WO2019028153A1 - Esters de phosphate d'épichlorhydrine utilisés en tant que promoteurs d'adhérence - Google Patents

Esters de phosphate d'épichlorhydrine utilisés en tant que promoteurs d'adhérence Download PDF

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Publication number
WO2019028153A1
WO2019028153A1 PCT/US2018/044832 US2018044832W WO2019028153A1 WO 2019028153 A1 WO2019028153 A1 WO 2019028153A1 US 2018044832 W US2018044832 W US 2018044832W WO 2019028153 A1 WO2019028153 A1 WO 2019028153A1
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WO
WIPO (PCT)
Prior art keywords
promoting agent
film
adhesion promoting
composition
substrate
Prior art date
Application number
PCT/US2018/044832
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English (en)
Inventor
Scott Yin
Andrew Guo
Michael Edward O'brien
Original Assignee
Stepan Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Stepan Company filed Critical Stepan Company
Publication of WO2019028153A1 publication Critical patent/WO2019028153A1/fr

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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
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • 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
    • C09J2475/00—Presence of polyurethane
    • C09J2475/003—Presence of polyurethane in the primer coating
    • 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
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined

Definitions

  • the present technology relates to a phosphate-ester adhesion promoter that can improve the adhesion of film-forming compositions to a substrate.
  • the present technology also relates to the film-forming compositions that comprise the adhesion promoter.
  • the film-forming compositions may be polyurethane, epoxy, thermosetting acrylic, or silicone compositions.
  • Film-forming compositions such as polyurethane compositions
  • Adhesives can be used for bonding a variety of materials, including metals and plastics.
  • Coatings can be applied to various substrates and allowed to dry or cure to form a protective or decorative film on the surface of the substrates.
  • Suitable substrates include metals, plastics, composites, wood, and concrete.
  • Sealants are applied to a variety of surfaces and allowed to dry or cure to form a watertight or airtight coating. In all of these applications, an important property of the film-forming composition is the ability to adhere to the substrate or surface to which it has been applied.
  • Adhesion promoters have been developed to improve bond strength between coating, adhesive, and sealant compositions and different substrates.
  • Known adhesion promoters include epoxy-functional silanes, amine-functional metal organic complexes, and amine-functional zircoaluminates.
  • these adhesion promoters may not give satisfactory results on some substrates, such as untreated steel, untreated aluminum, composite materials, and plastics.
  • the disclosure provides an adhesion promoting agent for enhancing the adhesion of a film-forming composition to a substrate, wherein the adhesion promoting agent comprises a mixture of epichlorohydnn phosphate esters that is the reaction product of epichlorohydnn reacted with phosphoric acid in a molar ratio of greater than 1 :1 but less than 3:1 , such as about 2:1 or 2:1 .
  • this disclosure provides a method for enhancing adhesion of a film-forming composition to a substrate comprising: (a) adding an adhesion promoting agent to at least one of the film-forming composition or the substrate, wherein the adhesion promoting agent comprises a mixture of epichlorohydrin phosphate esters that is the reaction product of epichlorohydrin reacted with phosphoric acid in a molar ratio of greater than 1 :1 but less than 3:1 , such as about 2:1 or 2:1 ;
  • the disclosure provides a system comprising:
  • an adhesion promoting agent comprising a mixture of epichlorohydrin phosphate esters that is the reaction product of epichlorohydrin reacted with phosphoric acid in a molar ratio of greater than 1 :1 but less than 3:1 , such as about 2:1 or 2:1 ;
  • adhesion promoting agent is present in the system in an amount effective to provide an increased bond strength between the film-forming composition and the substrate compared to a similar system that does not contain the adhesion promoting agent.
