WO1995027761A1 - Composition pulverulente pour revetements - Google Patents

Composition pulverulente pour revetements Download PDF

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Publication number
WO1995027761A1
WO1995027761A1 PCT/FI1995/000179 FI9500179W WO9527761A1 WO 1995027761 A1 WO1995027761 A1 WO 1995027761A1 FI 9500179 W FI9500179 W FI 9500179W WO 9527761 A1 WO9527761 A1 WO 9527761A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin
coatings
powder composition
epoxy
composition
Prior art date
Application number
PCT/FI1995/000179
Other languages
English (en)
Inventor
Leonid Nikolayevitch Machliakovski
Pauli Antero HÄKKINEN
Andrei M. Filippenko
Nina A. Egorova
Original Assignee
Machliakovski Leonid Nikolayev
Haekkinen Pauli Antero
Filippenko Andrei M
Egorova Nina A
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 Machliakovski Leonid Nikolayev, Haekkinen Pauli Antero, Filippenko Andrei M, Egorova Nina A filed Critical Machliakovski Leonid Nikolayev
Priority to AU21398/95A priority Critical patent/AU2139895A/en
Publication of WO1995027761A1 publication Critical patent/WO1995027761A1/fr

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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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/226—Mixtures of di-epoxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
    • 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
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/28—Applying non-metallic protective coatings
    • H05K3/285—Permanent coating compositions

Definitions

  • This invention is concerned with the preparation of powder polymer compositions based on epoxy resins which can be applied in electronic, electrical engineering industries and other branches of industry where a great demand in protective and decorative coatings with high physicomechanical, dielectric, and decorative properties for the work pieces, including work pieces from the thermally unstable materials exists. This is especially important for the coatings used under the conditions of tropical humidity.
  • powder epoxy composition for coatings based on bisphenol A epoxy resin and hardener representing itself an amorp ⁇ hous salt of polyamine or poly(dimethylaminoalkylj derivative of phenol with polyphenol, of the following formulation (parts by weight).
  • Epoxy powder coatings containing dicyanodiamide as a hardener are also known. These compositions are characterized by a high stability at storage due to low reactivity of dicyanodiamide at 100- 120 ° C and they form coatings with good physicomechanical properties [A. A. Blagonravova and A. I. Nepomnyashchii, Varnish Epoxy Resins /in Russian/, Khimiya, Moscow (1970), pp.204-207].
  • compositions need high temperatures (higher than 160 °C) and long time to be cured and to form coatings with good physicomechanical properties.
  • Powder composition based on epoxy bisphenol A resin which contains dicyanodiamide as a hardener and a binary accelerator consisting of the mixture of zinc acetylacetonate and metal acetylacetonate, which is selected from the group including magne ⁇ sium, aluminium, cadmium, and nickel (Inventor's Certificate No.730716, C 08G 59/44; C 08L 63/02, Inventions Bulletin, 1980).
  • epoxy powder composition for coatings which is the subject of our claim is the composition including epoxy bisphenol A resin, hardener - various biguanides (phenyl biguanide, toluyl biguanide) which has the following formulation (in parts per weight):
  • this composition allows one to obtain coatings at 120°C.
  • essential disadvantages of this composition are: still long curing time (70 minutes) at 120°C, substantial deterioration of adhesion strength and dielectric characteristics of coatings after their utilization in a humid atmosphere at temperature 40 °C.
  • the aim of this invention was to increase curing rate of epoxy powder compositions at temperatures 90-120°C, to enhance adhesion and to retain high dielectric characteristics of coatings at their utilization in conditions of a tropical humidity.
  • the powder composition contains a mixture of epoxy bisphenol A resins as a film-former with epoxide numbers 4-6% and 8-10% (molecular weights 800-1800), usual har ⁇ dener, and in addition to this it contains accelerator - bis-N,N' ⁇ (dimethylureido)diphenyl methane.
  • One preferred composition may include following components with the following ratio of the components (parts per weightbw):
  • composition in addition can include pigments and fillers in amounts of 5-15 pbw and 7-10 pbw respectively against 100 pbw of epoxy resin.
  • the following pigments can, for instance, be used: titanium dioxide (grade RO-2), red iron oxide pigment, black iron oxide pigment, led chrome yellow, Milori blue, phthalocyanine blue, and barium sulfate as a filler.
  • Polyvinyl butyl ether is used in the composition as a flow-control agent.
  • One exemplary hardener to be used is: o-toluyl biguanide of the next structural formula
  • the accelerator of curing is bis-N,N'-(dimethylureido)diphenyl methane with the following structural formula
  • Accelerating effect can be attributed to a higher reactivity of the intermediate active complex formed in the process of curing of epoxy resins in the presence of the curing system aromatic biguanide + bis-N , N ' - (dimethylureido) diphenyl methane .
  • intermediate active complex provides a possibility of making the coatings with a higher adhesion strength, dielectric characteristics, and also provide the retention of dielectric characteristics of coatings in the process of their utilization under the conditions of tropical humidity.
  • the claimed composition provides 6 fold shortening of the curing time at 120° C (2 to 5 fold shortening at 90-100°C) as compared to the known composition mentioned above.
  • Epoxy resins with epoxide numbers 4-6% or 8-10% used in composition one by one do not provide the formation of coatings with needed characteristics at low temperatures because coatings prepared from the compositions containing only one epoxy resin have lower values of specific volume resistance before and after testing them for 1000 hours under the conditions of tropical humidity.
  • coatings prepared from powder compositions based on only one resin with epoxide number 4-6% have poorer decorative appear- ance, and the compositions based on only one resin with epoxide number 8-10% have very short storage life time at room temperature (less than 1 month).
  • polyvinyl butyl ether into the compositions in amounts higher than those pointed out in invention formula deteriorates their friability and shortens storage time to 6 months. Less amounts of polyvinyl butyl ether in compositions than those pointed out in invention formula deteriorate flow and appearance of coatings.
  • the claimed powder compositions are prepared according to the common procedures.
  • the components are preliminarily mixed in a ball mill.
  • the mixture obtained is then extruded through a double-screw extruder at 90-100°C, cooled and ground to the particle size not more than 100 ⁇ m.
  • the compositions thus prepared have storage life time for 12 months at temperature not higher than 25 °C.
  • Gel time of the claimed epoxy powder compositions at 100° C is equal to 17-20 minutes.
  • compositions of examples 2-26 are prepared analogous to the composition described in example 1.
  • the claimed epoxy powder compositions are applied onto the metal surface, as well as onto the temperature-sensitive surfaces, by any of the well-known methods used for application of powder coatings.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)

