CA1329856C - Thermosetting epoxy resin based powder coating - Google Patents
Thermosetting epoxy resin based powder coatingInfo
- Publication number
- CA1329856C CA1329856C CA000568485A CA568485A CA1329856C CA 1329856 C CA1329856 C CA 1329856C CA 000568485 A CA000568485 A CA 000568485A CA 568485 A CA568485 A CA 568485A CA 1329856 C CA1329856 C CA 1329856C
- Authority
- CA
- Canada
- Prior art keywords
- epoxy resin
- based powder
- acid anhydride
- powder composition
- resin based
- 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 - Fee Related
Links
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
- 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
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing 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
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/092—Polycarboxylic acids
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)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
A thermosetting epoxy resin based powder composition composed of an epoxy resin, a high-melting point polycarboxylic acid anhydride and a filler, the high-melting point polycarboxylic acid anhydride comprising fine particles of no more than 149 µm in average size that have reacted with the epoxy resin in the molten state on their surfaces.
A thermosetting epoxy resin based powder composition composed of an epoxy resin, a high-melting point polycarboxylic acid anhydride and a filler, the high-melting point polycarboxylic acid anhydride comprising fine particles of no more than 149 µm in average size that have reacted with the epoxy resin in the molten state on their surfaces.
Description
13298~
THERMOSETTING EPOXY RESIN BASED
POWDER COATING
-: . :- -FIELD OF T~E INVENTION
The present invention relates to a thermosetting epoxy resin based powder coating (which is hereinafter referred to simply as a powder coating).
BACKGROUND OF THE INVENTION ~.
Various powder coatings have been known that consist ba~ically of a uniform mixture of an epoxy resin, a carboxylic acid anhydride in powder form, and a filler.
These powder coatings are ap~lied by the ~luidized-bed coating process, the electro~tatic fluidized-bed coating process or some other ~uitable methods to form insulation films on electrical and electronic devices.
Powder coatings are either melt-mixed or dry-blended. In the first process, dry ingredients including an epoxy resin ba~e and additives such as a curing agent and a ~iller are mixed; the premix is then melt-compounded, cooled to ~olidify, finely ground, and clas~fied. In the second proce~, the premix of dry lngrédient~ ifi pre~ure-compounded, finely ground and 20 cla8~i~ied. I~ a high-melting point polycarboxylic acid ;
-anhydride used as the curing agent poorly mixe~ and di8per~e~ in the re~in, a product having desired coating ;:
13298~i performance cannot be attained. If a low-melting point monocarboxylic acid anhydride is additionally used in an attempt to improve the dispersive ~iscibility of the polycarboxylic acid anhydride with the resin, the anti-blocking property and storage stability of the final productwill be impaired. If the polycarboxylic acid anhydride is mixed and dispersed in the resin at elevated temperatures, the storage stability of the final product i8 impaired.
SUMMARY OF THE INVENTION
An ob~ect, therefore, of the present invention is to provide a thermosetting epoxy resin based powder coating that i8 ~ree ~rom the aforementioned defects of the prior art.
The thermosetting epoxy resin based powder coating o~ the present invention that attains this object i8 a powder composition compo~ed o~ an epoxy resin, a high-melting point polycarboxylic acid anhydride and a ~iller, and the high-melting point polycarboxylic acid anhydride compri~e~ ~ine particles o~ not more than 149 ~m in average ~ize that have reacted with the epoxy re~in in the molt~n ;; ~tate on thelr ~ur~ace~.
Accordlngly, in one aspect, the invention resides in a thermosetting epoxy resin based powder compo~ition - oompo~-d o~ an epoxy re~in, a high-melting point .
~ 25 polycarboxylic acid anhydride and a filler, ~aid high--- melting polnt poly¢arboxylic acid anhydride having a higher ~ C ~ - 2 ~
~ ' ~
-- 1 3 2 ~
melting temperature than the epoxy resin and comprising fine paxticles of no more that 149 ~m in average size that have : .
reacted with the epoxy resin in the molten state on their surfaces -DETAILED DESCRIPTION OF THE INVENTION
. ._ :.. ;.
