WO1992021718A1 - Water dispersible pressure sensitive hot melts - Google Patents

Water dispersible pressure sensitive hot melts Download PDF

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Publication number
WO1992021718A1
WO1992021718A1 PCT/US1992/003521 US9203521W WO9221718A1 WO 1992021718 A1 WO1992021718 A1 WO 1992021718A1 US 9203521 W US9203521 W US 9203521W WO 9221718 A1 WO9221718 A1 WO 9221718A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
composition according
pressure sensitive
copolymer
fatty acid
Prior art date
Application number
PCT/US1992/003521
Other languages
French (fr)
Inventor
Gary S. Russell
Original Assignee
Isp Investments 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 Isp Investments Inc. filed Critical Isp Investments Inc.
Priority to AU19090/92A priority Critical patent/AU656980B2/en
Priority to JP4511454A priority patent/JPH06508165A/en
Priority to EP92911262A priority patent/EP0586478B1/en
Priority to DE69208658T priority patent/DE69208658T2/en
Publication of WO1992021718A1 publication Critical patent/WO1992021718A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
    • 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
    • C09J139/00—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Adhesives based on derivatives of such polymers
    • C09J139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C09J139/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
    • 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
    • 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
    • C08L2666/24—Graft or block copolymers according to groups C08L51/00, C08L53/00 or C08L55/02; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of 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
    • 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
    • C09J2301/304—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 heat-activatable, i.e. not tacky at temperatures inferior to 30°C

