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WO2003044087A2 - Adhesif autocollant a base d'un copolymere sequence de styrene hydrogene - Google Patents

Adhesif autocollant a base d'un copolymere sequence de styrene hydrogene Download PDF

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Publication number
WO2003044087A2
WO2003044087A2 PCT/US2002/037006 US0237006W WO03044087A2 WO 2003044087 A2 WO2003044087 A2 WO 2003044087A2 US 0237006 W US0237006 W US 0237006W WO 03044087 A2 WO03044087 A2 WO 03044087A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition
weight
block copolymer
amount
block
Prior art date
Application number
PCT/US2002/037006
Other languages
English (en)
Other versions
WO2003044087A3 (fr
Inventor
Thomas Carrig
Original Assignee
Adhesives Research, Inc.
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 Adhesives Research, Inc. filed Critical Adhesives Research, Inc.
Priority to AU2002365973A priority Critical patent/AU2002365973A1/en
Publication of WO2003044087A2 publication Critical patent/WO2003044087A2/fr
Publication of WO2003044087A3 publication Critical patent/WO2003044087A3/fr

Links

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
    • C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • 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
    • C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J153/02—Vinyl aromatic monomers and conjugated dienes
    • C09J153/025—Vinyl aromatic monomers and conjugated dienes modified
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials

Definitions

  • compositions optionally together with one or more of a tackifier or
  • plasticizer See, for example, U.S. Patent Nos. 5,093,422; 5,591,792; 5,703,162
  • compositions are primarily hot-melt type adhesive
  • compositions which are formulated to enable the composition to be used as a hot-
  • compositions as a hot-melt also serve to diminish the adhesive properties of the
  • compositions for example, significant amounts of plasticizers are generally present.
  • plasticizers are generally present.
  • hot-melt compositions present in hot-melt compositions in amounts (i.e., at least 10% by weight) which
  • hot-melt can be provided which need not be used in the form of a hot-melt.
  • hot-melt can be provided which need not be used in the form of a hot-melt.
  • melt application is considered to be two independent steps of compounding the
  • release liners or substrates in a second step. Each step utilizes different process
  • the present invention exhibits high peel adhesion values when
  • copolymers with substantially hydrogenated midblock is a focus on maintaining
  • the present invention is not driven by low melt viscosity and therefore
  • the present invention provides extremely high peel adhesion in conjunction with
  • substantially hydrogenated midblock The disclosed invention uses such polymers
  • block copolymer is employed to impart good adhesive properties while the
  • substantially hydrogenated block copolymer is used to provide enhanced holding
  • the present invention uses primarily or
  • coating weight plays a critical role in adhesion values obtained.
  • the adhesive of the present invention may be cured
  • Such activation generally comprises thermal or radiation activation (UN or electron beam activation). This is generally found to be a
  • the adhesive of the present invention desirably finds application in the
  • the present invention is directed to an adhesive composition comprising:
  • said A-B-A block copolymer being present in said composition in an amount
  • composition in an amount ranging from 40-85 % by weight, each being based on
  • said block copolymer comprising a graft
  • composition is in the form of an extrudate which may be used to adhere two
  • the block copolymer used in the adhesive of the present invention may be any material.
  • A-B-A block copolymers selected from a variety of A-B-A block copolymers.
  • the A-B-A block copolymer the A-B-A block copolymer
  • block is a non-elastomeric block comprised of homopolymers or copolymers of
  • vinyl monomers such as vinyl arenes, vinyl pyridines, vinyl halides and vinyl
  • carboxylates as well as acrylic monomers such as acrylonitrile, methacrylonitrile,
  • the A block may also comprise monovinyl aromatic
  • hydrocarbons including styrene, vinyl toluene, vinyl xylene, ethyl vinyl benzene as
  • dicyclic monovinyl compounds such as vinyl naphthalenes and the like.
  • non-elastomeric polymer A blocks may be derived from alpha olef ns,
  • alkylene oxides alkylene oxides, acetals, urethanes, etc.
  • styrene t-butyl styrene, 3-methyl styrene, 4-n-propylstyrene, 4-p-propylstyrene, 1-
  • the B block is an elastomeric block component which is preferably at least
  • Exemplary B blocks include but are not limited to polybutadiene, poly(ethylene-butylene),
  • polyisoprene poly(ethylene/propylene), etc.
  • the preferred block copolymer for use in the present invention is an
  • SEBS styrene-ethylene/butylene-styrene
  • the content of the A block in the block copolymer generally ranges from
  • copolymer generally ranges from about 55 to 90% by weight.
  • the block copolymer includes a graft moiety selected from the group
  • carboxylic acid and anhydrides thereof include but are not limited to mono-, di- or
  • polycarboxylic acids such as (meth)acrylic acid, maleic acid, fumaric acid, itaconic acid
  • anhydride such as dimethyl maleic anhydride or citrontonic anhydride, nadic
  • anhydride is particularly preferred as the graft moiety.
  • graft block copolymers are also commercially
  • the block copolymer is generally present in the adhesive composition of
  • the present invention in an amount of about 15 to 60 wt. %, based on the total
  • the block copolymer is present in an amount of greater than 20% by wt., and more preferably from 25-
  • tackifiers may be employed, with the tackifier being chosen for
  • the tackifier to be hydrogenated in the event that the block copolymer is
  • block copolymer that is, it is preferred for at least 50% , and most
  • exemplary tackifiers include but are not limited to natural
  • modified rosins such as gum rosin, wood rosin, tall oil rosin, distilled rosin,
  • pentaerythritol esters of natural and modified rosins such as glycerol ester of
  • hydrocarbon resins hydrocarbon resins
  • polyterpene resins based on alpha pinene, beta pinene or d-
  • limonene modified terpenes (such as styrene/terpene, alpha methyl
  • the tackifier which is employed exhibits a softening point within
  • the tackifier is generally present in the adhesive composition in an amount
  • the tackifier is ultimately present in an amount effective
  • tackifiers may also be employed as found desirable or advantageous.
  • tackifiers may also be employed as found desirable or advantageous.
  • the two different tackifiers may be of the same or different
  • the adhesive composition may contain additional components including but
  • plasticizers not limited to plasticizers, fillers, antioxidants, crosslinkers, wood or cellulose
  • thermoplastic polymers such as hydroxypropyl cellulose, polyamides, etc.
  • fillers such as thermal or electrical conductive fillers, clays, talc, solid spheres,
  • silica carbon, synthetic or natural fibers, dyes, pigments, etc.), stabilizers (thermal,
  • oxidative, UN, hydrolytic, etc. oxidative, etc.
  • exemplary stabilizers or antioxidants include those known to one of
  • phosphite antioxidants phosphite antioxidants
  • crosslinking agents include those known to one of ordinary skill
  • silane-type and isocyanate-type crosslinking agents for example, in a paper
  • Plasticizers which may be employed are those which are conventionally
  • plasticizers are employed in conjunction with polymeric compositions.
  • plasticizers are employed in conjunction with polymeric compositions.
  • plasticizers include but are not limited to oil and liquid elastomers which flow at
  • plasticizers are desirably low in aromatic content and are paraffinic
  • hydrocarbons and polyte ⁇ enes.
  • the plasticizer if present, will generally be present in an amount of up to
  • the adhesive composition of the present invention may also include
  • the block copolymer described above may also be combined with one or
  • copolymer For example, it may be an advantage to inco ⁇ orate a polystyrene
  • block copolymer (grafted or non-grafted) which block copolymer does not have an
  • diblocks being present in an amount of up to 30% by wt.
  • elastomeric midblock portion will comprise from about 25 to 100% by weight of
  • block copolymers is not critical, and may be modified in a manner sufficient to
  • the adhesive composition can be prepared as a solution
  • the preferred method of preparation is melt processing as 100% solids.
  • the components can be combined by continuous blending of the
  • a melt in a heated vessel such as a sigma blade mixer is also appropriate.
  • the components are melt mixed to a uniform adhesive composition, the discharged
  • release liner or backing substrate typically in the form of roll. Melt processing is
  • the adhesive composition can be any suitable adhesive composition.
  • preferably from 0.005-0.080" thickness) of the adhesive composition can be any suitable adhesive composition.
  • the adhesive composition provides novel utility as a strong adhesive that
  • Examples 1-9 and 12-15 illustrate the effect of the presence of
  • KRATON FG1924X (KRATON Polymers, LLC) is a maleic
  • anhydride SEBS copolymer having about 13 wt. % of styrene, about 30 wt. %
  • KRATON FG1901X is also a maleic anhydride grafted SEBS block copolymer
  • KRATON G1652 is a SEBS block copolymer with no maleic
  • Resin H Resinas
  • Sinteticas is a hydrogenated rosin with a softening point of about 70 °C and a
  • Foral 105 (Hercules, Inc.) is a pentaerithrytol ester
  • Sylvares TR-1085 (Arizona Chemical) is a polyte ⁇ ene resin based on ⁇ -pinene with a softening point of about 85°C and an acid number of less
  • Sylavrez TR-1100 (Arizona Chemical) is a polyte ⁇ ene resin based on ⁇ -
  • pinene with a softening point of about 100°C and an acid number of less than 1.
  • Escorez 5380 (Exxon Mobil) is a hydrogenated hydrocarbon resin with a softening
  • Tire & Rubber is an aliphatic C 5 petroleum hydrocarbon that is liquid at room
  • Indopol H-1900 is a polybutene (BP Amoco).
  • Hercolyn D (Pinova)
  • Cellolyn 21 (Pinova division of Hercules, Inc.) is a phthalate ester of
  • Escorez 1580 (ExxonMobil Chemical) is an aliphatic
  • hydrocarbon resin with a softening point of about 80 °C.
  • homogeneous mixture was coated onto a desired substrate or backing material.
  • the preferred substrate is a release material in roll form.
  • the Examples 1-15 were
  • SAFT Shear Adhesion Failure Temperature

