AU659148B2 - Adhesive for bonding a plastic film to a paper support to provide a plastic coating, and particularly suitable for bonding plastic film to sheet paper or cardboard - Google Patents
Adhesive for bonding a plastic film to a paper support to provide a plastic coating, and particularly suitable for bonding plastic film to sheet paper or cardboard Download PDFInfo
- Publication number
- AU659148B2 AU659148B2 AU16506/92A AU1650692A AU659148B2 AU 659148 B2 AU659148 B2 AU 659148B2 AU 16506/92 A AU16506/92 A AU 16506/92A AU 1650692 A AU1650692 A AU 1650692A AU 659148 B2 AU659148 B2 AU 659148B2
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- 230000001070 adhesive effect Effects 0.000 title claims description 69
- 239000000853 adhesive Substances 0.000 title claims description 68
- 239000000123 paper Substances 0.000 title claims description 24
- 239000002985 plastic film Substances 0.000 title claims description 21
- 229920006255 plastic film Polymers 0.000 title claims description 21
- 239000006223 plastic coating Substances 0.000 title claims description 14
- 239000011111 cardboard Substances 0.000 title claims description 11
- 239000011087 paperboard Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 claims description 12
- 229920005749 polyurethane resin Polymers 0.000 claims description 12
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 10
- 229920001451 polypropylene glycol Polymers 0.000 claims description 10
- 239000012948 isocyanate Substances 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 7
- 229920002635 polyurethane Polymers 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 4
- 150000003077 polyols Chemical class 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical group CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- -1 polypropylene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004049 embossing Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- 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
-
- 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
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/10—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of paper or cardboard
-
- 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
- C08G18/08—Processes
- C08G18/089—Reaction retarding agents
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6688—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271
-
- 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
- C09J175/08—Polyurethanes from polyethers
-
- 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
- C09J175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
-
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paper (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Adhesive Tapes (AREA)
Description
F OPI DATE 17/11/92 APPLN. ID 16506/92 11 AOJP DATE 1q-/1./92 PCT NUMBER PCT/EP92/00896 11111111111111111111111 AU9216506 INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (51) International Patent Classification 5 (11) International Publication Number: WO 92/18577 CO9J 175/08, 175/12 Al CO8G 18/12, 18/66, B32B 7/12 (43) International Publication Date: 29 October 1992 (29.10.92) (21) International Application Number: (22) International Filing Date: Priority data: MI91A001118 23 April 1 PCT/EP92/00896 22 April 1992 (22.04.92) 1991 (23.04.91) (81) Designated States: AT (European patent), AU, BE (European patent), BR, CA, CH (European patent), DE (European patent), DK (European patent), ES (European patent), FR (European patent), GB (European patent), GR (European patent), IT (European patent), JP, LU (European patent), MC (European patent), NL (European patent), SE (European patent), US.
Published With international search report.
659148 (71) Applicant (for all designated States except US): MORTON INTERNATIONAL S.P.A. [IT/IT]; Via Trieste, 25, 1- 22076 Mozzate (IT).
(72) Inventor; and Inventor/Applicant (for US only) ROSSI, Massimo [IT/IT]; Via Manfredo Fanti, 9, 1-20028 San Vittore Olona (IT).
(74)Agent: ING. BARZANO' ZANARDO MILANO Via Borgonuovo, 10, 1-20121 Milan (IT).
(54)Title: ADHESIVE FOR BONDING A PLASTIC FILM TO A PAPER SUPPORT TO PROVIDE A PLASTIC COAT- ING, AND PARTICULARLY SUITABLE FOR BONDI.'G PLASTIC FILM TO SHEET PAPER OR CARD-
BOARD
(57) Abstract The invention provides an adhesive for bonding a plastic film to a paper support to provide it with plastic coating, and suitable in particular for bonding said plastic film to sheet paper or cardboard, consisting essentially of a 100 solids one component polyurethane resin having a viscosity substantially of between 600 and 3500 Cp at 100 OC.
