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
  • C09J7/00—Adhesives in the form of films or foils
  • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
  • C09J7/22—Plastics; Metallised plastics
  • C09J7/25—Plastics; Metallised plastics based on macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
  • C09J7/255—Polyesters
• • 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
  • C09J7/00—Adhesives in the form of films or foils
  • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
  • C09J7/29—Laminated material
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  • B32B15/00—Layered products comprising a layer of metal
  • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
  • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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  • B32B23/00—Layered products comprising a layer of cellulosic plastic substances, i.e. substances obtained by chemical modification of cellulose, e.g. cellulose ethers, cellulose esters, viscose
  • B32B23/04—Layered products comprising a layer of cellulosic plastic substances, i.e. substances obtained by chemical modification of cellulose, e.g. cellulose ethers, cellulose esters, viscose comprising such cellulosic plastic substance as the main or only constituent of a layer, which is next to another layer of the same or of a different material
  • B32B23/08—Layered products comprising a layer of cellulosic plastic substances, i.e. substances obtained by chemical modification of cellulose, e.g. cellulose ethers, cellulose esters, viscose comprising such cellulosic plastic substance as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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  • B32B27/00—Layered products comprising a layer of synthetic resin
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  • B32B27/08—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 synthetic resin
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  • 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
• • B—PERFORMING OPERATIONS; TRANSPORTING
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  • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
  • B32B27/306—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising vinyl acetate or vinyl alcohol (co)polymers
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  • B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
  • B32B37/10—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the pressing technique, e.g. using action of vacuum or fluid pressure
• • B—PERFORMING OPERATIONS; TRANSPORTING
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  • B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
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  • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
  • B32B7/04—Interconnection of layers
  • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
• • C—CHEMISTRY; METALLURGY
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  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/18—Manufacture of films or sheets
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
  • C08J7/04—Coating
  • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
  • C08K3/013—Fillers, pigments or reinforcing additives
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
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  • C08K5/20—Carboxylic acid amides
• • C—CHEMISTRY; METALLURGY
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  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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  • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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• • 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
• • 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
  • 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
• • 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
  • C09J7/00—Adhesives in the form of films or foils
  • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
• • B—PERFORMING OPERATIONS; TRANSPORTING
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• • B—PERFORMING OPERATIONS; TRANSPORTING
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• • C—CHEMISTRY; METALLURGY
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  • C08J2433/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
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  • C08J2475/04—Polyurethanes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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  • C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Definitions

• the present invention relates to a biodegradable laminating film with the layer structure A/B, the 0.5 to 7 ⁇ m thick layer A containing a polyurethane or acrylate adhesive; and wherein the 5 to 150 ⁇ m thick layer B comprises an aliphatic polyester and/or aliphatic-aromatic polyester, the aliphatic-aromatic polyester being composed as follows: b1-i) 30 to 70 mol %, based on components b1-i and b1-ii, a Ce-Cis-dicarboxylic acid; b1-ii) 30 to 70 mol %, based on components b1-i and b1-ii, of terephthalic acid; b1-iii) 98 to 100 mol %, based on components b1-i and b1-ii, of 1,3-propanediol or 1,4-butanediol; b1-iv) 0 to 2% by weight,
• the invention also relates to the use of the above-mentioned laminating film for coating substrates such as, in particular, paper or cardboard, and to a method for producing a composite film, in which the above-mentioned laminating film is pressed onto a substrate.
• Flexible packaging is used in particular in the food industry. They often consist of composite films bonded together by a suitable adhesive, with at least one of the films bonded together being a polymeric film. There is a high demand for biodegradable composite film packaging that can be disposed of through composting after use.
• WO 2010/034712 describes a method for the extrusion coating of paper with biodegradable polymers. Adhesives are not usually used in this process. The coated papers accessible with the method described in WO 2010/034712 are due to the limited adhesion to the paper, The mechanical properties, the barrier properties and the biodegradation of the paper composite are not suitable for every application.
• WO 2012/013506 describes the use of an aqueous polyurethane dispersion adhesive for producing composite films, some of which are industrially compostable. Degradation in industrial composting plants takes place under high humidity, in the presence of certain microorganisms and at temperatures of around 55°C. The demands on flexible packaging with regard to their biodegradability are constantly increasing, so that home compostability is often required for numerous applications today.
• the composite films described in WO 2012/013506 do not meet this criterion adequately and are also not suitable for all flexible packaging applications with regard to their mechanical properties and barrier properties.
• the aim of the present invention was therefore to provide laminating films which are improved in terms of their biodegradability, are preferably home compostable, have good adhesion to the substrate, preferably to paper, and also meet the other requirements of modern flexible packaging.
• the laminating films described at the outset meet these criteria.
• Layer A can also be referred to as the adhesive layer and creates the bond between layer B and the substrate.