  • the disclosure provides a polyurethane composition that comprises a polyester polyol; an activator for reacting with the polyester polyol to form a polyurethane film; and an adhesion promoting agent comprising a mixture of epichlorohydrin phosphate esters that is the reaction product of epichlorohydrin reacted with phosphoric acid in a molar ratio of greater than 1 :1 but less than 3:1 , such as about 2:1 or 2:1 .
  • Figure 1 is a graph comparing adhesion test results of an untreated aluminum substrate treated with a polyurethane coating having no adhesion promoting agent, and polyurethane coatings having different concentrations of the adhesion promoting agent of the present technology;
  • Figure 2 is a graph comparing adhesion test results of a steel substrate treated with a polyurethane coating having no adhesion promoting agent, and polyurethane coatings having different concentrations of the adhesion promoting agent of the present technology;
  • Figure 3 is a graph comparing adhesion test results of an untreated aluminum substrate treated with a polyurethane coating having no adhesion promoting agent, polyurethane coatings containing known adhesion-promoting agents, and a polyurethane coating containing the adhesion promoting agent of the present technology;
  • Figure 4 is a graph comparing adhesion test results of a steel substrate treated with a polyurethane coating having no adhesion promoting agent, polyurethane coatings containing known adhesion-promoting agents, and a polyurethane coating containing the adhesion promoting agent of the present technology.
  • the present technology encompasses an adhesion promoting agent that can enhance the adhesion of film-forming compositions, such as polyurethane, epoxy, thermosetting acrylic, or silicone compositions, to various substrates.
  • film-forming compositions may be in the form of coatings, adhesives, and sealants.
  • the adhesion promoting agent is particularly useful for enhancing the adhesion of polyurethane compositions to untreated surfaces, such as untreated aluminum, untreated steel, composite materials, wood, and plastics that normally require primer layers to achieve adequate adhesion.
  • the adhesion promoting agent comprises a mixture of epichlorohydrin phosphate esters that can be prepared by reacting epichlorohydrin (EPI) with phosphoric acid in a molar ratio that is greater than 1 :1 but less than 3:1 .
  • the molar ratio of epichlorohydrin to phosphoric acid is preferably about 2:1 , such as 2:1 .
  • the molar ratio of epichlorohydrin to phosphoric acid may range from 1 .1 :1 to 2.9:1 , alternatively 1 .2:1 to 2.8:1 , alternatively 1 .4:1 to 2.6:1 ; alternatively 1 .5:1 to 2.5:1 , alternatively 1 .8:1 to 2.2:1 .
  • the molar ratio of epichlorohydrin to phosphoric acid may be 1 .2:1 , 1 .3:1 , 1 .4:1 , 1 .5:1 , 1 .6:1 , 1 .7:1 , 1 .8:1 , 1 .9:1 , 2.1 :1 , 2.2:1 , 2.3:1 , 2.4:1 , 2.5:1 , 2.6:1 , 2.7:1 , 2.8:1 , or 2.9:1 .
  • the reaction can be via a single-step procedure, in which the desired amounts of epichlorohydrin and phosphoric acid are introduced into a reactor.
  • the reaction temperature can range from room temperature (for example, 25°C) up to 80°C. Preferred temperatures range from about 40°C to about 60°C. Since the reaction is exothermic, it is desirable to use a water bath or other cooling method to control the reaction temperature. It is also desirable to incrementally add the epichlorohydrin to the phosphoric acid in the reactor. The reaction proceeds for a time sufficient for all of the epichlorohydrin to react with the phosphoric acid.
  • the reaction can be performed neat, or in a suitable solvent.
  • Suitable solvents include acetates, such as n-butyl acetate, carbonates, such as propylene carbonate, hydrocarbon solvents, such as hexane, toluene, xylene, and terpenes, and certain oxygenated solvents, such as ketones, glycol ethers, glycol esters, and nitroparaffin.
  • the resulting reaction product is a mixture comprised of phosphoric acid monoesters and diesters along with residual phosphoric acid. Minor amounts of other compounds resulting from the reaction may also be present in the reaction product mixture. It should be appreciated by one skilled in the art that the amount of each component in the reaction product need not be exact, and that some variation in the particular amounts of the components in the reaction product will occur from batch to batch.
  • the epichlorohydrin and phosphoric acid reaction product can be used as the adhesion promoting agent without further purification, and has an acid value ranging from about 200 to about 400 mg KOH/g.