II
WO 92/18577 PCT/EP92/00896 1 ADHESIVE FOR BONDING A PLASTIC FILM TO A PAPER SUPPORT TO PROVIDE A PLASTIC COATING, AND PARTICULARLY SUITABLE FOR BONDING PLASTIC FILM TO SHEET PAPER OR CARDBOARD It is well known to coat paper or cardboard supports with plastic film, by a plastic-coating process, where paper and cardboard are plastic coated in order to give the sheet a considerable resistance to abrasion, repeated folding and wear, and to upgrade the appearance of print by giving it brilliance and preventing direct contact with the ink.
This process is used in the most diverse fields, from cosmetics in which the highest quality perfume boxes are formed in this way, to jackets for books and records, covers of periodicals for collection and consultation, bags for shops, cardboard covers for childrens books, exercise books and diaries. It is therefore a very widespread process.
In plastic coating, to obtain the aforesaid chracteristics each individual sheet is bonded by gluing to a film, usually of polypropylene and more rarely of cellulose acetate, over which the adhesive dissolved in a solvent has been spread.
The process normally comprises, in succession, spreading the adhesive over the plastic film, evaporating the adhesive solvent, bonding the film to the sheet by the adhesive, and removing the sheet to recompose the pile.
Specifically, the plastic film, wound on a roll, is unwound and passed through metering rollers where it is spread with the desired quantity of adhesive, after wnich it enters a heated tunnel in which the solvent SUBSTITUTE SH ET WO92/18577 PC/EP92/00896 -2contained in the adhesive is completely evaporated. On leaving the tunnel the film is pressed by a calender to the paper or cardboard sheet, which is fed by a feeder.
During this stage a continuous structure is obtained consisting of a number of side-by-side sheets bonded to a plastic film. The procedure can now continue in two different ways, either by winding the structure onto a reel and then cutting it into sheets, or by immediately separating the sheets to then recompose the bank. This latter procedure is most often used. The adhesive must have particular characteristics in order to adapt to the various types of paper and ink, to give the structure the aforestated characteristics and in particular to resist the mechanical stresses to which it is subjected during processing. Basically it must have a very high degree of initial adhesion to prevent the paper and film moving to different extents and causing wrinkles and channels. It must also have no influence on the tonality of the inks, and not result in colour change. In addition it must be ready to undergo in the shortest possible time further operations such as embossing, cartoning, punching and binding.
All these requirements are totally satisfied by polyurethane adhesives in solution in organic solvents prepared specially for the specific sector. They are used by all plastic coacers. The main problem which arises from the use of this type of adhesive is related to the evaporation of the organic solvent during the plastic coating process, the evaporation involving serious consequences for the environment.
SUBSTITUTE SHEET L i .1' ir 3 SMost plastic coating firms are of craftsman type and operate on a jobbing basis: the various graphic firms send the printed sheets in the most varied shapes and quantities to the plastic coater, who then returns the sheets coated, piled and banked to the printer or bookbinder.
Precisely because of their very small size and the modest turnover of each firm, there is no possibility of~ ivestfng-'I tf r-oeco6very or combus-tio n of- the exit solvents.
This is the reason for the effort expended in research L by adhesives producers to find alternative non-pollutant solutions. In an attempt to obviate this problem adhesives of various chemical types in aqueous solution, including polyurethanes, have appeared.
However this type of adhesive is still under development before finding practical application in industry.
A further system involves the use of film comprising a bonding layer of low melting point. The film is bonded to the paper by using hot calenders. This is however a slow process with many limitations.
GB-A-2077741 and EP-A-028092 relate to polyurethane adhesives of the hot-melt type, namely thermoplastic materials which melt upon heating and set to a firm bond on cooling.
US Patent 4710560 relate to polyurethane resins intended for use in abrasion resistance coatings, for which also adhesive properties to the substrate are described.
