CN117136205A - 多异氰脲酸酯预浸料及由其生产的纤维复合材料组分 - Google Patents
多异氰脲酸酯预浸料及由其生产的纤维复合材料组分 Download PDFInfo
- Publication number
- CN117136205A CN117136205A CN202280025110.6A CN202280025110A CN117136205A CN 117136205 A CN117136205 A CN 117136205A CN 202280025110 A CN202280025110 A CN 202280025110A CN 117136205 A CN117136205 A CN 117136205A
- Authority
- CN
- China
- Prior art keywords
- polymerizable composition
- alkyl
- polyisocyanate
- methyl
- polyisocyanates
- 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
Links
- 239000002131 composite material Substances 0.000 title abstract description 9
- 229920000582 polyisocyanurate Polymers 0.000 title abstract description 9
- 239000000835 fiber Substances 0.000 title description 25
- 239000011495 polyisocyanurate Substances 0.000 title description 6
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 118
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 118
- 239000000203 mixture Substances 0.000 claims abstract description 73
- 238000000034 method Methods 0.000 claims description 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 36
- 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 claims description 28
- 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 claims description 28
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 19
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims description 17
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 16
- 239000011265 semifinished product Substances 0.000 claims description 16
- 238000005829 trimerization reaction Methods 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims description 9
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical compound O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 239000011256 inorganic filler Substances 0.000 claims description 4
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000012784 inorganic fiber Substances 0.000 claims description 3
- 239000012766 organic filler Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 description 24
- -1 mercapto, carboxyl Chemical group 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 16
- 125000005442 diisocyanate group Chemical group 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 11
- 239000013638 trimer Substances 0.000 description 11
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 9
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 229910052751 metal Chemical class 0.000 description 8
- 239000002184 metal Chemical class 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 239000004814 polyurethane Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 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 7
- 238000003860 storage Methods 0.000 description 7
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 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 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 238000012544 monitoring process Methods 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 159000000001 potassium salts Chemical class 0.000 description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- 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 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 239000002585 base Substances 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
