CN113631545A - 作为电灌封料的聚异氰脲酸酯材料 - Google Patents
作为电灌封料的聚异氰脲酸酯材料 Download PDFInfo
- Publication number
- CN113631545A CN113631545A CN202080017036.4A CN202080017036A CN113631545A CN 113631545 A CN113631545 A CN 113631545A CN 202080017036 A CN202080017036 A CN 202080017036A CN 113631545 A CN113631545 A CN 113631545A
- Authority
- CN
- China
- Prior art keywords
- casting resin
- weight
- polyisocyanate
- alkyl
- isocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 238000004382 potting Methods 0.000 title claims abstract description 31
- 150000001875 compounds Chemical class 0.000 title abstract description 39
- 229920000582 polyisocyanurate Polymers 0.000 title abstract description 18
- 239000011495 polyisocyanurate Substances 0.000 title abstract description 17
- 239000000463 material Substances 0.000 title description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 239000005056 polyisocyanate Substances 0.000 claims description 110
- 229920001228 polyisocyanate Polymers 0.000 claims description 110
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 59
- 229920005989 resin Polymers 0.000 claims description 40
- 239000011347 resin Substances 0.000 claims description 40
- 238000005266 casting Methods 0.000 claims description 39
- 239000003054 catalyst Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 27
- 239000012948 isocyanate Substances 0.000 claims description 25
- 238000005829 trimerization reaction Methods 0.000 claims description 23
- 150000002513 isocyanates Chemical class 0.000 claims description 22
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 239000011256 inorganic filler Substances 0.000 claims description 15
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- 238000004132 cross linking Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 239000011159 matrix material Substances 0.000 claims description 5
- 238000003860 storage Methods 0.000 claims description 4
- 239000003990 capacitor Substances 0.000 claims description 3
- 239000012212 insulator Substances 0.000 claims description 3
- 239000004065 semiconductor Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 abstract description 16
- 239000004033 plastic Substances 0.000 abstract description 16
- 239000000945 filler Substances 0.000 description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 51
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 37
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 35
- 125000005442 diisocyanate group Chemical group 0.000 description 27
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 26
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- -1 1-isocyanato-1-methylethyl Chemical group 0.000 description 22
- 239000000203 mixture Substances 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 18
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 16
- 229910052698 phosphorus Inorganic materials 0.000 description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
- 239000011574 phosphorus Substances 0.000 description 15
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 14
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 14
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 13
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical group O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 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 8
