US20200361191A1 - Treated substrate having hydrophobic and durability properties - Google Patents

Treated substrate having hydrophobic and durability properties Download PDF

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Publication number
US20200361191A1
US20200361191A1 US16/640,187 US201816640187A US2020361191A1 US 20200361191 A1 US20200361191 A1 US 20200361191A1 US 201816640187 A US201816640187 A US 201816640187A US 2020361191 A1 US2020361191 A1 US 2020361191A1
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United States
Prior art keywords
alkyl
group
adhesion promoter
integer
substrate
Prior art date
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Abandoned
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US16/640,187
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English (en)
Inventor
Jiangping Wang
John Mitchell Moore, Jr.
Bong June Zhang
Esra ALTINOK
Perry L. CATCHINGS, SR.
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.)
Agc Automotive Americas Co A Division Of Agc Flat Glass North America Inc
NBD Nanotechnologies Inc
Original Assignee
AGC Automotive Americas R&D Inc
NBD Nanotechnologies Inc
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Application filed by AGC Automotive Americas R&D Inc, NBD Nanotechnologies Inc filed Critical AGC Automotive Americas R&D Inc
Priority to US16/640,187 priority Critical patent/US20200361191A1/en
Assigned to NBD NANOTECHNOLOGIES, INC. reassignment NBD NANOTECHNOLOGIES, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ALTINOK, ESRA, CATCHINGS, PERRY L., SR., ZHANG, Bong June
Assigned to AGC AUTOMOTIVE AMERICAS R&D, INC. reassignment AGC AUTOMOTIVE AMERICAS R&D, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MOORE, JOHN MITCHELL, JR., WANG, JIANGPING
Publication of US20200361191A1 publication Critical patent/US20200361191A1/en
Assigned to AGC AUTOMOTIVE AMERICAS CO., A DIVISION OF AGC FLAT GLASS NORTH AMERICA INC. reassignment AGC AUTOMOTIVE AMERICAS CO., A DIVISION OF AGC FLAT GLASS NORTH AMERICA INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: AGC AUTOMOTIVE AMERICAS R&D, INC.
Abandoned legal-status Critical Current

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    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2255/00—Coating on the layer surface
    • B32B2255/28—Multiple coating on one surface
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
    • B32B2262/10—Inorganic fibres
    • B32B2262/101—Glass fibres
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/30—Properties of the layers or laminate having particular thermal properties
    • B32B2307/306—Resistant to heat
    • B32B2307/3065—Flame resistant or retardant, fire resistant or retardant
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B32B2307/412—Transparent
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B32B2307/418—Refractive
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/50—Properties of the layers or laminate having particular mechanical properties
    • B32B2307/546—Flexural strength; Flexion stiffness
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
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    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/50—Properties of the layers or laminate having particular mechanical properties
    • B32B2307/558—Impact strength, toughness
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/70—Other properties
    • B32B2307/726—Permeability to liquids, absorption
    • B32B2307/7265—Non-permeable
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
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    • B32B2307/00—Properties of the layers or laminate
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    • B32B2307/73—Hydrophobic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
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    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B2605/00—Vehicles
    • B32B2605/006—Transparent parts other than made from inorganic glass, e.g. polycarbonate glazings

Definitions

  • the invention generally relates to treated substrates and, more particularly, to treated substrates having hydrophobic and durability properties.
  • Treated substrates are used in various fields to provide enhanced physical properties to untreated substrates.
  • the application or disposition of one or more layers of a composition or compositions to an untreated substrate to form a treated substrate and associated articles may improve a particular physical property or properties as compared to the untreated substrate.
  • the application or disposition of an adhesion promoter layer in combination with a topcoat layer to a glass substrate to form a treated glass substrate may provide an increase in hydrophobicity that allows the treated glass substrate to more easily repel water (i.e., has increased water repellency properties) or be cleaned as compared with the corresponding untreated glass substrate.
  • the enhanced property or properties, such as hydrophobicity, provided by the addition of the one or more layers to the untreated substrate decrease over time due to environmental conditions or the like that adversely impact the durability of such applied layers. It would thus be desirable to form treated substrates that have enhanced durability while providing other desired physical properties such as increased hydrophobicity and associated water repellent properties.
  • the subject invention relates to a treated substrate that comprises a substrate, an adhesion promoter layer disposed on the substrate, and a topcoat layer disposed on the adhesion promoter layer.
  • the adhesion promoter layer is formed from an adhesion promoter composition, with the adhesion promoter composition comprising a polyhedral oligomeric silsesquioxane or a linear organosilane polymer.
  • the topcoat layer is formed from a topcoat composition, with the topcoat composition comprising at least one fluorinated organic silicon compound which contains no etheric oxygen atom and at least one fluorinated organic silicon compound which contains an etheric oxygen atom.
  • the treated substrate has excellent initial hydrophobic properties and related water repellent properties, and retains such hydrophobic properties under a wide variety of test conditions intended to simulate environmental conditions, which evidences the durability of the treated substrates, particularly as compared with other treated substrates that include only one of adhesion promoter layers and topcoat layers as described above, or alternatively as compared with treated substrates utilizing a different adhesion promoter composition or topcoat composition to form its respective adhesion promoter and topcoat layers.
  • FIG. 1 is perspective side view of a treated substrate in accordance with one embodiment of the subject invention.
  • a treated substrate 10 that includes a substrate 14 , an adhesion promoter layer 16 disposed on the substrate 14 , and a topcoat layer 18 disposed on the adhesion promoter layer 16 .
  • the substrate 14 may be rigid or flexible material.
  • the rigid or flexible material is also substantially transparent.
  • substantially transparent refers to a material that allows 70% or more of light transmission in a predefined wavelength range, such as the visible light range to travel therethrough.
  • suitable rigid substrates include inorganic materials, such as glass plates or panels.
  • the panes of glass are preferably automotive glass and, more specifically, soda-lime-silica glass.
  • the glass panel is a tempered glass panel, which is a single layer glass panel that has been processed by controlled thermal or chemical treatments to increase its strength compared to normal glass (i.e., untempered glass such as the soda-lime-silica glass or annealed glass).
  • the substrate 14 may be flexible (i.e., a flexible substrate).
  • specific examples of the flexible substrate include those comprising various organic polymers. From the view point of transparency, refractive index, heat resistance and durability, specific examples of the flexible substrate include those comprising polyolefins (polyethylene, polypropylene, etc.), polyesters (poly(ethylene terephthalate), poly(ethylene naphthalate), etc.), polyamides (nylon 6, nylon 6,6, etc.), polystyrene, poly(vinyl chloride), polyimides, polycarbonates, polynorbornenes, polyurethanes, poly(vinyl alcohol), poly(ethylene vinyl alcohol), polyacrylics, celluloses (triacetylcellulose, diacetylcellulose, cellophane, etc.), or interpolymers (e.g. copolymers) of such organic polymers.
  • the substrate 14 is in the form of a laminated glass panel assembly that includes an inner transparent sheet and an outer transparent sheet and an interlayer disposed between the inner transparent sheet and the outer transparent sheet.
  • the inner and outer transparent sheets are panes of glass that are substantially transparent.
  • the inner and outer transparent sheets may be plastic, fiberglass, or any other suitable substantially transparent material.
  • the inner and outer transparent sheets are panes of glass that are less transparent.
  • the glass assembly is a privacy glass
  • the transparency of the glass assembly is substantially reduced, and thus allows less than 70% light transmission in a predefined wavelength range, such as from greater than 0 to 70% light transmission at the predefined wavelength range.
  • the laminated glass panel assembly also includes an interlayer disposed between the inner and outer transparent sheets.
  • the interlayer bonds the inner and outer transparent sheets and allows the laminated glass panel assembly to retain glass panel pieces upon impact or breakage.