- 230000009977 dual effect Effects 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000008054 signal transmission Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-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
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 2
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 2
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000005643 Pelargonic acid Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical class CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical class CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229960002446 octanoic acid Drugs 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 150000003071 polychlorinated biphenyls Chemical class 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001955 polyphenylene ether Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229960000380 propiolactone Drugs 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 229940116423 propylene glycol diacetate Drugs 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 229940005605 valeric acid Drugs 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 1
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 description 1
- WZZDGHUQRSGHLQ-UHFFFAOYSA-N 1,3-diisocyanato-5,7-dimethyladamantane Chemical compound C1C(C2)(C)CC3(N=C=O)CC1(C)CC2(N=C=O)C3 WZZDGHUQRSGHLQ-UHFFFAOYSA-N 0.000 description 1
- MLXLDKWQJYBKOH-UHFFFAOYSA-N 1,3-diisocyanatoadamantane Chemical compound C1C(C2)CC3CC1(N=C=O)CC2(N=C=O)C3 MLXLDKWQJYBKOH-UHFFFAOYSA-N 0.000 description 1
- AGJCSCSSMFRMFQ-UHFFFAOYSA-N 1,4-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=C(C(C)(C)N=C=O)C=C1 AGJCSCSSMFRMFQ-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 description 1
- YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 description 1
- WXIOQJUEBPUFHH-UHFFFAOYSA-N 1-isocyanato-4-(2-isocyanatopropan-2-yl)-1-methylcyclohexane Chemical compound O=C=NC(C)(C)C1CCC(C)(N=C=O)CC1 WXIOQJUEBPUFHH-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical class OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- MPARHIHLIXVYMF-UHFFFAOYSA-M 2,2-bis(hydroxymethyl)butyl-(2-hydroxyethyl)-dimethylazanium;hydroxide Chemical compound [OH-].CCC(CO)(CO)C[N+](C)(C)CCO MPARHIHLIXVYMF-UHFFFAOYSA-M 0.000 description 1
- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LSYBWANTZYUTGJ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl-methylamino]ethanol Chemical compound CN(C)CCN(C)CCO LSYBWANTZYUTGJ-UHFFFAOYSA-N 0.000 description 1
- HHRGNKUNRVABBN-UHFFFAOYSA-N 2-[2-hydroxyethyl(propan-2-yl)amino]ethanol Chemical compound OCCN(C(C)C)CCO HHRGNKUNRVABBN-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- KIZQNNOULOCVDM-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)CCO KIZQNNOULOCVDM-UHFFFAOYSA-M 0.000 description 1
- UUNHRGSUOBTBKW-UHFFFAOYSA-M 2-hydroxypropanoate;tetramethylazanium Chemical compound C[N+](C)(C)C.CC(O)C([O-])=O UUNHRGSUOBTBKW-UHFFFAOYSA-M 0.000 description 1
- BHIZVZJETFVJMJ-UHFFFAOYSA-N 2-hydroxypropyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(C)O BHIZVZJETFVJMJ-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- ZDKYYMRLZONTFK-UHFFFAOYSA-N 3,4-bis(isocyanatomethyl)bicyclo[2.2.1]heptane Chemical compound C1CC2(CN=C=O)C(CN=C=O)CC1C2 ZDKYYMRLZONTFK-UHFFFAOYSA-N 0.000 description 1