- 238000012545 processing Methods 0.000 description 8
- 150000003003 phosphines Chemical class 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 229910052726 zirconium Inorganic materials 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000007788 liquid Substances 0.000 description 4
- 150000004707 phenolate Chemical class 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 229910052684 Cerium Inorganic materials 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000003983 crown ethers Chemical class 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000010433 feldspar Substances 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- HOZMLTCHTRHKRK-UHFFFAOYSA-N 2-methyl-1-silylprop-2-en-1-one Chemical compound CC(=C)C([SiH3])=O HOZMLTCHTRHKRK-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical class [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000010459 dolomite Substances 0.000 description 2
- 229910000514 dolomite Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052735 hafnium Inorganic materials 0.000 description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052622 kaolinite Inorganic materials 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 125000005609 naphthenate group Chemical group 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 125000005474 octanoate group Chemical group 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000004300 potassium benzoate Substances 0.000 description 2
- 235000010235 potassium benzoate Nutrition 0.000 description 2
- 229940103091 potassium benzoate Drugs 0.000 description 2
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
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- VBHJAIGGLJOOLJ-UHFFFAOYSA-M tetramethylphosphanium;fluoride Chemical compound [F-].C[P+](C)(C)C VBHJAIGGLJOOLJ-UHFFFAOYSA-M 0.000 description 1
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
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- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
- C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
- C08G18/168—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1825—Catalysts containing secondary or tertiary amines or salts thereof having hydroxy or primary amino groups
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及固化成聚异氰脲酸酯塑料的灌封料、所述灌封料的生产以及所述灌封料用于制造电气组件的用途。
Description
本发明涉及固化成聚异氰脲酸酯塑料的灌封料、所述灌封料的生产以及所述灌封料用于生产电气组件的用途。
由于它们的良好绝缘性质,塑料常用于包埋电气组件以保护它们例如免于污染、水分或接触。现有技术描述了为此使用环氧树脂、聚氨酯和硅酮。
但是,上文提到的塑料通常由两种组分合成。在此必须精确注意两种组分的混合比以获得最佳品质。
聚氨酯灌封料通常基于聚合亚甲基二(苯基二异氰酸酯)(MDI)和蓖麻油。MDI固有地具有大约200 mPas的低粘度,其使得可并入高填料含量。这由于阻燃原因和由于反应物的高成本是所希望的。
双组分反应混合物通常也具有短适用期。因此需要没有上述缺点的浇铸树脂。
通过异氰酸酯基团与彼此的交联可获得的塑料原则上是现有技术中已知的(WO2015/166983;WO 2016/170059;European Polymer Journal (1980) 16: 147-148)。在WO2017/191175中公开了含有这样的塑料作为基质的复合材料。
US 2015/0344726描述了具有高NCO/OH比和高填料含量的反应混合物。但是,这些混合物也含有多于20重量%的有机溶剂并且因此虽然适用于生产涂料、但不适用于生产模制品。
WO 2014/147072描述了基于双酚A二缩水甘油醚和二苯甲烷二异氰酸酯,即芳族多异氰酸酯的具有高填料含量的反应混合物。该反应混合物的交联不是通过形成异氰脲酸酯基团,而是通过环氧基团与异氰酸酯基团反应成噁唑烷酮来实现的。
在本研究中,已经令人惊讶地发现,聚异氰脲酸酯塑料的电性质,特别是介电常数和损耗系数对于用于电灌封料而言有利。当使用合适的填料时,该反应混合物同时具有足够低的粘度以能够生产电灌封料。
在第一实施方案中,本发明因此提供浇铸树脂,其具有至少3:1的异氰酸酯基团与异氰酸酯反应性基团的摩尔比和最高10重量%的溶剂含量,其中所述浇铸树脂含有
(i) 至少一种具有至少15重量%的异氰酸酯含量的单体或低聚多异氰酸酯A;
(ii) 至少一种含氧化硅单元的无机填料B,其具有根据DIN EN ISO 787-5(1995年10月)测定的最高25 g/100 g的油值和至少4的莫氏硬度;和
(iii) 至少一种三聚催化剂C。
