WO1995019231A1 - Heat reactivatable adhesive - Google Patents
Heat reactivatable adhesive Download PDFInfo
- Publication number
- WO1995019231A1 WO1995019231A1 PCT/US1995/000418 US9500418W WO9519231A1 WO 1995019231 A1 WO1995019231 A1 WO 1995019231A1 US 9500418 W US9500418 W US 9500418W WO 9519231 A1 WO9519231 A1 WO 9519231A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- weight percent
- styrene
- vinyl acetate
- ethylene
- adhesive
- Prior art date
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
- C09J125/00—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 an aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
- C09J125/02—Homopolymers or copolymers of hydrocarbons
- C09J125/04—Homopolymers or copolymers of styrene
- C09J125/08—Copolymers of styrene
- C09J125/14—Copolymers of styrene with unsaturated esters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J123/04—Homopolymers or copolymers of ethene
- C09J123/08—Copolymers of ethene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, 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 an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, 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 an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
- C08L25/14—Copolymers of styrene with unsaturated esters
-
- 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
-
- 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
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
- C08L91/06—Waxes
-
- 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
- C09J2423/00—Presence of polyolefin
-
- 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
- C09J2425/00—Presence of styrenic polymer
Definitions
- This invention relates to water-based adhesives for bladder pressing, vacuum pressing and laminating vinyl to wood substrates. BACKGROUND OF THE INVENTION
- U.S. Patent 4,396,738 Ashland describes a wood-to-wood adhesive made with a vinyl polymer and a partially reacted polyisocyanate.
- U.S. Patent 4,433,095 Bayer describes a wood-to-wood adhesive made from aromatic isocyanate and an emulsifier made from isocyanate and alcohol.
- U.S. Patent 4,609,690 Ashland describes a wood laminating adhesive curable at room temperature which combines an aqueous hydroxyl-functional acrylic latex with emulsified multi-isocyanate crosslinking agent. None of these wood-to-wood adhesives makes very strong bonds when used to adhere vinyl substrates to wood substrates. They also suffer from the drawback of having very short pot-lives. Various adhesives especially designed for adhering wood to vinyl have been developed. Because vinyl softens at temperatures around 200°F, these vinyl to wood adhesives must activate or cure below 200°F, they must however be able to withstand high temperatures because the adhered substrates are used in hot kitchens, mobile homes, and automobile interiors where temperatures may climb above 200°F for short time periods.
- European Patent Application 367120 Air Products describes a water- based adhesive for laminating vinyl substrates to wood which consists essentially of vinyl acetate-ethylene emulsion copolymer and water dispersible polyisocyanate, has a pot life of 6 hours and passes a heat and creep resistant test at 170°F.
- European Patent Application 444259 Bayer describes a laminating adhesive for PVC or PVC foam and ABS made of polyurethane dispersions forming films below 70°C, copolymers of a,b-unsaturated monomers such as styrene having a softening point above 70°C, and, optionally, dispersible reactive aliphatic polyisocyanate.
- Ashland describes an adhesive for bonding a vinyl substrate to a rigid wood substrate.
- the adhesive is an aqueous emulsion of butylacrylate-methylmethacrylate-2 hydroxyethyl acrylate terpolymer, polypropylene glycol and polyisocyanate having a pot life of at least one hour.
- This adhesive is applied by roll coater to one substrate, the second vinyl substrate is applied immediately.
- the manufacturer of wood- vinyl laminates uses the bonding adhesive directly and must see that coating equipment spreads the liquid adhesive evenly and completely.
- This invention is a method of using a heat-activatable adhesive for laminating vinyl sheet to wood substrates.
- This solvent-free adhesive combines a reactive styrene-acrylic latex emulsion and an ethylene vinyl acetate copolymer emulsion; both having certain glass transition temperatures (Tg) as measured by ASTME 1356.
- Tg glass transition temperatures
- one or more of itaconic acid, glyoxal, zinc acetyl acetonate catalyst, and a stable nonreactive aliphatic water-based polyurethane dispersion, also having a specific Tg may be added.
- the adhesive After applying the adhesive on the vinyl, the adhesive is dried, the coated vinyl is rolled and shipped to the customer.
- the customer forms or laminates the adhesive coated vinyl on to the customer's wood substrate and the adhesive is heat activated at temperatures of 160°F or 170°F depending on the combination of ingredients in the adhesive. After lamination to a wood substrate the laminate resists temperatures greater than 200°F. DESCRIPTION OF THE PREFERRED EMBODIMENTS
- Vinyl films which can be used in the present invention include cast, calendered and extruded vinyl films. Suitable vinyl films, include polyvinyl chloride, copolymers of vinyl chloride, such as vinyl chloride-vinyl acetate copolymers, polyvinyl fluoride, polyvinyl formal, polyvinylidene chloride, polyvinyl butyral, polyvinylidene fluoride, and the like.
- the preferred vinyl film for use in the present invention is a polyvinyl chloride film. Vinyl films of any thickness between 4 and 30 mils may be used in the present invention. It is not necessary to use a primer on vinyl substrates when the "primerless" adhesive of this invention is used. Among other useful flexible substrates are paper and cloth.
