WO2013024980A1 - Hot melt composition - Google Patents

Hot melt composition Download PDF

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Publication number
WO2013024980A1
WO2013024980A1 PCT/KR2012/006030 KR2012006030W WO2013024980A1 WO 2013024980 A1 WO2013024980 A1 WO 2013024980A1 KR 2012006030 W KR2012006030 W KR 2012006030W WO 2013024980 A1 WO2013024980 A1 WO 2013024980A1
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Prior art keywords
hot melt
melt adhesive
adhesive composition
aliphatic polycarbonate
oxide
Prior art date
Application number
PCT/KR2012/006030
Other languages
French (fr)
Inventor
Seung Gweon Hong
Min Ho Jeon
Kwang Jin Chung
Ki Nam Chung
Myung Ahn Ok
In Hun Son
Original Assignee
Sk Innovation Co.,Ltd.
Sk Global Chemical Co., Ltd.
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 Sk Innovation Co.,Ltd., Sk Global Chemical Co., Ltd. filed Critical Sk Innovation Co.,Ltd.
Priority to CN201280040327.0A priority Critical patent/CN103842464A/en
Priority to JP2014525917A priority patent/JP2014527565A/en
Priority to EP12823800.3A priority patent/EP2744867A4/en
Priority to US14/238,988 priority patent/US20140206835A1/en
Publication of WO2013024980A1 publication Critical patent/WO2013024980A1/en

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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
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/32—General preparatory processes using carbon dioxide
    • C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers
    • 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
    • C09J169/00—Adhesives based on polycarbonates; Adhesives based on derivatives of polycarbonates