“浇铸树脂”是含有上文定义的成分并固化以形成聚异氰脲酸酯复合材料的反应性树脂。在此,由多异氰酸酯A获得的聚异氰脲酸酯塑料形成聚合物基质,在其中包埋有无机填料B。术语“浇铸树脂”因此表征其中上文定义的组分以反应性和混合形式存在以使多异氰酸酯A可通过三聚催化剂C交联的反应混合物。根据本发明的浇铸树脂有利地用于包埋电气组件,即用作电灌封料。电气组件完全或部分包埋在根据本发明的浇铸树脂中用于实现对环境影响的防护、对接触的防护、电绝缘或机械稳定化。
通过浇铸树脂的固化,获得聚异氰脲酸酯材料。这是由作为基质材料的聚异氰脲酸酯塑料和无机填料B构成的复合材料。其进一步含有三聚催化剂C的残留物和任选添加剂如紫外线稳定剂、助流剂或颜料。
电气组件优选选自变压器、绝缘体、电容器、半导体、用于保护电缆接头和地下电缆分支的套筒。
聚异氰脲酸酯塑料
术语“聚异氰脲酸酯塑料”描述了通过异氰酸酯基团与彼此的交联获得的塑料。这在浇铸树脂含有适用于这种交联的催化剂C并同时具有异氰酸酯基团与异氰酸酯反应性基团的高摩尔比时实现。由此使得非常主要仅其它异氰酸酯基团作为反应搭档用于异氰酸酯基团。术语“异氰酸酯反应性基团”在本申请中被理解为是指环氧基、羟基、氨基和硫醇基团。
该浇铸树脂中的异氰酸酯基团与异氰酸酯反应性基团的摩尔比优选至少3: 1,优选至少5: 1,再更优选至少10: 1,最优选至少20: 1。
在模制品的生产中,反应混合物中的高溶剂含量是不利的,因为溶剂蒸发并在模制品中留下空洞或裂纹。根据本发明的浇铸树脂因此含有最高10重量%,优选最高5重量%,更优选最高2重量%的溶剂。术语“溶剂”被理解为是指所有在室温下为液体的有机溶剂和水。具有至少一个如上文定义的异氰酸酯反应性基团或至少一个异氰酸酯基团的化学化合物在本专利申请中不是溶剂,因为它们可经由所涉官能团与多异氰酸酯A交联。
在反应混合物的反应以提供聚异氰脲酸酯塑料中,多异氰酸酯A中存在的游离异氰酸酯基团的至少50摩尔%,优选至少60摩尔%,特别优选至少70摩尔%,特别是至少80摩尔%,非常特别优选90摩尔%转化成异氰脲酸酯结构单元。最终的聚异氰脲酸酯塑料因此将相应比例的最初包含于多异氰酸酯A中的氮结合在异氰脲酸酯结构内。但是,通常发生副反应,尤其是产生脲二酮、脲基甲酸酯和/或亚氨基噁二嗪二酮结构的那些,并且甚至可以受控方式使用以有利地影响例如所得聚异氰脲酸酯塑料的玻璃化转变温度(Tg)。
由于根据本发明反应混合物中的异氰酸酯基团相对于异氰酸酯反应性基团而言明显摩尔过量,反应混合物中包含的反应性异氰酸酯基团的最高50摩尔%,优选最高30摩尔%,特别优选最高10摩尔%,非常特别优选最高5摩尔%,特别是最高3摩尔%将在聚异氰脲酸酯塑料中作为氨基甲酸酯和/或脲基甲酸酯基团存在。
由于无机填料如聚氨酯化学中常规那样仅允许具有低水分含量,其相对于异氰酸酯基团而言呈惰性并可在上文提到的计算中不加以考虑。
多异氰酸酯A
本文所用的术语“多异氰酸酯”是在分子中含有两个或更多个异氰酸酯基团(这被本领域技术人员理解为是指通用结构–N=C=O的游离异氰酸酯基团)的化合物的集合术语。这些多异氰酸酯的最简单和最重要的代表是二异氰酸酯。这些具有通用结构O=C=N–R–N=C=O,其中R通常代表脂族、脂环族和/或芳族基团。在本申请中,术语“多异氰酸酯A”是指反应混合物中包含的具有每分子平均至少两个异氰酸酯基团的所有化合物的整体。多异氰酸酯A因此可由单一的多异氰酸酯组成。但是,其也可以是多种不同多异氰酸酯的混合物。在下文定义的实施方案中,多异氰酸酯A也可含有具有小于2的平均官能度的异氰酸酯的混入物。
由于多官能度(每分子≥ 2个异氰酸酯基团),可由多异氰酸酯制造多种聚合物(例如聚氨酯、聚脲和聚异氰脲酸酯)和低分子量化合物(例如具有脲二酮、异氰脲酸酯、脲基甲酸酯、缩二脲、亚氨基噁二嗪二酮和/或噁二嗪三酮结构的那些)。
在本申请中,术语“多异氰酸酯”同样地是指单体和/或低聚多异氰酸酯。但是,为了理解本发明的许多方面,重要的是区分单体二异氰酸酯和低聚多异氰酸酯。当在本申请中提到“低聚多异氰酸酯”时,则这是指由至少两个单体二异氰酸酯分子形成的多异氰酸酯,即构成或含有由至少两个单体二异氰酸酯分子形成的反应产物的化合物。
由单体二异氰酸酯制造低聚多异氰酸酯在本文中也被称为单体二异氰酸酯的改性。本文所用的这种“改性”在此是指单体二异氰酸酯的反应以产生具有脲二酮、异氰脲酸酯、脲基甲酸酯、缩二脲、亚氨基噁二嗪二酮和/或噁二嗪三酮结构的低聚多异氰酸酯。
因此,例如1,6-己二异氰酸酯(HDI)是“单体二异氰酸酯”,因为其含有两个异氰酸酯基团并且不是至少两个多异氰酸酯分子的反应产物:
相反,始终仍具有至少两个异氰酸酯基团的至少两个HDI分子的反应产物在本发明的情况下是“低聚多异氰酸酯”。从单体HDI出发,这样的“低聚多异氰酸酯”的代表是例如HDI异氰脲酸酯和HDI缩二脲,它们各自由三个单体HDI分子构成:
根据本发明,基于多异氰酸酯A的总量计,异氰酸酯基团的重量比例为至少15重量%。
原则上,单体和低聚多异氰酸酯同等适用于根据本发明的反应混合物。多异氰酸酯A因此可基本由单体多异氰酸酯组成或基本由低聚多异氰酸酯组成。但是,其也可包含任意混合比的低聚和单体多异氰酸酯。
在本发明的一个优选实施方案中,用作反应物的多异氰酸酯A是贫单体的(即贫单体二异氰酸酯)并已含有低聚多异氰酸酯。术语“贫单体”和“贫单体二异氰酸酯”在本文中相对于多异氰酸酯A同义使用。
当多异氰酸酯A具有在每种情况下基于多异氰酸酯A的重量计最高20重量%,尤其最高15重量%或最高10重量%的单体二异氰酸酯比例时,获得特别有用的结果。优选的是,多异氰酸酯A具有最高5重量%,优选最高2.0重量%,更优选最高1.0重量%的单体二异氰酸酯含量,在每种情况下基于多异氰酸酯A的重量计。当多异氰酸酯A基本不含单体二异氰酸酯时,建立特别好的结果。“基本不含”在此是指单体二异氰酸酯的含量为基于多异氰酸酯A的重量计最高0.5重量%。
在本发明的一个特别优选的实施方案中,多异氰酸酯A完全或在每种情况下基于多异氰酸酯A的重量计至少80、85、90、95、98、99或99.5重量%的程度上由低聚多异氰酸酯组成。在此优选的是至少99重量%的低聚多异氰酸酯含量。低聚多异氰酸酯的这种含量涉及如供应时的多异氰酸酯A。即,该低聚多异氰酸酯不是在根据本发明的方法的过程中作为中间体形成的,而是在反应开始时已存在于用作反应物的多异氰酸酯A中。
贫单体或基本不含单体异氰酸酯的多异氰酸酯组合物可通过在每种情况下在实际改性反应后进行至少一个用于分离出未转化的过量单体二异氰酸酯的进一步方法步骤来获得。可通过本身已知的方法,优选通过在高真空下的薄膜蒸馏或通过用对异氰酸酯基团呈惰性的合适溶剂,例如脂族或脂环族烃,如戊烷、己烷、庚烷、环戊烷或环己烷萃取而以特别实用的方式实现这种单体分离。
在本发明的一个优选实施方案中,通过将单体二异氰酸酯改性和随后分离出未转化的单体而获得多异氰酸酯A。
但是,在本发明的一个特定实施方案中,贫单体的多异氰酸酯A含有单体外来二异氰酸酯。在本文中,“单体外来二异氰酸酯”是指其不同于已用于制造多异氰酸酯A中包含的低聚多异氰酸酯的单体二异氰酸酯。
单体外来二异氰酸酯的加入可能有利于实现特定技术效果,例如特定硬度。当异氰酸酯A具有在每种情况下基于多异氰酸酯A的重量计最高20重量%,尤其最高15重量%或最高10重量%的单体外来二异氰酸酯的比例时,获得特别有实用意义的结果。优选的是,异氰酸酯A具有在每种情况下基于多异氰酸酯A的重量计最高5重量%,优选最高2.0重量%,更优选最高1.0重量%的单体外来二异氰酸酯含量。
