WO1997009388A1 - Articles coated with electrophotographic toner receptive release coatings - Google Patents
Articles coated with electrophotographic toner receptive release coatings Download PDFInfo
- Publication number
- WO1997009388A1 WO1997009388A1 PCT/US1996/012286 US9612286W WO9709388A1 WO 1997009388 A1 WO1997009388 A1 WO 1997009388A1 US 9612286 W US9612286 W US 9612286W WO 9709388 A1 WO9709388 A1 WO 9709388A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- independently
- same
- aryl
- different
- 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/10—Block or graft copolymers containing polysiloxane sequences
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G7/00—Selection of materials for use in image-receiving members, i.e. for reversal by physical contact; Manufacture thereof
- G03G7/006—Substrates for image-receiving members; Image-receiving members comprising only one layer
- G03G7/0073—Organic components thereof
- G03G7/008—Organic components thereof being macromolecular
Definitions
- the present invention relates to release coatings and articles coated with such release coatings.
- the present invention relates to release coatings which anchor printed indicia, even when contacting a repositionable pressure-sensitive adhesive.
- a well known note pad comprises a stack of paper sheets, each having a narrow strip of low-tack pressure-sensitive adhesive adjacent one edge on its rear side by which the sheets can be temporarily adhered to substrates such as documents or other articles (often for message-bearing purposes), by which strip of adhesive the sheets are adhered together in the pad.
- all of the strips of adhesive are along one side ofthe note pad, whereas in another pad configuration the adhesive strip on each successive sheet in the pad is along the opposite side ofthe pad as is illustrated in U.S. Patent No. 4,416,392.
- Note pads in both of these configurations are currently being marketed under the trademark "Post-it” by Minnesota Mining and Manufacturing Company, St. Paul, Minnesota.
- a number of conventional electrophotoconductive devices such as printers and copiers employ dry toner. These printers and/or copiers employ toner to form a latent image transferable from an imaging device to a substrate such as paper, tag or label stock. The toned latent image is then subjected to heat fusing in order to obtain the best print quality and toned image density.
- the residual ink is transferred to another roller in the printer and subsequently transferred to the substrate out of register. This results in a lightly colored image. Additional problems with ink jet printing is the tendancy of ink to dewet from the substrate, and failure to absorb into the substrate or dry. In either case, the ink is smeared when a subsequent sheet contacts the image.
- a release coating is typically used to provide facile removal ofthe sheets from pads.
- Such a release coating must be receptive to common writing instruments and printing inks (see U.W. Patent No. 5,154,962 columns 1 and 2 related background).
- the release coating is selected to permit high quality images with specific printing technologies and ready separation from the adhesive.
- the release-coated substrate must accept and firmly anchor indicia.
- the coated substrate must first accept the inidicia without "backgrounding” in electrophotographic devices, "ghosting” in some printers, or smearing in liquid ink printers. Additionally, when formed into pads, the printed indicia must firmly anchor to the substrate without transferring to the adhesive ofthe preceding note in the pad. Coatings have been prepared to enhance ink or toner particle receptivity.
- the present invention comprises articles coated release coatings that are capable of accepting and anchoring printed indicia and yet, maintains good release properties.
- the release coating ofthe present invention is coated onto a substrate such as paper.
- the articles are ofthe form described in U.S. Patent No. 5,382,055 and are useful to prepare a small amount of notes or note pads.
- the release coating comprises a polymer having at least one vinyl polymeric segment having a T g between -10°C and 65°C and at least one siloxane polymeric segment.
- the Tg should be between 200C and 450C ofthe vinyl polymer segment.
- the coating is a copolymer which comprises the formula:
- Ri are monovalent moieties which can independently be the same or different and are selected from the group consisting of alkyl, aryl, alkaryl, alkoxy, alkylamino, hydroxyl, hydrogen, and fluoroalkyl;
- R 2 can independently be the same or different and are divalent linking groups;
- R 3 are monovalent moieties which can independently be the same or different and are selected from the group consisting of alkyl, aryl, alkylaryl, alkoxy, alkylamino, hydroxyl, hydrogen, and fluoroalkyl;
- R 4 can independently be the same or different and are divalent linking groups; x is an integer of 0 to 3; y is an integer of 10 or greater; q is an integer of 0 to 3 ;
- Gs and G 6 are monovalent moieties which can independently be the same or different selected from the group consisting of alkyl, aryl, alkaryl, alkoxy, alkylamino, fluoralkyl, hydrogen, and -WSA wherein W is a divalent linking group and A is defined below; and G 2 and G 4 are A wherein A is a vinyl polymeric segment or block consisting essentially ofa polymerized free radically polymerized monomer.
