EP4314186A1 - Wässrige klebstoffzusammensetzung zur flaschenetikettierung mit verbesserter kaltwasserhaftung und ausgezeichneter waschbarkeit - Google Patents
Wässrige klebstoffzusammensetzung zur flaschenetikettierung mit verbesserter kaltwasserhaftung und ausgezeichneter waschbarkeitInfo
- Publication number
- EP4314186A1 EP4314186A1 EP22722081.1A EP22722081A EP4314186A1 EP 4314186 A1 EP4314186 A1 EP 4314186A1 EP 22722081 A EP22722081 A EP 22722081A EP 4314186 A1 EP4314186 A1 EP 4314186A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- adhesive composition
- weight
- aqueous adhesive
- label
- container
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 89
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- 239000002318 adhesion promoter Substances 0.000 claims abstract description 36
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- KHLCTMQBMINUNT-UHFFFAOYSA-N octadecane-1,12-diol Chemical compound CCCCCCC(O)CCCCCCCCCCCO KHLCTMQBMINUNT-UHFFFAOYSA-N 0.000 description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229920006296 quaterpolymer Polymers 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- 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
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/02—Polyamines
-
- 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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/334—Applications of adhesives in processes or use of adhesives in the form of films or foils as a label
Definitions
- the invention features an aqueous adhesive composition including a saponified alkali soluble acrylic copolymer, a polyethylene imine, and a silane adhesion promoter.
- the silane adhesion promoter is a functionalized silane oligomer adhesion promoter.
- the saponified alkali soluble acrylic copolymer comprises ammonia.
- the silane adhesion promoter is selected from the group including an epoxy silane and an amino silane, or even an epoxy functional silane oligomer.
- the aqueous adhesive composition includes from 0.02% by weight to 5% by weight of the silane adhesion promoter.
- the polyethylene imine is an aqueous solution that is multifunctional and cationic.
- the aqueous solution of polyethylene amine has a pH of greater than 8.
- the polyethylene imine is selected from the group consisting of linear, branched and hyper-branched.
- the polyethylene imine when in aqueous solution the polyethylene imine has a molecular weight (Ms) as measured by GPC (Gel Permeation Chromatography ) of from 500 to 1,000,000.
- the aqueous adhesive composition includes from 0,02% by weight to 5% by weight of the polyethylene imine.
- the aqueous adhesive composition further includes a natural polymer.
- the natural polymer is selected from the group consisting of starch, dextrin, rosin, casein and cellulose.
- the aqueous adhesive composition includes from 10% by weight to 99.5% by weight of the saponified alkali soluble acrylic copolymer, from 0.02% by weight to 5% by weight of the polyethylene inline, and from 0.02% by weight to 5% by weight of the silane adhesion promoter.
- the polyethylene imine is an aqueous solution and has a molecular weight (Mw) as measured by GPC (Gel Permeation Chromatography) and reported by the supplier of from 500 g/mol to 2,000,000 g/mol and the functionalized silane oligomer adhesion promoter is an epoxy silane.
- Mw molecular weight
- the invention features a container including a label and the dried aqueous adhesive composition, wherein the dried aqueous adhesive composition is present between the label and the container thereby adhering the label to the container.
- the container is selected from the group consisting of glass and poly ethylene terephthalate.
- the label is a paper label i.e. has a paper backing.
- the container is a beverage container.
- the container is a glass beverage container and the label is paper.
- the glass beverage container comprises coated glass.
- the invention features a container including a label and a dried aqueous adhesive composition including a saponified alkali soluble acrylic copolymer and an aqueous solution of a cationic polymer based on a hyperbranched polyethylene imine, wherein the dried aqueous adhesive composition is present between the label and the container thereby adhering the label to the container.
- the invention features a container including a label and a dried aqueous adhesive composition including a saponified alkali soluble acrylic copolymer, a polyethylene imine, and a functionalized silane oligomer adhesion promoter, wherein the dried aqueous adhesive composition is present between the label and the container thereby adhering the label to the container.