Definitions

  • the present invention relates to a hot melt adhesive composition including aliphatic carbonate, and more particularly, to a hot melt adhesive composition having a lower softening point and a low melt viscosity to thereby be applicable at a relatively low temperature, having excellent adhesion, and being environmentally friendly because toxic materials are not discharged at the time of disposal.
  • a hot melt adhesive is a solid material at room temperature; however, when applying heat thereto, it is melted into a fluid state such as liquid or the like, to have adhesion to a material to be adhered. When the melted fluid state of hot melt adhesive is cooled, it is recovered to a solid state to have cohesion again.
  • the hot melted adhesive is made of a thermoplastic material, it is melted at high temperature to form a shape, which is then cooled to be rapidly adhered to the material.
  • the hot melt adhesive mainly uses the Van der Waals force and a polarity combination on a surface thereof to adhere the adhesive and a material to be adhered to each other.
  • the adhesive strength is influenced by an anchoring effect in which a liquid adhesive flows into a hole or an uneven portion to increase the adhesive strength.
  • the hot melt adhesive needs to have enough flowability when being melted. For this, the hot melt adhesive needs to be melted at temperature as high as possible.
  • An ordinary hot melt adhesive of the related art mainly employs ethylenevinylacetate (EVA), which has been widely used for adhesion of a paperboard box, a construction interior material, or the like.
  • EVA ethylenevinylacetate
  • the microwax included in the EVA serves to adjust melting viscosity.
  • the hot melt adhesive having the enough flowability and the high adhesive strength at a low melting temperature provides a high energy efficiency at the time of application and do not need to use a solvent according to the adhesive strength, which is an advantage of the hot melt, such that it is environmentally friendly.
  • a resin having pyrolysis temperature lower than that of the hot melt adhesive of the related art is used, a cost of treating waste after use may be decreased, which have economical and environmental benefits.
  • An object of the present invention is to provide a hot melt adhesive capable of having high polarity to thereby improve adhesive strength to a paper, wood, a metal, or the like, and having a low pyrolysis temperature and not generating any harmful gas when combusted, to thereby lower energy consumption at the time of waste treatment and generate less air pollution, and thus be environmentally friendly.
  • the present invention provides a hot melt adhesive composition including aliphatic polycarbonate.
  • the hot melt adhesive composition according to the present invention pyrolysis temperature is low, such that harmful gas is not generated at the time of waste treatment, resulting in providing an excellent environmentally friendly product.
  • the hot melt adhesive composition has a low melting temperature to thereby be usable at a low temperature and exhibit sufficient adhesive strength.
  • the present invention provides a hot melt adhesive composition including the aliphatic polycarbonate, and the aliphatic polycarbonate is obtained by reacting carbon dioxide and at least one different epoxide compound.
  • the epoxide compound are at least one selected from the group consisting of (C2-C10)alkylene oxide substituted or unsubstituted with halogen or alkoxy; (C4-C20)cycloalkyleneoxide substituted or unsubstituted with halogen or alkoxy; and (C8-C20)styreneoxide substituted or unsubstituted with halogen, alkoxy, alkyl, or aryl.
  • alkoxy may include alkyloxy, aryloxy, aralkyloxy, and the like, and examples of the aryloxy may include phenoxy, biphenyloxy, naphthyloxy, and the like.
  • the alkoxy, alkyl, and aryl may have a substituent selected from a halogen atom or an alkoxy group.
  • aliphatic polycarbonate may be represented by Chemical Formula 1 below:
  • epoxide compound according to the present invention may include ethylene oxide, propylene oxide, butene oxide, pentene oxide, hexene oxide, octene oxide, decene oxide, dodecene oxide, tetradecene oxide, hexadecene oxide, octadecene oxide, butadiene monoxide, 1,2-epoxide-7-octene, epifluorohydrine, epichlorohydrine, epibromohydrine, isopropyl glycidyl ether, butyl glycidyl ether, t-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, allyl glycidyl ether, cyclopentene oxide, cyclohexene oxide, cyclooctene oxide, cyclododecene oxide, alpha-pinene oxide, 2,3-ep
