WO2019038324A1 - Composition de revêtement d'amorce ou d'adhésif - Google Patents

Composition de revêtement d'amorce ou d'adhésif Download PDF

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Publication number
WO2019038324A1
WO2019038324A1 PCT/EP2018/072661 EP2018072661W WO2019038324A1 WO 2019038324 A1 WO2019038324 A1 WO 2019038324A1 EP 2018072661 W EP2018072661 W EP 2018072661W WO 2019038324 A1 WO2019038324 A1 WO 2019038324A1
Authority
WO
WIPO (PCT)
Prior art keywords
primer
adhesive coating
coating composition
heat
activated initiator
Prior art date
Application number
PCT/EP2018/072661
Other languages
English (en)
Inventor
Tommy HARALDSON
Henrik MIKAELSSON
Carl Fredrik Carlborg
Original Assignee
Mercene Labs Ab
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 Mercene Labs Ab filed Critical Mercene Labs Ab
Publication of WO2019038324A1 publication Critical patent/WO2019038324A1/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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate

Definitions

  • the present invention relates generally to an epoxy-thiol primer made with an initiator system comprising an inactive latent nucleophile as well as a quaternary ammonium salt. More in detail, it relates to a primer or adhesive coating composition for epoxy-thiol systems and comprises an
  • composition is intended to be used as a coating where further coating (s) are to be applied onto the coating, i.e. as a primer coating or alternatively it is intended to be used as an adhesive.
  • Primers are often used as an intermediate layer before another coating is applied on the primer coating.
  • Adhesives are used as a layer between the surfaces of separate items for binding them together. For sensitive substrates, it is a problem that heating to rather high temperature has to be used to initiate a polymerization reaction in a coating.
  • composition may be too short to be useful. In particular, it is difficult to combine gentle hardening conditions and a long pot life. It is also desired to improve the adhesion to various substrates.
  • Latent amine or amide curing agents are well known in the art for epoxy systems .
  • WO 2013/167576 discloses an object with a coating comprising: a) covalent bonds formed by reaction of a thiol group and a carbon-carbon double bond, b) covalent bonds formed by reaction of a thiol group and epoxide group, c) covalent bonds formed by a reaction of a carbon-carbon double bond and an epoxide group, said coating comprising a first primer coating and a second coating, said coating comprising
  • WO 2012/042059 discloses a method for the manufacture of articles of thiol-ene polymers comprises the steps: a) reacting a compound comprising at least two thiol groups and a compound comprising at least two carbon-carbon double bonds, in off stoichiometry ratios to obtain a first
  • said first intermediate article comprises at least one unreacted group selected from an unreacted thiol group and an unreacted carbon-carbon double bond
  • said first intermediate article comprises at least one unreacted group selected from an unreacted thiol group and an unreacted carbon-carbon double bond
  • US 4,173,476 discloses a photopolymerizable epoxy with a certain complex salt present. (A triarylsulfonium complex salt) A heat-induced polymerization is not disclosed.
  • US 6,166,101 discloses an initiator giving rise to a cation when irradiated with UV-light .
  • a heat-activated initiator is not mentioned.
  • US 7,572,506 discloses a polyamine curing agent for the epoxy. Such curing agents are known to be heat-activated also at low temperature. It is mentioned curing at room temperature within 10 to 20 hours. Also 20 to 60 minutes at, for example, 40 to 80 °C. There is also disclosed the use as a primer.
  • US 20100285309 discloses an epoxy which is cured with a heat- activated initiator. There is also disclosed use as a primer.
  • Various salts may be present as a corrosion inhibitor.
  • the initiator or curative may for instance be primary or
  • US 2010273005 discloses a heat curing epoxy composition with a hardener and an accelerant of a general Markush formula. Curing temperatures of 100-220 °C are mentioned.
  • WO 01/00698 discloses both two part and one part adhesive compositions. There are disclosed polyfunctional
  • the compounds include one or more aromatic rings, wherein at least one aromatic ring is substituted with at least one alkylthio group and at least one oxyalkylthio group.
  • the adhesive systems include an epoxy resin or other compounds such as terminal olefins which are known to react with thiols.
  • the compounds are used in combination with amine curatives as a two-component curing system for epoxy resins. Catalysts are also encompassed.
  • a one component formulation is provided where the compositions are pre-mixed and partially cured before freezing them to stop the curing process. The curing continues when the composition is thawed and applied.
  • the one-part adhesive has the drawback that it has to be frozen in order to halt the ongoing curing process until the curing is desired.