• Layer A has a layer thickness of 0.5 to 7 ⁇ m and contains a polyurethane or acrylate adhesive.
• the adhesive in layer A preferably consists essentially of at least one polyurethane dispersed in water as a polymeric binder and optional additives such as fillers, thickeners, defoamers, etc., as described in detail in WO 2012/013506.
• the essential features of the polyurethane adhesive described in WO 2012/013506, to which express reference is made, are listed below:
• the polymeric binder is preferably present as a dispersion in water or else in a mixture of water and water-soluble organic solvents with boiling points preferably below 150° C. (1 bar). Water is particularly preferred as the only substance Solvent. Water or other solvents are not included in the weight specifications for the composition of the adhesive.
• the polyurethane dispersion adhesive is preferably biodegradable. Biodegradability within the meaning of this application is given, for example, if the ratio of gaseous carbon released in the form of CO2 to the total carbon content of the material used after 20 days is at least 30%, preferably at least 60 or at least 80%, measured according to the ISO standard 14855 (2005).
• the polyurethanes preferably consist predominantly of polyisocyanates, in particular diisocyanates, on the one hand and, as reactants, polyester diols and bifunctional carboxylic acids on the other.
• the polyurethane is preferably made up of at least 40% by weight, particularly preferably at least 60% by weight and very particularly preferably at least 80% by weight, of diisocyanates, polyester diols and bifunctional carboxylic acids.
• the polyurethane can be amorphous or semi-crystalline. If the polyurethane is partially crystalline, the melting point is preferably less than 80.degree.
• the polyurethane preferably contains polyester diols in an amount of more than 10% by weight, more than 50% by weight or at least 80% by weight, based on the polyurethane.
• the polyurethane dispersions from BASF SE sold under the trade name Epotal® are particularly suitable.
• the polyurethane is preferably made up of: a) diisocyanates, b) diols, of which b1) 10 to 100 mol %, based on the total amount of the diols (b), are polyester diols and have a molecular weight of 500 to 5000 g/mol , b2) 0 to 90 mol%, based on the total amount of the diols (b), have a molecular weight of 60 to 500 g / mol, c) at least one bifunctional carboxylic acid selected from dihydroxycarboxylic acids and diaminocarboxylic acids, d) optionally further, from the monomers (a) to (c) various polyvalent compounds having reactive groups which are alcoholic hydroxyl groups, primary or secondary amino groups or isocyanate groups and e) optionally other than the monomers (a) to (d), monovalent compounds having a reactive group which is an alcoholic hydroxyl group, a primary or secondary amino group or an isocyanate group
• aqueous polyurethane dispersion adhesives of PCT/EP2021/054570 are suitable for the production of composite films that are biodegradable under home compost conditions (25 ⁇ 5°C), with at least one layer B and a second substrate using the polyurethane dispersion adhesive A being bonded , and wherein at least one of the substrates is a polymeric film that is biodegradable under home compost conditions, and wherein at least 60% by weight of the polyurethane consists of:
• a film made from the polyurethane adhesive, layer B and/or the substrate and/or the composite film is preferably home-compostable.
• polyurethane dispersions from BASF SE sold under the trade name Epotal® Eco are particularly suitable.
• Layer B according to the invention has a layer thickness of 5 to 150 ⁇ m and comprises an aliphatic polyester and/or aliphatic-aromatic polyester, the aliphatic-aromatic polyester being composed as follows: b1-i) 30 to 70 mol %, based on the components b1-i and b1-ii, a Ce-Cis-dicarboxylic acid; b1-ii) 30 to 70 mol %, based on components b1-i and b1-ii, of terephthalic acid; b1-iii) 98 to 100 mol %, based on components b1-i and b1-ii, of 1,3-propanediol or 1,4-butanediol; b1-iv) 0 to 2% by weight, based on components b1-i and b1-iii, of a chain extender and/or branching agent
• Aliphatic polyesters are understood to mean, for example, the polyesters described in more detail in WO 2010/034711, to which express reference is made here.
• the polyesters of WO 2010/034711 are generally built up as follows: ia) 80 to 100 mol %, based on components ia to ib, of succinic acid; ib) 0 to 20 mol%, based on components ia to ib, of one or more C6-C20 dicarboxylic acids; ic) 99 to 102 mol %, preferably 99 to 100 mol %, based on components ia to ib, of 1,3-propanediol or 1,4-butanediol; id) 0 to 1% by weight, based on components ia to ic, of a chain extender or branching agent;
• the polyesters in WO 2010/034711 are preferably synthesized in a direct polycondensation reaction of the individual components.
• the dicarboxylic acid derivatives are reacted directly with the diol in the presence of a transesterification catalyst to give the polycondensate of high molecular weight.
• a copolyester can also be obtained by transesterification of polybutylene succinate (PBS) with C6-C2o-dicarboxylic acids in the presence of diol.