  • the interlayer typically is typically substantially transparent to light and includes a polymer or thermoplastic resin, such as polyvinyl butyral (PVB). However, other suitable materials for implementing the interlayer may be utilized. Similar to the inner and outer transparent sheets, the interlayer is also substantially transparent or otherwise transparent to light, and accordingly the laminated glass panel assembly that includes the interlayer between the inner and outer transparent sheets is also substantially transparent or otherwise transparent to light.
  • PVB polyvinyl butyral
  • the substrate 14 may be reinforced, e.g. with fillers and/or fibers.
  • the treated substrate 10 also includes an adhesion promoter layer 16 disposed on the substrate 14 .
  • the adhesion promoter layer 16 is formed from an adhesion promoter composition.
  • the adhesion promoter composition comprises a polyhedral oligomeric silsesquioxane.
  • Silsesquioxanes have a cage-like structure, which is most commonly a cube, hexagonal prism, octagonal prism, decagonal prism, or dodecagonal prism.
  • the cube-like (“T8”) cage structure is formed.
  • the cube-like (“T8”) cage structure is represented by the shorthand:
  • each corner will bear a substituent, such as a fluorinated alkyl group, or a group bearing a reactive functionality such as an alkylsilane or an alkylisocyanate.
  • a substituent such as a fluorinated alkyl group, or a group bearing a reactive functionality such as an alkylsilane or an alkylisocyanate.
  • the polyhedral oligomeric silsesquioxane is of the formula (I), (II), or (III):
  • R 1 is a long chain alkyl or long chain fluorinated alkyl
  • R 2 and R 3 are each independently selected from the group consisting of C 1 -C 15 alkyl, C 2 -C 15 alkenyl, —NCO, —CH(O)CH 2 , —NH 2 , —NHC 1 -C 6 alkyl, —OC(O)NHC 1 -C 6 alkyl, —OC(O)NH 2 , —P(O)(OC 1 -C 6 , alkyl) 2 , —C 1 -C 6 alkylSi(C 1 -C 6 alkyl) 3 , —C 1 -C 6 alkylSi(C 1 -C 6 alkyl) 2 (OC 1 -C 6 alkyl), —C 1 -C 6 alkylSi(C 1 -C 6 alkyl)(OC 1 -C 6 alkyl) 2 —C 1 -C 6 alkylSi(OC 1 -C 6 alkyl) 3 , —Si(CrC 6
  • n is an integer from 0 to 7;
  • n is an integer from 0 to 7;
  • p is an integer from 0 to 6;
  • q is an integer from 0 to 6;
  • n and m are less than or equal to 7; and the sum of p and q is less than or equal to 6.
  • the end functionalities employed on the R 2 and R 3 groups may incorporate one or more functional groups to allow the polyhedral oligomeric silsesquioxane to covalently bond to various topcoat compositions, including the topcoat compositions described below that form the topcoat layer.
  • Such end functionalities include those described for R 2 and R 3 in formulas (I), (II), and (III) above.
  • the adhesion promoter composition comprises a linear organosilane polymer.
  • linear as used herein may refer to a structure having non-branched or non-caged structure in polymeric backbone.
  • the linear organosilane polymer may include units having the following formula:
  • each R is the same or different and may be a hydrogen or non-hydrogen substituent;
  • L 1 is a linker group; and
  • y is a positive integer.
  • each L is a bond, alkylene, or heteroalkylene. In some embodiments, each L 1 is not a bond. In some embodiments, each L 1 is a C 1 -C 2 alkylene which may be substituted or unsubstituted. In some embodiments, each L 1 is a C 1 -C 10 alkylene which may be substituted or unsubstituted. In some embodiments, each L 1 is a C 1 -C 8 alkylene which may be substituted or unsubstituted. In some embodiments, each L 1 is a C 1 -C 6 alkylene which may be substituted or unsubstituted.
  • each L 1 is a C 1 -C 4 alkylene which may be substituted or unsubstituted. In some embodiments, each L 1 is a C 1 -C 2 alkylene which may be substituted or unsubstituted. In some embodiments, each L 1 is methylene or ethylene. In some embodiments, each L 1 is a heteroalkylene which may be substituted or unsubstituted. In some embodiments, each L 1 is a heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted.
  • each L 1 is a 2 to 20 membered heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted. In some embodiments, each L 1 is a 2 to 10 membered heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted. In some embodiments, each L 1 is a 2 to 8 membered heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted.
  • each L 1 is a 2 to 5 membered heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted. In some embodiments, each L 1 is a 2 to 3 membered heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted.
  • the linear organosilane polymer may include units of the following formula:
  • each R is the same or different and may be a hydrogen or non-hydrogen substituent;
  • L 2 is a linker group; and
  • y is a positive integer.
  • each L 2 is a bond, alkylene, or heteroalkylene. In some embodiments, each L 2 is not a bond. In some embodiments, each L 2 is a C 1 -C 2 alkylene which may be substituted or unsubstituted. In some embodiments, each L 2 is a C 1 -C 10 alkylene which may be substituted or unsubstituted. In some embodiments, each L 2 is a C 1 -C 8 alkylene which may be substituted or unsubstituted. In some embodiments, each L 2 is a C 1 -C 6 alkylene which may be substituted or unsubstituted.
  • each L 2 is a C 1 -C 4 alkylene which may be substituted or unsubstituted. In some embodiments, each L 2 is a C 1 -C 2 alkylene which may be substituted or unsubstituted. In some embodiments, each L 2 is methylene or ethylene. In some embodiments, each L 2 is a heteroalkylene which may be substituted or unsubstituted. In some embodiments, each L 2 is a heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted.
  • each L 2 is a 2 to 20 membered heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted. In some embodiments, each L 2 is a 2 to 10 membered heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted. In some embodiments, each L 2 is a 2 to 8 membered heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted.
  • each L 2 is a 2 to 5 membered heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted. In some embodiments, each L 2 is a 2 to 3 membered heteroalkylene including at least one selected from O, S, N, or P, which may be substituted or unsubstituted.
  • the linear organosilane polymer may include units of the
  • each R is the same or different and may be a hydrogen or non-hydrogen substituent; and y is a positive integer.
  • the linear organosilane polymer may include units of the following formula:
  • the linear organosilane polymer may include units of the following formula:
  • each R is the same or different and may be a hydrogen or non-hydrogen substituent
  • each X and X′ is the same or different and may be hydrogen or a non-hydrogen substituent
  • each x is the same or different positive integer
  • y and z are each the same or different positive integer.
  • each X and X′ is hydrogen. In some embodiments, each X and X′ is other than hydrogen.
  • each X and X′ is alkyl, which may be substituted or unsubstituted. In some embodiments, X and X′ is unsubstituted alkyl. In some embodiments, X and X′ is unsubstituted C 1 -C 3 alkyl. In some embodiments, each X and X′ is ethyl. In some embodiments, each X and X′ is methyl. In some embodiments, each X and X′ is halogen (e.g., F, Cl, Br, or I).
  • the linear organosilane polymer may include units of the following formula:
  • each R is the same or different and may be a hydrogen or non-hydrogen substituent; each x is the same or different positive integer; and y and z are each the same or different positive integer.
  • each R is other than hydrogen.
  • each R is alkyl, which may be substituted or unsubstituted.
  • R is unsubstituted alkyl.
  • R is unsubstituted C 1 -C 3 alkyl.
  • each R is ethyl.
  • each R is methyl.
  • y is an integer from 1 to 1000. In some embodiments, y is an integer from 1 to 900. In some embodiments, y is an integer from 1 to 800. In some embodiments, y is an integer from 1 to 700. In some embodiments, y is an integer from 1 to 600. In some embodiments, y is an integer from 1 to 500. In some embodiments, y is an integer from 1 to 400. In some embodiments, y is an integer from 1 to 300. In some embodiments, y is an integer from 1 to 200. In some embodiments, y is an integer from 1 to 100. In some embodiments, y is an integer from 1 to 90. In some embodiments, y is an integer from 1 to 80.