- the coating comprises a copolymer of D and E monomers copolymerized to form a polymeric backbone with F monomer grafted thereto wherein: D is at least one free radically polymerizable vinyl monomer;
- E is at least one polar monomer copolymerizable with D, the amount of E being up to 30% ofthe total weight of all monomers
- F is a monomer having the general formula X-(Y) n SiR (3Hrift)Z m wherein X is a vinyl group copolymerizable with the D and E monomers
- Y is a divalent linking group where n is zero or 1; m is an integer of 1 to 3;
- R is hydrogen, lower alkyl (e.g., methyl, ethyl, or propyl), aryl (e.g., phenyl or substituted phenyl), or alkoxy groups; and z is a monovalent siloxane polymeric moiety having a number average molecular weight above about 1,000 and is essentially unreactive under copolymerization conditions.
- the present invention also includes a toner receptive article comprising a liner, a release coating and a substrate such as a label mounted over the liner.
- Figure 1 is a representation of an embodiment of Applicants' invention tested in accordance with the procedures described below.
- Figure 2 is a representation of Avery 30-up stock #5160 that has been tested in accordance with the procedures described below.
- Figure 3 is an edge view of a sheet assembly according to the present invention.
- Figure 4 is a reduced sectional view taken approximately along line 4-4 of Figure 3.
- the present invention includes an article coated with a release coating that is capable of anchoring toner.
- the release coating has at least one siloxane polymeric segment and at least one vinyl polymeric segment having a T g between -10°C and 65°C.
- the release coating is well-suited to control toner anchorage applications.
- the silicone segment presents a low energy, "siliconized" release surface and the higher energy vinyl polymeric segment provides the adhesion for the toner particles.
- the coating is a copolymer which comprises the formula:
- Ri are monovalent moieties which can independently be the same or different which are selected from the group consisting of alkyl, aryl, alkylaryl, alkoxy, alkylamino, hydroxyl, fluoroalkyl, and hydrogen.
- Ri are monovalent moieties which can independently be the same or different selected from the group consisting of Cw alkyl and hydroxyl.
- R is selected from the group consisting of methyl and butyl.
- R 2 are divalent linking groups which can independently be the same or different. Suitable divalent linking groups include but are not limited to the following: Ci to Cio alkylene, arylene, alkylarylene and alkoxyalkylene. Preferably, R 2 is selected from the group consisting of C ⁇ . 3 alkylene and C 7 -C ⁇ o alkylarylene due to ease of synthesis ofthe compound. Most preferably, R 2 is selected from the group consisting of -CH 2 -; 1,3-propylene; and
- R 3 are monovalent moieties which can independently be the same or different which are selected from the group consisting of alkyl, aryl, alkaryl, alkoxy, alkylamino, hydroxyl and fluoroalkyl, and hydrogen.
- R 3 are monovalent moieties which can independently be the same or different selected from the group consisting of Cw alkyl and hydroxyl.
- R 3 is selected from the group consisting of methyl and butyl.
- P are divalent linking groups which can independently be the same or different. Suitable divalent linking groups include but are not limited to the following: Q to do alkylene, arylene, alkylarylene and alkoxyalkylene.
- P is selected from the group consisting of d -3 alkylene and C 7 -C ⁇ o alkylarylene for reasons of ease of synthesis.
- R 4 is selected from the group consisting of -CH 2 -; 1,3 -propylene; and
- G5 and G ⁇ are monovalent moieties which can independently be the same or different selected from the group consisting of alkyl, aryl, alkylaryl, alkoxy, alkylamino, fluoralkyl, hydrogen, and -WSA wherein W is a divalent linking group and A is defined below.
- W are divalent linking groups. Suitable divalent linking groups include, but are not limited to, Ci to Cio alkylene, alkarylene, arylene, and alkoxyalkylene. Preferably, W is selected from the group consisting of methylene and propylene.