Abstract

Composition pulvérulente pour revêtements, comprenant, par exemple, les ingredients suivant: une résine époxy-bisphénol A d'un indice époxyde de 4 à 6 %, une résine époxy-bisphénol A d'un indice époxyde de 8 à 10 %, un biguanide aromatique, un bis-N,N'-(diméthylureido)-diphényle méthane et un polyvinyle butyle ether. Des pigments et des charges peuvent également être utilisés. Cette composition peut être durcie à basse température et le revêtement obtenu présente d'exellentes qualités de longévité en conditions d'humidité élevée.
PCT/FI1995/000179 1994-04-07 1995-04-03 Composition pulverulente pour revetements WO1995027761A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU21398/95A AU2139895A (en) 1994-04-07 1995-04-03 Powder composition for coatings

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI941593A FI941593A (fi) 1994-04-07 1994-04-07 Jauhekoostumus päällysteitä varten
FI941593 1994-04-07

Publications (1)

Publication Number Publication Date
WO1995027761A1 true WO1995027761A1 (fr) 1995-10-19

Family

ID=8540465

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FI1995/000179 WO1995027761A1 (fr) 1994-04-07 1995-04-03 Composition pulverulente pour revetements

Country Status (3)

Country Link
AU (1) AU2139895A (fr)
FI (1) FI941593A (fr)
WO (1) WO1995027761A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013072356A1 (fr) * 2011-11-15 2013-05-23 Alzchem Ag Utilisation des n,n'-(diméthyle)-urones et procédé de durcissement des compositions de résine époxyde
US9403976B2 (en) 2010-05-18 2016-08-02 Alzchem Ag Semicarbazones as accelerators for curing epoxy resins
US9499684B2 (en) 2011-11-15 2016-11-22 Alzchem Ag Alkyl or dialkyl-semicarbazone as a hardener for epoxy resin
CN113789034A (zh) * 2021-10-13 2021-12-14 航天特种材料及工艺技术研究所 一种低放热量环氧树脂组合物及其制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4283520A (en) * 1979-04-20 1981-08-11 Ciba-Geigy Corporation Storage-stable, homogeneous mixture containing epoxide resin, curing agent and curing accelerator, and the use of the mixture for producing cured products
US5128425A (en) * 1989-06-22 1992-07-07 Mitsubishi Rayon Co., Ltd. Epoxy resin composition for use in carbon fiber reinforced plastics, containing amine or amide based fortifiers

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4283520A (en) * 1979-04-20 1981-08-11 Ciba-Geigy Corporation Storage-stable, homogeneous mixture containing epoxide resin, curing agent and curing accelerator, and the use of the mixture for producing cured products
US5128425A (en) * 1989-06-22 1992-07-07 Mitsubishi Rayon Co., Ltd. Epoxy resin composition for use in carbon fiber reinforced plastics, containing amine or amide based fortifiers

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DIALOG INFORMATION SERVICES, File 351, World Patent Index 81-95, Dialog Accession No. 007035920, WPI Accession No. 87-035917/05, (PAIQ) PAINT IND. RES. INST., "Powdered Epoxy Pigment Compsn. Contains Epoxy Bisphenol-A and Phenolic Oligomer, Pigment, Filler, Spreading Additive and Specified Urea Deriv. as Hardener"; & *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9403976B2 (en) 2010-05-18 2016-08-02 Alzchem Ag Semicarbazones as accelerators for curing epoxy resins
WO2013072356A1 (fr) * 2011-11-15 2013-05-23 Alzchem Ag Utilisation des n,n'-(diméthyle)-urones et procédé de durcissement des compositions de résine époxyde
CN103917572A (zh) * 2011-11-15 2014-07-09 澳泽化学股份公司 N，n’-(二甲基)-尤戎用于固化环氧树脂-组合物的用途以及方法
US9499684B2 (en) 2011-11-15 2016-11-22 Alzchem Ag Alkyl or dialkyl-semicarbazone as a hardener for epoxy resin
US9663609B2 (en) 2011-11-15 2017-05-30 Alzchem Ag Use of N,N′-(dimethyl) urones and method for curing epoxy resin compositions
CN113789034A (zh) * 2021-10-13 2021-12-14 航天特种材料及工艺技术研究所 一种低放热量环氧树脂组合物及其制备方法

Also Published As

Publication number Publication date
FI941593A (fi) 1995-10-08
AU2139895A (en) 1995-10-30
FI941593A0 (fi) 1994-04-07

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