WO2001005901A1 - Curable composition - Google Patents
Curable composition Download PDFInfo
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- WO2001005901A1 WO2001005901A1 PCT/EP2000/006423 EP0006423W WO0105901A1 WO 2001005901 A1 WO2001005901 A1 WO 2001005901A1 EP 0006423 W EP0006423 W EP 0006423W WO 0105901 A1 WO0105901 A1 WO 0105901A1
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- WIPO (PCT)
- Prior art keywords
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Classifications
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- 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
-
- 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
- C08L63/10—Epoxy resins modified by unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- 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
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
- C09D5/033—Powdery paints characterised by the additives
Definitions
- the invention relates to a curable composition based on acidic polyesters and on certain polyglycidyl compounds and to a powder coating composition based thereon.
- JP-A-Sho 57-108166 discloses a curable composition and the use thereof as a powder coating composition, the composition comprising
- (C) from 1 to 20 parts by weight of a further epoxy resin, which may be, inter alia, diglycidyl terephthalate or trigiycidyl isocyanurate, and
- component (B) polymers or copoiymers that contain identical or different structural repeating units of formula (I):
- radicals R and R 2 are each independently of the other a hydrogen atom or a methyl group.
- the said compositions contain at least approximately 2.5 % by weight of component (B), based on the total amount of components (A), (B) and (C).
- component (B) based on the total amount of components (A), (B) and (C).
- the fiow behaviour of the compositions is generally still not satisfactory, however, and accordingly when such comDositions are used in the production of powder resin coatings there is, in particular, a risk that the known orange-peel effect will occur, that is to say, that a coating having a very uneven surface will be formed.
- the present invention is based on the surprising discovery that the flow behaviour of the above-mentioned curable compositions is substantially improved but, nevertheless, cured material having excellent physical properties, especially excellent mechanical properties, is obtainable by using as component (B) of the compositions a maximum of 2 percent by weight, based on the total amount of components (A), (B) and (C), of one or more polymers or copoiymers that each have an epoxy value of at least 3 equivalents per kilogram and a molecular weight (number average Mn) of from 800 to 20 000 and that contain identical or different structural repeating units of the formula (I) already mentioned above.
- the present invention accordingly relates to a curable composition
- a curable composition comprising:
- (A) from 80 to 97.9 percent by weight, based on the total amount of components (A), (B) and (C), of a polyester component having an acid number in total of from 10 to 40 mg of KOH per gram of the component and consisting of one or more polyesters containing free carboxyl groups;
- (B) from 0.2 to 2 percent by weight, based on the total amount of components (A), (B) and (C), of a component consisting of one or more polymers or copoiymers that each have an epoxy value of at least 3 equivalents per kilogram and a molecular weight (number average Mn) of from 800 to 20 000 and that contain identical or different structural repeating units of formula (I):
- R 1 and R 2 are each independently of the other a hydrogen atom or a methyl group; and (C) a component consisting of one or more monomeric polyglycidyl compounds having an epoxy value of at least 3.5 equivalents per kilogram and a maximum molecular weight of 600, the amount of component (C) in percent by weight, based on the total amount of components (A), (B) and (C), corresponding to the difference between 100 and the sum of the percentage amounts of components (A) and (B) based on the total amount of components (A), (B) and (C); and (D) an accelerator for the reaction of epoxy groups with carboxyl groups, wherein, furthermore, component (B) constitutes from 5 to 95 percent of the total weight of components (B) and (C) and the molar ratio of glycidyl groups to carboxyl groups in the composition is from 1.3:1 to 1 :1.3.
- Curable compositions according to the present invention are distinguished, inter alia, by a very good flow behaviour and yield a cured material that has a high crosslinking density and excellent mechanical properties.
- curable compositions according to the invention are suitable, for example, as adhesives, casting resins or compression-moulding compositions, it being possible for further components that are conventional in the field of use in question to be admixed therewith, as desired.
- powder coating compositions that contain as curable component system the compositions according to the invention.
- the invention accordingly relates also to powder coating compositions based on the curable compositions according to the invention.
- the polyester component (A) constitutes preferably from 85 to 96 percent by weight, especially from 88 to 95 percent by weight, of the composition according to the invention based on the total amount of components (A), (B) and (C).
