WO2020130285A1 - Composition adhésive sensible à la pression d'émulsion acrylique - Google Patents

Composition adhésive sensible à la pression d'émulsion acrylique Download PDF

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Publication number
WO2020130285A1
WO2020130285A1 PCT/KR2019/011396 KR2019011396W WO2020130285A1 WO 2020130285 A1 WO2020130285 A1 WO 2020130285A1 KR 2019011396 W KR2019011396 W KR 2019011396W WO 2020130285 A1 WO2020130285 A1 WO 2020130285A1
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Prior art keywords
meth
acrylate
monomer
sensitive adhesive
adhesive composition
Prior art date
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Ceased
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PCT/KR2019/011396
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English (en)
Korean (ko)
Inventor
이승모
양승훈
박용수
황윤태
김효민
서성종
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LG Chem Ltd
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LG Chem Ltd
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Publication date
Priority claimed from KR1020190109115A external-priority patent/KR102332742B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN201980009181.5A priority Critical patent/CN111684035B/zh
Priority to US16/963,712 priority patent/US20210079271A1/en
Priority to EP19899654.8A priority patent/EP3722387B1/fr
Publication of WO2020130285A1 publication Critical patent/WO2020130285A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
    • C08F2/30—Emulsion polymerisation with the aid of emulsifying agents non-ionic
    • C—CHEMISTRY; METALLURGY
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    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • C—CHEMISTRY; METALLURGY
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08F212/00—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 an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/06—Hydrocarbons
    • C08F212/08—Styrene
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    • C08F218/00—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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
    • C08F218/02—Esters of monocarboxylic acids
    • C08F218/04—Vinyl esters
    • C08F218/06—Vinyl formate
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    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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    • 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
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    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1803—C3-(meth)acrylate, e.g. (iso)propyl (meth)acrylate
    • 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
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    • C08F220/12—Esters of monohydric alcohols or phenols
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    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • 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
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    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1805—C5-(meth)acrylate, e.g. pentyl (meth)acrylate
    • 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
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    • 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
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    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
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    • C08F220/1809—C9-(meth)acrylate
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    • 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
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    • C08F226/00—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
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    • C09J2433/00—Presence of (meth)acrylic polymer

Definitions

  • the present invention relates to an acrylic emulsion pressure-sensitive adhesive composition.
  • PSA Pressure-Sensitive Adhesive
  • PSA is a material that has the property of adhering to an adhesive under a small pressure. It is a viscoelastic material different from the adhesive, and has the basic properties of initial adhesion, adhesion, and cohesion, and is used in various industries such as printing, chemicals, pharmaceuticals, home appliances, automobiles, and stationery.
  • the pressure-sensitive adhesive can be classified into acrylic, rubber, silicone, EVA, and the like according to the monomer used during manufacture, and can be classified into a solvent type, an emulsion type, and a hot melt type depending on the type.
  • Solvent-free pressure-sensitive adhesives are typically produced by water-based emulsion polymerization, and in terms of improving economic efficiency and processability, there are few aggregates and characteristics capable of stably realizing excellent adhesive properties are required.
  • the aqueous pressure-sensitive adhesive prepared by water-based emulsion polymerization uses a hydrophilic emulsifier, and in general, a bipolar single molecule having both hydrophilicity and hydrophobicity is used as a hydrophilic emulsifier.
  • a bipolar single molecule containing a hydrophilic group having strong polarity, such as sulfonate is used for particle formation and retention stability in an aqueous system.
  • the present invention is to provide a pressure-sensitive adhesive composition that does not leave a residue on the adherend, while showing excellent adhesion to both hydrophilic and hydrophobic substrates and a method for manufacturing the same.
  • the monomer mixture containing the (meth)acrylic acid ester-based monomer, vinyl-based monomer, and unsaturated carboxylic acid-based monomer is represented by the following formula (1), and has a hydration degree of 75 to 99% represented by the following formula (1).
  • It provides an acrylic emulsion pressure-sensitive adhesive composition comprising a copolymer emulsion-polymerized in the presence of a polymer emulsifier having a number average molecular weight of 1,000 to 8,000 g/mol.
  • the (meth) acrylic acid ester monomers are methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth) )Acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, 2 -Ethylhexyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, dodecyl (meth)acrylate, isobornyl (meth)acrylate, and lauryl (meth)acrylate It may be one or more selected from the group.
  • the vinyl-based monomer includes an alkyl group having 1 to 5 carbon atoms, a vinyl ester-based monomer; And it may be one or more selected from the group consisting of an aromatic vinyl-based monomer.
