WO2000016164A1 - Adhesives for preparing a multilayer laminate featuring an ink-bearing surface bonded to a second surface - Google Patents
Adhesives for preparing a multilayer laminate featuring an ink-bearing surface bonded to a second surface Download PDFInfo
- Publication number
- WO2000016164A1 WO2000016164A1 PCT/US1999/020612 US9920612W WO0016164A1 WO 2000016164 A1 WO2000016164 A1 WO 2000016164A1 US 9920612 W US9920612 W US 9920612W WO 0016164 A1 WO0016164 A1 WO 0016164A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ink
- polymeric substrate
- polymeric
- major surface
- image
- Prior art date
Links
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G8/00—Layers covering the final reproduction, e.g. for protecting, for writing thereon
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- 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
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/58—Epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/06—Polyurethanes from polyesters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G13/00—Electrographic processes using a charge pattern
Definitions
- This invention relates to adhesives for use in multilayer laminates in which at least one of the layers includes an ink-bearing surface.
- the invention features an adhesive composition that includes the reaction product of: (a) a polyester-based polyurethane; (b) an epoxy resin; (c) an epoxy-functional silane; and (d) an isocyanate-functional compound.
- the adhesive compositions are useful for preparing multilayer laminates in which a major surface of a first polymeric substrate is bonded to a major surface of a second polymeric substrate through the adhesive composition. One or both of those major surfaces includes an ink-bearing image.
- the adhesive compositions exhibit good adhesion (as measured by the 180 degree peel strength) to both ink-bearing polymeric substrates and non-ink bearing polymeric substrates.
- the compositions are particularly useful where the ink is an electrophotographic ink.
- suitable electrophotographic inks include polymers having a Tg no greater than about 30°C, while in other embodiments the ink includes a polymer having a Tg greater than about 30°C.
- One example of a suitable ink is derived from gel organo sol-containing, liquid toner compositions described, e.g., in Baker et al., U.S. 5,652,282 and Baker et al., U.S. 5,698,616.
- toners include (a) a carrier liquid (e.g., an aliphatic hydrocarbon carrier liquid having a Kauri-Butanol number less than 30) and (b) a (co)polymeric steric stabilizer having a molecular weight greater than or equal to 50,000 Daltons and a polydispersity less than 15 covalently bonded to a thermoplastic (co)polymeric core that is insoluble in the carrier liquid.
- the core preferably has a Tg no greater than about 30°C.
- the toner may further include a colorant and a charge director.
- non-gel organo sol-containing liquid toner compositions described, for example, in Baker et al., U.S. 5,886,067.
- a suitable ink is derived from liquid toners described in Landa et al., U.S. 4,794,651; Landa et al., U.S. 4,842,974; Landa et al., U.S. 5,047,306; Landa et al., 5,047,307; Landa et al., U.S. 5,192,638; Landa et al., U.S. 5,208,130; Landa et al., U.S. 5,225,306; Landa et al., U.S. 5,264,313; Landa et al., U.S. 5,266,435; Landa et al., U.S.
- compositions are also useful with inks such as ink jet inks and lithographic inks. Any of these inks may be used alone or in combination with each other.
- the ink-bearing surface may include electrophotographically printed areas featuring an electrophotographic ink and offset printed areas featuring a lithographic ink. Preferably, however, all the printed areas of the laminate are electrophotographically printed areas featuring an electrophotographic ink.
- the adhesive compositions exhibit good adhesion to a number of polymeric substrates.
- the adhesive is used to bond a rigid core layer to a flexible overlay film, where at least one of these materials includes an ink-bearing surface.
- at least one of the substrates is substantially transparent to permit viewing of the printed image on the ink-bearing surface.
- suitable polymeric substrates are selected from the group consisting of polyvinyl chloride, vinyl chloride- vinyl acetate copolymers, polyesters, polyolefins, polycarbonates, and combinations thereof. Also suitable are microporous substrates such as that available under the trade designation TESLIN films commercially available from PPG, Inc. of Pittsburgh, PA.