- G 2 and G 4 are the same or different and comprise A.
- A is a vinyl polymeric segment consisting essentially of polymerized free radically polymerizable monomer.
- A can comprise either a homopolymer segment or block or a copolymer segment or block.
- the toner anchorage properties ofthe coating are determined by the vinyl polymeric segment content.
- the chemical nature or composition ofthe vinyl polymeric segments can be modified independent ofthe release aspect to improve toner anchorage and adhesion to the substrate.
- the release coating can be chemically tailored to provide a specific level of toner anchorage.
- the selection ofthe composition of A is typically based upon the intended use ofthe release coating and the properties the release coating must possess in order to accomplish its intended purpose.
- A can include, but is not limited to, those monomers wherein the free radically polymerizable monomer or monomers are chosen such that a vinyl segment has a T g or T m above about -20°C.
- the preferred free radically polymerizable monomers are selected from the group consisting of styrene, methyl methacrylate, methyl acrylate, acrylic acid, methacrylic acid, acrylonitrile, isobornyl acrylate, isobornyl methacrylate, N-vinyl pyrroiidone, butyl methacrylate, isopropyl methacrylate, vinyl acetate, hydroxy propylacrylate, hydroxy ethyl acrylate and mixtures thereof.
- the amount and composition ofthe vinylic segment to silicone should range from about 98 to about 2 parts preferably, from about 40 to about 60 parts by weight. It is preferred that the vinyl polymeric segments should have a molecular weight in the range of 2,000 to 80,000, more preferably 5,000 to 50,000.
- the release properties ofthe coating are determined by both the silicone content (weight percentage) present in the copolymer and the molecular weight of the silicone segment, with higher silicone content and/or molecular weight providing easier release.
- a copolymer or copolymer blend can, therefore, be chemically tailored to provide a specific level of release which can be reproduced with consistency, thus making possible the variation ofthe release properties ofa liner over a range of values in a controlled fashion.
- the silicone polymeric segment must have an average molecular weight above about 1000 in order for the release coating to function properly.
- the silicone polymeric segment has a number average molecular weight of about 1000 to about 20,000.
- the silicone polymeric segment has a number average molecular weight ranging from about 2,000 to about 15,000.
- the silicone polymeric segment can comprise about 2 to 60 wt% ofthe release coating in order to allow for a wide range of release performance.
- the release coating comprises a copolymer of D and E monomers copolymerized to form a polymeric backbone. Grafted to the backbone is an F monomer.
- the D and E monomers provide the toner anchorage properties ofthe coating and the F monomer provides the release properties.
- the D monomer or monomers are chosen such that the backbone T g or T m is above about -20°C.
- Representative examples of D monomers include styrene, vinyl acetate, vinyl chloride, vinylidene chloride, acrylonitrile and acrylic or methacrylic acid esters of nontertiary alcohols or tertiary alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, cyclohexanol, benzyl alcohol, dodecanol, hexadecanol, and octadecanol, the alcohols having from 1 to 18 carbon atoms.
- Especially preferred D monomers include methyl methacrylate, butyl methacrylate, vinyl acetate, partially hydrolyzed vinyl acetate, methyl acrylate and octadecyl acrylate.
- Representative E monomers useful in practicing the invention include carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, and 2- carboxyethyl acrylate and their ammonium or metal salts; sulfonic or phosphonic acids such as 2-sulfoethyl methacrylate, 3 -sulfopropyl acrylate, 3 -sulfopropyl methacrylate, styrene sulfonic acid, and vinyl benzyl phosphonic acid and their ammonium or metal salts; amides such as acrylamide, methacrylamide, N,N- dimethyl acrylamide, and N-vinyl pyrroiidone; and monomers having hydroxyl functionality (e.g., 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, hydroxypropyl acrylate, and dihydroxypropyl acrylate), am
- R comprises hydrogen, lower alkyl groups such as methyl, ethyl, or propyl, aryl groups such as phenyl or substituted phenyl and alkoxy groups such as methoxy and ethoxy groups.
- Z is a monovalent siloxane polymeric moiety having a number average molecular weight above about 1,000 and is essentially unreactive under copolymerization conditions.