  • the adhesion promoting agent can be used as a 100% solids material. However, it may be desirable to dilute the adhesion promoting agent in a solvent to reduce its viscosity and improve its handling properties.
  • Suitable solvents include acetates, such as n-butyl acetate, carbonates, such as propylene carbonate, hydrocarbon solvents, such as hexane, toluene, xylene, and terpenes, and certain oxygenated solvents, such as ketones, glycol ethers, glycol esters, and nitroparaffin. Mixtures of solvents may also be used.
  • the solvent or mixture of solvents may comprise from about 5% to about 95% by weight based on the combined weight of the solvent and the adhesion promoter.
  • the adhesion promoting agent can be used as an additive in the film forming compositions for coatings, adhesives, and sealants.
  • the adhesion promoting agent can be applied as is (either alone or in a solvent) directly to a substrate as a pretreatment to enhance the adhesion of the composition being applied to the substrate.
  • the adhesion promoting agent can be added and blended into solvent borne or high solids type curable film-forming formulations to improve adhesion of the composition to different substrates.
  • film-forming compositions include polyurethane compositions, epoxy compositions, thermosetting acrylic compositions, and silicone compositions.
  • Polyurethane formulations typically comprise one or more active hydrogen containing compounds, such as polyols, and at least one activator, such as isocyanates.
  • the polyols can be aromatic, aliphatic, or a combination thereof, and include without limitation, polyester polyols, polyether polyols, polyether ester polyols, and/or polycaprolactones.
  • Epoxy compositions typically comprise one or more resins having an epoxy functionality and at least one curing agent, such as amines.
  • the one or more epoxy resins may be aromatic, aliphatic, cycloaliphatic, or mixtures thereof.
  • Thermosetting acrylic compositions include hydroxyl functional (meth)acrylic resins that can be cross-linked with active nitrogen-containing resins, or carboxyl functional (meth)acrylic resins that can be cross-linked with epoxy resins.
  • Silicone compositions can comprise moisture curing and/or thermal curing silicone resins.
  • the amount of adhesion promoting agent added will depend on the particular film-forming composition used and the particular substrate involved.
  • An effective amount of adhesion promoting agent is about 10% by weight or less, based on the total weight of the film-forming composition.
  • the amount of the adhesion promoting agent is about 0.01 % to about 8% by weight, alternatively about 0.01 % to about 7% by weight, alternatively about 0.02% to about 5% by weight, alternatively about 0.03% to about 3% by weight, alternatively about 0.01 % to about 1 .5%, alternatively about 0.05% to about 1 .0%, alternatively about 0.05% to about 0.5%, alternatively about 0.06% to about 0.25%, based on the total weight of the film- forming composition.
  • the adhesion promoting agent When used as a pretreatment agent, the adhesion promoting agent can be applied directly to the substrate surface, and then the film-forming coating, adhesive, or sealant composition is applied over the pretreatment agent and substrate surface.
  • the adhesion promoting agent can be applied as is (100% solids), or dissolved or dispersed in a solvent. Suitable solvents are described above. The amount of solvent can be from about 5% to about 95% by weight.
  • the epichlorohydrin phosphate ester adhesion promoting agent described herein surprisingly provides enhanced adhesion of film-forming coatings, adhesives, and sealants to a variety of substrates, such as metal, wood, composite materials, glass, concrete, and plastic substrates. Even more surprising, dramatically improved adhesion is achieved with untreated or poorly treated surfaces, such as cold roll steel or untreated aluminum, even with small amounts (less than 0.2 wt. %) of the adhesion promoting agent. Typically, bonding to untreated metal such as cold roll steel and aluminum is difficult without some type of pretreatment in order to achieve proper bonding strength.
  • adhesion promoting agent of the present technology provides adequate bond strengths to untreated metals, without the need for a pretreatment step.
  • the enhanced adhesion properties may be due to the mixture of the monoesters, diesters, and phosphoric acid resulting from the reaction of epichlorohydrin with phosphoric acid.