  • the unsaturated carboxylic acid-based monomer may be at least one selected from the group consisting of maleic anhydride, fumaric acid, crotanic acid, itaconic acid, and (meth)acrylic acid.
  • the present invention (meth) acrylic acid ester-based monomer, vinyl-based monomer and a monomer mixture containing an unsaturated carboxylic acid-based monomer; Crosslinking agents; And preparing a pre-emulsion comprising a polymer emulsifier represented by Formula 1, wherein the hydration degree represented by Formula 1 is 75 to 99%, and the number average molecular weight is 1,000 to 8,000 g/mol.
  • It provides a method for producing an acrylic emulsion pressure-sensitive adhesive composition comprising the step of emulsion polymerization of the pre-emulsion in the presence of an initiator.
  • the polymer emulsifier may be included in an amount of 0.1 to 5.0 parts by weight based on 100 parts by weight of the monomer mixture.
  • the (meth) acrylic acid ester-based monomer may be included in 70 to 99 parts by weight based on 100 parts by weight of the monomer mixture.
  • the vinyl-based monomer may be included in 1 to 25 parts by weight based on 100 parts by weight of the (meth) acrylic acid ester-based monomer.
  • the unsaturated carboxylic acid-based monomer may be included in an amount of 0.1 to 5 parts by weight based on 100 parts by weight of the (meth)acrylic acid ester-based monomer.
  • first and second are used to describe various components, and the terms are used only for the purpose of distinguishing one component from other components.
  • a monomer mixture comprising a (meth)acrylic acid ester-based monomer, a vinyl-based monomer, and an unsaturated carboxylic acid-based monomer is represented by the following Chemical Formula 1, and the degree of hydration represented by the following Chemical Formula 1
  • an acrylic emulsion pressure sensitive adhesive composition comprising a copolymer that is 75 to 99% and emulsion polymerized in the presence of a polymer emulsifier having a number average molecular weight of 1,000 to 8,000 g/mol.
  • m and n are the number of moles of repeating units constituting the polymer.
  • a bipolar single molecule containing a hydrophilic group having a strong polarity, such as sulfonate and sulfate, is used as an emulsifier.
  • an acrylic emulsion pressure-sensitive adhesive composition containing an emulsion of a copolymer, that is, an emulsion of latex particles using such an emulsifier, there is a problem of leaving a residue due to too strong adhesion to a hydrophilic substrate, and conversely, hydrophobicity of polyethylene, polypropylene, etc. There is a problem that the adhesion to the substrate is poor.
  • the present inventors have repeatedly studied the pressure-sensitive adhesive composition that exhibits excellent adhesion to both hydrophobic and hydrophilic substrates, but does not leave a residue on the adherend, and as a result, when using a polymer emulsifier such as Chemical Formula 1, adhesion properties are obtained.
  • the present invention was completed by confirming that it can be improved.
  • the polymer emulsifier is a modified polyvinyl alcohol-based polymer in which vinyl alcohol and methyl vinyl ketone monomer are copolymerized, and can be any of alternating, random, and block copolymers.
  • the hydroxy group which is a hydrophilic group, plays a role in maintaining particle stability in the water phase, and the polymer chain portion may serve as a space where polymerization occurs during emulsion polymerization.
  • the polymer emulsifier has a hydration degree of 75 to 99%, or 78 to 95%, represented by Equation 1 below.
  • the hydration degree is a percentage of repeating units derived from vinyl alcohol in the polymer, and the higher the hydration degree, the higher the hydrophilicity of the polymer. If the degree of hydration is less than 75%, there may be a problem of generation of residues due to too many carboxylic acid functional groups, and if it exceeds 99%, it is substantially polyvinyl alcohol, which is rapidly lowered in solubility in water and is suitable as an emulsifier. Since it does not, it is preferable to satisfy the hydration range.
  • the number average molecular weight of the polymer emulsifier is preferably in the range of 1,000 to 8,000 g/mol. If the number average molecular weight of the polymer emulsifier is less than 1,000 g/mol, there is a problem that the length of the polymer chain is excessively short, so that it does not function as an emulsifier. There may be a problem. At this time, the number-average molecular weight of the polymer emulsifier can be measured using gel permeation chromatography (GPC), as specified in the examples below.
  • GPC gel permeation chromatography
  • the polymer emulsifier is used in an amount of 0.1 to 5 parts by weight, or 0.5 to 3 parts by weight based on 100 parts by weight of the monomer mixture.