- the polyethylene imine has a molecular weight (Mw) as measured by GPC (Gel Permeation Chromatography) and reported by the supplier of from 100,000 g/mol to 1,000,000 g/mol and the functionalized silane oligomer adhesion promoter is an epoxy silane.
- Mw molecular weight
- glass bottles often used for beverages have been modified to include a coating on the outside of the bottle.
- the coating can serve to protect the bottle, improve the brilliance of the bottle, improve scuffing/sliding of the bottle, or adjust any other property of the glass on the outside of the bottle.
- the coating can make it more difficult for the bottle labeling adhesive to strongly adhere a label to the bottle and further to maintain adhesion of the label to the bottle when the bottle is exposed to cold and/or ice water.
- the bottle labeling adhesive needs to be easily washed off under alkali conditions to enable easy removal of the label prior to reuse or recycling of the bottle.
- Easy removal as used herein corresponds to label carryover of 0.5 to 2% based on the total bottles washed.
- an aqueous adhesive composition comprising an alkali soluble acrylic copolymer, and specific additive/s has an excellence balance of adhesion, ease of removal and stability.
- alkali soluble acrylic copolymer means that the acrylic copolymer may be dissolved, preferably fully dissolved, in an aqueous medium comprising an alkali.
- copolymer refers to a copolymer formed from the copolymerization of at least two different types of monomers. This term includes bipolymers, terpolymers, quaterpolymers, etc. according to the number of used monomer species. This term also includes different types of copolymers, such as alternating copolymers, periodic copolymers, random copolymers, block copolymers, linear copolymers and branched copolymers.
- acrylic copolymer refers to a general term for a copolymer formed from the copolymerization of at least two acrylic monomers, such as (meth)acrylic acids and their esters.
- the term “monomer” refers to any chemical compound that can form a covalent bond with itself, another monomer or another chemical compound in a repetitive manner.
- the invention includes an aqueous adhesive composition comprising a saponified alkali soluble acrylic copolymer, a polyethylene imine, and a silane adhesion promoter.
- the invention further includes an aqueous adhesive composition comprising a saponified alkali soluble acrylic copolymer, a polyethylene imine, and a functionalized oligomer silane adhesion promoter.
- the invention also includes an aqueous adhesive composition comprising a saponified alkali soluble acrylic copolymer, an aqueous solution of cationic polymer based on polyethylene imine and a functionalized silane oligomer adhesion promoter that is an epoxy silane.
- the invention also includes a container including a label and a dried aqueous adhesive composition including a saponified alkali soluble acrylic copolymer, a polyethylene inline, and a functionalized silane oligomer adhesion promoter, wherein the dried aqueous adhesive composition is present between the label and the container thereby adhering the label to the container.
- the polyethylene imine can have a molecular w-eight (Mw) as measured by GPC (Gel Permeation Chromatography) and reported by the supplier of from 100,000 g/inol to 1,000,000 g/mol and the functionalized silane oligomer adhesion promoter is an epoxy silane.
- the invention further includes an aqueous adhesive composition comprising a saponified alkali soluble acrylic copolymer and an aqueous solution of cationic polymer based on polyethylene imine
- the saponified alkali soluble acrylic copolymer, the polyethylene imine and the silane adhesion promoter can make up at least 15% by weight, at least 20% by weight, at least 30% by weight, at least 40% by weight, at least 50% by weight, at least 60% by weight, at least 70% by weight, at least 80% by weight, at least 90% by weight, from 15% by weight to 100% by weight, from 30% by weight to 100% by weight, from 30% by weight to 95% by weight, from 60% by weight to 100% by weight, or even from 80% by weight to 100% by weight of the solid portion of the aqueous adhesive composition.
- the aqueous adhesive composition can be soluble under alkali conditions.
- the aqueous adhesive composition can be soluble in a solution having an alkaline concentration of between 1% by weight and 3 % by weight and at a temperature of from 60°C to 90°C, or even 65°C to 85 °C.
