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WO2006018236A1 - Masse de revetement thermodurcissable, son utilisation et procede pour produire des laques en poudre - Google Patents

Masse de revetement thermodurcissable, son utilisation et procede pour produire des laques en poudre Download PDF

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Publication number
WO2006018236A1
WO2006018236A1 PCT/EP2005/008767 EP2005008767W WO2006018236A1 WO 2006018236 A1 WO2006018236 A1 WO 2006018236A1 EP 2005008767 W EP2005008767 W EP 2005008767W WO 2006018236 A1 WO2006018236 A1 WO 2006018236A1
Authority
WO
WIPO (PCT)
Prior art keywords
coating composition
thermosetting coating
composition according
fatty acid
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2005/008767
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German (de)
English (en)
Inventor
Michael Kraus
Andreas Kaplan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EMS Chemie AG
Original Assignee
EMS Chemie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EMS Chemie AG filed Critical EMS Chemie AG
Priority to EP05770396A priority Critical patent/EP1778806A1/fr
Publication of WO2006018236A1 publication Critical patent/WO2006018236A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides

Definitions

  • Thermosetting coating composition its use and process for producing powder coatings
  • thermosetting coating compositions comprising a carboxyl-functional polyester which is prepared by a condensation reaction of aliphatic and / or cycloaliphatic and / or aromatic polycarboxylic acids and anhydrides, a ⁇ -hydroxyalkylamide with the addition of certain additives or impact modifiers.
  • Powder coatings which contain carboxyl-functional polyesters and ⁇ -hydroxyalkylamides as binders have been known for some time.
  • No. 4,801,680 describes powder coatings based on carboxyl-functional polyesters and .beta.-hydroxyalkylamides, where the polyester has a Tg in the range from 30.degree. C. to 85.degree. C. and the equivalent ratio of .beta.-hydroxyalkylamide equivalents to carboxylic acid equivalents Range from 0.6: 1 to 1.6: 1. lies.
  • Toxicologically harmless powder coatings based on carboxyl-functional polyesters and .beta.-hydroxyalkylamides in addition to excellent mechanical properties, also have very good weathering stability and are therefore suitable for use in outdoor areas.
  • the coating composition according to the invention consists of: A) a carboxyl-functional polyester prepared by a condensation reaction of aliphatic and / or cycloaliphatic and / or aromatic polycarboxylic acids and anhydrides, the Polyes ⁇ ter a Tg in the range of 30 ° C to 80 ° C and an acid number of about 20 to 100 mg KOH / g, and
  • fatty acid esters of sugars are used whose fatty acid radicals contain 2 to 24 carbon atoms.
  • the fatty acid radicals preferably have 12 to 24 carbon atoms, more preferably 16 to 24 carbon atoms.
  • the proportion of fatty acid esters of sugars based on the total mass is preferably between 0.001 and 5 wt .-%, more preferably between. 0.01 and 5 wt .-%.
  • the degree of esterification of the sugars used is between. 7 and 8.
  • the short-chain fatty acid residues preferably contain 6 to 10 carbon atoms. Particular preference is given to the short-chain fatty acid radical selected from the group consisting of acetic acid, butyric acid, caproic acid, caprylic acid and capric acid.
  • the long-chain fatty acid radical used is preferably one from the group of behenic acid and stearic acid.
  • Suitable carboxyl-functional polyesters can be prepared by the condensation processes known to the polyesters (esterification and / or transesterification) according to the prior art. Also suitable catalysts, such as e.g. Dibutyltin oxide or Titantetrabuty- lat, may optionally be used.
