WO2009155086A2 - Produits chimiques et intermédiaires à base de ressources renouvelables - Google Patents

Produits chimiques et intermédiaires à base de ressources renouvelables Download PDF

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WO2009155086A2
WO2009155086A2 PCT/US2009/045609 US2009045609W WO2009155086A2 WO 2009155086 A2 WO2009155086 A2 WO 2009155086A2 US 2009045609 W US2009045609 W US 2009045609W WO 2009155086 A2 WO2009155086 A2 WO 2009155086A2
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bio
derived
carbon atoms
carbon
produced
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PCT/US2009/045609
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WO2009155086A3 (fr
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Jeffery W. Johnson
Peter William Uhlianuk
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E. I. Du Pont De Nemours And Company
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Publication of WO2009155086A2 publication Critical patent/WO2009155086A2/fr
Publication of WO2009155086A3 publication Critical patent/WO2009155086A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08L61/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine
    • 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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
    • C08G12/32—Melamines
    • 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
    • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
    • C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C09D161/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C09D161/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine

Definitions

  • This disclosure is related to the field of renewable resourced materials. Specifically, the disclosure relates to solvents, intermediates and other chemical products that are produced from renewable resources and are useful for displacing those materials that are currently derived from petroleum feedstocks. Of particular interest are solvents, monomers, polymers and additives that can be used in the field of paints and coatings, especially automotive coatings.
  • An example of this is polytrimethylene terephthalate.
  • the trimethylene portion of the molecule can be derived from 1 ,3-propane diol that is derived from bio-sources.
  • the terephthalic acid comes from a petroleum source, so the polyester is only partially derived from renewable resources.
  • each R 1 and R 2 are independently selected from the group of H and CH 2 OH and wherein the carbon atoms of each CH 2 OH present in the molecule is derived from bio-formaldehyde.
  • each of R 3 and R 4 is independently selected from the group H and CH 2 OR 5 ; each R 5 is independently selected from an alkyl group having from 1 to 4 carbon atoms; the carbon atoms of each CH 2 O present in the molecule is derived from bio-formaldehyde; and wherein each of the carbon atoms of each R 5 present is derived from a bio-alcohol.
  • the phrases “renewable resource” and “renewably resourced” mean that the material or process described comprise components that can be derived from plant or animal material, commonly called bio-mass.
  • the components may be naturally occurring in the bio-mass or may be the transformation product of natural or genetically engineered organisms or other chemical transformation processes. Suitable examples for the transformation of bio-mass include, for example, chemical processes, biological fermentation; anaerobic yeast, fungal or bacterial processes; aerobic yeast, fungal or bacterial process; and chemical enzyme process.
  • the components may be produced in their pure form or they may require a step or steps of isolation and/or purification prior to use. While the components may be capable of being derived from petroleum feedstock, the phrases are intended to exclude components that specifically derive 100 percent of their carbon atoms from petroleum feedstock.
  • bio- placed as a prefix means that at least a portion of the carbon atoms of the component are derived from a renewable resource. Also included within this definition are those components that are produced naturally in plants. For example, bio-limonene and bio-isobomyl alcohol can be harvested from various plants. While the component may be capable of being derived from petroleum feedstock, the prefix is intended to exclude those components that specifically derive all of their carbon atoms from petroleum feedstock.
  • bio-ethanol means ethanol that is formed from renewable resources. All of the carbon atoms in bio-ethanol derived from, for example, fermentation, are from renewable resources.
  • a component is the reaction product of two or more intermediates, then to be described as a bio-component, at least a portion of the carbon atoms that form a part of the final component must be derived from biomass sources. Catalysts, solvents or other adjuvants that are used to facilitate the reaction, but do not form a part of the final bio-component, do not necessarily need to be derived from biomass.
  • a bio-component derives all of its carbon content from renewable resources.
  • a bio-monomer produced from the esterification reaction between bio-acrylic acid and bio- ethanol to form bio-ethyl acrylate derives 100 percent of it carbon from renewable resources.
  • a bio-component derives greater than 1 percent of its carbon from renewable resources.
  • a bio- monomer produced from the esterification reaction between petroleum based acrylic acid (containing 3 carbon atoms) and bio-ethanol (containing 2 carbon atoms) to form bio-ethyl acrylate derives 40 percent of it carbon from renewable resources.
  • a bio-component derives greater than 10 percent of its carbon from renewable resources.
  • a bio-component derives greater than 20 percent of its carbon from renewable resources.
