WO2015041403A1 - 아크릴계 에멀젼 점착제 및 이의 제조방법 - Google Patents
아크릴계 에멀젼 점착제 및 이의 제조방법 Download PDFInfo
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- WO2015041403A1 WO2015041403A1 PCT/KR2014/006753 KR2014006753W WO2015041403A1 WO 2015041403 A1 WO2015041403 A1 WO 2015041403A1 KR 2014006753 W KR2014006753 W KR 2014006753W WO 2015041403 A1 WO2015041403 A1 WO 2015041403A1
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- acrylic emulsion
- acrylate
- meth
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- sensitive adhesive
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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
-
- 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
- C08F220/40—Esters of unsaturated alcohols, e.g. allyl (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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
-
- 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
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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
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
- C09J133/12—Homopolymers or copolymers of methyl methacrylate
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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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
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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
- 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]
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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
- 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
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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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
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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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
Definitions
- the present invention relates to an acrylic emulsion pressure sensitive adhesive and its preparation method.
- the pressure-sensitive adhesive As the pressure-sensitive adhesive, the conventional oil-based adhesive is discharged in the air for a long time after construction, so that people living in the building headache, irritation of eyes, nose, throat, cough, itching, dizziness, fatigue, reduced concentration Symptoms, and prolonged exposure causes problems with Sick House Syndrome, which causes respiratory disease, heart disease, and cancer.
- the aqueous emulsion pressure sensitive adhesive can use a polymer having a higher molecular weight than the solvent-based polymer because the viscosity of the pressure-sensitive adhesive and the molecular weight of the dispersion polymer can be used, and a wide range of solid content can be obtained, and the aging resistance is small, low viscosity and low It has the advantage of good adhesion in the solid content region and good compatibility with other polymers.
- the drying speed is low, the adhesion to hydrophobic adhesive surfaces and non-porous adherends is low, the selection range of the curing agent is narrow, and the initial adhesive strength is not only poor, but also emulsification And since it contains a dispersant, it does not reach the physical properties of the oil-based pressure-sensitive adhesive, such as low water resistance, and can not be replaced quickly.
- the polymerization method for producing the resin of the acrylic emulsion pressure-sensitive adhesive is divided into a solution type and an emulsion polymerization type.
- the solution type has the advantage that it is easy to control the reaction conditions of the polymerization and has a high efficiency in producing a uniform polymer, but because the solvent is used, the molecular weight of the polymer is lower than that of other polymerization methods, There is a limit to the use of a solvent which is slow and inevitably reduces the chain transfer by the solvent.
- emulsion emulsions are economical due to their high affinity for water, do not require post-treatment processes, the reaction is terminated within a few hours, and the conversion rate is nearly 100%. Is being manufactured.
- the aqueous emulsion pressure sensitive adhesive synthesized by the emulsion polymerization type contains hydrophilic substances such as surfactants, buffers, and water-soluble initiators in addition to the mixed monomers.
- the surfactants that impart stability to the acrylic emulsion resin are those of the adhesive resin after coating. It exists on the surface to reduce the adhesive force to the adherend, and during the coating to hinder the fusion between the acrylic emulsion resin particles in the adhesive to reduce the cohesive force.
- a method of adding a wetting agent that lowers the surface tension of the adhesive as an additive and improves the wettability on the surface of the silicone release paper is used.
- sodium dioctyl Sulfosuccinate is known as an additive having a great effect of improving coating properties.
- the wetting agent typified by sodium dioctyl sulfosuccinate also has a limitation in use as it causes problems such as generating aggregates and increasing the viscosity to lower physical properties.
- the present invention aims to solve the problems of the prior art as described above and the technical problems that have been requested from the past.
- the inventors of the present application after in-depth study and various experiments, when diacetone acrylamide and adipic acid dihydrazide are adjusted to a certain content and content ratio, the acrylic emulsion pressure-sensitive adhesive for advertising materials It was confirmed that the adhesiveness can be improved due to the effect of increasing the cohesion force, aging cohesion force and water resistance without deterioration of the existing adhesive properties generated when used, and came to complete the present invention.