The epoxy resin for use in the present invention . :
may be seleoted from ~mong known epoxy re~ins that are ~ ~
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commonly used in powder coatings,-such as bisphenol A type epoxy resins, novolac type epoxy resins, and alicyclic epoxy resins. Epoxy resins that are solid at ordinary temperatures are preferably used in the present invention S and they may, if desired, be combined with epoxy resins that are liquid at ordinary temperatures in a low proportion.
The high-melting point polycarboxylic acid anhydride used as a curing agent in the present invention 10 i8 such that it melts at a higher temperature than the epoxy resin used (if two or more epoxy resins are used, the one having the highe~t melting point is meant).
Examples of such high-melting point polycarboxylic acid anhydride include: phthalic anhydride (m.p. 128 - 130C), benzophenone tetracarboxylic acid anhydride (m.p. 218 -225C), 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride ~m.p. 167C), tetrahydrophthalic anhydride (m.p. 100C), trimellitic anhydride (m.p. 145C), and pyromellitic anhydride ~m.p.
265C).
In the present invention, the polycarboxylic acid anhydrlde 1~ used in the form of fine particles of not more than 149 ~m, preferably between 5 and 44 ~m, in average ~ize. According to the ~tudies conducted by the 2S pra~ent inventors, when ~uch fine particulate poly-1 329~6 :'.',,' - .
carboxylic acid anhydride was compounded into a molten epoxy resin, with the compounding temperature and time being appropriately controlled (preferably the compounding temperature being 50 to 150 C and time being 1 to 5 minutes), the most part ~preferably at least 70 wt%) of the polycarboxylic acid anhydride used reacted with the epoxy resin on the surfaces of the particles of the anhydride and dispersed and mixed uniformly with the resin so as to provide a powder coating that had good storage stability and appearance (i.e., anti-blocking property).
If the polycarboxylic acid anhydride has an average particle size exceeding 149 ~m, its particles will disperse and mix in the epoxy resin only poorly during high-temperature coatins operations even if the anhydride particle~ have been reacted with the molten epoxy resin on their ~urfaces. This will result in failure to produce a coating film havlng good appearance. In mixing the fine particulate polycarboxylic acid anhydride with the molten epoxy re~in, selection of an appropriate heating temperature is also important. If the temperature for di~persing and mixing in the molten reain i8 excessive, most of the ~ine particles of the anhydride will dissolve by reacting with the redin and the storage stability of the latter wlll be impaired. Therefore, it is important for the purpo8e8 of the pre8ent invention that the 13~93~ 6 polycarboxylic acid anhydride used as a curing agent be in fine particulate form and that the fine particles react with the resin on their surfaces without losing their shape as fine particles. Needless to say, some part of the fine particles of the polycarboxylic acid anhydride may dissolve away as a result of reaction with the molten epoxy resin. The polycarboxylic acid anhydride is incorporated in the powder coating of the present invention in an amount generally ranging from 0.45 to 1.55 equivaients, preferably from 0.65 to 1.25 equivalents, per epoxy equivalent weight of the epoxy resin.
The filler used in the present invention can be selected from among those which are commonly employed with the powder coating of the type contemplated by the present invention, such as the powders of zircon, talc, quartz glass, calcium carbonate, magnesia, calcium silicate and silica. ~hese fillers have particle sizes of not more than 149 ~m (not coar~er than 100 mesh), preferably in the range of 2 ~m to 44 ~m. ~he filler i9 to be incorporated in an amount that generally ranges rom 5 to 300 parts by weight, preferably from 30 to 150 part~ by weight, per 100 ~arts by weight o the epoxy re~in.
