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WO1996012774A1 - Revetements a base de derives de lignine, durcissables par rayonnement - Google Patents

Revetements a base de derives de lignine, durcissables par rayonnement Download PDF

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Publication number
WO1996012774A1
WO1996012774A1 PCT/EP1995/003986 EP9503986W WO9612774A1 WO 1996012774 A1 WO1996012774 A1 WO 1996012774A1 EP 9503986 W EP9503986 W EP 9503986W WO 9612774 A1 WO9612774 A1 WO 9612774A1
Authority
WO
WIPO (PCT)
Prior art keywords
lignin
meth
radiation
derivatives
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1995/003986
Other languages
German (de)
English (en)
Inventor
Wolfgang Reich
Jörg Breitenbach
Harald Larbig
Erich Beck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to EP95936463A priority Critical patent/EP0787170A1/fr
Priority to JP8513507A priority patent/JPH10507480A/ja
Priority to AU38407/95A priority patent/AU3840795A/en
Publication of WO1996012774A1 publication Critical patent/WO1996012774A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C09D197/00—Coating compositions based on lignin-containing materials
    • C09D197/005—Lignin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • 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
    • C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
    • C09D167/07—Unsaturated polyesters having carbon-to-carbon unsaturation having terminal carbon-to-carbon unsaturated bonds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

