WO2023187159A1 - Method for coating a paper substrate by using a modified cutin extract - Google Patents

Method for coating a paper substrate by using a modified cutin extract Download PDF

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Publication number
WO2023187159A1
WO2023187159A1 PCT/EP2023/058459 EP2023058459W WO2023187159A1 WO 2023187159 A1 WO2023187159 A1 WO 2023187159A1 EP 2023058459 W EP2023058459 W EP 2023058459W WO 2023187159 A1 WO2023187159 A1 WO 2023187159A1
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WO
WIPO (PCT)
Prior art keywords
cutin
extract
paper substrate
modified
coating
Prior art date
Application number
PCT/EP2023/058459
Other languages
English (en)
French (fr)
Inventor
Andrea Mascaro
Cristina BARCELLONA
Simona Esposito
Giovanni Floridi
Thierry Bossi
Dario Conti
Original Assignee
Lamberti Spa
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Lamberti Spa filed Critical Lamberti Spa
Publication of WO2023187159A1 publication Critical patent/WO2023187159A1/en

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Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/16—Sizing or water-repelling agents
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/02—Material of vegetable origin
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/14—Carboxylic acids; Derivatives thereof
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/10—Coatings without pigments
    • D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
    • D21H19/18—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising waxes
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/10—Coatings without pigments
    • D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
    • D21H19/20—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/10—Coatings without pigments
    • D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
    • D21H19/24—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H19/28—Polyesters