  • the adhesion promoting agent may reduce metal corrosion due to the phosphate ester structure.
  • the adhesion promoting agent may also provide enhanced adhesion to concrete materials.
  • the polyurethane, epoxy, or other compositions comprising the epichlorohydrin phosphate ester adhesion promoting agent can be applied to the desired substrate by any standard method known in the art, such as rolling, brushing, spraying, or dipping. After application, the polyurethane composition is allowed to dry or cure for an appropriate length of time and curing conditions to form the coating, adhesive, or sealant on the substrate. Drying or curing can be at room temperature and/or at elevated temperatures, such as up to about 150°C depending on the formulation and/or the prescribed curing conditions.
  • Adhesion of the coatings is measured by the cross-hatch tape test according to ADTM D 3359-95. Briefly, a lattice pattern with cuts in each direction is made in the film to the substrate. Pressure-sensitive tape is applied over the lattice and then removed. Test Method B is used to evaluate adhesion, wherein a rating of 5 indicates 0% of the coating is removed, and a rating of 0 indicates greater than 65% of the coating is removed.
  • the epichlorohydrin phosphate ester adhesion promoter made according to Example 1 was blended into a commercial, two component polyurethane system (Rust- Oleum ® 9400) at two different amount levels, and compared to the system without the addition of the adhesion promoter.
  • the amount of epichlorohydrin phosphate ester used in the two formulations was 0.07% by weight and 0.12% by weight, based on the total weight of the formulation.
  • the formulations prepared and tested are shown in Table 1 .
  • Coated metal panels for testing were prepared by first cleaning the metal panels with acetone before the coating formulation was applied.
  • Rust-Oleum ® 9400 polyol was mixed with Rust-Oleum ® 9401 activator in the desired ratio for about 30 seconds and applied to the metal panels using a 150 mil drawn down rod.
  • the coatings were allowed to cure at room temperature for seven days before cross hatch adhesion testing was done.
  • Figure 1 graphically illustrates the results of cross-hatch adhesion testing for the test formulations (Formulations B and C), and the control formulation (Formulation A) on an untreated aluminum panel. From Figure 1 it can be seen that the test formulations containing the epichlorohydrin phosphate ester adhesion promoting agent had ratings of 4 or 5, whereas the control had a rating of 2 (15-35% coating removed) for the untreated aluminum substrate. The results show a significant improvement in adhesion of the coating on untreated aluminum when the epichlorohydnn phosphate ester adhesion promoting agent is added to the formulation.
  • the test formulation containing epichlorohydnn phosphate ester in an amount of 0.07% by weight achieved a rating of 5 at both the 1 week and 2 week evaluations, showing that enhanced adhesion is obtained at very low levels of additive.
  • Figure 2 graphically illustrates the results of cross-hatch adhesion testing for the test formulations and the control formulation on an untreated steel panel. All the formulations had a rating of 5 for the untreated steel substrate.
  • Test formulations were prepared by adding an adhesion promoter to the polyester urethane component of a commercial polyurethane system (Rustoleum ® 9400) according to the following Table 2.
  • the commercial polyurethane system without an added adhesion promoter served as a control (Formulation A).
  • the adhesion promoters added to the respective formulations were (1 ) the epichlorohydrin phosphate ester (EMPA) adhesion promoting agent of the present technology; (2) a silane-based adhesion promoter; (3) an amino functional metal complex; and (4) an amino functional zircoaluminate.
  • EMPA epichlorohydrin phosphate ester
  • Coated metal panels for testing were prepared as described in Example 2, and the coatings were allowed to cure at room temperature for 7 days before cross- hatch adhesion testing was done.
  • Figure 3 graphically illustrates the results of cross-hatch adhesion testing for each of the test formulations and the control formulation on an untreated aluminum panel. From Figure 3 it can be seen that the test formulation containing the epichlorohydrin phosphate ester (EMPA) adhesion promoting agent had a rating of 5 (0% coating removed), whereas the other three test formulations each had a rating of 0 (greater than 65% coating removed). The control had a rating of 1 (35-65% coating removed).