- the aqueous adhesive composition can have a viscosity of from 3,000 cP to 500,000 cP, 3,000 cP to 300,000 cP, from 10,000 cP to 300,000 cP, or even from 30,000 cP to 180,000 cP at 26°C using a Brookfield Viscometer.
- the aqueous adhesive composition can have a solids content (as measured after 2 hours @ 105°C) of from 5% by weight to 80% by weight, 10% by weight to 80% by weight, 5% by weight to 50%, or even from 30% by weight to 50% by weight.
- compositions of the invention are stable and are particularly useful for bonding paper labels (i.e. paper backed labels) to hard to bond containers (e.g. glass or plastic bottles) - where the label needs to remain firmly bonded in cold/ice-water yet be easily removed prior to reuse or recycling of the bottle.
- paper labels i.e. paper backed labels
- hard to bond containers e.g. glass or plastic bottles
- the adhesive composition includes a saponified alkali soluble acrylic copolymer, in particular a fully or partially saponified acrylic copolymer, preferably a fully saponified acrylic copolymer.
- the saponified alkali soluble acrylic copolymer is in solution with water.
- the saponified alkali soluble acrylic copolymer is formed by neutralizing an alkali soluble acrylic copolymer.
- alkali soluble acrylic copolymers that can be used to form the saponified alkali soluble acrylic copolymer in the present invention is not limited to the following examples.
- the alkali soluble acrylic copolymer of the invention may be obtained by selecting one or more features from a single or a separate list of constituents defined below.
- the alkali soluble acrylic copolymer of the invention is obtained from the copolymerization of at least two esters of (meth) acrylic acids.
- the main components of the alkali soluble acrylic copolymer can be alkyl acrylates and alkyl methacrylates.
- the alkali soluble acrylic copolymer can be formed from at least one alkyl (meth)acrylate monomer.
- (meth)acrylate refers either to the acrylate or to the methacrylate or to a mixture of both the acrylate and methacrylate.
- alkyl (meth)acrylate refers either to the alkyl acrylate or to the alkyl methacrylate or to a mixture of both the alkyl acrylate and alkyl methacrylate.
- alkyl includes linear and branched alkyl groups.
- the alkyl group of the alkyl (meth)acrylate monomer can be a linear or branched alkyl group having 1 to 20 carbon atoms.
- Examples of a linear or branched alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a n-propyi group, an isopropyl group, a n-butyi group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyi group, a sec-pentyl group, a 3 -pentyl group, a n-hexy!
- a pentadecyf group a hexadecyl group, a heptadecyl group, an octadecyi (stearyl) group, a nonadecyl group, and an eicosyi group.
- the linear or branched alkyl group having 1 to 20 carbon atoms can be selected from the group consisting of a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-pentyl group, a n- hexyl group, a n-heptyl group, a n-octyl group, a nonyl group, a decy! group, an undecy!
- alkyl (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acryiate, sec-butyl (meth)aerylate, tert-butyl (meth)acrydate, n-pentyl (meth)acrylate, isopentyl (meth)acrylate, neopentyl (meth)acry ' late, tert-pentyl (meth)acrylate, sec-pentyl (meth)acrylate, 3 -pentyl (meth)acrylate, n-hexyl (meth)acrylate, isohexyl (meth)acryiate, n-heptyl (meth)acrylate, n-octyl (me
- the alkyl (meth)acrylate can be selected from the group consisting of methyl (meth)acrylate, ethyl (meth)acryiaie, propyl (meth)acrylate, butyl (meth)acrylate and 2-ethylhexyl (meth)acrylate.
- More than one type of alkyl (meth)acrylate as previously defined can be used to prepare the acrylic copolymer.
- the alkali soluble acrylic copolymer can be formed from a plurality of monomers including at least one alkyl (meth)acrylate monomer as previously defined and at least one another monomer that is able to copolymerize with said alkyl (meth) acrylate.