- the preferred F monomer may be further defined as having an X group which has the general formula
- Rl R2 I I CH C — wherein R 1 is a hydrogen atom or a COOH group and R 2 is a hydrogen atom, a methyl group, or a CH 2 COOH group.
- the Z group ofthe F monomer has the general formula
- R 3 and R 5 are independently lower alkyl, aryl, or fluoroalkyl, where lower alkyl and fluoroalkyl both refer to alkyl groups having from one to three carbon atoms and where aryl refers to phenyl or substituted phenyl.
- R 4 may be alkyl, alkoxy, alkylamino, aryl, hydroxyl, or fluoroalkyl, and r is an integer from about 5 to about 700.
- the F monomer has a general formula selected from the group consisting ofthe following, where m is 1, 2 or 3, p is zero or 1, R" may be alkyl or hydrogen, and X, R, and Z are as defined above:
- q is an integer from 2 to 6;
- q is an integer from zero to 2;
- q is an integer from 2 to 6;
- the release coating ofthe present invention may comprise the copolymers ofthe two embodiments alone, or may comprise copolymers blended with other compatible homopolymers and/or copolymers.
- the low percentage of silicone contained in the copolymers makes the copolymers readily compatible with polymers of similar composition to the vinyl Polymeric blocks or segments.
- the release coating ofthe present invention should provide sufficient anchorage to anchor at least 50% ofthe toner. It is understood that “substantially” means at levels of at least 50%. More preferably, it should anchor at least 70% of the toner.
- the release coating should have a surface release value not greater than about 10 oz./in (11 N/dm). It should be understood that this upper limit applies to use with highly aggressive pressure-sensitive adhesives (PSAs) which have peel adhesion values of 45 N/dm or higher. PSAs as a group fall into three broad categories (1) low (5-15 N/dm), (2) intermediate (25-50 N/dm), and (3) high (60-100 plus N/dm) peel adhesion ranges. It is apparent that the degree of release can be selected to match the aggressiveness ofthe PSA with which it will be in contact and it is only for the most aggressive PSAs that a release value as high as 10 oz/in. (11 N/dm) would be selected. Release coatings for less aggressive PSAs would be selected to be correspondingly lower.
- release compositions do not require curing or crosslinking; however, if solvent resistance is desired for a particular application, crosslinking can be effected by standard methods well-known in the art, such as radiation curing (electron beam or ultraviolet light) or chemical crosslinking.
- the release coating compositions may be applied to any suitable backing or liner by means of conventional coating techniques such as wire- wound rod, direct gravure, offset gravure, reverse roll, air-knife and trailing blade coating.
- Suitable liners include paper, non-woven fabrics and films of thermoplastic resins such as polyesters, polyamides, polyolefins, polycarbonates and polyvinyl chloride.
- any substrate which can be applied to a liner by a pressure sensitive adhesive can be utilized.
- paper is a suitable substrate.
- the release coating ofthe present invention is utilized as a component of label stock.
- one or more non-continuous substrates such as labels are adhered to protective liner by a suitable adhesive.
- the release coating ofthe present invention is coated the liner.
- a particularly useful configuration is a sheet assembly wherein the assembly can be described as follows and in reference to Figures 3 and 4. The sheet assembly 10 is illustrated with release coatings 40 on at least one nonadhesive bearing area of the rear surfaces 15 ofthe sheets 12 and 13.
- the release coatings 40 can be applied strips and are slightly wider than strips 16 of adhesive, and extend transversely of the sheets 12 and 13 parallel to the edges 30, 36 and 37 with each strip release coating 40 being adjacent and extending along an edge of a portion 34 ofthe sheet 12 and 13 that will be formed by separating the sheets 12 and 13 along the paths of weakness 31 and 33, and in a position such that when the rear surfaces 15 ofthe sheets are placed face to face as illustrated in Figure 3, the strip layers 16 ofthe adhesive will contact and will be generally centered on the strip release coatings 40. Also, as illustrated, the entire front surface 14 of each ofthe sheets 12 and 13 is coated with a release coating 41, althought such a coating is not necessarily required.