The object of the present invention is therefore to provide an adhesive suitable for bonding paper to plastic coating film which overcomes the aforesaid problems of the known art.
This adhesive must therefore be of the type which does not require the use of organic solvents, so avoiding all the problems connected with their removal during the application of the adhesive and film to the shett.
As the adhesive of the present invention is
F
i i .o WO 92/18577 PCT/EP92/00896 -4particularly designed for bonding plastic coating film to sheet paper, a particular object of the invention is to provide an adhesive which develops its adhesiveness within a short time and with a high degree of initial adhesiveness, to prevent the paper sheet and film moving relative to each other and so create wrinkling.
A further object of the invention is to provide the final plastic coated product with ideal functional and aesthetic properties. These and further objects which will be apparent from the description are attained according to the present invention by an adhesive for bonding a plastic film to a paper support to provide it with plastic coating, and suitable in particular for bonding said plastic film to sheet paper or cardboard, characterized by consisting essentially of a 100% solids one component polyurethane resin having a viscosity substantially of between 600 and 3500 Cp at 1000C.
The preferred embodiment of the invention relates to bonding a plastic film to paper or cardboard in form of sheets.
Said film can be made from any suitable plastic such as polypropylene, polyester, cellulose acetate, PVC, or others.
The polyurethane resin according to the invention can be prepared by reacting suitable polyols, such as polypropylene glycols, with a trialcohol or a trifunctional aliphatic amine, and isocyanate in excess, in order to achieve a one component polyurethane.
Said trialcohols can be preferably trimethylol propane, SUBSTITUTE SH-EEr
I
WO 92/18577 PCT/EP92/00896 and said amine can be triisopropanolamine.
Said isocyanate can be preferably 4,4'-diphenylmethane diisocyanate or 2,4'-diphenylmethane diisocyanate; 2,4 toluenediisocyanate, or 2,6 toluenediisocyanate, or a mixture of the two isomers in question.
As regards the polyols, these are quite preferably polypropylenglycols, chosen among those having an average molecular weight approximately inside the range 400-4000. In order to select the desired average molecular weight, said polyols can be monomodal or bimodal.
Suitable viscosity modifiers can be added to the reaction mixture in order to control the targeted viscosity, which is essential according to the adhesive of the invention.
In this regard, OH-bearing compounds can be used, such as for example glycols such as 1,4-butandiols, or monoethylene glycol.
A suitable acid modifier can also be added to the reaction mixture, such as benzoyl chloride, or phosphoric acid.
As stated above, in order to obtain a one component polyurethane, a residual amount of isocyanate is necessary at the end of the "eaction.
'i 25 In this regard, a preferred ratio NCO:OH is approximately 2:1.
Some non- limiting examples are given hereinafter to better describe the characteristics and advantages of the invention.
EXAMPLE 1 A polyurethane resin suitable for forming an adhesive SUBSTITUTE
SHEET
WO 92/18577 PCT/EP92/00896 6 according to the invention is prepared from the following initial composition: a) polypropyleneglycol M.W. 2000) 68.874 (OH No.=86.7) b) polypropyleneglycol M.W. 400 68.874 (OH No.=86.7) c) trimethylolpropane 1.275 d) 4,4'-diphenylmethane diisocyanate 29.815 e) benzoyl chloride 0.036 100.000 molecular weight).
Addition and reaction sequence 1) Add the propyleneglycols a) b) while stirring.
Raise the temperature to 500C.
2) Add and dissolve the trimethylolpropane c).
3) When c) has completely dissolved, add the diisocyanate d) and the benzoyl chloride React under stirring at 90-95 0 C for 2 hours. Check the viscosity at 1000C and the residual isocyanate percentage against the values specified below.
4) Discharge to filter.
The polyurethane resin obtained has the following characteristics: Appearance: clear yellow solid: 100 Viscosity in Cp at 1000C: 1000 200) Brookfield 3 x NCO: 4.3 0.15) The viscosity of this resin was measured as a function I of temperature within the temperature range of 40-65oC, which can be considered the useful operating range for i application of the adhesive.
