WO2008032964A1 - Composition d'adhésif à solvant pour polyester - Google Patents

Composition d'adhésif à solvant pour polyester Download PDF

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Publication number
WO2008032964A1
WO2008032964A1 PCT/KR2007/004366 KR2007004366W WO2008032964A1 WO 2008032964 A1 WO2008032964 A1 WO 2008032964A1 KR 2007004366 W KR2007004366 W KR 2007004366W WO 2008032964 A1 WO2008032964 A1 WO 2008032964A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyester
test pieces
adhesive composition
bonded
solvent
Prior art date
Application number
PCT/KR2007/004366
Other languages
English (en)
Inventor
Jeoung Jun Hwang
Dong Jun Hwang
Sang Mook Kim
Original Assignee
Sk Chemicals 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 Chemicals Co., Ltd. filed Critical Sk Chemicals Co., Ltd.
Publication of WO2008032964A1 publication Critical patent/WO2008032964A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
    • C08J5/122—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using low molecular chemically inert solvents, swelling or softening agents
    • 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
    • C09J127/00—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 a halogen; Adhesives based on derivatives of such polymers
    • C09J127/02—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 a halogen; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
    • C09J127/12—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 a halogen; Adhesives based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers

Definitions

  • the present invention relates to a solvent adhesive composition for polyester, and, more particularly, to a solvent adhesive composition for polyester which can exhibit adhesivity equal to or greater than the adhesivity exhibited when conventional acrylate or polycarbonate is bonded using methylene chloride.
  • polyester Since polyester has excellent mechanical strength, heat resistance, transparency and gas barrier properties, it is suitable for use as a material for a container for beverages, such as juice, soft drinks, carbonated drinks, and the like, a packing film, a film for audio, a film for video, or the like, and thus polyester is used in large quantities. Further, polyester is also used as an industrial material, such as medical fibers, tire cords, and the like in large quantities on a worldwide scale.
  • polyester has high chemical resistance
  • methylene chloride and chloroform as an adhesive
  • the methylene chloride and chloroform do not exhibit good adhesivity, and the bonded portion of the polyester product is easily damaged.
  • an epoxy adhesive and an acrylate adhesive which are commercially available as adhesives
  • the bonded portion of the polyester product is also easily damaged. The reason that these adhesives do not exhibit good adhesivity and the bonded portion of the polyester product is easily damaged is determined to be because the solubility and compatibility of these adhesives to polyester are not good.
  • a solvent adhesive is used for bonding the molded polyester product, if the molded polyester product requires the same kind of adhesive or a different kind of adhesive having compatibility similar thereto.
  • a solvent adhesive are known as follows.
  • Japanese Unexamined Patent Publication No.1999-311421 discloses an adhesive for polyethylene terephthalate (hereinafter, referred to as "PET") > in which a PET-soluble solvent, for example, methyl ethyl ketone, is mixed with alcohols (methanol or ethanol).
  • acetone, methyl ethyl ketone, cyclohexane, diphenyl ether, ethyl acetate, n-propyl acetate, n- butyl acetate, methyl lactate, tetrahydrofuran, benzene, xylene, n-hexane, or 1,2-dichloroethane may also be used as an adhesive solvent, but that these adhesive solvents are somewhat poor in the aspects of blanching and adhesive strength.
  • Japanese Unexamined Patent Publication No. 2000-008017 discloses an adhesive for a PET resin, in which, as an adhesive for bonding a resin formed of an amorphous polyester copolymer including PET as a basic structure, methyl ethyl ketone is used as a main solvent, and the main solvent is mixed with a ketone subsidiary solvent having a relatively high boiling point.
  • a ketone subsidiary solvent may include acetone, methyl iso-butyl ketone, and cyclohexanone.
  • Japanese Unexamined Patent Publication No. 2000-144081 discloses an adhesive for polyester including a straight-chain alcohol bonded with 4 or more fluorine atoms as a main component. Further, it was disclosed in this Patent Publication that this adhesive for polyester may be used by diluting it with a commonly-used solvent. Examples of the straight-chain alcohol bonded with 4 or more fluorine atoms may include tetrafluoropropanol, octafluoropentanol, and dodecafluoroheptanol.
  • the adhesives mentioned in the above patent documents are modified to improve the adhesive strength thereof and prevent blanching, but are problematic in that they are also required to be further modified in the peel resistance of the bonded portion. This means that, when the adhesive is adhered to a molded product and the molded product is carried, the molded product is in danger of being easily broken even by a small impact.
  • an object of the present invention is to provide a solvent adhesive composition for polyester which is not yet commercially available.
  • the present invention provides a solvent adhesive composition for polyester, including 2 ⁇ 98% by weight of tetrachloroethane, orthochlorophenol, or a mixture thereof; and 98 ⁇ 2% by weight of hexafluoroisopropanol, trifluoroacetic acid, or a mixture thereof.
  • polyester products cannot be bonded using adhesives for acrylate or polycarbonate.
  • the solvent adhesive composition according to the present invention when used for bonding the polyester products, it can realize adhesivity equal to or greater than that exhibited by bonding acrylate products or polycarbonate products using the adhesives for acrylate or polycarbonate.
  • the present invention provides a solvent adhesive composition for polyester which has excellent adhesivity, equal to that realized by mixing methylene chloride with polycarbonate and acrylate, and is economical.
  • polar or nonpolar solvents which can easily dissolve polyester were selected, and then the volatility and solubility of each of the solvents was comprehensively evaluated, thereby adopting four solvents.
  • the four adopted solvents include hexafluoroisopropanol (hereinafter, referred to as "HFIP”), trifluoroacetic acid (hereinafter, referred to as "TFA”), tetrachloroethane (hereinafter, referred to as "TCE”), and orthochlorophenol (hereinafter, referred to as "OCP”).
  • the HFIP and TFA are expensive and have excellent solubility and adhesivity for a short period of time of 10 ⁇ 20 seconds, they are disadvantageous in that they have high volatility, so that the time for which they contact the adherend is decreased, thereby increasing the usage thereof.