  • bio-based components differ from petroleum-based components. Petroleum-based components do not have the carbon 14 isotope present. Bio-based products have an identifiable amount of carbon 14. Carbon 14 is present in bio-mass as a result of carbon dioxide that is formed when nitrogen is struck by an ultra-violet light produced neutron, causing the nitrogen to lose a proton and form carbon of molecular weight 14 which is immediately oxidized to carbon dioxide. This radioactive isotope represents a small but measurable fraction of atmospheric carbon. Atmospheric carbon dioxide is cycled by green plants to make organic molecules during the process known as photosynthesis. The cycle is completed when the green plants or other forms of life metabolize the organic molecules producing carbon dioxide which is released back to the atmosphere. Virtually all forms of life on Earth depend on this green plant production of organic molecule to produce the chemical energy that facilitates growth and reproduction. Therefore, the carbon 14 that exists in the atmosphere becomes part of all life forms, and their biological products.
  • the application of ASTM-D6866 to derive a "bio-based content" is built on the same concepts as radiocarbon dating, but without use of the age equations.
  • the analysis is performed by deriving a ratio of the amount of radiocarbon (carbon 14) in an unknown sample to that of a modem reference standard. The ratio is reported as a percentage with the units "pMC" (percent modern carbon). If the material being analyzed is a mixture of present day radiocarbon and fossil carbon (containing no carbon 14), then the pMC value obtained correlates directly to the amount of biomass material present in the sample.
  • the modern reference standard used in radiocarbon dating is a NIST (National Institute of Standards and Technology) standard with a known radiocarbon content equivalent approximately to the year AD 1950.
  • AD 1950 was chosen since it represented a time prior to thermo-nuclear weapons testing which introduced large amounts of excess radiocarbon into the atmosphere with each explosion (termed "bomb carbon").
  • the AD 1950 reference represents 100 pMC.
  • a biomass content result is derived by assigning 100% equal to 107.5 pMC and 0% equal to 0 pMC. In this regard, a sample measuring 99 pMC will give an equivalent bio-based content result of 93%.
  • a bio-solvent is produced from renewable resources.
  • the bio-solvent may not be directly available from the renewable resource.
  • the component that can be derived from the renewable resource may need to undergo one or more chemical reactions and/or purification steps to form the desired bio-solvent.
  • two or more chemical components at least one of which is derived from biomass sources, are used to produce the desired bio-solvent.
  • two or more chemical components, each of which is derived from bio-mass sources are used to produce the desired bio-solvent.
  • the esterifi cation of bio-acetic acid with bio-butanol can form bio- butyl acetate.
  • a bio-solvent derives greater than 10 percent of its carbon from renewable resources.
  • a bio-solvent derives greater than 20 percent of its carbon from renewable resources.
  • solvents include alcohols, esters, ketones, ethers and hydrocarbons. Many of these materials are not available as pure compounds from bio-mass sources, but the reaction of two or more compounds available via bio-transformation processes can result in useful solvents.
  • Suitable alcohols that can be produced via renewable resources include mono-, di-, tri- and higher alcohols having 1 or more carbon atoms.
  • Bio-methanol, bio-ethanol and bio-butanol can be formed by well-known fermentation process. Other alcohols can be produced as well, see for example, US 4,536,584.
  • Ester-based solvents can be produced from the reaction of a bio- carboxylic acid and a bio-alcohol.
  • Suitable acids that can be produced via renewable resources include, for example, formic acid, acetic acid, propionic acid, butyric acid, lactic acid, malonic acid, and adipic acid. See US
  • Ester-based solvents are widely used in the chemical industry, especially as polymerization solvents and reducers in the paint and coating industry.
  • Bio-esters can be formed from a bio-acid and a bio-alcohol via the well-known esterification industrial process of these generic components.
  • bio-acetic acid can be reacted under esterification reaction conditions with bio-butanol to form bio-butyl acetate.
  • Bio-butyl acetate can be used in the synthesis of polyacrylates and as a reducer for many paint and coating applications.
  • bio-tert-butyl acetate can be produced using Indium catalysts, see Journal of Molecular Catalysis, volume 235, page 150-153, 2005.
  • Ketone-based and aldehyde-based solvents can be produced by the oxidation of many of the above listed bio-alcohols.
  • Bio-acetone, bio-methyl ethyl ketone, bio-cyclopentanone, bio-cyclohexanone, bio-2-pentanone, bio- 2,5-hexanedione, and the various isomers of 4 to 6 carbon bio-ketones are useful as solvents in many chemical reactions, such as, for example, free radical polymerization and they can also be used as a reducer in paint and coating applications. See for example, US 4,536,584.