• PBS polybutylene succinate
• Zinc, aluminum and, in particular, titanium catalysts are usually used as catalysts.
• Titanium catalysts such as tetra(isopropyl)orthotitanate and in particular tetraisobutoxytitanate (TBOT) have the advantage over the tin, antimony, cobalt and lead catalysts frequently used in the literature, such as tin dioctanoate, that residual amounts of the catalyst or secondary product of the catalyst remaining in the product are less toxic are. This circumstance is particularly important for biodegradable polyesters, since they are released directly into the environment.
• TBOT tetra(isopropyl)orthotitanate and in particular tetraisobutoxytitanate
• the polyesters mentioned can also be prepared by the processes described in JP 2008-45117 and EP-A 488,617. It has proven advantageous first to convert components a to c to a prepolyester with a VN of 50 to 100 mL/g, preferably 60 to 80 mL/g, and then to react this with a chain extender i-d, for example with diisocyanates or with epoxide-containing polymethacrylates in a chain extension reaction to give a polyester i with a VN of 100 to 450 mL/g, preferably 150 to 300 mL/g.
• the acid component i-a 80 to 100 mol %. based on the acid components a and b, preferably 90 to 99 mol%, and particularly preferably 92 to 98 mol% of succinic acid used.
• Succinic acid can be obtained petrochemically and preferably from renewable raw materials, as described in EPA 2185682, for example.
• EPA 2185682 discloses a biotechnological process for the production of succinic acid and 1,4-butanediol starting from different carbohydrates with microorganisms from the Pasteurellaceae class.
• Acid component i-b is used in 0 to 20 mol%, preferably 1 to 10 mol%, and particularly preferably 2 to 8 mol% based on acid components i-a and i-b.
• C6-C2o-dicarboxylic acids ib are to be understood in particular as meaning adipic acid, suberic acid, azelaic acid, sebacic acid, brassylic acid and/or cis-dicarboxylic acid.
• Suberic acid, azelaic acid, sebacic acid and/or brassylic acid are preferred.
• the acids mentioned above can be obtained from renewable raw materials. For example, sebacic acid is out Castor oil accessible. Such polyesters are characterized by an excellent biological
• the dicarboxylic acids i-a and i-b can be used either as the free acid or in the form of ester-forming derivatives.
• Ester-forming derivatives are in particular the di-Ci to Ce-alkyl esters such as dimethyl, diethyl, di-n-propyl, diisopropyl, di-n-butyl, diisobutyl, di-t-butyl, to name di-n-pentyl, diisopentyl or di-n-hexyl ester.
• Anhydrides of the dicarboxylic acids can also be used.
• the dicarboxylic acids or their ester-forming derivatives can be used individually or as a mixture.
• the diols 1,3-propanediol and 1,4-butanediol can also be obtained from renewable raw materials. Mixtures of the two diols can also be used. Because of the higher melting temperatures and the better crystallization of the copolymer formed, 1,4-butanediol is preferred as the diol.
• the diol (components i-c) is added to the acids (components i-a and i-b) in a ratio of diol to diacids of from 1.0:1 to 2.5:1, and preferably from 1.3:1 to 2.2:1 set. Excess amounts of diol are drawn off during the polymerization, so that an approximately equimolar ratio is established at the end of the polymerization. By approximately equimolar is meant a diacid/diol ratio of 0.98 to 1.00.
• a branching agent i-d and/or chain extender i-d' selected from the group consisting of: a polyfunctional isocyanate, isocyanurate, oxazoline, carboxylic anhydride such as maleic anhydride, epoxide (in particular an epoxide-containing poly(meth)acrylate), an at least trifunctional alcohol or an at least trifunctional carboxylic acid.
• a branching agent i-d and/or chain extender i-d' selected from the group consisting of: a polyfunctional isocyanate, isocyanurate, oxazoline, carboxylic anhydride such as maleic anhydride, epoxide (in particular an epoxide-containing poly(meth)acrylate), an at least trifunctional alcohol or an at least trifunctional carboxylic acid.
• a branching agent i-d and/or chain extender i-d' selected from the group consisting of: a polyfunctional isocyanate, isocyanurate
• bifunctional chain extenders are tolylene-2,4-diisocyanate, tolylene-2,6-diisocyanate, 2,2'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, naphthylene-1,5 -diisocyanate or xylylene diisocyanate, 1, 6-hexamethylene diisocyanate, isophorone diisocyanate or methylene bis (4-isocyanatocyclo-hexane) understood. Isophorone diisocyanate and in particular 1,6-hexamethylene diisocyanate are particularly preferred.
• Aliphatic polyesters mean in particular polyesters such as polybutylene succinate (PBS), polybutylene succinate-co-adipate (PBSA), polybutylene succinate-co-sebacate (PBSSe), polybutylene succinate-co-azelate (PBSAz) or polybutylene succinate-co-brassylate (PBSBr).