- One preferred construction includes a polyvinyl chloride substrate adhesively bonded to a substantially transparent polyester overlay film.
- the adhesive compositions are also useful for preparing laminated articles having more than two substrates.
- the article may include a core substrate having a pair of opposed major surfaces, each of which is bonded to a separate overlay film.
- Such constructions are particularly useful for articles having printed images on two different surfaces.
- the invention features a lamination process for
- the ink-bearing image preferably is performed according to an electrophotographic imaging process that includes:
- the toner preferably is a liquid toner.
- Preferred liquid toners include a film-forming polymer.
- the film-forming polymer has a Tg no greater than about 30°C, while in other embodiments the film-forming polymer has a Tg greater than about 30°C.
- the article may subjected to a number of operations, including slitting, cutting, hole punching and drilling, foil stamping, sewing and grommeting, foil stamping, perforation, folding, surface texturing, and the like.
- the black, positive-acting, film-forming, electrophotographic ink used in the examples was prepared at an organosol/pigment ratio of 6 following the procedure described in Example 40 of U.S. 5,652,282 modified as follows.
- the gel organosol prepared according to the procedure of Example 22 of U.S. 5,652,282 was mixed using a Silverson mixer (Model L2R, Silverson Machines, Ltd.) operated at the lowest speed setting. After mixing for five minutes, 1912 g of the homogenized organosol at 16.14% (w/w) solids in NORPAR 12 were combined with 1031 g of NORPAR 12 (Exxon Chemical Co., Houston, TX), 51 g of MONARCH 120 carbon black (Cabot Corp., Billerica, MA), and 6.08 g of Zirconium HEX-CEM (OMG Chemical Company, Cleveland, OH) in a 4.0 liter polyethylene container.
- a Silverson mixer Model L2R, Silverson Machines, Ltd.
- This mixture was then milled in ten vertical bead mills, each having a capacity of 0.5 liter (Model 6TSG-1/4, Aimex Co. Ltd., Tokyo, Japan) by placing 300 g of millbase and 390 g of 1.3 mm diameter Potters glass beads (Potters Industries, Inc., Parsippany, NJ)
- each mill was operated at 2,000 rpm for 1.5 hours without cooling water circulating through the cooling jacket of the milling chamber.
- An adhesive coating solution was prepared by adding methyl ethyl ketone (201 g), Epon 1007F epoxy resin (143 g of a 20 wt. % solution in methyl ethyl ketone, available from Shell Chemical Co.), epoxycyclohexylethyl trimethoxy silane (14.4 g, available from Aldrich Chemical Co.), and Nestanat T1890E isocyanate (215 g of a 20 wt. % solution in methyl ethyl ketone, available from Creanova) to 1428 g of a solution of Desmocoll 8634 polyurethane resin (15 wt. % in methyl ethyl ketone, available from Bayer Chemical Co.). The solution was applied to Mellinex 454 polyester film (0.92 mil, available from Dupont) at a wet coating coverage of approximately 375 g/square meter and dried to give an adhesive-coated film. The dry thickness of the adhesive layer was 1.0 mil.
- the adhesive portion of the film was area printed using a liquid toner- based, black, positive-acting, film-forming, electrophotographic ink (prepared as described above) to a net optical density of 1.6.
- the net optical density is equal to the white light optical density minus the white light optical density of unprinted film, measured in reflectance mode with a Macbeth densitometer.
- the net optical density corresponded to an ink net optical density of 1.3 for a paper substrate printed under identical conditions.
- the article was cut into strips measuring one inch wide and the 180 degree peel force required to cause delamination was measured 15 minutes after the lamination step using an Instron Tester (Model 5542). The crosshead speed was 12 inches/minute. The peel force was determined to be 4.5 pounds/inch (7.9 ⁇ /cm).
- a laminated article was prepared following the procedure of Example 1 except that lamination took place 30 minutes after printing.
- the peel strength was determined to be 1.9 pounds/inch (3.4 N/cm).