Definitions

  • the present invention relates to a method for coating a paper substrate to provide said paper substrate with improved barrier properties.
  • barrier coating compositions are used for improving barrier properties (such as water and/or oil resistance) of paper substrates.
  • barrier coating compositions are based on film-forming polymers derived from fossil resources.
  • Cutin is a support biopolyester involved in waterproofing the leaves and fruits of higher plants. Cutin is the main component (between 40% and 85 wt%) of the plant cuticle, the continuous and lipidic extracellular membrane that covers the aerial parts of leaves, fruits and non-lignified stems of plant.
  • cutin is a polymeric network of polyhydroxylated Ci6 and Cis fatty acids cross-linked by ester bonds.
  • cutin undergoes depolymerization. Therefore a raw cutin extract is mainly composed of hydroxy fatty acids and fatty esters, as well as their oligomers.
  • It is therefore an object of the present invention a method for coating a paper substrate comprising: i) providing a paper substrate; ii) applying to the paper substrate am aqueous barrier coating composition having a solids content from 10 to 60 wt% (% by weight) and comprising from 20 to 100 wt% of a modified cutin extract, wherein said modified cutin extract is obtained by thermal treatment of a raw cutin extract at a temperature comprised between 40 and 120 °C.
  • modified cutin extract we refer to the modification of a raw cutin extract through a thermal treatment. Without wishing to be bound by any theory, it is believed that the thermal treatment allows the formation of a polyester derived from the hydroxyl fatty acids that are the main components of the raw cutin extract.
  • the method for coating a paper substrate may comprise: i) providing a paper substrate; ii) applying to the paper substrate an aqueous barrier coating composition having a solids content from 10 to 60 wt% (% by weight) and comprising from 50 to 100 wt% of a modified cutin extract, wherein said modified cutin extract is obtained by thermal treatment of a raw cutin extract at a temperature comprised between 60 and 100 °C.
  • the method for coating a paper substrate comprises: i) providing a paper substrate; ii) applying to the paper substrate an aqueous barrier coating composition having a solids content from 10 to 60 wt% (% by weight) and comprising from 50 to 100 wt% of a modified cutin extract, wherein said modified cutin extract is obtained by thermal treatment of a raw cutin extract at a temperature comprised between 80 and 100 °C.
  • the raw cutin extract suitable for preparing the modified cutin extract of the present invention can be obtained by any extraction method known in the art for extracting cutin from plant matter.
  • plant matter refers to any portion of a plant that contains cutin including, for example, fruits (in the botanical sense, fruit peels and juice sacs), leaves, stems, barks, seeds, flowers, or any other portion of the plant.
  • plant matter can include agricultural waste products such as, for example, tomato peels, grape skins, apple peels, pepper peels, lemon peels, lemon leaves, lime peels, lime leaves, orange peels, orange leaves, orange fruit, clementine leaves, clementine fruit, mandarin leaves, mandarin fruit, pea seeds, grapefruit peels, grapefruit leaves, grapefruit seeds, papaya peels, cherry fruits, cranberry skins, grass clippings.
  • agricultural waste products such as, for example, tomato peels, grape skins, apple peels, pepper peels, lemon peels, lemon leaves, lime peels, lime leaves, orange peels, orange leaves, orange fruit, clementine leaves, clementine fruit, mandarin leaves, mandarin fruit, pea seeds, grapefruit peels, grapefruit leaves, grapefruit seeds, papaya peels, cherry fruits, cranberry skins, grass clippings.
  • the raw cutin extract of the present invention is obtained preferably from tomato, more preferably from waste tomato peels.
  • the raw cutin extract obtained from waste tomato peels is a complex mixture of long-chain co-hydroxy acids with typically a 16- or 18-carbon skeleton and their oligomers, whose main component is 10,16- dihydroxyhexadecanoic acid.
  • the raw cutin extract is water-based and typically has a dry content ranging from 30 to 95 wt%, preferably from 50 to 80 wt%.
  • the raw cutin extract typically has a pH ranging from 3 to 6.
  • the raw cutin extract has a Brookfield® viscosity (measured on a 31 wt% aqueous solution, at 25 °C and at pH 9) comprised between 10 and 500 mPa*s, preferably between 50 and 200 mPa*s.
  • the process for preparing the modified cutin extract of the present invention comprises a thermal treatment at a temperature comprised between 40 and 120 °C, preferably between 80°C and 100 °C.
  • the process for preparing the modified cutin extract of the present invention comprises a thermal treatment at a temperature comprised between 60°C. which is the approximate melting temperature of dry raw cutin extract, and 100°C.
  • thermal treatment refers to the application of heat to a raw cutin extract.
  • Heat may be applied by conduction (for example, a heating coil), by convection (for example, heat transfer through a fluid, such as water or air), and/or by radiation (for example, heat transfer using electromagnetic waves).
  • Solvents selected among water, organic solvents or mixtures thereof can be added in the process for preparing the modified cutin extract of the present invention.
  • the solvent which can be added is water.