- the acid number of from 10 to 40 mg of KOH per gram applies to the polyester component as a whole, and therefore corresponds, when several different polyesters are used, to the average acid number of the totality of those polyesters.
- the polyesters of component (A) are advantageously solid at room temperature (from 15 to 35°C) and have, for example, a molecular weight (number average Mn) of from 1000 to 10000.
- the ratio of Mw (weight average of the molecular weight) to Mn of those polyesters is generally from 2 to 10.
- free-carboxyl-group-containing polyesters having a molecular weight (weight average Mw from GPC measurement using polystyrene calibration) of from 4000 to 15 000, especially from 6500 to 11 000, and a glass transition temperature (Tg) of from 35 to 120°C, preferably from 50 to 90°C
- Polyesters such as those mentioned are described, for example, in US-A-3 397254 and EP- A-0 600 546.
- Polyesters suitable for the present invention are condensation products of difunctional, trifunctional and/or polyfunctional alcohols (polyols) with dicarboxylic acids and, optionally, trifunctional and/or polyfunctional carboxylic acids, or with corresponding carboxylic acid anhydrides.
- the polyols used include, for example, ethylene glycol, diethylene glycol, the propylene glycols, butylene glycol, 1 ,3-butanediol, 1 ,4-butanediol, neopentanediol, isopentyl glycol, 1 ,6-hexanediol, glycerol, hexanetriol, trimethylolethane, trimethylolpropane, erythritol, pentaerythritol, cyclohexanediol and 1 ,4-dimethylolcyclo- hexane.
- Suitable dicarboxylic acids include, for example, isophthalic acid, terephthalic acid, phthalic acid, methyl-substituted derivatives of the said acids, tetrahydrophthalic acid, methyl- tetrahydrophthalic acids, for example 4-methyltetrahydrophthalic acid, cyclohexane- dicarboxylic acids, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedicarboxylic acid, fumaric acid, maleic acid and 4,4'-diphenyl- dicarboxylic acid etc..
- Suitable tricarboxylic acids include, for example, aliphatic tricarboxylic acids, such as 1 ,2,3-propanetricarboxylic acid, aromatic tricarboxylic acids, such as trimesic acid, trimellitic acid and hemimellitic acid, and cycloaliphatic tricarboxylic acids, such as 6-methylcyclohex-4-ene-1 ,2,3-tricarboxylic acid.
- Suitable tetracarboxylic acids include, for example, pyromellitic acid and benzophenone-3,3',4,4'-tetracarboxylic acid.
- polyesters especially are very commonly based on neopentyl glycol and/or trimethylolpropane as the main alcoholic monomer constituent(s) and on adipic acid and/or terephthalic acid and/or isophthalic acid and/or trimellitic acid as the main acidic monomer component(s).
- Component (B) constitutes preferably from 0.7 to 2 percent by weight, especially from 0.7 to 1.8 percent by weight, of the composition according to the invention based on the total weight of components (A), (B) and (C). It is furthermore preferred for component (B) to constitute from 5 to 50 percent, especially from 7.5 to 25 percent, of the total weight of the polyglycidyl components (B) and (C).
- the polymers and copoiymers constituting component (B) of the compositions according to the invention preferably have a molecular weight (number average Mn) of from 1000 to 10 000.
- the polymers and copoiymers can be prepared, for example, by a conventional free- radical polymerisation of a monomer selected from glycidyl acrylate, glycidyl methacrylate, ⁇ - methylglycidyl acrylate and ⁇ -methylglycidyl methacrylate, optionally in the presence of a suitable amount of free-radically polymerisable comonomer(s).
- the polymerisation can be carried out, for example, by dissolving the monomers in a suitable organic solvent, such as toluene, 1-methoxy-2-propanol, 1 -methoxy-2-propyl acetate or methyl isobutyl ketone, or in a mixture of the said solvents, and heating the resulting solution in the presence of a suitable initiator, such as, for example, ⁇ , ⁇ '-azoisobutyronitrile or dicumyl peroxide, optionally in the presence of a chain terminator, such as, for example, allyl glycidyl ether.