'I SUBSTITUTE SHEET SlI WO 92/18577 PCT/EP92/00896 7 The results are given in Table A below.
TABLE A Viscosity as a function of temperature Temperature Viscosity (Brookfield RVF100) OC Cp 48000 (6 x 33000 (6 x 22500 (6 x 16000 (6 x 60 10250 (6 x 7250 (6 x 100 1200 N.B. The numbers in parentheses to the side of the viscosity values indicate the rotor/rotational speed combination used for the measurement.
EXAMPLE 2 A polyurethane resin suitable for forming an adhesive according to the invention is prepared from the following initial composition: a) polypropyleneglycol M.W. 2000 57.88 b) polypropyleneglycol M.W. 400 10.13 c) trimethylolpropane 1.25 d) 4,4'-diphenylmethane diisocyanate 29.40 e) benzoyl chloride 0.03 f) dipropylene glycol 1.31 100.00 molecular weight) Addition and reaction sequence 1) Add the propyleneglycols a) b) while stirring.
Raise the temperature to 2) Add and dissolve the trimethylolpropane c).
SUBSTITUTE SHEET -I -II- I ii ii P~/E WO 92/18577 P92/00896
:I
8 3) When c) has completely dissolved, add the diisocyanate d) and the benzoyl chloride React under stirring at 90 0 C for 2 hours. Check the residual isocyanate percentage.
3b) Add the dipropylene glycol f) and react under stirring at 90 0 C for 1 hour. Check the viscosity at 100 0 C and the residual isocyanate percentage against the values specified below.
4) Discharge to filter.
The polyurethane resin obtained has the following characteristics: Appearance: clear yellow solid: 100 Viscosity in Cp at 100 0 C: 2400 200) Brookfield 3 x NCO: 3.2 (t 0.15) The viscosity of this resin was measured as a function of temperature within the temperature range of 40-650C, which can be considered the useful operating range for application of the adhesive.
The results are given in Table A' below.
TABLE A' Viscosity as a function of temperature Temperature Viscosity (Brookfield RVF100)
I
OC
Cp 190000 (6 x 125000 (6 x 82000 (6 x 52000 (6 x 36000 (6 x 23000 (6 x
I
4--rr SUBSTITUTE
SHEET
WO 92/18577 PCT/EP92/00896 -9- 100 2400 N.B. The numbers in parentheses to the side of the viscosity values indicate the rotor/rotational speed combination used for the measurement.
EXAMPLE 3 A polyurethane resin according to the invention is prepared from the following initial composition: a) polypropylenglycol M.W. 2000 43.1005 (OH No.=120.3) b) polypropylenglycol M.W. 400 1 9 8 1 8 No=123) c) Triisopropanolamine 2.295 d) 4,4'-diphenylmethane diisocyanate 34.757 e) benzoyl chloride 0.030 100.000 Addition and reaction sequence 1) React while stirring a) at 450C.
2) Add previously dissolved and mix.
3) When c) is dissolved, add Temperature should be not higher than 800C, check the NCO content, which should be NCO=4.51, and viscosity at 1000C. When viscosity and NCO content are as planned, add and mix e).
4) Discharge to filter.
The adhesive of Example 1 of the invention was used for plastic-coating paper sheets with a polypropylene film (thickness 12 microns).
The object of the test is to determine an important property of the coated sheet, ie its brightness, following bonding with said adhesive, as a function of the quantity of adhesive spread, ie the coating weight 2 (g/m 2 expressed as the grams of adhesive spread per SUBSTITUTE SHEET WO 92/18577 PCT/EP92/00896 10 square metre of sheet surface.
During the bonding, a silicone-coated paper sheet of adequate size is interposed between the two substrates to be joined, taking care to place the silicone coated side of the paper on the substrate with the adhesive.
