Classifications

• • 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
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
  • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
  • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
  • C08G8/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol
• • 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
  • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
  • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
  • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
  • C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
• • 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

• the present invention relates to novel novolak compounds which are particularly useful as adhesion promoting curing agents in compositions which comprise epoxy resins and the compositions themselves.
• novolak resins are known to those skilled in the art. These novolaks are conventionally prepared by condensing phenol and formaldehyde in the presence of an acid catalyst Typically these known novolak resins are prepared with less than one mole of formaldehyde per mole of phenol. Generally, the most common starting materials are phenol and aqueous formaldehyde. These starting materials are selected because of their good reactivity, availability and low cost
• the acid catalyst is either an inorganic type such as sulfuric acid, hydrochloric acid, phosphoric acid, or other types known in the art.
• the acid may also be an organic acid such as p-toluenesulfonic acid, methanesulfonic acid or oxalic acid Certain catalysts are chosen for their reactivity or their influence on the properties, such as color.
• novolak resins upon heating, do not harden to an insoluble or infusible condition but remain organic solvent soluble and fusible They can be hardened or cured by the addition of a curing agent, such as hexamethylenetetramine or trioxane, and further heating
• the phenol and catalyst are intimately mixed
• the formaldehyde is added either by initially mixing with the phenol and catalyst, portionwise, or continuously over a defined time Because of practical considerations, the formaldehyde is usually added portionwise or continuously.
• the reaction generates heat, so cooling is often required.
• the mixture is heated to complete the reaction of the two components
• the novolak resin usually separates from the water layer and can be isolated at this point Alternatively, the reaction mixture can be dehydrated under heat and vacuum to isolate the novolak resin
• the novolak resin is a solid at room temperature.
• the molecular weight and softening temperature ofthe final resin may vary Typically, the number average molecular weight, as determined by size exclusion chromatography, ranges from 300 to 2000 or higher
• the source of aldehyde used to prepare these known novolak resins is aqueous formaldehyde.
• Paraformaldehyde, trioxane and hexamethylenetetramine have also been used for this purpose
• phenols have been used to prepare these known novolaks
• Such phenols include cresols, xylenols, biphenols, catechols, hydroquinones, naphthols and the like, including mixtures of the same
• Certain phenols are chosen to impart specific properties, such as varying the softening temperature, water solubility or insolubility, color and melt viscosity
• Certain phenols used to prepare these known novolaks contain two or more adjacent hydroxyl groups Such phenols include pyrogallol, catechol, tannic acid, gallic acid and the like
• the phenols which have adjacent or vicinal hydroxyl groups are known to be metal chelators Metals such as iron, copper, manganese, vanadium, and others form complexes with these types of phenols (See S Yariv,
• novolak resins include coatings, adhesives, fiber bonding abrasives, laminates, foundry resins, friction materials, molding materials and wood composites Certain known novolaks have been used as adhesion promoters for epoxy resins
• U.S. Patent 3,304,276 (Faulkner and O'Neill) describes the preparation and use of metal-reactive polyhydric phenol-modified short oil and long oil alkyds that cure even at room temperature to form rust inhibiting, essentially non-blistering, durable finishes on unoxidized iron and steel surfaces
• the polyhydric phenols include tannins, methyl gallate, propyl gallate, catechol and pyrogallol
• U S. Patent No. 4,340,716 (Hata c/ ⁇ /.) and Japanese J5 6,149,716 teach that good coating compositions showing good adherence and good anticorrosive properties can be prepared by combining (A) a prepolymer of epoxy resin and polyhydroxyphenolic compound with (B) an organic hardener for epoxy resins
• the prepolymer (A) is prepared by prereacting small amounts of polynuclear adjacent aromatic hydroxyl-containing compounds, including catechol and pyrogallol novolaks with epoxies
• the reaction ratio of the epoxy resin and the polyhydric phenolic compound is 1 0/0 05 to 1 0/0 1 (mole/mole)
• U S Patent Nos 4,560,732 and 4,530,947 teach a laquer-type coating composition for metals that forms chelate bonds with the metal to provide strong adhesion to the metal.
• This solvated coating composition comprises the reaction product of epoxy resins and polynuclear polyhydroxyphenols, including catechol and pyrogallol novolaks These reaction products have M consult values of 12,000 to 3 1 ,000 and are prepared at ratios insuring that unreacted adjacent aromatic hydroxyls are available These coatings are applied as lacquers and are unsuitable for making powder coatings because the dried out resins will not melt flow adequately SUMMARY OF THE INVENTION
• novel novolak compound(s) can be used, for example to enhance the adhesion of epoxy resin to metal substrates under typical powder coating conditions.