在本发明的方法的另一特定实施方案中,多异氰酸酯A含有单体单异氰酸酯或具有大于2的异氰酸酯官能度,即具有每分子多于两个异氰酸酯基团的单体异氰酸酯。已经发现单体单异氰酸酯或具有大于2的异氰酸酯官能度的单体异氰酸酯的加入是有利的,以影响该涂层的网络密度。当异氰酸酯A具有在每种情况下基于多异氰酸酯A的重量计最高20重量%,尤其最高15重量%或最高10重量%的在多异氰酸酯A中的单体单异氰酸酯或具有大于2的异氰酸酯官能度的单体异氰酸酯的比例时,建立特别有实用意义的结果。优选的是,多异氰酸酯A具有在每种情况下基于异氰酸酯A的重量计最高5重量%,优选最高2.0重量%,更优选最高1.0重量%的单体单异氰酸酯或具有大于2的异氰酸酯官能度的单体异氰酸酯的含量。优选的是,在根据本发明的三聚反应中不随之使用单体单异氰酸酯或具有大于2的异氰酸酯官能度的单体异氰酸酯。
根据本发明,低聚多异氰酸酯特别可包含脲二酮、异氰脲酸酯、脲基甲酸酯、缩二脲、亚氨基噁二嗪二酮和/或噁二嗪三酮结构。在本发明的一个实施方案中,低聚多异氰酸酯具有下列低聚结构类型的至少一种或其混合物:
在本发明的一个优选实施方案中,使用多异氰酸酯A,其异氰脲酸酯结构比例为基于多异氰酸酯A中存在的选自脲二酮、异氰脲酸酯、脲基甲酸酯、缩二脲、亚氨基噁二嗪二酮和噁二嗪三酮结构的低聚结构的总和计至少50摩尔%,优选至少60摩尔%,更优选至少70摩尔%,再更优选至少80摩尔%,再更优选至少90摩尔%,尤其优选至少95摩尔%。
在本发明的另一个优选的实施方案中,根据本发明的方法中使用不仅含有异氰脲酸酯结构还含有至少一种具有脲二酮、缩二脲、脲基甲酸酯、亚氨基噁二嗪二酮和噁二嗪三酮结构及其混合物的其它低聚多异氰酸酯的多异氰酸酯A。
可以例如通过NMR谱法测定多异氰酸酯A中的脲二酮、异氰脲酸酯、脲基甲酸酯、缩二脲、亚氨基噁二嗪二酮和/或噁二嗪三酮结构的比例。在此优选可使用13C NMR谱法(其优选为质子解耦形式),因为所提到的低聚结构产生特征信号。
无论基础低聚结构如何(脲二酮、异氰脲酸酯、脲基甲酸酯、缩二脲、亚氨基噁二嗪二酮和/或噁二嗪三酮结构),用于根据本发明的方法的低聚多异氰酸酯A优选具有2.0至5.0,优选2.3至4.5的(平均)NCO官能度。
当根据本发明使用的多异氰酸酯A具有在每种情况下基于多异氰酸酯A的重量计8.0重量%至28.0重量%,优选14.0重量%至25.0重量%的异氰酸酯基团含量时,建立特别有实用意义的结果。
根据本发明用于多异氰酸酯A的具有脲二酮、异氰脲酸酯、脲基甲酸酯、缩二脲、亚氨基噁二嗪二酮和/或噁二嗪三酮结构的低聚多异氰酸酯的生产方法例如描述在J.Prakt. Chem. 336 (1994) 185 - 200、DE-A 1 670 666、DE-A 1 954 093、DE-A 2 414413、DE-A 2 452 532、DE-A 2 641 380、DE-A 3 700 209、DE-A 3 900 053和DE-A 3 928503或EP-A 0 336 205、EP-A 0 339 396和EP-A 0 798 299中。
在本发明的附加或替代性的实施方案中,多异氰酸酯A被定义为含有已在遵循5%至45%,优选10%至40%,特别优选15%至30%的低聚度的情况下获自单体二异氰酸酯(无论所用改性反应的性质如何)的低聚多异氰酸酯。“低聚度”在此被理解为是指在生产过程中为形成氨基甲酸酯、脲二酮、异氰脲酸酯、脲基甲酸酯、缩二脲、亚氨基噁二嗪二酮和/或噁二嗪三酮结构而消耗的最初存在于起始混合物中的异氰酸酯基团的百分比。
用于生产用于本发明的方法的多异氰酸酯A和其中包含的单体和/或低聚多异氰酸酯的合适多异氰酸酯是可以各种方式,例如通过在液相或气相中光气化或通过无光气途径,例如通过热氨基甲酸酯裂解而获得的任意多异氰酸酯。当该多异氰酸酯是单体二异氰酸酯时,建立特别好的结果。优选的单体二异氰酸酯是具有140至400 g/mol的分子量、具有脂族、脂环族、芳脂族和/或芳族键合的异氰酸酯基团的那些,例如1,4-丁烷二异氰酸酯(BDI)、1,5-戊烷二异氰酸酯(PDI)、1,6-己烷二异氰酸酯(HDI)、2-甲基-1,5-戊烷二异氰酸酯、1,5-二异氰酸根合-2,2-二甲基戊烷、2,2,4-或2,4,4-三甲基-1,6-己烷二异氰酸酯、1,10-癸烷二异氰酸酯、1,3-和1,4-环己烷二异氰酸酯、1,4-二异氰酸根合-3,3,5-三甲基环己烷、1,3-二异氰酸根合-2-甲基环己烷、1,3-二异氰酸根合-4-甲基环己烷、1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷(异佛尔酮二异氰酸酯;IPDI)、1-异氰酸根合-1-甲基-4(3)-异氰酸根合甲基环己烷、2,4'-和4,4'-二环己基甲烷二异氰酸酯(H12MDI)、1,3-和1,4-双(异氰酸根合甲基)环己烷、双(异氰酸根合甲基)降冰片烷(NBDI)、4,4'-二异氰酸根合-3,3'-二甲基二环己基甲烷、4,4'-二异氰酸根合-3,3',5,5'-四甲基二环己基甲烷、4,4'-二异氰酸根合-1,1'-二(环己基)、4,4'-二异氰酸根合-3,3'-二甲基-1,1'-二(环己基)、4,4'-二异氰酸根合-2,2',5,5'-四甲基-1,1'-二(环己基)、1,8-二异氰酸根合-对薄荷烷、1,3-金刚烷二异氰酸酯、1,3-二甲基-5,7-金刚烷二异氰酸酯、1,3-和1,4-双(异氰酸根合甲基)苯(苯二甲基二异氰酸酯;XDI)、1,3-和1,4-双(1-异氰酸根合-1-甲基乙基)苯(TMXDI)和双(4-(1-异氰酸根合-1-甲基乙基)苯基)碳酸酯、2,4-和2,6-甲苯二异氰酸酯(TDI)、2,4'-和4,4'-二苯甲烷二异氰酸酯(MDI)、1,5-萘二异氰酸酯和这些二异氰酸酯的任意混合物。同样合适的其它二异氰酸酯另外可见于例如Justus Liebigs Annalen derChemie, 第562卷(1949)第75-136页。
可任选用于异氰酸酯组分A的合适的单体单异氰酸酯是例如异氰酸正丁酯、异氰酸正戊酯、异氰酸正己酯、异氰酸正庚酯、异氰酸正辛酯、异氰酸十一烷基酯、异氰酸十二烷基酯、异氰酸十四烷基酯、异氰酸鲸蜡酯、异氰酸十八酯、异氰酸环戊酯、异氰酸环己酯、异氰酸3-或4-甲基环己酯或这些单异氰酸酯的任意混合物。可任选添加到多异氰酸酯组分A中的具有大于2的异氰酸酯官能度的单体异氰酸酯的一个实例是4-异氰酸根合甲基辛烷1,8-二异氰酸酯(壬烷三异氰酸酯;TIN)。
在本发明的一个实施方案中,多异氰酸酯A含有在每种情况下基于多异氰酸酯A的重量计最高30重量%,尤其最高20重量%、最高15重量%、最高10重量%、最高5重量%或最高1重量%的芳族多异氰酸酯。本文所用的“芳族多异氰酸酯”是指具有至少一个芳族键合的异氰酸酯基团的多异氰酸酯。
芳族键合的异氰酸酯基团被理解为是指键合到芳族烃基上的异氰酸酯基团。
在本发明的方法的一个优选实施方案中,使用仅具有脂族和/或脂环族键合的异氰酸酯基团的多异氰酸酯A。
脂族和脂环族键合的异氰酸酯基团分别被理解为是指键合到脂族和脂环族烃基上的异氰酸酯基团。在本发明的方法的另一优选实施方案中,使用由一种或多种低聚多异氰酸酯组成或包含一种或多种低聚多异氰酸酯的多异氰酸酯A,其中所述一种或多种低聚多异氰酸酯仅具有脂族和/或脂环族键合的异氰酸酯基团。
在本发明的另一个实施方案中,多异氰酸酯A在每种情况下基于多异氰酸酯A的重量计至少70、80、85、90、95、98或99重量%的程度上由仅具有脂族和/或脂环族键合的异氰酸酯基团的多异氰酸酯组成。实际实验已经表明,用其中包含的低聚多异氰酸酯仅具有脂族和/或脂环族键合的异氰酸酯基团的多异氰酸酯A可实现特别好的结果。
在本发明的方法的一个特别优选的实施方案中,使用由一种或多种低聚多异氰酸酯组成或含有一种或多种低聚多异氰酸酯的多异氰酸酯A,其中所述一种或多种低聚多异氰酸酯基于1,4-丁烷二异氰酸酯(BDI)、1,5-戊烷二异氰酸酯(PDI)、1,6-己烷二异氰酸酯(HDI)、异佛尔酮二异氰酸酯(IPDI)或4,4'-二环己基甲烷二异氰酸酯(H12MDI)或其混合物构成。
无机填料B