Be~ides the ingredients de~cribed above, the powder coating of the present invention may also incorporate some other common additives ~uch a~ a cure : 13?~98~6 ~
accelerator (e.y., imidazole, dicyandiamide and tertiary amine), a pigment (e.g., chromium oxide and red iron oxide) and a flow-control agent (e.g., acrylic ester oligomer).
The following example is provided for the purpose of further illustrating the present invention but is in no way to be taken as limiting.
EX~MPLE
A hundred parts by weight of Epikote 1002 (the trade name of Yuka-Shell Epoxy Co., Ltd. for a bisphenol A
type epoxy resin that i5 solid at ordinary temperature and which has a melting point of 83C) was provided. To this epoxy re~in, 100 parts by weight of fine particulate calcium sil~cate (wollastonite with an average particle ~ize of about 3 ~m) and one of the polycarboxylic acid anhydride~ shown in Table 1 a~ curing agents were added.
The ingredients were melt-mixed under heating, cooled to ~olidify, and finely ground.
~he resulting coatlng powders were visually checked for their appearance ~anti-blocking property). At the ~ame tlme, the ~torage stabllity of theae powders was evaluated by the followlng method. The results are shown in Table 1.
~ ~rade ~ rk 1329 ~ 6 (Test for Storage Stability) The gel time (at 150C) of each powder was measured at immediately a~ter preparation (initial) and 7 days after its preparation and the change that occurred was measured in accordance with JIS C-2104.
The symbols appearing in the column of "Curing Agent" in Table 1 have the following meanings: -~
BTDA, benzophenone tetracarboxylic acid :::
anhydride; -MCTC, 5-~2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride; ::
THPA, tetrahydrophthalic anhydride.
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As will be understood the data shown in Table 1, the coating powder samples prepared in accordance with the present invention have the high melting point polycarboxylic acids (curing agent) dispersed and mixed sufficiently uniformly in an epoxy resin to provide good appearance (anti-blocking property). When these powders are coated on electrical or electronic devices, they~: :
produce insulation films having few pinholes or voids,:; .
thereby increasing the reliability of the electrical or electronic devices. As a further advantage, the powder coating of the present invention has excellent storage stability.
While the invention has been described in detail and w~ th reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departlng from the spirit and scope thereof. ..
,~
,, ::
_ 9 _ . . . :: ; .
THERMOSETTING EPOXY RESIN BASED
POWDER COATING
-: . :- -FIELD OF T~E INVENTION
The present invention relates to a thermosetting epoxy resin based powder coating (which is hereinafter referred to simply as a powder coating).
BACKGROUND OF THE INVENTION ~.
Various powder coatings have been known that consist ba~ically of a uniform mixture of an epoxy resin, a carboxylic acid anhydride in powder form, and a filler.
These powder coatings are ap~lied by the ~luidized-bed coating process, the electro~tatic fluidized-bed coating process or some other ~uitable methods to form insulation films on electrical and electronic devices.
Powder coatings are either melt-mixed or dry-blended. In the first process, dry ingredients including an epoxy resin ba~e and additives such as a curing agent and a ~iller are mixed; the premix is then melt-compounded, cooled to ~olidify, finely ground, and clas~fied. In the second proce~, the premix of dry lngrédient~ ifi pre~ure-compounded, finely ground and 20 cla8~i~ied. I~ a high-melting point polycarboxylic acid ;
-anhydride used as the curing agent poorly mixe~ and di8per~e~ in the re~in, a product having desired coating ;:
13298~i performance cannot be attained. If a low-melting point monocarboxylic acid anhydride is additionally used in an attempt to improve the dispersive ~iscibility of the polycarboxylic acid anhydride with the resin, the anti-blocking property and storage stability of the final productwill be impaired. If the polycarboxylic acid anhydride is mixed and dispersed in the resin at elevated temperatures, the storage stability of the final product i8 impaired.
SUMMARY OF THE INVENTION
An ob~ect, therefore, of the present invention is to provide a thermosetting epoxy resin based powder coating that i8 ~ree ~rom the aforementioned defects of the prior art.