- the experiment was then repeated except that subsequent to the printing step, the printed polyester film was heated at 100°C for 2 minutes and then laminated after a total of thirty minutes had elapsed since the printing step.
- the peel force measured approximately five minutes after the lamination, was 2.4 pounds/inch (4.2 N/cm).
- Example 1 The procedure of Example 1 was followed except that the adhesive was prepared by combining 15 parts Desmocoll 530, 85 parts methyl ethyl ketone, 3 parts Vestanat T1890E isocyanate, 1 part epoxycyclohexylethyl trimethoxy silane, and 2 parts Epon 1007F epoxy resin.
- the resulting article exhibited a peel force, measured as described in Example 1, of 4.0 pounds/inch (7.0 N/cm).
- the failure mode was ink splitting.
- the resulting article was stored for two weeks at 60°C and 100% relative humidity, after which the peel strength was measured and determined to be 10 pounds/inch (17.6 N/cm).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Laminated Bodies (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000570639A JP2002525389A (en) | 1998-09-11 | 1999-09-09 | Adhesive for making a multilayer laminate characterized by an ink-containing surface bonded to a second surface |
KR1020017003110A KR20010073144A (en) | 1998-09-11 | 1999-09-09 | Adhesives for Preparing a Multilayer Laminate Featuring an Ink-Bearing Surface Bonded to a Second Surface |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10001098P | 1998-09-11 | 1998-09-11 | |
US60/100,010 | 1998-09-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000016164A1 true WO2000016164A1 (en) | 2000-03-23 |
Family
ID=22277671
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1999/020612 WO2000016164A1 (en) | 1998-09-11 | 1999-09-09 | Adhesives for preparing a multilayer laminate featuring an ink-bearing surface bonded to a second surface |
Country Status (3)
Country | Link |
---|---|
JP (1) | JP2002525389A (en) |
KR (1) | KR20010073144A (en) |
WO (1) | WO2000016164A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100932668B1 (en) * | 2001-12-14 | 2009-12-21 | 가부시키가이샤 시마노 | Surface treatment method |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100822731B1 (en) * | 2006-10-02 | 2008-04-17 | 삼화페인트공업주식회사 | Adhesive composition of one component for adhering metal film on plated steel sheet |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4315980A (en) * | 1979-04-09 | 1982-02-16 | Fuji Xerox Co., Ltd. | Electrophotographic member with metallocene containing overlayer |
EP0443626A2 (en) * | 1990-02-23 | 1991-08-28 | Idemitsu Petrochemical Co. Ltd. | Electrophotographic photosensensitive member |
US5393628A (en) * | 1992-06-25 | 1995-02-28 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, and electrophotographic apparatus employing the same |
US5876910A (en) * | 1997-10-20 | 1999-03-02 | Eastman Kodak Company | Aqueous coating compositions for surface protective layers for imaging elements |
-
1999
- 1999-09-09 KR KR1020017003110A patent/KR20010073144A/en not_active Application Discontinuation
- 1999-09-09 WO PCT/US1999/020612 patent/WO2000016164A1/en not_active Application Discontinuation
- 1999-09-09 JP JP2000570639A patent/JP2002525389A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4315980A (en) * | 1979-04-09 | 1982-02-16 | Fuji Xerox Co., Ltd. | Electrophotographic member with metallocene containing overlayer |
EP0443626A2 (en) * | 1990-02-23 | 1991-08-28 | Idemitsu Petrochemical Co. Ltd. | Electrophotographic photosensensitive member |
US5393628A (en) * | 1992-06-25 | 1995-02-28 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, and electrophotographic apparatus employing the same |
US5876910A (en) * | 1997-10-20 | 1999-03-02 | Eastman Kodak Company | Aqueous coating compositions for surface protective layers for imaging elements |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100932668B1 (en) * | 2001-12-14 | 2009-12-21 | 가부시키가이샤 시마노 | Surface treatment method |
Also Published As
Publication number | Publication date |
---|---|
JP2002525389A (en) | 2002-08-13 |
KR20010073144A (en) | 2001-07-31 |
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