  • the invention relates to a method for producing coatings. It is generally known to use (meth) acrylates for the production of coatings.
  • (meth) acrylates for the production of coatings.
  • Mono- or poly (meth) acrylates such as alkyl (meth) acrylates, alkylene di-, tri- or tetra (meth) acrylates, urethane (meth) acrylates, epoxy (meth) acrylates, polyether or polyesters (meth) acrylates.
  • Lignin as a renewable raw material is known to be obtained from wood processing. For example, through implementation with
  • the object of the present invention was a process for the production of coatings in which all or part of the compounds used hitherto are replaced by those based on renewable raw materials, these compounds exhibiting good reactivity in the radiation curing and the cured coatings obtained should have satisfactory application properties. Accordingly, a process for the production of coatings has been found, in which radiation-curable compounds which contain at least 5% by weight, based on these compounds, of radically copolymerizable lignin derivatives are applied to substrates and cured.
  • radiation-curable i.e. Radically copolymerizable compounds applied to substrates.
  • Such radiation curable compounds are e.g. Compounds of the formula
  • X represents an n-valent C 1 -C 2 alkyl radical, which can optionally be substituted by 1 to 3 hydroxyl groups
  • R 1 represents an H atom or a methyl group and n has the meaning of an integer from 1 to 4 has.
  • Compounds of the formula I are, for example, -C 2 -C 8, preferably C 1 -C 6 alkyl (meth) acrylates, C 2 -C 10 -alkylenedi (meth) acrylates or trimethylolpropane mono-, di- or tri (meth) acrylate, Pentaerythritol mono-, di-, tri- or tetra (meth) acrylate.
  • the radiation-curable compounds can be polyester or polyether (meth) acrylates. Preferred are those obtained by reacting (meth) acrylic acid with 1 to 6, preferably 2 to 4 hydroxyl-containing polyesters or polyethers.
  • the molecular weights M n of the polyesters or polyethers are preferably between 100 and 4000.
  • Such hydroxyl-containing polyesters can be prepared, for example, in a customary manner by esterifying dicarboxylic acids or polycarboxylic acids with diols or polyols.
  • the starting materials for such hydroxyl-containing polyesters are known to the person skilled in the art.
  • Preferred dicarboxylic acids are succinic acid, glutaric acid, adipic acid, sebacic acid, o-phthalic acid, Acid, its isomers and hydrogenation products and esterifiable derivatives, such as anhydrides, for example maleic anhydride or dialkyl esters of the acids mentioned are used.
  • Tri- or tetraacids such as trimellitic anhydride or benzene tetracarboxylic acid may be mentioned as polycarbonic acid or its anhydrides.
  • Suitable diols are preferably ethylene glycol, propylene glycol 1,2 and 1,3, butane diol 1,4, hexane diol 1,6, neopentyl glycol, cyclohexane dimethanol and polyglycols of the ethylene glycol and propylene glycol type.
  • Trimethylolpropane, glycerol or pentaerythritol are primarily mentioned as polyols.
  • diols or polyols are oxyalkylated (e.g. with ethylene oxide or propylene oxide) diols or polyols, in particular with a degree of oxyalkylation of 0 to 10, based on the respective hydroxyl groups of the diol or polyol.
  • oxyalkylated diols or polyols in particular with a degree of oxyalkylation of 0 to 10, based on the respective hydroxyl groups of the diol or polyol.
  • polyesterols to be used according to the invention also include polycaprolactone diols and triols, the preparation of which is likewise known to the person skilled in the art.
  • hydroxyl-containing polyethers examples include those in question which can be obtained by known processes by reacting di- and / or polyhydric alcohols with different amounts of ethylene oxide and / or propylene oxide. Similarly, polymerization products of tetrahydrofuran or butylene oxide can also be used.
  • Oxalkylation products of the abovementioned diols or polyols are preferred, in particular with a degree of oxalkylation of 0 to 10, based on the respective hydroxyl groups of the diol or polyol, at least 2 ether groups being contained in the molecule.
  • Urethane (meth) acrylates such as are obtainable by reacting mono-isocyanates or polyisocyanates with (meth) acrylates containing hydroxyl groups, in particular also those of the formula I, are also used as radiation-curable compounds for the production of coatings.
  • polyisocyanates are aliphatic, cycloaliphatic and aromatic diisocyanates, for example 1,4-butanediisocyanate, 1,6-hexanediisocyanate, 2,2,4- and 2,4,4-trimethylhexamethylene diisocyanate, cyclohexanediisocyanate, methylcyclohexanedi isocyanate, isophorone diisocyanate, 4,4'-diisocyanatodiphenylmethane, 4,4'-diisocyanatodicyclohexylmethane, 2,4- and 2,6-tolylene diisocyanate, tetramethylxylylene diisocyanate.
  • 1,4-butanediisocyanate 1,6-hexanediisocyanate
  • 2,2,4- and 2,4,4-trimethylhexamethylene diisocyanate 2,2,4- and 2,4,4-trimethylhexamethylene diisocyan
  • epoxy (meth) acrylates may be mentioned, e.g. such as those obtained by reacting epoxidized olefins or diglycidyl ethers, e.g. aromatic polyepoxides, such as bisphenol A diglycidyl ether with (meth) acrylic acid are available.
  • the radiation-curable compounds used in the process according to the invention contain at least 5% by weight of radiation-curable, free-radically copolymerizable lignin derivatives, based on the total amount of the radiation-curable compounds.
  • the radiation-curable compounds can also be exclusively lignin derivatives.
  • Coatings with good hardness and good elasticity can e.g. are obtained if the radiation-curable compounds consist of 5 to 50, preferably 5 to 40% by weight of lignin derivatives.