  • Bio-ethers including bio-polyethers, can be produced from bio-mass or via the condensation of bio-alcohols with bio-ketones and bio-aldehydes according to known ether forming reaction processes. Examples include, bio- diethoxymethane and bio-tetrahydrofuran. See for example, US 4,536,584. Other methods to produce bio-polyethers can include, the polymerization of bio-ethylene oxide. Bio-ethylene oxide can be produced from the epoxidation of bio-ethylene. Low molecular weight polyethers, especially alkyl capped- polyethers, are commonly used as solvents.
  • Alkane hydrocarbon solvents are commonly used in free radical polymerizations.
  • Bio-hydrocarbons having in the range of from 1 to 15 carbon atoms can be produced from bio-mass according to the procedures given in US 6, 180,845 or Chemistry and Sustainable Chemistry, Volume 1 , pages 417-424, 2008. Distillation or other purification procedures can provide pure fractions of bio-hydrocarbons, such as, for example, bio-hexane that can be used in, for example, free radical polymerization processes.
  • Aromatics such as, toluene and xylene, are also commonly used in polymerization reactions and as reducers in coatings formulations. Using fast-pyrolosis techniques and certain zeolites, it is possible to produce bio- aromatics that can be used for polymerization solvents and as reducers for the paint and coatings industry. See for example, Chemistry and Sustainable Chemistry, Volume 1 , pages 397-400, 2008.
  • bio-acrylic acid and bio-methacrylic acid monomers can be used to form numerous bio-alkyl acrylate and bio-alkyl methacrylate esters as well as bio-acrylamides, bio-methacrylamides, bio-acrylonitrile and bio- methacrylonitrile.
  • Bio-acrylate and bio-methacrylate esters can be produced, via esterification reactions with bio-alcohols. By incorporating an excess of bio-diols into the esterification reaction, hydroxy functional bio-acrylate and bio-methacrylate esters can be formed.
  • bio-acrylic acid and bio-methacrylic acid with bio-diols
  • bio- diacrylates and bio-dimethacrylates can be formed.
  • These types of monomers find widespread use in the acrylic polymers used in the paint and coatings industry.
  • a representative sample of bio-alkyl acrylate and bio-alkyl methacrylate esters are shown in TABLE 1. This table is meant to provide a sample of the commercially important bio-acrylate and bio-methacrylate esters that can be produced from bio-sources.
  • Bio-epichlorhydrin is also available from glycerol, a renewable resource, via the EPICEROLTM process developed by Solvay.
  • Bio- epichlorohydrin allows the formation of bio-glycidyl acrylate and bio-glycidyl methacrylate monomers, which are two monomers that find use in the paints and coatings industry.
  • acrylic and methacrylic esters monomers make up the majority of the monomers that are used to produce acrylic polymers
  • other monomers can be copolymerized with these ester monomers to modify the properties of the polymer. This is especially useful for producing acrylic polymers used in the paint and coatings industry.
  • These monomers can include, for example, acrylamide, methacrylamide, acrylonitrile and methacrylonitrile, styrene and styrene derivatives, or combinations thereof are often used.
  • Bio-acrylamides and bio-methacrylamides can be derived from the corresponding bio-acrylic acid and bio-methacrylic acid, for example, by the formation of bio-acid chlorides, followed by amination with ammonia or other primary and/or secondary amines.
  • Bio-acrylonitrile and bio-methacrylonitrile can be produced by the dehydration of bio-acrylamide and bio-methacrylamide using, for example, phosphorus pentoxide.
  • Bio-styrene can be produced from phenylalanine by the deamination using phenylalanine ammonia lyase, which results in the formation of cinnamic acid.
  • the formed cinnamic acid can then be decarboxylated using a variety of methods, including bio-synthetic pathways. See for example, The Chemical and Pharmaceuticals Bulletin, Volume 49(5), pages 639-641 , 2001.
  • Another group of monomers that are important to the coating industry are the monomers that produce polyesters.
  • These monomers include monoalcohols, diols, triols and higher polyols; monocarboxylic acids, dicarboxylic acids, and higher carboxylic acids; as well as hydroxy-functional carboxylic acids, for example, 12-hydroxy stearic acid.
  • bio-mass sources thereby providing a route to bio-monomers that can be used to form bio-polyesters.
  • Bio-alcohols and some bio-acids have been discussed above. Bio-diacids are also available. References can be found to produce bio-adipic acid as well as other diacids; see for example, US 4,400,468 and US 4,965,201.
  • all of the carbon atoms of the monomer are derived from bio-mass.
  • greater than 10 percent of the carbon atoms of the monomer are derived from bio-mass.
  • greater than 20 percent of the carbon atoms of the monomer are derived from bio-mass.
  • all of the carbon atoms of the polymer are derived from bio-mass.