• One aspect ofthe invention relates to a novel compound(s) ofthe formula:
• R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of —OH, — SH, —H, C,. 2 o alkyl, — ⁇ — Cl, — Br, —I, alkoxy, aryl, alkaryl, and alkenyl groups;
• R 1 , R 2 , R 3 , R 4 , and R 5 are selected such that at least two vicinal groups selected from the group consisting of — OH, — SH, and combinations thereof are present on a ring structure to which R 1 , R 2 , R 3 , R 4 , and R 5 are attached; one ofthe groups selected from the group consisting of R 6 , R 7 , and R 9 are — OH or — SH and the remainder ofthe groups selected from the group consisting of R 6 , R 7 , and R 9 are selected independently from the group consisting of — H, C ⁇ .
• R 8 is selected from the group consisting of C ]-2 o alkyl, — H, — F, — Cl, — Br, — I, alkoxy, aryl, alkaryl, and alkenyl groups;
• R 8 is selected from the group consisting of C ]-2 o alkyl, — H, — F, — Cl,
• R 1 ' is selected from the group consisting of — OH and — SH
• R 10 and R 12 are each independently selected from the group consisting of —OH, — SH, — H, Cue alkyl, — F, — Cl, — Br, — 1, alkoxy, aryl, alkaryl, and alkenyl groups, wherein at least one of R 10 and R 12 is —OH or — SH
• R ⁇ is selected from the group consisting of — H, C )-20 alkyl, — OH, — SH, — F, — Cl, — Br, — I, alkoxyl, aryl, alkaryl, and alkenyl groups
• one ofthe groups selected from R 14 , R 15 , and R 17 are — OH or — SH and the remainder ofthe groups selected from the group consisting of R 14 , R 15 , and R 17 are independently
• R lif , R 19 , R 2() , R ?1 , and R 22 are each independently selected from the group consisting of —OH, — SH, — H, C,.
• R ⁇ s , R l ' ⁇ R 20 , R 21 , and R 22 are selected such that at least two vicinal groups selected from the group consisting of — OH, — SH, and combinations thereof are present on a ring structure to which R 18 , R 19 , R 20 , R 21 , and R 22 are attached; and n is an integer of zero or greater
• the structure of the compound of Formula I is such that
• R 2 , R ⁇ R 20 , and R 2 ' are each independently selected from the group consisting of — OH and — SH
• R 1 , R 4 , R ⁇ R I S , R 10 , and R 22 are each independently selected from the group consisting of — H and C ⁇ -2( ⁇ alkyl groups
• R 6 and R 14 are each independently selected from the group consisting of— OH and — SH
• R s and R 16 are each independently selected from the group consisting of
• R 7 , R 9 , R' ⁇ and R 17 each represent — H
• R 11 is selected from the group consisting of — OH and — SH
• R 10 and R 12 are independently selected from the group consisting of — OH
• — SH — H, C ⁇ -20 alkyl, — F, — Cl, — Br, —I, alkoxy, aryl, alkaryl, and alkenyl groups, wherein at least one of R 10 and R 1? is — OFI or — SH, R 1 , is selected from the group consisting of C]. 2 o alkyl, — -H, — F, — Cl, — Br, — I, alkoxy, aryl, alkaryl, and alkenyl groups
• R 19 , and R 211 each represent —OH
• R 1 , R 4 , R 5 , R 7 , R 9 , R 12 , R' ⁇ R 15 , R 17 , R ⁇ ⁇ , R 7 ', and R 22 each represent — H
• R 8 and R 16 each represent — CHi
• the structure of the compound of Formula I is such that n is an integer of 0 to 10 for reasons of improved processability and reduced viscosity Most preferably the structure ofthe compound is such that n is an integer of 0 to 2 for reasons of improved solubility in various epoxy compositions
• the novolaks of the invention are endcapped with polyhydroxyphenols (e g , catechol) containing adjacent hydroxyl groups
• catechol polyhydroxyphenols
• the more reactive phenol generally reacts with the formaldehyde first This gives a disproportionate amount of one phenolic novolak over the other
• the catechol will react preferentially with the formaldehyde since catechol is much more reactive than the alkyl substituted phenol
• the reaction of cresol will be "starved" of formaldehyde This will produce large blocks of catechol/formaldehyde novolak Produc
• n 0 , 1 , 2 ,
• the method of making the preferred novel compound(s) ofthe invention is a two step reaction whereby in the first step, a substituted phenol, (p-cresol, for example) is reacted with an aldehyde (formaldehyde, for example) under basic conditions to form a substituted dimethylolphenol intermediate (also referred to as a bis(hydroxymethyl) phenol intermediate).
