EP0000798B1 - Pulverförmige Polyurethanlacke - Google Patents

Pulverförmige Polyurethanlacke Download PDF

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Publication number
EP0000798B1
EP0000798B1 EP78200117A EP78200117A EP0000798B1 EP 0000798 B1 EP0000798 B1 EP 0000798B1 EP 78200117 A EP78200117 A EP 78200117A EP 78200117 A EP78200117 A EP 78200117A EP 0000798 B1 EP0000798 B1 EP 0000798B1
Authority
EP
European Patent Office
Prior art keywords
weight
ipdi
caprolactam
isocyanate
temperature
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.)
Expired
Application number
EP78200117A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0000798A1 (de
Inventor
Rainer Dr. Gras
Felix Dr. Schmitt
Elmar Dr. Wolf
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.)
Huels AG
Original Assignee
Chemische Werke Huels 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 Chemische Werke Huels AG filed Critical Chemische Werke Huels AG
Publication of EP0000798A1 publication Critical patent/EP0000798A1/de
Application granted granted Critical
Publication of EP0000798B1 publication Critical patent/EP0000798B1/de
Expired legal-status Critical Current

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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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/8074—Lactams
    • 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
    • C08G2150/00—Compositions for coatings
    • C08G2150/20—Compositions for powder coatings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S528/902—Particulate material prepared from an isocyanate
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]