- a suitable organic solvent such as toluene, 1-methoxy-2-propanol, 1 -methoxy-2-propyl acetate or methyl isobutyl ketone
- a suitable initiator such as, for example, ⁇ , ⁇ '-azoisobutyronitrile or dicumyl peroxide
- a chain terminator such as, for
- Suitable comonomers include, for example, (meth)acrylic acid esters, such as ethyl acrylate, butyl acrylate, 2-ethyl hexylacrylate, and also, especially, d-C 4 alkyl methacrylates, such as methyl methacrylate, ethyl methacrylate and butyl methacrylate, and furthermore, for example, acrylo- and methacrylo-nitriles, (meth)acrylamides and also vinyl compounds, for example aromatic vinyl compounds, especially styrene and styrene derivatives.
- (meth)acrylic acid esters such as ethyl acrylate, butyl acrylate, 2-ethyl hexylacrylate
- d-C 4 alkyl methacrylates such as methyl methacrylate, ethyl methacrylate and butyl methacrylate
- vinyl compounds for example aromatic vinyl compounds, especially styrene and
- Component (B) consists preferably of polymers or copoiymers each having an epoxy value of at least 5 equivalents per kilogram.
- component (B) is constituted by polymers that consist substantially of identical or different structural repeating units of formula (I):
- the polyglycidyl component (C) constitutes preferably from 0.1 to 38 percent by weight, especially from 5 to 15 percent by weight, of the composition according to the invention based on the total amount of components (A), (B) and (C).
- Component (C) consists of one or more polyglycidyl or poly( ⁇ -methyl)glycidyl compounds each having an epoxy value of at least 3.5 equivalents per kilogram.
- Those compounds in contrast to the polyglycidyl compounds constituting component (B) of the compositions according to the invention, are monomeric compounds having a maximum molecular weight of 600 (molecular weight being understood in this case to mean the sum, calculated theoretically for each of the compounds, of the weights of the atoms of the molecule), for example corresponding diglycidyl or triglycidyl compounds that are preferably solid at room temperature, or corresponding polyglycidyl compounds having an even larger number of glycidyl groups per molecule.
- component (C) of the compositions consists of one or more glycidyl compounds having an epoxy value of at least 4 equivalents, especially at least 5 equivalents, per kilogram.
- the epoxy value of components (B) and (C) together likewise to be at least 3.5 equivalents, preferably at least 5 equivalents, per kilogram of the mixture of the two components.
- compositions according to the invention preferably have a slight molar excess of epoxy groups.
- the molar ratio of glycidyl groups to carboxyl groups in the compositions is thus preferably from 1.3:1 to 1 :1 , for example approximately from 1.2:1 to 1.1 :1.
- compositions according to the invention also contain, as component (D), a catalyst for the reaction of epoxy groups with carboxyl groups.
- a catalyst for the reaction of epoxy groups with carboxyl groups is frequently an organic amine or a derivative of an amine, especially a tertiary amine or a nitrogen-containing heterocyclic compound.
- Preferred catalysts for the reaction of epoxy groups with carboxyl groups are phenylimidazole, N- benzyldimethylamine and 1 ,8-diazabicyclo[5.4.0]-7-undecene, optionally on a silicate support or triphenylphosphine, Actiron ® NXJ-60 (2-propylimidazole), Actiron ® NXJ-60 P (60 % by weight of 2-propylimidazole on 40 % by weight of solid support), Beschreiber ® DT 3126 ([Ci 6 H 33 N(CH 3 ) 3 ] + Br " ).
- the catalyst or a catalyst mixture is preferably added in such an amount that the gel time of the mixture at 180°C (determined according to DIN 55990) is approximately from 70 to 400 seconds, preferably from 90 to 300 seconds. Generally, approximately from 0.1 to 10 percent by weight, especially from 0.5 to 5 percent by weight, of catalyst will be required for that purpose.
- some commercially available polyesters that are used as a constituent of component (A) of the compositions according to the invention will already contain a certain amount of one of the above-mentioned catalysts or of a comparable catalyst, and that amount should be taken into account in the above percentage by weight figure for catalyst; the mentioned preferred gel times can be used to provide an indication of how much catalyst still needs to be added.
- compositions according to the invention may, of course, contain further components, which may vary according to the field of application of the compositions and which will be known to the person skilled in the art in question.
- Powder coating compositions based on the compositions according to the invention may, for example, also contain additives customary in the surface-coating industry in the amounts conventionally used therefor, such as, inter alia, light stabilizers, curing accelerators, dyes, pigments, for example titanium dioxide pigment, degassing agents, for example benzoin, and also additional flow agents.