  • the solvent used in the process may be removed by distillation under reduced pressure.
  • the thermal treatment for preparing the modified cutin extract of the present invention is conducted at atmospheric pressure or under reduced pressure (typically between 0.001 to 0.6 bar). Preferably, the thermal treatment is conducted at atmospheric pressure.
  • the thermal treatment for preparing the modified cutin extract of the present invention may be carried out in the presence of a catalyst.
  • a catalyst include, for example, titanium tetraisopropoxide, dibutyltin oxide, tin octanoate, aluminum isopropoxide, zirconium acetylacetonate, zirconium tetrabutoxide, tin(ll) n-octanoate, tin(l l) 2-ethylhexanoate, tin(ll) laurate, dibutyltin dichloride, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dimaleate, dioctyltin diacetate, antimony triethoxide or boronic acid derivatives, such as pyridineboronic acid.
  • the catalyst is zirconium acetylacetonate.
  • the thermal treatment for preparing the modified cutin extract of the present invention can be carried out under acidic (i.e., at a pH ranging from 2 to 7, preferably from 3 to 7) or alkaline conditions (i.e., at a pH ranging from 7 to 12, preferably from 7 to 11).
  • the thermal treatment is carried out under acidic conditions.
  • the thermal treatment is started immediately, as the raw cutin extract typically already has an acidic pH, ranging from 3 to 6.
  • the obtained modified cutin extract is treated with a base until a pH ranging between 7 and 11 is reached.
  • the base is preferably ammonia, an inorganic base or an amine. More preferably, the base is ammonia.
  • the raw cutin extract is treated with a base until a pH ranging between 7 and 11 is reached.
  • the base is preferably ammonia, an inorganic base or an amine. More preferably, the base is ammonia.
  • the process for preparing the modified cutin extract of the present invention comprises a thermal treatment that may last from 2 to 72 hours.
  • the process for preparing the modified cutin extract of the present invention comprises a thermal treatment that preferably lasts from 2 to 24 hours, more preferably from 3 to 15 hours.
  • the modified cutin extract of the present invention is water-based and typically has a dry content ranging from 10 to 60 wt%, preferably from 20 and 40 wt%, and pH comprised between 6 and 11, preferably between 7 and 10.
  • the modified cutin extract has a Brookfield® viscosity (measured on a 31 wt% aqueous solution, at 25 °C and at pH 9) comprised between 100 and 3000 mPa*s, preferably between 300 and 1500 mPa*s.
  • the aqueous barrier coating composition of the invention can further contain customary additives in the field of paper coating, such as pigments, binders, waxes, thickeners, antiblocking agents, dyes, flow control agents or defoamers.
  • Suitable pigments include, for example, metal salt pigments such as, for example, calcium sulfate, calcium aluminate sulfate, barium sulfate, magnesium carbonate and calcium carbonate.
  • Calcium carbonate may be natural ground calcium carbonate (GCC), precipitated calcium carbonate (PCC), lime or chalk.
  • Further suitable pigments include, for example, silica, alumina, aluminum hydrate, silicates, titanium dioxide, zinc oxide, kaolin, argillaceous earths, talc or silicon dioxide.
  • Suitable binders include both synthetic and natural binders.
  • Suitable synthetic binders include, but are not limited to, (meth)acrylic (co)polymers, ethylene- (meth)acrylic copolymers, styrene-(meth)acrylic copolymers and polyvinyl alcohol.
  • Suitable natural binders include, but are not limited to, carboxymethyl cellulose, starch and starch derivatives.
  • Suitable starch includes natural starches, such as potato, wheat, maize, rice or tapioca starch.
  • Suitable starch derivatives include, but are not limited to, chemically modified starches, such as for example hydroxyethyl starch, hydroxypropyl starch or phosphate starch.
  • Preferred starch and starch derivatives include degraded starch and degraded starch derivatives having a molecular weight Mn of 500 to 30,000 Da, more preferably from 500 to 20,000 Da. Said degraded starches are obtained from the degradation of natural starch or chemically modified starch.
  • Suitable waxes include, but are not limited to, polyethylene, polypropylene, paraffins, amides, waxes of vegetable of origin, carnauba waxes, or mixtures thereof.
  • aqueous barrier coating composition of the invention to the paper substrate can be carried out for example by roller coating, spray coating, curtain coating, blade coating, immersion coating, gravure roll coating, reverse direct gravure coating, rod coating, soft-tip blade coating, jet coating and/or combinations thereof.
  • the raw cutin extracts used in the examples are obtained from waste tomato peels and have a Brookfield® viscosity (measured on a 31 wt% aqueous solution, at 25 °C and at pH 9) of 100 mPa*s.
  • Raw cutin extract (50-80 wt% dry content, pH 3-6) polymerization reaction was carried out under vacuum evaporation (100-300 mbar) in a four-necked roundbottom reactor equipped with a mechanical I KA stirrer, thermometer and fitted with a Dean Stark adapter and a condenser for reflux. The reaction was carried out at 90°C until a very high viscosity product (> 50,000 mPas) was achieved with a dry content up to 99.9%. The polymerization reaction was stopped when the product started climbing the impeller (6 h after whole water evaporation).