- the illustrated release coatings 40 on the rear surfaces 15 and the release coatings 41 on the front surface 14 ofthe sheets 12 and 13 are not needed when the layers 16 ofthe adhesive are of low-tack or repositionable adhesive (e.g., the low-tack adhesives based on tacky, elastomeric copolymer microspheres disclosed in U.S. Patent Nos. 3,961,140 and 3,857,731).
- the use of the release coatings 40 and 41 allows the use of layers 16 of pressure-sensitive adhesive that are more aggressive or permanent than repositionable adhesive.
- Suitable release coatings 40 and 41 are materials and treatments those ofthe present invention. Even with layers 16 of aggressive pressure-sensitive adhesive the release coatings 40 and 41 might not be required if the sheets 12 and 13 are of a material, or are impregnated with the release material, from which the layer 16 of adhesive readily releases.
- Figures 3 and 4 represent a particular configuration of a sheet assembly, such illustrations and descriptions are merely illustrative ofthe present invention and other embodiments could be contemplated to be within the scope of this invention.
- the polymer solutions of Examples 1 to 19 discussed below were diluted to 15% solids in distilled water.
- the solutions were then coated onto commercially available roll base paper with a gravure roll having a pyramidal pattern of 200 cells per inch. A two roll direct gravure coating was applied to each sample.
- Two different roll base papers were utilized.
- Supercalendered CIS paper supplied by the Simpson Paper Company was coated with the diluted polymer solutions of Examples 1 to 4 and machine glazed base paper sold by Akrosil were coated with the diluted polymer solutions of Examples 4 to 19. After coating, the base papers were dried at 77°C.
- the release property of an adhesive refers to ease that an adhesive separates from another surface. It is the force required to remove a flexible adhesive tape from a test sample at a specific angle and rate of removal. It is measured in
- N/dm Newtons per decimeter
- test sample was conditioned overnight at constant temperature (22°C) and humidity (50% RH). Thereafter, a 5.08 cm by 25.4 cm strip ofthe test sample is laminated to a constant 90° angle jig commercially available as the Deltron Ball Slide from the J.R. Brass Co. of Eden Prairie, MN with double coated tape. Then a 2.54 cm strip of a PSA coated (#810 tape, commercially available from the assignee of this application) test tape was rolled down onto the laminate with a 1.82 kg rubber roller. The force required to remove this tape at 90° and 30.5 cm/minute was then measured was measured by a Sintech/Instron Tensile Tester System commercially available from Sintech Corporation, a division of MTS Systems Co ⁇ oration, Research Triangle Park, North Carolina.
- the toner receptivity ofthe test samples was assessed by printing on a 21.6 cm x 27.9 cm test sample an asterisk pattern, i.e., (****), in an Hewlett Packard LaserJet II printer. The imaged coated sheets then sat overnight in a controlled environment of 21°C and 50% RH. Thereafter, a 2.54 cm x 25.4 cm strip of ScotchTM Brand 810TM tape manufactured by the Minnesota Mining and Manufacturing Company was rolled down over the imaged test samples using two passes of a 1.82 kg rubber roller. After the two passes, the test samples were allowed to sit in a controlled environment of 21°C and 50% RH for 24 hours.
- ScotchTM Brand 810TM tape was laminated image side up to the stage of in TIMI Release and Adhesion Tester sold by Testing Machines Inc. of Mityville, New York with double coated tape.
- the 810TM tape was then removed at a peel angle of 180°C at 3048 cm/minute. Image analysis was used to determine the amount of indicia which remained anchored to the coated sheet.
- KF2001 - a mercaptofunctional dimethyl siloxane with 4-5 mole % mercapto functionality commercially available from Shin-Etsu.
- Example 1 The composition of Example 1 was prepared in the following manner: First, a solvent borne sample was prepared by charging a 32 oz. reaction bottle with 45 grams of mercaptofunctional dimethyl siloxane with 4-5 mole mercapto functionality commercially available as KF-2001 from Shin-Etsu, 169 grams of methyl acrylate, 11 grams acrylic acid, 335 grams of methyl ethyl ketone (MEK) and 0.56 grams 2-2 , -azobisisobutyronitrile (AIBN). The solution mixture was then purged with nitrogen for 2 minutes at a rate of 1 L/min, after which the bottle was sealed. The sealed bottle containing the clear solution was tumbled in a constant temperature bath for 20 hours at 55°C resulting in a viscous cloudy white solution.
