WO2025006028A1 - Composition adhésive - Google Patents

Composition adhésive Download PDF

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Publication number
WO2025006028A1
WO2025006028A1 PCT/US2024/023836 US2024023836W WO2025006028A1 WO 2025006028 A1 WO2025006028 A1 WO 2025006028A1 US 2024023836 W US2024023836 W US 2024023836W WO 2025006028 A1 WO2025006028 A1 WO 2025006028A1
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WO
WIPO (PCT)
Prior art keywords
adhesive composition
acrylic
substrate
acrylate
rheology modifier
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/US2024/023836
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English (en)
Inventor
Jie Wu
Yushan Hu
Yinzhong Guo
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 Global Technologies LLC
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Dow Global Technologies LLC
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Filing date
Publication date
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Publication of WO2025006028A1 publication Critical patent/WO2025006028A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/064—Copolymers with monomers not covered by C09J133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
    • 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
    • B32B21/00—Layered products comprising a layer of wood, e.g. wood board, veneer, wood particle board
    • B32B21/04—Layered products comprising a layer of wood, e.g. wood board, veneer, wood particle board comprising wood as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B21/08—Layered products comprising a layer of wood, e.g. wood board, veneer, wood particle board comprising wood as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/304—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising vinyl halide (co)polymers, e.g. PVC, PVDC, PVF, PVDF
    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/308—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)polymers
    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
    • 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
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
    • C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/348—Hydroxycarboxylic acids
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group

Definitions

  • roofing membrane is a sheet-like structure, usually single-ply, with moisture barrier properties and is composed of a polymeric material such as ethylene-propylene-diene terpolymer (EPDM), butyl rubber, neoprene, polyvinyl chloride (PVC), chlorinated polyethylene, thermoplastic polyolefin (TPO) and/or modified bitumen/asphalt.
  • EPDM ethylene-propylene-diene terpolymer
  • PVC polyvinyl chloride
  • TPO thermoplastic polyolefin
  • roofing membrane is typically overlapped and/or spliced together with an adhesive to form a continuous, water-tight sheet for covering a roof area.
  • An adhesive composition is by way of an adhesive composition.
  • Adhesive composition finds favor as the adherent for roofing membrane (as opposed to rivets or fusion bonds, for example), because adhesive composition is easy to apply as a continuous layer, and adhesive composition provides even, and uniform adhesion compared to rivets or fusion bonds which provide point bonding.
  • the adhesive composition requires appropriate bond strength to adhere the roofing membrane to other industrial substrates such as steel, wood, concrete, roof boards, and insulation.
  • roofing membrane is exposed to stresses such as roof movement, heavy winds, freeze-thaw cycles and thermal cycles, so too must the adhesive composition be resilient and capable to withstand these same stresses.
  • conventional adhesive composition for roofing membrane is typically solvent-based and utilizes organic solvents such as toluene and xylene. Use of these solvents poses environmental, health and fire hazards, making solvent-based adhesive compositions undesirable.
  • the present disclosure provides a composition.
  • the composition is an adhesive composition.
  • the adhesive composition includes an acrylic emulsion, a polyurethane dispersion, a tackifier, and a rheology modifier.
  • the laminate structure includes a first substrate and a second substrate.
  • An adhesive composition is disposed between the first substrate and the second substrate.
  • the adhesive composition is composed of an acrylic emulsion, a polyurethane dispersion, a tackifier, and a rheology modifier.
  • the first substrate and the second substrate are selected from roof substrate and/or roofing membrane.
  • the numerical ranges disclosed herein include all values from, and including, the lower and upper value.
  • ranges containing explicit values e.g., 1 or 2, or 3 to 5, or 6, or 7
  • any subrange between any two explicit values is included (e.g., the range 1-7 above includes subranges of from 1 to 2; from 2 to 6; from 5 to 7; from 3 to 7; from 5 to 6; etc.).
  • an "acrylic-based monomer,” as used herein, is a monomer containing the Structure (A) below: Structure (A) wherein Ri is H or a Ci-Cis alkyl group, and R2 is H or CH3.
  • Acrylic-based monomers include acrylic acid, methacrylic acid, acrylates, and methacrylates.
  • blend or "polymer blend,” as used herein, is a blend of two or more polymers. Such a blend may or may not be miscible (not phase separated at molecular level). Such a blend may or may not be phase separated. Such a blend may or may not contain one or more domain configurations, as determined from transmission electron spectroscopy, light scattering, x-ray scattering, and other methods known in the art.
  • composition refers to a mixture of materials which comprise the composition, as well as reaction products and decomposition products formed from the materials of the composition.
  • compositions claimed through use of the term “comprising” may include any additional additive, adjuvant, or compound, whether polymeric or otherwise, unless stated to the contrary.