  • An example of a method of producing the aliphatic polycarbonate may include a solution polymerization method or a bulk polymerization method. More specifically, polymerization may be performed by feeding carbon dioxide in the presence of the epoxide compound and a catalyst while using an organic solvent as a reactive medium.
  • organic solvent aliphatic hydrocarbons such as pentane, octane, decane, cyclohexane, and the like; aromatic hydrocarbons such as benzene, toluene, xylene, and the like; and halogenated hydrocarbons such as chloromethane, methylenechloride, chloroform, carbontetrachloride, 1,1-dichloroethane, 1,2-dichloethane, ethylchloride, trichloroethane, 1-chloropropane, 2-chloropropane, 1-chlorobutane, 2-chlorobutane, 1-chloro-2-methylpropane, chlorobenzene, bromobenzene, and the like, may be used alone or in combination of two or more thereof.
  • aliphatic hydrocarbons such as pentane, octane, decane, cyclohexane, and the like
  • the pressure of carbon dioxide may be from normal pressure to 100 atm, and preferably, 5 atm to 30 atm.
  • the polymerization temperature at the time of copolymerization may be 20 ⁇ 120°C, and preferably, 50 ⁇ 90°C. More preferably, the bulk polymerization method using a monomer itself as a solvent may be performed.
  • the aliphatic polycarbonate is polyalkylene carbonate produced based on descriptions of Korean Patent Laid-Open Publication Nos. 2008-0015454, 2009-0090154, 2010-067593, and 2010-0013255 filed by the present applicants, and examples of the alkylene may include, but are not limited to, ethylene, propylene, 1-butylene, cyclohexene, alkylglycidylether, n-butyl, n-octyl, and the like.
  • the aliphatic polycarbonate of Chemical Formula 1 above leads to a hot melt adhesive composition having a glass transition temperature (Tg) of 40 to 110°C.
  • the hot melt adhesive composition according to the present invention has a softening point of 70 to 130°C. Hence, the hot melt adhesive composition according to the present invention has an excellent adhesive strength or viscosity despite the low softening point thereof, and thus, is favorably applied at a low temperature.
  • the residual amount of a catalyst in the aliphatic polycarbonate used in the hot melt adhesive composition is 3 ppm or less.
  • the residual amount of catalyst is minimized, such that the hot melt adhesive composition may be anticipated to have improved adhesive strength and thermal stability.
  • the pyrolysis temperature is low, such that the harmful gas is not generated at the time of waste treatment, resulting in providing an excellent environmentally friendly product.
  • the hot melt adhesive composition has the low melting temperature to thereby be usable at low temperature and exhibit sufficient adhesive strength.
  • the hot melt adhesive composition is not easily pyrolyzed when being exposed to heat, due to the low residual amount of catalyst of 3 ppm or less.
  • Polypropylene carbonate having molecular weight of 290,000 g/mol as a base resin was extruded by using a 5m-length twin extruder at a rate of 1.6 kg/h at 230°C to obtain polypropylene carbonate having a molecular weight of 50,000 g/mol.
  • the low-molecular weight polypropylene carbonate and 10 parts by weight of propylene carbonate as a plasticizer were mixed together, and the mixture was then extruded by using a twin extruder at 190°C, to be produced into a pellet.
  • the viscosity of the thus produced hot melt adhesive was 10 Pa.sec.
  • the hot melt adhesive was melted at 190°C, and then applied between a PVC sheet and wood in order to adhere them.
  • the adhesive strength measurement result is shown in Table 1 below.
  • the hot melt adhesive compositions according to Examples 1 and 2 of the present invention had softening points of 100°C and 110°C, respectively, and thus, the low melting temperatures thereof were low, such that they were usable at a low temperature and exhibited sufficient adhesive strength.
  • the hot melt adhesive composition according to the present invention can have a softening point lower than that of Comparative Example 1 and unreduced adhesive strength, thereby providing an environmentally friendly hot melt adhesive.

