on surfaces by treating such surfaces with a mixture of a MQ resin, a volatile solvent, and optionally a propyl silsesquioxane resin to add flexibility as needed.
  • the inventors have discovered that staining of a surface by dirt and dust settlement, particularly by dust originating from brake pads, can be reduced by treating the affected surface with a MQ resin. They have also discovered that use of a propyl silsesquioxane resin adds flexibility to the coating without sacrificing clarity or dust/dirt settlement.
  • This invention is a method of reducing dust and dirt settlement comprising treating a surface with a composition comprising
  • A) 10 parts by weight of a MQ resin comprising at least 80 mole % of siloxy units selected from (R ⁇ SiO ⁇ a and (SiO 4/2 ) b units, where each R 1 is independently an alkyl group having from 1 to 8 carbon atoms, an aryl group, a carbinol group, or an amino group, with the proviso that at least 95 mole % of the R 1 groups are alkyl groups, a and b each has a value greater than zero, and the ratio of a/b is 0.5:1 to 1.1:1;
  • Component A) is a MQ resin comprising at least 80 mole% of siloxy units selected from (R ⁇ SiO ⁇ a and (SiO 4/2 ) b units, where R 1 is an alkyl group having from 1 to 8 carbon atoms, an aryl group, a carbinol group, or an amino group, with the proviso that at least 95 mole % of the R 1 groups are alkyl groups, a and b each has a value greater than zero, and the ratio of a/b is 0.5:1 to 1.5:1.
  • the R 1 units of the MQ resin are each independently an alkyl group having from 1 to 8 carbon atoms, an aryl group, a carbinol group, or an amino group.
  • the alkyl groups are illustrated by methyl, ethyl, propyl, butyl, pentyl, hexyl, and octyl.
  • aryl groups are illustrated by phenyl, naphthyl, benzyl, tolyl, xylyl, xenyl, methylphenyl, 2-phenylethyl, 2- phenyl-2-methylethyl, chlorophenyl, bromophenyl and fluorophenyl with the aryl group typically being phenyl.
  • a "carbinol group” is defined as any group containing at least one carbon-bonded hydroxyl (COH) radical.
  • the carbinol groups may contain more than one COH radical such as for example
  • the carbinol group if free of aryl groups has at least 3 carbon atoms, or an aryl- containing carbinol group having at least 6 carbon atoms.
  • the carbinol group free of aryl groups having at least 3 carbon atoms is illustrated by groups having the formula R ⁇ OH wherein R ⁇ is a divalent hydrocarbon radical having at least 3 carbon atoms or divalent hydrocarbonoxy radical having at least 3 carbon atoms.
  • the group R ⁇ is illustrated by alkylene radicals such as -(CH2) X - where x has a value of 3 to 10, -CH 2 CH(CH 3 )-, -CH 2 CH(CH 3 )CH 2 -, -CH 2 CH 2 CH(CH 2 CH 3 )CH 2 CH 2 CH 2 -, and -OCH(CH 3 )(CH 2 ) y - wherein y has a value of 1 tolO.
  • the aryl-containing carbinol group having at least 6 carbon atoms is illustrated by groups having the formula R ⁇ OH wherein R ⁇ is an arylene radical such as -(CH 2 ) Z C 6 H 4 - wherein z has a value of 0 to 10, -CH 2 CH(CH 3 )(CH 2 ) Z C 6 H 4 - wherein z has a value of 0 to 10, -(CH 2 ) w CgH4(CH 2 ) w - wherein w has a value of 1 to 10.
  • the aryl- containing carbinol groups typically have from 6 to 14 carbon atoms.
  • the amino group is illustrated by groups having the formula -R ⁇ NH 2 or -R"NHR ⁇ NH2 wherein R" is a divalent hydrocarbon radical having at least 2 carbon atoms and R ⁇ is a divalent hydrocarbon radical having at least 2 carbon atoms.
  • the group R ⁇ is typically an alkylene radical having from 2 to 20 carbon atoms.
  • R" is illustrated by ethylene, propylene, -CH2CHCH3-, butylene, -CH2CH(CH3)CH2-, pentamethylene, hexamethylene, 3-ethyl-hexamethylene, octamethylene, and decamethylene.
  • R ⁇ is typically an alkylene radical having from 2 to 20 carbon atoms.
  • R ⁇ is illustrated by ethylene, propylene, -CH2CHCH3-, butylene, -CH2CH(CH3)CH2-, pentamethylene, hexamethylene, 3-ethyl-hexamethylene, octamethylene, and decamethylene.
  • Typical amino groups are -CH2CH2CH2NH2 and -CH 2 (CH 3 )CHCH 2 (H)NCH 3 , -CH 2 CH 2 NHCH 2 CH 2 NH 2 , -CH 2 CH 2 NH 2 , -CH 2 CH 2 NHCH 3 , -CH 2 CH 2 CH 2 CH 2 NH 2 , -(CH 2 CH 2 NH) 3 H, and -CH 2 CH 2 NHCH 2 CH 2 NHC4H 9 .
  • the R 1 unit of the MQ resin is an alkyl group and more typically a methyl group.