  • the term “consisting essentially of” excludes from the scope of any succeeding recitation any other component, step, or procedure, excepting those that are not essential to operability.
  • the term “consisting of” excludes any component, step, or procedure not specifically delineated or listed.
  • An "olefin-based polymer” or “polyolefin” is a polymer that contains more than 50 weight percent polymerized olefin monomer (based on total amount of polymerizable monomers), and optionally, may contain at least one comonomer.
  • a nonlimiting example of an olefin-based polymer is ethylene-based polymer.
  • a "polymer” is a compound prepared by polymerizing monomers, whether of the same or a different type, that in polymerized form provide the multiple and/or repeating "units" or "mer units” that make up a polymer.
  • polymer thus embraces the term homopolymer, usually employed to refer to polymers prepared from only one type of monomer, and the term copolymer, usually employed to refer to polymers prepared from at least two types of monomers. It also embraces all forms of copolymer, e.g., random, block, etc.
  • ethylene/a-olefin polymer and "propylene/a-olefin polymer” are indicative of copolymer as described above prepared from polymerizing ethylene or propylene respectively and one or more additional, polymerizable a-olefin monomer.
  • polymers are often referred to as being "made of” one or more specified monomers, "based on” a specified monomer or monomer type, “containing” a specified monomer content, or the like, in this context the term “monomer” is understood to be referring to the polymerized remnant of the specified monomer and not to the unpolymerized species.
  • polymers herein are referred to as being based on “units” that are the polymerized form of a corresponding monomer.
  • 90° peel test 90° peel test was conducted with an Instron Peel Text Fixture (INSTRON 5566). Test speed is 2 in/min.
  • Emulsion or dispersion viscosity was measured using a Brookfield Viscometer Model, and a Brookfield RV-DV-ll-Pro viscometer spindle #27, at 25°C. The sample was poured into a cup and enough volume was poured in, such that when the viscometer apparatus was lowered, the spindle was completely submerged into the dispersion. The viscometer was turned on and set to operate at a shear rate from 1 to 10 rounds per minute (rpm) to ensure torque is within 100%. Readings were monitored for 15 minutes, or until the values stabilized, at which point, a final reading was recorded.
  • rpm rounds per minute
  • the present disclosure provides an adhesive composition.
  • the adhesive composition includes an acrylic emulsion, a polyurethane dispersion, a tackifier, and a rheology modifier.
  • the present adhesive composition includes the acrylic emulsion.
  • the acrylic emulsion is a water-based acrylic dispersion (interchangeably referred to as "acrylic emulsion").
  • water-based acrylic dispersion is a composition wherein water is the continuous phase, i.e., a composition having an aqueous medium.
  • the acrylic dispersion (acrylic emulsion) is formed by the polymerization of one or more acrylic-based monomers and optionally other unsaturated monomers.
  • suitable polymerization procedures include emulsion polymerization, mini emulsion polymerization, micro-emulsion polymerization, or suspension polymerization processes where the solvent is water.
  • the water-based acrylic emulsion (interchangeably referred to as "acrylic dispersion”) includes one or more acrylic-based monomers (and optionally one or more other unsaturated monomers), a surfactant, an initiator, a neutralizer, and water, optionally to the exclusion of an ethylene-based polymer.
  • acrylic-based monomers and optionally one or more other unsaturated monomers
  • surfactant an initiator
  • neutralizer e.g., ethylene-based polyethylene-based polymer
  • water optionally to the exclusion of an ethylene-based polymer.
  • (meth) followed by another term such as acrylate refers to both acrylates and methacrylates.
  • (meth)acrylate refers to either acrylate or methacrylate
  • (meth)acrylic refers to either acrylic or methacrylic
  • (meth)acrylic acid refers to either acrylic acid or methacrylic acid
  • (meth)acrylamide refers to either acrylamide or methacrylamide.
  • Nonlimiting examples of suitable acrylic-based monomers include Ci-Ci9-alkyl (meth)acrylates, for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, n-octyl (meth)acrylate, n-decyl (meth)acrylate, n-dodecyl (meth)acrylate (i.e., lauryl (meth)acrylate), tetradecyl (meth)acrylate, oleyl (meth)acrylate, palmityl (meth)acrylate, stearyl (meth)acrylate, isobornyl (meth)acrylate, benzyl (meth)acrylate, (meth)acrylic acid, butyl acrylate (BA), ethylhexyl acryl
  • One or more other unsaturated monomers may be polymerized with the acrylicbased monomer(s).