  • the usage of the TCE and OCP can be decreased because they are cheap and have relatively low volatility, and thus the time for which they contact the adherend is increased, they are disadvantageous in that they cannot exhibit good adhesivity in a short period of time of 10 ⁇ 20 seconds.
  • the present inventors discovered a unique solvent adhesive composition for polyester, which can make up for the advantages and disadvantages between two solvent groups and can dissolve polyester resin, which is the raw material of the adherend.
  • the unique solvent adhesive composition including polyester resin is provided for the purpose of compensating for the defects and increasing the contact area, thereby improving adhesivity.
  • the unique solvent adhesive composition for polyester includes 2 ⁇ 98% by weight of TCE, OCP, or a mixture thereof, and 98 ⁇ 2% by0 weight of HFIP, TFA, or a mixture thereof.
  • the unique solvent adhesive composition for polyester includes 80 ⁇ 95% by weight of TCE, OCP, or a mixture thereof, and 5 ⁇ 20% by weight of HFIP, TFA, or a mixture thereof.
  • TCE or OCP is below 2% by weight and the amount of HFIP or TFA is above 98% by weight, the adhesivity of the solvent adhesive composition in a short period of time is not further5 improved compared to the usage of HFIP or TFA, and thus it is not preferable.
  • the amount of HFIP or TFA is above 98% by weight
  • the mixing ratio of the mixture of TCE and OCP or the mixing ration of the mixture of HFP and TFA may be in any range.
  • Comparative Example 1 5 Two acrylate test pieces having a width of 2.5 cm, a length of 7.5 cm and a thickness of 2 mm were provided, and then the two acrylate test pieces were bonded to each other using methylene chloride so that they overlapped each other by 5mm each. Subsequently, the bonded acrylate test pieces were left at room temperature for 1 hour and for 1 day, after which the testing of the bonded acrylate test pieces in tension was conducted. Here, the tension of the acrylate test pieces was measured in groups of three, and the failure strength thereof was determined by comparing average values. Comparative Example 2
  • BR which is a polyester resin manufactured by SK Chemicals Co., Ltd., having a width of 2.5 cm, a length of 7.5 cm and a thickness of 2 mm, were provided, and then the two BR test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using methylene chloride so that they overlapped each other by 5mm each. Subsequently, the bonded BR test pieces were left at room temperature for 1 hour and for 1 day, after which the testing of the bonded BR test pieces under tension was conducted. Here, the tension of the polycarbonate test pieces was measured in groups of three, and the failure strength thereof was determined by comparing average values.
  • Example 1 is a polyester resin manufactured by SK Chemicals Co., Ltd.
  • HFIP and TCE in which the weight ratio of HFP to TCE was 2 : 98, so that they overlapped each other by 5mm each.
  • the bonded BR test pieces were left at room temperature for 1 hour and for 1 day, after which the testing of the bonded BR test pieces in tension was conducted.
  • the tension of the polycarbonate test pieces was measured in groups of three, and the failure strength thereof was determined by comparing average values.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including HFIP and TCE, in which the weight ratio of HFIP to TCE was 5 : 95, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including HFIP and TCE, in which the weight ratio of HFIP to TCE was 10 : 90, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including HFP and TCE, in which the weight ratio of HFP to TCE was 20 : 80, and the failure strength thereof was measured using the same method as in Example 1.
  • Example 5 An adhesive composition including HFP and TCE, in which the weight ratio of HFP to TCE was 20 : 80, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including HFP and TCE, in which the weight ratio of HFEP to TCE was 30 : 70, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including HFP and OCP, in which the weight ratio of HFP to OCP was 2 : 98, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including HFP and OCP, in which the weight ratio of HFP to OCP was 5 : 95, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including HFP and OCP, in which the weight ratio of HFP to OCP was 10 : 90, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including TFA and TCE, in which the weight ratio of TFA to TCE was 2 : 98, and the failure strength thereof was measured using the same method as in Example 1.
  • Example 10
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including TFA and TCE, in which the weight ratio of TFA to TCE was 5 : 95, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including TFA and TCE, in which the weight ratio of TFA to TCE was 10 : 90, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including TFA and OCP, in which the weight ratio of TFA to OCP was 2 : 98, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including TFA and OCP, in which the weight ratio of TFA to OCP was 5 : 95, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including TFA and OCP, in which the weight ratio of TFA to OCP was 10 : 90, and the failure strength thereof was measured using the same method as in Example 1.
  • Example 15
  • Test pieces the same as in Example 1 were provided, and then the surfaces of the test pieces were roughened using sandpaper, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including TFA and TCE, in which the weight ratio of TFA to TCE was 20 : 80, and which did not dissolve BR, and the failure strength thereof was measured using the same method as in Example 1.
  • Test pieces the same as in Example 1 were provided, the test pieces were bonded to each other such that the distance therebetween was in the range of 0.03 ⁇ 0.04 mm using an adhesive composition including HFIP, TFA and OCP, in which the weight ratio of HFIP, TFA and OCP was 2 : 3 : 95, and the failure strength thereof was measured using the same method as in Example 1.
  • the adhesivity of the solvent adhesive composition for polyester according to the present invention is equal to or greater than the adhesivity exhibited when acrylate, polycarbonate, or BR is bonded using methylene chloride.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne une composition d'adhésif à solvant pour polyester qui permet de coller un polymère de polyester, qui présente une haute résistance chimique par comparaison avec d'autres polymères amorphes utilisés couramment, tels que le polycarbonate, l'acrylate et similaire, et ne permet donc pas d'obtenir une bonne adhésivité et une bonne aptitude à la mise en oeuvre au moyen des adhésifs à solvant courants utilisés pour le polycarbonate ou l'acrylate. La composition d'adhésif à solvant selon l'invention présente ainsi une meilleure adhésivité et une meilleure aptitude à la mise en oeuvre que les adhésifs classiques.
PCT/KR2007/004366 2006-09-11 2007-09-10 Composition d'adhésif à solvant pour polyester WO2008032964A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2006-0087469 2006-09-11
KR1020060087469A KR101249556B1 (ko) 2006-09-11 2006-09-11 폴리에스테르용 솔벤트 접착 조성물