  • y is an integer from 1 to 70. In some embodiments, y is an integer from 1 to 60. In some embodiments, y is an integer from 1 to 50. In some embodiments, y is an integer from 1 to 40. In some embodiments, y is an integer from 1 to 30. In some embodiments, y is an integer from 1 to 20. In some embodiments, y is an integer from 1 to 10. In some embodiments, z is an integer from 0 to 1000. In some embodiments, z is an integer from 0 to 900. In some embodiments, z is an integer from 0 to 800. In some embodiments, z is an integer from 0 to 700. In some embodiments, z is an integer from 0 to 600.
  • z is an integer from 0 to 500. In some embodiments, z is an integer from 0 to 400. In some embodiments, z is an integer from 0 to 300. In some embodiments, z is an integer from 0 to 200. In some embodiments, z is an integer from 0 to 100. In some embodiments, z is an integer from 0 to 90. In some embodiments, z is an integer from 0 to 80. In some embodiments, z is an integer from 0 to 70. In some embodiments, z is an integer from 0 to 60. In some embodiments, z is an integer from 0 to 50. In some embodiments, z is an integer from 0 to 40. In some embodiments, z is an integer from 0 to 30.
  • z is an integer from 0 to 20. In some embodiments, z is an integer from 0 to 10. In some embodiments, x is an integer from 1 to 30. In some embodiments, x is an integer from 1 to 20. In some embodiments, x is an integer from 1 to 10. In some embodiments, x is an integer from 1 to 9. In some embodiments, x is an integer from 1 to 8. In some embodiments, x is an integer from 1 to 7. In some embodiments, x is an integer from 1 to 6. In some embodiments, x is an integer from 1 to 5. In some embodiments, x is an integer from 1 to 4. In some embodiments, x is an integer from 1 to 9. In some embodiments, x is an integer from 1 to 3. In some embodiments, x is an integer from 1 to 9. In some embodiments, x is an integer from 1 to 2. In some embodiments, x is 1.
  • the adhesion promoter composition is of the formula: C m H n O p Si q , wherein the subscript m ranges from 64 to 170, the subscript n ranges from 150 to 402, the subscript p ranges from 36 to 99, and the subscript q ranges from 15 to 45.
  • the adhesion promoter composition is a polyhedral oligomeric silsesquioxane of the formula: C 170 H 402 O 99 Si 45 .
  • the adhesion promoter composition is a linear organosilane polymer of the formula: C 64 H 152 O 36 Si 16 .
  • the adhesion promoter composition in addition to the polyhedral oligomeric silsesquioxane or the linear organosilane polymer, also comprises additional components.
  • additional components include, but are not limited to solvents and acids.
  • Suitable solvents that can be included include organic solvents, including polar organic solvents such as ethanol or methanol.
  • polar organic solvents such as ethanol or methanol.
  • One exemplary polar organic solvent that can be used is ethanol.
  • Suitable acids include any acids that are capable of adjusting the pH of the adhesion promoter composition to approximately 2 and include, but are aqueous acids and certain, but are not limited to, nitric acid, sulfuric acid, hydrochloric acid, and the like.
  • the treated substrate 10 also includes the topcoat layer 18 disposed on the adhesion promoter layer 16 .
  • the topcoat layer 18 is formed from a topcoat composition that comprises at least one fluorinated organic silicon compound which contains no etheric oxygen atom (i.e., Compound (A)) and at least one fluorinated organic silicon compound which contains an etheric oxygen atom (i.e., Compound (B)).
  • the compound (A) is selected from the group consisting of a compound represented by the following formula (1a), its partially hydrolyzed condensate, and a compound represented by the following formula (1b):
  • R f1 is a C 1-20 perfluoroalkyl group which contains no etheric oxygen atom between carbon-carbon atoms and which may have a ring structure
  • Y is a C 1-6 bivalent organic group which contains no fluorine atom
  • R 11 each independently is a hydrogen atom or a C 1-6 hydrocarbon group which contains no fluorine atom
  • X 1 each independently is a halogen atom, an alkoxy group or an isocyanate group
  • r is an integer of from 0 to 2
  • R 1 is a hydrogen atom or a C 1-3 hydrocarbon group which contains no fluorine atom
  • b is an integer of from 1 to 100).
  • the compound (B) is selected from the group consisting of a compound represented by the following formula (2a), its partially hydrolyzed condensate, and a compound represented by the following formula (2b):
  • R f2 is a C 1-20 perfluoroalkyl group which may have an etheric oxygen atom inserted between carbon-carbon atoms and which may have a ring structure
  • W is —O—(CF 2 CF 2 O) a —CF 2 —
  • Z is a bivalent organic group
  • R 12 each independently is a hydrogen atom or a C 1-16 hydrocarbon group which contains no fluorine atom
  • X 2 each independently is a halogen atom, an alkoxy group or an isocyanate group
  • p is an integer of from 0 to 2
  • R 2 is a hydrogen atom or a C 1-3 hydrocarbon group which contains no fluorine atom
  • c is an integer of from 1 to 100).
  • the compound (A) which is contained in the topcoat composition for forming a topcoat layer of the exemplary embodiment is at least one fluorinated organic silicon compound which contains no etheric oxygen atom and which is selected from the group consisting of a compound represented by the following formula (1a), its partially hydrolyzed condensate, and a compound represented by the following formula (1b).
  • a compound represented by the following formula (1a) A partially hydrolyzed condensate of the compound represented by the following formula (1a) will be described later. Firstly, the compound (A) which is not a partially hydrolyzed condensate, will be described.
  • the compound (A) may be composed solely of the compound represented by the above formula (1a), may be composed solely of the compound represented by the above formula (1b), or may be composed of their mixture.
  • R f1 is a C 1-20 perfluoroalkyl group which contains no etheric oxygen atom between carbon-carbon atoms and which may have a ring structure. So long as the above conditions are satisfied, R f1 may be of a linear structure, a branched structure or a cyclic structure, or of a structure which partially has a branched structure and a cyclic structure. As such R f1 , the following groups may specifically be mentioned:
  • 1 is an integer of from 0 to 19, preferably an integer of from 0 to 15, particularly preferably an integer of from 0 to 6.
  • n is a perfluoroadamantyl group.
  • m and n is an integer of from 0 to 15.
  • R f1 in the subject invention CF 3 (CF 2 ), is preferred, and one having a linear structure is further preferred. Further, a preferred number of carbon atoms in R ⁇ 1 may be from 3 to 8.
  • Y being a group which links R f1 and a silicon atom, is a C 1-6 bivalent organic group which contains no fluorine atom and is not particularly limited other than such a condition.
  • Y is preferably a bivalent organic group selected from (CH 2 ), (wherein i is an integer of from 1 to 6), —CONH(CH 2 ) j — (wherein j is an integer of from 1 to 5) and —CONH(CH 2 ) 5-k — (wherein k is an integer of from 1 to 4), more preferably —(CH 2 ) 2 —, —CONH(CH 2 ) 3 —, —CONH(CH 2 ) 2 NH(CH 2 ) 3 or the like.
  • R 11 each independently is a hydrogen atom or a C 1-6 hydrocarbon group which contains no fluorine atom.
  • R 11 is preferably a C 1-4 hydrocarbon group, particularly preferably a methyl group or an ethyl group.
  • R 11 is preferably a hydrogen atom.
  • X 1 is a halogen atom, an alkoxy group or an isocyanate group. Each of them is a hydrolyzable group.
  • r is 0 or 1
  • a plurality of X 1 may be the same or different.
  • X 1 is preferably a chlorine atom, a C 1-4 alkoxy group or an isocyanate group, particularly preferably a chlorine atom.
  • r is an integer of from 0 to 2, preferably 0 or 1, since the adhesion, the durability, etc. of the formed layer will be thereby excellent.
  • R 1 each independently is a hydrogen atom or a C 1-3 hydrocarbon group which contains no fluorine atom.