  • suitable "other unsaturated monomers” include 2-hydroxyethyl acrylate (2-HEA), 2-hydroxylethyl methacrylate (2-HEMA), styrene (STY), acrylonitrile (AN), vinyl ester, vinyl acetate, unsaturated carboxylic acid, monomethyacryloylethyl phosphate (PEM), allyl phthalate, and combinations thereof.
  • Nonlimiting examples of suitable unsaturated carboxylic acid include itaconic acid, fumaric acid, citraconic acid, sorbic acid, cinnamic acid, glutaconic acid and maleic acid; monoethylenically unsaturated carboxylic anhydride, such as itaconic acid anhydride, fumaric acid anhydride, citraconic acid anhydride, sorbic acid anhydride, cinnamic acid anhydride, glutaconic acid anhydride and maleic acid anhydride; monoethylenically unsaturated amides, such as N-alkylolamides, such as (meth)acrylamide, methylol (meth)acrylamide, 2- hydroxyethyl (meth)acrylamide; and hydroxyalkyl esters of monoethylenically unsaturated carboxylic acids, such as hydroxyethyl (meth)acrylate and hydroxypropyl (meth)acrylate and combinations thereof.
  • the acrylic dispersion includes a surfactant.
  • suitable surfactant include cationic surfactants, anionic surfactants, zwitterionic surfactants, non-ionic surfactants, and combinations thereof.
  • the surfactant can be an anionic surfactant and/or a nonionic surfactant such as, for example, alkali metal or ammonium salts of alkyl, aryl, or alkylaryl sulfates, sulfonates or phosphates; alkyl sulfonic acids; fatty acids; ethylenically unsaturated surfactant monomers; ethoxylated alcohols or phenols, and sodium vinyl sulfonate.
  • the surfactant is sodium lauryl sulfate (SLS).
  • the acrylic dispersion includes a neutralizer.
  • the neutralizer serves two purposes. It improves colloidal stability by ionic repulsive interactions of deprotonated (meth)acrylic acid moieties. It also provides a way to improve the solubility of the post-additive ethoxylated phosphate ester surfactants.
  • Nonlimiting examples of suitable neutralizer include NaOH, KOH, NH4OH, Borax, NaHCO 3 , KHCO 3 , Na 2 CO 3 , K 2 CO 3 , Na 2 HPO 4 , K 2 HPO 4 , Na 2 B 4 O 7 , and organoamines (alkylamines, alkanolamines) such as methylamine, ethylamine, isopropylamine, n-butylamine, n-hexylamine, n-octylamine, 2-ethylhexylamine, diethylamine, di-n-butylamine, diisopropylamine, triethylamine, tri-n-butylamine, benzylamine, 2-phenyl- ethylamine, 2-amino-2-methyl-l-propanol, monoethanolamine, diethanolamine, triethanolamine, isopropanolamine, N-methylethanolamine, N-methyldiethanolamine, N,N
  • the surfactant acts as an emulsifier and enables droplets of the acrylic-based monomer (and optional other unsaturated monomer), which is hydrophobic, to form throughout the aqueous medium.
  • An initiator is then introduced into the emulsified mixture. The initiator reacts with the acrylic-based monomer(s) (and optional other unsaturated monomer) dispersed throughout the aqueous medium until all, or substantially all, of the acrylic-based monomer(s) (and optional other unsaturated monomer) is/are polymerized.
  • the end result is an acrylic dispersion composed of a dispersion of acrylic-based polymer particles in the aqueous medium, the acrylic-based polymer particles composed of one or more acrylic-based monomer subunits (and optional other unsaturated monomer) to the exclusion of ethylene-based polymer.
  • a neutralizer is added to adjust the pH of the resulting acrylic-based polymer particles to the desired pH range.
  • the neutralizer also serves to solubilize any post-additive surfactant.
  • the acrylic dispersion may optionally include a defoamer, a wetting agent, a rheology modifier, and any combination thereof.
  • the acrylic dispersion includes a crosslinking monomer.
  • suitable crosslinking monomer include allyl acrylate, allyl methacrylate, di-allyl phthalate, N-methylol acrylamide, and any combination thereof.
  • the acrylic dispersion optionally includes one or more additives.
  • suitable additives include defoamers, rheology modifiers, solvents, coalescing agents, biocides, preservatives, and combinations thereof.
  • Commercially available defoamers include, but are not limited to, Tego Antifoam 2291, Foamaster MO S090, Tego Antifoam KS 53, Tego Antifoam 2450, Tego Antifoam D 2315, BYK Oil, and Fluxair A-97.