  • Carboxyl-functional copolyesters contain as acid components mainly aromatic polybasic carboxylic acids, for example terephthalic acid, isophthalic acid, phthalic acid, pyromellitic acid, trimellitic acid, 3,6-dichlorophthalic acid, tetrachlorophthalic acid and, where available, their anhydride, chloride or ester. In most cases, they contain at least 50 mol% terephthalic acid and / or isophthalic acid, preferably 80 mol%.
  • aromatic polybasic carboxylic acids for example terephthalic acid, isophthalic acid, phthalic acid, pyromellitic acid, trimellitic acid, 3,6-dichlorophthalic acid, tetrachlorophthalic acid and, where available, their anhydride, chloride or ester. In most cases, they contain at least 50 mol% terephthalic acid and / or isophthalic acid, preferably 80 mol%.
  • the rest of the acids (difference to 100 mol%) consists of aliphatic and / or cycloaliphatic polybasic acids, such as, for example, 1,4-cyclohexadicarboxylic acid, Tetrahydrophthalic acid, hexachlorophthalic acid, aze ⁇ lain Textre, sebacic acid, decanedicarboxylic acid, adipic acid, dodecanedicarboxylic acid, succinic acid, maleic acid or diniere fatty acids, hydroxycarboxylic acids and / or lactones, such as 12-hydroxystearic acid, ⁇ -caprolactam or Hydroxpivalinklare of Neopen- tylglycols can be used.
  • 1,4-cyclohexadicarboxylic acid Tetrahydrophthalic acid, hexachlorophthalic acid, aze ⁇ lainklare, sebacic acid, decanedicarboxylic acid, adipic acid, dodecan
  • monocarboxylic acids e.g. Benzoic acid, tert-butylbenzoic acid, hexahydrobenzoic acid, and saturated aliphatic monocarboxylic acids are used.
  • Suitable alcohol components include aliphatic diols, e.g. Ethylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,2-dimethylpropanediol-1,3 (neopentyl glycol), 2,5-hexanediol, 1.6 Hexanediol, 2, 2- [bis (4-hydroxycyclohexyl)] propane, 1, 4-dimethylolcyclohexane, diethylene glycol, dipropylene glycol and 2,2-bis [4- (2-hydroxy)] phenylpropane.
  • Ethylene glycol 1,3-propanediol
  • 1,2-butanediol 1,3-butanediol
  • 1,4-butanediol 2,2-dimethylpropanediol-1,3 (neopentyl glycol
  • polyols are also used, e.g. Glycerol, hexanetriol, pentaerytlitol, sorbitol, trimethylolethane, trimethylolpropane, and tris (2-hydroxy) isocyanurate.
  • the ⁇ -hydroxyalkylamides of the coating composition according to the invention must contain at least two ⁇ -hydroxyalkylamide groups per molecule and are preferably characterized by the following formula:
  • R 1 is hydrogen or C 1 -C 5 -alkyl
  • R 2 is hydrogen, C 1 -C 5 -alkyl
  • R1 has the meaning given above and.
  • A is a chemical bond or a monovalent or polyvalent organic group derived from ges helpful ⁇ saturated, unsaturated or aromatic hydrocarbon groups, including substituted Kohlen ⁇ hydrogen groups having 2 to 20 carbon atoms, m is 1 to 2, n is 0 to 2 and n + m is at least 2.
  • the equivalent ratio of ⁇ -hydroxyalkylamide equivalents to carboxylic acid equivalents is preferably in the range from 0.6 to 1.6: 1.
  • the customary pigments and / or fillers and / or additives can be used for the production of powder coatings. These are additives from the group of accelerators, leveling and thinning agents, heat, UV and / or HALS stabilizers and / or tribo-additives and, as required, matting material, such as waxes.
  • the preparation of the powder coatings is preferably carried out in the melt by co-extrusion of all formulation ingredients at temperatures between 60 to 140 ° C. The extrudate is then cooled, ground and sieved to a particle size ⁇ 90 microns.