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- MTPUFPIZVDRORX-UHFFFAOYSA-N 5,5-dimethylhexane-2,4-diol Chemical compound CC(O)CC(O)C(C)(C)C MTPUFPIZVDRORX-UHFFFAOYSA-N 0.000 description 1
- RIAHASMJDOMQER-UHFFFAOYSA-N 5-ethyl-2-methyl-1h-imidazole Chemical compound CCC1=CN=C(C)N1 RIAHASMJDOMQER-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 244000198134 Agave sisalana Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 229920002748 Basalt fiber Polymers 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Chemical class 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- RYTJSFWWRLGZIZ-UHFFFAOYSA-N ClC1C(CS(=O)C1)(Cl)Cl Chemical compound ClC1C(CS(=O)C1)(Cl)Cl RYTJSFWWRLGZIZ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UXDDRFCJKNROTO-UHFFFAOYSA-N Glycerol 1,2-diacetate Chemical compound CC(=O)OCC(CO)OC(C)=O UXDDRFCJKNROTO-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920005372 Plexiglas® Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- PRKQVKDSMLBJBJ-UHFFFAOYSA-N ammonium carbonate Chemical group N.N.OC(O)=O PRKQVKDSMLBJBJ-UHFFFAOYSA-N 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000011162 ammonium carbonates Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- KFSZGBHNIHLIAA-UHFFFAOYSA-N benzyl(trimethyl)azanium;hydron;fluoride Chemical compound F.C[N+](C)(C)CC1=CC=CC=C1 KFSZGBHNIHLIAA-UHFFFAOYSA-N 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- NRYUXUHIGUILJE-UHFFFAOYSA-N bis[4-(2-isocyanatopropan-2-yl)phenyl] carbonate Chemical compound C1=CC(C(C)(N=C=O)C)=CC=C1OC(=O)OC1=CC=C(C(C)(C)N=C=O)C=C1 NRYUXUHIGUILJE-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Chemical class OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 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 1
- 230000008859 change Effects 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 1
- ISXUHJXWYNONDI-UHFFFAOYSA-L dichloro(diphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](Cl)(Cl)C1=CC=CC=C1 ISXUHJXWYNONDI-UHFFFAOYSA-L 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- DQKGOGJIOHUEGK-UHFFFAOYSA-M hydron;2-hydroxyethyl(trimethyl)azanium;carbonate Chemical compound OC([O-])=O.C[N+](C)(C)CCO DQKGOGJIOHUEGK-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 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 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- RIEABXYBQSLTFR-UHFFFAOYSA-N monobutyrin Chemical compound CCCC(=O)OCC(O)CO RIEABXYBQSLTFR-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- XMAXUBOLEVIRGX-UHFFFAOYSA-N phosphanium;fluoride Chemical class [F-].[PH4+] XMAXUBOLEVIRGX-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- GDNULDIPPDQVRH-UHFFFAOYSA-N potassium;pyrrolidin-2-one Chemical class [K].O=C1CCCN1 GDNULDIPPDQVRH-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940026235 propylene glycol monolaurate Drugs 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- UAKCMIIOSJFOTD-UHFFFAOYSA-M sodium;3-oxobutanoate Chemical compound [Na+].CC(=O)CC([O-])=O UAKCMIIOSJFOTD-UHFFFAOYSA-M 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Substances [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- JDRNNVMPFUXWQD-UHFFFAOYSA-M tetraethylphosphanium;fluoride Chemical compound [F-].CC[P+](CC)(CC)CC JDRNNVMPFUXWQD-UHFFFAOYSA-M 