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne une composition adhésive comprenant (a) un copolymère séquencé A-B-A ayant une séquence A non élastomère, formée d'homopolymères et de copolymères de monomères vinyliques, et une séquence B qui est élastomère et sensiblement hydrogénée ; (b) une résine adhésive, et (c) le cas échéant, un plastifiant, à raison de 20 % en poids ou moins, le copolymère séquencé A-B-A étant présent dans la composition à raison de 15-60 % en poids, et la résine adhésive étant présente dans la composition à raison de 40-85 % en poids, chacun de ces pourcentages se référant au poids total de la composition, le copolymère séquencé comprenant une fraction greffée, en une quantité de l'ordre de 0,5 à 5,0 % en poids, ladite fraction greffée étant sélectionnée dans le groupe comprenant des acides carboxyliques éthyléniquement insaturés, des anhydrides d'acides carboxyliques éthyléniquement insaturés et des dérivés de ces produits.
PCT/US2002/037006 2001-11-19 2002-11-19 Adhesif autocollant a base d'un copolymere sequence de styrene hydrogene WO2003044087A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002365973A AU2002365973A1 (en) 2001-11-19 2002-11-19 Pressure sensitive adhesive based on hydrogenated styrene block copolymer

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US33154001P 2001-11-19 2001-11-19
US60/331,540 2001-11-19
US39810602P 2002-07-25 2002-07-25
US60/398,106 2002-07-25

Publications (2)

Publication Number Publication Date
WO2003044087A2 true WO2003044087A2 (fr) 2003-05-30
WO2003044087A3 WO2003044087A3 (fr) 2007-11-01

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2002/037006 WO2003044087A2 (fr) 2001-11-19 2002-11-19 Adhesif autocollant a base d'un copolymere sequence de styrene hydrogene

Country Status (2)

Country Link
AU (1) AU2002365973A1 (fr)
WO (1) WO2003044087A2 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1548079A1 (fr) * 2003-12-22 2005-06-29 tesa AG Rubans adhésifs réticulables chimiquement
EP1548078A1 (fr) * 2003-12-22 2005-06-29 tesa AG Rubans adhésifs réticulables chimiquement
US9902884B2 (en) 2014-12-17 2018-02-27 H.B. Fuller Company Hot melt adhesive composition for bonding packs of plastic containers
EP3204437A4 (fr) * 2014-10-09 2018-05-30 Kraton Polymers U.S. LLC Compositions adhésives avec des polyoléfines amorphes
US10351298B2 (en) 2014-12-17 2019-07-16 H.B. Fuller Company Hot melt adhesive composition for bonding packs of metal containers

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6214476B1 (en) * 1997-02-10 2001-04-10 Mitsubishi Chemical Corporation Adhesive resin compositions, laminates, production method thereof and oriented films

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6214476B1 (en) * 1997-02-10 2001-04-10 Mitsubishi Chemical Corporation Adhesive resin compositions, laminates, production method thereof and oriented films

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1548079A1 (fr) * 2003-12-22 2005-06-29 tesa AG Rubans adhésifs réticulables chimiquement
EP1548078A1 (fr) * 2003-12-22 2005-06-29 tesa AG Rubans adhésifs réticulables chimiquement
EP3204437A4 (fr) * 2014-10-09 2018-05-30 Kraton Polymers U.S. LLC Compositions adhésives avec des polyoléfines amorphes
US9902884B2 (en) 2014-12-17 2018-02-27 H.B. Fuller Company Hot melt adhesive composition for bonding packs of plastic containers
US10351298B2 (en) 2014-12-17 2019-07-16 H.B. Fuller Company Hot melt adhesive composition for bonding packs of metal containers

Also Published As

Publication number Publication date
AU2002365973A8 (en) 2003-06-10
AU2002365973A1 (en) 2003-06-10
WO2003044087A3 (fr) 2007-11-01

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