  • a primer or adhesive coating composition comprising a polymerizable compound comprising at least one epoxide group, a polymerizable compound comprising at least one thiol group, wherein the primer or adhesive coating composition comprises at least one quaternary ammonium salt and at least one heat-activated initiator which is a latent amine or amide, wherein the heat- activated initiator is inactive before heated to an
  • the adhesion is improved for known difficult substrates such as melamine.
  • a quaternary ammonium salt improves the adhesion especially for known difficult materials such as melamine, in particular when the curing temperature is not so high, i.e. well within the temperature limits mentioned in the application.
  • the primer is suitable for sensitive
  • the temperature can be kept as low as 85 °C during curing. Still the composition has a long pot life of about 24 hours in one embodiment, which allows for many industrial coating applications. The curing at low temperature still has an acceptable curing time in spite of the low temperature.
  • composition indicates the intended use for the composition. It is thus a composition that can be used to make a primer coating, or to make an adhesive coating. Thus, there is provided a coating composition that can be used both as a primer coating
  • composition and as an adhesive coating composition.
  • the word coating includes all forms of application and dispensing to a surface.
  • a primer or adhesive coating composition comprising a polymerizable compound comprising at least one epoxide group, a polymerizable compound comprising at least one thiol group, wherein the primer or adhesive coating composition comprises at least one quaternary ammonium salt and at least one heat-activated initiator which is a latent amine or amide, wherein the heat- activated initiator is inactive before heated to an
  • the heat-activated initiator should be inactive before heating to an activation temperature.
  • the temperature is the temperature to which the composition is heated when it is desired to initiate the curing.
  • the curing has been partially stopped by freezing the mixture.
  • the initiator should be completely inactive in the one-component composition so as not contribute to any slow curing. Particular measures are needed to prevent the initiator from contributing to the curing before heating.
  • the heat-activated initiator can be held inactive in several ways. In one embodiment, the heat- activated initiator is inactive before heated to an
  • activation temperature by being provided in the form of particles completely coated with a material adapted to melt at the activation temperature.
  • the initiator is provided as particles, which particles are coated with a material that melts at the activation temperature so that the initiator is exposed to the surroundings and is able to initiate the curing reaction.
  • the material adapted to melt at the activation temperature is wax.
  • waxes are lipophilic malleable solids around room temperature.
  • Waxes include higher alkanes and lipids. Waxes are insoluble in water but soluble in organic non-polar solvents. Thus, organic non- polar solvents should be avoided or at least not used to such an extent that they dissolve the coating of wax.
  • the heat-activated initiator is inactive before heated to an activation temperature by being provided in an inactive crystalline form adapted to melt to an active form at the activation temperature.
  • Some initiators are inactive or virtually inactive when in crystalline form, but when melted or in amorphous form, they are active. The crystals melt or change into amorphous structure when heated above the activation temperature.
  • the primer or adhesive coating composition comprises at least one compound increasing the pH .
  • the pH of an aqueous solution of the components is above 7. In one embodiment, the pH is above 8. In one embodiment the primer or adhesive coating composition
  • the primer or adhesive coating composition comprises at least one compound increasing the pH, said at least one compound increases the pH at least during heating.
  • the primer or adhesive coating composition comprises at least one compound increasing the pH at all temperatures at least to some extent. In an alternative embodiment the primer or adhesive coating composition
  • the temperature during such heating is the same as when the primer or adhesive coating composition is heated to initiate the polymerization reaction.
  • the heating to increase the pH is thus the same heating as when initiating the
  • the pH is important during the initiation of the polymerization reaction and thus it is sufficient that the pH is increased during the heating.
  • the primer or adhesive coating composition comprises at least one compound lowering the pH, said at least one compound being adapted to evaporate during heating so that the pH increases.
  • the pH is also increased during heating but with aid of a compound evaporating during heating.
