Classifications

• • 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
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
  • C08G59/50—Amines
  • C08G59/5006—Amines aliphatic
  • C08G59/502—Polyalkylene polyamines
• • 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
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
  • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
• • 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
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
  • C08G59/50—Amines
  • C08G59/5006—Amines aliphatic
  • C08G59/5013—Amines aliphatic containing more than seven carbon atoms, e.g. fatty amines
• • 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
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
  • C08G59/62—Alcohols or phenols
  • C08G59/621—Phenols
• • 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
  • 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
  • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins

Definitions

• nucleophile such as amines, esters, carboxylic acid
• bio-based raw materials Preferably bio-based raw materials
• cocopropylene diamine for use at room temperature by addition of salicylic acid that at high concentrations up to 40% (w/w) , cocopropylene diamine remains liquid at room and even lower temperatures.
• Other alkyl (poly) amines have been found to be liquefied by substituted phenols as well. This invention has further been described in an independent patent, which is filed parallel to the patent in the present case.
• cocopropylene diamine/salicylic acid composition By thoroughly mixing the cocopropylene diamine/salicylic acid composition with an epoxy resin, followed by curing either at room temperature ( ⁇ 48 hours) or at elevated
• polyalkenes and epoxidized polyalkadienes can be cured with the alkyl (poly) amine-substituted phenol curing agents as well, leading to a wide range of properties meeting several requirements of the current market demands .
• alkene- substituted aromatic hydrocarbons polydimethylsiloxane derivatives, such as polyester-modified PDMS, reactive
• solvents water scavengers, filling agents, pigments or mixtures thereof as well.
• the pot life (the time from combining the components of the coating to the point at which the mixed coating is either no longer usable or the viscosity has doubled from the
• Another option is to add small amounts ( ⁇ 5 % by weight based on amount of alkylpropylene diamine/salicylic acid) of another weaker organic acid, such as alkylphosphate esters, or C10-C20 linear or branched carboxylic acid.
• the curing time can increase at room
• Acceleration of epoxy curing can be obtained by addition of small amounts ( ⁇ 5% by weight based on amount of
• alkylpropylene diamine/salicylic acid compounds with a greater acidity than salicylic acid, e.g. aromatic sulphonic acids, such as dodecylbenzene sulphonic acid.
• Alkylated (poly) amines e.g. Duomeen CD (Akzo Nobel), Triameen C (Akzo Nobel) and Tetrameen C (Akzo Nobel)
• surface active compounds i.e. curing agents, dispersing agents, anti-corrosion film formers and flotation agents.
• the drawback for the group of fatty amines described above, is that they have the tendency to be solid or crystallize at/or below the most desirable operating
• WO2010/099281 claims high mechanical strength over a wide temperature range with products, comprising epoxy resin composition, comprising linear alkylamine, cyclic aliphatic amine and filler.
• the invention more specifically relates to a composition to protect surfaces, such as steel, carbon steel, stainless steel, polyethylenes , polypropylenes , polyacrylates , polyesters, wood, aluminium, ceramics and glass, very
• composition further comprises preferably
• Polydimethylsiloxane derivatives such as polyester modified PDMS
• the epoxy resin can be a cycloaliphatic epoxy, phenolic epoxy, Novolac epoxy, end- capped epoxy, epoxidized cardanol resin/epoxidized cashew nut shell liquid or mixtures thereof, and is specifically an epoxidized organosilane or siloxane, silicon epoxy resins or mixtures thereof.
• the epoxidized alkene is preferably epoxidized
• unsaturated natural oil or its corresponding fatty acids or mixtures thereof is in a preferred embodiment a
• n preferably 0 - 10.
• composition according to the invention comprises a substituted phenol ( B ) wherein:
• ⁇ Y H, COOH, carboxylate, OH, NH 2 , N0 2 , S0 3 H, COOR,
• Said substituted phenol ( B ) is preferably catechol or salicylic acid, and more preferably salicylic acid.
• Another option is to add small amounts ( ⁇ 5% by weight based on amount of
• alkylpropylene diamine/salicylic acid of another weaker organic acid (pKa > 2.7), such as alkylphosphate esters, orC10-C20 linear or branched carboxylic acid.
• pKa > 2.7 another weaker organic acid
• the curing time can increase at room temperature, whereas no differences are observed at higher curing temperatures .
• the resulting polymer layers showed no significant differences with the non- inhibited composition.
• Acceleration of epoxy curing can be obtained by addition of small amounts ( ⁇ 5% by weight based on amount of
• substituted phenol (B) can at least partially be replaced by a hydroxylated thiophene, hydroxylated pyridine, hydroxylated pyrrole, hydroxylated furan, hydroxylated polycyclic hydrocarbon or hydroxylated substituted polycyclic hydrocarbon compound.
• polycyclic hydrocarbon or hydroxylated substituted polycyclic hydrocarbon may further comprise a carboxylic acid or
• composition according to the invention may further comprise colouring agents, in particular pigments, or filling agents, especially nanoparticles or modified nanoparticles , in particular silicium dioxide nanoparticles.
• the invention also relates to a method for curing the present composition by heating the curing system to a
• Cocopropylene diamine (Duomeen CD - Akzo Nobel Surface Chemistry) is molten at 40 °C. 50 grams Duomeen CD is transferred into a glass beaker, equipped with a magnetic stirring bar, followed by slow addition of 27 grams salicylic acid (1 : 1 molar ratio) . Stirring is continued till a clear light yellow solution is obtained.
• the protective layers have been prepared as follows.
• the starting materials have been thoroughly mixed in a 50 ml.

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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)
• Epoxy Resins (AREA)
• Paints Or Removers (AREA)
• Compositions Of Macromolecular Compounds (AREA)

Applications Claiming Priority (2)

Publications (1)

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Family Cites Families (11)

• 2011
  • 2011-06-23 NL NL1038882A patent/NL1038882C2/en not_active IP Right Cessation
• 2012
  • 2012-06-25 WO PCT/NL2012/000039 patent/WO2012177120A1/en unknown
  • 2012-06-25 NL NL1039697A patent/NL1039697C2/en not_active IP Right Cessation
  • 2012-06-25 CN CN201280041001.XA patent/CN103764711B/zh not_active Expired - Fee Related
  • 2012-06-25 EP EP12735662.4A patent/EP2723794A1/en not_active Withdrawn

Non-Patent Citations (2)

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