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- VBHJAIGGLJOOLJ-UHFFFAOYSA-M tetramethylphosphanium;fluoride Chemical compound [F-].C[P+](C)(C)C VBHJAIGGLJOOLJ-UHFFFAOYSA-M 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical class CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-O trioctylazanium Chemical compound CCCCCCCC[NH+](CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-O 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/02—Layered products essentially comprising sheet glass, or glass, slag, or like fibres in the form of fibres or filaments
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
- B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
- B32B5/26—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer another layer next to it also being fibrous or filamentary
-
- 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
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
- C08G18/092—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7875—Nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/7887—Nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring having two nitrogen atoms in the ring
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/794—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aromatic isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2250/00—Layers arrangement
- B32B2250/05—5 or more layers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/02—Composition of the impregnated, bonded or embedded layer
- B32B2260/021—Fibrous or filamentary layer
- B32B2260/023—Two or more layers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/04—Impregnation, embedding, or binder material
- B32B2260/046—Synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/101—Glass fibres
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2475/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0346—Organic insulating material consisting of one material containing N
Abstract
本发明涉及包含两种不同类型的多异氰酸酯的多异氰酸酯组合物,它们在制备预浸料和由所述预浸料制备的复合多异氰脲酸酯中的用途。
Description
本发明涉及包含两种不同类型的多异氰酸酯的多异氰酸酯组合物,它们在制备预浸料(prepregs)和由所述预浸料制成的复合多异氰脲酸酯中的用途。
用纤维如碳纤维或玻璃纤维增强的复合材料由于其特性而受到关注,即尽管其重量轻,但具有良好的耐热性和良好的机械强度。它们已被更广泛地应用于各种结构应用,例如印制电路板、底盘以及汽车和飞机的各种构件。常用于模塑这种纤维增强树脂复合材料的方法使用被称为预浸料的中间材料。在预浸料中,增强纤维是用热固性树脂浸渍的。经浸渍的纤维然后通过压热模塑(autoclave molding)或压力模塑(press molding)进行固化和成型。
通常,用于预浸料的树脂要求具有即使在室温下的储存稳定性和通过加热等的可固化性。另外的所需的特征是可以将所述预浸料切割成一定尺寸,而不会使切割工具被经常粘性的基质材料污染。通常,经常使用热固性树脂,例如环氧树脂组合物。然而,含有环氧树脂的预浸料需要在低温下储存是不利的,因为固化已经在常温下进行。基于环氧体系的预浸料和由其制备的复合组分,描述于例如EP 0981427中。
在过去的几年里,还开发了特征为室温下的储存稳定性的聚氨酯基预浸料。与基于环氧树脂的预浸料不同,储存稳定的PU预浸料在加工前不需要以昂贵的方式冷却。在DE10200900193.3和DE 102009001806.9中,描述了一种生产储存稳定的预浸料的方法,所述预浸料基本上由A)至少一种纤维载体和B)作为所述基质材料的至少一种粉末形式的反应性聚氨酯组合物组成。
环氧基预浸料最大的应用领域之一是制造覆铜层压板(CCL)和印制电路板(PCB)。尽管上述聚氨酯基预浸料可以解决预浸料的储存稳定性问题,但由于较高的介电常数(Dk)和耗散因子(Df),其介电性能不能满足高频信号传输的综合要求。这是由于在最终固化树脂中存在大量极性氨基甲酸酯基团。特别是在射频基站、雷达天线等的高频(2GHz及以上)通信领域,对信号传输损耗和信号传输延迟提出了更高的要求。用于PCB的聚氨酯预浸料应用的另一个障碍是它们的低耐热性,例如在WO 2012/038105中报道的PU基预浸料的玻璃化转变温度Tg仅为约70℃,并且在WO 2013/13704中,最终固化树脂的Tg为146℃,这两个值都太低,无法满足PCB的通常大于150℃的要求。
本发明的目标是提供预浸料,其可以通过简单的工艺生产并且在室温下稳定储存数周。此外,所述预浸料意在几乎无粘性,从而可以容易地被进一步加工。本发明的进一步的目标是提供树脂组合物,其可以实现具有低介电性能和高玻璃化转变温度的印制电路板。
已经描述了基于双重固化机理的多异氰脲酸酯材料。WO 2018/087395公开了丙烯酸酯和多异氰酸酯的组合,从而可以获得两种不同的交联机理,它们可以通过不同的机理(电离辐射和热)活化。WO 2020/152107公开了具有小比例多元醇或多胺的多异氰酸酯的用途。在第一步骤中,通过第一催化剂在较低温度下形成氨基甲酸酯或脲基团。该反应受到可用胺或羟基的数量的限制。在第二步骤中,使用更高的温度由剩余的异氰酸酯基团来形成异氰脲酸酯基团。