- the acrylic emulsion pressure sensitive adhesive is selected from the group consisting of (a) i) a (meth) acrylic acid ester monomer having an alkyl group having 1 to 14 carbon atoms, ii) allyl ester, vinyl ester, unsaturated acetate and unsaturated nitrile.
- Mixed monomers comprising at least one monomer, iii) at least one monomer selected from the group consisting of unsaturated carboxylic acids and hydroxyl-containing unsaturated monomers, and iv) diacetone acrylamide;
- an acrylic emulsion resin produced by polymerization of a crosslinking agent, and (b) adipic acid dihydrazide.
- the term “mixed monomer” is not particularly limited as long as the acrylic emulsion resin is polymerized based on the monomers.
- the monomers may be added and polymerized in a mixed state.
- the monomers can be added sequentially and polymerized.
- the diacetone acrylamide is rapidly polymerized with various kinds of comonomers to form a copolymer, and in particular, the diacetone acrylamide reacts with a ketone group of adipic dihydrazide even at room temperature, and thus, to the acrylic emulsion resin Adipic acid dihydrazide may be added to synthesize an acrylic emulsion pressure sensitive adhesive.
- the acrylic emulsion resin of (a) is based on the total weight of the emulsion resin i) 60 to 90% by weight of (meth) acrylic acid ester monomer having an alkyl group of 1 to 14 carbon atoms, ii) allyl ester , 5 wt% to 30 wt% of at least one monomer selected from the group consisting of vinyl esters, unsaturated acetates and unsaturated nitriles, iii) 0.5 wt% of at least one monomer selected from the group consisting of unsaturated carboxylic acids and hydroxyl-containing unsaturated monomers To 5 wt%, iv) diacetone acrylamide 0.1 wt% to 1.0 wt%, and 0.1 wt% to 4.5 wt% crosslinking agent.
- the diacetone acrylamide may be included in 0.1 parts by weight to 1.0 parts by weight based on 100 parts by weight of the total monomer of the acrylic emulsion resin except diacetone acrylamide and adipic acid dihydrazide
- Acid dihydrazide may be included in an amount of 0.02 part by weight to 1.0 part by weight based on 100 parts by weight of the total monomers of the acrylic emulsion resin except diacetone acrylamide and adipic acid dihydrazide. If the diacetone acrylamide and adipic dihydrazide content is less than the above numerical range, the effect of the diacetone acrylamide and adipic dihydrazide is less than the numerical range. It is not preferable because the initial adhesive force and peeling force is lowered.
- the adipic acid dihydrazide may be included in 0.2 to 1.0 (weight ratio) compared to diacetone acrylamide, and if the content is less than 0.2 compared to diacetone acrylamide, the effect may not be sufficiently exhibited. If the physical properties are lowered, the initial adhesive strength and the peeling force is lowered if it exceeds 1.0, and even if the content ratio is increased, the degree of improvement of the adhesive properties is small and the coating property is deteriorated, which is not preferable.
- the acrylic emulsion pressure sensitive adhesive of the present invention is added to the acrylic emulsion resin containing diacetone acrylamide in a constant content ratio, so that adipic acid dihydrazide is added in a constant content ratio, so that deterioration of physical properties of the conventional acrylic emulsion pressure sensitive adhesive is not caused. It is possible to provide better adhesion properties without.
- the monomers of i) provide viscosity and adhesion properties, such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (Meth) acrylate, isobutyl acrylate, t-butyl methacrylate, pentyl methacrylate, hexyl methacrylate, heptyl acrylate, isooctyl acrylate, octyl methacrylate, 2-ethylhexyl (meth) acrylic It may be one or more selected from the group consisting of latex, isodecyl acrylate, decyl methacrylate, dodecyl methacrylate, isobornyl methacrylate, and lauryl (meth) acrylate, these may be mixed alone or two or more Can be used.
- it may be a mixture of 30 wt% to 60 wt% of 2-ethylhexyl acrylate and 40 wt% to 70 wt% of butylacrylate based on the total weight of the (meth) acrylic acid ester monomer.
- the monomer of i) may be included in an amount of 60% by weight to 90% by weight based on the total weight of the emulsion resin, and when included in less than 60% by weight, the initial adhesive strength of the acrylic emulsion pressure sensitive adhesive may be ensured. If it is included in excess of 90% by weight, it is not preferable because the interfacial breakage occurs between the adherend and the pressure-sensitive adhesive upon removal after use.