Publications (1)

Publication Number Publication Date
WO2008032964A1 true WO2008032964A1 (fr) 2008-03-20

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Application Number Title Priority Date Filing Date
PCT/KR2007/004366 WO2008032964A1 (fr) 2006-09-11 2007-09-10 Composition d'adhésif à solvant pour polyester

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KR (1) KR101249556B1 (fr)
WO (1) WO2008032964A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR970002309B1 (ko) * 1993-10-20 1997-02-27 주식회사 에스 · 케이 · 씨 폴리에스테르 필름
EP0974438A1 (fr) * 1998-01-27 2000-01-26 Teijin Limited Preforme en polyester aromatique, moulages par soufflage et procede de production de ladite preforme
WO2006009285A1 (fr) * 2004-07-22 2006-01-26 Teijin Limited Acide polylactique et son processus de production
WO2006016683A1 (fr) * 2004-08-11 2006-02-16 Toyo Seikan Kaisha, Ltd. Résine de polyester pour moulage sous pression, processus de fabrication d'ébauches et ébauches

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56125472A (en) 1980-03-10 1981-10-01 Ricoh Elemex Corp Adhesive for polyester
JPH04300924A (ja) * 1991-03-29 1992-10-23 Sekisui Chem Co Ltd ポリエステルフィルムもしくはシートの接着方法
JP3281000B2 (ja) * 1991-07-31 2002-05-13 三菱樹脂株式会社 ポリエステルシートを用いたケースの成形方法
JP2000144081A (ja) 1998-11-13 2000-05-26 Kosuke Iida ポリエステル用接着剤

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR970002309B1 (ko) * 1993-10-20 1997-02-27 주식회사 에스 · 케이 · 씨 폴리에스테르 필름
EP0974438A1 (fr) * 1998-01-27 2000-01-26 Teijin Limited Preforme en polyester aromatique, moulages par soufflage et procede de production de ladite preforme
WO2006009285A1 (fr) * 2004-07-22 2006-01-26 Teijin Limited Acide polylactique et son processus de production
WO2006016683A1 (fr) * 2004-08-11 2006-02-16 Toyo Seikan Kaisha, Ltd. Résine de polyester pour moulage sous pression, processus de fabrication d'ébauches et ébauches

Also Published As

Publication number Publication date
KR101249556B1 (ko) 2013-04-01
KR20080023501A (ko) 2008-03-14

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