这两种机理都可以用于提供预浸料。然而,在这两种情况下,必须接受的是,所得到的材料包含除异氰脲酸酯基团之外的相关量的交联基团。根据应用,这可能是不需要的,因为异氰脲酸酯基团具有特别有利的性质。
因此,本发明下的问题在于提供双重固化机理,其允许在两个不同的固化步骤中制备多异氰脲酸酯塑料,从而可以在第一固化步骤中获得储存稳定的半成品并在第二固化步骤中完全固化。
该问题通过权利要求和以下描述中限定的实施方案来解决。
在第一个实施方案中,本发明涉及一种不含异氰酸酯反应性基团或异氰酸酯组分的异氰酸酯基团与异氰酸酯反应性基团的摩尔比为至少2.0:1.0的可聚合组合物,其包含
a)至少一种脂族多异氰酸酯;
b)至少一种脂环族多异氰酸酯;和
c)至少一种三聚催化剂;
其中所述脂环族多异氰酸酯的浓度为基于所述可聚合组合物中存在的所有多异氰酸酯的总质量计的25重量%-75重量%;并且
其中所述组合物中脲二酮形成催化剂的浓度不大于所述可聚合组合物中存在的脲二酮形成催化剂和三聚催化剂的总质量的10重量%。
“可聚合组合物”是包含上文限定的组分,任选地包含下文列出的进一步的组分的组合物。在“可聚合组合物”中,所述组分以这样的方式混合,使得所述组合物可用于通过简单加热形成聚合物。
本发明的可聚合组合物特别适合用于预浸料材料的制备。预浸料材料是包含热固性聚合物的材料,其已经部分固化,使得所述材料可以被处理或运输。然而,在预浸料的制备过程中,固化不得进行到所述材料变得太硬和太脆而无法处理(例如通过弯曲)的地步。在本发明的可聚合组合物中,这是通过至少两种具有不同反应性的不同多异氰酸酯的组合来实现的。因此,在较低温度下的第一固化步骤主要通过交联反应性更强的多异氰酸酯的异氰酸酯基团来产生所述预浸料,然后可以使用第二固化步骤来获得符合预期用途的坚硬且完全固化的材料。在上述多异氰酸酯中,芳族多异氰酸酯具有最高的反应性,芳脂族多异氰酸酯具有第二高的反应性,脂族多异氰酸酯具有第二低的反应性并且脂环族多异氰酸酯是反应性最低的物类。因此,为了实现本发明所需的双重固化机理,所述脂族多异氰酸酯必须与至少一种具有不同反应性的多异氰酸酯配对。满足这一要求的物类是脂环族、芳族和芳脂族多异氰酸酯。如果需要脂族多异氰酸酯与较慢固化物类的组合,则应将其与至少一种脂环族多异氰酸酯混合。如果希望脂族多异氰酸酯与较快固化物类的组合,则应将其与至少一种芳脂族和/或芳族多异氰酸酯混合。还可以将所述脂族多异氰酸酯与较快固化和较慢固化的多异氰酸酯组合。在本发明的优选实施方案中,所述可聚合组合物包含至少一种脂族多异氰酸酯和至少一种脂环族多氰酸酯。
优选至少一种脂族多异氰酸酯占所述可聚合组合物中存在的所有多异氰酸酯的总量的10重量%-80重量%,优选25重量%-65重量%。
脂环族多异氰酸酯的优选含量为25重量%-75重量%,更优选30重量%-70重量%。
在本发明的优选实施方案中,芳脂族和芳族多异氰酸酯占所述可聚合组合物中存在的所有多异氰酸酯的总量的不超过10重量%,更优选不超过5重量%。最优选地,所述可聚合组合物不含上述多异氰酸酯。
通过聚合本发明的可聚合组合物可获得的聚合物通过所述异氰酸酯基团彼此交联而非常充分地获得其有利性质。因此,对本发明至关重要的是,限制所述可聚合组合物中异氰酸酯基团与异氰酸酯反应性基团总量的比例,使得具有明显摩尔过量的异氰酸酯基团。所述异氰酸酯组分的异氰酸酯基团与反应性树脂中异氰酸酯反应性基团的摩尔比因此为至少2.0∶1.0,优选至少3.0∶1.0,更优选至少4.0∶1.0,且甚至更优选至少8.0∶1.0。所述组合物也可以不含异氰酸酯反应性基团。在本申请的上下文中“异氰酸酯反应性基团”是羟基、巯基、羧基和氨基、酰胺、氨基甲酸酯、酸酐和环氧化物。
在本发明的优选实施方案中,所述可聚合组合物还包含至少一种不含异氰酸酯反应性基团的有机溶剂,也被称为“惰性溶剂”。优选地,该溶剂的浓度使得所述可聚合组合物的粘度在100mPas和2000mPas之间。通常,如果所述可聚合组合物优选包含基于所有多异氰酸酯、所有三聚催化剂和所有溶剂的总和计的10重量%-50重量%的惰性溶剂,则可获得这样的值。
在本发明的另一个优选实施方案中,所述可聚合组合物还包含有机或无机填料。
这里使用的术语“多异氰酸酯”是指分子中含有两个或更多个异氰酸酯基团的化合物的统称(本领域技术人员将理解为是指具有一般结构-N=C=O的自由异氰酸酯基团)。这些多异氰酸酯的最简单和最重要的代表是二异氰酸酯。它们具有一般结构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。“多异氰酸酯组分”是指属于该物类的所有多异氰酸酯的总和。因此,“脂族多异氰酸酯组分”是指所述可聚合组合物中存在的所有脂族多异氰酸酯的总和,术语“芳族多异氰酸酯组分”是指所有芳族多异氰酸酯,并且术语“脂环族多异氰酸酯组分”是指所有脂环族多异氰酸酯的总和。
由于多官能度(≥2个异氰酸酯基团),可以使用多异氰酸酯来生产多种聚合物(例如聚氨酯、聚脲和多异氰脲酸酯)和低分子量化合物(例如具有脲二酮、异氰脲酯、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)。
本申请中的术语“多异氰酸酯”同样是指单体和/或低聚多异氰酸酯。然而,为了理解本发明的许多方面,区分单体二异氰酸酯和低聚多异氰酸酯是重要的。在本申请中提及“低聚多异氰酸酯”时,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分子形成的反应产物的化合物。
由单体二异氰酸酯制备低聚多异氰酸酯在这里也被称为单体二异氰酸酯的改性。这里使用的这种“改性”是指单体二异氰酸酯反应以生成具有脲二酮、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。
例如,六亚甲基二异氰酸酯(HDI)是“单体二异氰酸酯”,因为它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:
相比之下,由至少两个HDI分子形成并且仍然具有至少两个异氰酸酯基团的反应产物在本发明的范围内是“低聚多异氰酸酯”。这种“低聚多异氰酸酯”的代表是由单体HDI起始的,例如HDI异氰脲酸酯和HDI缩二脲,它们各自由三个单体HDI单元形成:
(理想化的结构式)
根据本发明,基于所述可聚合组合物中存在的所有多异氰酸酯的总量计,所述异氰酸酯基团的比例为至少15重量%。
原则上,单体和低聚多异氰酸酯同样地适用于本发明。因此,任何多异氰酸酯可以基本上由单体多异氰酸酯或基本上由低聚多异氰酸酯组成。可替代地,它可以包含任何所需混合比例下的低聚和单体多异氰酸酯。
然而,在本发明的优选实施方案中,在三聚反应中用作反应物的多异氰酸酯具有低水平的单体(即低水平的单体二异氰酸酯),并且已经含有低聚多异氰酸酯。如果所述多异氰酸酯组合物的单体含量过高,则第一固化步骤不会产生储存稳定的半成品。表达“具有低水平的单体”和“具有低含量的单体二异氰酸酯”在这里同义使用。
当多异氰酸酯的单体二异氰酸酯的比例为在每种情况下基于相应的多异氰酸酯的重量计的不超过20重量%,尤其是不超过15重量%或不超过10重量%时,确定了特别实际相关的结果。优选地,多异氰酸酯的单体二异氰酸酯含量为在每种情况下基于相应的多异氰酸酯的重量计的不超过5重量%,优选不超过2.0重量%,更优选不超过1.0重量%。当多异氰酸酯基本上不含单体二异氰酸酯时,确定了特别好的结果。“基本上不含”在这里是指单体二异氰酸酯的含量为基于多异氰酸酯的重量计的不超过0.5重量%。