• the substituted dimethylolphenol is reacted with a polyhydroxyphenol containing adjacent hydroxyl groups (catechol, for example) under acidic conditions to produce the polyhydroxyphenol (catechol) endcapped novolak compound(s) of the invention
• a polyhydroxyphenol containing adjacent hydroxyl groups catechol, for example
• This two step reaction precludes the preferential reaction of formaldehyde with the polyhydroxyphenol (catechol) (See Reaction Scheme 2 below )
• Another aspect ofthe invention relates to the use ofthe compound(s) ofthe invention as adhesion promoting curing agent(s) in a second composition comprising an epoxy resin
• the novel curable composition comprises
• a preferred novel curable powder coating composition ofthe invention comprises.
• the invention also provides the above composition wherein the curing agent of element (d) is present in an amount from about 1 to about 15 percent by weight
• adheresion promoter refers to a compound which when added to a curable polymer composition will provide enhanced bond strength and durability of that polymer composition when applied to and cured on a metal substrate, particularly when exposed to hot and wet conditions for an extended time.
• curing agent refers to compound(s) having reactive groups which are capable of reacting with epoxy resins under conditions suitable for said reaction and in suitable stoichiometric amounts to from a solid infusible cured matrix DETAILED DESCRIPTION OF THE INVENTION 1 Compound(s) ofthe Invention
• alkoxy gioups include but are not limited to those selected from the group consisting of methoxy, butoxy, propoxy, ethoxy, biphenyloxy, and phenoxy groups
• suitable aryl group include but are not limited to those selected from the group consisting of phenyl, biphenyl, naphthyl, py ⁇ dyl, furyl, pyrryl, thienyl, quinonyl, lmidazoyl, oxazoyl, and thiazoyl groups
• suitable alkaryl groups include but are not limited to those selected from the group consisting of phenethyl benzyl, cumyl, isopropenyl, and phenyhsopropenyl groups
• suitable alkenyl groups include but are not limited to those selected from the group consisting of allyl, cmnamyl, methallyl, vinyl, and styryl groups
• step (b) intimately mixing and reacting, in the presence of an acid catalyst, approximately two molar equivalents of a polyhydroxyphenol (e g catechol or othei adjacent hydroxyl aromatic), either in water or neat, with one molar equivalent of the substituted dimethylolphenol intermediate of step (a) catalyst, and
• an acid catalyst approximately two molar equivalents of a polyhydroxyphenol (e g catechol or othei adjacent hydroxyl aromatic), either in water or neat, with one molar equivalent of the substituted dimethylolphenol intermediate of step (a) catalyst
• Substituted Phenols Generally, a range of properties is obtained when using different substituted phenols in making compounds ofthe invention Suitable substituents include alkyl, alkoxy, aryl, halogen, and other substituents which would not interfere with the reaction For example, phenols substituted with small alkyl groups (Ci to C 9 ) tend to have lower softening points than halo substituted phenols Phenols substituted with larger alkyl groups (C ]0 to C 20 ) tend to have glass transition temperatures (Tg) and softening points lower than phenols substituted with smaller akyl groups The wide variations of substituent groups are used to find the optimum properties ofthe final novolak
• Suitable substituted phenols include but are not limited to those selected from the group consisting of cresols, (ter/)butylphenol, methoxyphenol, phenylphenol, benzylphenol, phenethylphenol, ethylphenol, isopropylphenol, chlorophenol, bromophenol, fluorophenol, mixtures thereof and the like
• Formula 1 include but are not limited to those selected from the group consisting of catechol and substituted catechols
• suitable substituents include alkyl, alkoxy, aryl, halogen, and other substituents which would not interfere with the reaction
• substituents include alkyl, alkoxy, aryl, halogen, and other substituents which would not interfere with the reaction
• Specific examples include methylcatechols, (tert)butylcatechols, ethylcatechols, isopropylcatechols, butylcatechols, (tert)butylcatechols, amylcatechols, (tert)amylcatechols, benzylcatechols, phenethyl catechols, phenylcatechols, fluorocatechols, chlorocatechols, bromocatechols, methoxycatechols, ethoxycatechols, formylcatechols, allylcatechols, orth ⁇ - dihydroxynaphthalen
• aldehydes such as formaldehyde, paraformaldehyde, trioxane, acetaldehyde, glyoxal, butyraldehyde, propionaldehyde, benzaldehyde, furfural, phenylacetaldehyde, chloral, chloroacetaldehyde, dichloroacetaldehyde, mixtures thereof and the like
• suitable acid catalysts useful in making the compound(s) of the invention include but are not limited to those selected from the group consisting of acids such as sulfuric, hydrochloric, phosphoric, methanesulfonic, trifluoromethanesulfonic, trifluoroacetic, formic, oxalic, benzenesulfonic, p- toluenesulfonic, mixtures thereof and the like
• the acid catalyst concentration is typically in a range of about 0.5 to about 20 molar percent of the substituted bis(hydroxymethyl)phenol
• the compound(s) ofthe invention can be used, for example, in coatings, composites, molding compounds, foundry resin compositions and additives to epoxies
• a preferred use ofthe compound(s) ofthe invention are as adhesion promoting curing agents for coating compositions comprising solid epoxy resins