• PBS polybutylene succinate
• PBSA polybutylene succinate-co-adipate
• PBSSe polybutylene succinate-co-sebacate
• PBSAz polybutylene succinate-co-azelate
• PBSBr polybutylene succinate-co-brassylate
• the aliphatic polyesters PBS and PBSA are marketed by Mitsubishi under the name BioPBS®. More recent developments are described in WO 2010/034711.
• the polyesters i generally have a number-average molecular weight (Mn) in the range from 5000 to 100000, in particular in the range from 10000 to 75000 g/mol, preferably in the range from 15000 to 50000 g/mol, a weight-average molecular weight (Mw) of 30000 to 300,000, preferably 60,000 to 200,000 g/mol and an Mw/Mn ratio of 1 to 6, preferably 2 to 4.
• the viscosity number is between 30 and 450, preferably from 100 to 400 g/mL (measured in o-dichlorobenzene/phenol (weight ratio 50/50)).
• the melting point is in the range from 85 to 130°C, preferably in the range from 95 to 120°C.
• the MVR range according to DIN EN 1133-1 is in the range from 8 to 50 and in particular 15 to 40 cm 3 /10 min (190° C., 2.16 kg).
• Aliphatic polyesters of layer B also include polyhydroxyalkanoates such as polycaprolactone (PCL), poly-3-hydroxybutyrate (PHB), poly-3-hydroxybutyrate-co-3-hydroxyvalerate (P(3HB)-co-P(3HV)), poly -3-hydroxybutyrate-co-4-hydroxybutyrate (P(3HB)-co-P(4HB)) and poly-3-hydroxybutyrate-co-3-hydroxyhexanoate (P(3HB)-co-P(3HH)) and in particular Polylactic acid (PLA) used.
• PCL polycaprolactone
• PHB poly-3-hydroxybutyrate
• P(3HB)-co-P(4HB) poly-3-hydroxybutyrate-co-4-hydroxybutyrate
• P(3HB)-co-P(3HH) poly-3-hydroxybutyrate-co-3-hydroxyhexanoate
• PLA Polylactic acid
• Polylactic acid b2 with the following profile of properties is preferably used: a melting volume rate (MVR at 190° C. and 2.16 kg according to ISO 1133-1 DE from 0.5 to 100 and in particular from 5 to 50 cm 3 /10 minutes) a melting point below 240° C.; a glass transition point (Tg) greater than 55°C a water content of less than 1000 ppm a residual monomer content (lactide) of less than 0.3% a molecular weight greater than 80,000 daltons.
• MVR melting volume rate
• ISO 1133-1 DE ISO 1133-1 DE from 0.5 to 100 and in particular from 5 to 50 cm 3 /10 minutes
• Tg glass transition point
• Tg glass transition point
• Preferred polylactic acids are crystalline polylactic acid types from NatureWorks such as Ingeo® 6201 D, 6202 D, 6251 D, 3051 D and 3251 D and in particular 4043 D and 4044 D and polylactic acids from Total Corbion such as Luminy® L175 and LX175 Corbion and polylactic acids from Hisun such as Revode® 190 or 110.
• NatureWorks such as Ingeo® 6201 D, 6202 D, 6251 D, 3051 D and 3251 D and in particular 4043 D and 4044 D and polylactic acids from Total Corbion such as Luminy® L175 and LX175 Corbion and polylactic acids from Hisun such as Revode® 190 or 110.
• amorphous types of polylactic acid may be suitable, such as, for example, Ingeo® 4060 D from NatureWorks.
• Aliphatic-aromatic polyesters b1 in layer B are linear, chain-extended and optionally branched and chain-extended polyesters, as described, for example, in WO 96/15173 to 15176 or in WO 98/12242, to which express reference is made. Mixtures of different partially aromatic polyesters are also suitable. interesting recent developments are based on renewable raw materials (see WO 2010/034689). In particular, polyesters b1 mean products such as ecoflex® (BASF SE).
• the preferred polyesters b1 include polyesters which contain as essential components: b1-i) 30 to 70 mol %, preferably 40 to 60 and particularly preferably 50 to 60 mol %, based on components b1-i) and b1- ii) an aliphatic dicarboxylic acid or mixtures thereof, preferably as set out below: adipic acid and in particular azelaic acid, sebacic acid and brassylic acid, b1-ii) 30 to 70 mol%, preferably 40 to 60 and particularly preferably 40 to 50 mol%, based on components b1-i) and b1-ii), an aromatic dicarboxylic acid or mixtures thereof, preferably as set out below: terephthalic acid, b1-iii) 98 to 100 mol %, based on components b1-i) and b1 -ii), 1,4-butanediol and 1,3-propanediol; and b1-iv
• Suitable aliphatic diacids and the corresponding derivatives b1-i are generally those having 6 to 18 carbon atoms, preferably 9 to 14 carbon atoms. They can be either linear or branched. Examples which may be mentioned are: adipic acid, azelaic acid, sebacic acid, brassylic acid and suberic acid (suberic acid).