2 After calendering, a square of 100 cm is cut from the bonded zone containing the silicone-coated paper.
The adhesive -coated substrate and the silicone- coated paper are separated from the rest and weighed on an analytical balance. The adhesive is washed with ihe chosen solvent and the substrate (clean) and silicone-coated paper are re-weighed.
Expression of result: g/m3 (A B) x 100 where: A weight of substrate adhesive silicone-coated paper (before washing) B weight of substrate silicone-coated paper (after washing).
In this test the adhesive of the example of the invention is compared with a polyurethane adhesive of known type dissolved in solvent.
The results obtained are summarized in Tal'le B below.
Two different tests (A and B) at different temperatures were conducted on the adhesive of the invention.
i 25 TABLE B Descriotion of adhesives ADCOTE B16685: Solvent-free adhesive of the above example. NV 100 Viscosity 1100 Cp at 1000C (Brookfield 3x50) NCG 4,2 ADCOTE C2163: Adhesive dissolved in solvent, used for SUBSTITUTE
SHEET
din J. ent A rn Re istered Patent Attorney 2 March 1995 WO 92/18577 PCI/EP92/00896 11 comparison. NV 26 Viscosity 50 Cp at 25 0 C (Brookfield 1x100) NCO 0.6 Comparative machine tests 2 ADCOTE VISCOSITY ADHESIVE CALENDER g/m BRIGHTNESS B16685 cp TEMPERATURE(OC)TEMPERATURE(OC)" 20 0 C 60 0
C
TEST(A) 11750 54/55 60 4.3 65 TEST(B) 4550 68 69/70 2.0 60
ADCOTE
C2163(known)50 25 60 5.0 60 From the results of Table B, it can be generally noted that analogous brightness effects are obtained with the two compared adhesives but using a lower coating weight of the adhesive of the invention. In particular, it can be seen that for an adhesive temperature of around 54/550C (Test a brightness at 20 0 C is obtained for the adhesive of the invention which is in fact better than for the comparison adhesive (again using less adhesive of the invention). At a higher adhesive application temperature (Test B, 680C), the same brightness effect as the comparison adhesive is obtained using only 2 g/m 2 of the adhesive of the invention against 5 mg/m 2 of the comparison adhesive.
The test therefore demonstrates that in addition to the basic advantages of the invention as initially stated, and which are discussed hereinafter, the important property of brightness of the plastic-coated sheet is obtainable in the case of the invention with a decidedly lower amount of adhesive.
The tests also showed that all the initially stated basic advantages of the invention are attained, the SUBSTITUTE SHEET
F,
-7 W92/18577 PCT/EP92/00896 WO 92/18577 12 advantages obtainable with the adhesive of the invention are in particular the elimination of atmospheric and environmental pollution because of the absence of any solvent; energy saving in that no drying tunnel is required; no risk of flammability due to solvents; no problem of disposal of special toxic or harmful refuse; paper-film bonding rate much higher than that of known adhesives (3-4 times higher) and in any event dependent solely on feed capacity of the feeder; to obtain -he same aesthetic and functional characteristics it is sufficient to apply an adhesive quantity 2-3 times less than the quantity currently necessary using known adhesives; because of the small adhesive quantity the appearance of the plastic-coated product is much more planar; when cross-linking is complete the degree of adhesion obtained is higher. In addition, according to the invention, the sheets can be separated and piled after only one hour following bonding. Moreover, they can be immediately fed to subsequent processing, such as embossing, cartoning or binding, this representing a considerable advantage.