  • Powder coatings suitable such as mixing of the formulation ingredients in solution and subsequent precipitation or removal by distillation of the Lensemit ⁇ means.
  • the application of the powder coating according to the invention is carried out by the methods customary for powder coatings, for example by means of an electrostatic spraying device
  • coated aluminum sheets (layer thickness 70 to 90 ⁇ m also O-panels AL-36 5005H 14/08 [0.8 mm]) were used under extremely fluctuating climatic conditions (8h at 40 ° C / 10% relative humidity, 16 h at 40 ° C / 100% relative humidity). The impact tests were carried out in each case at the end of the dry period according to the method described above on the basis of ASTM D 2794.
  • Crylcoat 7630 (carboxyl-functional copolyester from UCB) having an acid number of 33 mg KOH / g and a Tg of approx. 60 ° C., 36.53 g of Primid XL-552 (Bis [N, N'-butyl) di ( ⁇ -hydroxyethyl) adipamide from EMS-Chemie AG (CH)), 15.71 g Kronos Titan 2160 (TiO 2 from Kronos (D)), 149.18 g Bianco Fisso ABR (BaSO 4 of Company Iciesse SPH (I)), 1.27 g Red Colortherm 130M (pigment from Bayer (D)), 13.27 g Red Irgazine DPP BO (pigment from Ciba (CH)), 75.44 g Yellow Bayferrox 943 (pigment of Bayer (D)), 1.04 g of Yellow Paliotol L 2140HD (pigment from BASF (D)), 10.96 g
  • TSK 20 extruded at a jacket temperature of 110 ° C and a screw revolution of 500 rpm. The extrudate is cooled, ground and sieved to ⁇ 90 ⁇ m.
  • the powder coatings are electrostatically (corona or tribo) on aluminum sheets (O-panel ⁇ L-36 5005 H 14/08 (0.8 mm)), as well as on steel sheets (Q-panel R-36 (0.8 mm.)) applied and cured at a Einbrenntempe ⁇ temperature of 180 ° C and a baking time of 15 min in the electric furnace UT6060 from Heraeus (D).
  • the layer thickness is about 80 microns.
  • Table 1 shows the results of the impact test.
  • FIG. 1 shows the change of the reverse impact under the test conditions defined above.
  • Example 1 (RAL 3016)
  • Crylcoat 7630 (carbo- ⁇ -functional copolyester from UCB) having an acid number of 33 mg KOH / g and a Tg of about 60 ° C., - 36.17 g of Primid XL-552 (bis [N, N ' -di (.beta.-hydroxyethyl) adipamide from EMS-Chemie AG (CH)), 15.55 g Kronos Titan 2160 (TiO 2 from Kronos (D)), 147.69 g Bianco Fisso ABR (BaSO 4 from Iciesse SPH (I)), 1.25 g Red Colortherm 130M (pigment from Bayer (D)), 13.
  • Red Irgazine DPP BO pigment from Ciba (CH)
  • 74.69 g Yellow Bayferrox 943 pigment from Bayer (D)
  • 1.02 g Yellow Paliotol L 2140HD pigment from BASF (D)
  • 10.85 g Resiflow PV88 leveling agent based on polyacrylate, commercial product from Worlee-Chemie GmbH
  • 2.41 g of benzoin, 10.00 g of V6842 additive from EMS Chemie AG (CH)
  • Table 1 shows the results of the impact test.
  • Fig. 1 shows the change of the reverse impact
  • Crylcoat 7630 (carboxyl-functional copolyester from UCB) having an acid number of 33 mg 60 g, 36.54 g of Primid XL-552 (bis [N, N'-di ( ⁇ -hydroxyethyl) adipamide from EMS-Chemie AG (CH)), 28, 88 g Kronos Titan 2160 (TiO 2 from Kronos (D)), 208.91 g Bianco Fisso ⁇ BR (BaSO 4 from Iciesse SPH (I)), 3.15 g Rosa Rubin Hostaperm E (pigment from Clariant (D)), 11.15 g Blue Heliogene K6911D (pigment from BASF (D)), 3, -65 g Yellow Bayferrox 3420 (pigment from Bayer (D)), 10.96 g Resiflow PV88 (leveling agent on polyethylene acrylate base, commercial product of Worlée-Chemie GmbH), and 2.44 g of benzoin are processed and
  • Table 1 shows the results of the impact test.