• the dicarboxylic acids or their ester-forming derivatives can be used individually or as a mixture of two or more of them.
• Adipic acid, azelaic acid, sebacic acid, brassylic acid or their respective ester-forming derivatives or mixtures thereof are preferably used.
• Azelaic or sebacic acid or their respective ester-forming derivatives or mixtures thereof are particularly preferably used.
• polybutylene adipate-co-terephthalate PBAT
• polybutylene adipate-co-azelate terephthalate PBAAzT
• polybutylene adipate-co-sebacate terephthalate PBASeT
• polybutylene azelate-co-terephthalate PBAzT
• polybutylene sebacate-co-terephthalate PBSeT
• polybutylene adipate-co-azelate terephthalate PBAAzT
• polybutylene adipate-co-sebacate terephthalate PBASeT
• polybutylene azelate-co-terephthalate PBAzT
• polybutylene sebacate-co-terephthalate PBSeT
• PBAT polybutylene adipate-co-terephthalate
• PBAzT polybutylene azelate-co-terephthalate
• PBSeT polybutylene sebacate-co-terephthalate
• mixtures of polybutylene adipate-co-terephthalate (PBAT) with polybutylene azelate-co-terephthalate (PBAzT) and polybutylensebacate-co-terephthalate PBSeT
• aromatic dicarboxylic acids or their ester-forming derivatives b1-ii can be used individually or as a mixture of two or more thereof.
• Terephthalic acid or its ester-forming derivatives, such as dimethyl terephthalate, are particularly preferably used.
• the diols b1-iii - 1,4-butanediol and 1,3-propanediol - are available as renewable raw materials. Mixtures of the diols mentioned can also be used.
• 0 to 1% by weight preferably 0.1 to 1.0% by weight and particularly preferably 0.1 to 0.3% by weight, based on the total weight of the polyester, of a branching agent and/or 0 to 1% by weight, preferably 0.1 to 1.0% by weight, based on the total weight of the polyester, of a chain extender (b1-vi) is used.
• a difunctional or polyfunctional isocyanate preferably hexamethylene diisocyanate, is preferably used as the chain extender, and polyols, such as preferably trimethylolpropane, pentaerythritol and, in particular, glycerol, are used as the branching agent.
• the polyesters b1 generally have a number-average molecular weight (Mn) in the range from 5,000 to 100,000, in particular in the range from 10,000 to 75,000 g/mol, preferably in the range from 15,000 to 38,000 g/mol, a weight-average molecular weight (Mw) of 30,000 to 300,000, preferably 60,000 to 200,000 g/mol and an Mw/Mn ratio of 1 to 6, preferably 2 to 4.
• Mn number-average molecular weight
• Mw weight-average molecular weight
• the viscosity number is between 50 and 450, preferably from 80 to 250 g/mL (measured in o-dichlorobenzene/phenol (weight ratio 50/50).
• the melting point is in the range from 85 to 150, preferably in the range from 95 to 140°C .
• the MVR (melting volume rate) according to EN ISO 1133-1 DE (190° C., weight 2.16 kg) of the polyester b1 is generally from 0.5 to 20, preferably from 5 to 15 cm 3 /10 min DIN EN 12634 are generally 0.01 to 1.2 mg KOH/g, preferably 0.01 to 1.0 mg KOH/g and particularly preferably 0.01 to 0.7 mg KOH/g.
• At least one mineral filler b3 selected from the group consisting of: chalk, graphite, gypsum, conductive carbon black, iron oxide , calcium sulfate, dolomite, kaolin, silicon dioxide (quartz), sodium carbonate, calcium carbonate, titanium dioxide, silicate, wollastonite, mica, montmorillonite and talc are used.
• Preferred mineral fillers are silicon dioxide, kaolin and calcium sulphate and particularly preferred are: calcium carbonate and talc.
• a preferred embodiment of layer B contains: b1) 60 to 100% by weight, preferably 60 to 99.95% by weight, of an aliphatic-aromatic polyester selected from the group consisting of: polybutylene adipate-co-terephthalate, polybutylene azelate-co-terephthalate and polybutylene sebacate- co-terephthalate; b2) 0 to 15% by weight, preferably 3 to 12% by weight, of a polyhydroxyalkanoate, preferably a polylactic acid; b3) 0 to 25% by weight, preferably 3 to 20% by weight, of a mineral filler.
• an aliphatic-aromatic polyester selected from the group consisting of: polybutylene adipate-co-terephthalate, polybutylene azelate-co-terephthalate and polybutylene sebacate- co-terephthalate
• b2) 0 to 15% by weight, preferably 3 to 12% by weight, of a polyhydroxyalkanoate, preferably
• Layer B particularly preferably additionally contains b4) 0.05 to 0.3% by weight of a lubricant selected from erucic acid amide and stearic acid amide.