  • Radiation-curable lignin derivatives are e.g. with allyl or
  • Corresponding lignin derivatives can e.g. are obtained by reacting lignin with (meth) acrylic acid chloride or (meth) acrylic anhydride, e.g. in Cellulose Chem. Technol. 9, 71-77 (1975).
  • lignin can be alkoxylated, in particular ethoxylated or propoxylated, by known processes.
  • the alkoxylated lignin can then easily be reacted with (meth) acrylic acid to give a radiation-curable lignin derivative.
  • Lignins which are alkoxylated on average with 0.5 to 10, particularly preferably with 1 to 5, alkoxy groups per hydroxyl group are preferably used here. These lignins can then be reacted with (meth) acrylic acid by conventional esterification processes. Because of their low viscosity, the lignin derivatives obtained in this way are particularly suitable for the process according to the invention.
  • Lignin can also be reacted with isocyanate compounds.
  • radiation-curable lignins can be obtained by reacting lignin with e.g. Isocyanato-alkyl (meth) acrylates are converted into radiation-curable derivatives.
  • lignin can e.g. also with poly-isocyanates and hydroxyalkyl (meth) acrylates, e.g. those of the formula I or the above-described polyether or polyester (meth) acrylates, which additionally carry at least one hydroxyl group, are converted into radiation-curable derivatives.
  • the radiation-curable lignin derivatives preferably have an average molecular weight M n of 500 to 5000 M n , in this case by gel chromatography with polystyrene as the standard and tetrahydrofuran as the eluent, as described in Am. Chem. Soc, Symp. Ser. 397 (1989), pages 100-108.
  • the radiation-curable lignin derivatives preferably contain 1 to 20% by weight, particularly preferably 2 to 10% by weight, very particularly preferably 3 to 6% by weight of the copolymerizable ethylenically unsaturated group>
  • C C ⁇ (based on the radiation-hardened group) - cash lignin derivatives).
  • the radiation-curable compounds are applied to substrate surfaces.
  • the radiation-curable compounds can also contain further additives, e.g. Film forming aids, thickeners, defoamers or dyes, fillers or pigments are added.
  • further additives e.g. Film forming aids, thickeners, defoamers or dyes, fillers or pigments are added.
  • solvents are also used if the radiation-curable compounds are solid or have too high a viscosity.
  • Suitable solvents are, for example, dioxane, butyl acetate, ethyl acetate, dimethylformamide, N-methylpyrrolidone, ketones such as methyl, ethyl ketone.
  • the application can be carried out by conventional methods such as brushing, knife coating of the syringes.
  • Suitable substrates are those made of metal, plastic, paper or wood. Wood and paper are preferred.
  • solvents if present, can be removed, for example by increasing the temperature, and then thermal or photochemical curing can be carried out, preferably at room temperature. Photochemical curing by irradiation with high-energy light, for example electron beams or UV light, is preferred.
  • the radiation-curable compounds used according to the invention show good reactivity with regard to radiation curing and result in scratch-resistant coatings even after a short exposure.
  • photoinitiators are suitably added to the radiation-curable compounds, preferably in amounts of 0.05 to 5% by weight, based on the radiation-curable compounds.
  • Possible photoinitiators are e.g. Benzophenone and derivatives thereof, e.g. Alkylbenzophenones, halogen-methylated benzophenones, Michler's ketone, as well as benzoin and benzoin ethers such as ethylbenzoin ether, benzil ketals such as benzil dimethyl ketal, acetophenone derivatives such as e.g. Hydroxy-2-methyl-l-phenylpropan-l-one and hydroxycyclohexyl-phenylketone, anthraquinone and its derivatives such as methylanthraquinone and especially acylphosphine oxides such as e.g. Lucirin® TPO (2, 4,6-trimethylbenzoyldiphenylphosphine oxide).
  • Benzophenone and derivatives thereof e.g. Alkylbenzophenones, halogen-methylated benzophenones, Michler's
  • the photoinitiators which, depending on the intended use of the compositions according to the invention, are used in amounts between 0.1 and 15% by weight, preferably 1 to 10% by weight, based on the polymerizable components, can be used as a single substance or, because of their more frequent use synergistic effects, can also be used in combination.
  • the cured coatings have good application properties, e.g. good hardness and flexibility.
  • Stabilizers and 1.8 g of sulfuric acid were added to acrylic acid and 76.6 g of methylcyclohexane, and the mixture was heated to 100.degree.
  • 13 ml of acrylic acid-containing water with an acid number of 322.2 mg KOH / g were removed (56.4% esterification).
  • the solvent and excess of acrylic acid to an acid number of 46.2 mgKOH / g was distilled off ⁇ .
  • 24.4 g of bisphenol A diglycidyl ether (Epikote® 828) and 8.0 g of tetrabutylammonium bromide were then added at 107 ° C. After a reaction time of 3 hours, the product was filtered and filled.
  • the product had one Acid number of 2 mg KOH / g substance and a viscosity of 1.9 Pas.
  • the resin was mixed with 4% Irgacure 500, mounted on a bonder sheet with a box squeegee (layer thickness 50 ⁇ m) and irradiated with 2 UV lamps of 80 watts each in air, the speed of the conveyor belt being 13 m / min (5 times irradiated).
  • the pendulum damping was determined according to DIN 53157, which is a measure of the hardness of a coating, and the Erichsen depression according to DIN ISO 1520, which is a measure of the flexibility, elasticity of a coating.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