  • modified cutin extract was cooled down and an ammonia solution was added until an aqueous solution of modified cutin extract having a 25-35 wt% dry content and pH 7-9 was obtained. Filtration was performed using a 100 pm filter cloth. Brookfield® viscosity (31 wt% aqueous solution, at 25°C and pH 9) of the modified cutin extract: 700 mPa*s.
  • Raw cutin extract (50-80 wt% dry content, pH 3-6) polymerization reaction was carried out under atmospheric pressure in a four-necked round-bottom reactor equipped with a mechanical I KA stirrer, thermometer and a condenser for reflux. The reaction was carried out at 90°C for 10 h.
  • the modified cutin extract was cooled down and an ammonia solution was added until an aqueous solution of modified cutin extract having a 25-35 wt% dry content and pH 7-9 was obtained. Filtration was performed using a 100 pm filter cloth. Brookfield® viscosity (31 wt% aqueous solution, at 25°C and pH 9) of the modified cutin extract: 850 mPa*s.
  • Raw cutin extract (50-80 wt% dry content, pH 3-6) polymerization reaction was carried out under atmospheric pressure in a four-necked round-bottom reactor equipped with a mechanical IKA stirrer, thermometer and a condenser for reflux. Before starting the heating, raw cutin extract was treated with ammonia to reach a pH of 9.5. The reaction was carried out at 90°C for 15 h. The modified cutin extract was cooled down and an aqueous solution of modified cutin extract having a 25-35 wt% dry content and pH 7-9 was obtained. Filtration was performed using a 100 pm filter cloth. Brookfield® viscosity (31 wt% aqueous solution, at 25°C and pH 9) of the modified cutin extract: 450 mPa*s.
  • Raw cutin extract (50-80 wt% dry content, pH 3-6) polymerization reaction was carried out under atmospheric pressure in a four-necked round-bottom reactor equipped with a mechanical I KA stirrer, thermometer and a condenser for reflux. The reaction was carried out at 70°C for 15 h.
  • the modified cutin extract was cooled down and an ammonia solution was added until an aqueous solution of modified cutin extract having a 25-35 wt% dry content and pH 7-9 was obtained. Filtration was performed using a 100 pm filter cloth. Brookfield® viscosity (31 wt% aqueous solution, at 25°C and pH 9) of the modified cutin extract: 800 mPa*s.
  • Avedex® 125 HI 12 dextrin derived from potato starch, commercially available from Avebe, commonly used to improve oil resistance of paper substrates.
  • Raw cutin extract (50-80 wt% dry content, pH 3-6) obtained from waste tomato peels.
  • the modified cutin extracts prepared in the previous examples were used to prepare aqueous barrier coating compositions.
  • the obtained aqueous barrier coating compositions were applied at a coat weight of 5.5 g/m 2 on a paper substrate having a grammage of 80 g/m 2 .
  • Oil absorption capacity was tested using the KIT method, according to TAPPI Test Method UM 557.
  • numbered (from 1 to 16) solutions of increasing hydrophobicity are applied onto the paper substrate.
  • the highest numbered solution that does not stain the surface is reported as result of the KIT test.
  • Heat sealability was evaluated using a Gandus DD 100-200 ATR 121-141, an automatic sealing machine in compliance with DIN 58953 p-7, with a maximum heat sealing area of 196 mm x 13 mm and a heat sealing temperature range within 50-150 ⁇ 1°C.
  • the testing was conducted contacting two coated paper samples (50mm x 50mm) at a given temperature for 1 second. Then the heat sealing strengths were visually verified peeling off the two layers of the seal after cooling down at room temperature. The minimum temperature at which heat sealing occurs is reported.
  • Table 1 reports the results of the Cobb test and KIT test for aqueous barrier coating compositions containing the modified cutin extract of the invention, compared with aqueous barrier coating compositions containing an acrylic emulsion copolymer (Comparative Example 1), a dextrin derived from potato starch (Comparative Example 2), or a raw cutin extract (Comparative Example 3).
  • Table 2 reports the results of the heat sealability test for aqueous barrier coating compositions containing the modified cutin extract of inventive Examples 2 and 3, compared with aqueous barrier coating compositions containing an acrylic emulsion copolymer (Comparative Example 1), a dextrin derived from potato starch (Comparative Example 2), or a raw cutin extract (Comparative Example 3).
  • the modified cutin extracts of the present invention allow to obtain a paper substrate that has a similar water resistance, but a significantly improved oil resistance.
  • the modified cutin extracts of the present invention allow to obtain a paper substrate with improved oil resistance and significantly improved water resistance. This result is particularly remarkable, as paper substrates coated with natural polymers (such as starch) are typically affected by poor water resistance.
  • aqueous barrier coating compositions based on a dextrin derived from potato starch (Comparative Example 2) or a raw cutin extract (Comparative Example 3) did not allow to obtain a heat sealable paper substrate.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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PCT/EP2023/058459 2022-04-01 2023-03-31 Method for coating a paper substrate by using a modified cutin extract WO2023187159A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT102022000006464A IT202200006464A1 (it) 2022-04-01 2022-04-01 Metodo per rivestire un substrato di carta usando un estratto di cutina modificato
IT102022000006464 2022-04-01