• layer B contains no lubricant or mold release agent. Up to layer thicknesses of 150 ⁇ m, this embodiment has very good compatibility with layer A, so that the adhesion of the laminating film to the substrate, such as paper or cardboard in particular, is very good. This shows that when trying to detach the film from the paper or cardboard, fiber tears occur.
• layer B contains 0.05 to 0.3% by weight, based on the total weight of layer B, of a lubricant or mold release agent such as erucic acid amide or, preferably, stearic acid amide.
• a lubricant or mold release agent such as erucic acid amide or, preferably, stearic acid amide.
• the lubricant or mold release agent in particular in conjunction with antiblocking agents, prevents blocking when the polyester film is unwound, which can be used in a further step for laminating.
• the laminate which has a polyester-containing layer, allows the laminate to be deformed later if necessary.
• This embodiment has very good compatibility with layer A up to layer thicknesses of 50 ⁇ m, in the case of stearic acid amide even up to 80 ⁇ m, so that the adhesion of the laminating film to the substrate such as paper or cardboard in particular is very good. This is shown by the fact that fiber tears occur when trying to remove the film from the paper or cardboard.
• lubricants or mold release agents such as behenic acid amide or erucic acid amide or stearic acid amide are used in concentrations higher than 0.3% by weight in layer B, poor compatibility with layer A is observed.
• layer B contains stearic acid amide, it preferably has a thickness of 5 to 50 ⁇ m, preferably 10 to 50 ⁇ m.
• the layer thickness is preferably in the range from 5 to 80 ⁇ m, more preferably in the range from 5 to 50 ⁇ m, particularly preferably in the range from 10 to 50 ⁇ m.
• the compound according to the invention of components i to v can contain other additives known to those skilled in the art.
• the additives customary in plastics technology such as stabilizers; nucleating agents such as the mineral fillers b3 already mentioned above or also crystalline polylactic acid; release agents such as stearates (particularly calcium stearate); Softeners (plasticizers) such as citric acid esters (particularly acetyl tributyl citrate), glyceric acid esters such as triacetylglycerol or ethylene glycol derivatives, surfactants such as polysorbates, palmitates or laurates; Antistatic, UV absorber; UV stabilizer; Anti-fog agents, pigments or preferably biodegradable dyes Sicoversal® from BASF SE.
• the additives are used in concentrations of 0 to 2% by weight, in particular 0.1 to 2% by weight, based on layer B.
• the layer B according to the invention can contain from 0.1 to 10% by weight of plasticizers.
• a layer structure with an additional barrier layer C has proven to be advantageous here.
• a suitable layer structure is, for example, A/B/C/B, where layers A and B have the meaning given above and layer C is a barrier layer consisting of polyglycolic acid (PGA), ethylene vinyl alcohol (EVOH) or preferably polyvinyl alcohol (PVOH).
• the oxygen barrier layer C usually has a layer thickness of 2 to 10 ⁇ m and preferably consists of polyvinyl alcohol.
• a suitable PVOH is, for example, G-Polymer from Mitsubishi Chemicals, in particular G-Polymer BVE8049. Since the PVOH does not sufficiently adhere to the biopolymer layer B, the barrier layer is preferably composed of the individual layers C7C/C, with layer e representing an adhesion promoter layer.
• the BTR-8002P copolymer from Mitsubishi Chemicals, for example, is suitable as an adhesion promoter.
• the adhesion promoter layer usually has a layer thickness of 2 to 6 ⁇ m. In these cases, the laminating film has, for example, the overall layer structure A/B/C7C/C7B or B'.
• A/B/C/B' Another suitable layer structure is A/B/C/B', where layers A, B and C have the meanings mentioned above and layer B' has a layer thickness of 10 to 100 ⁇ m and in addition to the components mentioned for layer B as a lubricant or mold release agent contains 0.1 to 0.5% by weight, preferably 0.2 to 0.5% by weight, based on the total weight of layer B', of erucic acid amide, stearic acid amide or preferably behenic acid amide.
• the laminating film according to the invention is used for composite film lamination of a substrate selected from the group consisting of biodegradable film, metal foil, metalized film, cellophane or, preferably, paper products.
• paper products includes all types of paper and cardboard.
• Suitable fibers for the production of the paper products mentioned are all types commonly used, eg mechanical pulp, bleached and unbleached cellulose, paper pulp from all annual plants and waste paper (also in the form of broke, either coated or uncoated).
• the foregoing fibers can be used either alone or in any mixture thereof to form the pulps from which the paper products are made.
• the term mechanical pulp includes z. B. groundwood, thermomechanical pulp (TMP), chemithermomechanical pulp (CTMP), Compression groundwood, semi-chemical pulp, high yield chemical pulp and refiner mechanical pulp (RMP).