• Epoxy resins useful in compositions of the invention are well-known in the literature Especially preferred are the polyglycidyl ethers of bisphenol A These are available in various epoxy equivalent weights ranging from 170 up to about
• the catalyst used in the composition of the invention should be capable of accelerating the reaction of epoxy groups with epoxy reactive groups
• the epoxy groups are present in the epoxy resin
• the epoxy reactive groups are present in the compound(s) ofthe invention and other curing agents
• the epoxy reactive groups include phenolic groups, which are present in the compound(s) ofthe invention, as well as other groups including anhydrides, primary and secondary amines, thiols, mixtures thereof and the like
• the catalyst also facilitates epoxy/epoxy homopoiymerization Catalysts, unlike curing agents, are not consumed during the reaction
• Suitable catalysts include but are not limited to those selected from the groups consisting of 2-methylimidazole and adducts thereof, 2,4,6- tris(dimethylaminomethyl)phenol, N,N-dimethylbenzylamine, stannous octoate, chromium octoate, cobalt octoate, titanium octoate, zirconium octoate, mixtures thereof and the like
• the catalyst is solid for reasons of improved storage stability of the curing composition.
• Curing Agents are compounds comprising multiple epoxy reactive groups
• epoxy reactive groups can react with the epoxy groups of an epoxy resin to form a solid infusible matrix This reaction is typically accelerated by a catalyst
• the compound(s) of the invention is a curing agent in that it contains phenolic groups which are epoxy reactive and is consumed during an epoxy polymerization Typically other curing agents are used in addition to the compound(s) ofthe invention in order to achieve the desired properties ofthe cured epoxy matrix
• Suitable curing agents other than the compounds ofthe present invention include but are not limited to those selected from the group consisting of primary aliphatic and aromatic amines (such as butylamine, ethylenediamine, aniline, benzylamine, hexamethylenediamine, methylenedianiline, diaminodiphenylsulfone, etc ), secondary aliphatic and aromatic polyamines (such as piperazine, etc ), thiols (such as thiol terminated polyoxyalkylene compounds), anhydrides (such as benzophenonetetracarboxylic acid, dianhydride, trimelitic anhydride, etc ), and oxazolines (such as phenylenebisoxazoline, etc ) and mixtures thereof
• primary aliphatic and aromatic amines such as butylamine, ethylenediamine, aniline, benzylamine, hexamethylenediamine, methylenedianiline, diaminodiphenylsul
• the curing agents arc solid
• preferred solid curing agents for epoxy powder coating compositions are those selected from the group consisting of solid bisphenolic terminated epoxy resin, solid bisphenols, and dicyandiamide
• the curing agent is present in an amount from about 1 to about 30 percent by weight based on the total weight of the epoxy resin, compound(s) of the invention, catalyst, and curing agent
• the curable composition of the invention optionally further comprises a hygroscopic solvent for applications other than powder coatings
• the hygroscopic solvent serves to remove any water present from the surface of an intended metal substrate Alternatively and/or in addition, the metal substrate can be heated to about 150°C or greater, preferably about 180°C or greater to remove surface water
• suitable hygroscopic solvents include but are not limited to those selected from the group consisting of acetone, methylethyl ketone, tetrahydrofuran, ethylacetate, Ci to C 4 alcohols, mixtures thereof and the like
• the curable composition of the invention can optionally further comprise a flow control agent
• suitable flow control agents include but are not limited to those selected from the group consisting of low molecular weight polyacrylate polymers such as Modaflo IM and Modaflo 1 M III from Monsanto and fluorochemicals such as FluoradTM FC430 from 3M Company
• the curable composition of the invention can optionally further comprise a filler
• suitable fillers include but are not limited to those selected from the group consisting of wollastonite, calcium carbonate, clays, feldspar and silica
• the curable composition of the invention can optionally further comprise a colorant such as pigments and toners
• suitable colorants include but are not limited to those selected from the group consisting of rutile and anatase titanium dioxide, iron oxides, chrome oxides, phthalocyanine green and phthalocyanine blue
• the present invention also provides articles coated with the cured or uncured compositions of the invention For example a metal substrate such as iron or steel may be coated with the compositions of the invention
• reaction mixture was added 33 g (0 37 moles) of oxalic acid
• the reaction mixture slowly increased in temperature to 60°C and then leveled off
• the temperature ofthe reaction mixture was increased to 65°C, then allowed to slowly exotherm to 80°C over 20 minutes
• the reaction contents were held at 80°C for 15 minutes
• the product began to separate from the water
• the reaction mixture was heated to 95°C and held at this temperature for 3 hours
• reaction mixture remained clear
• the reaction mixture was cooled to 25°C and then neutralized with glacial acetic acid to precipitate the reaction product
• the reaction product was further diluted with water and stirred, then vacuum filtered
• the product cake was rinsed several times with water, then transferred to a tray and spread out to dry in a stream of air A beige solid was recovered.