iSUBSTITUTE
SHEET
ii- SUBSTTUE SHEET
Claims (4)
13- CLAIMS 1. A method for plastic coating a paper support by bonding a plastic film on it by an adhesive, particularly suitable for bonding said plastic film to sheet paper or cardboard, characterized by the fact of interposing between said paper support and plastic film an adhesive essentially consisting of a 100% solids one component polyurethane resin having a viscosity substantially between 600 and 3500 Cp at 100 0 C. 2. A method according to claim 1, characterized by the fact that said polyurethan; resin is the product of a reaction of a polyol, such as polypropyleneglycol having an average molecular weight inside the range 400 4000, with a trialcohol or a trifunctional aliphatic amine, and isocyanate in excess. 3. A method according to claim 2, characterized by the fact that said trialcohol is trimethylol propane. 4. A method according to claim 2, characterized by the fact that said amine is triisopropanol amine. 5. A method according to claim 2, characterized by the fact that said isocyanate can be selected among 4,4'-diphenylmethane diisocyanate; 2,4'-diphenylmethane diisocyanate; 2,4 tolyenediisocyanate; 2,6 toluene- diisocyanate; a mixture of the isomers in question. 6. A method according to claim 2, characterized by the fact that said reaction is carried out in the presence of a viscosity modifier. 7. An adhesive for bonding a plastic film to a paper support to provide it with plastic coating, and suitable in particular for bonding said plastic film to SUBSTITUTE SHEET I, i r. WO 92/18577 PCT/EP92/00896 14 sheet paper or cardboard, characterized by consisting essentially of a 100% solids one component polyurethane resin having a viscosity substantially of between 600 and 3500 Cp at 100 0 C. 8. An adhesive as claimed in claim 7 characterized by being prepared from the following reaction mixture a) polypropyleneglycol M.W. 2000)
68.874 (OH No.=86.7) b) polypropyleneglycol M.W. 400 68874 (OH =86.7) c) trimethylolpropane 1.275 d) 4,4'-diphenylmethane diisocyanate 29.815 e) benzoyl chloride 0.036
100.000 average molecular weight). 9. An adhesive as claimed in claim 7, characterized by being prepared from the following reaction mixture: a) polypropyleneglycol M.W. 2000 57.88 b) polypropyleneglycol M.W. 400 10.13 c) trimethylolpropane 1.25 d) 4,4'-diphenylmethane diisocyanate 29.40 e) benzoyl chloride 0.03 f) dipropylene glycol 1.31 100.00 average molecular weight). An adhesive as claimed in claim 7 characterized by containing an isocyanate percentage of between 4.15 and 4.35. 11. An adhesive as claimed in claim 7, characterized by being prepared from the following reaction mixture: Sa) polypropylenglycol M.W. 2000 43.100 SUBSTITUTE SHEET 15 b) polypropylenglycol M.W. 400 c) Triisoprooanolamine d) 4,41 -diphenylmethane 19.818 (OH No.=120.3) 2.295 d-iisocyanate 34.757 e) benzoyl chloride 0.030 100.000 and having a NCO content of around 4. 51. 12 mabsi% -as 4 claime in -I nim '7 possessi ng th-e-folTowing vf-stbosity varaih.j'as-d-f-dnt 6n--- of temperature: Temperature Viscosity (Brookfield VF100) in centiooise 48000 33000 50 2250 16 00 0250 7250 100 1200 13. An adhesive as claimed claim 7 characterized by possessing the following scosity values as a function of temperature: Temperature Viscosity (Brookfield RVF100) in centipoise 40 190000 125000 82000 52000 36000 6 23000 00 2400 StPS7- i- U SH EE T -16- 4. Use of a 100% solids one component polyurethane resin having a viscosity substantially inside the range of 600 and 3500 Cp at 100 0 C as an adhesive for bonding a plastic film on a paper support. 