- the number of carbon atoms of the alkyl group of i) may be 1 to 14 in detail, more specifically may be 2 to 14 bar, when less than 1, the cohesive strength of the acrylic emulsion pressure-sensitive adhesive is less than, more than 14 In this case, the acrylic emulsion pressure-sensitive adhesive is too soft, it is not preferable because the adhesive properties are poor.
- the monomer of ii) may be at least one selected from the group consisting of vinyl acetate, vinyl butane, vinyl propionate, vinyl lauryl acid, vinyl pyrrolidone, acrylonitrile and methacrylonitrile, In particular, it may be vinyl acetate, vinyl butane or acrylonitrile.
- the monomer of ii) may be included in an amount of 5 wt% to 30 wt% based on the total weight of the emulsion resin, and in detail, may be included in an amount of 7 wt% to 25 wt%, and less than 5 wt%.
- the acrylic emulsion pressure sensitive adhesive is too flexible to secure sufficient adhesive properties, and when included in excess of 30% by weight, the acrylic emulsion pressure sensitive adhesive is excessively hardened to cause a significant decrease in adhesive force, which is not preferable.
- the monomer of iii) is acrylic acid, itaconic acid, maleic anhydride, fumaric acid, crotanic acid methacrylic acid, ethyl methacrylic acid, hydroxymethyl (meth) acrylate, hydroxyethyl (meth) acrylate , Hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, hydroxyhexyl (meth) acrylate, hydroxyoctyl (meth) acrylate, hydroxylauryl (meth) acrylate and hydroxypropylene It may be one or more selected from the group consisting of glycol (meth) acrylate.
- the monomer of iii) may be included in an amount of 0.5% by weight to 5% by weight based on the total weight of the emulsion resin, and when it is included in less than 0.5% by weight, the acrylic emulsion pressure sensitive adhesive becomes too flexible to provide sufficient adhesive properties. When it cannot be secured and it contains more than 5 weight%, since an acrylic emulsion adhesive becomes excessively hard and a remarkable fall of adhesive force arises, it is unpreferable.
- diacetone acrylamide (the iv) may be further included in the mixed monomer for preparing the acrylic emulsion resin, and in this case, the diacetone acrylamide is diacetone acrylamide and adipic acid dihydra. 0.1 wt% to 1.0 wt% based on the total weight of the acrylic emulsion resin except for Zide, and the acrylic emulsion resin provides more improved cohesion within the above range.
- the crosslinking agent is added to reinforce the cohesion, and may include 5 to 15 alkylene oxide groups, and in detail, may include 6 to 12, all of the room temperature and aging tackiness, stability within the above range Excellent effect.
- the number of the alkylene oxide groups means the average number of alkylene oxide groups included in the crosslinking agent used, and when the crosslinking agent is less than five alkylene oxide groups, the pressure-sensitive adhesive prepared is more than necessary, the initial adhesive strength It is not preferable because the pressure-sensitive adhesive to be prepared is more than 15 alkylene oxide groups, because the pressure-sensitive adhesive is softened more than necessary to reduce the adhesive physical properties.
- the crosslinking agent is an organic crosslinking agent such as polyethylene glycol diacrylate, polypropylene glycol diacrylate, 1,6-hexanediol diacrylate, trimethylol propane triacrylate, ethoxylated trimethylpropane triacrylate, Tripropylene glycol diacrylate, 1,3-butanediol diacrylate, pentatritoltriacrylate, 3-trimethoxysilyl propylmethacrylate, vinyltrimethoxysilane and divinylbenzene, and the like, aluminum acetyl which is an inorganic crosslinking agent It may be at least one selected from the group consisting of acetonate, zinc acetate, zirconium carbonate, and the like, and in detail, at least one selected from the group consisting of polyethylene glycol diacrylate and polypropylene glycol diacrylate.
- organic crosslinking agent such as polyethylene glycol diacrylate, polypropylene glycol diacrylate, 1,6-
- the present invention also discloses a method for producing the acrylic emulsion pressure sensitive adhesive.