- Said at least one another monomer that is able to copolymerize with said alkyl (meth)acrylate may be selected from the group consisting of aromatic vinyl compounds of the styrene-type, vinyl acetate, butyl methacrylate, hydroxypropyl methacrylate, lauryl (meth)acrylate, hydroxy alkyl (meth)acrylates such as hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acry!ate and hydroxybutyl (meth)acry!ate, and N-vinyl lactames such as N-vinyl pyrrolidone.
- Said at least one another monomer that is able to copolymerize with said alkyl (meth)acry!ate may comprise some functional groups enhancing the solubility of the alkali soluble acrylic copolymer in water.
- the alkali soluble acrylic copolymer can be formed from at least one alkyl (meth)acrylate monomer as previously defined and at least one further monomer comprising acid functionality, preferably carboxylic acid functionality.
- Said at least one further monomer comprising acid functionality may be selected from the group consisting of monomers comprising carboxylic acid, sulfonic acid and phosphonic acid functionalities.
- monomers comprising carboxylic acid functionality include acrylic acid, methacrylic acid, crotonic acid, fumaric acid, maleic acid and itaconic acid.
- monomers comprising sulfonic acid functionality include vinyl sulfonic acid and 2-acrylamido-2-methy!propanesulfonic acid.
- monomers comprising phosphonic acid functionality include vinyisulfonic acid.
- the alkali soluble acrylic copolymer can be formed in the presence of at least one constituent selected from the group consisting of a carboxylic acid protective colloid such as acrylic acid and methacrylic acid, an anionic surfactant such as phosphate esters, for example ethoxy lated phosphate branched 03 alcohol, dodecylbenzenosulfonate and dioctyl sulfosuccinate, a nonionic surfactant such as fatty alcohol polyglycol ether and PE/PQ block copolymers, and combinations thereof.
- the alkali soluble acrylic copolymer does not contain crosslinking grafted groups.
- the alkali soluble acrylic copolymer can have an acid number ranging from 60 nig KOH/g polymer to 160 mg KOH/g polymer, preferably from 80 mg KOH/g polymer to 130 mg KOH/g polymer.
- the alkali soluble acrylic copolymer can have a solids content (as measured after 2 hours @
- 105°C 105°C of from 20% by weight to 80% by weight, or even from 40% by weight to 60% by weight.
- the alkali soluble acrylic copolymer can have a glass transition temperature (Tg) ranging from - 20°C to 40°C, preferably from -7°C to 40°C.
- the glass transition temperature (Tg) is measured by the classical Differential Scanning Calorimetric (DSC) method.
- DSC Differential Scanning Calorimetric
- Examples of useful commercially available alkali soluble acrylic polymers include PLEXTQL
- the alkali soluble acrylic copolymer of the invention is produced by copolymerization methods well -known in the an.
- the alkali soluble acrylic copolymer of the invention is in the form of an aqueous emulsion or dispersion.
- the term “dispersed” means that said fine particles of the alkali soluble acrylic copolymer are distributed throughout the aqueous medium.
- the alkali soluble acrylic copolymer can be formed by emulsion polymerization.
- the term “emulsion” refers to a stable two-phase system where line particles of the alkali soluble acrylic copolymer are dispersed in the aqueous medium.
- Emulsion polymerization is carried out according to standard procedures.
- the emulsion polymerization is carried out in an aqueous medium in the presence of a surfactant and free-radical initiators. More preferably, the emulsion polymerization is carried out in the monomer droplets emulsified in an aqueous medium.
- the pH of the aqueous emulsion or dispersion can range from about 3 to about 6.
- a saponification step can then be carried out to neutralize the alkali soluble acrylic copolymer of the invention and form the saponified alkali soluble acrylic copolymer
- the saponification step can be carried out using any alkali base, preferably ammonia (M3 ⁇ 4) or amine. Said alkali is added in an amount sufficient to neutralize the acrylic copolymer, i.e. to obtain a neutralized acrylic copolymer.