1 S 0-oc-s fovr prrng 1Cn9 -qnliq nn- compnonr tpolyurethane resin having a selected viscosit', t. side the range between 600 and 3500 -r at 100 0 C, characterized by reacting polypr lene glycols with a tr~ifunctional alcohol or me,_adding_a_diocaat and an acid modi~ er, such as benzoyl chloride, and reacting e mixture under stirring at a selected I rtue SHEE CI: INTERNATIONAL SEARCH REPORT International Application No PCT/EP 92/00896 I. CLASSIFICATION OF SUBJECT MATTER (if several classification symbols apply, indicate all)6 According to International Patent Classification (IPC) or to both National Classification and IPC Int.Cl. 5 C09J175/08; C09J175/12; C08G18/12; C08G18/66 B32B7/12 I. FIELDS SEARCHED Minimum Documentation Searched 7 Classification System Classification Symbols Int.Cl. 5 C09J C08G Documentation Searched other than Minimum Documentation to the Extent that such Documents are Included in the Fields Searched' Ill. DOCUMENTS CONSIDERED TO BE RELEVANT 9 Category Citation of Document, 11 with indication, where appropriate, of the relevant passages Relevant to Claim No. 13 X GB,A,2 077 741 (AIRBORNE INDUSTRIES) 23 December 1 1981 see claim 1 see page 1, line 13 line see page 1, line 49 line 51 see page 1, line 69 line 105 X EP,A,O 280 092 (L.F.NOLTEMEYER GMBH) 31 August 1 1988 see claims 1,3 see column 1, line 30 line 38 see column 2, line 21 line 32 A US,A,3 198 692 (D.J.BRIDGEFORD) 3 August 1965 1 see claims 1,31 see examples 8,16,17 Special categories of cited documents :to T" later document published after the international filing date document defining the general state of the hrt which is not or priority date and not in conflict with the application but considered to be of particular relevance cted to understand the principle or theory underlying the Invention earlier document but published on or after the international document of r relevance; the claimed invention whfiling dacited to establish the p ica date of another document of particular relevance; the claimed invention cannot be considered novel or cannot be considered to document which may throw doubts on priority claim(s) or Involve an inventive step which Is cited to establish the publication date of another citation or other special reason (as specified) 'Y document of particular relevance; the claimed invention itio r r i r ii cannot be considered to Involve an Inventive step when the document referring to an oral disclosure, use, exhibition or document is combined with one or more other such docu- other means ments, such combination being obvious to a person skilled P document published prior to the International filing date but in the aut later than the priority date claimed W*A document menbtr of the same patent family IV. CERTIFICATION Date of the Actual Completion of the International Search Date of Mailing of this International Search Report 27 JULY 1992 D892 International Searching Authority Signature of Authorized Officer EUROPEAN PATENT OFFICE VAN PUYMBROECK M. A. Fem PCTISA/Io0 (secnd sae) (Jmary 19s5) i PCT/EP 92/00896 International Application No
111. DOCUMIENTS CONSIDERED TO BE RELEVANT (CONTINUED FROM THE SECOND SHEET) Category 0 1 Citation of Document, with indication, where appropriate, of the relevant passages Relevant to Claim No. FR,A,1 553 295 (HENKEL) 10 January 1969 see abstract,points 1-3 see page 2, right column, paragraph 3 -paragraph 4 see example 1 UIS,A,4 710 560 (CUNG VU) 1 December 1987 see claims 1,3-5 see column 1, line 51 column 2, line see column 2, line 59 column 3, line 33 Psi PCr/LW210L (utr sla) J mwy IWS) ANNEX TO THE INTERNATIONAL SEARCH REPORT ON INTERNATIONAL PATENT APPLICATION No. EP SA 9200896 59234 This annex fists the patent family members relating to the patent documents cited in the above-mentioned internrlonal search report. The members are as contained in the European Patent Office EDP file on The European Patent Office is in no way liable for these particulars which are merely given for the purpose of informaition. 