The thermosetting epoxy resin based powder coating o~ the present invention that attains this object i8 a powder composition compo~ed o~ an epoxy resin, a high-melting point polycarboxylic acid anhydride and a ~iller, and the high-melting point polycarboxylic acid anhydride compri~e~ ~ine particles o~ not more than 149 ~m in average ~ize that have reacted with the epoxy re~in in the molt~n ;; ~tate on thelr ~ur~ace~.
Accordlngly, in one aspect, the invention resides in a thermosetting epoxy resin based powder compo~ition - oompo~-d o~ an epoxy re~in, a high-melting point .
~ 25 polycarboxylic acid anhydride and a filler, ~aid high--- melting polnt poly¢arboxylic acid anhydride having a higher ~ C ~ - 2 ~
~ ' ~
-- 1 3 2 ~
melting temperature than the epoxy resin and comprising fine paxticles of no more that 149 ~m in average size that have : .
reacted with the epoxy resin in the molten state on their surfaces -DETAILED DESCRIPTION OF THE INVENTION
. ._ :.. ;.
The epoxy resin for use in the present invention . :
may be seleoted from ~mong known epoxy re~ins that are ~ ~
'.'"'~'"
'' ' ""`'' .. ..
'.':. ', :' . i.~ ' ` ' ~
' '' ' ' ' . ,. ,~ .
. . .
. .
;.". ';
':.,'.".
;. ~ . .
.,~ ~. . ~
, .:. .
~ ~ ~"., ~
.. - "~ . .
:~ - 2~ - :
`: ~' '.'`',''."
1 3 ~
commonly used in powder coatings,-such as bisphenol A type epoxy resins, novolac type epoxy resins, and alicyclic epoxy resins. Epoxy resins that are solid at ordinary temperatures are preferably used in the present invention S and they may, if desired, be combined with epoxy resins that are liquid at ordinary temperatures in a low proportion.
The high-melting point polycarboxylic acid anhydride used as a curing agent in the present invention 10 i8 such that it melts at a higher temperature than the epoxy resin used (if two or more epoxy resins are used, the one having the highe~t melting point is meant).
Examples of such high-melting point polycarboxylic acid anhydride include: phthalic anhydride (m.p. 128 - 130C), benzophenone tetracarboxylic acid anhydride (m.p. 218 -225C), 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride ~m.p. 167C), tetrahydrophthalic anhydride (m.p. 100C), trimellitic anhydride (m.p. 145C), and pyromellitic anhydride ~m.p.
265C).
In the present invention, the polycarboxylic acid anhydrlde 1~ used in the form of fine particles of not more than 149 ~m, preferably between 5 and 44 ~m, in average ~ize. According to the ~tudies conducted by the 2S pra~ent inventors, when ~uch fine particulate poly-1 329~6 :'.',,' - .
carboxylic acid anhydride was compounded into a molten epoxy resin, with the compounding temperature and time being appropriately controlled (preferably the compounding temperature being 50 to 150 C and time being 1 to 5 minutes), the most part ~preferably at least 70 wt%) of the polycarboxylic acid anhydride used reacted with the epoxy resin on the surfaces of the particles of the anhydride and dispersed and mixed uniformly with the resin so as to provide a powder coating that had good storage stability and appearance (i.e., anti-blocking property).
If the polycarboxylic acid anhydride has an average particle size exceeding 149 ~m, its particles will disperse and mix in the epoxy resin only poorly during high-temperature coatins operations even if the anhydride particle~ have been reacted with the molten epoxy resin on their ~urfaces. This will result in failure to produce a coating film havlng good appearance. In mixing the fine particulate polycarboxylic acid anhydride with the molten epoxy re~in, selection of an appropriate heating temperature is also important. If the temperature for di~persing and mixing in the molten reain i8 excessive, most of the ~ine particles of the anhydride will dissolve by reacting with the redin and the storage stability of the latter wlll be impaired. Therefore, it is important for the purpo8e8 of the pre8ent invention that the 13~93~ 6 polycarboxylic acid anhydride used as a curing agent be in fine particulate form and that the fine particles react with the resin on their surfaces without losing their shape as fine particles. Needless to say, some part of the fine particles of the polycarboxylic acid anhydride may dissolve away as a result of reaction with the molten epoxy resin. The polycarboxylic acid anhydride is incorporated in the powder coating of the present invention in an amount generally ranging from 0.45 to 1.55 equivaients, preferably from 0.65 to 1.25 equivalents, per epoxy equivalent weight of the epoxy resin.