在本发明的一个特别优选的实施方案中,每种异氰酸酯完全或在每种情况下基于相应的多异氰酸酯的重量计的至少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。这里优选低聚多异氰酸酯的含量为至少99重量%。该含量的低聚多异氰酸酯涉及所提供的多异氰酸酯。换言之,低聚多异氰酸酯在本发明的任何过程中都不是作为中间体形成的,而是在任何反应开始时就已经存在于可聚合组合物中。
具有低水平单体或基本上不含单体异氰酸酯的多异氰酸酯组合物可以通过在实际的改性反应之后,在每种情况下进行至少一个进一步的工艺步骤以除去未转化的过量的单体二异氰酸酯而获得。单体的这种去除可以通过本身已知的工艺以特别实用的方式进行,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萃取,例如脂族或脂环族烃,如戊烷、己烷、庚烷、环戊烷或环己烷。
在本发明的一个优选实施方案中,本发明的多异氰酸酯组分通过改性单体二异氰酸酯并随后除去未转化的单体而获得。
根据本发明,所述低聚多异氰酸酯可以尤其具有脲二酮、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。在本发明的一个实施方案中,所述低聚多异氰酸酯具有以下低聚结构类型或其混合物中的至少一种:
在本发明的一个优选实施方案中,使用脂族多异氰酸酯组分,其中该组分的异氰脲酸酯结构含量为基于脂族多异氰酸酯组分中存在的来自脲二酮、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的至少50摩尔%,优选至少60摩尔%,更优选至少70摩尔%,甚至更优选至少80摩尔%,甚至还更优选至少90摩尔%,以及尤其优选至少95摩尔%。
如果存在脂环族多异氰酸酯组分,还优选其异氰脲酸酯结构含量为基于存在于脂环族多异氰酸酯组分中的来自脲二酮、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的至少50摩尔%,优选至少60摩尔%,更优选至少70摩尔%,甚至更优选至少80摩尔%,甚至还更优选至少90摩尔%,以及尤其优选至少95摩尔%。
在本发明下的研究中已经发现,使用具有一定含量的异氰脲酸酯基团的低聚多异氰酸酯提高了最终产物的耐热性。
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多异氰酸酯中的比例可以例如通过NMR光谱学测定。
这里可以优选地使用13C NMR光谱学,优选以质子去耦的形式,因为所提及的低聚结构给出特征信号。
不考虑下层的低聚结构(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)如何,用于本发明的低聚多异氰酸酯优选具有2.0至5.0,优选2.3至4.5的(平均)NCO官能度。
当根据本发明要使用的相应的多异氰酸酯具有在每种情况下基于相应的多异氰酸酯重量计的8.0重量%-28.0重量%,优选14.0重量%-25.0重量%的异氰酸酯基团含量时,确定了具有特别实际相关的结果。
根据本发明要使用的具有脲二酮、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制备方法描述在例如J.Prakt.Chem.336(1994)185-200中;在DE-A 1 670 666、DE-A 1 954 093、DE-A 2 414 413、DE-A2 452 532、DE-A 2 641 380、DE-A 3 700 209、DE-A 3 900 053和DE-A 3 928 503中;或在EP-A 0 336205、EP-A 0 339 396和EP-A 0 798 299中。
由于本发明的有利效果需要存在不同的多异氰酸酯物类,这些物类在下文中进一步详细限定。
脂族多异氰酸酯
在脂族多异氰酸酯中,所有异氰酸酯基团都与作为开放碳链一部分的碳原子结合。这可以在一个或多个位点处是不饱和的。脂族结合的异氰酸酯基团优选结合在碳链的末端碳原子上。
根据本发明特别合适的脂族多异氰酸酯是1,4-二异氰酸根合丁烷(BDI)、1,5-二异氰酸根合戊烷(PDI)、1,6-二异氰酸根合己烷(HDI)、2-甲基-1,5-二异氰酸根合戊烷、l,5-二异氰酸根合-2,2-二甲基戊烷、2,2,4-或2,4,4-三甲基-1,6-二异氰酸根合己烷和1,10-二异氰酸酯癸烷及由其衍生的低聚物。
脂环族多异氰酸酯
在脂环族多异氰酸酯中,所有异氰酸酯基团都与作为闭合环的碳原子的一部分的碳原子结合。该环可以在一个或多个位点处是不饱和的,前提是它不会由于双键的存在而获得芳香性质。
根据本发明特别适合的脂环族多异氰酸酯是1,3-和1,4-二异氰酸根合环己烷、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、l-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)、l-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'-二异氰酸根合二环己基甲烷(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-l,l'-二(环己基)、4,4'-二异氰酸根合-3,3'-二甲基-l,l'-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、1,3-二异氰酸根合金刚烷和1,3-二甲基-5,7-二异氰酸根合金刚烷及由其衍生的低聚物。
芳脂族多异氰酸酯
在芳脂族多异氰酸酯中,所有异氰酸酯基团都与亚甲基结合,该亚甲基转而又与芳族环结合。
根据本发明特别适合的芳脂族多异氰酸酯是1,3-和1,4-双(异氰酸根合甲基)苯(苯二亚甲基二异氰酸酯;XDI)、1,3-和1,4-双(l-异氰酸根合-1-甲基乙基)苯(TMXDI)和双(4-(l-异氰酸根合-1-甲基乙基)苯基)碳酸酯及由其衍生的低聚物。
芳族多异氰酸酯
在芳族多异氰酸酯中,所有异氰酸酯基团都直接结合到作为芳族环一部分的碳原子上。
根据本发明特别合适的芳族多异氰酸酯是2,4-和2,6-二异氰酸根合甲苯(TDI)、2,4'和4,4'-二异氰酸根合二苯基甲烷(MDI)和1,5-二异氰酸根合萘及由其衍生的低聚物。
催化剂
本申请中所理解的“三聚催化剂”是催化异氰酸酯基团与异氰脲酸酯结构的加成反应的催化剂。优选所述催化剂将所述可聚合组合物中不超过20mol%,更优选不超过10mol%,且最优选不超过5mol%的异氰酸酯基团转化为脲二酮基团,因为这些基团不太稳定并且损害材料的化学和物理性质。此外,组合物中脲二酮形成催化剂的浓度优选不大于所述可聚合组合物中存在的脲二酮形成催化剂和三聚催化剂的总重量的10重量%,更优选不大于3重量%。最优选地,所述组合物不含脲二酮形成催化剂。
合适的三聚催化剂是例如简单的叔胺,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。合适的催化剂还包括GB 2 221 465中描述的羟烷基叔胺(tertiary hydroxyalkylamines),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中已知的由二环叔胺,例如DBU与低分子量的简单脂族醇的混合物组成的催化剂体系。