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

Abstract

Provided is a hot melt adhesive composition including aliphatic polycarbonate. With the hot melt adhesive composition according to the present invention, the pyrolysis temperature is low, such that the harmful gas is not generated at the time of waste treatment, resulting in providing an excellent environmentally friendly product. In addition, the hot melt adhesive composition has the low melting temperature to thereby be usable at low temperature and exhibit sufficient adhesive strength.

Description

HOT MELT COMPOSITION
The present invention relates to a hot melt adhesive composition including aliphatic carbonate, and more particularly, to a hot melt adhesive composition having a lower softening point and a low melt viscosity to thereby be applicable at a relatively low temperature, having excellent adhesion, and being environmentally friendly because toxic materials are not discharged at the time of disposal.
Generally, a hot melt adhesive is a solid material at room temperature; however, when applying heat thereto, it is melted into a fluid state such as liquid or the like, to have adhesion to a material to be adhered. When the melted fluid state of hot melt adhesive is cooled, it is recovered to a solid state to have cohesion again. In addition, since the hot melted adhesive is made of a thermoplastic material, it is melted at high temperature to form a shape, which is then cooled to be rapidly adhered to the material. The hot melt adhesive mainly uses the Van der Waals force and a polarity combination on a surface thereof to adhere the adhesive and a material to be adhered to each other. The adhesive strength is influenced by an anchoring effect in which a liquid adhesive flows into a hole or an uneven portion to increase the adhesive strength. In order to perfectly use this effect, the hot melt adhesive needs to have enough flowability when being melted. For this, the hot melt adhesive needs to be melted at temperature as high as possible.
An ordinary hot melt adhesive of the related art mainly employs ethylenevinylacetate (EVA), which has been widely used for adhesion of a paperboard box, a construction interior material, or the like. The microwax included in the EVA serves to adjust melting viscosity.
The hot melt adhesive having the enough flowability and the high adhesive strength at a low melting temperature provides a high energy efficiency at the time of application and do not need to use a solvent according to the adhesive strength, which is an advantage of the hot melt, such that it is environmentally friendly. In addition, in the case in which a resin having pyrolysis temperature lower than that of the hot melt adhesive of the related art is used, a cost of treating waste after use may be decreased, which have economical and environmental benefits.
An object of the present invention is to provide a hot melt adhesive capable of having high polarity to thereby improve adhesive strength to a paper, wood, a metal, or the like, and having a low pyrolysis temperature and not generating any harmful gas when combusted, to thereby lower energy consumption at the time of waste treatment and generate less air pollution, and thus be environmentally friendly.
In one general aspect, the present invention provides a hot melt adhesive composition including aliphatic polycarbonate.
With the hot melt adhesive composition according to the present invention, pyrolysis temperature is low, such that harmful gas is not generated at the time of waste treatment, resulting in providing an excellent environmentally friendly product. In addition, the hot melt adhesive composition has a low melting temperature to thereby be usable at a low temperature and exhibit sufficient adhesive strength.
Hereinafter, the present invention will be described in detail.
The present invention provides a hot melt adhesive composition including the aliphatic polycarbonate, and the aliphatic polycarbonate is obtained by reacting carbon dioxide and at least one different epoxide compound.
The epoxide compound are at least one selected from the group consisting of (C2-C10)alkylene oxide substituted or unsubstituted with halogen or alkoxy; (C4-C20)cycloalkyleneoxide substituted or unsubstituted with halogen or alkoxy; and (C8-C20)styreneoxide substituted or unsubstituted with halogen, alkoxy, alkyl, or aryl.
Specific examples of the alkoxy may include alkyloxy, aryloxy, aralkyloxy, and the like, and examples of the aryloxy may include phenoxy, biphenyloxy, naphthyloxy, and the like. The alkoxy, alkyl, and aryl may have a substituent selected from a halogen atom or an alkoxy group.
More specifically, the aliphatic polycarbonate may be represented by Chemical Formula 1 below:
[Chemical Formula 1]
Figure PCTKR2012006030-appb-I000001
[in Chemical Formula 1, m is an integer of 2 to 10; n is an integer of 1 to 3; R is hydrogen, (C1-C4)alkyl, or -CH2-O-R' (R' is (C1-C8)alkyl); and x:y is 5:95 to 99.99 :0.01].
Specific examples of the epoxide compound according to the present invention may include ethylene oxide, propylene oxide, butene oxide, pentene oxide, hexene oxide, octene oxide, decene oxide, dodecene oxide, tetradecene oxide, hexadecene oxide, octadecene oxide, butadiene monoxide, 1,2-epoxide-7-octene, epifluorohydrine, epichlorohydrine, epibromohydrine, isopropyl glycidyl ether, butyl glycidyl ether, t-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, allyl glycidyl ether, cyclopentene oxide, cyclohexene oxide, cyclooctene oxide, cyclododecene oxide, alpha-pinene oxide, 2,3-epoxidenorbornene, limonene oxide, dieldrin, 2,3-epoxidepropylbenzene, styrene oxide, phenylpropylene oxide, stilbene oxide, chlorostilbene oxide, dichlorostilbene oxide, 1,2-epoxy-3-phenoxypropane, benzyloxymethyl oxirane, glycidyl-methylphenyl ether, chlorophenyl-2,3-epoxidepropyl ether, epoxypropyl methoxyphenyl ether, biphenyl glycidyl ether, glycidyl naphthyl ether, and the like.