  • MQ resins suitable for use as component (A), and methods for their preparation are known in the art.
  • U.S. Patent No. 2,814,601 to Currie et al., November 26, 1957, which is hereby incorporated by reference discloses that MQ resins can be prepared by converting a water-soluble silicate into a silicic acid monomer or silicic acid oligomer using an acid. When adequate polymerization has been achieved, the resin is end-capped with trimethylchlorosilane to yield the MQ resin.
  • Another method for preparing MQ resins is disclosed in U.S. Patent No.
  • the MQ resins suitable as component A) in the present invention may contain D and T units, providing that at least 80 mole %, alternatively 90 mole % of the total siloxane units are M and Q units.
  • the MQ resins may also contain hydroxy groups.
  • the MQ resins have a total weight % hydroxy content of 0.3-10 weight %, alternatively 2-5 weight %.
  • the ratio of M to Q units (a/b) in the MQ resin ranges from 0.5:1 to 1.1:1. Alternatively, the M to Q ratio of component A) is from 0.6: 1 to 1.0: 1. Alternatively, the M to Q ratio of component A) is from 0.7:1 to 0.95:1.
  • the MQ resin (Component A)) is delivered to the formulation as either a solventless solid or as a solution in a volatile solvent. For the case when the MQ resin is delivered as a solution only the solid content is considered as Component A) and the delivery solvent is accounted for in Component B).
  • Component B) comprises a volatile siloxane solvent, organic solvent, or mixtures of solvents.
  • the volatile siloxane solvent can be a cyclic polysiloxane, a linear polysiloxane, or mixtures thereof.
  • Some representative volatile linear polysiloxanes are hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, tetradecamethylhexasiloxane, and hexadecamethylheptasiloxane.
  • Some representative volatile cyclic polysiloxanes are hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane.
  • the organic solvent can be an alcohol such as methanol, ethanol, isopropanol, butanol, or n-propanol; a ketone such as acetone, methylethyl ketone, or methyl isobutyl ketone; an aromatic hydrocarbon such as benzene, toluene, or xylene; an aliphatic hydrocarbon such as heptane, hexane, octane, or isododecane; a glycol ether such as propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol n-butyl ether, propylene glycol n-propyl ether, or ethylene glycol n-butyl ether, a halogenated hydrocarbon such as dichloromethane, 1,1,1-trichloroethane or methylene chloride, chloroform, dimethyl sulfoxide, dimethyl formamide, ace
  • the volatile solvent is generally present in amounts from 5-10000 parts by weight based on resin solids where "resin solids" is defined as the amount of Component A + Component C in the formulation.
  • the volatile solvent is present in amounts from 5-2000 parts by weight on the same basis.
  • the volatile solvent is present in amounts from 25-2000 parts by weight on the same basis.
  • the volatile solvent is present in amounts from 50-1000 parts by weight on the same basis.
  • Optional Component C) is a propyl silsesquioxane resin comprising at least 80 mole % of R 3 Si ⁇ 3/2 units, where R 3 is independently an alkyl group having from 1 to 8 carbon atoms an aryl group, a carbinol group, or an amino group, and with the proviso that at least 40 mole % of the R 3 groups are propyl.
  • the propyl silsesquioxane resins are referred herein as T-propyl resins, since the majority of the siloxane units are T units of the general formula R 3 SiC" 3/2 where at least 40 mole %, alternatively at least 50 mole %, or alternatively at least 90 mole % of the R 3 groups are propyl.
  • the R 3 groups are illustrated by the same structures as described above for R 1 groups.
  • Silsesquioxane resins are well known in the art and are typically prepared by hydrolyzing an organosilane having three hydrolyzable groups on the silicon atom, such as a halogen or alkoxy group.
  • Component C) can be obtained by hydrolyzing propyltrimethoxysilane, propyltriethoxysilane, propyltripropoxysilane, or by co-hydrolyzing the aforementioned propylalkoxysilanes with various alkoxysilanes.