- Suitable substrates for lamination with the adhesive of this invention may be fibrous, non-fibrous, porous and non-porous, metallic and non-metallic, polymeric, leather, cork, wood and glass.
- the preferred rigid substrate in the practice of this invention is particle board.
- the first ingredient of the adhesive of this invention is a reactive styrene-acrylic latex emulsion.
- This emulsion can be made from acrylic acid, methyl methacrylate, styrene, hydroxy ethyl acrylate, butyl acrylate polymer, water and ethyl acrylate.
- the pH may be 6.5 to 8.
- Useful reactive styrene- acrylic latex emulsions include: Rohm & Haas 76 RES 1026 emulsion -32°C Tg ⁇ 6°C
- the most preferred reactive styrene-acrylic latex emulsion is that having a Tg of 45 ⁇ 6°C for making laminates having the best strength at room temperature.
- the most preferred styrene acrylic has a bimodal Tg distribution of 12 ⁇ 6°C and 48 ⁇ 6°C.
- the second ingredient of the adhesive of this invention is an ethylene- vinyl acetate copolymer emulsion having a Tg between -5°C and 10°C such as that available from Rohm and Haas, Philadelphia, Pennsylvania as LAM.2 emulsion (Tg 10 ⁇ 10°C) or from Air Products, Allentown, Pennsylvania, as Airflex 465 emulsion (Tg -5°C ⁇ 3°C). From 30 to 70 weight percent ethylene- vinyl acetate copolymer emulsion is used in the adhesive of this invention.
- Optional ingredients for addition to the adhesive of this invention include a stable non-reactive aliphatic water based urethane having an ionic charge such as Q-Thane QW-16 urethane available from K.J. Quinn, Seabrook, New Hampshire, having a Tg -26°C ⁇ 11 °C, a polyether based aliphatic polyurethane. From 16 to 35 weight percent aliphatic water based urethane may be used ' ⁇ - he adhesive of this invention.
- Glyoxal is another optional ingredient. Glyoxal is available from Aldrich Chemical, Milwaukee, Wisconsin. Up to 6 weight percent glyoxal may be used.
- Itaconic acid, acrylic acid and methacry c acid are other optional ingredients and are available from Aldrich Chemical. Up to 6 weight percent acid may be used in the adhesive of this invention.
- Zinc acetyl acetonate catalyst is a further optional ingredient, 0.01 to 0.5 weight percent may be used in the adhesive of this invention.
- this invention is a method of making a heat stable laminate of a flexible substrate and a solid substrate adhered together by the dried residue of a heat activatable 55 to 65 weight percent reactive styrene- acrylic emulsion, 35 to 45 weight percent ethylene-vinylacetate emulsion and 1 to 3 percent itaconic acid.
- the adhesive of this invention is prepared by first admixing the urethane and other optional ingredients with the ethylene-vinyl acetate copolymer. To this mixture the styrene-acrylic copolymer is added. These are mixed for 30 minutes. The adhesive can then be used immediately or stored for at least two months without detrimental effects on its bonding capability. If a higher viscosity product is desired, cellulosic and urethane based thickening agents can be added. Silica based products and extenders can also be added at this point.
- the adhesive of this invention is used by coating the adhesive by any of a variety of common coating methods onto a vinyl or paper substrate and drying.
- the coated substrate is then heat reactivated at temperatures greater than 150°F (65°C) and pressed onto the second substrate of choice, which may be wood, steel, glass or foam.
- Bladder pressing, nip rolling, and vacuum pressing are common methods for accomplishing this.
- Match metal presses, roller presses and platen presses may also be used.
- peel strengths means pounds per linear inch at room temperature and at 180°F (82°C) of vinyl-wood laminates.
- Preheated means heated to 71 °C for 3 minutes, cooled, then applied to wood substrate RT is room temperature
- Example 1 and Table 1 show that a laminating adhesive activated at 170°F (77°C), strong at room temperature and 180°F (82°C) testing can be made by combining styrene-acrylic latex and ethylene vinyl acetate. Addition of one or more of zinc acetyl acetonate catalyst, glyoxal, or itaconic acid improves the strength of the vinyl to wood bond at room temperature and at 180°F (82°C) testing.
- Example 2 describes formulations displaying the ability to be activated
- Example 2 and Table 2 show that a laminating adhesive activatable at 160°F (71 °C) can be prepared by combining ethylene vinyl acetate, styrene acrylic with Tg 35°C - 48°C and aliphatic water based urethane (footnote 4).
- An adhesive activatable at 160°F (71 °C) can also be prepared by combining
- Example 3 compares peel strength and substrate fiber tear of laminating adhesives of this invention made with RES 1026 styrene acrylic having a Tg
- LAM 2 10°C (LAM 2) at different levels of water based urethane.
- the vinyl to particle board laminates were made at 160°F (71 °C), using 2 atmospheres pressure for 3 minutes. Fiber tear was tested at room temperature.
- Table 3 shows that optimum levels of water based urethane are 25 to 30 percent and that ethylene vinyl acetate polymers having Tg of -5 ⁇ 3°C and 10°C ⁇ 10°C are effective in the laminating adhesive of this invention.