The filler used in the present invention can be selected from among those which are commonly employed with the powder coating of the type contemplated by the present invention, such as the powders of zircon, talc, quartz glass, calcium carbonate, magnesia, calcium silicate and silica. ~hese fillers have particle sizes of not more than 149 ~m (not coar~er than 100 mesh), preferably in the range of 2 ~m to 44 ~m. ~he filler i9 to be incorporated in an amount that generally ranges rom 5 to 300 parts by weight, preferably from 30 to 150 part~ by weight, per 100 ~arts by weight o the epoxy re~in.
Be~ides the ingredients de~cribed above, the powder coating of the present invention may also incorporate some other common additives ~uch a~ a cure : 13?~98~6 ~
accelerator (e.y., imidazole, dicyandiamide and tertiary amine), a pigment (e.g., chromium oxide and red iron oxide) and a flow-control agent (e.g., acrylic ester oligomer).
The following example is provided for the purpose of further illustrating the present invention but is in no way to be taken as limiting.
EX~MPLE
A hundred parts by weight of Epikote 1002 (the trade name of Yuka-Shell Epoxy Co., Ltd. for a bisphenol A
type epoxy resin that i5 solid at ordinary temperature and which has a melting point of 83C) was provided. To this epoxy re~in, 100 parts by weight of fine particulate calcium sil~cate (wollastonite with an average particle ~ize of about 3 ~m) and one of the polycarboxylic acid anhydride~ shown in Table 1 a~ curing agents were added.
The ingredients were melt-mixed under heating, cooled to ~olidify, and finely ground.
~he resulting coatlng powders were visually checked for their appearance ~anti-blocking property). At the ~ame tlme, the ~torage stabllity of theae powders was evaluated by the followlng method. The results are shown in Table 1.
~ ~rade ~ rk 1329 ~ 6 (Test for Storage Stability) The gel time (at 150C) of each powder was measured at immediately a~ter preparation (initial) and 7 days after its preparation and the change that occurred was measured in accordance with JIS C-2104.
The symbols appearing in the column of "Curing Agent" in Table 1 have the following meanings: -~
BTDA, benzophenone tetracarboxylic acid :::
anhydride; -MCTC, 5-~2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride; ::
THPA, tetrahydrophthalic anhydride.
...,: .
';''' ' ' "' , .:
- ~ ' .
.
,:
',~: ~ ;, .
~', :
~ ," 132~8~6 U ~ ..
Y~ O O O O O O O ~ ;
~3. ~ V . :
o ~ o ~ ~ o _I ~ ~ o ~ 0 a~
~ ,~ ~_ . .: .
~n , . .:
O .,~ 0 ¦ ~l N _I Ul ~ ~ ` ;
JJ C . :. ~
U:~ 1_~ ':
',.':
~ '11 ~ ~ v ~,, 3 O 0 ~1 0 ~ O O '-,~ v O O la o 1~ o o 3~o :;,',' ~ .^ ~ N
r~ E~ ~
# '.:' O O O O O ''' ' ~ O O o ~ O 11') 1. ~ ~o , : O O o o o ' ' V U) .~,~
, ~ ,~
:,.
In O
N N ~ .
0 ~ ' -1.~ 1~1 ''.