  • alkoxysilanes examples include methyltrimethoxysilane, methyltriethoxysilane, methyltriisopropoxysilane, dimethyldimethoxysilane, and phenyltrimethoxysilane.
  • Propyltrichlorosilane can also be hydrolyzed alone, or in the presence of alcohol. In this case, co-hydrolyzation can be carried out by adding methyltrichlorosilane, dimethyldichlorosilane, phenyltrichlorosilane, or similar chlorosilanes and methyltrimethoxysilane, methyltriethoxysilane, methyltriisopropoxysilane, or similar methylalkoxysilane.
  • Alcohols suitable for these purposes include methanol, ethanol, n-propyl alcohol, isopropyl alcohol, butanol, methoxy ethanol, ethoxy ethanol, or similar alcohols.
  • hydrocarbon-type solvents which can also be concurrently used include toluene, xylene, or similar aromatic hydrocarbons; hexane, heptane, isooctane, or similar linear or partially branched saturated hydrocarbons; and cyclohexane, or similar aliphatic hydrocarbons.
  • the T-propyl resins suitable as component C) in the present invention may contain M, D, and Q units, providing that at least 80 mole %, alternatively 90 mole % of the total siloxane units are T units.
  • the T-propyl resins may also contain hydroxy and/or alkoxy groups.
  • the T-propyl resins have a total weight % hydroxy content of 2-10 weight % and a total weight % alkoxy content of up to 20 weight %, alternatively 6-8 weight% hydroxy content and up to 10 weight % alkoxy content.
  • the propyl silsesquioxane resin (Component C)) is delivered to the formulation as either a solventless material (liquid or solid depending on the molecular weight and temperature) or as a solution in a volatile solvent.
  • Component C) may be present in amounts from 0-15 parts by weight based on 10 parts of Component A).
  • Component C) is present in amounts from 0.5-15 parts on the same basis.
  • Component C) is present in amounts from 0.5-10 parts on the same basis.
  • the Component C) is present in amounts from 3-10 parts on the same basis.
  • the mixing can be conducted in a batch, semi-continuous, or continuous process.
  • the composition can be applied to the surface of plastic, ceramic or metal substrates by spraying, wiping, dipping or other means, air dried at ambient or elevated temperatures to provide a tack free low energy coating that resists staining by dirt or dust including brake dust.
  • the composition is used to coat automobile wheels, wheel rims, and hubcaps to prevent staining by dust originating from brake pads.
  • Example 1 A formulation containing 10 parts of MQ resin solid (Component A)), having a M:Q ratio of 0.95: 1 with all of the R 1 groups being methyl and ⁇ 1 wt% of silanol groups and 10 parts of toluene (Component B)) was applied to a aluminum panel using a lmil draw down bar and air dried at room temperature for 24 hours. The resulting film was clear, colorless, tack free and resisted staining when brake dust was applied and removed.
  • Component A MQ resin solid
  • Component B 10 parts

Abstract

L'invention porte sur un procédé consistant à réduire un dépôt de poussières et de salissures sur des surfaces par le traitement de telles surfaces par une résine MQ et facultativement une résine de propyl silsesquioxane.
PCT/US2009/034201 2008-03-27 2009-02-16 Procédé de réduction de dépôt de poussières et de salissures WO2009120424A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3992008P 2008-03-27 2008-03-27
US61/039,920 2008-03-27

Publications (1)

Publication Number Publication Date
WO2009120424A1 true WO2009120424A1 (fr) 2009-10-01

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005075567A1 (fr) * 2004-02-02 2005-08-18 Dow Corning Corporation Compositions de resine siloxane mq et t-propyle
US20070128962A1 (en) * 2005-12-02 2007-06-07 Serobian Ashot K Aqueous composition and method for imparting resistance to stain absorption

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005075567A1 (fr) * 2004-02-02 2005-08-18 Dow Corning Corporation Compositions de resine siloxane mq et t-propyle
US20070166271A1 (en) * 2004-02-02 2007-07-19 Gordon Glenn V Mq and t-propyl siloxane resins compositions
US20070128962A1 (en) * 2005-12-02 2007-06-07 Serobian Ashot K Aqueous composition and method for imparting resistance to stain absorption

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