An example of a method of producing the aliphatic polycarbonate may include a solution polymerization method or a bulk polymerization method. More specifically, polymerization may be performed by feeding carbon dioxide in the presence of the epoxide compound and a catalyst while using an organic solvent as a reactive medium.
As the organic solvent, aliphatic hydrocarbons such as pentane, octane, decane, cyclohexane, and the like; aromatic hydrocarbons such as benzene, toluene, xylene, and the like; and halogenated hydrocarbons such as chloromethane, methylenechloride, chloroform, carbontetrachloride, 1,1-dichloroethane, 1,2-dichloethane, ethylchloride, trichloroethane, 1-chloropropane, 2-chloropropane, 1-chlorobutane, 2-chlorobutane, 1-chloro-2-methylpropane, chlorobenzene, bromobenzene, and the like, may be used alone or in combination of two or more thereof. The pressure of carbon dioxide may be from normal pressure to 100 atm, and preferably, 5 atm to 30 atm. The polymerization temperature at the time of copolymerization may be 20~120℃, and preferably, 50~90℃. More preferably, the bulk polymerization method using a monomer itself as a solvent may be performed.
The aliphatic polycarbonate is polyalkylene carbonate produced based on descriptions of Korean Patent Laid-Open Publication Nos. 2008-0015454, 2009-0090154, 2010-067593, and 2010-0013255 filed by the present applicants, and examples of the alkylene may include, but are not limited to, ethylene, propylene, 1-butylene, cyclohexene, alkylglycidylether, n-butyl, n-octyl, and the like.
In the present invention, the aliphatic polycarbonate of Chemical Formula 1 above leads to a hot melt adhesive composition having a glass transition temperature (Tg) of 40 to 110℃.
The hot melt adhesive composition according to the present invention has a softening point of 70 to 130℃. Hence, the hot melt adhesive composition according to the present invention has an excellent adhesive strength or viscosity despite the low softening point thereof, and thus, is favorably applied at a low temperature.
In the present invention, the residual amount of a catalyst in the aliphatic polycarbonate used in the hot melt adhesive composition is 3 ppm or less. The residual amount of catalyst is minimized, such that the hot melt adhesive composition may be anticipated to have improved adhesive strength and thermal stability.
With the hot melt adhesive composition according to the present invention, the pyrolysis temperature is low, such that the harmful gas is not generated at the time of waste treatment, resulting in providing an excellent environmentally friendly product. In addition, the hot melt adhesive composition has the low melting temperature to thereby be usable at low temperature and exhibit sufficient adhesive strength. In addition, the hot melt adhesive composition is not easily pyrolyzed when being exposed to heat, due to the low residual amount of catalyst of 3 ppm or less.
Hereinafter, the present invention will be described in detail with reference to the examples, but is not limited to the following examples.
[Example 1]
Polypropylene carbonate having molecular weight of 290,000 g/mol as a base resin was extruded by using a 5m-length twin extruder at a rate of 1.6 kg/h at 230℃ to obtain polypropylene carbonate having a molecular weight of 50,000 g/mol. Next, the low-molecular weight polypropylene carbonate and 10 parts by weight of propylene carbonate as a plasticizer were mixed together, and the mixture was then extruded by using a twin extruder at 190℃, to be produced into a pellet. The viscosity of the thus produced hot melt adhesive was 10 Pa.sec. The hot melt adhesive was melted at 190℃, and then applied between a PVC sheet and wood in order to adhere them. The adhesive strength measurement result is shown in Table 1 below.
[Example 2]
10 parts by weight of propylene carbonate, and 5 parts by weight carnauba wax as a plasticizer were mixed to the polypropylene carbonate having a molecular weight of 50,000 g/mol, produced according to the same method as Example 1 above, and was extruded by using twin extruder at 190℃, to be produced into a pellet. The viscosity of the thus produced hot melt adhesive was 5Pa.sec at 180℃. The hot melt adhesive was melted at 190℃, and then applied between a PVC sheet and wood in order to adhere them. The adhesive strength measurement result is shown in Table 1 below.
[Comparative Example 1]
40g of rosin ester having a softening point of 90℃, 20g of a paraffin wax having a melting point of 60℃ were mixed to 40g of Ethylene vinylacetate having a vinyl acetate content of 20%, thereby producing a hot melt adhesive. The viscosity of the thus produced hot melt adhesive was 10 Pa.sec. The hot melt adhesive was melted at 190℃, and then applied between a PVC sheet and wood in order to adhere them. The adhesive strength measurement result is shown in Table 1 below.
Figure PCTKR2012006030-appb-I000002
As shown in FIG. 1 above, it may be appreciated that the hot melt adhesive compositions according to Examples 1 and 2 of the present invention had softening points of 100℃ and 110℃, respectively, and thus, the low melting temperatures thereof were low, such that they were usable at a low temperature and exhibited sufficient adhesive strength. The hot melt adhesive composition according to the present invention can have a softening point lower than that of Comparative Example 1 and unreduced adhesive strength, thereby providing an environmentally friendly hot melt adhesive.