Definitions

  • This invention relates to a composition useful as a pressure sensitive hot melt adhesive.
  • the invention also relates to labels and adhesive tapes making use of this adhesive.
  • the composition is also useful as a deformable mass for certain medical applications.
  • Pressure sensitive hot melt adhesives are widely used. Most of such adhesives make use of thermoplastic rubbers which may be isoprene/styrene block copolymers or butadiene/styrene block copolymers. These rubbers are very hydrophobic. A drawback of such adhesives is that residues of such compositions become a very undesirable hydrophobic contaminant in water-based processes for recycling paper or fibreboard which has been treated with the adhesive. For instance if paper or board is treated with a hydrophobic pressure se/sitive adhesive and used to make labels, the residue of the adhesive is a considerable obstacle to recycling any scrap material. 2 Pressure sensitive adhesives which are water dispersible are known. US patent 4331576, Colon et al 1981, discloses hot melt pressure sensitive adhesives which contain vinyl pyrrolidone/vinyl acetate copolymers,
  • thermoplastic composition comprising
  • the balance of the composition can be provided by optional ingredients.
  • the thermoplastic rubber will generally be a copolymer of a monomer with one olefinic unsaturation and a monomer with two olefinic bonds especially a styrene/isoprene block copolymer or a styrene/butadiene block copolymer.
  • An example of the former is the thermoplastic rubbers available from Shell under their registered trade mark Cariflex TR.
  • the amount of thermoplastic rubber is preferably from 4 to 20% by weight of the composition, and for higher peel strengths may be at least 6 wt%.
  • a suitable vinyl pyrrolidone/vinyl acetate copolymer is PVP/VA S-630 available from GAF Corporation.
  • This polymer contains vinyl pyrrolidone and vinyl acetate in approximate weight ratio of 6:4. These two monomers are randomly distributed in the polymer.
  • the amount of this copolymer ranges from 10 to 50 wt% of the composition, preferably 15 to 40 wt%.
  • the third essential main component is fatty acid in an amount from 10 to 50 wt%.
  • fatty acids are generally mixtures with a range of carbon chain lengths present.
  • the fatty acid which is used may have a preponderance of shorter chains, from 10 to 14 carbon atoms, or of larger chains from 16 to 20 carbon atoms. The latter may include unsaturated chains but need not do so.
  • Shorter chain fatty acid may be coconut derived.
  • a suitable larger chain fatty acid is isostearic acid.
  • An ingredient which will usually be included is a tackifying resin in a quantity from 10 to 50 wt%, better 20 to 40 wt% of the composition.
  • Materials which can serve as tackifying resins include wood rosins, tall oils, esters of such rosins, and tall oils, and polyterpenes. Specific examples which are commercially available include Foral 85E from Hercules BV which is hydrogenated rosin, Staybelite Resin E from Hercules BV which is partially hydrogenated rosin, Piccolyte polyterpene resins from Hercules BV and Imprez aliphatic hydrocarbon resin available from ICI.
  • compositions according to the invention will generally include antioxidant in an amount from which is a fraction of a percent.
  • the compositions will often also include from 2 to 10 wt% of an ester plasticiser, such as dialkyl phthalates or alkyl benzoates.
  • an ester plasticiser such as dialkyl phthalates or alkyl benzoates.
  • Compositions according to this invention can be prepared simply by mixing the ingredient materials with heating and stirring to form a melt of them all. It may be found convenient to mix tackifying resin and the thermoplastic rubber together in a high shear mixer before mixing with the other ingredients. The mixing operation may be carried out under a blanket of inert gas such as nitrogen. This is conventional practice for making other hot melt compositions.
  • compositions will generally include tackifying resin. They may be applied to a paper substrate by conventional methods for application of hot melt adhesive.
  • the compositions may be used in particular for the production of pressure sensitive labels and pressure sensitive adhesive tapes.
  • Each of these products consists of a substrate which may be paper, fibreboard or a plastic film, coated with the adhesive composition embodying the present invention.
  • compositions of the present invention are as a thermoplastic material which may be used in various medical applications.
  • a quantity of composition according to the invention can be made large enough to sustain its own shape when at body heat or below and can be adhered to the human skin. This could be done to adhere a probe or sensor to the skin.
  • the composition could be impregnated with a drug for topical application which will progressively migrate from the composition into the skin to which the composition is adhering.
  • compositions were prepared using various proportions of the following commercially available ingredients:-
  • Cariflex P1107 which is styrene/isoprene block copolymer available from Shell
  • Foral 85 which is hydrogenated refined wood rosin, a tackifying resin available from Hercules B.V.
  • Prifac 7901 which is a fatty acid derived principally from coconut oil and available from Unichema International. This fatty acid contains about 48% of lauric acid (12 carbon atoms) and 18% of myristic acid (14 carbon atoms). The remainder of the fatty acid is provided by acids of other chain lengths.
  • Dioctyl phthalate plasticizer Dioctyl phthalate plasticizer.
  • Imganox 1010 or Topanol CA which are sterically hindered phenol antioxidents available from Ciba-Geigy and ICI respectively.
  • the four compositions contain these materials in the amounts set out in Table 1 below.
  • the Table also includes a comparative composition containing polyethylene glycol of average molecular weight 400 (PEG 400) and an ethylene/acrylic acid copolymer.
  • Samples of each adhesive composition were coated onto a polyester tape substrate such as Melinex (ICI) using a wire wound draw bar to spread the pre-heated melt onto the polyester film at a thickness of 25 ⁇ and then laminating with silicone release paper.
  • ICI Melinex
  • the adhesive tape is pressed onto stainless steel using a roller of standard weight. It is then peeled off at an angle of 180° utilizing automated machinery to draw the tape off at a rate of 300 mm/minute and measure the applied force required. The results are expressed as grammes force per 25mm of tape width.
  • Shear adhesion was measured by pressing tape onto a glass plate using the standard roller so that the tape was adhered to an area of specified dimensions at the edge of the plate. A standard weight was then attached to a
  • tack a length of the tape was formed into a loop with the sticky side outwards.
  • the loop is lowered onto a stainless steel surface until a prescribed length at the base of the loop is lying flat on the surface. No other pressure is applied to this adhesive film.
  • the loop of tape is then drawn away from the stainless steel surface using automated machinery to draw the tape off at a rate of 300 mm/minute while measuring the applied force required.
  • ashability was assessed by coating a paper label with the adhesive composition, adhering that paper label to a glass surface and, later, removing the label by washing with water under standardised conditions. An assessment was made of the ease with which both the paper label and the adhesive were removed from the glass surface during washing.
  • compositions 1 and 4 in Table 1 that even a small percentage of the thermoplastic rubber gives a considerable enhancement of peel strength without destroying .washability. Moreover composition 1 has greater peel strength than the somewhat different composition 5 which includes ethylene/acrylic acid copolymer.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Manufacturing Of Micro-Capsules (AREA)