. I
1~ ~ ~I N ~ ~ U~ ~0 ~3298~
As will be understood the data shown in Table 1, the coating powder samples prepared in accordance with the present invention have the high melting point polycarboxylic acids (curing agent) dispersed and mixed sufficiently uniformly in an epoxy resin to provide good appearance (anti-blocking property). When these powders are coated on electrical or electronic devices, they~: :
produce insulation films having few pinholes or voids,:; .
thereby increasing the reliability of the electrical or electronic devices. As a further advantage, the powder coating of the present invention has excellent storage stability.
While the invention has been described in detail and w~ th reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departlng from the spirit and scope thereof. ..
,~
,, ::
_ 9 _ . . . :: ; .
Claims (8)
1. A thermosetting epoxy resin based powder composition composed of an epoxy resin, a high-melting point polycarboxylic acid anhydride and a filler, said high-melting point polycarboxylic acid anhydride having a higher melting temperature than the epoxy resin and comprising fine particles of no more that 149 µ m in average size that have reacted with the epoxy resin in the molten state on their surfaces.
2. A thermosetting epoxy resin based powder composition as in claim 1, wherein said eposy resin is selected from bisphenol A type epoxy resins, novolac type epoxy resins and alicyclic epoxy resins.
3. A thermosetting epoxy resin based powder composition as in claim 1, wherein said high-melting point polycarboxylic acid anhydride is selcted from phthalic anhydride, benzophenone tetracarboxylic acid anhydride, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride, tetrahydrophthalic anhydride, trimellitic anhydride, and pyromellitic anhydride.
4. A thermosetting epoxy resin based powder composition as in claim 1, wherein the particle size of said high-melting point polycarboxylic acid anhydride is 5 - 44 µm.
5. A thermosetting epoxy resin based powder composition as in claim 1, wherein the amount of said polycarboxylic acid anhydride is from 0.45 to 1.55 equivalents per epoxy equivalent weight of said epoxy resin.
6. A thermosetting epoxy resin based powder composition as in claim 1, wherein said filler is selected from the powders of zircon, talc, quartz glass, calcium carbonate, magnesia, calcium silicate and silica.
7. A thermosetting epoxy resin based powder composition as in claim 6, wherein said filler has a particle size of 2 - 44 µm.
8. A thermosetting epoxy resin based powder composition as in claim 6, wherein the amount of said filler ranges from 5 to 300 parts by weight per 100 parts by weight of said epoxy resin.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61290161A JPH0781098B2 (en) | 1986-12-05 | 1986-12-05 | Thermosetting epoxy resin powder coating |
| CA000568485A CA1329856C (en) | 1986-12-05 | 1988-06-02 | Thermosetting epoxy resin based powder coating |
| KR1019880006710A KR960008473B1 (en) | 1986-12-05 | 1988-06-04 | Thermosetting epoxy resin based powder coating |
| US08/240,040 US5455290A (en) | 1986-12-05 | 1994-05-09 | Powder composition of epoxy resin, high melting acid anhydride and calcium silicate |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61290161A JPH0781098B2 (en) | 1986-12-05 | 1986-12-05 | Thermosetting epoxy resin powder coating |
| CA000568485A CA1329856C (en) | 1986-12-05 | 1988-06-02 | Thermosetting epoxy resin based powder coating |
| KR1019880006710A KR960008473B1 (en) | 1986-12-05 | 1988-06-04 | Thermosetting epoxy resin based powder coating |