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010093320A1 (en) * 2009-02-13 2010-08-19 Innventia Ab A method for separating from suberin and/or cutin containing plants, a solid and/or oil fraction enriched in cis-9,10- epoxy-18-hydroxyoctadecanoic acid
WO2015028299A1 (en) 2013-08-26 2015-03-05 CHIESA, Virginio Extraction method of a polyester polymer or cutin from the wasted tomato peels and polyester polimer so extracted
WO2016187581A1 (en) 2015-05-20 2016-11-24 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
WO2017100636A1 (en) * 2015-12-10 2017-06-15 Apeel Technology, Inc. Plant extract compositions for forming protective coatings
WO2018094269A1 (en) * 2016-11-17 2018-05-24 Apeel Technology, Inc. Compositions formed from plant extracts and methods of preparation thereof
US20190316050A1 (en) * 2018-04-11 2019-10-17 Regents Of The University Of Minnesota Fuel compositions based on binders from cutin-containing materials
WO2021019467A1 (en) * 2019-07-31 2021-02-04 Greentech Global Pte. Ltd. Saccharide fatty acid ester latex barrier coating compositions

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010093320A1 (en) * 2009-02-13 2010-08-19 Innventia Ab A method for separating from suberin and/or cutin containing plants, a solid and/or oil fraction enriched in cis-9,10- epoxy-18-hydroxyoctadecanoic acid
WO2015028299A1 (en) 2013-08-26 2015-03-05 CHIESA, Virginio Extraction method of a polyester polymer or cutin from the wasted tomato peels and polyester polimer so extracted
WO2016187581A1 (en) 2015-05-20 2016-11-24 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
WO2017100636A1 (en) * 2015-12-10 2017-06-15 Apeel Technology, Inc. Plant extract compositions for forming protective coatings
WO2018094269A1 (en) * 2016-11-17 2018-05-24 Apeel Technology, Inc. Compositions formed from plant extracts and methods of preparation thereof
US20190316050A1 (en) * 2018-04-11 2019-10-17 Regents Of The University Of Minnesota Fuel compositions based on binders from cutin-containing materials
WO2021019467A1 (en) * 2019-07-31 2021-02-04 Greentech Global Pte. Ltd. Saccharide fatty acid ester latex barrier coating compositions

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
G. TEDESCHI ET AL., ACS SUSTAINABLE CHEM. ENG., vol. 6, no. 11, 2018, pages 14955 - 14966
JOSÉ A HEREDIA-GUERRERO ET AL: "Cutin from agro-waste as a raw material for the production of bioplastics", JOURNAL OF EXPERIMENTAL BOTANY, vol. 68, no. 19, 8 August 2017 (2017-08-08), GB, pages 5401 - 5410, XP055667872, ISSN: 0022-0957, DOI: 10.1093/jxb/erx272 *

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