- alkali base preferably ammonia (M3 ⁇ 4) or amine.
- Said alkali is added in an amount sufficient to neutralize the acrylic copolymer, i.e. to obtain a neutralized acrylic copolymer.
- a solution in particular a transparent, medium to highly viscous solution.
- solution refers to a homogenous mixture where the alkali soluble acrylic copolymer is completely solubilized in the alkali medium.
- the pH of the solution comprising the saponified alkali soluble acrylic copolymer can range from 6 to 10.
- the aqueous saponified alkali soluble acrylic copolymer can be present in the composition at from 10% by weight to 99.5% by weight, from 20% by weight to 99.5% by weight, from 30% by weight to 99.5% by weight, from 50% by weight to 99.5% by weight, or even from 80% by weight to 99.5% by weight of the aqueous adhesive composition
- the aqueous adhesive composition includes a polyethylene imine.
- the polyethylene imine can be selected from the group consisting of a room temperature solid and an aqueous solution.
- the polyethylene imine can be an aqueous solution of a cationic polymer based on polyethylene imine. It can further have a structure selected from the group consisting of linear, branched and hyperbranched.
- the inventors have found that an aqueous solution of a cationic polymer based on polyethylene imine, that is hyperbranched and has a relatively higher cationic charge is preferred.
- the polyethylene imine is an aqueous solution having a pH as reported by the supplier of greater than 8, from 9 to 13, or even from 9 to 12.
- the polyethylene imine can have a structure expressed by the following general formula:
- the polyethylene imine can have a molecular weight (Mw) as measured by GPC (Gel Permeation Chromatography) and reported by the supplier of ⁇ 2,000,000 grams/mole (g/mol) ⁇ 1,500,000 g/mol, ⁇ 1,000,000 g/mol, from 500 g/mol to 2,000,000 g/mol, from 500 g/mol to 1,000,000 g/mol, from 100,000 g/mol to 1,500,000 g/mol, from 500 g/mol to 800,000 g/mol, from 100,000 g/mol to 1,000,000 g/mol, or even from 400,000 to 1,000,000 g/mol.
- Mw molecular weight
- the aqueous solution of polyethylene imine can have a solids content of from 15% by weight to 70% by weight, or even from 20% by weight to 70% by weight (ISO 3251) as reported by the supplier.
- the aqueous adhesive composition can include from 0.02% by weight to 5% by weight, from 0.02% by weight to 3% by weight, from 0.05% to 2.5% of the polyethylene imine, or even from .5% by weight to 3% by weight of the polyethylene imine.
- the aqueous adhesive composition can include a silane adhesion promoter.
- a silane adhesion promoter is a silicon based chemical that includes organic and inorganic groups in the same molecule.
- the silane adhesive promoter is often in a 100% solids form. Silane adhesion promoters can be helpful in increasing the adhesion of the aqueous adhesive composition to substrates such as e.g. glass.
- the silane adhesion promoter is not limited and can include any type of composition useful in promoting the adhesion of the aqueous adhesive composition to substrates such as e.g. glass.
- the silane adhesion promoter can be selected from the group consisting of silane, amino silane, epoxy silane, isocyanurate silane and any other silane.
- the silane adhesion promoter is a functionalized silane oligomer adhesion promoter.
- the functional group can be selected from the group consisting of amine, methoxy, epoxy and isocyanurate.
- the silane adhesion promoter is an epoxy silane oligomer.
- the epoxy silane oligomer also helps to improve adhesion to paper.
- Useful silane adhesion promoters include COATOSIL MP200, an epoxy functional silane oligomer and COATOSIL 2287, a 3-glycidoxypropylmethyldiethoxy silane both available from Momentive Performance Materials Inc (Waterford, NY) and CGOP2QO, an epoxy functional silane oligomer available from Qufu Chenguang Chemical Co., Ltd. (Qufu City, China).