  • the content of the polymer emulsifier is less than 0.1 part by weight based on 100 parts by weight of the monomer mixture, the emulsifier is insufficient, so it is difficult to emulsify and polymerize through micelle formation, and there may be a problem that agglomerates are largely generated, and when it exceeds 5 parts by weight There may be a problem that adhesive properties are reduced due to the use of excessive emulsifiers.
  • the acrylic emulsion pressure-sensitive adhesive composition of the present invention is used by mixing (meth)acrylic acid ester-based monomer, vinyl-based monomer, and unsaturated carboxylic acid monomer as a monomer.
  • the acrylic emulsion pressure-sensitive adhesive composition of the present invention can have an effect of improving the overall adhesion and retention.
  • monomer mixture refers to a mixture of all monomers used for polymerization, and based on the monomers, as long as it can be used in an emulsion polymerization reaction to make an acrylic emulsion resin, there is no particular limitation.
  • the monomers may be added to the polymerization reaction in a mixed state, and the monomers may be sequentially added to the polymerization reaction.
  • the (meth)acrylic acid ester-based monomer may include a chain alkyl group having 1 to 10 carbon atoms, specifically methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (Meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate , Octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, dodecyl (meth)acrylate, iso It may be one or more selected from the group consisting of carbonyl (meth) acrylate, and lauryl (
  • the (meth)acrylic acid ester-based monomer may be included in 70 to 99 parts by weight based on 100 parts by weight of the monomer mixture.
  • the vinyl-based monomer includes an alkyl group having 1 to 5 carbon atoms, a vinyl ester-based monomer; And it may be one or more selected from the group consisting of an aromatic vinyl-based monomer.
  • the vinyl ester-based monomer includes a vinyl group at one end of the molecule, and an ester-type monomer including an alkyl group having 1 to 5 carbon atoms at the other end.
  • an ester-type monomer including an alkyl group having 1 to 5 carbon atoms at the other end.
  • acetic acid And one or more types selected from the group consisting of vinyl, vinyl propanoate, vinyl butanoate, and vinyl pentacarbonate.
  • the aromatic vinyl monomer is selected from the group consisting of styrene, methylstyrene, methylstyrene, butylstyrene, chlorostyrene, vinylbenzoic acid, methyl vinylbenzoate, vinylnaphthalene, chloromethylstyrene, hydroxymethylstyrene and divinylbenzene. 1 or more types are mentioned.
  • the vinyl monomer is used in an amount of 1 to 25 parts by weight, or 5 to 20 parts by weight based on 100 parts by weight of the (meth)acrylic acid ester monomer, and accordingly, the repeating unit derived from the vinyl monomer in the emulsifying polymer is the ( Met) about 1 to 25 parts by weight, or 5 to 20 parts by weight based on 100 parts by weight of the acrylic ester monomer.
  • the unsaturated carboxylic acid monomer may be at least one selected from the group consisting of maleic anhydride, fumaric acid, crotanic acid, itaconic acid, and (meth)acrylic acid, but is not limited thereto.
  • the unsaturated carboxylic acid-based monomer is used in an amount of 0.1 to 5 parts by weight, or 0.5 to 2 parts by weight based on 100 parts by weight of the (meth)acrylic acid ester-based monomer.
  • the unit is contained in about 0.1 to 5 parts by weight, or 0.5 to 2 parts by weight based on 100 parts by weight of the (meth) acrylic acid ester monomer.
  • the unsaturated carboxylic acid-based monomer is used too much, a problem may arise in which the viscosity of the emulsion polymerized copolymer particles rapidly increases, and too many cross-links outside the particles are formed, which may cause gelation. If used too little, the stability of the resulting copolymer particles may be degraded.
  • the additive in addition to the monomer mixture and emulsifier during the emulsion polymerization, it may further include other additives within a range that does not inhibit the desired effect of the invention.
  • the additive may include at least one crosslinking agent, polymerization initiator, buffer, wetting agent, reducing agent, chain transfer agent, and the like.
  • the crosslinking agent is polyethylene glycol diacrylate, polypropylene glycol diacrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, ethoxylated trimethylpropane triacrylate, tripropylene glycol diacrylate, 1, 3-butanediol diacrylate, pentatritol triacrylate, 3-trimethoxysilyl propyl methacrylate, vinyltrimethoxysilane, divinylbenzene, methacrylamide, methacrylamidoethyl ethyleneurea, methacryl ester 1 selected from the group consisting of ethylene urea, allyl ether ethylene urea, or [N-(2-(2-oxoimidazolin-1-yl)ethyl)(4-allylether)(3-hydroxy)butylamine] It may be more than a species.
