# US 2014/0193619 A1 · Hyperbranched polyesters in printing inks

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- Number: US 2014/0193619 A1
- Document ID: US20140193619A1
- Status: Published application
- Kind: A1
- Application number: 14/009,160
- Filed: 2012-04-13
- Published: 2014-07-10
- Earliest claimed: 2011-04-15
- Assignees: BASF SE
- Inventors: Bernd Bruchmann; Monika Haberecht; Chien Lu Hsu; John Campbell; James W. Taylor
- Web page: https://patentgrep.com/patent/US20140193619A1

## CPC

- C09D 11/104: Polyesters
- C09D 11/02: Printing inks (C09D11/30 takes precedence)
- B32B 15/08: of synthetic resin
- B32B 15/085: comprising polyolefins
- B32B 15/088: comprising polyamides
- B32B 15/09: comprising polyesters
- B32B 15/20: comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)}
- B32B 27/08: of synthetic resin
- B32B 27/20: using fillers, pigments, thixotroping agents
- B32B 27/302: {comprising aromatic vinyl (co)polymers, e.g. styrenic (co)polymers}
- B32B 27/32: comprising polyolefins {(comprising vinyl (co)polymers or acrylic (co)polymers B32B27/30)}
- B32B 27/34: comprising polyamides
- B32B 27/36: comprising polyesters
- B32B 2250/03: 3 layers
- B32B 2255/26: Polymeric coating
- B32B 2307/75: Printability
- C08G 63/12: derived from polycarboxylic acids and polyhydroxy compounds
- C08G 63/123: the acids or hydroxy compounds containing carbocyclic rings
- C08G 63/137: Acids or hydroxy compounds containing cycloaliphatic rings
- C08G 63/16: Dicarboxylic acids and dihydroxy compounds
- C08G 63/18: the acids or hydroxy compounds containing carbocyclic rings
- C08G 63/199: Acids or hydroxy compounds containing cycloaliphatic rings
- C08G 63/20: Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
- C08K 3/013: Fillers, pigments or reinforcing additives
- C08K 3/04: Carbon
- C08K 3/08: Metals
- C08K 3/22: of metals
- C08K 5/0041: {Optical brightening agents, organic pigments}
- C08K 5/23: Azo-compounds
- C08K 5/34: Heterocyclic compounds having nitrogen in the ring
- C08K 2003/2206: {of calcium, strontium or barium}
- C08K 2003/2227: {of aluminium}
- C08K 2003/2241: {Titanium dioxide}
- C08K 2003/2265: {of iron}
- C08L 1/18: Cellulose nitrate {, i.e. nitrocellulose}
- C08L 67/00: Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain (of polyester-amides C08L77/12; of polyester-imides C08L79/08); Compositions of derivatives of such polymers
- C08L 67/03: the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked to aromatic rings
- C09D 11/10: based on artificial resins
- C09D 11/102: containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
- C09D 101/18: Cellulose nitrate
- C09D 167/00: Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain (based on polyester-amides C09D177/12; based on polyester-imides C09D179/08); Coating compositions based on derivatives of such polymers
- C09D 167/03: the dicarboxylic acids and dihydroxy compounds having the carboxyl - and the hydroxy groups directly linked to aromatic rings
- Y10T 428/24802: Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
- Y10T 428/24851: Intermediate layer is discontinuous or differential
- Y10T 428/24876: Intermediate layer contains particulate material [e.g., pigment, etc.]
- Y10T 428/24901: including coloring matter
- Y10T 428/24909: Free metal or mineral containing
- Y10T 428/24917: including metal layer
- Y10T 428/31681: Next to polyester, polyamide or polyimide [e.g., alkyd, glue, or nylon, etc.]
- Y10T 428/31692: Next to addition polymer from unsaturated monomers
- Y10T 428/31725: Of polyamide
- Y10T 428/31736: Next to polyester
- Y10T 428/3175: Next to addition polymer from unsaturated monomer[s]
- Y10T 428/31757: Polymer of monoethylenically unsaturated hydrocarbon
- Y10T 428/31786: Of polyester [e.g., alkyd, etc.]
- Y10T 428/31797: Next to addition polymer from unsaturated monomers
- Y10T 428/31855: Of addition polymer from unsaturated monomers
- Y10T 428/31909: Next to second addition polymer from unsaturated monomers
- Y10T 428/31913: Monoolefin polymer
- Y10T 428/31938: Polymer of monoethylenically unsaturated hydrocarbon
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The invention relates to multilayer materials for producing packaging comprising at least two films and also a layer which is printed with a packaging printing ink, said packaging printing ink comprising a certain hyperbranched polyester containing functional groups. The invention further relates to a packaging printing ink which comprises a certain hyperbranched polyester containing functional groups, and to the use of said printing ink for producing multilayer materials.