- Styrene acrylic emulsions having various glass transition temperatures are combined with ethylene vinyl acetate and different levels of aliphatic water based urethane.
- urethane are 35 to 30 percent and that styrene acrylic emulsion having Tg from -32°C to +50°C are effective in the laminating adhesive of this invention.
- the most preferred laminating adhesive for strong bonds between vinyl and wood when tested at room temperature is a mixture of a styrene acrylic latex emulsion having a Tg of 45 ⁇ 6°C, an ethylene-vinyl acetate copolymer having a Tg of 10 ⁇ 10°C and a stable non-reactive aliphatic water based urethane.
- the most preferred laminating adhesive for strong bonds between vinyl and wood when tested at higher temperatures such as 180°F (82°C) is a mixture of a styrene acrylic latex emulsion having a bimodal glass transition temperature distribution of 12 ⁇ 6°C and 48 ⁇ 6°C, an ethylene vinyl acetate
- copolymer having a Tg of 10 ⁇ 10°C, glyoxal, itaconic acid, and, optionally, zinc acetyl acetonate catalyst.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP95909229A EP0695223A4 (en) | 1994-01-12 | 1995-01-11 | Heat reactivatable adhesive |
AU17260/95A AU1726095A (en) | 1994-01-12 | 1995-01-11 | Heat reactivatable adhesive |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18093794A | 1994-01-12 | 1994-01-12 | |
US08/180,937 | 1994-01-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995019231A1 true WO1995019231A1 (en) | 1995-07-20 |
Family
ID=22662256
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1995/000418 WO1995019231A1 (en) | 1994-01-12 | 1995-01-11 | Heat reactivatable adhesive |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0695223A4 (en) |
AU (1) | AU1726095A (en) |
WO (1) | WO1995019231A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6180244B1 (en) | 1998-02-17 | 2001-01-30 | 3M Innovative Properties Company | Waterbased thermoforming adhesives |
WO2009009216A1 (en) * | 2007-07-12 | 2009-01-15 | Dow Global Technologies Inc. | Aqueous dispersion comprising a (meth) acrylic polymer and a vinyl acetate polymer |
CN115678462A (en) * | 2021-07-30 | 2023-02-03 | 德莎欧洲股份公司 | Water-based acrylic adhesive and removable adhesive tape comprising same |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3380582A (en) * | 1965-09-03 | 1968-04-30 | Daubert Chemical Co | Insulating article and method |
US3690936A (en) * | 1970-02-02 | 1972-09-12 | Phillips Petroleum Co | Adhesive material for bonding vinyl chloride polymers to substrates |
US4396738A (en) * | 1982-05-24 | 1983-08-02 | Ashland Oil, Inc. | Aqueous adhesive compositions |
JPS58162645A (en) * | 1982-03-19 | 1983-09-27 | Dainippon Ink & Chem Inc | Adhesive for porous substrate |
US5190997A (en) * | 1985-07-10 | 1993-03-02 | Sequa Chemicals, Inc. | Adhesive composition |
JPH05117611A (en) * | 1991-10-31 | 1993-05-14 | Chuo Rika Kogyo Kk | Adhesive composition |
-
1995
- 1995-01-11 WO PCT/US1995/000418 patent/WO1995019231A1/en not_active Application Discontinuation
- 1995-01-11 AU AU17260/95A patent/AU1726095A/en not_active Abandoned
- 1995-01-11 EP EP95909229A patent/EP0695223A4/en not_active Ceased
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3380582A (en) * | 1965-09-03 | 1968-04-30 | Daubert Chemical Co | Insulating article and method |
US3690936A (en) * | 1970-02-02 | 1972-09-12 | Phillips Petroleum Co | Adhesive material for bonding vinyl chloride polymers to substrates |
JPS58162645A (en) * | 1982-03-19 | 1983-09-27 | Dainippon Ink & Chem Inc | Adhesive for porous substrate |
US4396738A (en) * | 1982-05-24 | 1983-08-02 | Ashland Oil, Inc. | Aqueous adhesive compositions |
US5190997A (en) * | 1985-07-10 | 1993-03-02 | Sequa Chemicals, Inc. | Adhesive composition |
JPH05117611A (en) * | 1991-10-31 | 1993-05-14 | Chuo Rika Kogyo Kk | Adhesive composition |
Non-Patent Citations (1)
Title |
---|
See also references of EP0695223A4 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6180244B1 (en) | 1998-02-17 | 2001-01-30 | 3M Innovative Properties Company | Waterbased thermoforming adhesives |
WO2009009216A1 (en) * | 2007-07-12 | 2009-01-15 | Dow Global Technologies Inc. | Aqueous dispersion comprising a (meth) acrylic polymer and a vinyl acetate polymer |
CN115678462A (en) * | 2021-07-30 | 2023-02-03 | 德莎欧洲股份公司 | Water-based acrylic adhesive and removable adhesive tape comprising same |
Also Published As
Publication number | Publication date |
---|---|
AU1726095A (en) | 1995-08-01 |
EP0695223A4 (en) | 1997-12-10 |
EP0695223A1 (en) | 1996-02-07 |
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