  • the crosslinking agent may be used in an amount of 0 to 1.5% by weight
  • water-soluble polymerization initiators such as ammonium or alkali metal persulfate (ex.APS, ammonium persulfate), hydrogen peroxide, peroxide, and hydroxyl oxide can be used, and in order to perform an emulsion polymerization reaction at low temperature It may be used with one or more reducing agents, but is not limited thereto.
  • the content of the polymerization initiator may be used in an amount of 0.1 to 2.0% by weight based on the monomer mixture.
  • the polymerization initiator may be divided into one or more times during the polymerization step of the monomer mixture and appropriately divided within the above-described range.
  • the buffer examples include sodium bicarbonate, sodium carbonate, sodium phosphate, sodium sulfate, sodium chloride, sodium hydroxide, and the like, but are not limited thereto. Further, these may be used alone or in combination of two or more.
  • the buffer may serve to adjust the pH in the polymerization reaction and impart polymerization stability.
  • the buffer may be used in an amount of 0.1 to 0.8% by weight based on 100% by weight of the monomer mixture.
  • the wetting agent serves as an emulsifier that lowers the surface tension for coating properties, and its content can be used within a range well known in the art.
  • the wetting agent may include a dioctyl sodium sulfosuccinate (DOSS)-based compound.
  • the wetting agent may be used in an amount of 0.1 to 2% by weight based on 100% by weight of the monomer mixture.
  • the chain transfer agent serves to introduce homopolymers, which are polymers composed of only one type of monomer, into micelles, and may include sodium carbonate, sodium methylallyl sulfonate, n-dodecyl mercaptan, and the like. It is not.
  • the chain transfer agent may be used in an amount of 0.01 to 0.50% by weight based on 100% by weight of the monomer mixture.
  • a method of preparing an acrylic emulsion pressure sensitive adhesive composition comprising the step of emulsion polymerization of the free emulsion in the presence of an initiator.
  • the acrylic emulsion pressure-sensitive adhesive composition of the present invention described above may be specifically prepared by the following method, but is not limited thereto.
  • a pre-emulsion is prepared by first mixing a monomer mixture and a polymer emulsifier represented by Chemical Formula 1 with water.
  • a polymer emulsifier represented by Chemical Formula 1 represented by Chemical Formula 1
  • the formation of agglomerates can be reduced by forming a free emulsion before the emulsion polymerization reaction.
  • the (meth) acrylic acid ester-based monomer, vinyl-based monomer, unsaturated carboxylic acid-based monomer, and polymer emulsifier represented by Chemical Formula 1 used in preparing the free emulsion are as described above.
  • one or more other additives described above, that is, a crosslinking agent, a buffering agent, a wetting agent, a reducing agent, and a chain transfer agent may be added.
  • the pre-emulsion and the polymerization initiator are continuously added for a predetermined period of time in an equal ratio, and the pre-emulsion is subjected to emulsion polymerization.
  • water-soluble polymerization initiators such as ammonium or alkali metal persulfate (ex.APS, ammonium persulfate), hydrogen peroxide, peroxide, and hydroxyl oxide can be used, and an emulsion polymerization reaction is performed at low temperature. In order to do so, it may be used together with one or more reducing agents, but is not limited thereto. At this time, the content of the polymerization initiator may be used in an amount of 0.1 to 2.0% by weight based on the monomer mixture. In addition, the polymerization initiator may be divided into one or more times during the polymerization step of the monomer mixture and appropriately divided within the above-described range.
  • ammonium or alkali metal persulfate ex.APS, ammonium persulfate
  • hydrogen peroxide peroxide
  • peroxide peroxide
  • hydroxyl oxide hydroxyl oxide
  • the content of the polymerization initiator may be used in an amount of 0.1 to 2.0% by weight based on the
  • the time to continuously input the pre-emulsion and the polymerization initiator may be 3 to 5 hours.
  • the emulsion polymerization may be carried out in the presence of a polymerization initiator, or by stirring at a temperature of 70 to 90 °C for 3 to 8 hours. Specifically, the emulsion polymerization may be performed at a temperature of about 75 to 90° C. for about 3 hours to about 6 hours. And, considering the physical properties of the pressure-sensitive adhesive may be a polymerization temperature of about 75 to about 85 °C.