Abstract

A pressure sensitive hot melt adhesive contains thermoplastic rubber such as styrene isoprene copolymer, a copolymer of vinylpyrrolidone and vinylacetate, fatty acid and, usually, tackifying resin. The composition is water soluble or water dispersible which facilitates removal of labels by washing and recycling of scrap material in label production. The composition gives better properties, especially peel strength, than other water-soluble or dispersible hot melt compositions.

Description

WATER DISPERSIBLE PRESSURE SENSITIVE HOT MELTS
Field of the Invention
This invention relates to a composition useful as a pressure sensitive hot melt adhesive. The invention also relates to labels and adhesive tapes making use of this adhesive. The composition is also useful as a deformable mass for certain medical applications.
Background of the Invention and Summary of the Prior Art
Pressure sensitive hot melt adhesives are widely used. Most of such adhesives make use of thermoplastic rubbers which may be isoprene/styrene block copolymers or butadiene/styrene block copolymers. These rubbers are very hydrophobic. A drawback of such adhesives is that residues of such compositions become a very undesirable hydrophobic contaminant in water-based processes for recycling paper or fibreboard which has been treated with the adhesive. For instance if paper or board is treated with a hydrophobic pressure se/sitive adhesive and used to make labels, the residue of the adhesive is a considerable obstacle to recycling any scrap material. 2 Pressure sensitive adhesives which are water dispersible are known. US patent 4331576, Colon et al 1981, discloses hot melt pressure sensitive adhesives which contain vinyl pyrrolidone/vinyl acetate copolymers,
5 ethylene/vinyl acetate copolymers, certain fatty acids, and rosin or tall oils. This patent explains that because of the water dispersability a label which is adhered with the adhesive can be removed on wetting the label.
Unexpectedly we have now found that it is 0 possible to prepare water-soluble or water-dispersible hot melt pressure sensitive adhesives using the more conventional thermoplastic rubbers and the resulting compositions can give better tack, peel strength and cohesive strength than provided by the previously disclosed water-soluble or dispersible hot melt compositions.
According to the present invention there is provided a hot melt composition comprising
3 to 50wt% of a thermoplastic rubber 10 to 50 wt% of a copolymer of vinyl pyrollidone and vinyl acetate
10 to 50 wt% of monocarboxylic fatty acid having 8 to 22 carbon atoms.
/
The balance of the composition can be provided by optional ingredients. The thermoplastic rubber will generally be a copolymer of a monomer with one olefinic unsaturation and a monomer with two olefinic bonds especially a styrene/isoprene block copolymer or a styrene/butadiene block copolymer. An example of the former is the thermoplastic rubbers available from Shell under their registered trade mark Cariflex TR.
The amount of thermoplastic rubber is preferably from 4 to 20% by weight of the composition, and for higher peel strengths may be at least 6 wt%.
A suitable vinyl pyrrolidone/vinyl acetate copolymer is PVP/VA S-630 available from GAF Corporation.
This polymer contains vinyl pyrrolidone and vinyl acetate in approximate weight ratio of 6:4. These two monomers are randomly distributed in the polymer.
The amount of this copolymer ranges from 10 to 50 wt% of the composition, preferably 15 to 40 wt%.
The third essential main component is fatty acid in an amount from 10 to 50 wt%. i Commercially available fatty acids are generally mixtures with a range of carbon chain lengths present. The fatty acid which is used may have a preponderance of shorter chains, from 10 to 14 carbon atoms, or of larger chains from 16 to 20 carbon atoms. The latter may include unsaturated chains but need not do so. Shorter chain fatty acid may be coconut derived. A suitable larger chain fatty acid is isostearic acid.
An ingredient which will usually be included is a tackifying resin in a quantity from 10 to 50 wt%, better 20 to 40 wt% of the composition.
Materials which can serve as tackifying resins include wood rosins, tall oils, esters of such rosins, and tall oils, and polyterpenes. Specific examples which are commercially available include Foral 85E from Hercules BV which is hydrogenated rosin, Staybelite Resin E from Hercules BV which is partially hydrogenated rosin, Piccolyte polyterpene resins from Hercules BV and Imprez aliphatic hydrocarbon resin available from ICI.
Compositions according to the invention will generally include antioxidant in an amount from which is a fraction of a percent. The compositions will often also include from 2 to 10 wt% of an ester plasticiser, such as dialkyl phthalates or alkyl benzoates. / Compositions according to this invention can be prepared simply by mixing the ingredient materials with heating and stirring to form a melt of them all. It may be found convenient to mix tackifying resin and the thermoplastic rubber together in a high shear mixer before mixing with the other ingredients. The mixing operation may be carried out under a blanket of inert gas such as nitrogen. This is conventional practice for making other hot melt compositions.