  • acetic acid is utilized as the evaporating compound so that the pH increases when it evaporates. This alternative approach is particularly suitable for thin films where evaporation is easy due to the large surface to bulk ratio.
  • the at least one heat-activated initiator is a latent amine. In one embodiment the at least one heat- activated initiator is amide. In one embodiment the at least one heat-activated initiator comprises both an amine and an amide. In one embodiment the at least one heat-activated initiator is a latent cycloaliphatic amine. In one embodiment the at least one heat-activated initiator is an imidazole.
  • the at least one quaternary ammonium salt is tetrabutylammonium acetate. In one embodiment the amount of the at least one quaternary ammonium salt is in the range 0.1 to 10 % of the weight of the total composition. In one embodiment the amount of the at least one quaternary ammonium salt is in the range 0.3 to 2 % of the weight of the total composition. In one embodiment the amount of the at least one heat- activated initiator is in the range 0.1 to 15 % of the weight of the total composition. Regarding calculation of the amount of the at least one heat-activated initiator, any coating adapted to melt at the activation temperature is included in the weight of the initiator.
  • the coating material (such as wax) is included in the weight of the initiator. This facilitates the measuring of the initiator since the initiator is often provided from an external manufacturer in the form of coated particles. If the initiator for instance is provided as uncoated crystals or other inactive particles without coating, the initiator particles are weighed to determine the amount of initiator.
  • the relation between the amount of the polymerizable compound comprising at least one epoxide group, and the polymerizable compound comprising at least one thiol group is so that the total number of epoxide groups and the total number of thiol groups is about equal, i.e. a
  • the number of epoxy groups is the same as the number of thiol groups or at least within ⁇ 10% of the number of thiol groups. In one embodiment, the number of epoxy groups is within ⁇ 5% of the number of thiol. In another embodiment the number of epoxy groups is within ⁇ 1% of the number of thiol groups .
  • polymerizable compounds in the composition is non- stoichiometric, i.e. total number of epoxide groups and the total number of thiol groups in the composition is not equal.
  • the number of epoxy groups is at least 10% higher than the number of thiol groups. In one embodiment the number of epoxy groups is from 10% to 50% higher than the number of thiol groups.
  • a polymerizable compound may comprise more than one epoxide group, or more than one thiol group respectively. The number of epoxide or thiol groups in the composition is used to calculated the ratio between the amount of polymerizable compound comprising epoxide groups and, the amount of
  • the composition comprises a polymerizable compound comprising at least one carbon-carbon double bond. Additional monomer compounds are optional and can be added as needed to obtain the desired final polymerized product.
  • a method of coating a substrate comprising the steps of
  • a primer or adhesive coating composition comprising a polymerizable compound comprising at least one epoxide group, a polymerizable compound comprising at least one thiol group, wherein the primer or adhesive coating composition comprises at least one quaternary ammonium salt and at least one heat-activated initiator which is a latent amine or amide, wherein the heat-activated initiator is inactive before heated to an activation temperature,
  • the polymerization reaction is complete and in an alternative embodiment the polymerization reaction is partial. In one embodiment the polymerization reaction is first partial and then the polymerization reaction is allowed to proceed to completion after a period of time.
  • the initiating is performed by heating to a temperature in the interval 75-120 °C. In one embodiment the initiating is performed by heating to a temperature in the interval 75-100 °C. In one embodiment the initiating is performed by heating to a temperature in the interval 80-95 °C. In one embodiment the initiating is performed by heating to a temperature in the interval 82-90 °C. In one embodiment the initiating is performed by heating to a temperature in the interval 83-89 °C. It is an advantage that the
  • the method comprises a further step d) applying at least one further coating on at least parts of the substrate. Since the primer is intended to be used with another coating on top, it is a natural step to apply a further coating, either directly after heating and curing of the primer or after an extended period of time.
  • the method comprises a further step of bringing another object in contact with at least a part of the applied primer or adhesive coating composition.
  • the other object is brought into contact with the coating composition either before initiating a polymerization reaction or when the polymerization reaction has completed only partially so that the polymerization reaction can complete to achieve good adhesion between the substrate and the other object.