  • the acrylic dispersion includes an acrylic-based polymer composed of one or more acrylic-based monomers selected from butyl acrylate (BA), ethylhexyl acrylate (2-EHA), ethyl acrylate (EA), methyl acrylate (MA), butyl methyacrylate (BMA), and combinations thereof, an unsaturated monomer selected from 2-hydroxyethyl acrylate (2-HEA), 2- hydroxylethyl methacrylate (2-HEMA), styrene (STY), acrylonitrile (AN), vinyl ester, vinyl acetate, methacrylic acid, acrylic acid, itaconic acid, allyl acrylate, allyl phthalate, and combinations thereof, and a surfactant that is sodium vinyl sulfonate.
  • BA butyl acrylate
  • EHA ethylhexyl acrylate
  • EA ethyl acrylate
  • MA methyl acrylate
  • BMA butyl me
  • the acrylic dispersion includes an acrylic-based polymer composed of
  • a surfactant that is sodium vinyl sulfonate, wherein (a), (b), (c), and (d) amount to 100 dry wt% of the acrylic-based polymer and weight percent is based on total dry weight of the acrylic-based polymer.
  • the present adhesive composition includes the polyurethane dispersion.
  • the polyurethane dispersion includes polyurethane particles dispersed in water.
  • the waterborne polyurethane dispersion is derived from, or otherwise formed from, a system composed of (A) an isocyanate component with two or more isocyanate groups and (B) a polyol component.
  • the particles for the polyurethane dispersion are composed of polyurethane having an isocyanate component (A).
  • the isocyanate component is a polyisocyanate compound with at least two isocyanate groups.
  • the isocyanate component can be an aromatic polyisocyanate, an aliphatic polyisocyanate, a cycloaliphatic polyisocyanate, an araliphatic polyisocyanate, and any combination thereof.
  • the aromatic polyisocyante can be a Ce-Cis aromatic polyisocyanate with at least two isocyanate groups.
  • the aliphatic polyisocyanate can be a C4-C12 aliphatic polyisocyanate with at least two isocyanate groups.
  • the cycloaliphatic polyisocaynate can be a Ce-Cis cycloaliphatic polyisocyanates with at least two isocyanate groups.
  • the araliphatic polyisocaynate can be a C7-C15 araliphatic polyisocyanate with at least two isocyanate groups.
  • Nonlimiting examples of suitable isocyanate component include m-phenylene diisocyanate, 2,4-toluene diisocyanate and/or 2,6-toluene diisocyanate (TDI), the various isomers of diphenylmethanediisocyanate (MDI), carbodiimide modified MDI products, hexamethylene-l,6-diisocyanate, tetramethylene-l,4-diisocyanate, cyclohexane- 1,4-diisocyanate, hexahydrotoluene diisocyanate, hydrogenated MDI, naphthylene-1,5- diisocyanate, isophorone diisocyanate (I PDI), or mixtures thereof.
  • the isocyanate component (A) has an average functionality from 2 to 10, or from 2 to 8, or from 2 to 6.
  • the polyisocyanate component is an isocyanate prepolymer.
  • the isocyanate prepolymer is obtained by, or otherwise formed from reacting one or more polyisocyanates stated above with one or more isocyanate-reactive components.
  • the isocyanate-reactive compononent can be a C2-C16 aliphatic polyhydric alcohol with at least two hydroxy groups, a C6-C15 cycloaliphatic polyhydric alcohol with at least two hydroxyl groups, a C6-C15 aromatic polyhydric alcohols with at least two hydroxy groups, a C7-C15 araliphatic polyhydric alcohol with at least two hydroxy groups, a polyester polyol, a polycarbonate diol, a polyetherdiol, a C2-C10 polyamine with at least two amino groups, a C2- C10 polythiol with at least two thiol groups, a C2-C10 alkanolamine with at least one hydroxyl group and at least one amino group, and combinations thereof, with the proviso that the isocyanate prepolymer has at least two free isocyanate terminal groups.
  • Nonlimiting examples of suitable isocyanate-reactive component include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butenediol, 1,4-butynediol, 1,5-pentanediol, neopentylglycol, bis(hydroxy-methyl) cyclohexanes such as l,4-bis(hydroxymethyl)cyclohexane, 2- methylpropane-l,3-diol, methylpentanediols, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, dibutylene glycol and polybutylene glycols.
  • Suitable prepolymers for use as the polyisocyanate component are prepolymers having NCO group contents from 2 to 40 weight percent, or from 4 to 30 weight percent. These prepolymers can be prepared by reaction of the di— and/or poly-isocyanates with materials including lower molecular weight diols and triols.
  • aromatic polyisocyanates containing urethane groups having NCO contents of from 5 to 40 weight percent, or from 20 to 35 weight percent, obtained by reaction of diisocyanates and/or polyisocyanates with, for example, lower molecular weight diols, triols, oxyalkylene glycols, dioxyalkylene glycols, or polyoxyalkylene glycols having molecular weights up to about 800.
