CN1210546A - 贮存稳定的环氧树脂基模塑粉 - Google Patents
贮存稳定的环氧树脂基模塑粉 Download PDFInfo
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- CN1210546A CN1210546A CN97192011A CN97192011A CN1210546A CN 1210546 A CN1210546 A CN 1210546A CN 97192011 A CN97192011 A CN 97192011A CN 97192011 A CN97192011 A CN 97192011A CN 1210546 A CN1210546 A CN 1210546A
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- molding powder
- powder
- coating
- epoxy
- adducts
- Prior art date
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- 239000000843 powder Substances 0.000 title claims abstract description 96
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- 239000003822 epoxy resin Substances 0.000 title claims description 10
- 229920000647 polyepoxide Polymers 0.000 title claims description 10
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000576 coating method Methods 0.000 claims abstract description 55
- 239000011248 coating agent Substances 0.000 claims abstract description 53
- 239000004593 Epoxy Substances 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 239000002245 particle Substances 0.000 claims abstract description 11
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- 238000010438 heat treatment Methods 0.000 claims description 11
- -1 dihydroxyphenyl propane diglycidyl ether compound Chemical class 0.000 claims description 10
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 9
- 238000003825 pressing Methods 0.000 claims description 9
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000002023 wood Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 5
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
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- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 229920003986 novolac Polymers 0.000 claims description 4
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 claims description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical group C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002118 epoxides Chemical group 0.000 claims description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
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- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- HWRRQRKPNKYPBW-UHFFFAOYSA-N 2,4-dimethylcyclohexan-1-amine Chemical compound CC1CCC(N)C(C)C1 HWRRQRKPNKYPBW-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- KNIBGFJYGWBIIV-UHFFFAOYSA-N 2-methyl-4-propylcyclohexan-1-amine Chemical compound CCCC1CCC(N)C(C)C1 KNIBGFJYGWBIIV-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- JCGWKDDAKPGTJK-UHFFFAOYSA-N 4-(4-aminocyclohexyl)sulfonylcyclohexan-1-amine Chemical compound C1CC(N)CCC1S(=O)(=O)C1CCC(N)CC1 JCGWKDDAKPGTJK-UHFFFAOYSA-N 0.000 description 1
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 1
- OZUBMBIDHPBIDL-UHFFFAOYSA-N 4-Propylcyclohexylamine Chemical compound CCCC1CCC(N)CC1 OZUBMBIDHPBIDL-UHFFFAOYSA-N 0.000 description 1
- QTKDDPSHNLZGRO-UHFFFAOYSA-N 4-methylcyclohexane-1,3-diamine Chemical compound CC1CCC(N)CC1N QTKDDPSHNLZGRO-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- 229920000965 Duroplast Polymers 0.000 description 1
- 235000009161 Espostoa lanata Nutrition 0.000 description 1
- 240000001624 Espostoa lanata Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AJBXRBRVQMZREG-UHFFFAOYSA-N OC(CC)(C1=CC=CC=C1)O.OC1=CC=C(C=C1)CCC Chemical compound OC(CC)(C1=CC=CC=C1)O.OC1=CC=C(C=C1)CCC AJBXRBRVQMZREG-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
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- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
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- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical class CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
- C08G59/184—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 using pre-adducts of epoxy compounds with curing agents with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
-
- 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
-
- 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
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/934—Powdered coating composition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Manufacturing & Machinery (AREA)
- Paints Or Removers (AREA)
- Dry Formation Of Fiberboard And The Like (AREA)
- Epoxy Resins (AREA)
Abstract
一种以加热和加压可固化的模塑粉,包括一种包含下列组分的机械混合物:a)分子中含平均一个以上环氧基团的、软化点高于60℃的一种粉状环氧化合物,b)一种粉状的脂族胺或N－杂环胺或者一种粉状的、由脂族、脂环族、芳脂族胺或N－杂环胺制成的含氨基基团的加合物;其中分子中含平均一个以上氨基基团且熔点或软化点高于60℃,以及任选地c)用于模塑粉的常用添加剂,组分a)和组分b)的微粒粒径小于200微米,这种模塑粉非常适于在对热敏感的底材上形成涂层,具体说是适用于制造粉末涂料。
Description
本发明涉及贮存稳定的、有高反应性的含胺(aminic)硬化剂的环氧树脂基模塑粉，并涉及该模塑粉在制备模塑制品或涂料(优选粉末涂料)方面的用途。
直到目前为止，制备环氧树脂基粉末涂料的常见方法还是采用挤出机。尤其是如Becker/Braun在“Kunststoffhandbuch”(Carl Hanserverlag Muchen Wien 1988)第10卷第13.10章，标题为粉末涂料的第1047-1058页，特别是第1051和1052页中所述的。所述制备方法包括将诸如环氧树脂、硬化剂及粉末涂料用常规添加剂(一般是流动性调节剂、颜料、填料及催化剂)的各组分研磨成粉末、经混合，然后在70-120℃(随混合物的组成和所用挤出机类型而定)的条件下挤出。选择温度时必须考虑到不能发生预交联，以免影响后续加工。挤出后，将挤出料冷却并将其研磨至粒径小于100微米。与机械混合物相比，如此制得的微粒包含所有混合的成份。采用已知的方法，通常有静电粉末喷涂或流化床涂布将涂料涂布在待涂的底材上。然后，所涂的粉末涂料在约130-240℃固化10-30分钟。具有低固化温度(如130℃)的粉末涂料的缺点有：需要15分钟以上较长的固化时间，粉末涂料在底材上的流动性差以及配制的粉末涂料有限的贮存稳定性。
欧洲专利0042759公开了一种用粉末涂料使底材着色的方法，该方法包括采用以加热和加压可固化的粉末涂料系统。公开的由环氧树脂和聚酯或环氧树脂和聚氨酯组成的粉末涂料在180℃的固化时间分别为3分钟或10分钟，但并不适于涂布对热敏感的底材(如纸板或木材)，且在低温缺乏足够的固化活性。
日本专利申请公开昭61-107980公开了一种涂布木材的方法，其中，由木材构成的底材首先涂以液态环氧树脂，然后在用加热和加压使涂层固化前，涂以粉状环氧树脂。液态和固态环氧树脂都含有催化硬化剂，如2-乙基-4-甲基咪唑，因此该类涂料体系的贮存稳定性是低的。
现已发现，如果将颗粒尺寸小于200微米、软化点(按DIN51920方法)高于60℃的粉状环氧树脂机械地与颗粒尺寸小于200微米，软化点高于60℃的粉状脂族胺或N-杂环胺或者与含氨基基团的粉状加合物相混合，不经过挤出，只是各组分的物理混合物，就可得到贮存稳定的，以加热和加压能快速固化的基于环氧树脂并含胺(aminic)硬化剂的粉末涂料，其中粉状的含氨基基团的加合物是由粉状的脂族、脂环族、芳脂族胺或N-杂环胺制成的。
因此，本发明涉及以加热和加压可固化的模塑粉，这种模塑粉是一种包括下列组分的机械混合物：
a)分子中含平均一个以上环氧基团的、软化点高于60℃的一种粉状环氧化合物，
b)一种粉状的脂族胺或N-杂环胺或者一种粉状的由脂族、脂环族、芳脂族胺或N-杂环胺制成的含氨基基团的加合物；其中分子中含平均一个以上氨基基团且熔点或软化点高于60℃，以及任选地
c)用于模塑粉的常用添加剂，
a)与b)的微粒颗粒尺寸小于200微米。
适用的粉状环氧化合物a)，都是环氧树脂技术中常用的固态环氧树脂，软化点高于60℃。这类环氧树脂是众所周知的，尤其是可从德国专利2838841和美国专利4175173中已知，其中某些树脂是可商购的。
优选的组分a)是一种芳族环氧树脂，通常是多元酚(优选双酚)的聚缩水甘油基醚或者是一种N-杂环环氧树脂，如乙内酰脲的二缩水甘油基化合物或氰尿酸的三缩水甘油基化合物。
优选采用的环氧树脂的环氧基含量为每千克0.5-12当量。可按已知方法，一般，通过与低于化学计量比的二元酚相反应可使这些软化点低于60℃的环氧树脂转变成具有较高软化点的高分子量环氧树脂。
特别优选的环氧树脂的软化点高于80℃，并任选地是2,2-双(4′-羟基苯基)丙烷(双酚A),2,2-双(3′,5′二溴-4′-羟基苯基)丙烷(四溴双酚A),双(4-羟基苯基)甲烷(双酚F)及可溶可熔的酚醛树脂的高级聚缩水甘油基醚，4,4′-二氨基二苯甲烷，4,4′-二氨基二苯基砜以及乙内酰胺和2,4,6-三羟基-1,3,5-三嗪(氰尿酸)的聚缩水甘油基衍生物，典型的是三缩水甘油基异氰酸酯。
对于制备新颖的模塑粉来说，采用双酚A，四溴双酚A、双酚F或可溶可熔酚醛树脂(如酚可溶酚醛或甲酚可溶酚醛树脂)的聚缩水甘油基化合物或三缩水甘油基异氰酸酯是优选的。也可采用所述聚缩水甘油基化合物的混合物。
在新颖模塑粉中用作组分b)的、熔点高于60℃的脂族胺或N-杂环胺也是众所周知的化合物，这些化合物包括一元、二元和多元胺。所述化合物可以是哌嗪，1,10-二氨基癸烷，1,12-二氨基十二烷。
存在于新颖模塑粉中的含氨基基团的加合物，是可根据已知方法由双环氧化合物与超过化学计量比的二元胺或多元胺反应而制得，优选的这种加合物是那些由二缩水甘油基醚衍生的化合物，通常，是由双酚二缩水甘油基醚衍生的化合物。通常用来制备含氨基基团加合物的脂族二元胺或多元胺是乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、丙烷-1,2-二胺、丙烷-1,3-二胺、六亚甲基-1,6-二胺、二亚丙基三胺或2,2,4-三甲基己烷-1,6-二胺。芳脂族二胺一般可以是1,4-双(氨基甲基)苯。适用的脂环族二胺一般是双(氨基甲基)环己烷、双(4-氨基环己基)甲烷，双(4-氨基环己基)砜、双(4-氨基甲基)二环戊二烯、2,2-双(4-氨基环己基)丙烷、双(4-氨基-3-甲基环己基)甲烷，2,2-双(4-氨基-3-甲基环己基)丙烷，1,4-二氨基环己烷，1,2-二氨基环已烷、1,3-二氨基-4-甲基环己烷或3-氨基甲基-3,5,5-三甲基环己胺(异佛尔酮二胺)。N-杂环二元胺或多元胺一般可以是哌嗪、N-2-氨基乙基哌嗪或4-氨基-2,2,6,6-四甲基哌啶。
新颖模塑粉中的组分b)优选为脂族胺或含氨基基团的加合物。
新颖模塑粉中的组分b)优选为一种含氨基基团的加合物，特别优选的是双酚A的二缩水甘油基醚化合物与乙二胺、二亚乙基三胺,1,2或1,4-二氨基环己烷或异佛尔酮二胺的加合物。
通常，新颖模塑粉中组分a)与组分b)的使用量约为等当量，即组分a)中的每一环氧当量对应于组分b)中与氨基氮原子结合的活泼氢为0.75-1.25当量。
新颖模塑粉也可含常规填料和环氧技术用增强材料。适用的填料有，例如，诸如石英粉、熔凝硅石、氧化铝、玻璃粉、云母、高岭土、白云石、石墨、炭黑，以及碳纤维和纺织纤维的无机填料和纤维填料。优选的填料是石英粉、熔凝硅石、氧化铝或白云石。适用的增强材料通常是玻璃纤维或碳纤维、天然材料(如木材或黄麻)纤维或木片。
本发明的模塑粉优选用作粉末涂料。对于这种优选的用途来说，向该新颖粉末涂料添加涂料工业常用的添加剂是可能的，这种添加剂一般是光稳定剂、着色剂，具体说是脱气剂、流动调节剂或颜料(如优选为Tio2)。
流动调节剂通常是聚缩醛类，如聚乙烯醇缩丁醛(MovitalRB30H，Hoechst提供)，聚乙二醇、聚乙烯吡咯烷酮、甘油、丙烯酸共聚物(如Modaflow或AcrylronMFP，分别由Monsanto和protex提供)。脱气剂优选为苯偶姻。
新颖模塑粉可通过下述方法制得：或分别研磨组分a)和组分b)至颗粒尺寸小于200微米，用筛分法除去颗粒尺寸大于200微米的微粒，然后将粉状组分a)与组分b)在混合设备中经机械混合以致得到物理混合物；或先机械地混合组分a)与组分b)，然后再一起研磨及过筛混合物。
各组分可在常用的实验室用混合器，通常在球磨机中，在实验室多用途混合器或Rhoenrad混合器中进行混合。
可在制备新颖模塑粉期间将添加剂c)添加到组分a)或组分b)中，或在研磨及过筛前或在研磨及过筛后添加到两组分中。
在颜料用作添加剂的情况下，优选的是，在研磨前将颜料添加到组分a)和/或组分b)中，接着在如Buss蜗杆捏合机中挤出成组分a)与颜料的混合物或组分b)与颜料的混合物。然后，经研磨和经过筛的组分a)或组分b)挤出物可用于制备物理混合物。
该新颖模塑粉可用来制造模压制品及涂料，采用加热和加压可使模塑粉固化。这种新颖模塑粉优选用于刨花板的制造。
由该新颖模塑粉制造的模压制品优选含填料或增强剂。该新颖模塑粉优选用于制造刨花板或模塑件，其制造方法是：将木片或天然物质纤维与这种新颖模塑粉混合或以模塑粉充填，然后在模压机中加热，将它们模压成型为刨花板或模塑件。因此，本发明也涉及由新颖模塑粉制得的模压制品，尤其是刨花板或模塑件。
由于该新颖模塑粉是有高度反应性的并有在加热和加压条件下能快速固化的优点，因此，该新颖模塑粉优选用作粉末涂料，尤其用于涂布对热敏感的底材，如纸张、纸板、木材、热塑性塑料或硬塑料。于是，本发明也涉及由新颖模塑粉构成的粉末涂料。
可通过筛分、喷淋或静电粉末喷涂将新颖模塑粉涂布到底材上制成涂层。然后，用耐热箔覆盖在涂有粉末涂料的底材表面上，或将防粘剂(antisize)涂布到模压机上。该粉末涂层可在稍加压下、在加热的模压机中实现交联。交联时间与所涂粉末涂层的厚度无关，通常在约130℃和压力约10牛顿/厘米2条件下所需交联时间少于3分钟。对于粉末静电喷涂来说，优选采用颗粒尺寸小于100微米的模塑粉。
如果需要，可采用一种可加热的压辊或可加热的金属带来固化粉末涂层，这样可实现连续涂布加工。
对于本发明的另一方面，本发明涉及由新颖模塑粉制成的涂层。
如一开始所提及的，新颖模塑粉的特征是：一方面具有高的反应性，但另一方面在室温或高至40℃下又具有长的贮存稳定性。由新颖模塑粉制得的模压制品和涂层具有极好的机械性能，而且，该涂层在底材上有很好的粘附强度。
下列化合物用于实施例中：
环氧树脂A：80克双酚A二缩水甘油基醚与20克环氧含量为1.9当量/千克、软化点(按照DIN51920)为95℃的酚可溶可熔酚醛环氧树脂的混合物。
环氧树脂B：环氧含量为1.7当量/千克、软化点(按DIN51920)为80-90℃的双酚A二缩水甘油基醚。
环氧树脂C：环氧含量为4.5当量/千克、软化点(按DIN51920)为94℃的甲酚可溶酚醛环氧树脂。
硬化剂Ⅰ、含氨基基团的加合物，其中胺含量为3.5当量/千克、软化点(按DIN51920)为94℃，是由1000克环氧含量为2.1当量/千克的双酚A二缩水甘油基醚树脂与485克乙二胺在惰性有机溶剂中反应，随后经蒸馏以除去溶剂和过量胺后而制得的。
硬化剂Ⅱ：含氨基基团的加合物，其中胺含量为3.5当量/千克，软化点(按DIN51920)为100℃，是由1000克环氧含量为2.1当量/千克的双酚A二缩水甘油基醚树脂与1400克1,2-二氨基环己烷在惰性有机溶剂中反应，随后经蒸馏以除去溶剂和过量胺后而制得的。
实施例1
以已知的标准方法，将环氧树脂A与硬化剂Ⅰ分别研磨成细微粉末，用筛子筛去颗粒尺寸大于100微米的粗组分。将735克粉状环氧树脂A与265克粉状硬化剂Ⅰ在实验室用混合器(Rhoenrad混合器)中进行物理混合。待用的粉末在130℃的胶凝时间为21秒。该粉末混合物在40℃下贮存6个月，胶凝时间没有明显的改变。
将粉末混合物以静电粉末喷涂法喷涂在预先用水弄湿的木材(山毛榉)表面上。经粉末涂料涂布过的木材表面覆盖一耐热箔(Tedlar，由Dupont制造)。在压力约10牛/厘米2加热至130℃的模压机中使粉末涂层交联2分30秒钟。
所得涂膜具有下列性能：
膜厚度：约50微米，
流动性(目视评价)：很好(膜表面没有纹理)，
冲击强度*)，正面(20厘米·千克)：很好(涂层没有出现碎屑片)，
划格法附着力：很好(涂层没有从木材上掉屑)。
*)向正面，从20厘米的高度向已涂布的木材下落1千克冲锤。
实施例2
将530克环氧树脂B与470克二氧化钛在75℃的挤出机(型号：蜗杆捏合机，由Buss,Pratteln,瑞士提供)中均质化。用已知的标准方法分别研磨挤出的物料和硬化剂成精细粉末。用筛分法除去颗粒尺寸大于100微米的粗粒物料。
用实验室用混合器(型号：Rhoenrad混合器)混合1000克粉状挤出物料与175克粉状硬化剂Ⅰ。待用的粉料在130℃的胶凝时间为35秒。将该粉末混合物筛在MDF板(MDF=中密度纤维板，由木质颗粒与硬质塑料粘合剂组成的经压制成的中密度纤维板)上，并在经粉末涂料涂布的木材表面覆盖Tedlar箔。在压力为约10牛/厘米2、加热至130℃的模压机中使粉末涂层交联2分30秒钟。
所得的涂膜具有下列性能：
膜厚度：约60微米，流动性(目视评价)：很好(膜表面没有纹理)，
冲击强度按实施例1方法，正面(20厘米·千克)：很好(涂层没有出现碎屑片)，
划格法附着力：很好(涂层没有从木材上掉屑)。
实施例3
完全按与实施例1相同的方法，混合223克环氧树脂C与192克硬化剂Ⅰ制成粉末涂料。待用的粉料在130℃的胶凝时间为17秒。将粉末混合物筛在山毛榉上并用Tedlar箔覆盖。在压力为10牛/厘米2、加热至130℃的模压机中使粉末涂层交联90秒钟。
所得的涂膜具有下列性能：
膜厚度：约130微米，
流动性(目视评价)：很好(膜表面没有纹理)，
冲击强度按实施例1方法，正面(20厘米·千克)：很好(涂层没有出现碎屑片)，
丙酮试验*)：不会划出痕迹。
*)将以丙酮浸湿的棉球放置在涂层表面上1分钟，随后试验涂层表面是否能用指甲划痕。
实施例4
完全按与实施例1相同的方法，混合534克环氧树脂C与455克硬化剂Ⅱ制成粉末涂料。待用的粉料在130℃的胶凝时间为34秒。将粉末混合物筛在山毛榉上并用Tedlar箔覆盖，在压力约为10牛/厘米2、加热至130℃的模压机中使粉末涂层交联3分钟。
所得涂膜具有下列性能：
膜厚度：约170微米，
流动性(目视评价)：很好(膜表面没有纹理)，
冲击强度按实施例1方法，正面(20厘米·千克)：很好(涂层没有出现碎屑片)，
丙酮试验按实施例3进行：不会划出痕迹。
实施例5
用已知标准方法分别将环氧树脂A和硬化剂Ⅰ研磨成精细粉末，用筛分法除去粒径超过100微米的粗粒。该粉末进一步按下法处理：
用实验室用混合器混合735克粉状环氧树脂A与265克粉状硬化剂Ⅰ。待用的粉料在130℃的胶凝时间为21秒。为制造刨花板，在实验室用混合器中将含水量约7％(重量)的834克木片与68.2克待用的粉料混合20分钟。随后，将798克该粉料混合物洒在内表面积为625厘米2的方形木质模中，并用一冲压件将粉料混合物预压成方形模压制品。一旦除去木模，经预压的模压制品就自动地在模压机(型号KHE50-40-40,BucherGuver AG提供)中在160℃压制温度下充分固化12分钟。由此制成的刨花板的厚度为20毫米。
用5个刨花板试样按照DIN52365方法测定其横向抗拉强度，得到的平均强度值为0.42牛/毫米2。
Claims (10)
1．一种以加热和加压可固化的模塑粉，包括一种包含下列组分的机械混合物：
a)分子中含平均一个以上环氧基团的、软化点高于60℃的一种粉状环氧化合物，
b)一种粉状的脂族胺或N-杂环胺或者一种粉状的由脂族、脂环族、芳脂族胺或N-杂环胺制成的含氨基基团的加合物；其中分子中含平均一个以上氨基基团且熔点或软化点高于60℃，以及任选地
c)用于模塑粉的常用添加剂，a)与b)的微粒颗粒尺寸小于200微米。
2．根据权利要求1的模塑粉，其中组分a)是芳族或N-杂环环氧树脂。
3．根据权利要求1的模塑粉，其中组分a)是双酚二缩水甘油基醚或三缩水甘油基异氰酸酯。
4．根据权利要求1的模塑粉，其中组分a)是双酚A、四溴双酚A、双酚F或可溶可熔酚醛树脂的聚缩水甘油基醚或三缩水甘油基异氰酸酯。5．根据权利要求1的模塑粉，其中组分b)是一种脂族胺或一种含氨基基团的加合物。
6．根据权利要求1的模塑粉，其中组分b)是一种含氨基基团的加合物。
7．根据权利要求6的模塑粉，其中组分b)是双酚A二缩水甘油基醚化合物与乙二胺、二亚乙基三胺、1,2-或1,4-二氨基环己烷或异佛尔酮二胺的一种含氨基加合物。
8．根据权利要求1的模塑粉经加热和加压制成的模压制品。
9．根据权利要求8的模压制品包含作为增强材料的木片或天然物质纤维，并将该增强材料模压成刨花板或模塑件。
10．一种以加热和加压可固化的粉末涂料包含根据权利要求1的模塑粉。
11．由根据权利要求10粉末涂料制成的、以加热和加压可固化的一种涂层。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH27796 | 1996-02-02 | ||
| CH277/96 | 1996-02-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1210546A true CN1210546A (zh) | 1999-03-10 |
| CN1093146C CN1093146C (zh) | 2002-10-23 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97192011A Expired - Fee Related CN1093146C (zh) | 1996-02-02 | 1997-01-23 | 在热敏感的底材上形成涂层的方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6165558A (zh) |
| EP (1) | EP0877769B1 (zh) |