- mercaptofunctional dimethyl siloxane with 4-5 mole mercapto functionality commercially available as KF-2001 from Shin-Etsu
- MEK methyl ethyl ketone
- a waterborne solution was prepared by filling a gallon jar with 860 grams deionized (DI) water and 9 grams NBLjOH. Next, 537 grams ofthe solvent borne solution (40.0 % solids) was added to the solution in the gallon jar. The resulting solution was placed on a shaker and shaken for one-half hour in order to complete the neutralization. The MEK was then stripped from the resulting viscous solution on a rotary evaporator at 40°C using an aspirator vacuum to yield 19.0 % solids aqueous solution. An additional amount of DI water was added to obtain 15.0 % solids solution. The ingredients utilized in forming a solvent borne solution and water borne solution and the amount ofthe ingredients utilized are reported in Tables 1 and 2 respectively. The ingredients ofthe release coating, the weight percentage ofthe ingredients and the test results are reported in Table 3.
- Example 2-20 The copolymers of Examples 2-20 were prepared in accordance with the procedure outlined in Example 1.
- the ingredients utilized in forming a solvent borne solution and water borne solution and the amount ofthe ingredients utilized are reported in Tables 1 and 2 respectively.
- the ingredients ofthe release coating, the weight percentage ofthe ingredients and the test results are reported in Table 3.
- the polymer is the reaction product of KF2001, MA and AA and/or MAA or MMA Table 3
- Example 21 The composition of Example 21 was prepared in the following manner:
- a solvent borne sample was prepared by charging a 4 ounce glass bottle with 4 grams of 15K silicone macromer (SiMac), the preparation of which is described in U.S. Patent No. 7,728,571, 16 grams ethyl methacrylate (EMA), 30 grams methyl ethyl ketone (MEK) and 0.06 g 2-2'-azobisbutyronitrile (AIBN).
- SiMac 15K silicone macromer
- EMA ethyl methacrylate
- MEK methyl ethyl ketone
- AIBN 0.06 g 2-2'-azobisbutyronitrile
- the sample was then diluted to 10% solids for coating. 40 grams of 40% solids polymer solution, 96 grams of toluene and 24 grams of isopropanol (TPA) were added to a 16 ounce wide mouth jar. The mixture was then shaken to form a homogenous mixture.
- the ingredients utilized in forming a solvent borne solution and the amount ofthe ingredients utilized are reported in Tables 4 and 5 respectively.
- the ingredients ofthe release coating, the weight percentage ofthe ingredients and the test results are reported in Table 6.
- Examples 22-27 The copolymers of Examples 22-27 were prepared in accordance with the procedure outlined in Example 21. The ingredients utilized in forming a solvent borne solution and the amount ofthe ingredients utilized are reported in Tables 4 and 5 respectively.
- the polymer is the reaction product ofthe components listed in Table 5 for each example.
- Example 28 A sheet assembly particularly adapted to be printed on both sides in the types of printers described above was made which had the structure illustrated in Figure 1 except that four instead of two layers 16 of pressure sensitive adhesive were placed in spaced relationship on each sheet 12 and 13.
- the sheets 12 and 13 were each 20 pound bond paper and were each about eight and one half by 11 inches in size, with the sheet 13 being slightly longer so that it projected about 0.1 inch past the edge 37.
- the layers 16 of pressure sensitive adhesive were microsphere structured copolymer adhesive described in U.S. Patent 3,691,140 (Silver) dispersed in n-heptane at 8 percent solids.
- the layers of release coating 40 were crosslinked Syl Off 7676 coated at 20 percent solids in 2-butanone.
- the paper was first primed with a vinyl solution containing zinc oxide.
- the release coating 41 was a polymer described in U.S.S.N. 08/040876 Example 1, except the composition was KF2001/MA MAA/MMA 25/50/20/5 dispersed in 2-butanone (Example 20) to 1.5 percent solids.
- the adhesive was coated to provide an adhesion comparable to Post-it® notes (i.e., approximated 0.6 N/dm adhesion to glass) in 0.75-inch (1.9 cm) wide stripes 16 extending the full width ofthe sheets 12 and 13.