• TMP thermomechanical pulp
• CMP chemithermomechanical pulp
• RMP refiner mechanical pulp
• sulphate pulps, sulphite pulps and soda pulps are suitable chemical pulps.
• suitable annual plants for the production of paper pulp are rice, wheat, sugar cane and kenaf.
• Amounts of 0.01 to 3% by weight, preferably 0.05 to 1% by weight, of size, based on the solids content of the dry paper substance, are usually added to the cellulose, which vary depending on the desired degree of sizing of the paper to be processed .
• the paper can also contain other substances, e.g. As starch, pigments, dyes, optical brighteners, biocides, paper strength, fixatives, defoamers, retention aids and / or drainage aids.
• the composite films produced preferably have the following structure: i) a paper with a basis weight of 30 to 600 g/m 2 , preferably 40 to 400 g/m 2 , particularly preferably 50 to 150 g/m 2 , ii) the paper according to the invention Laminating film with a total thickness of from 5.5 to 300 ⁇ m, preferably from 10 to 150 ⁇ m, and with particular preference from 15 to 100 ⁇ m.
• a wide variety of materials can be used for the paper layers, e.g. B. white or brown kraftliner, cellulose, waste paper, corrugated cardboard or screenings.
• the overall thickness of the paper-film composite is generally between 31 and 1000 g/m 2 .
• a paper-film composite of 80-500 ⁇ m can preferably be produced by lamination, and a paper-film composite of 50-300 ⁇ m can be produced with particular preference by extrusion coating.
• the production of a composite film from the laminating film according to the invention and the substrate is preferably carried out in several steps: first, preferably i) the surface of layer B is activated by a corona treatment; ii) an aqueous dispersion of a polyurethane adhesive is applied and dried and iii) the resulting laminating film of claims 1 to 7 is pressed with side A onto the substrate by suitable roller pressure.
• a surface treatment of layer B before coating with polymer dispersion A is not absolutely necessary. However, better results can be obtained if the surface of layer B is modified prior to the coating process.
• Conventional surface treatments such as e.g. B. the corona treatment, are used, to increase the adhesion.
• the corona treatment or other surface treatments are carried out to the extent necessary for sufficient wettability with the coating composition.
• a corona treatment with approx. 10 watts per square meter and minute is usually sufficient for this purpose.
• primers or intermediate layers between layer B and adhesive coating A can also be used.
• the composite films and in particular the laminating film can also have other, additional functional layers, e.g. B. barrier layers, printing layers, color layers or lacquer layers or protective layers.
• the position of the functional layers can preferably be on the outside, ie on the side of layer B facing away from the adhesive-coated side.
• the substrate eg paper
• the substrate has protection against mineral oil and other types of oil as well as against grease and moisture
• the laminating film exerts a corresponding barrier effect.
• the food has protection against the mineral oils and minerals present in waste paper, for example, since the laminating film exerts this barrier effect.
• the composite film can be welded to itself as well as to paper, cardboard, cellophane and metal, it enables the production of e.g. B. coffee mugs, beverage cartons or cartons for frozen products.
• the composite film is particularly suitable for the production of paper bags for dry foods, e.g. coffee, tea, soup powder, sauce powder; for liquids, e.g. cosmetics, detergents, beverages; tubing laminates; paper carrier bags, paper laminates and coextrudates for ice cream, confectionery (e.g. chocolate and muesli bars) and paper adhesive tape; paper cups, yoghurt cups; ready meal trays; wrapped cardboard (cans, barrels), wet-strength cardboard for outer packaging (wine bottles, food); Coated cardboard fruit boxes; fast food plate; bracket shells; Beverage cartons and cartons for liquids, such as detergents and cleaning agents, cartons for frozen products, ice cream packaging (e.g. sundaes, wrapping material) e.g. B. sundae, wrapping material for conical ice cream cones); paper labels; flower pots and plant pots.
• liquids e.g. cosmetics, detergents, beverages
• tubing laminates e.g.
• aqueous laminating adhesive preparation (polymer dispersion A) is applied as an intermediate layer.
• the advantage of using the laminating adhesive preparation in the extrusion coating process lies in the possibility of lowering the extrusion temperature. Save the used mild conditions Energy and protect against degradation of the biodegradable or preferably home compostable polymer.
• Dispersion coatings do not require heating prior to application.
• the application technique is comparable to that of hot melt adhesives when it comes to coatings in sheet form.
• the web speeds are very high: up to 3000 m/min.
• Dispersion coating processes can therefore also be carried out online on paper machines.
• layer A in the form of hotmelt, to a certain extent as a special case of the extrusion coating process or the dispersion application process.
• This method is described in Ullmann, TSE Troller-Coating.
• the hot-melt adhesive (hotmelt) is pumped from a storage container that has been preheated to around 150 to 200°C into the nozzle, through which the material is applied to the surface.