- the aqueous adhesive composition can include from 0.02% by weight to 5% by weight, from 0.02% to 3% by weight, from 0.05% to 2.5% by weight of the silane adhesion promoter.
- the aqueous adhesive composition can include from 0,6% by weight to 5% by weight, or even from 0,6% to 2,5% by weight of the silane adhesion promoter.
- the aqueous adhesive composition can include additional component such as urea, ammonia, surfactants, additional adhesion promoters, anti-foaming agents (i.e. defoamers), anti-fungals, thickening agents, extra water used to dilute/adjust the formula, natural polymers (e.g. starch, dextrin, rosin, casein, cellulose, etc.) or any other material or additive commonly used in aqueous adhesive compositions.
- additional component such as urea, ammonia, surfactants, additional adhesion promoters, anti-foaming agents (i.e. defoamers), anti-fungals, thickening agents, extra water used to dilute/adjust the formula, natural polymers (e.g. starch, dextrin, rosin, casein, cellulose, etc.) or any other material or additive commonly used in aqueous adhesive compositions.
- the aqueous adhesive composition can be used to adhere labels to various items (e.g. containers).
- the invention includes a container including a label and the aqueous adhesive composition of this invention, wherein the aqueous adhesive composition is present between the label and the container thereby adhering the label to the container.
- the aqueous adhesive composition can be applied to the back side of the label.
- the label can then be applied directly to the container, the aqueous adhesive composition gains strength as it dries over time, generally at room temperature to form the dried aqueous adhesive composition.
- the container can include a label and the dried aqueous adhesive composition, wherein the dried aqueous adhesive composition is present between the label and the container thereby adhering the label to the container.
- the aqueous adhesive composition can be applied to the label substrate using any suitable technique including, e.g., intermittent, coating, continuous coating, air knife, trailing blade, spraying, brushing, dipping, doctor blade, roller coating (e.g., smooth roll), gravure coating (e.g., direct gravure, reverse gravure, offset gravure, and rotogravure), engraved roller coating, wheel coating, contacting coating, transfer coating (e.g., multi-roll transfer coating), flexographic coating, and combinations thereof
- any suitable technique including, e.g., intermittent, coating, continuous coating, air knife, trailing blade, spraying, brushing, dipping, doctor blade, roller coating (e.g., smooth roll), gravure coating (e.g., direct gravure, reverse gravure, offset gravure, and rotogravure), engraved roller coating, wheel coating, contacting coating, transfer coating (e.g., multi-roll transfer coating), flexographic coating, and combinations thereof
- the container can be a bottle (e.g. beverage bottle (e.g. beer bottle, soda bottle, wine bottle, milk bottle, etc.), a jar (e.g. for food products), a vial, or any other type of container.
- beverage bottle e.g. beer bottle, soda bottle, wine bottle, milk bottle, etc.
- jar e.g. for food products
- vial e.g. for food products
- the container can be reusable. By reusable, it is meant that the container can be returned, cleaned and reused.
- the container can alternatively be recyclable.
- the label preferably has a paper backing.
- the container can be glass, metal (e.g. aluminum or steel) or plastic (polyethylene terephthalate (PET), high density polyethylene (HOPE), polypropylene, etc. and surface treated versions thereof).
- PET polyethylene terephthalate
- HOPE high density polyethylene
- polypropylene etc. and surface treated versions thereof.
- the container is a beverage container.
- the container is glass and the backing is paper.
- Glass containers can be clear, amber, or any other color. Glass containers can be coated with any number of materials including e.g. metal, monostearate, wax (e.g. polyethylene, etc.), oleic acid, silane, silicon, etc.
- the inventors have discovered that the compositions of this invention work particularly well in labeling containers comprising a coated glass.
- the label can be a spot label i.e. a label that does not extend completely around the container.
- the label can be a wraparound label i.e. a label that completely wraps around the entire container.