为了实现最终组件的良好机械性质,无机填料B具有至少4.0,优选至少5.0,更优选至少5.5的莫氏硬度。根据本发明的是含有氧化硅单元的填料。这些尤其是硅酸盐和石英。特别优选的是,填料B是石英或长石。
高填料含量原则上是所希望的,以保持低材料成本和实现良好的阻燃性。但是,高填料含量的缺点在于它们提高浇铸树脂的粘度。当使用聚合MDI(pMDI)作为聚氨酯的合成组分时,这问题较少,因为pMDI具有大约90-200 mPas的粘度。当pMDI应被脂族异氰酸酯替代时,浇铸树脂的粘度更快达到加工临界限,因为低聚脂族异氰酸酯通常具有1500 mPas或更大的粘度。因此在此必须选择特殊填料,其在高填料含量下也与脂族异氰酸酯组合导致浇铸树脂的低粘度。
此处的临界参数是油值。实施例显示当无机填料B的油值为最高25 g/100 g时,在反应混合物在60℃下储存1小时后不超过110 Pas的粘度。对比例V6和V7显示,使用在其它方面根据本发明但其油值略高于根据本发明的值的填料就已实现高粘度或使得已不再可能制造液体反应混合物。此外,V4与E10的直接比较显示,不含氧化硅单元的填料甚至在极低油值下(V4中的15 g/100 g与E10中的21 g/100 g相比)也在60℃下储存1小时后具有高40%的粘度。
无机填料B因此具有根据DIN EN ISO 787-5(1995年10月)测定的最高25 g/100g,优选最高22 g/100 g,更优选最高20 g/100 g的油值。
填料可带有常规涂层,例如脂肪酸、硅烷或钛酸酯。
优选的是,浇铸树脂在30重量%至90重量%的程度上,优选在40重量%至80重量%的程度上,更优选在50重量%至80重量%的程度上,特别优选在50重量%至65重量%的程度上由无机填料B组成。
已经证实特别有利的是,对于高度填充材料,特别是具有最多65重量%的填料含量的材料,浇铸树脂始终仍具有对加工而言足够低的粘度。根据本发明的浇铸树脂因此特征优选在于。当使用最多65重量%的具有根据DIN EN ISO 787-5(1995年10月)测定的最多25g/100 g的油值的根据本发明的无机填料时,所述浇铸树脂具有在60℃下最高200 Pas,优选最高150 Pas的粘度并且甚至在此温度下储存至少1小时后也没有超过这一适用期。使用来自AntonPaar公司的MCR301Rheometer测定粘度。在频率f = 1 Hz和振幅γ = 5%下使用具有珀尔帖加热C-PTD200的板/板系统PP25。
为了遵循上一段中提到的参数,有利的是在25℃下多异氰酸酯A具有最高20000mPas,优选最高10000 mPas,更优选最高5000 mPas的粘度。在此粘度优选为至少500 mPas。
三聚催化剂C
三聚催化剂C可由一种或不同的催化剂类型混合,但含有至少一种引起异氰酸酯基团三聚成异氰脲酸酯或亚氨基噁二嗪二酮的催化剂。
用于根据本发明的方法的合适的催化剂是例如简单叔胺,例如三乙胺、三丁胺、N,N-二甲基苯胺、N-乙基哌啶或N,N'-二甲基哌嗪。合适的催化剂还是GB 2 221 465中描述的叔羟基烷基胺,例如三乙醇胺、N-甲基二乙醇胺、二甲基乙醇胺、N-异丙基二乙醇胺和1-(2-羟乙基)吡咯烷,或从GB 2 222 161中获知的由叔双环胺,例如DBU与简单低分子量脂族醇的混合物组成的催化剂体系。
许多不同的金属化合物同样适合作为用于本发明的方法的三聚催化剂。合适的实例是在DE-A 3 240 613中作为催化剂描述的锰、铁、钴、镍、铜、锌、锆、铈或铅的辛酸盐和环烷酸盐或其与锂、钠、钾、钙或钡的乙酸盐的混合物,从DE-A 3 219 608获知的具有最多10个碳原子的直链或支化烷羧酸,如丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸和十一烷酸的钠和钾盐,从EP-A 0 100 129获知的具有2至20个碳原子的脂族、脂环族或芳族单羧酸和多羧酸的碱金属或碱土金属盐,如苯甲酸钠或苯甲酸钾,从GB-PS 1 391 066和GB-PS 1386 399获知的碱金属酚盐,如苯酚钠或苯酚钾,从GB 809 809获知的碱金属和碱土金属氧化物、氢氧化物、碳酸盐、醇盐和酚盐,可烯醇化的化合物的碱金属盐以及弱脂族或脂环族羧酸的金属盐,如甲醇钠、乙酸钠、乙酸钾、乙酰乙酸钠、2-乙基己酸铅和环烷酸铅,从EP-A0 056 158和EP-A 0 056 159获知的与冠醚或聚醚醇络合的碱性碱金属化合物,如络合的羧酸钠或羧酸钾,从EP-A 0 033 581获知的吡咯烷酮钾盐,从申请EP 13196508.9获知的钛、锆和/或铪的单核或多核络合物,如四正丁氧基锆、四-2-乙基己酸锆和四-2-乙基己醇锆,和European Polymer Journal, 第16卷, 147-148 (1979)中描述的类型的锡化合物,如二氯化二丁基锡、二氯化二苯基锡、三苯基锡烷醇、乙酸三丁基锡、氧化三丁基锡、二辛酸锡、二丁基(二甲氧基)锡烷和三丁基锡咪唑盐。
适用于本发明的方法的其它三聚催化剂是例如从DE-A 1 667 309、EP-A 0 013880和EP-A 0 047 452中获知的季铵氢氧化物,例如四乙基氢氧化铵、三甲基苄基氢氧化铵、N,N-二甲基-N-十二烷基-N-(2-羟乙基)氢氧化铵、N-(2-羟乙基)-N,N-二甲基-N-(2,2'-二羟甲基丁基)氢氧化铵和1-(2-羟乙基)-1,4-二氮杂双环[2.2.2]辛烷氢氧化物(环氧乙烷和水加成到1,4-二氮杂双环[2.2.2]辛烷上的单加成物),从EP-A 37 65或EP-A 10589中获知的季羟基烷基铵氢氧化物,例如N,N,N-三甲基-N-(2-羟乙基)氢氧化铵,从DE-A2631733、EP-A 0 671 426、EP-A 1 599 526和US 4,789,705中获知的三烷基羟烷基铵羧酸盐,例如对叔丁基苯甲酸N,N,N-三甲基-N-2-羟丙基铵和2-乙基己酸N,N,N-三甲基-N-2-羟丙基铵,从EP-A 1 229 016中获知的季苄基铵羧酸盐,例如特戊酸N-苄基-N,N-二甲基-N-乙基铵、2-乙基己酸N-苄基-N,N-二甲基-N-乙基铵、2-乙基己酸N-苄基-N,N,N-三丁基铵、2-乙基己酸N,N-二甲基-N-乙基-N-(4-甲氧基苄基)铵或特戊酸N,N,N-三丁基-N-(4-甲氧基苄基)铵,从WO 2005/087828中获知的四取代铵α-羟基羧酸盐,例如四甲基乳酸铵,从EP-A 0 339 396、EP-A 0 379 914和EP-A 0 443 167中获知的季铵或鏻氟化物,例如具有C8-C10-烷基的N-甲基-N,N,N-三烷基铵氟化物、氟化N,N,N,N-四-正丁基铵、氟化N,N,N-三甲基-N-苄基铵、氟化四甲基鏻、氟化四乙基鏻或氟化四正丁基鏻,从EP-A 0 798 299、EP-A 0896 009和EP-A 0 962 455中获知的季铵和鏻多氟化物,例如多氟化氢苄基三甲基铵,从EP-A 0 668 271中获知并可通过叔胺与碳酸二烷基酯的反应获得的烷基碳酸四烷基铵,或甜菜碱结构化的季氨基烷基碳酸盐,从WO 1999/023128中获知的季铵碳酸氢盐,例如胆碱碳酸氢盐,从EP 0 102 482中获知并可由叔胺与含磷酸的起烷基化作用的酯获得的季铵盐,例如三乙胺、DABCO或N-甲基吗啉与甲基膦酸二甲酯的反应产物,或从WO 2013/167404中获知的内酰胺的四取代铵盐,例如三辛基铵己内酰胺盐或十二烷基三甲基铵己内酰胺盐。
根据本发明合适的其它三聚催化剂C可见于例如J. H. Saunders和K. C.Frisch, Polyurethanes Chemistry and Technology, 第94页及其后(1962)和其中引用的文献。