- the opposing strip of release coating 40 was coated with a gravure cylinder to provide 1.25-inch (3.2 cm.) wide stripes extending the full width ofthe sheets 12 and 13.
- the materials were coated on a wide web and subsequently converted and folded to form the sheet assemblies 10.
- the initial release ofthe sheet was 166 g/in.
- the sheets were printed using ink jet, a xerographic, and offset printers.
- the test pattern was a solid block of black ink or toner.
- the ink jet printer was an HP 1200C color ink jet printer commercially available from Hewlett-Packard, Palo
- the xerographic printer was a Lanier 6540 copier commercially available from Lanier Worldwide, Inc., Atlanta, GA.
- the percent of inidicia receptivity were as follows: HP 1200 C 100 percent Lanier 6540 92 percent
- the coating ofthe present invention significantly decreases the attendant problems associated with indicia when printed and subsequently used as a stack of pressure-sensitive notes.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU66807/96A AU6680796A (en) | 1995-09-08 | 1996-07-26 | Articles coated with electrophotographic toner receptive release coatings |
EP96926778A EP0848737A1 (en) | 1995-09-08 | 1996-07-26 | Articles coated with electrophotographic toner receptive release coatings |
JP9511184A JP2000500164A (en) | 1995-09-08 | 1996-07-26 | Articles coated with toner-accepting release coating for electrophotography |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US52539895A | 1995-09-08 | 1995-09-08 | |
US08/525,398 | 1995-09-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997009388A1 true WO1997009388A1 (en) | 1997-03-13 |
Family
ID=24093090
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1996/012286 WO1997009388A1 (en) | 1995-09-08 | 1996-07-26 | Articles coated with electrophotographic toner receptive release coatings |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0848737A1 (en) |
JP (1) | JP2000500164A (en) |
KR (1) | KR19990044418A (en) |
AU (1) | AU6680796A (en) |
CA (1) | CA2229165A1 (en) |
WO (1) | WO1997009388A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6074747A (en) * | 1995-06-06 | 2000-06-13 | Avery Dennison Corporation | Ink-imprintable release coatings, and pressure sensitive adhesive constructions |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109627414B (en) * | 2018-12-11 | 2021-08-24 | 长春安旨科技有限公司 | High-temperature post-curing polyurethane composite material |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0371633A2 (en) * | 1988-11-30 | 1990-06-06 | Minnesota Mining And Manufacturing Company | Indicia-receptive low adhesion backsize |
EP0421588A2 (en) * | 1989-08-14 | 1991-04-10 | Minnesota Mining And Manufacturing Company | A method of making vinyl-silicone copolymers using mercapto functional silicone chain-transfer agents and release coatings made therewith |
WO1993023009A1 (en) * | 1992-05-12 | 1993-11-25 | Minnesota Mining And Manufacturing Company | Polymers in cosmetics and personal care products |
WO1994019420A1 (en) * | 1993-02-16 | 1994-09-01 | Minnesota Mining And Manufacturing Company | System comprising release agent and high peel adhesion repositionable adhesive |
EP0618509A1 (en) * | 1993-03-31 | 1994-10-05 | Minnesota Mining And Manufacturing Company | Electrophotographic toner receptive release coatings |
WO1995003776A1 (en) * | 1993-08-03 | 1995-02-09 | Minnesota Mining And Manufacturing Company | Polymers in cosmetics and personal care products |
-
1996
- 1996-07-26 KR KR1019980701662A patent/KR19990044418A/en not_active Application Discontinuation
- 1996-07-26 JP JP9511184A patent/JP2000500164A/en not_active Ceased
- 1996-07-26 EP EP96926778A patent/EP0848737A1/en not_active Withdrawn
- 1996-07-26 WO PCT/US1996/012286 patent/WO1997009388A1/en not_active Application Discontinuation
- 1996-07-26 CA CA002229165A patent/CA2229165A1/en not_active Abandoned
- 1996-07-26 AU AU66807/96A patent/AU6680796A/en not_active Abandoned
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0371633A2 (en) * | 1988-11-30 | 1990-06-06 | Minnesota Mining And Manufacturing Company | Indicia-receptive low adhesion backsize |
EP0421588A2 (en) * | 1989-08-14 | 1991-04-10 | Minnesota Mining And Manufacturing Company | A method of making vinyl-silicone copolymers using mercapto functional silicone chain-transfer agents and release coatings made therewith |