- Suitable flow agents include, for example, polyvinyl acetals, such as polyvinyl butyral, polyethylene glycol, polyvinylpyrrolidone, glycerol and acrylic mixed polymers, such as, for example, those available under the names Modaflow ® and Acrylron ® .
- the powder coating compositions according to the invention can be prepared simply by mixing the constituents together, for example in a ball mill.
- Another, more preferred possibility comprises melting together, blending and homogenising the constituents, preferably using an extrusion machine, such as a Buss co-kneader, and cooling and comminuting the resulting mass.
- an extrusion machine such as a Buss co-kneader
- the powder coating mixtures preferably have a particle size in the range from 0.015 to 500 ⁇ m, especially from 10 to 75 ⁇ m.
- a masterbatch from portions of the binder, the epoxy resins and, optionally, further components, the masterbatch then being mixed and homogenised in a second step with the remainder of the binder and the remaining constituents to yield the finished powder coating composition.
- the powder coating compositions are cured at a temperature of at least approximately 100°C, preferably at from 150 to 220°C. Curing generally takes approximately from 5 to 60 minutes. All materials that are stable at the temperatures required for the curing, especially ceramics and metals, are suitable for coating.
- the substrate may already have one or more base surface-coatings that are compatible with the powder coating composition.
- the free-radical polymerisation is carried out using AIBN ( ⁇ , ⁇ '-azoisobutyronitrile) as initiator.
- the desired low molecular weight (M w or M n ) is achieved by selecting the amount of initiator, the amount of chain terminator (allyl glycidyl ether in the present case) and the polymerisation temperature.
- the major portion of the monomer mixture (90 %), the full amount of initiator and the major portion of the solvent are metered within a period of two hours into an initial charge in the reactor, the initial charge consisting of the remainder of the monomer mixture (10 %) and the remainder of the solvent.
- This allows good control of the polymerisation exotherm and helps to achieve a molecular weight that is reproducible.
- Many variants of the reaction procedure are, of course, possible; the person skilled in the art will find that it is simple to determine suitable conditions.
- the polymerisation apparatus consists of a heatable 3000 ml double-walled jacket reactor with stirrer, reflux condenser, thermometer, nitrogen purging means, feed receptacle and feed pump ("Masterflex" peristaltic pump).
- a monomer mixture consisting of 1300.50 g of methacrylic acid glycidyl ester and 144.50 g of allyl glycidyl ether is prepared.
- the reactor is charged with 144.50 g of the monomer mixture and 867.00 g of methoxypropyl acetate (MPA, solvent).
- the feed receptacle is filled with the remainder of the monomer mixture (1300.50 g), 96.50 g of MPA and 72.25 g of AIBN.
- the AIBN should be homogeneously dissolved.
- the entire apparatus (including the feed receptacle) is rendered inert with nitrogen, the reactor is heated to an internal temperature of 100°C (jacket temperature of 105°C) and the feed is then started.
- the rate of feed is so selected that the feed takes about 2 hours.
- the stirring speed is 100 revs/min.
- polymerisation is continued for a further 2 hours at 100°C under nitrogen.
- the viscous solution is precipitated in hexane and the solvent is decanted off.
- the greasy residue is dissolved in acetone and precipitated from water.
- the precipitation residue is reprecipitated once more from acetone/water.
- the solid polymer is filtered off and dried in vac ⁇ o. 1200.00 g of colourless polymer in powder form, having the following analytical data, remain:
- Monomer mixture 144.50 g of glycidyl methacrylate + 25.50 g of allyl glycidyl ether
- Monomer mixture 25.50 g of butyl methacrylate + 127.50 g of glycidyl methacrylate +
- DGT diglycidyl terephthalate
- GMA glycidyl methacrylate
- the two flasks are connected to each other.
- the flat ground flask is heated by means of an oil bath until the DGT has melted.
- the 1 litre flat ground flask together with the 250 ml supply flask connected to it, is evacuated and filled with nitrogen a total of five times.
- the mixture of GMA and 1 ,1-bis(tert-butylperoxy)-3,3,5- trimethylcyclohexane is then fed from the 250 ml supply flask into the molten DGT within a period of 20 minutes, with stirring, and the batch is left to react for 3.5 hours with further stirring. On subsequent cooling, the liquid mass solidifies. Yield: 236 g (98%)
- Table 1b Powder coating composition formulations H to K and P according to the invention
- the powder coating compositions are applied to Q panels as substrate.