  • diisocyanates and/or polyisocyanates with, for example, lower molecular weight diols, triols, oxyalkylene glycols, dioxyalkylene glycols, or polyoxyalkylene glycols having molecular weights up to about 800.
  • These polyols can be employed individually or in mixtures as di— and/or polyoxyalkylene glycols.
  • diethylene glycols, dipropylene glycols, polyoxyethylene glycols, ethylene glycols, propylene glycols, butylene glycols, polyoxypropylene glycols and polyoxypropylene-polyoxyethylene glycols can be used.
  • Polyester polyols can also be used, as well as alkane diols such as butane diol.
  • Other diols also useful include bishydroxyethyl— or bishydroxypropyl-bisphenol A, cyclohexane dimethanol, and bishydroxyethyl hydroquinone.
  • the particles of the polyurethane dispersion also include the polyol component (B).
  • the polyol component (B) can be a polyhydric alcohol, a polyether polyol, a polyester polyol, and any combination thereof.
  • the polyhydric alcohol can be a C2-C16 aliphatic polyhydric alcohol with at least two hydroxy groups, a C6-C15 cycloaliphatic polyhydric alcohol with at least two hydroxyl groups, a C6-C15 aromatic polyhydric alcohols with at least two hydroxy groups, a C7-C15 araliphatic polyhydric alcohol with at least two hydroxy groups.
  • Nonlimiting examples of suitable polyhydric alcohol include 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butenediol, 1,4-butynediol, 1,5- pentanediol, bis(hydroxy-methyl) cyclohexanes such as l,4-bis(hydroxymethyl)cyclohexane, 2-methylpropane-l,3-diol, methylpentanediols, and combinations thereof.
  • the polyether polyol can be an oxyalkylene glycol, a dioxyalkylene glycol, a polyoxyalkylene glycol, and combinations thereof.
  • suitable polyether glycols include diethylene glycols, dipropylene glycols, polyoxyethylene glycols, ethylene glycols, propylene glycols, butylene glycols, polyoxypropylene glycols and polyoxypropylenepolyoxyethylene glycols, and neopentyl-glycol. diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, dibutylene glycol and polybutylene glycols.
  • Nonlimiting examples of suitable polyester polyols include diacids condensation reacts with diols, the diacid can be phthalic acid, phthalic anhydride, adipic acid, succinic acid, succinic anhydride, octanedioic acid, dodecanedioic acid or their mixture, the diol can be ethylene glycol, diethylene glycol, propane diol, butane diol, hexane diol, octane diol or the a diol with 2 to 18 carbon atoms, and combinations thereof.
  • the diacid can be phthalic acid, phthalic anhydride, adipic acid, succinic acid, succinic anhydride, octanedioic acid, dodecanedioic acid or their mixture
  • the diol can be ethylene glycol, diethylene glycol, propane diol, butane diol, hexane diol, o
  • the waterborne polyurethane dispersion is prepared by (i) reacting the isocyanate component (A) with the polyol component (B) and 1,3-dimethylol propane acid to form a urethane prepolymer chain; (ii) dispersing the urethane prepolymer chain obtained in step (i) in an aqueous solvent (e.g., water) after neutralization with neutralization agent such as triethylamine and or monoethanol amine or with the presence of an emulsifier (an internal emulsifier or an external emulsifier (and optional catalyst) to form an emulsion and (iii) optionally further adding a chain extender into the emulsion to react with the urethane prepolymer chain obtained in step (i) and form the emulsified polyurethane dispersion.
  • an aqueous solvent e.g., water
  • neutralization agent such as triethylamine and or monoethanol amine
  • the emulsifier can be an anionic surfactant, a cationic surfactant, an amphoteric surfactant, a non-ionic surfactant, and combinations thereof.
  • suitable classes of surfactant include sulfates of ethoxylated phenols such as poly(oxy-l,2- ethanediyl)a-sulfo-ijo(nonylphenoxy) salt; alkali metal fatty acid salts such as alkali metal oleates and stearates; alkali metal C12-C16 alkyl sulfates such as alkali metal lauryl sulfates; amine C12-C16 alkyl sulfates such as amine lauryl sulfates, or triethanolamine lauryl sulfate; alkali metal C12-C16 alkylbenzene sulfonates such as branched and linear sodium dodecylbenzene sulfon
  • the polyurethane dispersion optionally includes one or more additives.
  • suitable additives include defoamers, rheology modifiers, solvents, coalescing agents, biocides, preservatives, and combinations thereof.
  • Commercially available defoamers include, but are not limited to, Tego Antifoam 2291, Foamaster MO S090, Tego Antifoam KS 53, Tego Antifoam 2450, Tego Antifoam D 2315, BYK Oil, and Fluxair A-97.