特别优选的是以金属或铵离子作为抗衡离子的羧酸盐和酚盐。合适的羧酸根是所有脂族或脂环族羧酸的阴离子,优选是具有1至20个碳原子的单羧酸或多羧酸的那些。合适的金属离子衍生自碱金属或碱土金属、锰、铁、钴、镍、铜、锌、锆、铈、锡、钛、铪或铅。优选的碱金属是锂、钠和钾,特别优选钠和钾。优选的碱土金属是镁、钙、锶和钡。
非常特别优选的是DE-A 3 240 613中作为催化剂描述的锰、铁、钴、镍、铜、锌、锆、铈或铅的辛酸盐和环烷酸盐或其与锂、钠、钾、钙或钡的乙酸盐的混合物。
非常特别优选的同样是苯甲酸钠或苯甲酸钾,从GB-PS 1 391 066和GB-PS 1 386399中获知的碱金属酚盐,例如苯酚钠或苯酚钾,以及从GB 809 809中获知的碱金属和碱土金属氧化物、氢氧化物、碳酸盐、醇盐和酚盐。
三聚催化剂C优选含有聚醚。当该催化剂含有金属离子时,这尤其优选。优选的聚醚选自冠醚、二乙二醇、聚乙二醇和聚丙二醇。已经发现在本发明的方法中特别有实用意义的是使用含有聚乙二醇或冠醚,更优选18-冠醚-6或15-冠醚-5作为聚醚的三聚催化剂C。三聚催化剂C优选含有具有100至1000 g/mol,优选300 g/mol至500 g/mol,特别是350 g/mol至450 g/mol的数均分子量的聚乙二醇。
非常特别优选的是碱金属或碱土金属的上述羧酸盐和酚盐与聚醚的组合。
还已经发现,根据下式(I)的化合物特别好地适合作为催化剂C
其中R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基;
A选自O、S和NR3,其中R3选自氢、甲基、乙基、丙基、异丙基、丁基和异丁基;和
B,独立于A,选自OH、SH NHR4和NH2,其中R4选自甲基、乙基和丙基。
在一个优选实施方案中,A是NR3,其中R3选自氢、甲基、乙基、丙基、异丙基、丁基和异丁基。R3优选是甲基或乙基。R3更优选是甲基。
在这个实施方案的第一变体中,B是OH且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。
在这个实施方案的第二变体中,B是SH且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。
在这个实施方案的第三变体中,B是NHR4且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。在这一变体中,R4选自甲基、乙基和丙基。R4优选是甲基或乙基。R4更优选是甲基。
在这个实施方案的第四变体中,B是NH2且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。
在另一个优选的实施方案中,A是氧。
在这个实施方案的第一变体中,B是OH且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。
在这个实施方案的第二变体中,B是SH且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。
在这个实施方案的第三变体中,B是NHR4且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。在这一变体中,R4选自甲基、乙基和丙基。R4优选是甲基或乙基。R4更优选是甲基。
在这个实施方案的第四变体中,B是NH2且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。
在再另一个优选的实施方案中,A是硫。
在这个实施方案的第一变体中,B是OH且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。
在这个实施方案的第二变体中,B是SH且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。
在这个实施方案的第三变体中,B是NHR4且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。在这一变体中,R4选自甲基、乙基和丙基。R4优选是甲基或乙基。R4更优选是甲基。
在这个实施方案的第四变体中,B是NH2且R1和R2彼此独立地选自氢、甲基、乙基、丙基、异丙基、丁基、异丁基、支化C5-烷基、非支化C5-烷基、支化C6-烷基、非支化C6-烷基、支化C7-烷基和非支化C7-烷基。R1和R2优选彼此独立地为甲基或乙基。R1和R2更优选是甲基。
式(I)的化合物和具有至少一个异氰酸酯基团的化合物的加合物也合适。
涵盖性术语“加合物”被理解为是指式(I)的化合物与具有至少一个异氰酸酯基团的化合物的氨基甲酸酯加合物、硫代氨基甲酸酯加合物和脲加合物。氨基甲酸酯加合物特别优选。当异氰酸酯与式(I)中定义的化合物的官能团B反应时,形成根据本发明的加合物。当B是羟基时,形成氨基甲酸酯加合物。当B是硫醇基团时,形成硫代氨基甲酸酯加合物。当B是NH2或NHR4时,形成脲加合物。
根据本发明合适的另外的催化剂是通式(II)的膦或这样的膦的混合物
其中
R1、R2和R3是相同或不同基团并各自是具有最多10个碳原子的烷基或环烷基,优选具有2至8个碳原子的烷基或具有3至8个碳原子的环烷基、具有7至10,优选7个碳原子的芳烷基或任选被具有最多10个,优选1至6个碳原子的烷基取代的具有6至10,优选6个碳原子的芳基,条件是基团中的最多一个是芳基且基团中的至少一个是烷基或环烷基,或其中
R1和R2是脂族性质的,并与磷原子一起互相连接形成具有4至6个环成员的杂环环,其中R3是具有最多4个碳原子的烷基。
合适的叔有机膦是例如具有直链脂族取代基的叔膦,如三甲基膦、三乙基膦、三-正丙基膦、三丙基膦、二丁基乙基膦、三-正丁基膦、三异丁基膦、三-叔丁基膦、戊基二甲基膦、戊基二乙基膦、戊基二丙基膦、戊基二丁基膦、戊基二己基膦、二戊基甲基膦、二戊基乙基膦、二戊基丙基膦、二戊基丁基膦、二戊基己基膦、二戊基辛基膦、三戊基膦、己基二甲基膦、己基二乙基膦、己基二丙基膦、己基二丁基膦、二己基甲基膦、二己基乙基膦、二己基丙基膦、二己基丁基膦、三己基膦、三辛基膦、三苄基膦、苄基二甲基膦、二甲基苯基膦或丁基磷杂环戊烷。
适用于本发明的方法的另外的叔有机膦是例如从EP 1 422 223 A1中获知的具有至少一个直接键合到磷上的脂环族基团的叔膦,例如环戊基二甲基膦、环戊基二乙基膦、环戊基二正丙基膦、环戊基二异丙基膦、具有任意异构丁基的环戊基二丁基膦、具有任意异构己基的环戊基二己基膦、具有任意异构辛基的环戊基二辛基膦、二环戊基甲基膦、二环戊基乙基膦、二环戊基-正丙基膦、二环戊基异丙基膦、具有任意异构丁基的二环戊基丁基膦、具有任意异构己基的二环戊基己基膦、具有任意异构辛基的二环戊基辛基膦、三环戊基膦、环己基二甲基膦、环己基二乙基膦、环己基二正丙基膦、环己基二异丙基膦、具有任意异构丁基的环己基二丁基膦、具有任意异构己基的环己基二己基膦、具有任意异构辛基的环己基二辛基膦、二环己基甲基膦、二环己基乙基膦、二环己基-正丙基膦、二环己基异丙基膦、具有任意异构丁基的二环己基丁基膦、具有任意异构己基的二环己基己基膦、具有任意异构辛基的二环己基辛基膦和三环己基膦。