  • R 1 is preferably a hydrogen atom with a view to improvement of the reactivity.
  • b is an integer of from 1 to 100.
  • b represents the number of units of the silicon-nitrogen bond in the compound represented by the formula (1b), and in the subject invention, b is preferably from 1 to 50 from the viewpoint of the coating property.
  • one type of the compound (A) may be used alone, or two or more types of the compound (A) may be used in combination.
  • the above compound (A) to be used in the subject invention can be produced by a common method. Further, as the compound (A), a commercial product is available, and therefore, in the subject invention, it is possible to employ such a commercial product.
  • the compound (B) contained in the composition of the exemplary embodiment is at least one fluorinated organic silicon compound which contains an etheric oxygen atom and which is selected from the group consisting of a compound represented by the following formula (2a), its partially hydrolyzed condensate, and a compound represented by the following formula (2b).
  • the partially hydrolyzed condensate of the compound represented by the following formula (2a) will be described later. Firstly, the compound (B) which is not a partially hydrolyzed condensate, will be described.
  • Compounds represented by formulae (2a) and (2b) may be as follows:
  • the compound (B) may be composed solely of the compound represented by the above formula (2a), may be composed solely of the compound represented by the above formula (2b), or may be composed of their mixture.
  • R f2 is a C 1-20 perfluoroalkyl group, (which may have a ring structure or may have an etheric oxygen atom inserted between carbon-carbon atoms).
  • the C 1-20 perfluoroalkyl group represented by R f2 may be of a linear structure, a branched structure, a cyclic structure, or a structure which partially has a branched structure and a cyclic structure.
  • R f2 the following groups may specifically be mentioned:
  • 1 is an integer of from 0 to 19, preferably an integer of from 0 to 15, particularly preferably an integer of from 0 to 6.
  • n is a perfluoroadamantyl group.
  • m and n is an integer of from 0 to 15.
  • R f2 in the subject invention CF 3 (CF 2 ) m — is preferred, and one having a linear structure is more preferred. Further, the number of carbon atoms in R f2 is preferably from 1 to 16, particularly preferably from 1 to 8.
  • the perfluoroalkyl group having an etheric oxygen atom inserted between carbon-carbon atoms is a group having an etheric oxygen atom inserted between carbon-carbon atoms of the above-mentioned perfluoroalkyl group.
  • a perfluoro(oxyethylene) group i.e. —OCF 2 CF 2 — is formed on the bond terminal side in the perfluoroalkyl group, such a perfluoro(oxyethylene) group is regarded as a perfluoro(oxyethylene) group in W in the above formula.
  • a perfluoro(oxyethylene) group is not linked to the perfluoro(oxyethylene) group in W, it is a perfluoro(oxyethylene) group in R 12 .
  • the etheric oxygen atom in R 12 may form a perfluoro(oxypropylene) group, but a perfluoro(oxypropylene) group may not be able to sufficiently exhibit the desired effect due to the presence of a trifluoromethyl) group as its side chain. Therefore, in a case where there are two or more etheric oxygen atoms inserted in R f2 , they preferably form a structure wherein two or more units of perfluoro(oxyethylene) groups are repeated.
  • a perfluoroalkyl group having an etheric oxygen atom inserted does not have a —OCF 2 O— structure.
  • the —OCF 2 O— structure is a structure, on which the presence of a nuclear structure cannot be detected by a usual analytical method (such as 19 F-NMR (nuclear magnetic resonance)).
  • a usual analytical method such as 19 F-NMR (nuclear magnetic resonance)
  • —OCF 2 O— is likely to be formed at one end of such a structure in many cases.
  • the —OCF 2 O— structure in R f2 is unstable and is likely to bring about deterioration of the heat resistance.
  • the number of oxygen atoms to be inserted is preferably from 1 to 7, more preferably from 1 to 4.
  • the positions of such oxygen atoms to be inserted are between carbon atom-carbon atom single bonds, and the number of carbon atoms present between oxygen atoms is at least 2.
  • W is a bivalent organic group represented by —O—(CF 2 CF 2 O) a —CF 2 —, wherein a is an integer of from 1 to 200.
  • a is preferably an integer of from 3 to 50, more preferably from 4 to 25, further preferably from 5 to 10.
  • Z is a bivalent organic group.
  • This bivalent organic group preferably has at most 10 carbon atoms and may have a hetero atom such as an oxygen atom or a nitrogen atom.
  • the compound (B) is produced by reacting a compound having R f2 —W— with a compound having a silicon atom (i.e. by reacting a functional group at the silicon atom side terminal of W with a functional group of the compound having a silicon atom).
  • Z is preferably a bivalent organic group to be formed by a reaction of a reactive group-containing organic group bonded to such a silicon atom with the above-mentioned reactive group bonded to the terminal of W.
  • a compound having an alkenyl group at the silicon atom side terminal of W and a silicon atom having hydrogen atoms bonded to the silicon atom may be bonded by a hydrosilylation reaction to obtain a compound wherein Z is an alkylene group.
  • Z is a bivalent organic group to be formed by a reaction of a functional group at the silicon atom side terminal of W with a functional group of the compound having a silicon atom.
  • the reactive group bonded to a difluoromethylene group at the terminal of W may, for example, be a reactive group having a carbonyl group such as a carboxyl group, a halocarbonyl group or an alkoxycarbonyl group, or a hydroxymethyl group.
  • the reactive group in the compound having a silicon atom may be a reactive group having an organic group bonded to the silicon atom.
  • a 3-aminopropyl group or an N-(2-aminoethyl)-3-aminopropyl group an isocyanate group such as a 3-isocyanate propyl group, a chlorine atom group bonded to a carbon atom such as a 3-chloropropyl group, an epoxy group such as a 3-glycidyl oxypropyl group, a hydroxy group such as a 3-hydroxypropyl group, or a mercapto group such as a 3-mercaptooxypropyl group, may be mentioned.
  • Z represented by —CONHC 3 H 6 — will be formed.
  • Z is preferably a bivalent organic group selected from —CONHC 3 H 6 —, —CONHC 2 H 4 —, —CH 2 OCONHC 3 H 6 —, —COCH 2 CH(OH)CH 2 OC 3 H 6 —, —CH 2 OCH 2 CH(OH)CH 2 OC 3 H—, —CH 2 OC 3 H 6 , —CF 2 OC 3 H 6 —, —C 2 H 4 — and —C 3 H 6 —.
  • —CONHC 3 H 6 —, —CONHC 2 H 4 — or —C 2 H 4 — is particularly preferred.
  • R 12 may be the same groups as R 11 in the above-mentioned formulae (1a) and (1b). Its preferred examples are also the same as mentioned above.
  • X 2 may be the same group as X 1 in the above formula (1a). Its preferred examples are also the same as mentioned above.
  • p is an integer of from 0 to 2, but is preferably 0 or 1, since the adhesion, the durability, etc. of the formed layer will thereby be excellent.
  • R 2 may be the same group as R 1 in the above formula (1b). Its preferred examples are also the same as mentioned above, c is one representing the number of units of silicon-nitrogen bonds in the compound represented by the formula (2b), and in the subject invention, c is preferably from 1 to 50 from the viewpoint of the coating property.
  • one type of the compound (B) may be used alone, or two or more types may be used in combination.
  • the above compound (B) to be used in the subject invention can be produced by a known method.
  • the above compound (B) can be produced specifically by the method disclosed in WO2009-008380, which is herein incorporated by reference.
  • the compound represented by the formula (1a) and the compound represented by the formula (2a) may be their respective partially hydrolyzed condensates.
  • a partially hydrolyzed condensate is meant for an oligomer to be formed by hydrolysis of all or some of hydrolyzable silyl groups in a solvent in the presence of a catalyst such as an acid catalyst or an alkali catalyst, followed by dehydration condensation.