  • Crylcoat 7630 (carboxyl-functional copolyester from UCB) having an acid number of 33 mg KOH / g and a Tg of approx. 60 ° C., 36.18 g of Primid XL-552 (bis [N, N '] di ( ⁇ -hydroxyethyl) adipamide from EMS-Chemie AG (CH)), 28.59 g Kronos Titan 2160 (TiO 2 from Kronos (D)), 206.82 g Bianco Fisso ABR (BaSO 4 of Company Iciesse SPH (I)), 3.12 g Rosa Rubin Hostaperm E (pigment from Clariant (D)), 11.03 g Blue Heliogene K6911D (pigment from BASF (D)), 3.62 g of Yellow Bayferrox 3420 (pigment from Bayer (D)), 10.85 g of Resiflow PV88 (polyacrylate-based leveling agent, commercial product of Worlée-C
  • Table 1 shows the results of the impact test.
  • FIG. 2 shows the change in the reverse impact under the test conditions defined above.
  • Crylcoat 7630 (carboxyl-functional copolyester from UCB) having an acid number of 33 mg KOH / g and a Tg of approx. 60 ° C., 36.54 g of Primid XL-552 (bis [N, N '] di ( ⁇ -hydroxyethyl) adipamide from EMS-Chemie AG (CH)), 6.14 g Kronos Titan 2160 (TiO 2 from Kronos (D)), 187.58 g Bianco Fisso ABR (BaSO 4 of Company Iciesse SPH. (I)), 34.01 g Green.
  • Fig. 3 shows the change of the reverse impact
  • Crylcoat 7630 (carboxyl-functional copolyester from UCB) having an acid number of 33 mg KOH / g and a Tg of approx. 60 ° C., 36.18 g of Primid XL-552 (bis [N, N '] di ( ⁇ -hydroxyethyl) adipamide from EMS-Chemie AG (CH)), 6.08 g Kronos Titan 2160 (TiO 2 from Kronos (D)), 185.70 g Bianc ⁇ Fisso ABR (BaSO 4 of Company Iciesse SPH (I)), 33.67 g of Green Heliogene K8730 (pigment from BASF (D)), 3.09 g of Black Bayferrox 316 (pigment from Bayer (D)), 24.70 g of Yellow Bayferrox 3910 (pigment from Bayer (D)), 10.85 g Resiflow PV88 (polyacrylate leveling agent, commercial product of Worlée-Chemie GmbH
  • Table 1 shows the results of the impact test.
  • Crylcoat 7630 (carboxyl-functional copolyester from UCB) having an acid number of 33 mg KOH / g and a Tg of approx. 60 ° C., 36.55 g of Primid XL-552 (bis [N, N '] di ( ⁇ -hydroxyethyl) adipamide from EMS-Chemie AG (CH)), 209.54 g Bianco Fisso ABR (BaSO 4 from Iciesse SPH (I), 34.11 g Yellow Bayferox 920 (pigment of the company Bayer (D)), 9.29 g Red Colortherm 130M (pigment from Bayer (D)), 2.42 g Special Black 4 (pigment from Degussa (D)), 0.28 g Yellow Colortherm 10 (cf.
  • Primid XL-552 bis [N, N '] di ( ⁇ -hydroxyethyl) adipamide from EMS-Chemie AG (CH)
  • BaSO 4 from I
  • Pigment from Bayer (D) Pigment from Bayer (D)
  • 2.44 g of benzoin are processed into powder coating analogously to Comparative Example 1 and blended reviewed.
  • Table 1 shows the results of the impact test.
  • Crylcoat 7630 (carboxyl-functional copolyester from UCB) having an acid number of 33 mg KOH / g and a Tg of about 60 ° C., 36.18 g of Primid XL 552 (bis [N, N'-di ( ⁇ -hydroxyethyl) adipamide from EMS-Cher ⁇ ie AG (CH)), 207.45 g Bianco Fisso ABR (BaSO 4 from Iciesse SPH (I), 33.77 g Yellow Bayferox 920 (pigment from Bayer (D)), 9.19 g Red Colortherm 130M (pigment from Bayer (D)), 2.39 g Special Black 4 (pigment from Degussa (D)) , 0/28 g Yellow Colortherm 10 (pigment from Bayer (D)), 10.85 g Resiflow PV88 (polyacrylate-based leveling agent, hands-on product of Worlée-Chemie GmbH), and 2.
  • Table 1 shows the results of the impact test.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne des masses de revêtement thermodurcissables contenant un polyester à fonction carboxyle, qui est produit par une réaction de condensation à partir d'acides polycarboxyliques aliphatiques et/ou cycloaliphatiques et/ou aromatiques, d'anhydrides et d'un ß-hydroxyalkylamide, avec adjonction d'additifs prédéterminés ou de modificateurs d'impact.
PCT/EP2005/008767 2004-08-18 2005-08-11 Masse de revetement thermodurcissable, son utilisation et procede pour produire des laques en poudre Ceased WO2006018236A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP05770396A EP1778806A1 (fr) 2004-08-18 2005-08-11 Masse de revetement thermodurcissable, son utilisation et procede pour produire des laques en poudre