L'invention concerne un procédé de production de revêtements, selon lequel des composés durcissables par rayonnement, qui contiennent au moins 5 % en poids de dérivés de lignine copolymérisables par voie radicalaire, sont appliqués sur des substrats et sont durcis.
PCT/EP1995/003986 1994-10-21 1995-10-10 Revetements a base de derives de lignine, durcissables par rayonnement Ceased WO1996012774A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP95936463A EP0787170A1 (fr) 1994-10-21 1995-10-10 Revetements a base de derives de lignine, durcissables par rayonnement
JP8513507A JPH10507480A (ja) 1994-10-21 1995-10-10 リグニン誘導体をベースとする放射線硬化性被覆
AU38407/95A AU3840795A (en) 1994-10-21 1995-10-10 Radiation-curable coatings based on lignin derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4437720A DE4437720A1 (de) 1994-10-21 1994-10-21 Strahlungshärtbare Beschichtungen aus Basis von Ligninderivaten
DEP4437720.7 1994-10-21

Publications (1)

Publication Number Publication Date
WO1996012774A1 true WO1996012774A1 (fr) 1996-05-02

Family

ID=6531410

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/003986 Ceased WO1996012774A1 (fr) 1994-10-21 1995-10-10 Revetements a base de derives de lignine, durcissables par rayonnement

Country Status (5)

Country Link
EP (1) EP0787170A1 (fr)
JP (1) JPH10507480A (fr)
AU (1) AU3840795A (fr)
DE (1) DE4437720A1 (fr)
WO (1) WO1996012774A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014095800A1 (fr) * 2012-12-18 2014-06-26 Akzo Nobel Coatings International B.V. Compositions de revêtement à base de lignine
EP3409727A1 (fr) 2017-05-29 2018-12-05 Annikki GmbH Procédé de préparation d'un prépolymère de lignine
US10836929B2 (en) 2014-01-15 2020-11-17 Ppg Industries Ohio, Inc. Polyester polymers comprising lignin

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE539828C2 (en) 2016-04-29 2017-12-12 Innventia Ab Lignin-containing sealant and / or coating compositions from renewable sources

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3672817A (en) * 1970-12-14 1972-06-27 Westvaco Corp Alkylene chlorohydrin,oxide or carbonate modified sulfonated lignins in a disperse or vat dye cake
US4017430A (en) * 1975-06-23 1977-04-12 Georgia-Pacific Corporation Coating composition
US4339366A (en) * 1980-11-17 1982-07-13 Blount David H Process for the production of polyester resins
EP0314071A1 (fr) * 1987-10-28 1989-05-03 REED LIGNIN INC. (a Delaware Corp.) Liant à base de lignine sulfonée

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3672817A (en) * 1970-12-14 1972-06-27 Westvaco Corp Alkylene chlorohydrin,oxide or carbonate modified sulfonated lignins in a disperse or vat dye cake
US4017430A (en) * 1975-06-23 1977-04-12 Georgia-Pacific Corporation Coating composition
US4339366A (en) * 1980-11-17 1982-07-13 Blount David H Process for the production of polyester resins
EP0314071A1 (fr) * 1987-10-28 1989-05-03 REED LIGNIN INC. (a Delaware Corp.) Liant à base de lignine sulfonée

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014095800A1 (fr) * 2012-12-18 2014-06-26 Akzo Nobel Coatings International B.V. Compositions de revêtement à base de lignine
KR20150097554A (ko) * 2012-12-18 2015-08-26 아크조노벨코팅스인터내셔널비.브이. 리그닌-기재의 코팅 조성물
RU2652183C2 (ru) * 2012-12-18 2018-04-25 Акцо Нобель Коатингс Интернэшнл Б.В. Композиция для покрытия на основе лигнина
KR102166188B1 (ko) 2012-12-18 2020-10-16 아크조노벨코팅스인터내셔널비.브이. 리그닌-기재의 코팅 조성물
US10836929B2 (en) 2014-01-15 2020-11-17 Ppg Industries Ohio, Inc. Polyester polymers comprising lignin
EP3409727A1 (fr) 2017-05-29 2018-12-05 Annikki GmbH Procédé de préparation d'un prépolymère de lignine
WO2018219954A1 (fr) 2017-05-29 2018-12-06 Annikki Gmbh Procédé de préparation d'un prépolymère de lignine

Also Published As

Publication number Publication date
EP0787170A1 (fr) 1997-08-06
AU3840795A (en) 1996-05-15
JPH10507480A (ja) 1998-07-21
DE4437720A1 (de) 1996-04-25

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