- the coated panels are then placed in an oven in order to melt and fully cure the powder coating composition.
- the gel time, the curing temperature and the curing time, and also the thickness of the resulting powder resin coating are indicated in the following Tables 2a and 2b together with properties of the resulting coatings that are important from the standpoint of surface-coating technology.
- Table 2a Properties, important from the standpoint of surface-coating technology, of the coatings obtained using compositions A, B, C and E, F, G
- the impact deformation is determined by dropping onto the coated face a punch weighing 2 kg, having a 20 mm diameter ball on its underside, with the underside leading, from a specific height from behind (reverse side) or from the front.
- the value indicated is the product of the weight of the punch in kg and the test height in cm at which there is still no detectable damage to the coating.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020017016787A KR20020018685A (en) | 1999-07-14 | 2000-07-06 | Curable composition |
BR0013164-4A BR0013164A (en) | 1999-07-14 | 2000-07-06 | Curable composition |
JP2001511122A JP2003505531A (en) | 1999-07-14 | 2000-07-06 | Curable composition |
PL00352938A PL352938A1 (en) | 1999-07-14 | 2000-07-06 | Curable composition |
MXPA02000341A MXPA02000341A (en) | 1999-07-14 | 2000-07-06 | Curable composition. |
EP00954442A EP1196508A1 (en) | 1999-07-14 | 2000-07-06 | Curable composition |
CA002378191A CA2378191A1 (en) | 1999-07-14 | 2000-07-06 | Curable composition |
AU66898/00A AU6689800A (en) | 1999-07-14 | 2000-07-06 | Curable composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1304/99 | 1999-07-14 | ||
CH130499 | 1999-07-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001005901A1 true WO2001005901A1 (en) | 2001-01-25 |
Family
ID=4207317
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/006423 WO2001005901A1 (en) | 1999-07-14 | 2000-07-06 | Curable composition |
Country Status (12)
Country | Link |
---|---|
EP (1) | EP1196508A1 (en) |
JP (1) | JP2003505531A (en) |
KR (1) | KR20020018685A (en) |
CN (1) | CN1360619A (en) |
AU (1) | AU6689800A (en) |
BR (1) | BR0013164A (en) |
CA (1) | CA2378191A1 (en) |
HU (1) | HUP0201962A2 (en) |
MX (1) | MXPA02000341A (en) |
PL (1) | PL352938A1 (en) |
TR (1) | TR200200040T2 (en) |
WO (1) | WO2001005901A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10294388B2 (en) | 2011-02-07 | 2019-05-21 | Swimc Llc | Compositions for containers and other articles and methods of using same |
US10435199B2 (en) | 2012-08-09 | 2019-10-08 | Swimc Llc | Compositions for containers and other articles and methods of using same |
US10745514B2 (en) | 2014-04-14 | 2020-08-18 | Swimc Llc | Methods of preparing compositions for containers and other articles and methods of using same |
US11130881B2 (en) | 2010-04-16 | 2021-09-28 | Swimc Llc | Coating compositions for packaging articles and methods of coating |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4274211B2 (en) * | 2006-08-24 | 2009-06-03 | Basfコーティングスジャパン株式会社 | Resin composition for paint and paint composition using the same |
CN105176169A (en) * | 2015-10-31 | 2015-12-23 | 安徽神剑新材料股份有限公司 | Epoxy-terminated powder paint curing agent and synthesis method thereof |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4242253A (en) * | 1979-06-04 | 1980-12-30 | E. I. Du Pont De Nemours And Company | Low gloss powder coating compositions |
JPS57108166A (en) * | 1980-12-25 | 1982-07-06 | Dainippon Ink & Chem Inc | Resin composition for powder paint |
JPH01313573A (en) * | 1988-06-10 | 1989-12-19 | Nippon Oil & Fats Co Ltd | Powder coating composition |
JPH037757A (en) * | 1989-11-07 | 1991-01-14 | Toray Ind Inc | Polyester resin composition for molding |