## Claims

### Claim 1

A multilayer material comprising:
a first film comprising a polymeric material;
at least one print layer comprising a packaging printing ink;
a second film; wherein:
the packaging printing ink comprises at least a first binder and a second binder
the first binder comprising at least one hyperbranched polyester containing functional groups selected from the group consisting of OH, COOH and COOR groups, wherein R comprises groups having from 1 to 60 carbon atoms and optionally may also contain heteroatoms or further substituents;
the hyperbranched polyester comprises the polymerization product of:
at least one acid selected from the group consisting of phthalic acid, isophthalic acid, terephthalic acid, 1,2-cyclohexane dicarboxylic acid, 1,3-cyclohexane dicarboxylic acid, 1,4-cyclohexane dicarboxylic acid and
methylhexahydrophthalic; and
at least one at least trivalent aliphatic alcohol selected from the group consisting of trimethylolpropane, glycerol and pentaerythritol;
a number average molecular weight of the hyperbranced polyester is at least 300 g/mol and a ratio of weight average molecular weight to number average molecular weight is about 1.2-10;
the ratio of hydroxyl groups to carboxyl groups in the reaction mixture is from 2:1 to 1:2;
the trivalent aliphatic alcohol is essentially free of diol groups;
the second binder is selected from the group consisting of polyvinylbutyral, nitrocellulose, polyamides, polyurethanes, polyvinyl chlorides, polyketones, polycarbonates, polyacrylates and polyacrylate copolymers; and
a weight ratio of the hyperbranched polyester to the total amount of all the binders is at least 50% by weight.

### Claim 2 (depends on 1)

The multilayer material of claim 1, wherein the first film is selected from the group consisting of polyethylene, polypropylene, polystyrene, polyester and polyamide.

### Claim 3 (depends on 1)

The multilayer material of claim 1, wherein the second film is selected from the group consisting of polyethylene, polypropylene, polystyrene, polyester, polyamide and aluminum.

### Claim 4 (depends on 1)

The multilayer material of claim 1, wherein the glass transition temperature of the hyperbranched polyester is from 20 to 60° C.

### Claim 5 (depends on 1)

The multilayer material of claim 1, wherein the at least one acid is 1,2-cyclohexane dicarboxylic acid or 1,2-cyclohexane dicarboxylic acid anhydride.

### Claim 6 (depends on 1)

The multilayer material of claim 1, wherein the trivalent aliphatic alcohol is trimethylolpropane.

### Claim 7 (depends on 1)

The multilayer material of claim 1, wherein the second binder is selected from the group consisting of nitrocellulose and polyurethanes.

### Claim 8 (depends on 1)

The multilayer material of claim 1, wherein the packaging printing ink further comprises as binder nitrocellulose, wherein the weight ratio of hyperbranched polyester to total amount of all binders is less than 100% by weight.

### Claim 9

A printing ink binder comprising a of hyperbranched polyester that is a polymerization product of
an acid selected from the group consisting of phthalic acid, isophthalic acid, terephthalic acid, 1,2-cyclohexane dicarboxylic acid, 1,3-cyclohexane dicarboxylic acid, 1,4-cyclohexane dicarboxylic acid and methylhexahydrophthalic; and
a trivalent aliphatic alcohol selected from the group consisting of trimethylolpropane, glycerol and pentaerythritol; wherein:
the trivalent aliphatic alcohol is essentially free of diol groups;
a number average molecular weight of the hyperbranched polyester is at least 300 g/mol and a ratio of weight average molecular weight to number average molecular weight of the hyperbranched polymer is about 1.1-20; and
a ratio of acid group of the acid to hydroxyl groups of the trivalent aliphatic alcohol is from 2:1 to 1:2.

### Claim 10

A printing ink comprising:
a first binder comprising at least one hyperbranched polyester, the hyperbranched polyester comprising the polymerization product of:
at least one acid selected from the group consisting of phthalic acid, isophthalic acid, terephthalic acid, 1,2-cyclohexane dicarboxylic acid, 1,3-cyclohexane dicarboxylic acid, 1,4-cyclohexane dicarboxylic acid and methylhexahydrophthalic; and
at least one at least trivalent aliphatic alcohol selected from the group consisting of trimethylolpropane, glycerol and pentaerythritol, wherein the trivalent aliphatic alcohol is essentially free of diols; wherein:
a number average molecular weight of the hyperbranched polyester is at least 300 g/mol a ratio of a weight average molecular weight to the number average molecular weight is from about 1.1-20;
a ratio of hydroxyl groups in the trivalent aliphatic alcohol to acid groups of the acid is from 2:1 to 1:2,
a second binder selected from the group consisting of polyvinylbutyral, nitrocellulose, polyamides, polyurethanes, polyvinyl chlorides, polyketones, polycarbonates, polyacrylates and polyacrylate copolymers;
at least one solvent; and
a weight ratio of hyperbranched polyester to a total amount of all the binders is at least 50% by weight.

### Claim 11 (depends on 10)

The printing ink of claim 10 further comprising at least one colorant.

### Claim 12 (depends on 11)

The printing ink of claim 11, wherein the colorant comprises titanium dioxide, iron oxide, an interference pigment, carbon black, a metal powder, an azo pigment, a phthalocyanine pigment, an isoindoline pigment.

### Claim 13 (depends on 11)

The printing in of claim 11, wherein the colorant comprises phthalocyanine blue 15:4, phthalocyanine green 7, green 36, yellow 12, yellow 14, red 57:1, or red 52:1.

### Claim 14 (depends on 10)

The printing ink of claim 10 further comprising an additive selected from the group consisting of calcium carbonate, aluminum oxide hydrate, aluminum silicate, magnesium silicate, a wax, a fatty acid amide, a plasticizer, a dispersing agent, and an adhesion promoter.

### Claim 15 (depends on 15)

The printing ink of claim 15, wherein the additive is present in the ink from 0 wt % to 20 wt %.