  • EMPA epichlorohydrin phosphate ester
  • Figure 4 graphically illustrates the results of cross-hatch adhesion testing for each of the test formulations and the control formulation on an untreated steel panel. From Figure 4 it can be seen that each of the test formulations had a rating of 5.
  • the Figure 3 and Figure 4 test results show that, although the test formulations containing the commercial adhesion promoters provided good adhesion of the polyurethane coating to untreated steel, they were not effective (and indeed were detrimental) for an untreated aluminum substrate.
  • the epichlorohydrin phosphate ester adhesion promoting agent of the present technology provided good adhesion of the polyurethane coating to both metal substrates.
  • the epichlorohydrin phosphate ester adhesion promoter of the present technology was added to different commercially available adhesives, and the adhesives with the adhesion promoter were compared to the same adhesives without the adhesion promoter for adhesive properties on different substrates.
  • Test formulations were prepared by adding to the following commercial products an amount of 0.7% by weight based on the weight of the test formulation of a solution comprising 10% by weight of the epichlorohydrin phosphate ester adhesion promoter in n-butyl acetate solvent (0.07% epichlorohydrin phosphate ester active):
  • Gorilla Glue - a one component moisture cure liquid polyurethane adhesive from Gorilla Glue Company
  • Liquid Nails (NL-150) general purpose household adhesive from PPG Industries
  • Wood-to-substrate lap sheer assemblies were made in sets of five by first making marks across the bonding faces of wood samples (0.125 inches thick, trimmed to 1 " x 4") to allow separate inch square overlaps between the wood and the test substrate materials.
  • the test substrate materials were acrylonitrile-butadiene-styrene (ABS) (0.125 inches thick), polycarbonate (PC) (0.1 18 inches thick), aluminum (Al) (0.063 inches thick), thermoplastic olefin (TPO) (0.125 inches thick), and cold rolled steel (CRS) (0.0163 inches thick), each material trimmed to 1 " x 4" samples.
  • Wood bonding surfaces were pretreated by first rubbing briefly with a moist paper towel prior to applying the adhesive or sealant to the wood surface. Goop applied to the wood surface was allowed to free-air dwell for about one minute before proceeding to bond to a test substrate. After application of the adhesive to the wood surface, 10 mil glass beads were deposited onto the adhesive surface to maintain a constant 10 mil gap between bonded materials. The test substrate material was placed on the treated wood sample to make a 1 -inch square bond between the two substrates and the substrates were clamped together to maintain pressure throughout the curing process.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne un promoteur d'adhérence visant à favoriser l'adhérence d'une composition filmogène, telle qu'un polyuréthane, à un substrat. Le promoteur d'adhérence comprend des esters d'acide phosphorique qui sont les produits réactionnels de l'épichlorhydrine ayant réagi avec de l'acide phosphorique selon un rapport molaire supérieur à 1 : 1, mais inférieur à 3 : 1 et, de préférence, égal à environ 2 : 1. L'invention concerne également des compositions de polyuréthane comprenant le promoteur d'adhérence en tant qu'additif, et des systèmes dans lesquels le promoteur d'adhérence assure une adhérence améliorée de la composition de polyuréthane à un substrat.
PCT/US2018/044832 2017-08-02 2018-08-01 Esters de phosphate d'épichlorhydrine utilisés en tant que promoteurs d'adhérence WO2019028153A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201762540368P 2017-08-02 2017-08-02
US62/540,368 2017-08-02

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Publication Number Publication Date
WO2019028153A1 true WO2019028153A1 (fr) 2019-02-07

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3281502A (en) * 1959-05-22 1966-10-25 Wyandotte Chemicals Corp Phosphorus acid-halohydrin compounds
WO2016067605A1 (fr) * 2014-10-28 2016-05-06 ナガセケムテックス株式会社 Composition de revêtement

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3281502A (en) * 1959-05-22 1966-10-25 Wyandotte Chemicals Corp Phosphorus acid-halohydrin compounds
WO2016067605A1 (fr) * 2014-10-28 2016-05-06 ナガセケムテックス株式会社 Composition de revêtement

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