27/07/92 Patent document Publication Patent family Publication cited in search report Iat member(s) date GB-A-2077741 23-12-81 None EP-A-0280092 31-08-88 DE-U- 8702715 09-04-87 DE-A- 3865316 14-11-91 US-A-3198692 None FR-A-1553295 10-01-69 DE-A- 1594118 21-05-70 AT-A- 295004 15-11-71 BE-A- 709928 26-07-68 CH-A- 497523 15-10-70 NL-A- 6717826 29-07-68 US-A- 3490987 20-01-70 US-A-4710560 01-12-87 EP-A- 0263298 13-04-88 JP-A- 61069873 29-03-88 U C h. C 0. For more details ahout this annex see Official Journal of the European Patent Office, No. 12182
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI91A1118 | 1991-04-23 | ||
| ITMI911118A IT1246958B (en) | 1991-04-23 | 1991-04-23 | ADHESIVE TO COUPLE A PLASTIC FILM TO CARRY OUT A PLASTIC SUPPORT FOR PLASTIFICATION, SUITABLE FOR PARTICULARLY COUPLING PLASTIC FILM WITH PAPER OR SHEET CARDBOARD |
| PCT/EP1992/000896 WO1992018577A1 (en) | 1991-04-23 | 1992-04-22 | Adhesive for bonding a plastic film to a paper support to provide a plastic coating, and particularly suitable for bonding plastic film to sheet paper or cardboard |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1650692A AU1650692A (en) | 1992-11-17 |
| AU659148B2 true AU659148B2 (en) | 1995-05-11 |
Family
ID=11359746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU16506/92A Ceased AU659148B2 (en) | 1991-04-23 | 1992-04-22 | Adhesive for bonding a plastic film to a paper support to provide a plastic coating, and particularly suitable for bonding plastic film to sheet paper or cardboard |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0582607A1 (en) |
| JP (1) | JPH06506963A (en) |
| AU (1) | AU659148B2 (en) |
| BR (1) | BR9205933A (en) |
| CA (1) | CA2109115A1 (en) |
| IT (1) | IT1246958B (en) |
| WO (1) | WO1992018577A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1241241B1 (en) * | 2001-03-16 | 2005-11-16 | Toyo Boseki Kabushiki Kaisha | Compounded film |
| EP4238891A1 (en) | 2022-03-02 | 2023-09-06 | Boegli-Gravures S.A. | Tamper-evidence for a product casing |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0280092A2 (en) * | 1987-02-21 | 1988-08-31 | Ludwig Fr. Noltemeyer GmbH | Musical record disc bag open at one side |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3198692A (en) * | 1963-02-26 | 1965-08-03 | Tee Pak Inc | Polyolefin laminate |
| DE1594118B1 (en) * | 1967-01-27 | 1970-05-21 | Henkel & Cie Gmbh | Adhesives based on isocyanate addition products |
| GB2077741A (en) * | 1980-06-12 | 1981-12-23 | Airborne Ind Ltd | Non-flammable polyurethane adhesive |
| US4710560A (en) * | 1986-09-08 | 1987-12-01 | W. R. Grace & Co. | Polyurethane coating composition |
-
1991
- 1991-04-23 IT ITMI911118A patent/IT1246958B/en active IP Right Grant
-
1992
- 1992-04-22 AU AU16506/92A patent/AU659148B2/en not_active Ceased
- 1992-04-22 CA CA002109115A patent/CA2109115A1/en not_active Abandoned
- 1992-04-22 WO PCT/EP1992/000896 patent/WO1992018577A1/en not_active Ceased
- 1992-04-22 EP EP92909168A patent/EP0582607A1/en not_active Withdrawn
- 1992-04-22 JP JP4508493A patent/JPH06506963A/en active Pending
- 1992-04-22 BR BR9205933A patent/BR9205933A/en not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0280092A2 (en) * | 1987-02-21 | 1988-08-31 | Ludwig Fr. Noltemeyer GmbH | Musical record disc bag open at one side |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9205933A (en) | 1994-07-05 |
| AU1650692A (en) | 1992-11-17 |
| IT1246958B (en) | 1994-12-01 |
| JPH06506963A (en) | 1994-08-04 |
| EP0582607A1 (en) | 1994-02-16 |
| ITMI911118A1 (en) | 1992-10-24 |
| ITMI911118A0 (en) | 1991-04-23 |
| CA2109115A1 (en) | 1992-10-24 |
| WO1992018577A1 (en) | 1992-10-29 |
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