  • When used as an adhesive one or both of the objects to be joined together are coated with the coating.
  • the substrate to be coated is a polymeric substrate .
  • a coated object wherein the coated object is made according to the description above.
  • an initiator comprising at least one quaternary ammonium salt and at least one heat-activated initiator which is a latent amine or amide, wherein the heat-activated initiator is inactive before heated to an activation temperature
  • kit of parts further comprises an instruction to heat a mixture of the components.
  • the tape thickness is approximately 30 microns. Apply a small amount of coating at one end of the glass slide. Spread the coating between the tape strips using a stainless steel doctor blade.
  • a hotplate set at 85 °C for 45 seconds. After the heating procedure, remove the sample and let it rest at ambient temperature. Use a spatula to determine when the coating has solidified.
  • the development of a tack free surface can be felt by a fingertip preferably wearing a thin nitrile rubber glove. The result is measured as the time from the start of the test to the point where the coating is tack free.
  • the Hamberger testing procedure is designed to evaluate the scratch resistance of coatings on wood or wood-based surfaces by using the Hamberger plane (behavior under scratching load from a curved, moderately sharp edge) .
  • the determined values are given in Newtons [N] as "scratch resistance according to the Hamberger test.
  • the method determines the resistance of a coated surface against abrasion by a narrow edge by
  • the Hamberger plane instrument consists of the following components: 1) Test blade made of carbide with a diameter of 12.75 mm at the cutting edge and a subsequently rounded edge, 2) Test edge, the segment of the cutting edge that is in contact with the test sample's surface during the test, 3) Rocker, a metal block for holding and fastening the test blade. It is
  • the samples to be tested were fixated horizontally, the Hamberger plane was placed on the sample, the test edge was lowered onto the surface and the loading device was set to the minimal test force to be expected, e.g. 10 N.
  • the Hamberger plane was then pushed horizontally over the sample surface for a distance of about 200 mm (test path) .
  • the path was then immediately inspected for damage.
  • damage includes visible or noticeable deviations in color, as well as a partial or complete abrasion of the coating in the area of the test path over a continuous length of at least 2 mm and/or clusters. Indentation traces or shiny traces that do not deviate in color are not rated as damage.
  • the test force was then increased and another test path is added and
  • Optional remainder up to 100wt% is solvents.
  • Ancamine 2441 is a modified polyamine designed for use as a latent curing agent for one-component adhesive formulations from Evonik®. It has a melting point about 124-135 °C and is provided as a powder with a particle size less than 10 pm. It is inactive in the provided form and becomes active upon heating. It is inactive in the provided form due to its crystalline structure . When heated it changes into an active structure .
  • LC-80 an encapsulated modified imidazole (amine) for one- component epoxy formulations from A&C Catalysts Inc®.
  • the average particle size is 10 pm. It is encapsulated with wax and melts in the range of about 90-110 °C, thereby activating the initiator.
  • TBAAc tetrabutylammonium acetate from Sachem.
  • the heat latent amine or amide curing agents gives a
  • coatings and adhesive applications for example roller coating .
  • HPL substrate formulation 10 (as described above) was applied using a 6 micron rod applicator and cured in a conveyor belt IR system. 2 minutes after exiting the conveyor belt system an acrylate base coat, UL1117 from Sherwin
  • Williams was applied using a 24 micron rod and cured with 500 mJ/cm 2 using a medium pressure Hg lamp.
  • a high gloss white HPL foil glued on chip board was coated with a mixture comprising 100 weight-parts of component A, 45 weight-parts of component B, 5.91 weight-parts of Ancamine 2441 and 1.48 weight-parts of TBAAc .
  • Another comparative mixture containing the same components except TBAAC was also prepared and coated similarly. All coatings were performed using a 6-micron rod-applicator.
  • the room temperature HPL substrate was fed into an IR equipped with a conveyor belt reaching 97-99 °C in 20 s time.
  • a few hundredths of one gram of the substrate formulation 10 (as described above) was placed centred on a glass slide. Another glass slide was placed on the applied substrate formulation in 90° angle compared to the first glass slide. The slide was placed on a hot plate heated to the desired temperature. The applied liquid product was carefully
  • the curing reaction is maintained until solidification.
  • the curing initiation works at 70 °C but becomes better at 85 °C.
  • the pot life for the composition is sufficient. After 22 hours the viscosity has not changed according to the