Claims (8)

  1. A hot melt adhesive composition comprising aliphatic polycarbonate.
  2. The hot melt adhesive composition of claim 1, wherein the aliphatic polycarbonate is obtained by reacting carbon dioxide and at least one different epoxide compound.
  3. The hot melt adhesive composition of claim 2, wherein the epoxide compound is at least one selected from the group consisting of (C2-C10)alkylene oxide substituted or unsubstituted with halogen or alkoxy; (C4-C20)cycloalkyleneoxide substituted or unsubstituted with halogen or alkoxy; and (C8-C20)styreneoxide substituted or unsubstituted with halogen, alkoxy, alkyl, or aryl.
  4. The hot melt adhesive composition of claim 1 or 2, wherein the aliphatic polycarbonate is represented by Chemical Formula 1 below:
    [Chemical Formula 1]
    Figure PCTKR2012006030-appb-I000003
    [in Chemical Formula 1, m is an integer of 2 to 10; n is an integer of 1 to 3; R is hydrogen, (C1-C4)alkyl, or -CH2-O-R' (R' is (C1-C8)alkyl); and x:y is 5:95 to 99.99 :0.01.)].
  5. The hot melt adhesive composition of claim 2, wherein the aliphatic polycarbonate has a molecular weight of 50,000 g/mole, which is controlled by using a twin extruder at a rate of 1.0~2.0kg/h at 225~240℃, the twin extruder having an extruding path length of 4 to 6 M.
  6. The hot melt adhesive composition of claim 4, wherein the aliphatic polycarbonate has a glass transition temperature (Tg) of 40 to 110℃.
  7. The hot melt adhesive composition of any one of claims 1 to 6, wherein it has a softening point of 70 to 130℃.
  8. The hot melt adhesive composition of claim 7, wherein a residual amount of catalyst in the aliphatic polycarbonate is 3 ppm or less.
PCT/KR2012/006030 2011-08-18 2012-07-27 Hot melt composition WO2013024980A1 (en)

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Application Number Priority Date Filing Date Title
CN201280040327.0A CN103842464A (en) 2011-08-18 2012-07-27 Hot melt composition
JP2014525917A JP2014527565A (en) 2011-08-18 2012-07-27 Hot melt adhesive composition
EP12823800.3A EP2744867A4 (en) 2011-08-18 2012-07-27 Hot melt composition
US14/238,988 US20140206835A1 (en) 2011-08-18 2012-07-27 Hot Melt Composition

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KR10-2011-0081965 2011-08-18
KR1020110081965A KR101392705B1 (en) 2011-08-18 2011-08-18 Hot melt composition

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KR102309698B1 (en) 2020-01-16 2021-10-07 주식회사 이레A.T (에이티) Hot melt adhesive with excellent durability and adhesion

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2949718A4 (en) * 2013-09-10 2016-10-12 Lg Chemical Ltd Resin composition comprising polyalkylene carbonate and self-adhesive film produced therefrom
JP2016532756A (en) * 2013-09-10 2016-10-20 エルジー・ケム・リミテッド Resin composition containing polyalkylene carbonate and self-adhesive film produced therefrom
WO2017194445A1 (en) * 2016-05-09 2017-11-16 Repsol, S.A. Adhesive formulations with improved thermal and bonding properties
CN109072035A (en) * 2016-05-09 2018-12-21 雷普索尔公司 The adhesive formulation of heat and bond properties with improvement

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KR20130019781A (en) 2013-02-27
EP2744867A4 (en) 2015-03-25
JP2014527565A (en) 2014-10-16
KR101392705B1 (en) 2014-05-12
US20140206835A1 (en) 2014-07-24
EP2744867A1 (en) 2014-06-25
CN103842464A (en) 2014-06-04

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