The principal application envisaged for the invention is use as a hot melt pressure sensitive adhesive. For this application the compositions will generally include tackifying resin. They may be applied to a paper substrate by conventional methods for application of hot melt adhesive. The compositions may be used in particular for the production of pressure sensitive labels and pressure sensitive adhesive tapes. Each of these products consists of a substrate which may be paper, fibreboard or a plastic film, coated with the adhesive composition embodying the present invention.
Another application for the compositions of the present invention is as a thermoplastic material which may be used in various medical applications. A quantity of composition according to the invention can be made large enough to sustain its own shape when at body heat or below and can be adhered to the human skin. This could be done to adhere a probe or sensor to the skin. Alternatively the composition could be impregnated with a drug for topical application which will progressively migrate from the composition into the skin to which the composition is adhering.
Embodiments of the invention will now be described by way of example:
A series of compositions were prepared using various proportions of the following commercially available ingredients:-
Cariflex P1107 which is styrene/isoprene block copolymer available from Shell
Foral 85 which is hydrogenated refined wood rosin, a tackifying resin available from Hercules B.V.
Prifac 7901 which is a fatty acid derived principally from coconut oil and available from Unichema International. This fatty acid contains about 48% of lauric acid (12 carbon atoms) and 18% of myristic acid (14 carbon atoms). The remainder of the fatty acid is provided by acids of other chain lengths.
Dioctyl phthalate plasticizer. Imganox 1010 or Topanol CA, which are sterically hindered phenol antioxidents available from Ciba-Geigy and ICI respectively. The four compositions contain these materials in the amounts set out in Table 1 below. The Table also includes a comparative composition containing polyethylene glycol of average molecular weight 400 (PEG 400) and an ethylene/acrylic acid copolymer.
Samples of each adhesive composition were coated onto a polyester tape substrate such as Melinex (ICI) using a wire wound draw bar to spread the pre-heated melt onto the polyester film at a thickness of 25μ and then laminating with silicone release paper.
Properties of the resulting films were then tested using standard tests prescribed by the Pressure Sensitive Tape Council.
In the test for peel strength the adhesive tape is pressed onto stainless steel using a roller of standard weight. It is then peeled off at an angle of 180° utilizing automated machinery to draw the tape off at a rate of 300 mm/minute and measure the applied force required. The results are expressed as grammes force per 25mm of tape width.
Shear adhesion was measured by pressing tape onto a glass plate using the standard roller so that the tape was adhered to an area of specified dimensions at the edge of the plate. A standard weight was then attached to a
Figure imgf000010_0001
8 length of the tape projecting from the edge of the glass plate which was clamped at an angle of 2° to the vertical. The' ime elapsed before the tape falls off from the plate was measured.
To assess tack a length of the tape was formed into a loop with the sticky side outwards. The loop is lowered onto a stainless steel surface until a prescribed length at the base of the loop is lying flat on the surface. No other pressure is applied to this adhesive film. The loop of tape is then drawn away from the stainless steel surface using automated machinery to draw the tape off at a rate of 300 mm/minute while measuring the applied force required.
ashability was assessed by coating a paper label with the adhesive composition, adhering that paper label to a glass surface and, later, removing the label by washing with water under standardised conditions. An assessment was made of the ease with which both the paper label and the adhesive were removed from the glass surface during washing.
Results for these tests are given in Table 1 which follows. Table 1
Figure imgf000011_0001
Ethylene/acrylic acid copolymer 20.0
Peel Strength (g/25mm) 1500 2000 3000 400 800
Tack: High High High High High
Washability: Excellent Good Good Excellent Good
Shear: Low Medium High Low Medium
It is apparent from compositions 1 and 4 in Table 1 that even a small percentage of the thermoplastic rubber gives a considerable enhancement of peel strength without destroying .washability. Moreover composition 1 has greater peel strength than the somewhat different composition 5 which includes ethylene/acrylic acid copolymer.