EP0600546A1 (en) * | 1992-12-01 | 1994-06-08 | Dsm N.V. | Binder composition for powder paints |
-
2000
- 2000-07-06 EP EP00954442A patent/EP1196508A1/en not_active Withdrawn
- 2000-07-06 JP JP2001511122A patent/JP2003505531A/en active Pending
- 2000-07-06 BR BR0013164-4A patent/BR0013164A/en not_active IP Right Cessation
- 2000-07-06 MX MXPA02000341A patent/MXPA02000341A/en unknown
- 2000-07-06 HU HU0201962A patent/HUP0201962A2/en unknown
- 2000-07-06 CN CN00810254A patent/CN1360619A/en active Pending
- 2000-07-06 TR TR2002/00040T patent/TR200200040T2/en unknown
- 2000-07-06 PL PL00352938A patent/PL352938A1/en not_active Application Discontinuation
- 2000-07-06 AU AU66898/00A patent/AU6689800A/en not_active Abandoned
- 2000-07-06 KR KR1020017016787A patent/KR20020018685A/en not_active Application Discontinuation
- 2000-07-06 WO PCT/EP2000/006423 patent/WO2001005901A1/en not_active Application Discontinuation
- 2000-07-06 CA CA002378191A patent/CA2378191A1/en not_active Abandoned
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4242253A (en) * | 1979-06-04 | 1980-12-30 | E. I. Du Pont De Nemours And Company | Low gloss powder coating compositions |
JPS57108166A (en) * | 1980-12-25 | 1982-07-06 | Dainippon Ink & Chem Inc | Resin composition for powder paint |
JPH01313573A (en) * | 1988-06-10 | 1989-12-19 | Nippon Oil & Fats Co Ltd | Powder coating composition |
JPH037757A (en) * | 1989-11-07 | 1991-01-14 | Toray Ind Inc | Polyester resin composition for molding |
EP0600546A1 (en) * | 1992-12-01 | 1994-06-08 | Dsm N.V. | Binder composition for powder paints |
Non-Patent Citations (3)
Title |
---|
DATABASE WPI Section Ch Week 198232, Derwent World Patents Index; Class A14, AN 1982-67201E, XP002153114 * |
DATABASE WPI Section Ch Week 199005, Derwent World Patents Index; Class A21, AN 1990-034454, XP002153115 * |
DATABASE WPI Section Ch Week 199108, Derwent World Patents Index; Class A23, AN 1991-055800, XP002153116 * |
Cited By (9)
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US11130881B2 (en) | 2010-04-16 | 2021-09-28 | Swimc Llc | Coating compositions for packaging articles and methods of coating |
US10294388B2 (en) | 2011-02-07 | 2019-05-21 | Swimc Llc | Compositions for containers and other articles and methods of using same |
US11053409B2 (en) | 2011-02-07 | 2021-07-06 | Jeffrey Niederst | Compositions for containers and other articles and methods of using same |
US11634607B2 (en) | 2011-02-07 | 2023-04-25 | Swimc Llc | Compositions for containers and other articles and methods of using same |
US10435199B2 (en) | 2012-08-09 | 2019-10-08 | Swimc Llc | Compositions for containers and other articles and methods of using same |
US10894632B2 (en) | 2012-08-09 | 2021-01-19 | Swimc Llc | Compositions for containers and other articles and methods of using same |
US11628974B2 (en) | 2012-08-09 | 2023-04-18 | Swimc Llc | Compositions for containers and other articles and methods of using same |
US10745514B2 (en) | 2014-04-14 | 2020-08-18 | Swimc Llc | Methods of preparing compositions for containers and other articles and methods of using same |
US11525018B2 (en) | 2014-04-14 | 2022-12-13 | Swimc Llc | Methods of preparing compositions for containers and other articles and methods of using same |
Also Published As
Publication number | Publication date |
---|---|
CN1360619A (en) | 2002-07-24 |
JP2003505531A (en) | 2003-02-12 |
EP1196508A1 (en) | 2002-04-17 |
HUP0201962A2 (en) | 2002-09-28 |
BR0013164A (en) | 2002-04-09 |
KR20020018685A (en) | 2002-03-08 |
AU6689800A (en) | 2001-02-05 |
TR200200040T2 (en) | 2002-12-23 |
CA2378191A1 (en) | 2001-01-25 |
MXPA02000341A (en) | 2002-07-02 |
PL352938A1 (en) | 2003-09-22 |
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