  • Bio-melamine resins and polyisocyanate compounds are important to many industries, including the paint and coatings industry where they are often use as crosslinking agents in coating compositions.
  • Bio-melamine resins can be produced by the reaction of melamine with a bio-aldehyde, typically bio-formaldehyde, to form bio-methyol melamine, bio-dimethyol melamine, bio-trimethylol melamine, up to and including bio-hexamethylol melamine.
  • This class of bio-melamine resins is useful as a crosslinking agent for many coatings and can be represented by compounds of the formula;
  • each R 1 and R 2 are independently selected from the group of H and CH 2 OH.
  • at least the carbon atom of each CH 2 OH is derived from a renewable resource, via bio-formaldehyde.
  • Melamine can be produced via the trimerization of cyanamide. Cyanamide is available from urea, which is the dehydration product of ammonium carbonate. Ammonium carbonate can be derived from ammonia and carbon dioxide. If the carbon dioxide were isolated from air, it would be possible that all of the carbon atoms in the above described melamines to have a measurable carbon 14 signature.
  • Methylol melamine resins are often treated with an alcohol under acidic conditions to form etherated melamine resins.
  • Bio-alcohols discussed above, can be used to form bio-etherated melamine resins that are derived from renewable resources.
  • the alcohols used to produce the ether group are low molecular weight alcohols ranging from methanol to isomers of butanol.
  • Etherated melamines typically have a structure according to the formula; wherein each of R 3 and R 4 is independently selected from the group H and CH 2 OR 5 ; each R 5 is independently selected from an alkyl group having from 1 to 4 carbon atoms; the carbon atoms of each CH 2 O present in the molecule is derived from bio-formaldehyde; and wherein each of the carbon atoms of each R 5 present is derived from a bio-alcohol.
  • Amines and diamines from bio-sources can be used to produce bio- isocyanates and bio-polyisocyanates that are also used in the coatings industry as crosslinking agents. The amine functional group is easily converted to an isocyanate functional group when reacted with phosgene.
  • Diamines can be produced from biomass, as in US 7,189,543, or they can be synthesized from a variety of compounds that are available from bio-sources.
  • bio-alcohols can be oxidized to the corresponding bio-ketones and/or bio-aldheydes and then be subjected to reductive amination procedures.
  • Bio-acids can be converted to bio-nitriles and then hydrogenated to form the desired bio-amines.
  • Other methods are known in the art for producing amine groups from a variety of starting materials, many that are available from renewable resources.
  • bio-isocyanate functional compounds can be used in any of the forms that are typically employed in the paint and coating industry.
  • bio-1 ,6-hexamethylene diisocyanate can be trimerized to form the isocyanurate of 1 ,6-hexamethylene diisocyanate.
  • Any other bio- polyisocyanate can also be homopolymerized to form any of the known isocyanate adducts, including, for example, carbodiimides, isocyanurates, uretidiones, allophanates, and/or biurets.
  • Bio-isocyanates such as, for example, bio-1 ,6-hexamethylene diisocyanate or any other suitable bio-polyisocyanate can be blocked with a blocking agent to form a blocked isocyanate allowing the formation of one- component coating compositions that unblock and are capable of forming crosslinks with suitable film-forming binders upon the application of heat.
  • Suitable blocking agents include, for example, bio-alcohols and oximes.
  • Bio- alcohols include, for example, bio-methanol, bio-ethanol, isomers of bio- propanol, isomers of bio-butanol .
  • Bio-oximes can be produced by the reaction of a bio-aldehyde or a bio-ketone with hydroxylamine. The oximes can then be reacted with bio-isocyanates and/or bio-polyisocyanates to block the isocyanate groups.
  • all of the carbon atoms of the bio-melamine resin are derived from bio-mass.
  • greater than 10 percent of the carbon atoms of the bio-melamine resin are derived from bio-mass.
  • greater than 20 percent of the carbon atoms of the bio-melamine resin are derived from bio-mass. In one embodiment, all of the carbon atoms of the etherated bio- melamine resin are derived from bio-mass.
  • greater than 10 percent of the carbon atoms of the etherated bio-melamine resin are derived from bio-mass.
  • greater than 20 percent of the carbon atoms of the etherated bio-melamine resin are derived from bio-mass.
  • all of the carbon atoms of the bio-isocyanate are derived from bio-mass.
  • greater than 10 percent of the carbon atoms of the bio-isocyanate are derived from bio-mass. In a third embodiment, greater than 20 percent of the carbon atoms of the bio-isocyanate are derived from bio-mass.
  • additives for coating compositions that are currently produced, at least in part from petroleum feedstocks could also be prepared from bio- sources.