  • a catalyst such as an acid catalyst or an alkali catalyst
  • the condensation degree (oligomerization degree) of such a partially hydrolyzed condensate is required to be such a degree that the product is soluble in a solvent.
  • the compound (A) to be contained in the composition for forming a topcoat layer of the exemplary embodiment may be a partially hydrolyzed condensate of the compound represented by the formula (1a), and likewise, the compound (B) may be a partially hydrolyzed condensate of the compound represented by the formula (2a). Further, they may contain the respective unreacted compounds represented by the formulae (1a) and (2a).
  • the topcoat composition for forming a topcoat layer of the exemplary embodiment comprises the above compounds (A) and (B).
  • the compounds (A) and (B) may be contained in the form of the above-described compounds themselves in the topcoat composition for forming a topcoat layer of the exemplary embodiment.
  • the topcoat composition for forming a topcoat layer of the exemplary embodiment preferably contains the compound (A) in the form of the compound represented by the formula (1a) and/or its partially hydrolyzed condensate, and the compound (B) preferably is in the form of the compound represented by the formula (2a) and/or its partially hydrolyzed condensate. In such a case, it is more preferred that they are contained in the form of a partially hydrolyzed co-condensate of the compounds (A) and (B).
  • the partially hydrolyzed co-condensate of the compounds (A) and (B) is also meant for an oligomer to be formed by hydrolysis of all or some of hydrolyzable silyl groups in a solvent in the presence of a catalyst such as an acid catalyst or an alkali catalyst, followed by dehydration condensation, but here, the oligomer is one obtainable by hydrolytic condensation of a mixture of two types of hydrolyzable silyl group-containing compounds (i.e.
  • the compound (A) a compound represented by the formula (1a) and/or its partially hydrolyzed condensate
  • the compound (B) a compound represented by the formula (2a) and/or its partially hydrolyzed condensate
  • the condensation degree (oligomerization degree) of such a partially hydrolyzed co-condensate is required to be such that the product is soluble in a solvent.
  • the partially hydrolyzed co-condensate is one to be formed by reacting, as the compound (A), a compound represented by the formula (1a) and/or its partially hydrolyzed condensate, and, as the compound (B), a compound represented by the formula (2a) and/or its partially hydrolyzed condensate in a solvent containing them, and may contain unreacted compounds (A) and (B).
  • the compound (A) a compound represented by the formula (1a) (not its partially hydrolyzed condensate) is used, and as the compound (B), a compound represented by the formula (2a) (not its partially hydrolyzed condensate) is used.
  • the partially hydrolyzed co-condensate of the compounds (A) and (B) can be produced by dissolving in a solvent a prescribed amount of a compound represented by the formula (1a) and/or its partially hydrolyzed condensate, and a prescribed amount of a compound represented by the formula (2a) and/or its partially hydrolyzed condensate, followed by stirring for a prescribed time in the presence of a catalyst such as an acid catalyst or an alkali catalyst, and water.
  • a catalyst such as an acid catalyst or an alkali catalyst, and water.
  • the acid catalyst hydrochloric acid, nitric acid, acetic acid, sulfuric acid, phosphoric acid, sulfonic acid, methane sulfonic acid or p-toluene sulfonic acid may, for example, be used.
  • sodium hydroxide, potassium hydroxide or aqueous ammonia may, for example, be used.
  • aqueous solution of such a catalyst water required for the hydrolysis may be present in the reaction system.
  • the obtained solution of the partially hydrolyzed co-condensate may be used as it is, as the composition for forming a topcoat layer of the exemplary embodiment.
  • the topcoat layer is made of a hydrolyzed co-condensate of the two compounds and becomes a film wherein units derived from the two compounds are uniformly dispersed.
  • the hydrolyzed co-condensate of the two compounds can be formed in a relatively short time, and in a film directly formed from the compound represented by the formula (1a) and the compound represented by the formula (2a), it is likely that the uniformity in the distribution of the units derived from the two compounds tends to deteriorate.
  • uniformity is considered to be improved.
  • compositional proportions of effective components in the topcoat composition for forming a topcoat layer of the exemplary embodiment can be determined from the amounts of the compounds (A) and (B) to be used. In a case where the composition comprises the compounds (A) and (B), the compositional proportions can be determined by the proportions of the two compounds used for producing the composition. However, in a case where the composition for forming a topcoat layer of the exemplary embodiment contains the above-mentioned partially hydrolyzed co-condensate, it is difficult to measure the compositional proportions of the effective components in such a partially hydrolyzed co-condensate.
  • the compositional pro-portions of the effective components are determined by the starting material composition before producing the partially hydrolyzed co-condensate. That is, the compositional proportions of the effective components are determined from the amounts of the compounds (A) and (B) used as starting materials for the partially hydrolyzed co-condensate.
  • composition for forming a topcoat layer is formed by producing a partially hydrolyzed co-condensate from the compound represented by the formula (1a) and the compound represented by the formula (2a)
  • the compositional proportions of units of the compound represented by the formula (1a) and units of the compound represented by the formula (2a) in the partially hydrolyzed co-condensate are regarded to be the same as the compositional proportions of the two starting material compounds used.
  • the proportion of the compound (B) in the topcoat composition for forming a topcoat layer of the exemplary embodiment is preferably from 10 to 90 mass %, more preferably from 10 to 60 mass %, particularly preferably from 10 to 30 mass %, as the mass percentage of the compound (B) to the total mass of the compounds (A) and (B) represented by [compound (B)]/[compounds (A) and (B)] ⁇ 100.
  • the proportion of the compound (A) in the topcoat composition for forming a topcoat layer of the exemplary embodiment is preferably from 90 to 10 wt %, more preferably from 90 to 40 mass %, particularly preferably from 90 to 70 mass %, as mass percentage of the compound (A) to the total mass of the compounds (A) and (B).
  • the mass percentage here is a compositional proportion calculated from the amounts of the compounds (A) and (B) before the reaction.
  • the subject invention is also directed to a method for producing a treated substrate utilizing the afore-mentioned adhesion promoter composition and topcoat composition, each in accordance with the subject invention.
  • the method begins by providing the substrate (i.e., the untreated substrate) as described above.
  • the substrate has been cleaned using a solvent or an appropriate cleaning treatment known to those of ordinary skill.
  • the substrate may be cleaned first with a 2% CeO 2 solution, then rinsed with deionized water and dried using compressed air.
  • the process continues by applying the adhesion promoter composition onto at least a part of a surface of a substrate.
  • the adhesion promoter composition in certain embodiments, comprises the polyhedral oligomeric silsesquioxane as described above, such as the polyhedral oligomeric silsesquioxane of formula (I), (II), or (III).
  • the adhesion promoter composition comprises the linear organosilane polymer described above, such as the linear organosilane polymers comprising units of the formula (IV), (V), (VI), (VII), (VIII) or (IX) described above.
  • the method of application of the adhesion promoter composition is not limited, and may include applying the composition by a spray application, a dipping application, a wiping application, or the like.
  • a wiping application is used, wherein the adhesion promoter composition is wiped onto the cleaned and dried substrate using a soaked sponge in one or more application processes.
  • application of the subsequent layers is within approximately thirty seconds such that the total wet thickness of the applied adhesion promoter composition is in the range of 100 nanometers or less, such as from 20 to 50 nanometers, corresponding to an applied monolayer of the adhesion promoter composition.
  • the applied adhesion promoter composition is cured to form the adhesion promoter layer disposed on the substrate.
  • the curing process includes wherein the applied adhesion promoter composition is allowed to air dry at room temperature for at least 5 seconds, such as 20 to 40 seconds, such as 25 seconds. While there is no upper limit to the time for allowing the applied adhesion promoter composition to cure, it is preferred that the curing process extends no more than about a minute prior to the application of the topcoat composition.
  • the resultant cured layer of the adhesion promoter composition has a dry layer thickness in the range of 100 nanometers or less, such as from 20 to 50 nanometers, and the lower limit is the dry thickness of a monomolecular layer of the adhesion promoter composition and is preferred.