- the method for preparing the acrylic emulsion pressure-sensitive adhesive is based on the total weight of the acrylic emulsion resin of (A) i) 60% to 90% by weight of (meth) acrylic acid ester monomer having an alkyl group of 1 to 14 carbon atoms, ii) allyl ester, vinyl 5% to 30% by weight of one or more monomers selected from the group consisting of esters, unsaturated acetates and unsaturated nitriles, iii) 0.5% to 5% by weight of one or more monomers selected from the group consisting of unsaturated carboxylic acids and hydroxyl-containing unsaturated monomers Wt%, and iv) polymerizing 0.1 wt% to 1.0 wt% diacetone acrylamide with 0.1 wt% to 4.5 wt% crosslinking agent to prepare an acrylic emulsion resin; (B) adding adipic acid dihydrazide to the acrylic emulsion resin prepared in step (A) and stirring to prepare an acrylic
- the polymerization reaction of the mixed monomer and the crosslinking agent, the process (A) is not particularly limited, but emulsion polymerization that is easy to control the heat of reaction is preferable, and in detail, the water, electrolyte and surfactant may be First step of preparing a solution by removing the oxygen and dissolving the initiator by heating to 80 ° C .; I) 60 to 90 weight percent of (meth) acrylic acid ester monomers having alkyl groups of 1 to 14 carbon atoms based on the total weight of the emulsion resin, ii) allyl esters, vinyl esters, unsaturated acetates and unsaturated nitriles 5 wt% to 30 wt% of at least one monomer, iii) 0.5 wt% to 5 wt% of at least one monomer selected from the group consisting of unsaturated carboxylic acids and hydroxyl-containing unsaturated monomers, and iv) 0.1 wt% to di
- the initiator may be a water-soluble polymerization initiator such as persulfate of ammonium or an alkali metal, hydrogen peroxide, peroxide, hydroxide peroxide, or the like, and may be used together with one or more reducing agents to conduct an emulsion polymerization reaction at low temperature.
- the reducing agent may be sodium bisulfite, sodium metabisulfite, sodium hydrosulfite, sodium thiosulfate, sodium formaldehyde sulfoxylate, ascorbic acid, and the like.
- the temperature of the polymerization reaction may be in detail 0 ° C to 100 ° C, more specifically in consideration of the physical properties of the pressure-sensitive adhesive may be 40 ° C to 90 ° C, the initiator alone or one of the initiator and the reducing agent It can be adjusted by the method of mixing and using a species or more.
- the electrolyte used in the polymerization reaction is to adjust the pH and impart stability to the acrylic emulsion resin to be polymerized, specifically 1 selected from the group consisting of sodium bicarbonate, sodium carbonate, sodium phosphate, sodium sulfate, sodium chloride, and the like. It may be a species or more, specifically sodium carbonate.
- the surfactant is used for the initial particle generation during the polymerization reaction, the size control of the generated particles and the stability of the particles, and is composed of a hydrophilic group and a lipophilic group, and is divided into anionic, cationic and nonionic surfactants.
- anionic and nonionic surfactants are used a lot, and they may be mixed with each other to compensate for mechanical stability and chemical stability.
- the anionic surfactant may be sodium alkyldiphenyloxide disulfonate, sodium polyoxyethylene alkyl ether sulfate, sodium polyoxyethylene lauryl ether sulfate, sodium dialkyl sulfosuccinate, and the like.
- the acrylic emulsion resin may have an acidity (pH) adjusted as an alkaline material, and the pH of the acrylic emulsion resin may be 6 to 9 in detail, and more specifically 7 to 8, and the alkaline material may be a monovalent metal or Inorganic substances such as hydroxides, chlorides, carbonates of divalent metals, ammonia, organic amines, and the like.
- the present invention provides an adhesive sheet for forming the pressure-sensitive adhesive layer by applying the acrylic emulsion pressure-sensitive adhesive thus prepared on a pressure-sensitive adhesive film or sheet.
- the adhesive sheet may be, but is not limited to, an interior or exterior building material, an interior material, an advertising film, or an adhesive film or sheet of a label, and the adhesive layer may have a thickness of 10 ⁇ m to 100 ⁇ m, specifically 20 ⁇ m to 30 ⁇ m. It may be a ⁇ m, excellent coating properties and sufficient adhesive properties.