Definitions

  • E- caprolactam After bad experience with phenol, E- caprolactam, in particular, has established itself as a blocking agent for the isocyanate groups (DE-OS 19 57 483).
  • IPDI 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate
  • Polyurethane powder coatings based on IPDI blocked with e-caprolactam are distinguished from polyurethane powder coatings based on other polyisocyanates in particular by good weather stability, flow properties and thermal stability. But they have the disadvantage - compared e.g. B. with epoxy resin powders - that the curing conditions, d. H. the curing temperature and the curing time are relatively high.
  • powder coatings made of macromolecular compounds containing hydroxyl groups such as polyesters, polyacrylates and epoxy resins, and ⁇ -caprolactam-blocked polyisocyanates do not have the abovementioned disadvantages or do so in a very weakened form if they are the triisocyanatoisocyanurate from 3-isocyanatomethyl as the polyisocyanate -3,5,5-trimethylcyclohexyl isocyanate and optionally oligomers together with monomeric 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate.
  • the invention therefore relates to powdered polyurethane lacquers comprising hydroxyl-containing polyesters, polyacrylates or epoxy resins and s-caprolactam-blocked polyisocyanates as the curing component, characterized in that the triisocyanato isocyanurate of 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate and optionally oligomers together with monomeric as the polyisocyanate component 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate is used.
  • This aliphatic triisocyanate isocyanurate can be prepared by the process of DE-OS 23 25 826.
  • a further suitable trimerization catalyst is also described in DE-OS 26 44 684.
  • the trimerization can be carried out in bulk or in inert solvents. To carry out the trimerization process, it is essential to stop the reaction at a certain NCO content of the mixture, preferably when 30-60% of the NCO groups have reacted with trimerization.
  • the unreacted isocyanate is then separated from the triisocyanurate by thin-layer distillation.
  • the accessible triisocyanatoisocyanurate is used in a mixture with isocyanurate-free diisocyanate for blocking with s-caprolactam.
  • the addition of the isocyanurate-free diisocyanate allows the properties of the process products, in particular their melting point, to be varied in a desired manner in a simple manner.
  • Triisocyanatoisocyanurate and monomeric diisocyanate are used in a weight ratio of approximately 80:20 to 30:70.
  • the isocyanurate groups which are not completely blocked with s-caprolactam are also suitable for the preparation of the powdered coating compositions according to the invention, but not more than one isocyanate group per molecule may be free, since otherwise the Mixing of crosslinking components occurs.
  • the polyesters can also contain monofunctional carboxylic acids, e.g. B. benzoic acid, and acyclic polycarboxylic acids such as adipic acid, 2,4,4- (2,2,4) -trimethy! Adipic acid, sebacic acid, dodecanedicarboxylic acid.
  • the polyesters are prepared in a manner known per se by esterification or transesterification, if appropriate in the presence of customary catalysts, end products being obtained by suitable choice of the COOH / OH ratio, the hydroxyl number of which is between about 40 and 240, preferably between about 40 and about 150 , lies.
  • the softening temperatures of the polyesters must be so low that they can be processed at temperatures between about 70.degree. C. and 120.degree. C. with the additives necessary for the preparation of the coating compositions according to the invention.
  • the softening points must be so high that the coating compositions according to the invention obtained from the polyesters can be ground to form non-clumping, free-flowing powders with a particle size of approximately 20 to approximately 120 ⁇ m.
  • the coating compositions of the invention can in suitable mixing units, for. B. in stirred tanks or mixing screws.
  • Conventional additives such as pigments, leveling agents, plasticizers, fillers and catalysts, can also be added in a simple manner without the use of solvents.
  • the powder coating agents can be easily in the usual manner, i.e. H. for example in a fluidized bed or by electrostatic spraying; by heating to temperatures above about 150 ° C, preferably between about 160 and 200 ° C, coatings with excellent properties are obtained.
  • A-1 6.75 moles (1323 g) of dimethyl terephthalate, 2.25 moles (373.5 g) of terephthalic acid, 6 moles (624 g) of 1,3-dimethylpropane diol, 1 mole (134 g) of trimethylol propane and 3.0 Mol (432 g) 1,4-dimethylolcyclohexane was combined in a 5 glass flask and heated with the help of an oil bath. After most of the substances had melted, 0.1% by weight of dibutyltin oxide was added as an esterification catalyst at a temperature of 160.degree. The bottom temperature was slowly increased to 185 ° C. within 3 h. The further temperature increase to a maximum of 230 ° C.
  • A-2 9 moles (1746 g) of dimethyl terephthalate, 4 moles (416 g) of 1,3-dimethylpropanediol, 3.75 moles (540 g) of 1,4-dimethylolcyclohexane and 2.5 moles (335 g) of trimethylol propane were, as described in A-1, subjected to the esterification under the catalytic action of 0.05% by weight of dibutyltin oxide.
  • the first elimination of methanol occurred at a bottom temperature of about 170 ° C.
  • the transesterification was completed after about 14 hours, with transesterification at a maximum temperature in the final phase of 220 ° C.
  • the vacuum treatment see A-1 and cooling, the following chemical and physical data were determined:
  • B-3 100 parts by weight of IPDI were mixed with 0.75 part by weight of a catalyst system composed of 2 parts by weight of propylene oxide and 1 part by weight of 1,4-diazabicyclooctane (2.2.2) for 2 hours at 120 ° C heated. During this time, the NCO content fell from 37.8% to 29.4%.
  • evacuation was carried out at 120 ° C. and 3999 Pa (30 torr) for 15 minutes. During this time the NCO content of the reaction mixture changed to 27%.
  • the powder coating was prepared in the manner corresponding to the prior art. It should therefore only be described briefly.
  • composition corresponded to the following recipe:
  • a masterbatch of the leveling agent was made in the polyester. Masterbatch, polyester, hardener and pigment were intimately mixed in a solid mixer and then extruded at a melt temperature of 95-100 ° C. The solidified melt was ground to a grain size ⁇ 100, and the powder coating was applied electrostatically to 1 mm steel test panels.
  • the paints were baked under various curing conditions and subjected to a paint test after 24 hours.
  • the elasticity which is measured by the Erichsen indentation, is a good parameter for assessing the degree of curing.
  • Example 1 The technology described in Example 1 was used to produce a polyurethane powder coating of the formulation below, applied to 1 mm steel sheet and cured under various conditions.
  • polyester A-2 100 parts by weight of polyester A-2 were mixed with 46.8 parts by weight of the isocyanate-isocyanurate mixture of IPDI, blocked with s-caprolactam, prepared according to C-2.2, and 0.73 parts by weight of silicone oil in the Melt homogenized at temperatures of 120-140 ° C with an intensive stirrer. After cooling, the homogeneous melt was broken and then ground with a pin mill to a grain size ⁇ 100 ⁇ . The clear lacquer powder produced in this way was applied with an electrical powder spraying system at 60 kV to iron plates primed with zinc phosphate and baked in a forced-air drying cabinet at temperatures between 180 and 200 ° C.
  • polyester A-2 was reacted with the hardener described in C-2.1 in an equivalent amount and prepared as described in Example 4.
  • the clearcoat was applied as described in Example 4 and baked in a forced air drying cabinet at between 180 and 200 ° C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)
EP78200117A 1977-08-06 1978-07-25 Pulverförmige Polyurethanlacke Expired EP0000798B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772735497 DE2735497A1 (de) 1977-08-06 1977-08-06 Pulverfoermige polyurethanlacke
DE2735497 1977-08-06