• the composite films produced according to the invention are suitable in particular for the production of flexible packaging, in particular for food packaging.
• the invention provides the use of the laminating film described herein for the manufacture of composite films which are biodegradable or, preferably, biodegradable under home compost conditions and wherein the composite film is part of a home compostable flexible package.
• An advantage of the invention is that the laminating film used according to the invention enables a good adhesive connection of different substances such as substrate and layer B to one another, as a result of which the bonded assembly has a high level of strength.
• the composite films produced according to the invention also have good biodegradability and in particular home compostability.
• the characteristic “biodegradable” is fulfilled for a substance or a substance mixture if this substance or the substance mixture has a percentage degree of biological degradation of at least 90% after 180 days according to DIN EN 13432.
• biodegradability results in the polyester (blends) breaking down in a reasonable and detectable amount of time.
• Degradation can be enzymatic, hydrolytically, oxidatively and/or by the action of electromagnetic radiation, for example UV radiation, and are usually predominantly caused by the action of microorganisms such as bacteria, yeasts, fungi and algae.
• Biodegradability can be quantified, for example, by mixing polyester with compost and storing it for a certain period of time. For example, according to DIN EN 13432 (referring to ISO 14855), CO2-free air is allowed to flow through mature compost during composting and this is subjected to a defined temperature program.
• biodegradability is calculated as the ratio of the net CO2 release of the sample (after subtracting the CO2 release from the compost without sample) to the maximum CO2 release of the sample (calculated from the carbon content of the sample) as a percentage degree of biodegradation Are defined.
• Biodegradable polyester (mixtures) usually show significant signs of degradation such as fungal growth, cracking and hole formation after just a few days of composting.
• the present invention preferably provides laminating films or composite films containing these laminating films, which are biodegradable under home compost conditions (25 ⁇ 5° C.).
• Home compost conditions mean that more than 90% by weight of the laminating films or composite films are broken down into CO2 and water within 360 days.
• Home compostability is assessed according to Australian standard AS 5810-2010 or French standard NF T 51-800 or ISO 14855-1 (2012) "Determination of ultimate aerobic biodegradability of plastics under controlled composting conditions - Method by analysis of evolved carbon dioxide”.
• the glass transition temperatures were determined by means of differential scanning calorimetry (ASTM D 3418-08, "Midpoint temperature" of the second heating curve, heating rate 20 K/min).
• Component b1) b1 -1) polybutylene adipate-coterephthalate: ecoflex® F C1200 from BASF SE (MVR at 2.5-
• Component b2) b2-1) polylactic acid (PLA) Ingeo® 4044 D from NatureWorks (MVR 1.5-3.5 cm 3 /10 min (190° C., 2.16 kg))
• the compounds listed in Table 1 were produced on a Coperion MC 40 extruder. Exit temperatures were set at 250°C. The extrudate was then granulated under water. After the granules had been produced, the granules were dried at 60.degree.
• the blown film line consisted of a single-screw extruder with a diameter of 30 mm and a length of 25D, a melt spiral distributor with a diameter of 80 mm and a die gap of 0.8 mm.
• the blow up ratio was typically 3.5 resulting in a lay width of the film tube of approximately 440mm.
• the multilayer films were created by means of coextrusion.
• V in Tables 1 and 2 means comparative example
• the base film B was fixed on the laboratory coating table with the corona-pretreated side facing up and the adhesive to be tested was coated directly onto the film using a doctor blade.
• Adhesive A was dried for 2 minutes with a hot air blower and then the laminating film was applied with a hand roller and in the roller laminating station at 70° C, with a roller speed of 5 m/minute and a laminating pressure of 6.5 bar on paper of different thicknesses of 50 gsm to 130 gsm pressed. Thereafter, the laminate was using cut into strips 15 millimeters wide using a cutting template and subjected to various storage cycles. After storage, the laminate strip was pulled apart on the tensile testing machine and the force required for this was recorded. The test was carried out on a tensile testing machine at an angle of 90 degrees with a pull-off speed of 100 mm/min. The test strip was cut open on one side, one of the now loose ends was clamped in the upper clamp and the other in the lower clamp of the tensile testing machine, and the test was started.
• the rating (+) given in the last column of Table 2 means: fiber tear at a force >0.6 N/15 mm
• the rating (-) given in the last column means: no fiber tear at a force >0.6 N/15 mm
• behenic acid amide b4-3 is used as a mold release agent in a concentration of 0.2 to 0.3% by weight, or stearic acid is used in a concentration of 0.4% by weight, adhesion to the paper is already at a layer thickness of Laminating film of 10 or 17 ⁇ m insufficient.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Health & Medical Sciences (AREA)
• Manufacturing & Machinery (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Fluid Mechanics (AREA)
• Physics & Mathematics (AREA)
• Laminated Bodies (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Polyesters Or Polycarbonates (AREA)
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