Claims

10CLAIMS:
1. A hot melt composition comprising
3 to 50 wt% of a thermoplastic rubber 10 to 50 wt% of a copolymer of vinyl pyrrolidone and vinyl acetate
10 to 50 wt% of monocarboxylic fatty acid having 8 to 22 carbon atoms.
2. A composition according to claim 1 wherein the rubber is a block copolymer of monomers with one and two olefinic unsaturations.
3. A composition according to claim 2 wherein the rubber is a styrene/isoprene block copolymer or a styrene/butadiene block copolymer.
4. A composition according to claim 1 comprising 4 to 20 wt% of the rubber.
5. A composition according to claim 1 wherein at least half the fatty acid has a carbon chain length of 10 to 14 carboy atoms.
6. A composition according to claim 1 containing 15 to 40 wt% of the fatty acid.
7. A composition according to claim 1 containing 15 to 40 wt% of the copolymer of vinyl acetate and vinyl pyrrolidone.
8. A composition according to claim 1 containing 10 to 50 wt% of tackifying resin.
9. A composition according to claim 1 containing 2 to 10 wt% of a plasticiser.
PCT/US1992/003521 1991-05-28 1992-04-30 Water dispersible pressure sensitive hot melts WO1992021718A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU19090/92A AU656980B2 (en) 1991-05-28 1992-04-30 Water dispersible pressure sensitive hot melts
JP4511454A JPH06508165A (en) 1991-05-28 1992-04-30 Water-dispersible pressure-sensitive heat melt
EP92911262A EP0586478B1 (en) 1991-05-28 1992-04-30 Water dispersible pressure sensitive hot melts
DE69208658T DE69208658T2 (en) 1991-05-28 1992-04-30 WATER-DISPERSIBLE, PRESSURE-SENSITIVE HOT MELT ADHESIVE

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US705,979 1991-05-28
US07/705,979 US5182323A (en) 1991-05-28 1991-05-28 Water dispersible pressure sensitive hot melts

Publications (1)

Publication Number Publication Date
WO1992021718A1 true WO1992021718A1 (en) 1992-12-10

Family

ID=24835716

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1992/003521 WO1992021718A1 (en) 1991-05-28 1992-04-30 Water dispersible pressure sensitive hot melts

Country Status (7)

Country Link
US (1) US5182323A (en)
EP (1) EP0586478B1 (en)
JP (1) JPH06508165A (en)
AU (1) AU656980B2 (en)
CA (1) CA2107784A1 (en)
DE (1) DE69208658T2 (en)
WO (1) WO1992021718A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5532306A (en) * 1994-08-31 1996-07-02 National Starch And Chemical Investment Holding Corporation Water-sensitive rubber-based hot melt adhesives
EP1038910A1 (en) * 1995-08-11 2000-09-27 Henkel Kommanditgesellschaft auf Aktien Solutions of colophony resins