  • the method continues by applying the topcoat composition onto the formed adhesion promoter layer and/or onto portions of the cleaned substrate not including the applied adhesion promoter composition layer.
  • the method of application may be the same or different as the application of the adhesion promoter composition, and may include applying the topcoat composition by a spray application, a dipping application, a wiping application, or the like.
  • a wiping application is used, wherein the topcoat composition is applied using a soaked sponge in one or more application processes.
  • the applied topcoat composition is cured to form a topcoat layer disposed on the formed adhesion promoter layer and/or onto portions of the cleaned substrate.
  • the curing process is cured at ambient temperatures or higher and relatively high relative humidity for a sufficient period of time to ensure that the topcoat layer is dry and adhered to the cured adhesion promoter layer and/or substrate.
  • the topcoat composition is cured for about 30 to 120 minutes, such as about 45 minutes, at a temperature between 60 and 80 degrees Fahrenheit (i.e., about 15-30 degrees Celsius) at a relative humidity of at least 50%, such as from 50 to 90%, such as from 60 to 80%.
  • the thickness of the cured topcoat composition forming the topcoat layer is not particularly limited.
  • a dry thickness of the formed topcoat layer is at most 100 nanometers, such as at most 50 nanometers, such as from 20 to 50 nanometers, and the lower limit is the dry thickness of a monomolecular topcoat layer and is preferred.
  • the produced treated substrate may be cleaned using a solvent such as isopropyl alcohol or acetone. More specifically, an outer surface of the formed topcoat layer may be wiped with the solvent.
  • the treated substrates produced in accordance with the method described above, provide excellent initial hydrophobic properties, and corresponding water repellent properties, and such treated substrates retain such hydrophobic and water repellent properties under a wide variety of test conditions intended to simulate environmental conditions, thereby confirming the durability properties of the treated substrate, which is surprising and unexpected.
  • the treated substrate has an initial water contact angle of 95 degrees or more, and preferably above 100 degrees, such as from 100 to 115 degrees, with the water contact angle being measured in accordance with ASTM D7334-08 (2013).
  • an outer surface of the treated substrate has the initial water contact angles as described above.
  • Such water contact angle properties are an indication that the treated substrate has the desired hydrophobic properties, and also has water repellent properties.
  • the treated substrate has a sliding angle of less than or equal to 30 degrees, such as from 10 to 20 degrees, as also measured by ASTM D7334-08 (2013).
  • an outer surface of the treated substrate has the initial sliding angle as described above.
  • slide angle properties are another indication that the treated substrate has the desired hydrophobic properties, and also has water repellent properties.
  • the treated substrate substantially retains its water contact angle properties after various environmental tests, including mechanical durability (Flannel 1500 or 3000 testing), Xenon weatherometer testing, hot water testing, chemical strength testing, high temperature high humidity testing (HTHH), and salt spray (a description of each of these tests is described below).
  • the treated substrate maintains its water contact angles at above 80 degrees after each of such various environmental tests.
  • the water contact angle as measured in accordance with ASTM D7334-08 (2013) is below 80 degrees, the treated substrate loses its hydrophobic and water repellent properties.
  • the treated substrate of the subject invention may be used as an article for a transport equipment in the transportation industry.
  • the article for a transport equipment may, for example, be a body of e.g. an electric train, an automobile, a ship or an aircraft, window glass (front glass, side glass or rear glass), a mirror or a bumper. Due to its hydrophobic properties, the treated substrate has an excellent water droplet removal property (i.e., water repellent properties), whereby deposition of water droplets on the surface of the topcoat layer is scarce, and deposited water droplets will be quickly repelled.
  • water droplet removal property i.e., water repellent properties
  • deposited water droplets swiftly move on the surface and will not stay as water droplets. Thus, adverse effects caused by water droplets can be eliminated.
  • the treated substrate of the subject invention may be utilized as window glass for a vehicle such as an automobile or truck.
  • the treated substrate of the subject invention may be utilized as side window glass for a vehicle such as an automobile or truck.
  • the treated substrates also are also substantially transparent, with the term “substantially transparent” used in the same manner as described above with respect to the substrate 14 prior to the application of the layers as described above.
  • water droplets tend to be hardly frozen to the treated substrate, and even if frozen, thawing is very fast.
  • deposition of water droplets on the treated substrate is scarce, whereby the number of cleaning operations of the treated substrate can be reduced, and yet, cleaning operations of the treated substrates can easily be carried out.
  • adhesion promoter compositions and topcoat compositions were applied to a glass substrate material, including adhesion promoter compositions and topcoat compositions (WRC) of the subject invention, with the resultant treated substrates evaluated for initial water contact angle and for water contact angle after the performance of various environmental and/or physical tests.
  • WRC adhesion promoter compositions and topcoat compositions
  • the water resistant topcoat (WRC) coating composition for use in forming the topcoat layer is formed, with the components as shown in Table 1, by introducing 80 parts by weight of a 7.5/92.5 weight percent mixture of a fluorine-containing chlorosilane compound (i.e., a fluorinated organic silicon compound having no etheric oxygen atom corresponding to compound (A) above) and hydrofluoroether (AE3000, manufactured by Asahi Glass Company, Limited) to a container. The mixture is stirred using a magnetic stirrer.
  • a fluorine-containing chlorosilane compound i.e., a fluorinated organic silicon compound having no etheric oxygen atom corresponding to compound (A) above
  • hydrofluoroether AE3000, manufactured by Asahi Glass Company, Limited
  • the adhesion promotor composition is formed according to the process illustrated and described in Table 2.
  • the adhesion promoter composition listed in Sequence 1 refers to the polyhedral oligomeric silsesquioxane according to the formula: C 170 H 402 O 99 Si 45 , which is used to form the Adhesion Promoter Composition 1.
  • Adhesion Promoter Composition 1 Sequence Process Step 1 Add 1 gram of concentrated polyhedral oligomeric silsesquioxane into a vial. 2 Add 10 mL (milliliters) of Ethanol (EtOH) to the vial and shake for 2 minutes. Transfer to a container. 3 Rinse the vial with 10 mL of EtOH and pour into ajar. Repeat this step until all of the solids are transferred to the jar. 4 Fill the jar with EtOH to a volume of 500 mL. Shake or agitate the jar until all solids are dissolved. 5 Add 3.75 mL of Nitric Acid to the 500 mL jar. 6 Tighten the cap on the jar and shake the jar vigorously for 3 minutes to form the Adhesion Promoter Composition 1. Use within 2 hours.
  • EtOH Ethanol
  • Adhesion Promoter Composition 2 wherein Sequence 1 substitutes the linear organosilane polymer according to the formula: C 64 H 52 O 36 Si 16 for the polyhedral oligomeric silsesquioxane according to the formula: C 170 H 402 O 99 Si 45 .
  • Triethoxyvinylsilane (11 g, 0.058 mol) was dissolved in 30 mL of EtOH at room temperature followed by the addition of 2.0 ml of aqueous KOH solution (10 mg/ml). The reaction mixture was stirred for overnight at RT. The next day a white precipitate was filtered off and dried in-vacuo to provide 2.3 g of white solid. (51%).
  • Phosphonatoethyltriethoxysilane (5.12 g, 15.59 mmol) was dissolved in 10 mL of EtOH at room temperature followed by the addition of 2.0 ml of aqueous KOH solution (10 mg/ml). The reaction mixture was stirred for overnight at RT. The next day, the solution was extracted with ethylacetate. Organic layer was dried over Na 2 SO 4 and dried in-vacuo to provide 2.39 g of liquid (1.54 mmol, Yield 79%). Obtained liquid were dissolved in a mixture of 10 ml of ethanol and water. Then, 3 ml of HCl was added to the reaction mixture and refluxed for overnight. The solution was filtered through silica to remove excess starting material. The organic filtrate is dried in-vacuo. Obtained liquid. Yield: 1.09 g (8.47 mmol, 55%).