  • the present adhesive composition includes the tackifier.
  • the tackifier can be an aliphatic hydrocarbon resin made from the polymerization of monomers including ethylenica I ly unsaturated C4 -Cs molecules; a rosin ester and/or a rosin acid; mixed aliphatic/aromatic tackifying resins; a polyterpene; and a hydrogenated tackifying resin.
  • the hydrogenated resins also include resins formed from the polymerization and subsequent hydrogenation of a feedstock based on dicyclopentadiene; resins produced from the polymerization and subsequent hydrogenation of pure aromatic feedstocks such as styrene, alpha-methylstyrene, vinyl toluene; resins formed from the polymerization and subsequent hydrogenation of C7 - C12 aromatics; and resins produced from the polymerization and subsequent hydrogenation of aliphatic petroleum derivatives of C4 -C10 dienes and mono-olefins, such as piperylene, isoprene and 2-methyl-2-butene.
  • the tackifier is a rosin resin formed from (i) a rosin acid and/or a rosin ester obtained by esterifying the rosin acid/ester with an alcohol, an epoxy compound, a non-hydrogenated aliphatic Cs resin, a hydrogenated aliphatic Cs resin, an aromatic modified C5 resin, a terpene resin, a hydrogenated Cg resin, a (meth)acrylic resin, and combinations thereof.
  • suitable tackifier include SNOWTACK 100X, SNOWTACK 100G, and combinations thereof.
  • the present adhesive composition includes the rheology modifier.
  • the rheology modifier can be a non-ionic polyurethane; a hydrophobically modified alkali swellable emulsion (HASE) that is a polyacrylate-based polymer such as polyacrylate polymer based on a majority by monomer number percentage of acrylic acid, acrylic acid esters, vinyl acetate, methacrylic acid, acrylonitrile and mixtures thereof; a hydrophobically modified ethylene oxide urethane rheology modifier (HEUR), a hydroxyl ethyl cellulose such as hydrophobically modified hydroxyl ethyl cellulose; xanthan gum; hydrogenated castor oil (HCO) and mixtures thereof.
  • HASE hydrophobically modified alkali swellable emulsion
  • HEUR hydrophobically modified ethylene oxide urethane rheology modifier
  • HEUR hydroxyl ethyl cellulose
  • HCO hydrogenated castor oil
  • the rheology modifier is selected from a hydrophobically modified, alkali swellable emulsions (HASE) rheology modifier, a hydrophobically-modified ethylene oxide urethane (HEUR) rheology modifier, and combinations thereof.
  • HASE alkali swellable emulsions
  • HEUR hydrophobically-modified ethylene oxide urethane
  • One or more optional additives may be present in the adhesive composition.
  • suitable additives include defoamer, wetting agent, mechanical stabilizer, pigment, filler, freeze-thaw agent, neutralizing agent, plasticizer, adhesion promoter, and combinations thereof.
  • the adhesive composition includes a defoamer.
  • defoamer include mineral oil based defoamer, such as Airase 4500 and TEGO Antifoam 2263, FoamStar ST2410, or organo modified siloxanes, such as TEGO Antifoam D2315, TEGO Antifoam 4-88, TEGO Antifoam 1488, DOWSIL AFE-7610, XIAMETER AFE-2210, DOWSIL 112F additive, DOWSIL 62 additive, and combinations thereof.
  • mineral oil based defoamer such as Airase 4500 and TEGO Antifoam 2263, FoamStar ST2410, or organo modified siloxanes, such as TEGO Antifoam D2315, TEGO Antifoam 4-88, TEGO Antifoam 1488, DOWSIL AFE-7610, XIAMETER AFE-2210, DOWSIL 112F additive, DOWSIL 62 additive, and combinations thereof.
  • the adhesive composition comprises, or consists of
  • the adhesive composition has one, some, or all of the following properties: a pH from 7.5 to 9.5, and/or a viscosity from 15,000 cP to 200,000 cP, or from 30,000 cP to 150,000 cP.
  • the present disclosure provides a laminate structure.
  • the laminate structure includes a first substrate and a second substrate.
  • the present adhesive composition is disposed between, or is otherwise located between, the first substrate and the second substrate and forms an adhesive layer.
  • the adhesive composition is the present adhesive composition formed from the acrylic emulsion, the polyurethane dispersion, the rheology modifier, and the tackifier as previously disclosed herein.
  • the adhesive layer (composed of the present adhesive composition) may be a continuous layer or may be a discontinuous layer disposed between the first substrate and the second substrate.
  • the adhesive layer is in direct contact with the first substrate and is in direct contact with the second substrate.