• reaction mixture remained clear
• the reaction mixture was cooled to 25°C and neutralized with glacial acetic acid to precipitate the reaction product
• the reaction product was further diluted with water and stirred to uniformity, then vacuum filtered
• the product was rinsed several times with water, then transferred to a tray and spread out to dry in a stream of air
• a beige-tan solid was recovered 322 g (88% yield) of crude 2,6-dimethylol-4-ethylphenol product was isolated
• Example 7 Preparation of catechol-(p-cresol) novolak To a 3 liter, 3 necked round bottomed flask equipped with a paddle stirrer, condenser, thermometer and heating source, were added 542 g (5 moles) of p- cresol followed by 300 ml of water To this heterogeneous mixture were added 800 g of 25% aqueous NaOH The solution was stirred and cooled to 40°C To this mixture were added 832 g (10.25 moles) of 37% formaldehyde The temperature ofthe reaction mixture increased to 50°C, and was kept from rising further by using an ice-water cooling bath Within 30 minutes, the product precipitated as the sodium salt The reaction mixture was allowed to stir at 50°C for 18 hours The reaction mixture was cooled to 40°C and neutralized with glacial acetic acid to precipitate the reaction product Water was added to the reaction product and the product was vacuum filtered The product cake was further slurried with clean water and vacuum filtered again It was placed into an aluminum tray and
• the materials in the amounts indicated in Table 1 were weighed together in a one gallon can and ground to a coarse powder
• the dry mixture was sealed in the can and mixed on a paint shaker for 15 minutes
• the dry mixture was then fed into a co-rotating twin screw extruder having a 15 mm bore and a length to diameter ratio of 15 1 available from APV Corporation Prior the this extrusion, the extruder was purged with EponTM 2004
• the feed rate ofthe extruder was set at 0 91 kg/hour and had an output temperature of 105 - 1 10° C
• the extrudate was collected off of a quench roll, air cooled and milled using a hammer mill or other similar milling apparatus
• the milled powder was sieved through a No 70 mesh sieve and a powder having a nominal average particle size of about 40-50 microns was obtained Cab-O-SilTM M5 (Cabot Corp ) was then incorporated (0 35% by weight ofthe powder formulation) as a fluid
• Example 8 The procedure for Example 8, outlined above, was followed however 4 0 g of Durite '1 M SD171 1 phenolic novolak from Borden Chemical Co was substituted for the catechol cresol novolak
• the coatings were prepared by first dessicating the powders in a vacuum chamber evacuated to 5 mm of Hg for 24 hours The powder to be coated was then placed in a fluidized bed and hot rolled steel panels (88 9 mm (3 5 in) x 88 9 mm (3 5 in) x 6 4 mm (0 25 in)) which were induction heated to about 220°C were introduced into the fluidized bed and coated by the powder to a coating thickness of approximately 0 48 mm (19 mils) Two panels were prepared with each coating formulation The panels were post cured after coating for 2 minutes in a 204°C oven After cooling, each panel was constructed into a cathodic disbondment test cell and the cathodic disbondment resistance ofthe coated and cured powder coatings was measured in accordance with ASTM A934/A934M annex, Test Method Al 2 2 1 Test A with reference to ASTM G95-87 The noted procedural modifications included the size of the test panels (88 9 x 88 9 x 6 4 mm hot rolled steel),

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• Chemical Kinetics & Catalysis (AREA)
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• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Epoxy Resins (AREA)
• Phenolic Resins Or Amino Resins (AREA)
• Paints Or Removers (AREA)

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