  • Vinyltriethoxysilane (10 g, 52.5 mmol), THE (50 ml), distilled water (1 g), and sodium hydroxide (0.79 g, 19.8 mmol) are charged into a four-necked flask equipped with a reflux condenser and a thermometer at 70° C. for 5 h with magnetically stirring. The system is allowed to get cool to room temperature and left for 15 h. The volatile components are removed by heating at 95° C. under atmospheric pressure to obtain a white precipitate, which is collected by a membrane filter having a pore diameter of 0.5 ⁇ m, washed with THF, and dried at 80° C. for 3 h in a vacuum oven to yield hepta(vinyl)-tricycloheptasiloxane trisodium silanolate.
  • Hepta(vinyl)-tricycloheptasiloxane trisodium silanolate (2.2 g, 3.40 mmol), triethylamine (0.35 g, 3.45 mmol) and dry THE (50 ml) are charged into a round-bottomed flask, to which 1,2-bis(trichlorosilyl)ethane (0.50 g, 1.1 mmol) is quickly added at room temperature.
  • the mixture is magnetically stirred for 4 h at room temperature.
  • the resultant precipitate is removed by filtration, and the filtrate is concentrated by a rotary evaporator to obtain a crude product.
  • the resultant solid is dispersed in methanol, collected with a membrane filter, and dried at 75° C. for 5 h to yield 1,2-bis(heptavinyladhesion promoters)ethane as a white solid.
  • 1,2-bis(heptavinyladhesion promoters) (2 g, 1.61 mmol) and triethoxysilane (3.7 g, 22.58 mol) in toluene (50 ml) are charged into a round-bottomed flask.
  • the reaction mixture is stirred at 40° C. for 30 minutes under Ar(g) purging.
  • the catalytic amount of Pt (0) is added to the reaction mixture and heated up to 80° C. for 8 hours.
  • the solution is filtered through Celite to remove unreacted reactant.
  • the organic filtrate is dried in-vacuo to yield 1,2-bis(hepta(triethoxysilyl)adhesion promoters)ethane as pale yellow oil.
  • Vinyltriethoxysilane (10 g, 52.5 mmol), THE (50 ml), distilled water (1 g), and sodium hydroxide (0.79 g, 19.8 mmol) are charged into a four-necked flask equipped with a reflux condenser and a thermometer at 70° C. for 5 h with magnetically stirring. The system is allowed to get cool to room temperature and left for 15 h. The volatile components are removed by heating at 95° C. under atmospheric pressure to obtain a white precipitate, which is collected by a membrane filter having a pore diameter of 0.5 ⁇ m, washed with THF, and dried at 80° C. for 3 h in a vacuum oven to yield hepta(vinyl)-tricycloheptasiloxane trisodium silanolate.
  • Hepta(vinyl)-tricycloheptasiloxane trisodium silanolate (2.2 g, 3.40 mmol), triethylamine (0.35 g, 3.45 mmol) and dry THE (50 ml) are charged into a round-bottomed flask, to which 1,1,2-tris(trichlorosilyl)ethane (0.47 g, 1.1 mmol) is quickly added at room temperature.
  • the mixture is magnetically stirred for 4 h at room temperature.
  • the resultant precipitate is removed by filtration, and the filtrate is concentrated by a rotary evaporator to obtain a crude product.
  • the resultant solid is dispersed in methanol, collected with a membrane filter, and dried at 75° C. for 5 h to yield 1,1,2-tris(heptavinyladhesion promoters)ethane as a white solid.
  • 1,1,2-tris(heptavinyladhesion promoters) (1 g, 1.54 mmol) and triethoxysilane (5.33 g, 32.46 mol) in toluene (50 ml) are charged into a round-bottomed flask.
  • the reaction mixture is stirred at 40° C. for 30 minutes under Ar(g) purging.
  • the catalytic amount of Pt (0) is added to the reaction mixture and heated up to 80° C. for 8 hours.
  • the solution is filtered through Celite to remove unreacted reactant.
  • the organic filtrate is dried in-vacuo to yield 1,1,2-tris(hepta(triethoxysilyl)adhesion promoters)ethane as pale yellow oil.
  • 2-(divinylmethylsilyl)ethyltriethoxysilane (10 g, 34.65 mmol), THF (50 ml), distilled water (1 g), and sodium hydroxide (0.79 g, 19.8 mmol) are charged into a four-necked flask equipped with a reflux condenser and a thermometer at 70° C. for 5 h with magnetically stirring. The system is allowed to get cool to room temperature and left for 15 h. The volatile components are removed by heating at 95° C. under atmospheric pressure to obtain a white precipitate, which is collected by a membrane filter having a pore diameter of 0.5 ⁇ m, washed with THF, and dried at 80° C. for 3 h in a vacuum oven to yield hepta(2-(divinylmethylsilyl)ethyl)-tricycloheptasiloxane trisodium silanolate.
  • Hepta(2-(divinylmethylsilyl)ethyl)-tricycloheptasiloxane trisodium silanolate (5 g, 3.74 mmol), triethylamine (0.38 g, 3.75 mmol) and dry THF (60 ml) are charged into a round-bottomed flask, to which 1,1,2-tris(trichlorosilyl)ethane (0.51 g, 1.18 mmol) is quickly added at room temperature.
  • the mixture is magnetically stirred for 4 h at room temperature.
  • the resultant precipitate is removed by filtration, and the filtrate is concentrated by a rotary evaporator to obtain a crude product.
  • the resultant solid is dispersed in methanol, collected with a membrane filter, and dried at 75° C. for 5 h to yield 1,1,2-tris(hepta((divinylmethylsilyl)ethyl)adhesion promoters)ethane as a white solid.
  • 1,1,2-tris(hepta((divinylmethylsilyl)ethyl)adhesion promoters)ethane (1 g, 0.75 mmol) and triethoxysilane (5.17 g, 31.5 mol) in toluene (50 ml) are charged into a round-bottomed flask.
  • the reaction mixture is stirred at 40° C. for 30 minutes under Ar(g) purging.
  • the catalytic amount of Pt (0) is added to the reaction mixture and heated up to 80° C. for 8 hours.
  • the solution is filtered through Celite to remove unreacted reactant.
  • the organic filtrate is dried in-vacuo to yield 1,1,2-tris(hepta((di(triethoxysilyl)methylsilyl)ethyl)adhesion promoters)ethane as pale yellow oil.
  • 3-Isocyanatoppropyltriethoxysilane (10 g, 40.42 mmol), THE (50 ml), distilled water (1 g), and sodium hydroxide (0.8 g, 20 mmol) are charged into a four-necked flask equipped with a reflux condenser and a thermometer at 70° C. for 5 h with magnetically stirring. The system is allowed to get cool to room temperature and left for 15 h. The volatile components are removed by heating at 95° C. under atmospheric pressure to obtain a white precipitate, which is collected by a membrane filter having a pore diameter of 0.5 ⁇ m, washed with THF, and dried at 80° C. for 3 h in a vacuum oven to yield hepta(3-isocayanatopropyl)-tricycloheptasiloxane trisodium silanolate.
  • 3-Isocyanatoppropyltriethoxysilane (10 g, 40.42 mmol), THE (50 ml), distilled water (1 g), and sodium hydroxide (0.8 g, 20 mmol) are charged into a four-necked flask equipped with a reflux condenser and a thermometer at 70° C. for 5 h with magnetically stirring. The system is allowed to get cool to room temperature and left for 15 h. The volatile components are removed by heating at 95° C. under atmospheric pressure to obtain a white precipitate, which is collected by a membrane filter having a pore diameter of 0.5 ⁇ m, washed with THF, and dried at 80° C. for 3 h in a vacuum oven to yield hepta(3-isocayanatopropyl)-tricycloheptasiloxane trisodium silanolate.
