NZ764733B2 - Polylactic resin compositions for paperboard coating and paperboard coating processes using the compositions - Google Patents
Polylactic resin compositions for paperboard coating and paperboard coating processes using the compositions Download PDFInfo
- Publication number
- NZ764733B2 NZ764733B2 NZ764733A NZ76473318A NZ764733B2 NZ 764733 B2 NZ764733 B2 NZ 764733B2 NZ 764733 A NZ764733 A NZ 764733A NZ 76473318 A NZ76473318 A NZ 76473318A NZ 764733 B2 NZ764733 B2 NZ 764733B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- polylactide
- mixture
- linear polylactide
- linear
- components
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract 21
- 238000000576 coating method Methods 0.000 title abstract 3
- 239000011087 paperboard Substances 0.000 title abstract 3
- 239000011248 coating agent Substances 0.000 title 1
- 239000011342 resin composition Substances 0.000 title 1
- 229920000747 poly(lactic acid) Polymers 0.000 claims abstract 27
- 239000011347 resin Substances 0.000 claims abstract 21
- 229920005989 resin Polymers 0.000 claims abstract 21
- 238000000034 method Methods 0.000 claims abstract 11
- 125000003700 epoxy group Chemical group 0.000 claims abstract 7
- 229920000642 polymer Polymers 0.000 claims abstract 5
- 229920001169 thermoplastic Polymers 0.000 claims abstract 5
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract 5
- 230000009477 glass transition Effects 0.000 claims abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- 238000000113 differential scanning calorimetry Methods 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 239000004593 Epoxy Substances 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 238000002156 mixing Methods 0.000 claims 2
- 229920001610 polycaprolactone Polymers 0.000 claims 2
- 239000004632 polycaprolactone Substances 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- 229930182843 D-Lactic acid Natural products 0.000 claims 1
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 229940022769 d- lactic acid Drugs 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 229920000728 polyester Polymers 0.000 abstract 4
- 238000001125 extrusion Methods 0.000 abstract 1
- 239000000155 melt Substances 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/26—Processes for applying liquids or other fluent materials performed by applying the liquid or other fluent material from an outlet device in contact with, or almost in contact with, the surface
- B05D1/265—Extrusion coatings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/007—After-treatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/14—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the properties of the layers
- B32B37/24—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the properties of the layers with at least one layer not being coherent before laminating, e.g. made up from granular material sprinkled onto a substrate
- B32B2037/243—Coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2317/00—Animal or vegetable based
- B32B2317/12—Paper, e.g. cardboard
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2367/00—Polyesters, e.g. PET, i.e. polyethylene terephthalate
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/10—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of paper or cardboard
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/14—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the properties of the layers
- B32B37/15—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the properties of the layers with at least one layer being manufactured and immediately laminated before reaching its stable state, e.g. in which a layer is extruded and laminated while in semi-molten state
- B32B37/153—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the properties of the layers with at least one layer being manufactured and immediately laminated before reaching its stable state, e.g. in which a layer is extruded and laminated while in semi-molten state at least one layer is extruded and immediately laminated while in semi-molten state
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/912—Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/06—Biodegradable
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2314/00—Polymer mixtures characterised by way of preparation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions 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; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions 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; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
- C08L33/068—Copolymers with monomers not covered by C08L33/06 containing glycidyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
Abstract
polyester blend is made in a reaction of a linear polylactide resin and a thermoplastic epoxy group-containing polymer. The polyester blend is blended with a polyester having a glass transition temperature below 0C to form a polyester blend that is particular useful for making paperboard coatings in a melt extrusion process.
Claims (10)
1. A method for making a modified polylactide composition, comprising the steps of 5 I. forming a reaction mixture by combining: i) 85 to 99.9 weight percent, based on the combined weight of components i) and ii), of a starting linear polylactide resin or mixture of linear polylactide resins wherein the starting linear polylactide resin or mixture of linear polylactide resins has a relative viscosity of 2 to 4.5 wherein the relative viscosity is the ratio of the viscosity of 10 a 1% wt/vol solution of the polylactide resin in chloroform to that of a chloroform standard, as measured using a capillary viscometer at 30°C, the ratio of L-lactic repeating units to D-lactic acid repeating units in the starting linear polylactide resin or mixture of linear polylactide resins is >8:92 and <92:8 and the starting linear polylactide or mixture of linear polylactide resins contains carboxyl end groups and 15 ii) 15 to 0.1 weight percent, based on the combined weight of components i) and ii), of a thermoplastic epoxy group-containing polymer having an epoxy equivalent weight of 1000 to 6000, an average of at least three epoxy groups per molecule, a melting temperature of 100°C or lower as measured by differential scanning calorimetry according to ASTM D03 and a glass transition temperature of 0°C 20 or lower as measured by differential scanning calorimetry according to ASTM D II. reacting a portion of the carboxyl groups of the starting linear polylactide resin or mixture of linear polylactide resins with a portion of the epoxy groups of the thermoplastic epoxy group-containing polymer to form a composition that includes a 25 reaction product of components i) and ii) and a quantity of unreacted component i) and III. after step II, melt-blending the reaction mixture or composition formed in step II with iii) at least one branched polycaprolactone, wherein the at least one branched polycaprolactone has a glass transition temperature of 0°C or lower as measured by differential scanning calorimetry according to ASTM D03 and 30 constitutes 30 to 60 weight percent of the combined weights of components i), ii) and iii).
2. The method of claim 1 wherein step II is performed by heating the reaction mixture to a temperature of 185°C to 240°C for a period of 30 seconds to 5 minutes under shear at a shear rate of at least 100 s and then cooling the composition formed in step II to a temperature below 185°C.
3. The method of claim 1 or 2 wherein in step I, i) 85 to 98 weight percent, based 5 on the combined weight of components i) and ii), of the starting linear polylactide resin or mixture of linear polylactide resins are combined with 15 to 2 weight percent, based on the combined weight of components i) and ii), of the thermoplastic epoxy group- containing polymer. 10
4. The method of any preceding claim wherein components i) and ii) are provided in amounts to provide 1 to 3 epoxy groups per carboxyl group provided by component i).
5. The method of any preceding claim wherein at least 50% of the end groups 15 of the starting linear polylactide resin or mixture of polylactide resins are carboxyl groups.
6. The method of claim 5 wherein at least 55% of the end groups of the starting linear polylactide resin or mixture of polylactide resins i) are carboxyl groups and at 20 least a portion of the linear polylactide resin molecules have two terminal carboxyl groups and no terminal hydroxyl groups.
7. The method of claim 1, wherein the thermoplastic epoxy group-containing polymer is a copolymer of monomers that include ethylene and at least one of glycidyl 25 acrylate and glycidyl methacrylate.
8. The method of claim 1, wherein the modified polylactide composition contains a) 4 to 56 weight percent of the reaction product of components i) and ii), b) 30 to 60 weight percent of component iii) and c) 12 to 72 weight percent of the starting linear 30 polylactide resin or mixture of linear polylactide resins, based on the combined weights of a), b) and c).
9. The method any of claims 1-10, further comprising the step of blending the modified polylactide composition with at least one additional linear polylactide resin to form a diluted modified polylactide composition. 5
10. A modified polylactide composition made in accordance with the method of claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762594007P | 2017-12-03 | 2017-12-03 | |
| PCT/US2018/063181 WO2019108866A1 (en) | 2017-12-03 | 2018-11-30 | Polylactic resin compositions for paperboard coating and paperboard coating processes using the compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ764733A NZ764733A (en) | 2024-10-25 |
| NZ764733B2 true NZ764733B2 (en) | 2025-01-28 |
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