- Stability The aqueous adhesive composition sample is observed after mixing and a stability rating assigned to it. very good - adhesive sample is homogenous, and maintains good flow properties as it ages very bad - adhesive sample has separated, settled, gelled or sedimentation is present
- the mirror bonding effect is a measure of how well the adhesive on a label transfers to a glass bottle. If the adhesive transfer is low, the bottle has a high mirror bonding effect, as there is no adhesive on the bottle and it is easy to see through the glass.
- the labels to be tested are stored for 16 to 24 hours at a temperature of 23 +/- 1°C and 50 +/- 5% relative humidity.
- On flat surface e.g. glass plate, apply adhesive with a rod coater at a coat weight of 20-24 g/m 2 .
- Test at least three bottles for each adhesive.
- the test is regarded as positive if the labels adhere to the bottles for minimum 14 days in cool water. The test can be stopped when a positive result is obtained in excess of 21 days.
- the adhesive bonds are ranked according the following. very good - bond stays firmly intact medium - bond is partially intact very bad - bond is completely failed
- the labels were applied to the bottles as described in the Mirror Bonding test method (through step 2), using the same amount of aqueous adhesive composition.
- the labelled bottles were allowed to dry for 24 hours at room temperature. The bottles were then aged for 7 days. The bottles were removed from climate chamber and allowed to sit at room temperature for 24 hours. The bottles were then tested according to the following.
- the reactor is tilled with a soda hydroxide solution at a concentration of 1.5% by weight.
- the soda solution is held at a temperature of 75°C.
- a bottle is attached to an electric stirrer by a stirring shaft equipped with a clamp that holds the bottle in place by clampi ng it between the inside and outside of the bottle.
- the bottle is lowered into soda solution.
- a stopwatch is started and the bottle is set to rotate.
- the rotation speed is set to at 25 rotations per minute in a clock wide direction.
- the amounts listed in tine table are in % by weight if the material in the table is aqueous, it is the % by weight of the aqueous material
- the remaining amount of the composition is made yp of a3 ⁇ 4 aqueous alkali soluble acrylic copolymer saponified with ammonia. So, for example Coml is 100% aqueous alkali soluble acrylic copolymer saponified with ammonia.
- the properties listed for the materials in the table tie. solids, pH, etc ) are as repotted by the supplier.
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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202163164695P | 2021-03-23 | 2021-03-23 | |
| PCT/US2022/071284 WO2022204695A1 (en) | 2021-03-23 | 2022-03-23 | Aqueous adhesive composition for bottle labelling with improved cold water adhesion and excellent washability |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP4314186A1 true EP4314186A1 (de) | 2024-02-07 |
Family
ID=81585268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP22722081.1A Pending EP4314186A1 (de) | 2021-03-23 | 2022-03-23 | Wässrige klebstoffzusammensetzung zur flaschenetikettierung mit verbesserter kaltwasserhaftung und ausgezeichneter waschbarkeit |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP4314186A1 (de) |
| KR (1) | KR20230160258A (de) |
| WO (1) | WO2022204695A1 (de) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999050356A1 (fr) * | 1998-03-31 | 1999-10-07 | Daicel Chemical Industries, Ltd. | Composition de resine thermoplastique, composition a base d'eau, adhesif auto-adhesif, thermosensible et feuille thermosensible |
| TWI521032B (zh) * | 2012-06-28 | 2016-02-11 | 羅門哈斯公司 | 濕性膠 |
| US10801163B2 (en) * | 2016-04-15 | 2020-10-13 | H.B. Fuller Company | Polyacrylic adhesive for use in tissue paper laminating |
-
2022
- 2022-03-23 WO PCT/US2022/071284 patent/WO2022204695A1/en active Application Filing
- 2022-03-23 KR KR1020237031553A patent/KR20230160258A/ko unknown
- 2022-03-23 EP EP22722081.1A patent/EP4314186A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2022204695A1 (en) | 2022-09-29 |
| KR20230160258A (ko) | 2023-11-23 |
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