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GB2299035B (en) * 1995-03-20 1998-06-03 Whiley Foils Ltd Hot-stamping foils
US5985095A (en) * 1997-06-06 1999-11-16 Avery Dennison Corporation Process for removing contaminants from paper pulp using a deinking composition comprising pressure-sensitive-adhesive
DE602004014593D1 (en) * 2003-02-21 2008-08-07 Kraton Polymers Res Bv LABEL PREMATURE WITH IMPROVED PUNCHING BEHAVIOR
US20070009582A1 (en) * 2003-10-07 2007-01-11 Madsen Niels J Composition useful as an adhesive and use of such a composition
EP1553149A1 (en) * 2003-12-31 2005-07-13 Kraton Polymers Research B.V. Low viscosity, hot-melt stable adhesive compositions
FR2912153B1 (en) * 2007-02-02 2009-04-17 Bostik S A Sa ADHESIVE COMPOSITION FOR SELF-ADHESIVE DECOLLABLE LABEL
FR2918069B1 (en) * 2007-06-29 2009-09-04 Bostik S A Sa HMPSA FOR SELF ADHESIVE LABEL DECOLLABLE
GB0904582D0 (en) * 2008-09-24 2009-04-29 Lumina Adhesives Switchable adhesives
KR101651709B1 (en) 2009-04-28 2016-08-26 쓰리엠 이노베이티브 프로퍼티즈 컴파니 Water-soluble pressure sensitive adhesives
EP2371920A1 (en) 2010-03-31 2011-10-05 Lumina Adhesives AB Switchable adhesives
DE102012208597B4 (en) 2012-05-23 2018-05-30 Tesa Se Pressure-sensitive adhesive for medical purposes, process for their preparation and the mixture containing pressure-sensitive adhesive
GB202002659D0 (en) 2020-02-25 2020-04-08 Lumina Adhesives Ab Switchable adhesive compositions
GB2623742A (en) 2022-10-14 2024-05-01 Lumina Adhesives Ab Adhesive compositions
PT118403A (en) * 2022-12-16 2024-06-17 Colquimica Industria Nac De Colas S A WASHABLE HOT FUSE GLUE

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US3471432A (en) * 1965-12-28 1969-10-07 Shell Oil Co Polyisoprene with branched-chain monocarboxylic acid for improving processability
US4331576A (en) * 1981-01-29 1982-05-25 Herman Colon Water-soluble, pressure-sensitive, hot-melt adhesives

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Publication number Priority date Publication date Assignee Title
US2608540A (en) * 1950-01-24 1952-08-26 Barbara W Pare Thermoplastic adhesive
US3471432A (en) * 1965-12-28 1969-10-07 Shell Oil Co Polyisoprene with branched-chain monocarboxylic acid for improving processability
US4331576A (en) * 1981-01-29 1982-05-25 Herman Colon Water-soluble, pressure-sensitive, hot-melt adhesives

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5532306A (en) * 1994-08-31 1996-07-02 National Starch And Chemical Investment Holding Corporation Water-sensitive rubber-based hot melt adhesives
EP1038910A1 (en) * 1995-08-11 2000-09-27 Henkel Kommanditgesellschaft auf Aktien Solutions of colophony resins

Also Published As

Publication number Publication date
EP0586478A4 (en) 1994-06-15
DE69208658D1 (en) 1996-04-04
DE69208658T2 (en) 1996-08-22
AU1909092A (en) 1993-01-08
CA2107784A1 (en) 1992-11-29
JPH06508165A (en) 1994-09-14
EP0586478A1 (en) 1994-03-16
US5182323A (en) 1993-01-26
EP0586478B1 (en) 1996-02-28
AU656980B2 (en) 1995-02-23

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