  • direct contact is a configuration whereby two components, or two structures, are in physical contact with each other with no intervening layer(s) and/or no intervening material(s) and/or no intervening structure(s) located between a portion of the two contacting components.
  • the thickness of the adhesive layer is from 50 micron to 1500 microns, or from 100 micron to 800 microns.
  • the laminate structure includes the first substrate and the second substrate.
  • the first substrate and/or the second substrate can be a roof substrate or a roofing membrane.
  • a "roof substrate,” as used herein is a plywood roof substrate, a glass roof substrate, a cellulosic roof substrate, a roofing shingle, a glass mat, a fiberglass mat, an underlayment, a roof deck, a photovoltaic (PV) panel, a modified bitumen (MODBIT) substrate, a roll good, a chimney, a polyisocyanurate (ISO) foam board, a fiberglass roof board an insulation board and a cover board wherein the insulation board and/or cover board may carry a variety of facer materials including, but not limited to, paper facers, fiberglass-reinforced paper facers, fiberglass facers, coated fiberglass facers, metal facers such as aluminum facers, and solid facers such as wood, OSB and plywood, as well as gypsum or any combination thereof.
  • the roof substrate may also include the roof
  • a "roofing membrane,” as used herein, is a sheet of a flexible material having a thickness from 20 mil (0.508 mm) to 140 mil (3.556 mm), or from 30 mil (0.762 mm) to 120 mil (3.048 mm), or from 40 mil (1.016 mm) to 100 mil (2.54 mm).
  • roofing membrane when properly installed, prevents water and/or moisture from leaking into a building, a home, or other structure or dwelling.
  • roofing membrane examples include polyvinyl chloride (PVC) roofing membrane, a thermoplastic polyolefin (TPO) roofing membrane, an ethylene propylene diene monomer (EPDM) roofing membrane, chlorosulfonated polyethylene roofing membrane, asphalt-based roofing membrane such as modified asphalt membranes and/or built roof systems.
  • PVC polyvinyl chloride
  • TPO thermoplastic polyolefin
  • EPDM ethylene propylene diene monomer
  • chlorosulfonated polyethylene roofing membrane such as modified asphalt membranes and/or built roof systems.
  • the first substrate is a roof substrate
  • the second substrate is a roof substrate.
  • the second substrate can be the same roof substrate as the first substrate, or the second substrate is a roof substrate that is different than the roof substrate for the first substrate.
  • the first substrate is a roof substrate
  • the second substrate is a roofing membrane.
  • the first substrate is a roofing membrane
  • the second substrate is a roofing membrane.
  • the second substrate can be the same roofing membrane as the first substrate, or the second roofing membrane is a roofing membrane that is different than the roofing membrane for the first substrate.
  • the adhesive composition can be applied to the first substrate (substratel) and/or to the second substrate (substrate2) by way of dip and roll techniques, roller, brush, spray, and any combination thereof to prepare an adhesive-coated substrate.
  • the first substrate and/or the second substrate may or may not be subjected to a surface treatment prior to application of the present adhesion composition thereto.
  • suitable surface treatments include a primer coating, and a corona discharge treatment prior to application of the adhesive composition as a layer onto the substrate surface(s).
  • the other substrate is then placed, or otherwise positioned, on the adhesive-exposed surface of the adhesive-coated substrate.
  • a roller or a similar device, can then be applied to ensure firm contact between the adhesive composition and the other substrate, thereby forming the laminate structure with configuration: substratel (substrate2)/ present adhesive composition/substrate2 (substratel), with alternate layer configuration shown in parentheses.
  • the laminate structure is then dried and/or cured.
  • the adhesive layer for the laminate structure is the present adhesive composition formed from the acrylic emulsion, the polyurethane dispersion, the rheology modifier, and the tackifier as previously disclosed herein.
  • the laminate structure When fully dried, or otherwise fully cured, the laminate structure includes the first substrate, the second substrate, and the adhesive layer disposed between the first substrate and the second substrate, and the adhesive layer comprises, or consists of
  • the present adhesive composition does not require the use of organic solvents—that is, the present adhesive composition is solvent-free. Applicant surprisingly discovered that the present adhesive composition that is waterborne, is fast-curing and develops bond strength immediately after application to a substrate.
  • the present adhesive composition is formulated to form a bond between a roof substrate and a roofing membrane, and combinations thereof.
  • a given amount (as shown in Table 5) of the waterborne polyurethane dispersionl was added to the two-component blend under agitation to form a three-component blend and the three-component blend was mixed at 50-100 rpm for five minutes. Then, an amount (Table 5) of the solvent-free rheology modifier (ACRYSOL TT615) was slowly added in the vortex area under overhead mixing and mixed at 50-100 rpm to form a pre-mixture. The premixture pH was 6.5 and was increased to pH 8.5 by adding ammonia.