| US08/240,040 US5455290A (en) | 1986-12-05 | 1994-05-09 | Powder composition of epoxy resin, high melting acid anhydride and calcium silicate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1329856C true CA1329856C (en) | 1994-05-24 |
Family
ID=27426548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000568485A Expired - Fee Related CA1329856C (en) | 1986-12-05 | 1988-06-02 | Thermosetting epoxy resin based powder coating |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5455290A (en) |
| JP (1) | JPH0781098B2 (en) |
| KR (1) | KR960008473B1 (en) |
| CA (1) | CA1329856C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19813286A1 (en) * | 1998-03-26 | 1999-09-30 | Metallgesellschaft Ag | Process for separating vaporous phthalic anhydride from a gas stream |
| US6677484B1 (en) * | 2000-07-31 | 2004-01-13 | E. I. Du Pont De Nemours And Company | Melt-sprayed curing agent powder and powder coating compositions made therefrom |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3269974A (en) * | 1963-06-25 | 1966-08-30 | Hysol Corp | Powdered epoxy resin compositions |
| US3484398A (en) * | 1965-03-18 | 1969-12-16 | Dexter Corp | Powdered epoxy resin compositions |
| US3374193A (en) * | 1965-07-19 | 1968-03-19 | Shell Oil Co | Polyepoxide fluidized bed coating compositions |
| US3624032A (en) * | 1969-04-24 | 1971-11-30 | Morton Int Inc | Epoxy compositions cured with carboxylic acid anhydrides and metallic salt of acetylacetone |
| BE789216A (en) * | 1971-10-01 | 1973-03-26 | Shell Int Research | OMPOSITIES WERKWIJZE TER BEREIDING VAN POEDERVORMIGE DEKLAAGC |
| US3989573A (en) * | 1973-12-11 | 1976-11-02 | Westinghouse Electric Corporation | Glass-epoxy laminates for high temperature use |
| US4009223A (en) * | 1974-05-08 | 1977-02-22 | Westinghouse Electric Corporation | Thin film electrostatic epoxy coating powder |
| GB1498542A (en) * | 1975-12-30 | 1978-01-18 | Ciba Geigy Ag | Compositions for curing epoxide resins |
| US4271061A (en) * | 1979-03-06 | 1981-06-02 | Nitto Electric Industrial Co., Ltd. | Epoxy resin compositions for sealing semiconductors |
| CA1154895A (en) * | 1980-02-21 | 1983-10-04 | Dieter Skudelny | Flowable mixture and use of synthetic calcium silicate |
| CA1164124A (en) * | 1980-07-15 | 1984-03-20 | Kurt Munk | Pourable solid mixture |
| US4358552A (en) * | 1981-09-10 | 1982-11-09 | Morton-Norwich Products, Inc. | Epoxy resinous molding compositions having low coefficient of thermal expansion and high thermal conductivity |
| US4560739A (en) * | 1983-12-02 | 1985-12-24 | Ciba-Geigy Corporation | Triglycidyl compounds of aminophenols |
| JPS6189271A (en) * | 1984-10-08 | 1986-05-07 | Sumitomo Deyurezu Kk | Epoxy resin composition for powder coating |
| JPS61151274A (en) * | 1984-12-25 | 1986-07-09 | Sumitomo Bakelite Co Ltd | Powder coating |
| US4734468A (en) * | 1986-02-28 | 1988-03-29 | Shell Oil Company | Epoxy resin composition |
| DE3622610A1 (en) * | 1986-07-05 | 1988-01-14 | Bayer Ag | LIQUID CRYSTALLINE DIGLYCIDYL COMPOUNDS, THEIR PRODUCTION AND USE IN HARDENABLE EPOXY BLENDS |
| JPH0618985B2 (en) * | 1987-06-03 | 1994-03-16 | 信越化学工業株式会社 | Epoxy resin composition |
-
1986
- 1986-12-05 JP JP61290161A patent/JPH0781098B2/en not_active Expired - Lifetime
-
1988
- 1988-06-02 CA CA000568485A patent/CA1329856C/en not_active Expired - Fee Related
- 1988-06-04 KR KR1019880006710A patent/KR960008473B1/en not_active IP Right Cessation
-
1994
- 1994-05-09 US US08/240,040 patent/US5455290A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR900000419A (en) | 1990-01-30 |
| JPH0781098B2 (en) | 1995-08-30 |
| KR960008473B1 (en) | 1996-06-26 |
| JPS63142070A (en) | 1988-06-14 |
| US5455290A (en) | 1995-10-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |