ZA200104729B - Hydrophobic epoxide resin system. - Google Patents
Hydrophobic epoxide resin system. Download PDFInfo
- Publication number
- ZA200104729B ZA200104729B ZA200104729A ZA200104729A ZA200104729B ZA 200104729 B ZA200104729 B ZA 200104729B ZA 200104729 A ZA200104729 A ZA 200104729A ZA 200104729 A ZA200104729 A ZA 200104729A ZA 200104729 B ZA200104729 B ZA 200104729B
- Authority
- ZA
- South Africa
- Prior art keywords
- composition according
- component
- formula
- polysiloxane
- acid
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims description 30
- 229920000647 polyepoxide Polymers 0.000 title claims description 30
- 230000002209 hydrophobic effect Effects 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 84
- -1 polysiloxane Polymers 0.000 claims description 54
- 229920001296 polysiloxane Polymers 0.000 claims description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 235000012239 silicon dioxide Nutrition 0.000 claims description 23
- 239000000843 powder Substances 0.000 claims description 21
- 239000010453 quartz Substances 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 15
- 150000008064 anhydrides Chemical class 0.000 claims description 13
- 239000003921 oil Substances 0.000 claims description 12
- 235000019198 oils Nutrition 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000012042 active reagent Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000000945 filler Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000011810 insulating material Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 4
- 238000006735 epoxidation reaction Methods 0.000 claims description 4
- 239000000944 linseed oil Substances 0.000 claims description 4
- 235000021388 linseed oil Nutrition 0.000 claims description 4
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims description 4
- 239000003549 soybean oil Substances 0.000 claims description 4
- 235000012424 soybean oil Nutrition 0.000 claims description 4
- IUMSDRXLFWAGNT-UHFFFAOYSA-N Dodecamethylcyclohexasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 IUMSDRXLFWAGNT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 claims description 2
- GRJRKPMIRMSBNK-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-ol Chemical compound OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F GRJRKPMIRMSBNK-UHFFFAOYSA-N 0.000 claims 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 claims 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000413 hydrolysate Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 description 21
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- 239000004848 polyfunctional curative Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000005266 casting Methods 0.000 description 10
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 10
- 239000012212 insulator Substances 0.000 description 10
- 239000000463 material Substances 0.000 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 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 229910002012 Aerosil® Inorganic materials 0.000 description 7
- 230000007246 mechanism Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000005336 cracking Methods 0.000 description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 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 4
- 150000003972 cyclic carboxylic anhydrides Chemical class 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000009832 plasma treatment Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- FMZUHGYZWYNSOA-VVBFYGJXSA-N (1r)-1-[(4r,4ar,8as)-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl]ethane-1,2-diol Chemical compound C([C@@H]1OC(O[C@@H]([C@@H]1O1)[C@H](O)CO)C=2C=CC=CC=2)OC1C1=CC=CC=C1 FMZUHGYZWYNSOA-VVBFYGJXSA-N 0.000 description 3
- MFEWNFVBWPABCX-UHFFFAOYSA-N 1,1,2,2-tetraphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 MFEWNFVBWPABCX-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000002993 cycloalkylene group Chemical group 0.000 description 3
- 230000006735 deficit Effects 0.000 description 3
- 229940087101 dibenzylidene sorbitol Drugs 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- WXQZLPFNTPKVJM-UHFFFAOYSA-N 4-[(4-hydroxycyclohexyl)methyl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1CC1CCC(O)CC1 WXQZLPFNTPKVJM-UHFFFAOYSA-N 0.000 description 2
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 2
- YWVFNWVZBAWOOY-UHFFFAOYSA-N 4-methylcyclohexane-1,2-dicarboxylic acid Chemical compound CC1CCC(C(O)=O)C(C(O)=O)C1 YWVFNWVZBAWOOY-UHFFFAOYSA-N 0.000 description 2
- SVLTVRFYVWMEQN-UHFFFAOYSA-N 5-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound CC1CC(C(O)=O)C(C(O)=O)C=C1 SVLTVRFYVWMEQN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 229920002732 Polyanhydride Polymers 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- YXEBFFWTZWGHEY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohex-3-en-1-yl]methanol Chemical compound OCC1(CO)CCC=CC1 YXEBFFWTZWGHEY-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000003915 air pollution Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 2
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 2
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- 229910052760 oxygen Inorganic materials 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
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- 230000003019 stabilising effect Effects 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
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- 238000011282 treatment Methods 0.000 description 2
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- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
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- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
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- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000000206 moulding compound Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021290 n-3 DPA Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- ZMVMYBGDGJLCHV-UHFFFAOYSA-N n-methyl-4-[[4-(methylamino)phenyl]methyl]aniline Chemical compound C1=CC(NC)=CC=C1CC1=CC=C(NC)C=C1 ZMVMYBGDGJLCHV-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000001367 organochlorosilanes Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000001944 prunus armeniaca kernel oil Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Chemical class 0.000 description 1
- 239000011669 selenium Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical class [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- GSANOGQCVHBHIF-UHFFFAOYSA-N tetradecamethylcycloheptasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 GSANOGQCVHBHIF-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/40—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes epoxy resins
-
- 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
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/549—Silicon-containing compounds containing silicon in a ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/46—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes silicones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Organic Insulating Materials (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Description
" HE/K-21888/A 200147239
Hydrophobic epoxide resin system
The present invention relates to a composition comprising an epoxy resin, various poly- siloxanes and fluorinated compounds, to crosslinked products obtainable by curing such a composition and to the use of such a composition as electrical insulating material.
Epoxy resins are frequently used as electrical insulating material on account of their good mechanical properties and their high specific resistance. Cycloaliphatic epoxy resins are especially suitable for outdoor applications because of their high resistance to weathering, ® but the problem arises, especially in regions having high levels of precipitation and air pollution, that a conductive dirt/water layer can form on the surface of the insulator, which leads to leakage currents and arcing and may have consequences ranging from damage to the insulator up to total failure. Even only slightly soiled epoxy-based insulators can undergo a rise in surface conductivity if the surface becomes eroded by weathering in the course of time and the water is better able to wet the resulting roughened layer.
As disclosed in US Patent 3 926 885, epoxy resins can be provided with hydrophobic properties by the addition of polysiloxane/polyether copolymers and OH-terminated polysiloxanes, but the adhesion of the resulting material to metal is not sufficient for all applications. 9 JP-A 2-305454 describes epoxy resin mixtures having a high degree of stability towards moisture which, in addition to comprising an epoxy novolak and a phenolic resin, also comprise small amounts of a cyclic dimethylsiloxane. Although, in those compositions, the corrosion caused by binding of water on the surface is largely prevented, a hydrophobicity effect sufficient for use as an insulator is not achieved with such systems.
WO 98/32138 describes a resin system suitable as electrical insulating material that is based on curable mixtures of epoxy resins and specific silicone oligomers having terminal glycidyl groups. As a result of the curing, the silicone oligomers become part of the crosslinked structure that is formed, so that known properties of silicones, such as hydrophobicity and B good resistance to weathering, can be imparted to the cured material. A disadvantage is the use of expensive commercially available silicone oligomers and a poor hydrophobicity transfer effect.
It has now been found that compositions comprising an epoxy resin, at least two specific polysiloxanes and a non-ionic, fluoroaliphatic surface-active reagent are able to yield storage-stable emulsions that in the fully cured state have a pronounced hydrophobicity transfer effect and recovery effect.
The present invention relates to a composition comprising (a) an epoxy resin, (b) an OH-terminated polysiloxane, (c) a cyclic polysiloxane and ® (d) a non-ionic, fluoroaliphatic surface-active reagent.
The amounts of components (a) to (c) in the compositions according to the invention can vary within wide limits.
Preference is given to compositions comprising, based on the total composition (a), (b), (c) and (d), from 77.0 to 97.99 % by weight, especially from 86.0 to 96.95 % by weight, component (a), from 1.0 to 10.0 % by weight, especially from 2.0 to 6.0 % by weight, component (b), from 1.0 to 10.0 % by weight, especially from 1.0 to 5.0 % by weight, component (c) and from 0.01 to 3.0 % by weight, especially from 0.05 to 3.0 % by weight, component (d), the sum of components (a), (b), (c) and (d) being 100 % by weight. ® As component (a) of the compositions according to the invention there are suitable any type of epoxide that contains at least one glycidyl or B-methylgiycidyl group, a linear alkylene oxide group or a cycloalkylene oxide group.
Examples of suitable epoxy resins are polyglycidyl and poly(B3-methylglycidyl) ethers obtain- able by reaction of a compound containing at least two free alcoholic and/or phenolic hydroxyl groups per molecule with epichlorohydrin or B-methylepichlorohydrin under alkaline conditions, or alternatively in the presence of an acid catalyst with subsequent alkali treat- - ment.
Suitable starting compounds for the preparation of such glycidy! or -methyiglycidyl ethers are, for example, acyclic alcohols, such as ethylene glycol, diethylene glycol and higher poly(oxyethylene) glycols, propane-1,2-diol and poly(oxypropylene) glycols, propane-1,3-diol,
butane-1,4-diol, poly(oxytetramethylene) glycols, pentane-1,5-diol, hexane-1,6-diol, hexane- 2,4,6-triol, glycerol, 1,1,1-trimethylolpropane, pentaerythritol or sorbitol, cycloaliphatic alcohols, such as resorcitol, quinitol, bis(4-hydroxycyclohexyl)methane, 2,2-bis(4-hydroxy- cyclohexyl)propane and 1,1-bis(hydroxymethyl)cyclohex-3-ene, and alcohols having aromatic nuclei, such as N,N-bis(2-hydroxyethyl)aniline and p,p'-bis(2-hydroxyethylamino)diphenyl- methane.
Further suitable dihydroxy compounds for the preparation of glycidyl or f—methyliglycidy! ethers are mononuclear phenols, such as resorcinol and hydroquinone, polynuclear phenols, such as bis(4-hydroxyphenyl)methane, 4,4-dihydroxydiphenyl, bis(4-hydroxyphenyl)sulfone, ® 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)propane (bisphenol A) and 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane, and novolaks, for example phenol and cresol novolaks.
Polyglycidyl and poly(B-methylglycidyl) esters are obtainable by reaction of a compound containing two or more carboxylic acid groups per molecule with epichlorohydrin, glycerol dichlorohydrin or B-methylepichlorohydrin in the presence of alkali. Such polyglycidyl esters can be derived from aliphatic polycarboxylic acids, e.g. oxalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid or dimerised or trimer- ised linoleic acid, from cycloaliphatic polycarboxylic acids, such as tetrahydrophthalic acid, 4- methyltetrahydrophthalic acid, hexahydrophthalic acid and 4-methylhexahydrophthalic acid, ¢ and from aromatic polycarboxylic acids, such as phthalic acid, isophthalic acid and terephthalic acid.
Further epoxides suitable as component (a) are poly(N-glycidyl) compounds, for example the products obtainable by dehydrochlorination of the reaction products of epichlorohydrin and amines containing at least two amino hydrogen atoms, such as aniline, n-butylamine, bis(4- aminophenyl)methane and bis(4-methyl-aminophenyl)methane. Also included are triglycidyl isocyanurate as well as N,N'-diglycidyl derivatives of cyclic alkyleneureas, such as ethylene- urea and 1,3-propyleneurea and hydantoins, such as 5,5-dimethylhydantoin. =
Poly(S-glycidy!) compounds, for example the di-S-glycidyl derivatives of dithiols, such as ethane-1,2-dithiol and bis(4-mercaptomethylphenyl) ether, are likewise suitable.
Preferably the compositions comprise as component (a) a cycloaliphatic epoxy resin or an epoxidation product of a natural unsaturated oil or a derivative thereof.
The term "cycloaliphatic epoxy resin” in the context of this invention denotes any epoxy resin having cycloaliphatic structural units, that is to say it includes both cycloaliphatic glycidyl compounds and p-methylglycidyl compounds as well as epoxy resins based on cyclo- alkylene oxides.
Suitable cycloaliphatic glycidyl compounds and B-methyiglycidyl compounds are the glycidyl esters and B-methyliglycidy! esters of cycloaliphatic polycarboxylic acids, such as tetrahydro- phthalic acid, 4-methyltetrahydrophthalic acid, hexahydrophthalic acid, 3-methylhexahydro- ® phthalic acid and 4-methylhexahydrophthalic acid.
Further suitable cycloaliphatic epoxy resins are the diglycidyl ethers and B-methylglycidy! ethers of cycloaliphatic alcohols, such as 1,2-dihydroxycyclohexane, 1,3-dihydroxycyclo- hexane and 1,4-dihydroxycyclohexane, 1,4-cyclohexanedimethanol, 1,1-bis(hydroxymethyl)- cyclohex-3-ene, bis(4-hydroxycyclohexyl)methane, 2,2-bis(4-hydroxycyclohexyl)propane and bis(4-hydroxycyclohexyl)sulfone.
Examples of epoxy resins having cycloalkylene oxide structures are bis(2,3-epoxycyclo- pentyl) ether, 2,3-epoxycyclopentylglycidyl ether, 1,2-bis(2,3-epoxycyclopentyl)ethane, vinyl cyclohexene dioxide, 3,4-epoxycyciohexyimethyl 3',4'-epoxycyclohexanecarboxylate, 3,4- ® epoxy-6-methylcyclohexylmethyl 3' 4'-epoxy-6'-methylcyclohexanecarboxylate, bis(3,4- epoxycyclohexylmethyl) adipate and bis(3,4-epoxy-6-methylcyclohexylmethyl) adipate.
Preferred cycloaliphatic epoxy resins are bis(4-hydroxycyclohexyl)methanediglycidyl ether, 2 2-bis(4-hydroxycyclohexyl)propanediglycidyl ether, tetrahydrophthalic acid diglycidyl ester, 4-methyltetrahydrophthalic acid diglycidyl ester, 4-methylhexahydrophthalic acid diglycidyl ester, and especially hexahydrophthalic acid diglycidyl ester and 3,4-epoxycyclohexyimethyl 3',4'-epoxycyclohexanecarboxylate.
As component (a) it is also possible to use in the compositions according to the invention epoxidation products of unsaturated fatty acid esters. ltis preferable to use epoxy-contain- ing compounds derived from mono- and poly-fatty acids having from 12 to 22 carbon atoms and an iodine number of from 30 to 400, for example lauroleic acid, myristoleic acid, i palmitoleic acid, oleic acid, gadoleic acid, erucic acid, ricinoleic acid, linoleic acid, linolenic acid, elaidic acid, licanic acid, arachidonic acid and clupanodonic acid.
For example, there are suitable the epoxidation products of soybean oil, linseed oil, perilla oil, tung oil, oiticica oil, safflower oil, poppyseed oil, hemp oil, cottonseed oil, sunflower oil, rapeseed oil, polyunsaturated triglycerides, triglycerides from euphorbia plants, groundnut oil, : olive oil, olive kernel oil, almond oil, kapok oil, hazelnut oil, apricot kernel oil, beechnut oil, lupin oil, maize oil, sesame oil, grapeseed oil, lallemantia oil, castor oil, herring oil, sardine oil, menhaden oil, whale oil, tall oil and derivatives thereof.
Also suitable are higher unsaturated derivatives that can be obtained by subsequent ® dehydrogenation reactions of those oils.
The olefinic double bonds of the unsaturated fatty acid radicals of the above-mentioned compounds can be epoxidised in accordance with known methods, for example by reaction with hydrogen peroxide, optionally in the presence of a catalyst, an alkyl hydroperoxide or a per acid, for example performic acid or peracetic acid.
Within the scope of the invention, both the fully epoxidised oils and the partially epoxidised derivatives that still contain free double bonds can be used as component (a).
Especially preferred as component (a) are epoxidised soybean oil and epoxidised linseed oil. ® The OH-terminated polysiloxanes in accordance with component (b) can be prepared according to known methods, for example by hydrolysis of the corresponding organochloro- silanes and subsequent polycondensation of the silanols, there generally being formed poly- siloxane mixtures having molecular masses of from 1000 to 150 000 g/mol. A number of such OH-terminated polysiloxanes are commercially available.
In the compositions according to the invention it is preferable to use liquid polysiloxanes.
There is preferably used a polysitoxane of formuta —-
Ri
HO 7° H n,
R, n wherein R, and R, are each independently of the other C;-Cygalkyl, C5-Cq4aryl or Ce-Coy- aralkyl and n is an average value of from 3 to 60, especially from 4 to 20.
Alkyl includes, for example, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert- butyl and the various isomeric pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, ® tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecy! and eicosyl groups.
Aryl as R, or R, contains preferably from 6 to 14 carbon atoms and may be, for example, phenyl, tolyl, pentalinyl, indenyl, naphthyl, azulinyl and anthryl.
Aralkyl as R; or R; contains preferably from 7 to 12 carbon atoms and especially from 7 to 10 carbon atoms. It may be, for example, benzyl, phenylethyl, 3-phenylpropyl, a-methyibenzyl, 4-phenylbutyl or a,a-dimethylbenzyl.
Special preference is given to polysiloxanes of formula | wherein Ry and R; are each independently of the other methyl, ethyl or phenyl.
Especially preferred as component (b) are polysiloxanes of formula | wherein Ry and R, are ® methyl and n = 4 to 20.
The cyclic polysiloxanes in accordance with component (c) are likewise known to the person skilled in the art and can be prepared according to known methods.
There is preferably used as component (c) a cyclic polysiloxane of formula Il
R,
Si— Qt (Ih, a
R, m wherein R; and R, are each independently of the other C4-Cygalkyl, Cs-Cysaryl or Cg-Co,- aralkyl and m is an integer from 3 to 12. i}
Alkyl, aryl and aralkyl in formula (ll) have the same definitions as the corresponding groups according to formula (1).
Preferred as component (c) are cyclic polysiloxanes of formula Il wherein Ry and R; are each independently of the other methyl, ethyl or phenyl and m is an integer from 3 to 8.
Very especially, Ry and R, are methyl and m is an integer from 6 to 8.
As described in J. Am. Chem. Soc. 68, 358 (1946), such cyclic polysiloxanes can be isolated ® from the product mixture formed on hydrolysis of the corresponding dialkyl-, diaryl- or diaralkyl-dichlorosilanes.
Especially preferred as component (c) are the commercially available compounds octa- methylcyclotetrasiloxane (m = 4), decamethylcyclopentasiloxane (m = 5) and especially dodecamethylcyclohexasiloxane (m = 6) and also hydrolysates of dimethylidichlorosilane, especially undistilled hydrolysates, since they have higher contents of cyclic polysiloxanes having the preferred ring size m = 6 to 8, and hence in addition to dodecamethylcyclohexa- siloxane also tetradecamethylcycloheptasiloxane (m = 7) and hexadecamethylcycloocta- siloxane (m = 8).
As surface-active reagent in the form of component (d) of the compositions according to the
J invention there are suitable derivatives of non-ionic, perfluorinated polyalkylenes, such as perfluorinated polyoxyalkylenes. Preference is given to compounds of a combination of a perfluorinated aliphatic alkyl unit R¢ with a hydrocarbon unit R, in which the latter contains at least one, preferably oxygen-containing, mono- or di-valent polar functional group, e.g. -OH, -COOH, -COOR, -COO-, -CO-, -O-.
Suitable compounds are alkoxylated, especially ethoxylated, perfluorinated fatty acid derivatives, for example:
Rf -COO-(CH,CH,0)-R (1m ” or
Rf -(CH,CH,O)m-R (IV),
wherein m = 1 to 200, Ry is a linear or branched perfluorinated alkyl having from 2 to 22 carbon atoms and R = H, C4-Cgalkyl or Ry.
It is preferable to use compounds of formula (lil) or (IV) in which the molecular mass according to the theoretical empirical formula is only from 200 to 10 000, especially from 300 to 8000.
Preferred compounds are, for example, F3C-(CF3)s-(CH,CH,0)-H = 1,1,2,2-tetrahydro- perfluorooctano! (corresponding to formula (IV), wherein R¢ = perfluorinated n-hexyl, m = 1 and R = H) or Rf -COO-(CH,CH,0)-R, wherein Rt is a linear perfluorinated alkyl having
PY from 16 to 18 carbon atoms, m = 110-130 and R = H.
Some of those compounds are commercially obtainable from a number of sources, e.g. as
ZONYL® Fluorochemical Intermediates (DuPont), e.g. ZONYL® BA-L and BA Fluoro- alcohols, or FLUORAD® Fluorosurfactants (3M), e.g. FLUORAD® FC-431. Further surface- active compounds suitable for use according to the invention can be found in the technical bulletins of the manufacturers mentioned, for example "Technical Information" 233592B (1/94) relating to ZONYL® Fluorochemical Intermediates (DuPont).
One or more compounds of each component (a) to (d) can be used in the compositions according to the invention. ® The compositions according to the invention can be cured in principle by cationic polymer- isation of the epoxy resin system using an initiator system or using any customary epoxy hardener, but it is preferable to use anhydride hardeners.
The invention therefore relates also to a composition comprising the above-mentioned components (a) to (d) and additionally as component (e) a polycarboxylic anhydride.
Such an anhydride may be a linear aliphatic polymeric anhydride, for example polysebacic polyanhydride or polyazelaic polyanhydride, or a cyclic carboxylic anhydride. -
Cyclic carboxylic anhydrides are especially preferred.
Examples of cyclic carboxylic anhydrides are: succinic anhydride, citraconic anhydride, itaconic anhydride, alkenyl-substituted succinic anhydrides, dodecenylisuccinic anhydride, maleic anhydride and tricarbaltylic anhydride, a maleic anhydride adduct with cyclopentadiene or methylcyclopentadiene, a linoleic acid adduct with maleic anhydride, alkylated endoalkylenetetrahydrophthalic anhydrides, methyl- tetrahydrophthalic anhydride and tetrahydrophthalic anhydride, the isomeric mixtures of the two latter compounds being especially suitable. Especially preferred are hexahydrophthalic anhydride and methylhexahydrophthalic anhydride.
Further examples of cyclic carboxylic anhydrides are aromatic anhydrides, for example pyro- mellitic dianhydride, trimellitic anhydride and phthalic anhydride. ® It is also possible to use chlorinated or brominated anhydrides, e.g. tetrachlorophthalic anhydride, tetrabromophthalic anhydride, dichloromaleic anhydride and chlorendic anhydride.
The compositions according to the invention can optionally additionally comprise a curing accelerator (f). Suitable accelerators are known to the person skilled in the art. Examples that may be mentioned are: complexes of amines, especially tertiary amines, with boron trichloride or boron trifluoride; tertiary amines, such as benzyldimethylamine; urea derivatives, such as N-4-chlorophenyl-N',N'-dimethylurea (monuron); unsubstituted or substituted imidazoles, such as imidazole or 2-phenylimidazole. ® Preferred accelerators are tertiary amines, especially benzyldimethylamine, and imidazoles (e.g. 1-methylimidazole) for the above-mentioned compositions that comprise epoxidised oils.
The components (e) and (f) are used in the customary effective amounts, that is to say amounts sufficient for curing the compositions according to the invention. The ratio of components (a) and (e) and optionally (f) depends upon the nature of the compounds used, the rate of curing required and the properties desired in the end product and can readily be determined by the person skilled in the art. Generally, from 0.4 to 1.6 equivalents, preferably - from 0.8 to 1.2 equivalents, of anhydride groups per epoxy equivalent are used.
The resin mixture (a) to (d) and the hardener component (e), optionally together with the accelerator (f), are generally stored separately and mixed together only shortly before -
application. If the resin mixture (a) to (d) is to be kept in interim storage prior to curing, the resin mixture (a) to (d) requires an additional auxiliary as an optional component (g) in order that the mixture, which forms an emulsion, can be maintained in storable form. As such a stabilising auxiliary there may be used emulsifiers (surface-active and interfacially active compounds) and thickeners (for example silicic acids, bentonites, dibenzylidenesorbitol etc.).
Such auxiliaries and their use are well known to the person skilled in the art.
Of the auxiliaries mentioned, the use of highly dispersed silicic acid is preferred. Highly dispersed, hydrophilic, untreated silicic acids are especially suitable. They are commercially ® available, for example in the form of Aerosil®. The effective amounts of silicic acid are in the range of from 0.01 to 3.5 % by weight, preferably from 0.05 to 3.0 % by weight, based on the sum of components (a) to (d), and the average size of the primary particles is advanta- geously about 12 nm.
The invention therefore relates also to storage-stable compositions obtainable by the addition of stabilising auxilaries, such as emulsifiers and thickeners. Instead of hardener component (e), optionally together with an accelerator (f), the resin mixture (a) to (d) may comprise as component (e) an initiator system for the cationic polymerisation of the epoxy resin.
As initiator system for the cationic polymerisation of the epoxy resins there are used, for example, thermally activatable initiators, such as thermally activatable onium salts, oxonium ® salts, iodonium salts, sulfonium salts, phosphonium salts or quaternary ammonium salts that do not contain nucleophilic anions. Such initiators and their use are known. For example,
US Patent 4 336 363, EP-A-0 379 464 and EP-A-0 580 552 disclose specific sulfonium salts as curing agents for epoxy resins. US Patent 4 058 401, in addition to describing specific sulfonium salts, also describes the corresponding salts of tellurium and selenium.
Quaternary ammonium salts as thermally activatable initiators are disclosed, for example, in
EP-A-0O 066 543 and in EP-A-0 673 104. They are salts of aromatic-heterocyclic nitrogen pases with non-nucteophilic, for exampte comptex, halide anions, such as BF, PFg’, SbF, -
SbF5(OH) and AsFg.
As quaternary ammonium salt there is especially used N-benzylquinolinium hexafluoro- antimonate. -
When quaternary ammonium salts are used it is advantageous to use in addition a thermal free-radical former, for example pinacols and their ethers, esters or silyl derivatives. Such compounds are known and can be prepared in accordance with known procedures.
As thermal free-radical formers there are preferably used the pinacols, such as aceto- phenone pinacols or especially 1,1,2,2-tetraphenyl-1,2-ethanediol (benzopinacol).
As thermally activatable initiator there is especially used N-benzylquinolinium hexafluoro- antimonate together with 1,1,2,2-tetraphenyl-1,2-ethanediol, preferably in a molar ratio of ® about 1:1.
The activation temperature of the cationic initiators is generally above room temperature, preferably in the range of from 60 to 180°C, especially from 90 to 150°C.
The amount of cationic initiator contained in the cationically curable epoxy resin is generally from 0.05 to 30 % by weight, preferably from 0.5 to 15 % by weight, based on the amount of cationically polymerisable epoxy resin.
Furthermore, the curable mixtures may comprise tougheners, for example core/shell polymers or the elastomers or elastomer-containing graft polymers known to the person skilled in the art as rubber tougheners. ® Suitable tougheners are described, for example, in EP-A-0 449 776. They are preferably used in an amount of from 1 to 20 % by weight, based on the total amount of epoxy resin in the composition.
The curable mixtures may also comprise further fillers in addition to those mentioned above, for example metal powder, wood flour, glass powder, glass beads, semi-metal and metal oxides, such as SiO, (quartz sand, quartz powder, silanised quartz powder, fused silica powder, silanised fused silica powder), aluminium oxide, titanium oxide and zirconium oxide, metal hydroxides, such as Mg(OH),, Al(OH),, sitanised AOH); and AIO(OH), semi-metal - and metal nitrides, for example silicon nitride, boron nitrides and aluminium nitride, semi- metal and metal carbides (SiC and boron carbides), metal carbonates (dolomite, chalk,
CaCO), metal sulfates (barite, gypsum), ground minerals, e.g. of hydromagnesite and huntite, and natural or synthetic minerals chiefly of the silicate series, e.g. zeolites (especially -
molecular sieves), talcum, mica, kaolin, wollastonite and others. Preferred fillers are quartz powder, silanised quartz powder, aluminium hydroxide and aluminium oxide.
In addition to the additives mentioned above, the curable mixtures may also comprise further customary ingredients, e.g. antioxidants, light stabilisers, flame retardants, fillers containing water of crystallisation, plasticisers, dyes, pigments, fungicides, thixotropic agents, tough- ness improvers, antifoams, antistatics, lubricants, anti-settling agents, wetting agents and mould-release agents.
The compositions according to the invention can be produced in accordance with known ® methods using known mixing apparatus, for example stirrers (especially dispersers and
Supraton® having a high shear gradient), kneaders, rollers or dry mixers. In the case of solid epoxy resins, the dispersing can also be carried out in the melt.
The curing of the mixtures according to the invention can be carried out in known manner in one or more stages. lt is generally effected by heating the mixtures to temperatures of from 60°C to 200°C, especially from 80°C to 180°C.
The invention relates also to the crosslinked products obtainable by curing a composition according to the invention.
Surprisingly, in comparison with the corresponding unmodified systems {Comparison ® Example 1), the addition of the two chemically different siloxane components and the surface-active reagent in the compositions according to the invention results in virtually no impairment, or only slight impairment, of the mechanical and electrical properties of the products obtained therefrom.
The addition of silicones generally results in impairment of the adhesion properties, but the compositions according to the invention nevertheless unexpectedly exhibit good adhesion to metal, which is revealed by the fact that the good cantilever strength and pull-out strength values remain unchanged. Likewise, shaped articles encapsulated using a system according to the invention are surprisingly found to have a comparatively very good temperature - change behaviour.
In comparison with unmodified systems, the invention offers the advantage that traces of the siloxanes used according to the invention are able to migrate onto any soiling present on the -
fully cured material. As a result, an initially hydrophilic layer of dirt also becomes hydrophobic (hydrophobicity transfer), with the result that water more readily rolls away from the soiling in the form of beads and does not form a coherent conductive, and therefore harmful, dirt/water layer, as is the case with the unmodified system. This effect is even, surprisingly, very pronounced. The water runs off in a considerably better and more rapid manner.
Surprisingly, the durability of this effect is also very good, that is to say the pronounced hydrophobicity transfer effect is retained even when the layer of dirt is repeatedly removed and reapplied. ® Even in the case of only slightly soiled epoxy-resin-based insulators, there may be a loss of the original hydrophobicity and thus a rise in the surface conductivity, the reason being microdischarges which can be caused, for example, by individual raindrops on the insulator surface.
In comparison with unmodified systems (Comparison Example 1), a further advantage of the present invention is that, by means of the present systems, the hydrophobicity may surprisingly be regained after such an imposed loss, that is to say the original hydrophobicity is restored within a period ranging from hours to a few days ("recovery" effect).
As a result, the systems according to the invention with their excellent hydrophobicity properties in the form of a very good and at the same time long-lasting hydrophobicity transfer effect in combination with a very good recovery effect and good temperature change o properties are by their nature suitable for use as insulating material for outdoor applications in fields of use where climatic conditions are difficult.
The compositions according to the invention are especially suitable as casting resins, casting compounds ("structural casting"), laminating resins, compression moulding compounds ("epoxy moulding compounds"), coating compounds and especially as electrical insulating compounds.
The invention relates also to the use of the compositions according to the invention as electrical insulating materiat. -
In the following Examples, the following commercially available substances are used: epoxy resin 1: liquid hexahydrophthalic acid diglycidy! ester; epoxy content: 5.6 to 6.2 eq.fkg ("CY 184", Ciba Spezialitaten Chemie)
ESO epoxidised soybean oil, epoxy content: 4.10 to 4.20 eq./kg; ("Reoplast”, Witco)
ELO epoxidised linseed oil, epoxy content: 5.50 to 5.65 eq./kg: ("Merginat", Harburger Chemie) hardener 1 hardener mixture of 70 parts by weight of hexahydrophthalic anhydride and 30 parts by weight of methylhexahydrophthalic anhydride
W 12: untreated quartz powder (Quarzwerke Frechen)
W 12 EST: quartz powder pretreated with epoxysilane (Quarzwerke Frechen) polysiloxane 1: OH-terminated polydimethylsiloxane having a viscosity of 5 Pa - s ® ("NG200-5000", Wacker) polysiloxane 2: mixture of linear OH-terminated (< 40%) polydimethylsiloxanes and cyclic dimethylsiloxanes (> 60%) having a viscosity of 5 to 20 Pa - s ("Dimethyl- methanolysat’, GE-Bayer AG)
Fluorad: non-ionic perfluorinated aliphatic polymeric ester (ethoxylated perfluorinated fatty acid) ("Fluorad FC 431", 3M)
BDMA benzyldimethylamine 1-Mi 1-methylimidazole
Aerosil hydrophilic, highly dispersed silicic acid ("Aerosil 200", Degussa)
Preparation Examples o Comparison Example 1:
In a mixing apparatus having a blade stirring mechanism, 1000 g of epoxy resin 1, 900 g of hardener 1, 5.0 g of BDMA and 2700 g of quartz powder W 12 EST are mixed together within a period of 30 min at 60°C using a mixer having a blade stirring mechanism and then briefly degassed at about 10 mbar. The composition is then cured for 6 hours at 80°C and for hours at 140°C. The properties of the cured product are summarised in Table 1.
Invention Example 1:
In a mixing apparatus having a disperser disc, 9050 g of epoxy resin 1, 200 g of poly- - siloxane 1, 500 g of polysiloxane 2 and 100 g of Fluorad are mixed together at 3750 rev/min at room temperature in the course of 10 minutes. 150 g of Aerosil are then added to the mixture and mixing is carried out at 3750 rev/min at room temperature within a period of one hour, yielding a white, storage-stable emulsion. :
1000 g of the resin premix so prepared are mixed with 814.5 g of hardener 1, 4.5 g of BDMA and 2578.1 g of quartz powder W 12 EST within a period of 30 min at 60°C using a mixer having a blade stirring mechanism and then briefly degassed at about 10 mbar.
The composition is then cured for 6 hours at 80°C and for 10 hours at 140°C. The properties of the cured product are summarised in Table 1.
Invention Example 2:
In a mixing apparatus having a disperser disc, 6855 g of epoxy resin 1, 200 g of poly- siloxane 1, 500 g of polysiloxane 2, 10 g of Fluorad, 1143 of ESO and 1143 g of ELO are ® mixed together at 3750 rev/min at room temperature in the course of 10 minutes. 150 g of
Aerosil are then added to the mixture and mixing is carried out at 3750 rev/min at room temperature within a period of one hour, yielding a white, storage-stable emulsion. 1000 g of the resin premix so prepared are mixed with 806.6 g of hardener 1, 2.3 g of BDMA, 4.5 g of 1-Ml and 2567.1 g of quartz powder W 12 EST within a period of 30 min at 60°C using a mixer having a blade stirring mechanism and then briefly degassed at about mbar.
The composition is then cured for 6 hours at 80°C and for 10 hours at 140°C. The properties of the cured product are summarised in Table 1.
Invention Example 3: ® In a mixing apparatus having a disperser disc, first of all 50 g of dibenzylidenesorbitol are dissolved in 9100 g of epoxy resin 1 at a maximum of 110° and the mixture is then cooled to room temperature. 200 g of polysiloxane 1, 500 g of polysiloxane 2 and 100 g of Fluorad are then added and the mixture is stirred at 1500 rev/min at room temperature for 15 minutes. 50 g of Aerosil are then added to the mixture and at room temperature the entire mixture is stirred at 1500 rev/min for a further one hour, yielding a white, storage-stable emulsion. 1000 g of the resin premix so prepared are mixed with 820 g of hardener 1, 4.5 g of BDMA and 3542 g of quartz powder W 12 EST within a period of 30 min at 60°C using a mixer having a blade stirring mechanism and then briefly degassed at about 10 mbar. -
Application Example 1:
Pin insulators are produced by means of the pressure gelation process. For that purpose, the uncured mixtures, prepared according to Example 1 and analogously to Comparison
Example 1 but with a degree of filler of 66 % by weight, are injected into a metal mould which has been heated to 140°C and treated with parting agent. After gelation (after about 20 min), the casting is removed from the mould and post-cured for 10 hours at 140°C. The insulator produced from the composition according to the invention surprisingly has a cantilever strength of a level similar to that of the insulator produced from the analogous composition without silicone additives, while a comparison of the pull-out strengths shows that the material according to the invention still adheres very well to the insert (see Table 1).
Application Example 2: ® The improved behaviour of the insulators produced using the system modified according to the invention in atmospheres having a high level of air pollution, especially the improved hydrophobicity properties, are demonstrated by the following tests: 2A: Hydrophobicity transfer effect
Specimens of Invention Examples 1 to 3 are tested to demonstrate the so-called "hydro- phobicity transfer effect". For that purpose, artificial soiling is applied to four plates made of material prepared with the product according to Invention Examples 1 to 3 and Comparison
Example 1 (prepared without the use of silicone-containing parting agents and cleaned with acetone after demoulding). For that purpose, quartz powder W 12 is applied to the plates from a vibrating apparatus in an amount per unit area sufficient to produce a foreign layer
C 0.5 mm thick when the powder is smoothed with a ruler or the like. In order to test whether or not the material then transfers the hydrophobicity to the quartz layer, which is actually hydrophilic, at specific time intervals a 30 pl water droplet is applied to the foreign layer using a pipette, the behaviour of the droplet is observed and classified in accordance with the following scheme:
Transfer state system (TS)
Properties Level specimen Specimen inclined | Specimen initially level, at 45° then inclined at 45° 1 No hydro- Droplet is immediately phobicity transfer | absorbed effect (HTE) 1.5 Droplet is absorbed within 2 minutes 2 weak HTE Droplet remains stable for 2 minutes 25 Droplet forms "nose shape" ® 3 moderate HTE Runs off with a large | Droplet remains stable on amount of foreign tilting layer material 3.5 Runs off with a large | Droplet forms "nose amount of foreign | shape" on tilting layer material 4 good HTE Droplet runs off on tilting, leaving a clearly visible track 4.5 Droplet leaves a slight track on tilting excellent HTE | Droplet runs off without foreign material and "dances about" when specimen is tilted slightly
Transfer state system: 500 um thick quartz powder layer (quartz powder W12, Quarzwerke Frechen),
Application 30 pl water droplet
C 2B: Demonstration of the "recovery" effect by means of a plasma test
In order to demonstrate the recovery effect, the state of hydrophobicity is determined (see 2B1). Then a state of hydrophilicity is imposed by the use of a plasma (see 2B2). After the plasma treatment, which is intended to bring about loss of hydrophobicity, the state of the surface is again investigated at various time intervals (immediately, after one hour (h) and one day (d)). A recovery effect is present when a specimen passes from a hydrophilic state (in about class 5 to 7) to a hydrophobic state (in about class 1 to 4), that is to say when the state prior to the plasma treatment has approximately been restored. The results are summarised in Table 1. 2B1: The hydrophobicity state of the specimens at any given time is determined as follows: a vertically arranged specimen surface about 100 cm? in size is sprayed with water 20 times (once per second) from a distance of about 25 + 10 cm using a spray bottle. After a further
10 seconds the specimen is examined and the state of the surface is classified in accord- ance with the following scheme:
Classification of the hydrophobicity state in the spraying test
HC
1 Excellent surface hydrophobicity Only discrete droplets, contact angle for the majority of droplets is > 80°
Very good surface hydrophobicity Only discrete droplets, contact angle for the majority ® of droplets is > 50° but < 80° 3 Good surface hydrophobicity Only discrete droplets, contact angle for the majority of droplets is > 20° but < 50° 4 Moderate surface hydrophobicity Discrete droplets and discrete wetted areas, the size of the individual wetted areas is < 2 cm? and the total wetted area is < 90%
Low surface hydrophobicity Some discrete wetted areas, areas > 2 cm”, the size of the total wetted area is < 90%
Low hydrophilicity > 90% of the total area is wetted but some unwetted sites can be identified
Very hydrophilic surface Continuous film of water over the entire area tested 2B2: A loss of hydrophobicity, i.e. hydrophilicity, is imposed by means of a plasma treatment.
For that purpose, the test plates, which have dimensions of 10 x 10 x 0.4 cm®, are placed in a plasma chamber type 440 (Technics Plasma GmbH) and exposed to the following conditions: plasma treatment time: 2 min, pressure: 2 to 3 mbar, gas: oxygen, output: 9 200 Watt. The treatment results in the loss of hydrophobicity (see Table 1).
Comparative Application Examples:
Three Comparison Examples are prepared in principle analogously to Invention Example 1.
Unlike Invention Example 1, in which polysiloxanes 1 and 2 and a surface-active reagent are used at the same time, in each Comparison Example only one additive is used. The individual compositions and the properties of the cured products are summarised in Table 1.
Table 1
Composition [parts by weight] epoxy resin 1| 100 90.5 | 68.55 91 97 94 99
ESO 11.43
ELO 11.43 polysiloxane 1 2 2 2 2 polysiloxane 2 5 5 5 5
Fluorad 1 0.1 1 1
BDMA| 0.5 0.45 0.23 0.45 0.49 0.47 0.5 1-Ml 0.45
Aerosil 1.56 1.5 0.5 1 1 ® dibenzylidenesorbitol 0.5 hardener 1 90 81.45 | 80.66 82 87.3 84.6 89.1
W12EST| 270 |257.8 [254.6 | 354.2 | 266.1 | 262.3 | 268.7 (resin components + Aerosil) | phase phase — Tgosorcy| io [110 [109 [40 | [ tangent 6 (50 Hz) [%] at 24°C 1 0.5 0.2
Resi Hil NEE temperature at 8% loss [°C] | 125 127 123 tensile strength [MPa] [ 90 86 75 elongation at break [%] | 1.4 1.4 1.3 bending strength [MPa] | 125 137 127 outer fibre strain [%] | 1.3 1.6 1.7 elasticity modulus in flexure [MPa] | 10500 | 9785 | 8813 critical stress intensity factor
K1C [MPa - (m)1/2] | 2.25 2.24 2.12 breaking energy Gc [J/m’]| 485 | 465 | 465 ® transfer state [TS] after 50 h 1 3.5 3.5 4.5 2.5 1 hae HikikE ILI after 500 h in 2nd application 1 4 4 4.5 hydrophobicity class [HC] before plasma 3 2 3 3 2 2 immediately after plasma 7 7 7 6 6 6 1 h after plasma 7 2 6 5 5 7 1 d after plasma 6 1 3 5 5 5 ApplicationExamples(AE)[ AE1 | AE1 | AET [AES filler content [%] | 66 66 66 66
E-- BEDUEEE pull-out strength [N}} 71.6 | 64.8 62 test - DSC (Differential Scanning Calorimetry) carried out using a TA 4000 apparatus (Mettler) - electrical values (tangent 8) according to DIN 53483, measurement frequency 50 Hz - tensile strength and breaking strength according to ISO R527 - bending strength, outer fibre strain and elasticity modulus in flexure according to ISO 178 - K1C and G1C: double torsion test
Table 1 shows: 1) The properties of an unmodified reference material:
No hydrophobicity transfer is found, but good surface hydrophobicity. After the loss thereof (by means of plasma), however, the surface hydrophobicity is not restored. 2) The properties of the modified compositions according to the invention:
Example 1 very quickly exhibits a good hydrophobicity transfer effect, as it does also in the second application of the foreign layer. The material is very hydrophobic in the starting state and very quickly regains hydrophobicity after the imposed loss by means of the plasma and therefore exhibits an excellent recovery effect. ® The second Example exhibits virtually the same hydrophobicity transfer effect as Example 1, but the surface hydrophobicity is not as good. After the loss thereof (by means of plasma), hydrophobicity is restored, but less quickly than in Example 1. The third Example exhibits a very good hydrophobicity transfer effect which is established rapidly. 3) The further Comparison Examples show that the recovery effect cannot be influenced by the individual additives alone. In all cases the hydrophobicity is not regained after imposed loss.
Application Example 3 (comparative cracking test):
Shaped steel articles are encapsulated either with casting resin system 3 according to the invention (see IE3) or with an unmodified casting resin system and the resin is cured. Then ® in a cycle having defined time units, the shaped articles are exposed to specific periods at steadily increasing temperatures and after each period are examined for any crack formation which may have occurred.
Preparation of the unmodified comparison mixture (analogously to Comparison Example 1):
In a mixing apparatus having a blade stirring mechanism, 1000 g of epoxy resin 1, 900 g of hardener 1, 5.0 g of BDMA and 3780 g of quartz powder W 12 EST are mixed together in the course of 30 min at 60°C using a mixer having a blade stirring mechanism and then briefly degassed at about 10 mbar. i
The shaped articles are subjected to the cracking test described below:
Cracking test
In an aluminium casting mould having depressions, batches of 20 steel test specimens of the casting resin systems to be compared are produced by means of the APG (Automatic
Pressure Gelation) process. In that process, the liquid resin mixture is heated to 40-60°C and stirred in vacuo. The resin mixture is then injected into the casting mould (which has been heated to 140-150°C) under a slight pressure of 2-5 bar. While the pressure is maintained, the resin system is gelled in the casting mould within a period of a few minutes, each test specimen produced thus having an enclosed steel body. After gelation, the test specimens are removed from the mould and post-cured for 10 hours at 140°C. The test specimens are ® then exposed to a specific temperature profile. The temperature profile consists of a series of cycles having an upper temperature limit of 25°C, at which each specimen is also examined for any crack formation, whereas the lower temperature limit becomes lower with every cycle. In each cycle, the specimens are rapidly brought to the respective lower or upper temperature limit, and maintained at that particular limit temperature for a few hours.
The cycle in which a specimen exhibits the first cracks is noted. The average cracking temperature of a resin system is determined from the frequency distribution of crack formation per cycle.
The results of the comparative cracking test of Application Example 3 are listed in the following Table: ° / duration [hours] cracked specimens cracked specimens
I EL ER
Ili NC EA li NA I
EEL) I
LT) NL
In the case of the comparison system, the average cracking temperature is calculated to be -12°C, whereas it is -66°C for the system according to the invention. The systems according to the invention, in addition to their hydrophobic behaviour, therefore surprisingly also exhibit an appreciably better temperature change behaviour in comparison with an unmodified system.
Claims (22)
1. A composition comprising (a) an epoxy resin, (b) an OH-terminated polysiloxane, (c) a cyclic polysiloxane and (d) a non-ionic, fluoroaliphatic surface-active reagent.
2. A composition according to claim 1, comprising, ® based on the total composition (a), (b), (c) and (d), from 77.0 to 97.99 % by weight component (a), from 1.0 to 10.0 % by weight component (b), from 1.0 to 10.0 % by weight component (c) and from 0.01 to 3.0 % by weight component (d), the sum of components (a), (b), (c) and (d) being 100 % by weight.
3. A composition according to claim 1, comprising as component (a) a cycloaliphatic epoxy resin or an epoxidation product of a natural unsaturated oil or a derivative thereof.
4. A composition according to claim 1, comprising as component (a) hexahydrophthalic acid ® diglycidy! ester and 3,4-epoxycyclohexylmethyl 3',4'-epoxycyclohexanecarboxylate as well as epoxidised soybean oil or epoxidised linseed oil.
5. A composition according to claim 1, comprising as component (b) a polysiloxane of formula Ri HO $i—0 H 0, R, n ~ wherein Ry and R, are each independently of the other C-C4galkyl, C5s-C4aryl or Cs-Coy- aralkyl and n is an average value of from 3 to 60.
6. A composition according to claim 5, comprising as component (b) a polysiloxane of formula | wherein R; and R; are each independently of the other methyl, ethyl or phenyl.
7. A composition according to claim 5, comprising as component (b) a polysiloxane of formula | wherein Ry and R, are methyl.
8. A composition according to claim 1, comprising as component (c) a cyclic polysiloxane of formula Il . FO (1, R, m wherein Ry and R; are each independently of the other C;-Cqgalkyl, Cs-Cqsaryl or Cg-Coy- aralkyl and m is an integer from 3 to 12.
9. A composition according to claim 8, comprising as component (c) a cyclic polysiloxane of formula I! wherein R, and R, are each independently of the other methyl, ethyl or phenyl and m is an integer from 3 to 8.
10. A composition according to claim 8, comprising as component (c) octamethylcyclotetra- ® siloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane or a hydrolysate of dimethyldichlorosilane.
11. A composition according to claim 11, comprising as component (d) a non-ionic, fluoro- aliphatic surface-active reagent of formula Rf -COO-(CH,CH,0)m-RH (1) or Rf -(CH2CH,0)m-RH (IV), wherein m = 1 to 200, Ry is a linear or branched perfluorinated alkyl having from 2 to 22 carbon atoms and R = H, C-Cgalkyl or Rt.
12. A composition according to claim 11, comprising as component (d) compounds of formula (lil) or (1V) in which the molecular mass according to the theoretical empirical formula is from 300 to 8000.
13. A composition according to claim 12, comprising as component (d) 1,1,2,2-tetrahydro- perfluorooctanol or Rf -COO-(CH,CH,0)-R, wherein Ry is a linear perfluorinated alkyl having from 16 to 18 carbon atoms, m = 110-130 and R = H. ®
14. A composition according to claim 1, additionally comprising as further component (g) emulsifiers or thickeners.
15. A composition according to claim 14, comprising as component (g) from 0.01 to 3.5 % by weight, based on the sum of components (a) to (d), highly dispersed, hydrophilic, untreated silicic acid.
16. A composition according to claim 1 or 14 or 15, additionally comprising a curing agent.
17. A compasition according to claim 16, wherein the curing agent is selected from a polycarboxylic anhydride (e) or from a polycarboxylic anhydride (e) together with an ® accelerator (f).
18. A composition according to claim 16, wherein the curing agent is an initiator system for the cationic polymerisation.
19. A composition according to any one of claims 1 or 14 to 18, which comprises fillers.
20. A composition according to claim 19, which comprises as filler quartz powder, silanised quartz powder, aluminium hydroxide or aluminium oxide.
21. A crosslinked product obtainable by curing a composition according to any one of claims 1 to 20.
22. An electrical insulating material according to claim 21.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CH244198 | 1998-12-09 |
Publications (1)
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ZA200104729B true ZA200104729B (en) | 2002-05-03 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ZA200104729A ZA200104729B (en) | 1998-12-09 | 2001-06-11 | Hydrophobic epoxide resin system. |
Country Status (15)
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EP (1) | EP1141127B1 (en) |
JP (1) | JP4823419B2 (en) |
KR (1) | KR100659220B1 (en) |
CN (1) | CN1121447C (en) |
AT (1) | ATE232224T1 (en) |
AU (1) | AU767776B2 (en) |
BR (1) | BR9916010A (en) |
CA (1) | CA2351333A1 (en) |
CZ (1) | CZ20012031A3 (en) |
DE (1) | DE59904252D1 (en) |
ES (1) | ES2190277T3 (en) |
HK (1) | HK1039627B (en) |
HU (1) | HUP0200220A2 (en) |
WO (1) | WO2000034388A1 (en) |
ZA (1) | ZA200104729B (en) |
Families Citing this family (23)
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DE10051051A1 (en) * | 2000-10-14 | 2002-04-18 | Bosch Gmbh Robert | One-component casting material, e.g. for insulation of electrical components and for production of fuel tanks, contains epoxy resin, a silicone-containing component, filler and initiator |
US6653378B2 (en) * | 2000-12-18 | 2003-11-25 | Dow Corning Corporation | Silicone elastomer compositions |
EP1354916A1 (en) * | 2002-04-17 | 2003-10-22 | Abb Research Ltd. | Self-hardening epoxy resin for the manufacture of electric insulators |
EP1568733A1 (en) * | 2004-02-20 | 2005-08-31 | Abb Research Ltd. | Porous inorganic filler particles having an organopolysiloxane coating for use in curable casting compositions |
DE102004008772A1 (en) | 2004-02-23 | 2005-09-08 | Institut für Neue Materialien Gemeinnützige GmbH | Abrasion resistant and alkali resistant low energy surface coatings or moldings |
JP4572661B2 (en) * | 2004-11-05 | 2010-11-04 | 日立化成工業株式会社 | Resin composition, prepreg, laminate and printed wiring board using the same |
WO2007010025A1 (en) | 2005-07-20 | 2007-01-25 | Areva T & D Sa | Electric insulator and a method for the production thereof |
US7745516B2 (en) * | 2005-10-12 | 2010-06-29 | E. I. Du Pont De Nemours And Company | Composition of polyimide and sterically-hindered hydrophobic epoxy |
JP2008037921A (en) * | 2006-08-02 | 2008-02-21 | Meidensha Corp | Insulating polymeric material composition |
KR100834351B1 (en) * | 2006-11-24 | 2008-06-02 | 제일모직주식회사 | Epoxy Resin Composition for Encapsulating Multichip?Package and the Multichip?Package using the same |
RU2466471C2 (en) * | 2008-02-12 | 2012-11-10 | Абб Рисерч Лтд | Surface modified electric insulation system |
EP2243142A1 (en) * | 2008-02-12 | 2010-10-27 | ABB Research Ltd. | Surface modified electrical insulation system |
JP4893720B2 (en) * | 2008-09-25 | 2012-03-07 | パナソニック電工株式会社 | Thermosetting resin composition and method for producing the same |
CN101445396B (en) * | 2008-12-09 | 2011-08-31 | 西安交通大学 | Method for preparing porcelain insulator surface super-hydrophobic coating |
EP2230267B1 (en) * | 2009-03-20 | 2014-08-13 | ABB Research Ltd. | Method of producing a curable epoxy resin composition |
JP5325742B2 (en) * | 2009-10-29 | 2013-10-23 | 日本ペイント株式会社 | Organic-inorganic composite coating composition made from natural fats and oils |
US20130037310A1 (en) * | 2010-05-07 | 2013-02-14 | Sumitomo Bakelite Co., Ltd. | Epoxy resin composition for circuit board, prepreg, laminate, resin sheet, laminated base material for printed wiring board, printed wiring board, and semiconductor device |
SG187208A1 (en) | 2010-08-31 | 2013-02-28 | Mitsubishi Gas Chemical Co | Resin composition, prepreg, and laminated sheet |
MX349722B (en) | 2011-08-31 | 2017-08-10 | Huntsman Adv Mat Licensing Switzerland Gmbh | Use of hydrophobic epoxide resin system for encapsulation of a instrument transformer. |
MX2017016391A (en) * | 2015-06-16 | 2018-03-02 | Huntsman Adv Mat Licensing Switzerland Gmbh | Epoxy resin composition. |
CN108752749A (en) * | 2018-06-29 | 2018-11-06 | 合肥帧讯低温科技有限公司 | A kind of film and preparation method thereof that tensile strength hydrophobicity is mutually coordinated |
CN110722652B (en) * | 2019-10-25 | 2021-05-28 | 福建省顺昌县升升木业有限公司 | Hydrophobic modification treatment method for cedar |
CN112341756B (en) * | 2020-10-12 | 2022-05-24 | 北京国电富通科技发展有限责任公司 | Organic silicon modified epoxy resin for robot insulating clothes and preparation method thereof |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
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US4609692A (en) * | 1984-11-28 | 1986-09-02 | E. I. Du Pont De Nemours And Company | Low temperature curing maintenance coatings comprising (a) epoxy resin (b) polyamine curing agent (c) polymer containing pendant aminoester groups and (d) organic solvent |
JPS63309515A (en) * | 1987-06-12 | 1988-12-16 | Toshiba Corp | Epoxy resin composition and resin-sealed semiconductor device |
JP2927817B2 (en) * | 1989-05-19 | 1999-07-28 | 日東電工株式会社 | Semiconductor device |
JP3321858B2 (en) * | 1992-11-25 | 2002-09-09 | ジェイエスアール株式会社 | Thermosetting resin composition |
DE19523897C2 (en) * | 1995-06-30 | 2002-10-24 | Bosch Gmbh Robert | Use of silicone-modified epoxy resins as casting compounds for electrotechnical or electronic components |
JP3592825B2 (en) * | 1996-02-07 | 2004-11-24 | 東レ・ダウコーニング・シリコーン株式会社 | Curable epoxy resin composition and electronic component |
US5757541A (en) * | 1997-01-15 | 1998-05-26 | Litton Systems, Inc. | Method and apparatus for an optical fiber amplifier |
EP0899304B1 (en) * | 1997-08-27 | 2005-03-16 | Huntsman Advanced Materials (Switzerland) GmbH | Hydrophobic epoxy resin composition |
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1999
- 1999-11-29 WO PCT/EP1999/009240 patent/WO2000034388A1/en active IP Right Grant
- 1999-11-29 DE DE59904252T patent/DE59904252D1/en not_active Expired - Lifetime
- 1999-11-29 ES ES99959356T patent/ES2190277T3/en not_active Expired - Lifetime
- 1999-11-29 CZ CZ20012031A patent/CZ20012031A3/en unknown
- 1999-11-29 JP JP2000586829A patent/JP4823419B2/en not_active Expired - Fee Related
- 1999-11-29 HU HU0200220A patent/HUP0200220A2/en unknown
- 1999-11-29 EP EP99959356A patent/EP1141127B1/en not_active Expired - Lifetime
- 1999-11-29 CA CA002351333A patent/CA2351333A1/en not_active Abandoned
- 1999-11-29 KR KR1020017006558A patent/KR100659220B1/en active IP Right Grant
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- 1999-11-29 CN CN99814092A patent/CN1121447C/en not_active Expired - Lifetime
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AU767776B2 (en) | 2003-11-27 |
DE59904252D1 (en) | 2003-03-13 |
CN1329642A (en) | 2002-01-02 |
EP1141127A1 (en) | 2001-10-10 |
AU1656000A (en) | 2000-06-26 |
JP4823419B2 (en) | 2011-11-24 |
JP2002531672A (en) | 2002-09-24 |
KR100659220B1 (en) | 2006-12-20 |
HK1039627B (en) | 2003-07-04 |
HK1039627A1 (en) | 2002-05-03 |
BR9916010A (en) | 2001-09-04 |
ATE232224T1 (en) | 2003-02-15 |
CZ20012031A3 (en) | 2001-11-14 |
WO2000034388A1 (en) | 2000-06-15 |
ES2190277T3 (en) | 2003-07-16 |
CA2351333A1 (en) | 2000-06-15 |
CN1121447C (en) | 2003-09-17 |
KR20010101078A (en) | 2001-11-14 |
HUP0200220A2 (en) | 2002-05-29 |
EP1141127B1 (en) | 2003-02-05 |
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