  • Adhesive composition formulations for inventive example (“IE") 1 and IE2 and comparative samples (“CS”) CS-1, CS- 2, CS-3, CS-4, CS-5 are provided in Table 5 below.
  • Dry blends consisting of the PVC powder, DIDP liquid plasticizer, and additives were first prepared using a 4L Eberbach high powered, single speed blender (Model E8010) equipped with an insulation jacket and thermocouple. The operating speed of the blender was 10,800 rpm. The temperature during blending was monitored, and the components were added according to the sequence outlined below in Table 3. After blending, the samples were transferred to Ziplock bags. [0066] Table 3
  • a Haake PolyLab Rheocord 300p Drive Unit equipped with the large Rheomix 300p bowl cart and cam rotors was used to melt mix the PVC dry blends.
  • the Haake mixer was set to a temperature of 170°C, and the rotor speed set to 20 rpm.
  • the PVC dry blend was added to the mixing bowl.
  • Elvaloy KEE plasticizer the temperature was first allowed to increase back to 170°C after the addition of the PVC dry blend.
  • Elvaloy KEE plasticizer was then added at a rate of 10 grams per every 2 - 3 minutes. After the additional of all the Elvaloy, the rotor speed was increased to 50 rpm and mixed for 10 minutes.
  • the polymer was removed from the Haake bowl and pressed into a flat patty. The samples were allowed to cool, and then transferred to a Ziplock bag.
  • the formulation in part per hundred (PHR) of PVC based membrane is shown in Table 4.
  • IE1 and IE2 demonstrated excellent adhesion performance on wood/PVC membrane laminate structure compared to the comparative samples CS-1, CS-2, CS-3, CS-4, CS-5.
  • the adhesive performance of IE1 and IE2 is better than the adhesive performance for acrylic adhesive based formula or polyurethane dispersion based adhesive.
  • IE 1 and IE2 exhibited a surprising and synergistic effect of combining acrylic and polyurethane backbone in the formulation.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)

Abstract

La présente invention concerne une composition. Dans un mode de réalisation, la composition est une composition adhésive. La composition adhésive comprend une émulsion acrylique, une dispersion de polyuréthane, un agent poisseux et un modificateur de rhéologie. La présente composition adhésive peut être une couche adhésive disposée entre un premier substrat et un second substrat de manière à former une structure stratifiée, le premier substrat et le second substrat étant choisis parmi un substrat de toit et/ou une membrane de toiture.
PCT/US2024/023836 2023-06-28 2024-04-10 Composition adhésive Ceased WO2025006028A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0798359A2 (fr) * 1996-03-19 1997-10-01 Basf Aktiengesellschaft Composition aqueuse d'adhésif de contact
JPH09302220A (ja) * 1996-05-15 1997-11-25 Dainippon Ink & Chem Inc 水性ポリウレタン樹脂組成物及び接着剤
WO2001077248A1 (fr) * 2000-04-05 2001-10-18 3M Innovative Properties Company Compositions adhesives dispersees dans l'eau
CN102226069A (zh) * 2011-05-16 2011-10-26 江苏大中制漆有限公司 一种钢板植绒用水基胶黏剂及其制备方法
CN104031596A (zh) * 2014-06-27 2014-09-10 重庆中科力泰高分子材料股份有限公司 一种低成型温度水性聚氨酯胶粘剂及其制备方法
WO2020069132A2 (fr) * 2018-09-26 2020-04-02 Henkel IP & Holding GmbH Composition adhésive de polyuréthane durcissable à l'humidité à un constituant pour des applications de toiture

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0798359A2 (fr) * 1996-03-19 1997-10-01 Basf Aktiengesellschaft Composition aqueuse d'adhésif de contact
JPH09302220A (ja) * 1996-05-15 1997-11-25 Dainippon Ink & Chem Inc 水性ポリウレタン樹脂組成物及び接着剤
WO2001077248A1 (fr) * 2000-04-05 2001-10-18 3M Innovative Properties Company Compositions adhesives dispersees dans l'eau
CN102226069A (zh) * 2011-05-16 2011-10-26 江苏大中制漆有限公司 一种钢板植绒用水基胶黏剂及其制备方法
CN104031596A (zh) * 2014-06-27 2014-09-10 重庆中科力泰高分子材料股份有限公司 一种低成型温度水性聚氨酯胶粘剂及其制备方法
WO2020069132A2 (fr) * 2018-09-26 2020-04-02 Henkel IP & Holding GmbH Composition adhésive de polyuréthane durcissable à l'humidité à un constituant pour des applications de toiture

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Periodic Table of Elements", 1990, CRC PRESS

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