进一步的三聚催化剂是,例如,从DE-A 1 667 309、EP-A 0 013 880和EP-A 0 047452中已知的季铵氢氧化物,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)-l,4-二氮杂二环[2.2.2]辛烷氢氧化物(环氧乙烷和水在1,4-二氮杂二环[2.2.2]辛烷上的单加合物);从EP-A 37 65或EP-A 10 589中已知的羟烷基季铵氢氧化物,例如N,N,N-三甲基-N-(2-羟乙基)氢氧化铵;从DE-A 2631733、EP-A 0 671 426、EP-A1 599 526和US 4 789 705中已知的三烷基羟烷基铵羧酸盐,例如N,N,N-三甲基-N-2-羟丙基对叔丁基苯甲酸铵和N,N,N-三甲基-N-2-羟丙基2-乙基己酸铵;从EP-A 1 229 016中已知的苄基季铵羧酸盐,例如N-苄基-N,N-二甲基-N-乙基新戊酸铵、N-苄基-N,N-二甲基-N-乙基2-乙基己酸铵、N-苄基-N,N,N-三丁基2-乙基己酸铵、N,N-二甲基-N-乙基-N-(4-甲氧基苄基)2-乙基己酸铵或N,N,N-三丁基-N-(4-甲氧基苄基)新戊酸铵;从WO 2005/087828中已知的四取代的α-羟基羧酸铵,例如乳酸四甲基铵;从EP-A 0 339 396、EP-A 0379 914和EP-A 0 443 167中已知的季铵或鏻氟化物,例如具有C8-C10烷基的N-甲基-N,N,N-三烷基氟化铵、N,N,N,N-四正丁基氟化铵、N,N,N-三甲基-N-苄基氟化铵、四甲基氟化鏻、四乙基氟化鏻或四正丁基氟化鏻;从EP-A 0 798 299、EP-A 0 896 009和EP-A 0 962 455中已知的季铵和鏻多氟化物,例如苄基三甲基多氟化氢铵;从EP-A 0 668 271中已知并可通过叔胺与碳酸二烷基酯反应获得的烷基碳酸四烷基铵,或甜菜碱(betaine)结构的烷基碳酸季铵;从WO 1999/023128中已知的碳酸氢季铵,例如胆碱碳酸氢盐;从EP 0 102 482中已知并可由叔胺和磷酸的烷基化酯获得的季铵盐,这种盐的实例是三乙胺、DABCO或N-甲基吗啉与甲膦酸二甲酯的反应产物;或从WO 2013/167404中已知的内酰胺的四取代铵盐,例如己内酰胺三辛基铵或己内酰胺十二烷基三甲基铵。
合适的盐是已知的具有至多14个碳原子的直链或支化的烷烃羧酸,例如丁酸、戊酸、己酸、2-乙基己酸、庚酸、辛酸、壬酸和更高级的同系物的钠盐和钾盐。
同样适合作为三聚催化剂的是多种不同的金属化合物。合适的实例是在DE-A 3240613中描述为催化剂的锰、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;DE-A 3 219 608公开的具有至多10个碳原子的直链或支化的烷烃羧酸的钠盐和钾盐,例如丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸和十一烯酸的钠盐和钾盐;EP-A 0 100 129公开的具有2至20个碳原子的脂环族或芳族单羧酸和多羧酸的碱金属或碱土金属盐,例如苯甲酸钠或苯甲酸钾;GB-A 1 391 066和GB-A 1 386399公开的碱金属酚盐,例如酚钠或酚钾;GB 809 809公开的碱金属和碱土金属氧化物、氢氧化物、碳酸盐、醇盐和酚盐,可烯醇化化合物的碱金属盐和弱脂族或脂环族羧酸的金属盐,例如甲醇钠、乙酸钠、乙酸钾、乙酰乙酸钠、2-乙基己酸铅和环烷酸铅;EP-A 0 056 158和EP-A 0 056 159公开的与冠醚或聚醚醇络合的碱性碱金属化合物,例如EP-A 0 033 581公开的络合的羧酸钠或羧酸钾和/或吡咯烷酮钾盐;申请EP 13196508.9公开的钛、锆和/或铪的单核或多核络合物,例如四正丁醇锆、四-2-乙基己酸锆和四-2-乙基己醇锆,以及在European Polymer Journal,第16卷,147-148(1979)中描述的锡化合物类型,例如二氯化二丁基锡、二氯化二苯基锡、三苯基锡烷醇(triphenylstannanol)、乙酸三丁基锡、辛酸锡、二丁基(二甲氧基)锡烷和三丁基咪唑锡。
适用于本发明的方法的进一步的三聚催化剂可以在例如J.H.Saunders和K.C.Frisch,Polyurethanes Chemistry and Technology,第94页及以后(1962)和其中引用的文献中找到。
所述三聚催化剂可以单独或以任何所需的混合物彼此混合的形式用于根据本发明的方法。
同样特别合适的是具有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盐或碱土金属盐。任何上述羧酸的钾盐都是又更优选的。乙酸钾是特别优选的。
然而,WO 2016/170057、WO 2016/17059或WO 2016/170061中记载的所有催化剂原则上也是合适的,只要它们在上述温度范围内催化交联反应。
特别适合作为三聚催化剂的是式(I)的催化剂及其加合物。
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、支化的C5-烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的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。
在优选实施方案中,A为NR3,其中R3选自氢、甲基、乙基、丙基、异丙基、丁基和异丁基。R3优选为甲基或乙基。R3特别优选为甲基。
在该实施方案的第一变体中,B为OH,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。
在该实施方案的第二变体中,B为SH,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。
在该实施方案的第三变体中,B为NHR4,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。在该变体中,R4选自甲基、乙基和丙基。优选R4为甲基或乙基。R4特别优选为甲基。
在该实施方案的第四变体中,B为NH2,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。
在进一步优选实施方案中,A为氧。
在该实施方案的第一变体中,B为OH,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。
在该实施方案的第二变体中,B为SH,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。
在该实施方案的第三变体中,B为NHR4,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。在该变体中,R4选自甲基、乙基和丙基。优选R4为甲基或乙基。R4特别优选为甲基。
在该实施方案的第四变体中,B为NH2,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。
在又一个进一步优选的实施方案中,A为硫。
在该实施方案的第一变体中,B为OH,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。
在该实施方案的第二变体中,B为SH,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。
在该实施方案的第三变体中,B为NHR4,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。在该变体中,R4选自甲基、乙基和丙基。优选R4为甲基或乙基。R4特别优选为甲基。
在该实施方案的第四变体中,B为NH2,并且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、支化的C5烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的C7烷基。优选R1和R2彼此独立地为甲基或乙基。R1和R2特别优选为甲基。