用于本发明的方法的另外合适的叔有机膦是例如从EP 1 982 979 A1中获知并具有一个或两个直接键合到磷上的叔烷基的叔膦,例如叔丁基二甲基膦、叔丁基二乙基膦、叔丁基二正丙基膦、叔丁基二异丙基膦、具有任意异构丁基作为非叔丁基的叔丁基二丁基膦、具有任意异构己基但其中己基中的最多一个具有直接键合到磷上的叔碳原子的叔丁基二己基膦、具有任意异构辛基但其中辛基中的最多一个具有直接键合到磷上的叔碳原子的叔丁基二辛基膦、二叔丁基甲基膦、二叔丁基乙基膦、二叔丁基正丙基膦、二叔丁基异丙基膦、其中非叔丁基可以是正丁基、异丁基、2-丁基或环丁基的二叔丁基丁基膦、具有任意异构己基(其没有直接键合到磷上的叔碳原子)的二叔丁基己基膦、具有任意异构辛基(其没有直接键合到磷上的叔碳原子)的二叔丁基辛基膦、叔戊基二甲基膦、叔戊基二乙基膦、叔戊基二正丙基膦、叔戊基二异丙基膦、具有任意异构丁基但其中丁基中的最多一个是叔丁基的叔戊基二丁基膦、具有任意异构己基但其中己基中的最多一个具有直接键合到磷上的叔碳原子的叔戊基二己基膦、具有任意异构辛基但其中辛基中的最多一个具有直接键合到磷上的叔碳原子的叔戊基二辛基膦、二叔戊基乙基膦、二叔戊基乙基膦、二叔戊基正丙基膦、二叔戊基异丙基膦、其中丁基可以是正丁基、异丁基、2-丁基或环丁基的二叔戊基丁基膦、具有任意异构己基(其没有直接键合到磷上的叔碳原子)的二叔戊基己基膦、具有任意异构辛基(其没有直接键合到磷上的叔碳原子)的二叔戊基辛基膦、金刚烷基二甲基膦、金刚烷基二乙基膦、金刚烷基二正丙基膦、金刚烷基二异丙基膦、具有任意异构丁基但其中丁基中的最多一个具有直接键合到磷上的叔碳原子的金刚烷基二丁基膦、具有任意异构己基但其中己基中的最多一个具有直接键合到磷上的叔碳原子的金刚烷基二己基膦、具有任意异构辛基但其中辛基中的最多一个具有直接键合到磷上的叔碳原子的金刚烷基二辛基膦、二金刚烷基甲基膦、二金刚烷基乙基膦、二金刚烷基正丙基膦、二金刚烷基异丙基膦、其中丁基可以是正丁基、异丁基、2-丁基或环丁基的二金刚烷基丁基膦、具有任意异构己基(其没有直接键合到磷上的叔碳原子)的二金刚烷基己基膦、以及具有任意异构己基(其没有直接键合到磷上的叔碳原子)的二金刚烷基辛基膦。
优选的是,该催化剂含有选自所提到的具有直链脂族取代基的叔膦的至少一种化合物。
非常特别优选的膦催化剂是三正丁基膦和/或三辛基膦或其混合物。
可由根据本发明的灌封料制造具有极高硬度的组件。
根据本发明的灌封料是单组分体系。不同于双组分体系,不必精确遵循两个反应搭档之间的化学计量比以获得良好结果。根据本发明的灌封料中的所用催化剂浓度的轻微偏差可能导致适用期和固化时间的轻微变化,但不损害最终材料的性质。
尽管使用固有地具有相对高粘度的脂族多异氰酸酯,但该灌封料甚至在高填料含量下仍表现出如此低的粘度,以使得可以在没有较大问题的情况下加工。
此外,根据本发明的灌封料具有小于1小时的适用期,由此也简化它们的加工。在此,根据本发明的灌封料甚至在升高的温度下也具有至少1小时的适用期。因此,固有低粘度和在升高的温度下的长适用期的组合极大简化根据本发明的灌封料的加工,特别是脱气。
根据本发明的灌封料与已知聚氨酯灌封料相比还具有低火灾危险。
用途
在另一个实施方案中,本发明设计如本申请的上文定义的灌封料作为电灌封料,即用于生产电气组件的用途。
该电气组件优选选自变压器、绝缘体、电容器、半导体、用于保护电缆接头的套筒和地下电缆分支。
即使少数上述电气组件在某些应用领域中可不受电灌封料的保护使用,但术语“电气组件的生产”也涉及将电气组件的至少一部分包埋在根据本发明的灌封料中的方法。在本申请中,最终电气组件因此含有根据本发明的灌封料。
方法
在再另一个实施方案中,本发明涉及生产电气组件的方法,其含有步骤
a) 提供具有至少3:1的异氰酸酯基团与异氰酸酯反应性基团的摩尔比和最高10重量%的溶剂含量的浇铸树脂,其含有
(i) 至少一种具有至少15重量%的异氰酸酯含量的单体或低聚多异氰酸酯A;
(ii) 至少一种含氧化硅单元的无机填料B,其具有根据DIN EN ISO 787-5(1995年10月)测定的最高25 g/100 g的油值和至少4的莫氏硬度;和
(iii) 至少一种三聚催化剂C;
b) 用方法步骤a)中提供的浇铸树脂灌封尚未包埋的电气组件;
c) 所述浇铸树脂的催化三聚。
在本申请中,“提供”浇铸树脂被理解为仅是指在方法步骤a)结束时提供所提到的浇铸树脂以使其适用于灌封并可催化三聚。
尚未包埋的电气组件的灌封可通过现有技术中已知用于灌封料,特别是电灌封料的所有方法进行。
催化三聚在使得所选三聚催化剂C实现异氰酸酯基团的交联以提供异氰脲酸酯基团的反应条件下进行。在此,在温度敏感的电气组件的情况下,优选遵循对所涉组件无害的反应混合物的温度上限。
“催化三聚”是其中多异氰酸酯A中包含的异氰酸酯基团与彼此或与已存在的氨基甲酸酯基团反应以形成选自脲二酮、异氰脲酸酯、脲基甲酸酯、缩二脲、亚氨基噁二嗪二酮和噁二嗪三酮结构的至少一种结构的过程。在此消耗最初存在于多异氰酸酯A中的异氰酸酯基团。通过上述基团的形成,多异氰酸酯A中包含的单体和低聚多异氰酸酯连接形成聚合物网络。
优选的是,反应混合物中包含的异氰酸酯基团的交联主要通过多异氰酸酯A中存在的游离异氰酸酯基团的至少50摩尔%,优选至少60摩尔%,特别优选至少70摩尔%,尤其是至少80摩尔%,非常特别优选90摩尔%的三聚以提供异氰脲酸酯结构单元来进行。最终的聚异氰脲酸酯材料因此将相应比例的最初包含于多异氰酸酯A中的氮结合在异氰脲酸酯结构内。但是,通常发生副反应,尤其是形成脲二酮、脲基甲酸酯和/或亚氨基噁二嗪二酮结构的那些,并且甚至可专门用于有利地影响例如所得聚异氰脲酸酯材料的玻璃化转变温度(Tg)。
如果不必由于温度敏感组件而遵循较低温度,优选在50℃至200℃,更优选80℃至180℃,再更优选100℃至150℃的温度下进行催化三聚。
在异氰酸酯基团的交联过程中,保持上述温度,直至在异氰酸酯基团的交联开始时存在于根据本发明的半成品中的游离异氰酸酯基团的至少50摩尔%,优选至少75摩尔%,再更优选至少90摩尔%已被消耗。可通过在异氰酸酯基团的交联开始时存在的异氰酸酯组分A中的异氰酸酯基团的含量与反应产物中的异氰酸酯基团的含量的比较,例如通过借助ATR-IR光谱法比较在大约2270 cm-1的异氰酸酯谱带的强度来测定仍存在的异氰酸酯基团的百分比。
在另一个实施方案中,本发明涉及通过如上文定义的方法制成的电气组件。
由该浇铸树脂形成的聚合物基质的特征优选在于发生5重量%的质量损失时的温度为至少370℃,优选至少400℃,最优选至少420℃。
下列实施例仅用于例示本发明。它们不应以任何方式限制权利要求书的保护范围。
实施例
所用原材料
异氰酸酯1: 除使用2-乙基己醇代替2-乙基-1,3-己二醇作为催化剂溶剂外,根据EP-A 330 966的实施例11制成的含异氰脲酸酯基团的HDI多异氰酸酯。在42重量%的粗制混合物的NCO含量下通过加入磷酸二丁酯终止反应。随后,通过在130℃的温度和0.2毫巴的压力下的薄膜蒸馏分离出未转化的HDI。
NCO含量: 23.0重量%
NCO官能度: 3.2
单体HDI: 0.1重量%
粘度(23℃): 1200 mPas
密度(20℃): 1.17 g/cm³。
低聚结构类型的分布:
异氰脲酸酯: 89.7摩尔%
亚氨基噁二嗪二酮 2.5摩尔%
脲二酮 2.7摩尔%
脲基甲酸酯: 5.1摩尔%。
异氰酸酯2: 是通过双官能聚丙二醇聚醚(OH值 = 515 mg KOH/g)与过量HDI在80℃的温度下的反应制成的异氰酸酯封端预聚物。在建立恒定NCO含量后,通过加入磷酸二丁酯终止反应。随后,通过在130℃的温度和0.2毫巴的压力下的薄膜蒸馏分离出未转化的HDI。
NCO含量: 12.5重量%
NCO官能度: 2.1
单体HDI: < 0.5重量%
粘度(23℃): 4250 mPas
密度(20℃): 1.10 g/cm³。
异氰酸酯3: 是二苯甲烷4,4'-二异氰酸酯(MDI)与异构体和更高官能同系物的低粘度混合物
NCO含量: 31.5重量%
当量: 133 g/val
粘度(23℃): 90 mPas
密度(20℃): 1.23 g/cm³。
多元醇1: 是通过1,2-丙二醇的丙氧基化制成的线性聚丙二醇醚多元醇
羟值: 520 mg KOH/g
粘度(25℃): 55 mPas
密度(25℃): 1.00 g/cm³。
多元醇2: 甘油(1,2,3-丙三醇)以99.0%的纯度获自Calbiochem公司。