  • the acrylic emulsion pressure-sensitive adhesive composition of the present invention prepared according to the above-described method exhibits excellent adhesion properties to both hydrophilic and hydrophobic substrates, and can be applied to an adhesive sheet.
  • the adhesive sheet may be a building interior and exterior material, interior materials, advertising films, or adhesive films or sheets for labels, but the present invention is not necessarily limited to these.
  • An acrylic emulsion pressure-sensitive adhesive composition was prepared by the following method using a modified polyvinyl alcohol emulsifier of Formula 1 having a number average molecular weight (Mn) of 1,000 g/mol and a hydration degree of 99% represented by Equation 1 below. .
  • the number average molecular weight was measured by gel permeation chromatography (GPC), and specifically evaluated using a Waters PL-GPC220 instrument using a Polymer Laboratories PLgel MIX-B 300 mm length column. Tetrahydrofuran was used as a solvent and the flow rate was measured at a rate of 1 mL/min. Samples were prepared at a concentration of 10 mg/10 mL, and then supplied in an amount of 20 ⁇ L. The values of Mw and Mn were derived using an assay curve formed using polystyrene standards. As for the molecular weight (g/mol) of the polystyrene standard, 8 types of 2,000 / 10,000 / 30,000 / 70,000 / 200,000 / 700,000 / 2,000,000 / 4,000,000 were used.
  • aqueous 20% by weight aqueous ammonium persulfate solution was added and dissolved by stirring for 5 minutes.
  • the pre-emulsion and 70 g of a 3% by weight aqueous ammonium persulfate solution were uniformly continuously added for a total of 5 hours and a total of 5.5 hours, respectively, and heated to 85° C. to perform an emulsion polymerization reaction.
  • the temperature was raised to 85° C. and maintained for about 1 hour to complete the reaction of unreacted monomers, and then cooled to room temperature to prepare an acrylic emulsion resin.
  • an acrylic emulsion resin was prepared in the same manner as in Example 1, except that a modified polyvinyl alcohol emulsifier having a number average molecular weight of 1,500 g/mol and a hydration degree of 78% was used.
  • an acrylic emulsion resin was prepared in the same manner as in Example 1, except that a modified polyvinyl alcohol emulsifier having a number average molecular weight of 4,000 g/mol and a hydration degree of 85% was used.
  • an acrylic emulsion resin was prepared in the same manner as in Example 1, except that a modified polyvinyl alcohol emulsifier having a number average molecular weight of 6,000 g/mol and a hydration degree of 78% was used.
  • an acrylic emulsion resin was prepared in the same manner as in Example 1, except that a modified polyvinyl alcohol emulsifier having a number average molecular weight of 7,500 g/mol and a hydration degree of 95% was used.
  • an acrylic emulsion resin was prepared in the same manner as in Example 1, except that 22 g of 30% by weight of sodium polyoxyethylene lauryl ether sulfate was used.
  • the acrylic adhesives prepared in Examples 1 to 5 and Comparative Examples 1 to 2 were respectively coated on a silicone coated release paper, and dried in an oven at 120° C. for 1 minute so that the adhesive resin coating layer had a thickness of 20 ⁇ m.
  • An adhesive sheet was made by laminating an adhesive resin coated on silicone release paper with art paper. The adhesive sheet was cut to a size of 25 mm ⁇ 200 mm to prepare an adhesive tape specimen.
  • the specimens prepared above were measured according to FTM 9 in the FINAT test method.
  • the adhesive sheet prepared above was measured according to FTM 9 among the FINAT test methods.
  • the acrylic emulsion pressure-sensitive adhesive composition of the present invention while using a polymer emulsifier having the structure of Formula 1, compared to Comparative Example 1 using a single-molecule emulsifier, while showing excellent adhesion and peel strength to the hydrophobic substrate It can be confirmed that the residual ratio is remarkably low.

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

La présente invention concerne une composition adhésive sensible à la pression d'émulsion acrylique. Selon la présente invention, il est possible de fournir une composition adhésive sensible à la pression ayant moins de résidus et présentant une excellente adhérence à la fois à des substrats hydrophobes et hydrophiles.
PCT/KR2019/011396 2018-12-18 2019-09-04 Composition adhésive sensible à la pression d'émulsion acrylique Ceased WO2020130285A1 (fr)

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US16/963,712 US20210079271A1 (en) 2018-12-18 2019-09-04 Acrylic Emulsion Pressure-Sensitive Adhesive Composition
EP19899654.8A EP3722387B1 (fr) 2018-12-18 2019-09-04 Composition adhésive sensible à la pression d'émulsion acrylique

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