  • cellulose acetate butyrate (CAB) is a commonly used additive in many coating compositions.
  • Cellulose itself is available from biomass and the reaction of cellulose with bio-acetic acid and bio-butyric acid can form bio-CAB.
  • the paint and coatings industry produces many types of coating compositions.
  • the automotive coatings industry produces coatings that are used a primers, basecoats, clearcoats, monocoats and others.
  • Each of these types of coatings utilizes a film-forming polymeric binder to provide a coating composition that provides adhesion to the underlying substrate, chip resistance, protection from ultraviolet radiation, gloss, and other aesthetic attributes according to their specific function.
  • the coating compositions can also include solvents, crosslinking agents, pigments and other additives.
  • Coating formulations will often use acrylic polymers, polyester polymers, polyesterurethane polymers, polyethers, polyetherurethanes, or combinations thereof as the film-forming binders. These film-forming binders can optionally be crosslinked using any of the previously described crosslinking agents.
  • a monomer mixture is typically polymerized in a solvent using free radical initiators.
  • the acrylic polymers formed can be linear, graft, comb, crosslinked microgel resins or any of the known acrylic polymers that are typically used in coating compositions.
  • Bio-solvents are optional during the polymerization and, if used, typically remain as a part of the coating composition and help to produce a coating composition that is able to flow forming a continuous and relatively flat layer of coating composition on the substrate to which it is applied.
  • the bio-solvents can evaporate to give a crosslinked coating that is essentially free from the bio-solvent.
  • bio-solvents any of the bio-solvents, bio-monomers and bio-crosslinking agents described herein, one of ordinary skill in the art could produce bio-acrylic coating compositions wherein substantially all of the carbon atoms that form the crosslinked polymer network have come from renewably resourced materials.
  • Bio-polyesters can be formed that are linear, branched, graft or any other configuration known in the art. Formation of bio-polyesters uses essentially the same procedures as polyesters from non-renewable resources.
  • the bio-polyesters can be formed from neat mixtures of the bio- monomers or bio-solvents can be added.
  • the bio-polyesters can then be formulated into coating compositions with or without crosslinking agents. Especially useful in a coating composition are those polyesters that are hydroxyl functional. The hydroxyl functional group allows the polyester to react with a crosslinking agent to form a crosslinked network.
  • Hydroxyl-functional bio-polyesters can also be reacted with bio- isocyanates or bio-polyisocyanates to form bio-polyesterurethanes.
  • the urethane (carbamate) group provides excellent properties in a crosslinked coating, especially in automotive coatings.
  • Bio-polyethers were previously described in the solvent section. These polymers can be used as film-forming polymers when formulating coating compositions.
  • Star-type polyethers can be formed by initiating the polyether formation with a polyol such as, for example, sorbitol, glycerol, or other bio-polyol.
  • polyethers used for coating compositions have hydroxyl functional groups to allow the polyether to be crosslinked with the crosslinking agents.
  • Bio-polyetherurethanes can be formed by the reaction of hydroxyl- functional bio-polyethers with bio-isocyanates or bio-polyisocyanates.
  • the urethane (carbamate) group provides excellent properties in a crosslinked coating, especially in automotive coatings.
  • solvents, monomer, polymers and other additives disclosed herein are described in terms of their use in the paint and coatings industry, they are also suitable for use in many other industries.
  • the solvents, monomer, polymers and additives described can be used in, for example, a pharmaceutical composition, an agricultural composition, an adhesive composition, an ink composition, a lubricant composition, a fuel composition or other industrial composition.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne des solvants, des monomères, des polymères, des agents de réticulation et d'autres additifs, notamment ceux utilisés dans l'industrie des peintures et des revêtements et qui sont dérivés de ressources renouvelables.
PCT/US2009/045609 2008-05-30 2009-05-29 Produits chimiques et intermédiaires à base de ressources renouvelables WO2009155086A2 (fr)

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US8083064B2 (en) 2011-01-25 2011-12-27 The Procter & Gamble Company Sustainable packaging for consumer products
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WO2012142271A1 (fr) 2011-04-12 2012-10-18 The Procter & Gamble Company Emballage barrière souple issu de ressources renouvelables
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WO2013158477A1 (fr) 2012-04-16 2013-10-24 The Procter & Gamble Company Bouteilles en plastique pour compositions de parfum ayant une résistance au faïençage améliorée
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US8629236B2 (en) 2010-09-28 2014-01-14 Axalta Coating Systems Ip Co., Llc Polyester having renewable 1,3-propanediol
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WO2014209602A1 (fr) 2013-06-24 2014-12-31 The Procter & Gamble Company Emballage en film mousse
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