| JP (1) | JP4026084B2 (zh) |
| KR (1) | KR19990082069A (zh) |
| CN (1) | CN1093146C (zh) |
| BR (1) | BR9707255A (zh) |
| CA (1) | CA2242928A1 (zh) |
| DE (1) | DE69712314T2 (zh) |
| ES (1) | ES2174214T3 (zh) |
| TW (1) | TW494127B (zh) |
| WO (1) | WO1997028203A1 (zh) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5714206A (en) * | 1996-05-06 | 1998-02-03 | Morton International, Inc. | Two component powder coating system and method for coating wood therewith |
| US6437045B1 (en) * | 1999-11-10 | 2002-08-20 | Vantico Inc. | Powder coating of carboxyl polyester or (poly)methacrylate and cycloaliphatic polyepoxide |
| EP1391490A1 (en) * | 2002-08-23 | 2004-02-25 | Vantico Gmbh | Modified epoxy resins for triboelectric coating processes |
| IL153811A0 (en) * | 2003-01-06 | 2003-07-31 | Bromine Compounds Ltd | Compositions for the preservation of timber |
| US20040236037A1 (en) * | 2003-05-19 | 2004-11-25 | December Timothy S. | Particulate coatings having improved chip resistance, UV durability, and color stability |
| GB0423349D0 (en) * | 2004-10-21 | 2004-11-24 | Hexcel Composites Ltd | Fibre reinforced assembly |
| TW201118129A (en) * | 2009-11-27 | 2011-06-01 | Stone & Resource Ind R & D Ct | Anti-yellowing epoxy resin composition for fixing stone material and its application |
| FR2967161B1 (fr) * | 2010-11-09 | 2014-02-28 | Faurecia Interieur Ind | Nouveaux oligomeres, leur procede de preparation et leur utilisation pour fluidifier et/ou ameliorer la stabilite de compositions polymeriques |
| US10662280B2 (en) | 2015-08-07 | 2020-05-26 | Sika Technology Ag | Amine for low-emission epoxy resin compositions |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE629380A (zh) * | 1962-03-09 | |||
| NL134842C (zh) * | 1962-06-08 | |||
| US4022946A (en) * | 1973-10-23 | 1977-05-10 | Pvo International Inc. | Method for coating wet surfaces or surfaces immersed in water |
| GB1588047A (en) * | 1977-09-09 | 1981-04-15 | Ciba Geigy Ag | Acid esters of trimellitic acid and their use as hardeners for epoxide resins |
| DE3064094D1 (en) * | 1979-05-08 | 1983-08-18 | Ciba Geigy Ag | Crystalline epoxy resin based one component systems and their application |
| IE51301B1 (en) * | 1980-06-24 | 1986-11-26 | Sonneborn & Rieck Ltd | Process for powder coating substrates |