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne un système initiateur pour une amorce époxy ou un revêtement adhésif, la composition de revêtement d'amorce ou d'adhésif comprenant un composé polymérisable comprenant au moins un groupe époxyde, un composé polymérisable comprenant au moins un groupe thiol, et au moins un sel d'ammonium quaternaire et au moins un initiateur activé par voie thermique qui est une amine latente ou un amide latent, l'initiateur activé par voie thermique étant inactif avant d'être chauffé jusqu'à une température d'activation. Les avantages comprennent le fait que la température de durcissement est faible tout en ayant encore un temps de durcissement acceptable et que le délai d'utilisation est suffisamment long pour que le revêtement d'amorce ou d'adhésif convienne bien aux applications industrielles.
PCT/EP2018/072661 2017-08-23 2018-08-22 Composition de revêtement d'amorce ou d'adhésif WO2019038324A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE1751011-6 2017-08-23
SE1751011 2017-08-23

Publications (1)

Publication Number Publication Date
WO2019038324A1 true WO2019038324A1 (fr) 2019-02-28

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4173476A (en) 1978-02-08 1979-11-06 Minnesota Mining And Manufacturing Company Complex salt photoinitiator
US6166101A (en) 1997-11-21 2000-12-26 Kansai Paint Co., Ltd. Ultraviolet-curing coating composition for cans
WO2001000698A2 (fr) 1999-03-23 2001-01-04 Lord Corporation Agents de durcissement poly(mercaptopropylaryl)
US7572506B2 (en) 2004-06-30 2009-08-11 E. I. Du Pont De Nemours And Company Aqueous primer surfacer compositions
US20100273005A1 (en) 2007-11-14 2010-10-28 Sika Technology Ag Heat-curing epoxy resin composition containing non-aromatic ureas as accelerator
US20100285309A1 (en) 2007-09-21 2010-11-11 Henkel Ag & Co. Kgaa Primer compositions for adhesive bonding systems and coatings
WO2012042059A1 (fr) 2010-10-01 2012-04-05 Carl Fredrik Carlborg Procédé de fabrication d'articles à base de polymères de thiol-ène
US20130157058A1 (en) * 2011-12-16 2013-06-20 E. I. Du Pont De Nemours And Company Coated article comprising curable epoxy composition with quaternary ammonium bicarbonate curing catalyst, and method for preparing
WO2013167576A2 (fr) 2012-05-07 2013-11-14 Mercene Labs Ab Procédé et formulations pour la fabrication d'articles revêtus et composites

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4173476A (en) 1978-02-08 1979-11-06 Minnesota Mining And Manufacturing Company Complex salt photoinitiator
US6166101A (en) 1997-11-21 2000-12-26 Kansai Paint Co., Ltd. Ultraviolet-curing coating composition for cans
WO2001000698A2 (fr) 1999-03-23 2001-01-04 Lord Corporation Agents de durcissement poly(mercaptopropylaryl)
US6313257B1 (en) * 1999-03-23 2001-11-06 Lord Corporation Poly (mercaptopropylaryl) curatives
US7572506B2 (en) 2004-06-30 2009-08-11 E. I. Du Pont De Nemours And Company Aqueous primer surfacer compositions
US20100285309A1 (en) 2007-09-21 2010-11-11 Henkel Ag & Co. Kgaa Primer compositions for adhesive bonding systems and coatings
US20100273005A1 (en) 2007-11-14 2010-10-28 Sika Technology Ag Heat-curing epoxy resin composition containing non-aromatic ureas as accelerator
WO2012042059A1 (fr) 2010-10-01 2012-04-05 Carl Fredrik Carlborg Procédé de fabrication d'articles à base de polymères de thiol-ène
US20130157058A1 (en) * 2011-12-16 2013-06-20 E. I. Du Pont De Nemours And Company Coated article comprising curable epoxy composition with quaternary ammonium bicarbonate curing catalyst, and method for preparing
WO2013167576A2 (fr) 2012-05-07 2013-11-14 Mercene Labs Ab Procédé et formulations pour la fabrication d'articles revêtus et composites

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