WO1993023009A1 (en) * | 1992-05-12 | 1993-11-25 | Minnesota Mining And Manufacturing Company | Polymers in cosmetics and personal care products |
WO1994019420A1 (en) * | 1993-02-16 | 1994-09-01 | Minnesota Mining And Manufacturing Company | System comprising release agent and high peel adhesion repositionable adhesive |
EP0618509A1 (en) * | 1993-03-31 | 1994-10-05 | Minnesota Mining And Manufacturing Company | Electrophotographic toner receptive release coatings |
WO1995003776A1 (en) * | 1993-08-03 | 1995-02-09 | Minnesota Mining And Manufacturing Company | Polymers in cosmetics and personal care products |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6074747A (en) * | 1995-06-06 | 2000-06-13 | Avery Dennison Corporation | Ink-imprintable release coatings, and pressure sensitive adhesive constructions |
US6432190B1 (en) | 1995-06-06 | 2002-08-13 | Avery Dennison Corporation | Ink-imprintable release coatings, and pressure sensitive adhesive constructions |
US6780231B2 (en) | 1995-06-06 | 2004-08-24 | Avery Dennison Corporation | Ink-imprintable release coatings, and pressure sensitive adhesive constructions |
Also Published As
Publication number | Publication date |
---|---|
JP2000500164A (en) | 2000-01-11 |
AU6680796A (en) | 1997-03-27 |
KR19990044418A (en) | 1999-06-25 |
CA2229165A1 (en) | 1997-03-13 |
EP0848737A1 (en) | 1998-06-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5154962A (en) | Indicia-receptive low adhesion backsize | |
US5744207A (en) | Articles coated with electrophotographic toner receptive release coatings | |
US6482510B1 (en) | Digital printable and releasable form construction and composition useful thereto | |
EP1159652A1 (en) | Image receptor medium containing ethylene vinyl acetate carbon monoxide terpolymer | |
US6406787B1 (en) | Digital printable and releasable form construction and composition useful thereto | |
US4070523A (en) | Printable pressure-sensitive adhesive tapes | |
EP0618509B1 (en) | Electrophotographic toner receptive release coatings | |
US5807624A (en) | Electrostatically charged imaging manifold | |
WO1997009388A1 (en) | Articles coated with electrophotographic toner receptive release coatings | |
CA1339225C (en) | Indicia-receptive low adhesion backsize | |
US5283092A (en) | Imaging manifold | |
MXPA98001706A (en) | Articles coated with dependable coatings capable of accepting organic pigment electrofotograf | |
US5824396A (en) | Digital offset printing media | |
EP0858004B1 (en) | Toner-receptive sheet for digital offset printing | |
KR100260797B1 (en) | Overhead film for electronograph copy and its manufacturing method | |
EP0950537A2 (en) | A transparent recording sheet having an image-receptive coating, an anti-static coating, and a removable opaque anti-static adhesive strip | |
ZA200200854B (en) | Digitally printable releasable coating and form construction using this coating. | |
JPH10104867A (en) | Adhesive sheet | |
JP2003261839A (en) | Pressure-sensitive adhesive paper |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AL AM AT AU AZ BB BG BR BY CA CH CN CZ DE DK EE ES FI GB GE HU IL IS JP KE KG KP KR KZ LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TR TT UA UG UZ VN AM AZ BY KG KZ MD RU TJ TM |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
ENP | Entry into the national phase |
Ref document number: 2229165 Country of ref document: CA Ref country code: CA Ref document number: 2229165 Kind code of ref document: A Format of ref document f/p: F |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1996926778 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1019980701662 Country of ref document: KR |
|
ENP | Entry into the national phase |
Ref country code: JP Ref document number: 1997 511184 Kind code of ref document: A Format of ref document f/p: F |
|
WWP | Wipo information: published in national office |
Ref document number: 1996926778 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 1996926778 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1019980701662 Country of ref document: KR |
|
WWR | Wipo information: refused in national office |
Ref document number: 1019980701662 Country of ref document: KR |