Publications (2)

Publication Number Publication Date
EP0000798A1 EP0000798A1 (de) 1979-02-21
EP0000798B1 true EP0000798B1 (de) 1981-09-02

Family

ID=6015781

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78200117A Expired EP0000798B1 (de) 1977-08-06 1978-07-25 Pulverförmige Polyurethanlacke

Country Status (9)

Country Link
US (1) US4246380A (enrdf_load_stackoverflow)
EP (1) EP0000798B1 (enrdf_load_stackoverflow)
JP (1) JPS5440832A (enrdf_load_stackoverflow)
AT (1) AT376992B (enrdf_load_stackoverflow)
DE (2) DE2735497A1 (enrdf_load_stackoverflow)
DK (1) DK345478A (enrdf_load_stackoverflow)
FI (1) FI63770C (enrdf_load_stackoverflow)
IT (1) IT1097679B (enrdf_load_stackoverflow)
ZA (1) ZA784439B (enrdf_load_stackoverflow)

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DE2929150A1 (de) * 1979-07-19 1981-02-12 Huels Chemische Werke Ag Pulverfoermige ueberzugsmassen mit hoher lagerstabilitaet sowie deren herstellung
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DE9413475U1 (de) 1994-08-20 1994-10-13 Mannesmann Kienzle Gmbh, 78052 Villingen-Schwenningen Fahrtschreiber mit Mitteln zur geräteseitigen Befestigung eines den Geberleitungen zugeordneten Schutzrohres
DE19603389A1 (de) 1996-01-31 1997-08-07 Huels Chemische Werke Ag Blockierte aliphatische Diisocyanate oder Diisocyanat-Addukte
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DE102011006163A1 (de) * 2011-03-25 2012-09-27 Evonik Degussa Gmbh Lagerstabile Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung mit flüssigen Harzkomponenten
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EP3929233A1 (de) 2020-06-25 2021-12-29 Evonik Operations GmbH Reaktive polyurethan-zusammensetzungen
CN119013325A (zh) 2022-02-28 2024-11-22 旭化成株式会社 封端异氰酸酯组合物、涂料组合物和涂膜
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Also Published As

Publication number Publication date
AT376992B (de) 1985-01-25
EP0000798A1 (de) 1979-02-21
DE2735497A1 (de) 1979-02-15
DK345478A (da) 1979-02-07
DE2861007D1 (en) 1981-11-26
JPS6131744B2 (enrdf_load_stackoverflow) 1986-07-22
IT7826477A0 (it) 1978-08-04
IT1097679B (it) 1985-08-31
FI63770C (fi) 1983-08-10
ATA568378A (de) 1984-06-15
JPS5440832A (en) 1979-03-31
FI782405A7 (fi) 1979-02-07
US4246380A (en) 1981-01-20
ZA784439B (en) 1979-10-31
FI63770B (fi) 1983-04-29

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