| US4526940A (en) * | 1982-06-07 | 1985-07-02 | Ciba-Geigy Corporation | Hydroxyl terminated polyfunctional epoxy curing agents |
| US4637954A (en) * | 1984-08-08 | 1987-01-20 | Nippon Gakki Seizo Kabushiki Kaisha | Resin-treated woody material |
| GB8824391D0 (en) * | 1988-10-18 | 1988-11-23 | Ciba Geigy Ag | Compositions |
| IT1243350B (it) * | 1990-07-18 | 1994-06-10 | Hoechst Italia | Procedimento per il rivestimento di materiali termosensibili con vernice in polvere |
| US5721052A (en) * | 1996-05-06 | 1998-02-24 | Morton International, Inc. | Textured epoxy powder coating compositions for wood substrates and method of coating wood therewith |
| US5714206A (en) * | 1996-05-06 | 1998-02-03 | Morton International, Inc. | Two component powder coating system and method for coating wood therewith |
| US5686185A (en) * | 1996-06-28 | 1997-11-11 | Morton International, Inc. | Disbondment resistant epoxy powder coating composition |
-
1997
- 1997-01-23 CN CN97192011A patent/CN1093146C/zh not_active Expired - Fee Related
- 1997-01-23 JP JP52727797A patent/JP4026084B2/ja not_active Expired - Fee Related
- 1997-01-23 EP EP97901591A patent/EP0877769B1/en not_active Expired - Lifetime
- 1997-01-23 KR KR1019980705791A patent/KR19990082069A/ko not_active Application Discontinuation
- 1997-01-23 US US09/101,789 patent/US6165558A/en not_active Expired - Lifetime
- 1997-01-23 BR BR9707255A patent/BR9707255A/pt not_active IP Right Cessation
- 1997-01-23 WO PCT/EP1997/000297 patent/WO1997028203A1/en not_active Application Discontinuation
- 1997-01-23 CA CA002242928A patent/CA2242928A1/en not_active Abandoned
- 1997-01-23 DE DE69712314T patent/DE69712314T2/de not_active Expired - Lifetime
- 1997-01-23 ES ES97901591T patent/ES2174214T3/es not_active Expired - Lifetime
- 1997-01-31 TW TW086101104A patent/TW494127B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| CA2242928A1 (en) | 1997-08-07 |
| ES2174214T3 (es) | 2002-11-01 |
| BR9707255A (pt) | 1999-04-06 |
| JP2000504369A (ja) | 2000-04-11 |
| DE69712314T2 (de) | 2002-11-21 |
| CN1093146C (zh) | 2002-10-23 |
| DE69712314D1 (de) | 2002-06-06 |
| EP0877769B1 (en) | 2002-05-02 |
| JP4026084B2 (ja) | 2007-12-26 |
| WO1997028203A1 (en) | 1997-08-07 |
| KR19990082069A (ko) | 1999-11-15 |
| US6165558A (en) | 2000-12-26 |
| TW494127B (en) | 2002-07-11 |
| EP0877769A1 (en) | 1998-11-18 |
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