- the pH was adjusted to 7 to 8 by adding 28% aqueous ammonia solution to the acrylic emulsion resin.
- Example 1 18.75 g of 20% diacetone acrylamide was prepared in preparing the acrylic emulsion resin, and 7.5 g of 10% adipic acid dihydrazide was used in preparing the acrylic emulsion adhesive.
- Example 1 18.75 g of 20% diacetone acrylamide was prepared in preparing the acrylic emulsion resin, and 37.5 g of 10% adipic dihydrazide was used in preparing the acrylic emulsion adhesive.
- Example 1 37.5 g of 20% diacetone acrylamide was prepared in preparing the acrylic emulsion resin, and 15 g of 10% adipic acid dihydrazide was used in preparing the acrylic emulsion adhesive.
- Example 1 37.5 g of 20% diacetone acrylamide was prepared in preparing the acrylic emulsion resin, and 75 g of 10% adipic acid dihydrazide was prepared in the preparation of the acrylic emulsion adhesive.
- Diacetone acrylamide and acrylic emulsion pressure-sensitive adhesive when preparing the acrylic emulsion resin in Example 1 was carried out in the same manner except that adipic acid dihydrazide was not used.
- Example 1 6 g of 20% diacetone acrylamide was prepared in preparing the acrylic emulsion resin, and 6 g of 10% adipic dihydrazide was used in preparing the acrylic emulsion adhesive.
- Example 1 In Example 1, except that 90 g of 20% diacetone acrylamide was prepared in preparing the acrylic emulsion resin and 90 g of 10% adipic acid dihydrazide was used in preparing the acrylic emulsion adhesive.
- Example 1 18.75 g of 20% diacetone acrylamide was prepared in preparing the acrylic emulsion resin, and 6.75 g of 10% adipic acid dihydrazide was used in the preparation of the acrylic emulsion adhesive.
- Example 1 18.75 g of 20% diacetone acrylamide was prepared in preparing the acrylic emulsion resin, and 45 g of 10% adipic acid dihydrazide was used in preparing the acrylic emulsion adhesive.
- Example 1 37.5 g of 20% diacetone acrylamide was prepared in preparing the acrylic emulsion resin, and 13.5 g of 10% adipic acid dihydrazide was prepared in the preparation of the acrylic emulsion adhesive.
- Example 1 37.5 g of 20% diacetone acrylamide was prepared in preparing the acrylic emulsion resin, and 90 g of 10% adipic acid dihydrazide was used in preparing the acrylic emulsion adhesive.
- DAAM diacetone acrylamide
- ADH adipic acid dihydrazide
- Table 1 Content (parts by weight) Content ratio (ADH / DAAM) DAAM ADH
- the acrylic emulsion pressure-sensitive adhesive was applied on a release coated paper coated with silicone, and dried in an oven at 120 ° C. for 1 minute so that the acrylic emulsion pressure-sensitive adhesive layer had a thickness of 20 ⁇ m.
- % Of agglomerate (weight before drying-weight after drying) / weight before drying ⁇ 100
- Example 1 350 9.0 12.2 25.9 17.9 8.3
- Example 2 330 9.1 12.3 23.0 15.7 7.5
- Example 3 380 8.7 11.8 29.5 20.1 8.8
- Example 4 320 9.1 12.1 23.7 16.5 7.7
- Example 5 330 8.9 12.0 25.0 17.3 7.8
- Example 6 350 9.0 12.0 24.5 17.0 7.9
- Example 7 340 8.8 11.9 27.7 18.3 8.1 Comparative Example 1 350 9.2 12.5 15.5 7.3 5.7 Comparative Example 2 340 9.1 12.2 17.0 7.9 5.5 Comparative Example 3 330 9.0 12.3 15.9 7.2 5.5 Comparative Example 4 350 9.2 12.3 19.5 10.0 6.0
- Examples 1 to 7 can be seen that the cohesive force, aging cohesion force and the water-resistant adhesive force is improved without other physical properties of the existing, the overall physical properties are excellent.
- Comparative Example 1 does not use diacetone acrylamide and adipic acid dihydrazide
- Comparative Example 2 does not use diacetone acrylamide
- Comparative Example 3 is adipic acid dihydrazide As not used. It can be seen that cohesion, aging cohesion and water resistance are not good as compared with the examples.
- Comparative Examples 4 to 5 used diacetone acrylamide and adipic acid dihydrazide as in Example, but the use content is out of the set content of the present invention, the effect is sufficiently exhibited when the content is small. It was confirmed that cohesion, aging cohesion, and water-resistant cohesion were not good, and in many cases, agglomerates were generated during polymerization, and the initial cohesion and peeling force were lowered.
- Comparative Examples 6 to 9 is a case where the content ratio of diacetone acrylamide and adipic acid dihydrazide is out of the set content of the present invention.
- the content ratio is too small, the effects are not sufficiently exhibited, and thus the cohesion, aging cohesion and water resistance If the adhesion is not good, on the contrary, if the content ratio is too high, the initial adhesive force and peeling force are lowered, and even if the content ratio is increased, the degree of improvement in cohesion, aging cohesion and water-resistance is low, and the coating property is deteriorated. Confirmed.
- the present invention can provide an acrylic emulsion pressure-sensitive adhesive excellent in cohesive force, aging cohesion force and water adhesion strength without deterioration of adhesive physical properties.
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Abstract
Description
함량 (중량부) | 함량비(ADH/DAAM) | |||
DAAM | ADH | |||
실시예 | 1 | 0.5 | 0.25 | 0.5 |
2 | 0.1 | 0.05 | 0.5 | |
3 | 1.0 | 0.5 | 0.5 | |
4 | 0.25 | 0.05 | 0.2 | |
5 | 0.25 | 0.25 | 1.0 | |
6 | 0.5 | 0.1 | 0.2 | |
7 | 0.5 | 0.5 | 1.0 | |
비교예 | 1 | - | - | - |
2 | 0.5 | - | - | |
3 | - | 0.25 | - | |
4 | 0.08 | 0.04 | 0.5 | |
5 | 1.2 | 0.6 | 0.5 | |
6 | 0.25 | 0.045 | 0.18 | |
7 | 0.25 | 0.3 | 1.2 | |
8 | 0.5 | 0.09 | 0.18 | |
9 | 0.5 | 0.6 | 1.2 |
구 분 | 응집물함량(ppm) | 초기점착력(N/in) | 180도박리력(N/in) | 응집력(시간) | 노화응집력(시간) | 내수점착력(N/in) |
실시예 1 | 350 | 9.0 | 12.2 | 25.9 | 17.9 | 8.3 |
실시예 2 | 330 | 9.1 | 12.3 | 23.0 | 15.7 | 7.5 |
실시예 3 | 380 | 8.7 | 11.8 | 29.5 | 20.1 | 8.8 |
실시예 4 | 320 | 9.1 | 12.1 | 23.7 | 16.5 | 7.7 |
실시예 5 | 330 | 8.9 | 12.0 | 25.0 | 17.3 | 7.8 |
실시예 6 | 350 | 9.0 | 12.0 | 24.5 | 17.0 | 7.9 |
실시예 7 | 340 | 8.8 | 11.9 | 27.7 | 18.3 | 8.1 |
비교예 1 | 350 | 9.2 | 12.5 | 15.5 | 7.3 | 5.7 |
비교예 2 | 340 | 9.1 | 12.2 | 17.0 | 7.9 | 5.5 |
비교예 3 | 330 | 9.0 | 12.3 | 15.9 | 7.2 | 5.5 |
비교예 4 | 350 | 9.2 | 12.3 | 19.5 | 10.0 | 6.0 |
비교예 5 | 470 | 7.9 | 11.0 | 29.8 | 20.2 | 8.8 |
비교예 6 | 370 | 9.2 | 12.2 | 20.0 | 11.0 | 6.3 |
비교예 7 | 320 | 8.5 | 11.7 | 24.5 | 17.0 | 7.5 |
비교예 8 | 350 | 8.9 | 12.1 | 21.2 | 12.5 | 6.8 |
비교예 9 | 340 | 8.2 | 11.3 | 27.0 | 17.9 | 7.9 |
Claims (15)
- (A) i) 탄소수 1 내지 14의 알킬기를 가진 (메타)아크릴산 에스테르 단량체, ii) 알릴 에스테르, 비닐 에스테르, 불포화 아세테이트 및 불포화 니트릴로 이루어진 군으로부터 선택되는 1종 이상의 단량체, iii) 불포화 카본산 및 수산기 함유 불포화 단량체로 이루어진 군으로부터 선택되는 1종 이상의 단량체, 및 iv) 디아세톤 아크릴아마이드를 포함하는 혼합 단량체; 및가교제의 중합으로 생성된 아크릴계 에멀젼 수지와,(b) 아디프산 디하이드라자이드를 포함하는 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 1 항에 있어서, 아디프산 디하이드라자이드는 상기 에멀젼 수지와 반응을 통해 결합되는 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 1 항에 있어서, 상기 (A)의 아크릴계 에멀젼 수지는 에멀젼 수지 전체 중량을 기준으로 i) 탄소수 1 내지 14의 알킬기를 가진 (메타)아크릴산 에스테르 단량체 60 중량% 내지 90 중량%, ii) 알릴 에스테르, 비닐 에스테르, 불포화 아세테이트 및 불포화 니트릴로 이루어진 군으로부터 선택되는 1종 이상의 단량체 5 중량% 내지 30 중량%, iii) 불포화 카본산 및 수산기 함유 불포화 단량체로 이루어진 군으로부터 선택되는 1종 이상의 단량체 0.5 중량% 내지 5 중량%, iv) 디아세톤 아크릴아마이드 0.1 중량% 내지 1.0 중량%, 및 가교제 0.1 중량% 내지 4.5 중량%를 포함하여 중합되어지는 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 1 항에 있어서, 상기 디아세톤 아크릴아마이드는, 디아세톤 아크릴아마이드 및 아디프산 디하이드라자이드를 제외한 아크릴계 에멀젼 수지의 전체 단량체 100 중량부에 대해 0.1 내지 1.0 중량부로 포함되는 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 1 항에 있어서, 상기 아디프산 디하이드라자이드는, 디아세톤 아크릴아마이드 및 아디프산 디하이드라자이드를 제외한 아크릴계 에멀젼 수지의 전체 단량체 100 중량부에 대해 0.02 중량부 내지 1.0 중량부로 포함되는 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 1 항에 있어서, 상기 아디프산 디하이드라자이드는 디아세톤 아크릴아마이드 대비 0.2 내지 1.0(중량비)로 포함되는 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 1 항에 있어서, 상기 i)의 단량체는 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 프로필(메타)아크릴레이트, 이소프로필(메타)아크릴레이트, 부틸(메타)아크릴레이트, 이소부틸아크릴레이트, t-부틸메타크릴레이트, 펜틸메타크릴레이트, 헥실메타크릴레이트, 헵틸아크릴레이트, 이소옥틸아크릴레이트, 옥틸메타크릴레이트, 2-에틸헥실(메타)아크릴레이트, 이소데실아크릴레이트, 데실메타크릴레이트, 도데실메타크릴레이트, 이소보닐메타크릴레이트, 및 라우릴(메타)아크릴레이트로 이루어진 군으로부터 선택되는 하나 이상인 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 1 항에 있어서, 상기 i)의 단량체는 (메타)아크릴산 에스테르 단량체 전체 중량을 기준으로 부틸아크릴레이트 40 중량% 내지 70중량% 및 2-에틸헥실 아크릴레이트 30 중량% 내지 60 중량%의 혼합물로 이루어지는 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 1 항에 있어서, 상기 ii)의 단량체는 아세트산 비닐, 부탄산 비닐, 프로피온산 비닐, 라우릴산 비닐, 비닐 피롤리돈, 아크릴로니트릴 및 메타크릴로니트릴로 이루어진 군으로부터 선택되는 하나 이상인 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 1 항에 있어서, 상기 iii)의 단량체는 아크릴산, 이타콘산, 무수말레인산, 푸마르산, 크로탄산 메타크릴산, 에틸메타크릴산, 히드록시메틸(메타)아크릴레이트, 하드록시에틸(메타)아크릴레이트, 히드록시프로필(메타)아크릴레이트, 히드록시부틸(메타)아크릴레이트, 히드록시헥실(메타)아크릴레이트, 히드록시옥틸(메타)아크릴레이트, 히드록시라우릴(메타)아크릴레이트 및 히드록시프로필렌글리콜(메타)아크릴레이트로 이루어진 군으로부터 선택되는 하나 이상인 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 1 항에 있어서, 상기 가교제는 5 내지 15개의 알킬렌 옥사이드기를 포함하고, 아크릴레이트기 또는 비닐기를 가진 화합물인 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 11 항에 있어서, 상기 가교제는 폴리에틸렌글리콜디아크릴레이트 및 폴리프로필렌글리콜디아크릴레이트로 이루어진 군으로부터 선택되는 1종 이상인 것을 특징으로 하는 아크릴계 에멀젼 점착제.
- 제 1 항에 따른 아크릴계 에멀젼 점착제의 제조방법에 있어서,(A)의 아크릴계 에멀젼 수지는 에멀젼 수지 전체 중량을 기준으로 i) 탄소수 1 내지 14의 알킬기를 가진 (메타)아크릴산 에스테르 단량체 60 내지 90 중량%, ii) 알릴 에스테르, 비닐 에스테르, 불포화 아세테이트 및 불포화 니트릴로 이루어진 군으로부터 선택되는 1종 이상의 단량체 5 내지 30 중량%, iii) 불포화 카본산 및 수산기 함유 불포화 단량체로 이루어진 군으로부터 선택되는 1종 이상의 단량체 0.5 중량% 내지 5 중량%, 및 iv) 디아세톤 아크릴아마이드 0.1 중량% 내지 1.0 중량%와, 가교제 0.1 중량% 내지 4.5 중량%를 중합하여 아크릴계 에멀젼 수지를 제조하는 과정;(B) 상기 과정(A)에서 제조된 아크릴계 에멀젼 수지에 아디프산 디하이드라자이드를 투입하고 교반하여 아크릴계 에멀젼 점착제를 제조하는 과정;을 포함하는 것을 특징으로 하는 방법.
- 제 13 항에 있어서, 상기 과정(A)는,물, 전해질 및 계면 활성제를 반응기에 투여하고 80℃로 승온시켜 산소를 제거하고 개시제를 용해시켜 용액을 제조하는 제 1 과정;에멀전 수지 전체 중량을 기준으로 i) 탄소수 1 내지 14의 알킬기를 가진 (메타)아크릴산 에스테르 단량체 60 내지 90 중량%, ii) 알릴 에스테르, 비닐 에스테르, 불포화 아세테이트 및 불포화 니트릴로 이루어진 군으로부터 선택되는 1종 이상의 단량체 5 중량% 내지 30 중량%, iii) 불포화 카본산 및 수산기 함유 불포화 단량체로 이루어진 군으로부터 선택되는 1종 이상의 단량체 0.5 중량% 내지 5 중량%, 및 iv) 디아세톤 아크릴아마이드 0.1 중량% 내지 1.0 중량%와, 가교제 0.1 중량% 내지 4.5 중량%를 혼합한 단량체 혼합물에 물, 전해질 및 계면 활성제를 투여하여 유화액을 제조하는 제 2 과정;상기 제 1 과정의 용액에 제 2 과정의 유화액 및 개시제를 연속 투입하고, 80℃로 승온 후 상온 냉각시켜 아크릴계 에멀젼 수지를 제조하는 제 3 과정; 및상기 아크릴계 에멀젼 수지의 pH를 6 내지 9로 조절하는 제 4 과정;으로 구성된 것을 특징으로 하는 아크릴계 에멀젼 점착제 제조방법.
- 제 1 항 내지 제 12 항 중 어느 하나에 따른 아크릴계 에멀젼 점착제를 점착용 필름 또는 시트상에 부가하여 점착제 층을 형성하는 점착시트.
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CN105531340B (zh) | 2018-09-18 |
CN105531340A (zh) | 2016-04-27 |
JP6194118B2 (ja) | 2017-09-06 |
KR20150033008A (ko) | 2015-04-01 |
JP2016529379A (ja) | 2016-09-23 |
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