  • Hepta(2-(divinylmethylsilyl)ethyl)-tricycloheptasiloxane trisodium silanolate (3 g, 2.87 mmol), triethylamine (0.29 g, 2.87 mmol) and dry THF (50 ml) are charged into a round-bottomed flask, to which 1,1,2-tris(trichlorosilyl)ethane (0.41 g, 0.95 mmol) is quickly added at room temperature.
  • the mixture is magnetically stirred for 4 h at room temperature.
  • the resultant precipitate is removed by filtration, and the filtrate is concentrated by a rotary evaporator to obtain a crude product.
  • the resultant solid is dispersed in methanol, collected with a membrane filter, and dried at 75° C. for 5 h to yield 1,1,2-tris(hepta(isocyanatopropyl)adhesion promoters)ethane as a white solid.
  • 3-Propylaminotriethoxysilane (10 g, 45.17 mmol), THE (50 ml), distilled water (1 g), and sodium hydroxide (0.8 g, 20 mmol) are charged into a four-necked flask equipped with a reflux condenser and a thermometer at 70° C. for 5 h with magnetically stirring.
  • the system is allowed to get cool to room temperature and left for 15 h.
  • the volatile components are removed by heating at 95° C. under atmospheric pressure to obtain a white precipitate, which is collected by a membrane filter having a pore diameter of 0.5 ⁇ m, washed with THF, and dried at 80° C. for 3 h in a vacuum oven to yield hepta(3-aminopropyl)-tricycloheptasiloxane trisodium silanolate.
  • Hepta(3-aminopropyl)-tricycloheptasiloxane trisodium silanolate (3 g, 3.47 mmol), triethylamine (0.35 g, 3.47 mmol) and dry THE (50 ml) are charged into a round-bottomed flask, to which 1,1,2-tris(trichlorosilyl)ethane (0.47 g, 1.1 mmol) is quickly added at room temperature.
  • the mixture is magnetically stirred for 4 h at room temperature.
  • the resultant precipitate is removed by filtration, and the filtrate is concentrated by a rotary evaporator to obtain a crude product.
  • the resultant solid is dispersed in methanol, collected with a membrane filter, and dried at 75° C. for 5 h to yield 1,1,2-tris(hepta(aminopropyl)adhesion promoters)ethane as a pale yellow solid.
  • Comparative topcoat compositions that include a 5:1 blend of fluorosilane and a fluorine-containing polyhedral oligomeric silsesquioxane (F-POSS) were included for evaluation with respect to Treated Samples 2 and 3, respectively, as described below.
  • F-POSS fluorine-containing polyhedral oligomeric silsesquioxane
  • the product EnduroShield Home commercially available from PCT Global LLC of Santa Barbara, Calif. and sold at home improvement stores throughout the United States (such as Lowe's) was purchased at a local retailer and applied to the substrates as a topcoat in accordance with the instructions provided on its packaging and was included in Treated Sample 6 below.
  • the process for forming the treated substrates evaluated in the subject invention were as follows.
  • a glass substrate was obtained and cleaned with a 2% CeO 2 solution.
  • the glass substrate was then rinsed with deionized water, and dried using compressed air.
  • a first layer of an adhesion promoter composition (when utilized) was wiped onto the cleaned glass substrate using a soaked sponge. After thirty seconds, a second layer of the adhesion promoter composition was wiped onto the first layer using a soaked sponge.
  • the resultant total thickness was between 20 and 50 nanometers.
  • a topcoat composition was applied onto the layers of adhesion promoter composition, or directly onto the cleaned glass substrate in samples not including the adhesion promoter composition, using a soaked sponge.
  • the topcoat composition was then cured for 45 minutes at a temperature of between about 60 and 80 degrees Fahrenheit (about 15 to 27 degrees Celsius) at 70% relative humidity for about 45 minutes.
  • the formed treated substrates were cleaned using a solvent such as isopropyl alcohol or acetone.
  • the treated substrates formed in accordance with the procedures described above, were first evaluated for initial water contact angle using ASTM standard D7334-08 (2013). Next the treated substrates were subjected to the following further environmental testing conditions (see Table 3 below), and then the conditioned substrates were reevaluated for water contact angle in the manner described above for the initial water contact angle.
  • treated substrates formed that includes layers of Adhesion promoter composition (1 or 2) and topcoat composition in accordance with the embodiments of the subject invention provided initial water contact angles indicative of the treated substrate having the desired hydrophobic properties, and most closely retained their initial water contact angle measurements over the variety of testing conditions than the other combinations of adhesion promoter compositions and/or topcoat compositions which confirms the durability of the applied layers to maintain such hydrophobic properties.

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US16/640,187 2017-08-24 2018-08-24 Treated substrate having hydrophobic and durability properties Abandoned US20200361191A1 (en)

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WO2021188536A2 (en) * 2020-03-16 2021-09-23 Nbd Nanotechnologies Inc. Adhesion promoters and related methods
WO2022216807A1 (en) * 2021-04-08 2022-10-13 Corning Incorporated Coated articles, methods of making coated articles, and methods of making compositions
CN119072483A (zh) * 2022-03-24 2024-12-03 Ａｇｃ株式会社 化合物、组合物、表面处理剂、物品和物品的制造方法
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Family Cites Families (18)

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Publication number Priority date Publication date Assignee Title
US5008349A (en) * 1989-10-26 1991-04-16 Dow Corning Corporation Silicone primer compositions
US6140445A (en) * 1998-04-17 2000-10-31 Crompton Corporation Silane functional oligomer
JP5076257B2 (ja) * 2001-02-01 2012-11-21 旭硝子株式会社 撥水性組成物、表面処理された基材、その製造方法および輸送機器用物品
US20040034143A1 (en) * 2001-05-17 2004-02-19 James Hubert Plastisol composition and method for using same
US6753087B2 (en) * 2001-05-21 2004-06-22 3M Innovative Properties Company Fluoropolymer bonding
BRPI0409044A (pt) 2003-03-21 2006-03-28 Du Pont composições de revestimento, substrato revestido, processos de aplicação e processo para o reacabamento de um revestimento danificado
US7344783B2 (en) 2003-07-09 2008-03-18 Shell Oil Company Durable hydrophobic surface coatings using silicone resins
CA2708101A1 (en) * 2007-12-20 2009-07-09 E. I. Dupont De Nemours And Company Process for producing a multilayer coating
JP5124496B2 (ja) 2008-02-01 2013-01-23 富士フイルム株式会社 親水性部材
WO2011016458A1 (ja) * 2009-08-03 2011-02-10 旭硝子株式会社 撥水膜形成用組成物、撥水膜付き基体およびその製造方法並びに輸送機器用物品
JP2012041586A (ja) 2010-08-17 2012-03-01 Shin-Etsu Chemical Co Ltd 金属表面処理剤、表面処理鋼材及びその処理方法、並びに塗装鋼材及びその製造方法
US9153357B1 (en) * 2014-03-27 2015-10-06 Rohm And Haas Electronic Materials Llc Adhesion promoter
WO2016049269A1 (en) * 2014-09-24 2016-03-31 Nbd Nanotechnologies, Inc. F-poss coatings and additives and methods of making same
EP3241060B1 (en) * 2014-12-30 2019-11-06 Essilor International Uv curable coating compositions for improved abrasion resistance
US10106643B2 (en) * 2015-03-31 2018-10-23 3M Innovative Properties Company Dual-cure nanostructure transfer film
US10450469B2 (en) 2015-06-09 2019-10-22 Nbd Nanotechnologies, Inc. Transparent self-healing oleophobic and hydrophobic coatings
CN109153767B (zh) * 2016-05-24 2021-09-24 巴斯夫涂料有限公司 涂覆剂和由其制备的具有改进抗污性和清洁性的涂层及其用途
CN107012456B (zh) * 2017-04-17 2019-06-28 武汉大学 一种烷氧基硅乙基多面体齐聚硅倍半氧烷改性的金属表面前处理剂及其制备方法、应用

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