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200410040040 DE102004040040B4 (de) 2004-08-18 2004-08-18 Wärmehärtbare Beschichtungsmasse, deren Verwendung sowie Verfahren zur Herstellung von Pulverlacken
DE102004040040.7 2004-08-18

Publications (1)

Publication Number Publication Date
WO2006018236A1 true WO2006018236A1 (fr) 2006-02-23

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PCT/EP2005/008767 Ceased WO2006018236A1 (fr) 2004-08-18 2005-08-11 Masse de revetement thermodurcissable, son utilisation et procede pour produire des laques en poudre

Country Status (3)

Country Link
EP (1) EP1778806A1 (fr)
DE (1) DE102004040040B4 (fr)
WO (1) WO2006018236A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0322834A2 (fr) * 1987-12-30 1989-07-05 Ppg Industries, Inc. Hydroxyalcoylamide comme agent de durcissement pour composition de revêtement en poudre
EP0471409A1 (fr) * 1990-08-13 1992-02-19 Dsm N.V. Revêtement en poudre
US5346960A (en) * 1992-07-27 1994-09-13 Rohm And Haas Company Fatty acid hydroxyalkylamides as coreactable stabilizers and flow aids for powder coatings
US5847057A (en) * 1996-10-30 1998-12-08 Ems--Inventa Ag Heat-curable coating compounds
JP2001226625A (ja) * 2000-02-17 2001-08-21 Dainippon Ink & Chem Inc 熱硬化性粉体塗料組成物
US20030055142A1 (en) * 1998-06-24 2003-03-20 Steckel Thomas F. Powder coating additive, powder coating composition containing said additive, and method for coating a substrate using said powder coating composition
US20030100646A1 (en) * 2001-10-04 2003-05-29 Anchor Michael J. Powder-based coating composition, a cured film thereof, and a method of improving a color strength of the cured film
US20040014855A1 (en) * 2002-07-20 2004-01-22 Degussa Ag Transparent or pigmented powder coatings based on certain carboxyl-containing polyesters with hydroxyalkylamides and use thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1340049A (en) * 1970-04-22 1973-12-05 Ici Ltd Dyeing process
GB1489485A (en) * 1974-03-25 1977-10-19 Rohm & Haas Method for curing polymers

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0322834A2 (fr) * 1987-12-30 1989-07-05 Ppg Industries, Inc. Hydroxyalcoylamide comme agent de durcissement pour composition de revêtement en poudre
EP0471409A1 (fr) * 1990-08-13 1992-02-19 Dsm N.V. Revêtement en poudre
US5346960A (en) * 1992-07-27 1994-09-13 Rohm And Haas Company Fatty acid hydroxyalkylamides as coreactable stabilizers and flow aids for powder coatings
US5847057A (en) * 1996-10-30 1998-12-08 Ems--Inventa Ag Heat-curable coating compounds
US20030055142A1 (en) * 1998-06-24 2003-03-20 Steckel Thomas F. Powder coating additive, powder coating composition containing said additive, and method for coating a substrate using said powder coating composition
JP2001226625A (ja) * 2000-02-17 2001-08-21 Dainippon Ink & Chem Inc 熱硬化性粉体塗料組成物
US20030100646A1 (en) * 2001-10-04 2003-05-29 Anchor Michael J. Powder-based coating composition, a cured film thereof, and a method of improving a color strength of the cured film
US20040014855A1 (en) * 2002-07-20 2004-01-22 Degussa Ag Transparent or pigmented powder coatings based on certain carboxyl-containing polyesters with hydroxyalkylamides and use thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 200215, Derwent World Patents Index; Class A21, AN 2002-109159, XP002349559 *

Also Published As

Publication number Publication date
EP1778806A1 (fr) 2007-05-02
DE102004040040B4 (de) 2008-05-29
DE102004040040A1 (de) 2006-03-02

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