填料1: Silbond 126 EST是由环氧硅烷涂覆的石英填料并获自Quarzwerke GmbH公司。根据技术数据表,该填料吸收11克油/100克填料(DIN ISO 787-5);莫氏硬度为7。
填料2: Microdol 1-KN是白云石填料并获自Omya公司。根据技术数据表,该填料吸收15克油/100克填料(ISO 787/5)。根据维基百科(2019年02月检索),白云石的莫氏硬度为3.5-4。
填料3: Unispar PG W13是长石填料并获自Sibelco公司。根据技术数据表,该填料吸收22克油/100克填料(ISO 787/5);莫氏硬度为6.2。
填料4: Unispar PG W20是长石填料并获自Sibelco公司。根据技术数据表,该填料吸收19克油/100克填料(ISO 787/5);莫氏硬度为6.2。
填料5 Omycarb 2T-AV是碳酸钙填料并获自Omya公司。根据技术数据表,该填料吸收16克油/100克填料(ISO 787/5)。根据维基百科(2019年2月检索),碳酸钙(石灰石)的莫氏硬度为3。
填料6 Silbond 800 EST是由环氧硅烷涂覆的石英填料并获自Quarzwerke GmbH公司。根据技术数据表,该填料吸收26克油/100克填料(ISO 787/5)。
填料7 Silbond 6000 MST是由甲基丙烯酰基硅烷涂覆的方石英填料并获自Quarzwerke GmbH公司。根据技术数据表,该填料吸收27克油/100克填料(ISO 787/5)。
填料8 Sikron SF 800是石英填料并获自Quarzwerke GmbH公司。根据技术数据表,该填料吸收28克油/100克填料(ISO 787/5)。
填料9 Chinafill 200是高岭土填料并获自Amberger Kaolinwerke Eduard KickGmbH & Co. KG公司。根据技术数据表,该填料吸收46克油/100克填料(ISO 787/5)。根据维基百科(2019年02月检索),高岭土的莫氏硬度为2.5。
填料10 Silitin Z 86是微粒二氧化硅和层状高岭石的混合物并获自HoffmannMineral GmbH公司。根据技术数据表,该填料吸收55克油/100克填料(ISO 787/5);二氧化硅部分的莫氏硬度为7且高岭石部分的莫氏硬度为2.5。
填料11 Silbond 006 MST是由甲基丙烯酰基硅烷涂覆的方石英填料并获自Quarzwerke GmbH公司。根据技术数据表,该填料吸收21克油/100克填料(ISO 787/5);莫氏硬度为6.5。
在加工前,填料在定期搅拌下在80℃下干燥12小时。
催化剂1: Desmorapid AP 100获自Covestro AG公司。
催化剂2: 三辛基膦以97%的纯度获自abcr GmbH公司。
催化剂3: 是乙酸钾、[18]冠醚-6和二乙二醇的1.0: 2.7: 17.6比率的混合物(以PA品质获自Sigma-Aldrich并按供应态使用)。
催化剂4: Jeffcat Z-110获自Huntsman公司。
电性质的测定:
使用基于ASTM D 257(2007年5月)运行的Keithley Model 8009仪器测定材料的电性质。在25℃下进行测量。
玻璃化转变温度的测定:
根据DIN EN 61006(2004年11月)用Mettler DSC 12E(Mettler Toledo GmbH,Gießen, 德国)通过DSC(差示扫描量热法)测定玻璃化转变温度。通过铟和铅的熔融起始温度实施校准。将10毫克物质称入到标准胶囊中。通过以20 K/min的加热速率从-50℃至+200℃的两次加热运行和随后以20 K/min的冷却速率冷却,实施测量。借助液氮实施冷却。所用吹扫气体是氮气。所示值在每种情况下基于第二加热曲线的评估。
质量损失的测定:
根据DIN EN ISO 11358-1:2014-10通过TGA(热重分析)测定质量损失。为此在TGA-8000热重分析仪(Perkin-Elmer)中将大约5.5毫克产物在开放铂坩埚中在恒定氮气流下从25℃加热到600℃。加热速率为20 K/分钟。评估经测量时间累积的质量损失达到5重量%时的温度。
加工时间的测定:
为了测定加工时间,混合两种组分并在流变仪中在60℃下测量1小时。所示的粘度值是在正好1小时后测定的值。使用AntonPaar公司的MCR301流变仪。使用具有珀尔帖加热C-PTD200的板/板系统PP25。
测量配置:频率f = 1 Hz;振幅γ = 5%
T = 60℃,60 min。
肖氏硬度的测定:
使用Zwick 3100肖氏硬度测试仪(来自Zwick公司)在23℃和50%空气湿度下根据DIN 53505(2000年8月)测量肖氏硬度。
Claims (13)
1.浇铸树脂,其具有至少3:1的异氰酸酯基团与异氰酸酯反应性基团的摩尔比和最高10重量%的溶剂含量,其中所述浇铸树脂含有
(i) 至少一种具有至少15重量%的异氰酸酯含量的单体或低聚多异氰酸酯A;
(ii) 至少一种含氧化硅单元的无机填料B,其具有根据DIN EN ISO 787-5(1995年10月)测定的最高25 g/100 g的油值和至少4的莫氏硬度;和
(iii) 至少一种三聚催化剂C。
2.如权利要求1中所述的浇铸树脂,其中基于其总重量计,多异氰酸酯A在至少70重量%的程度上由仅具有脂族和/或脂环族键合的异氰酸酯基团的多异氰酸酯组成。
3.如权利要求1或2中所述的浇铸树脂,其中所述无机填料具有至少6的莫氏硬度。
4.如权利要求1至3任一项中所述的浇铸树脂,其中所述反应混合物在至少30重量%的程度上由无机填料B组成。
5.如权利要求4中所述的浇铸树脂,其中所述反应混合物在至少65重量%的程度上由无机填料B组成。
6.如权利要求1至5任一项中所述的浇铸树脂,其中所述三聚催化剂C催化异氰酸酯基团的交联以提供异氰脲酸酯基团。
7.如权利要求1至6任一项中所述的浇铸树脂,其特征在于在最多65重量%的无机填料B的含量下,所述浇铸树脂在60℃下储存1小时后具有最高150 Pas的粘度。
8.如权利要求7中所述的浇铸树脂,其中所述多异氰酸酯A具有在25℃下至少500 mPas且最高20000 mPas的粘度。
9.如权利要求1至8任一项中所述的浇铸树脂用于生产电气组件的用途。
10.如权利要求9中所述的用途,其中所述电气组件选自变压器、绝缘体、电容器、半导体、用于保护电缆接头和地下电缆分支的套筒。
11.生产电气组件的方法,其含有步骤
a) 提供如权利要求1至8任一项中定义的浇铸树脂;
b) 用方法步骤a)中提供的浇铸树脂灌封尚未包埋的电气组件;
c) 所述浇铸树脂的催化三聚。
12.通过如权利要求11中所述的方法制成的电气组件。
13.如权利要求12中所述的电气组件,其中由固化的浇铸树脂形成的聚合物基质的特征在于发生5重量%的质量损失时的温度为至少370℃。
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PCT/EP2020/055037 WO2020174009A1 (de) | 2019-02-27 | 2020-02-26 | Polyisocyanuratwerkstoffe als elektrovergussmassen |
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EP (1) | EP3931185A1 (zh) |
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- 2020-02-26 WO PCT/EP2020/055037 patent/WO2020174009A1/de unknown
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