同样合适的是式(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。
总括术语“加合物”应理解为是指式(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、硫代氨基甲酸酯和脲加合物。特别优选氨基甲酸酯加合物。当异氰酸酯与式(I)中限定的化合物的官能团B反应时,形成本发明所述的加合物。当B是羟基时,形成氨基甲酸酯加合物。当B是巯基时,形成硫代氨基甲酸酯加合物。并且当B是NH2或NHR4时,形成脲加合物。
合适的催化剂溶剂是例如对异氰酸酯基团呈惰性的溶剂,例如己烷、甲苯、二甲苯、氯苯、乙酸乙酯、乙酸丁酯、二乙二醇二甲醚、二丙二醇二甲醚、乙二醇单甲醚乙酸酯或乙二醇单乙醚乙酸酯、二乙二醇乙醚乙酸酯和二乙二醇丁醚乙酸酯、丙二醇单甲醚乙酸酯、乙酸l-甲氧基-2-丙酯、乙酸3-甲氧基正丁酯、丙二醇二乙酸酯、丙酮、甲乙酮、甲基异丁基酮、环己酮、内酯,例如β-丙内酯、γ-丁内酯、ε-己内酯和ε-甲基己内酯,以及溶剂例如N-甲基吡咯烷酮和N-甲基己内酰胺、1,2-碳酸亚丙基酯、二氯甲烷、二甲基亚砜、磷酸三乙酯或这些溶剂的任何所需混合物。
如果在所述可聚合组合物中使用催化剂溶剂,则优选使用具有对异氰酸酯呈反应性的基团并可并入所述多异氰脲酸酯树脂中的催化剂溶剂。这类溶剂的实例为一元或多元的简单醇,例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、正己醇、2-乙基-1-己醇、乙二醇、丙二醇、异构丁二醇、2-乙基己-1,3-二醇或甘油;醚醇,例如l-甲氧基-2-丙醇、3-乙基-3-羟甲基氧杂环丁烷、四氢糠醇、乙二醇单甲醚、乙二醇单乙醚、乙二醇单丁醚、二乙二醇单甲醚、二乙二醇单乙醚、二乙二醇单丁醚、二乙二醇、二丙二醇或其它液体更高分子量的聚乙二醇、聚丙二醇、混合的聚乙二醇/聚丙二醇及其单烷基醚;酯醇,例如乙二醇单乙酸酯、丙二醇单月桂酸酯、甘油单乙酸酯和二乙酸酯、甘油单丁酸酯或2,2,4-三甲基戊-1,3-二醇单异丁酸酯;不饱和醇,例如烯丙醇、1,1-二甲基烯丙醇或油醇;芳脂族醇,例如苄醇;N-单取代酰胺,例如N-甲基甲酰胺、N-甲基乙酰胺、氰基乙酰胺或2-吡咯烷酮,或这些溶剂的任何所需混合物。
溶剂
合适的溶剂必须是对异氰酸酯基团呈惰性的,即它们不得含有本申请中上文限定的异氰酸酯反应性基团。溶剂优选选自己烷、甲苯、二甲苯、氯苯、乙酸乙酯、乙酸丁酯、二乙二醇二甲醚、二丙二醇二甲醚、乙二醇单甲醚乙酸酯或乙二醇单乙醚乙酸酯、二乙二醇乙醚乙酸酯和二乙二醇丁醚乙酸酯、丙二醇单甲醚乙酸酯、乙酸l-甲氧基-2-丙酯、乙酸3-甲氧基正丁酯、丙二醇二乙酸酯、丙酮、甲乙酮、甲基异丁基酮、环己酮、内酯,例如β-丙内酯、γ-丁内酯、ε-己内酯和ε-甲基己内酯,N-甲基吡咯烷酮、N-甲基己内酰胺、1,2-碳酸亚丙基酯、二氯甲烷、二甲基甲酰胺、三氯乙烯、二甲基亚砜、磷酸三乙酯。更优选地,所述至少一种溶剂选自乙酸丁酯。
填料
可以使用本领域已知的任何类型的无机或无机填料。优选的无机填料选自金属氧化物、亚硝酸盐、硅化物,特别是二氧化硅,硼化物,特别是氮化硼、硅灰石、滑石、高岭土、粘土、云母、氧化铝、氧化锆、二氧化钛及其混合物。优选的有机填料选自氟类聚合物、聚苯乙烯类聚合物、二乙烯基苯类聚合物、聚酰亚胺类聚合物、聚苯醚类聚合物、聚(三烯丙基异氰脲酸酯)类聚合物及其混合物。下文在本申请中进一步描述的有机和无机纤维不是本段中所理解的填料。
添加剂
此外,本发明的可聚合组合物可以包含至少一种添加剂,所述添加剂选自抗氧化剂、阻燃剂、热稳定剂、抗静电剂、UV吸收剂、颜料、润湿剂、消泡剂、着色剂、润滑剂、粘合促进剂、附加单体和相容剂。优选的附加单体选自苯乙烯、乙烯基甲苯、叔丁基苯乙烯、对甲基苯乙烯、邻苯二甲酸二烯丙酯、2,4-乙基甲基咪唑、聚苯醚、三烯丙基异氰脲酸酯、丁二烯、异戊二烯和1,2-丁二烯。优选的相容剂选自苯乙烯-丁二烯嵌段共聚物、苯乙烯-异戊二烯嵌段共聚物、1,2-聚丁二烯、1,4-聚丁二烯、马来酸改性聚丁二烯、丙烯酸改性聚丁二烯、环氧改性聚丁二烯及其混合物。
半成品的制备方法
在另一个实施方案中,本发明涉及一种方法,该方法包括以下步骤:
a)提供在本申请中如上所限定的可聚合组合物;和
b)在150℃和200℃之间的温度下固化可聚合组合物,从而获得半成品。
术语“提供可聚合组合物”是指产生如上所述的可聚合组合物的方法。合适的方法是本领域已知的。
方法步骤中的固化产生了“半成品”,即产生可以进一步加工或运输但仍然足够柔软和柔韧以进行加工(例如将其压入模具中)的材料。
在一个优选实施方案中,方法步骤b)持续进行直到所得聚合物无粘性。
在另一个优选实施方案中,方法步骤b)持续进行直到消耗掉在方法步骤b)开始时存在的自由异氰酸酯基团的2%至60%。
在又一个优选实施方案中,方法步骤b)持续进行直到可聚合组合物达到30,000至750,000mPas,优选50,000至750,000mPas,且最优选100,000至750,000mPas的粘度。粘度优选使用锥板粘度计(cone and plate viscosimeter)在23℃的温度和1/s的剪切速率下测定。
在一个特别优选实施方案中,方法步骤b)持续进行,直到通过板-板流变仪(plate-plate rheometer)根据ISO 6721-10:2015-09在23℃的温度和1/s的剪切速率下测定的模量G’达到5×103Pa。
如果所述可聚合组合物中存在惰性有机溶剂,则方法步骤b)优选持续进行直到蒸发至少90重量%的有机溶剂。该标准优选与一个或多个上文所限定的与聚合物网络状态有关的标准相结合。
在任何情况下优选的是在方法步骤b)结束时,仍然存在在方法步骤a)开始时存在的自由异氰酸酯基团的至少20%,优选至少30%,使得第二固化步骤是可行的。
方法步骤b)优选在150℃和200℃之间的温度下进行1至20分钟。第一固化步骤的温度和持续时间的组合取决于产物的几何形状以及待使用的可聚合组合物中存在的多异氰酸酯和(一种或多种)催化剂的类型。它可以简单通过应用上述方法步骤b)的优选终点之一的简单初步实验来测定。
方法步骤b)可以简单通过将温度降低到不超过60℃,优选不超过40℃的温度而停止。
在本发明的优选实施方案中,在开始方法步骤b)之前,用方法步骤a)中提供的可聚合组合物涂覆可聚合组合物纤维或金属片材。所述纤维可以是本领域中用于制备复合材料的任何无机或有机纤维。所述纤维可以具有一定的尺寸。所述金属片材优选为铜片材。
优选的无机纤维是玻璃纤维、玄武岩纤维、硼纤维、陶瓷纤维、晶须、二氧化硅纤维和金属增强纤维。优选的有机纤维是天然纤维、芳族聚酰胺纤维、碳纤维、碳纳米管、聚酯纤维、尼龙纤维和有机玻璃纤维。优选的天然纤维是亚麻纤维、大麻纤维、木纤维、纤维素纤维和剑麻纤维。
如果在开始方法步骤b)之前用所述可聚合组合物涂覆一个或多个纤维或一个或多个金属片材,则由方法步骤b)产生的半成品是所谓的“预浸料”。该术语是指预涂有可聚合组合物的纤维或多个纤维或金属片材,该可聚合组合物已经部分固化,使得所述纤维或多个纤维或金属片材可以被运输或加工。
本发明的方法产生了特别有利的半成品,因为通过三聚交联异氰酸酯基团仅在远高于室温的温度下进行,使得半成品可以在室温下储存数周而不丧失其被进一步加工的能力。
在又一个实施方案中,本发明涉及通过本发明的方法获得或可获得的半成品。
方法步骤a)和b)产生半成品,该半成品可以由客户出售、运输和进一步加工。在优选实施方案中,所述半成品是预浸料。
完全固化产品的制备方法
在另一个优选实施方案中,本发明的方法包括固化所述半成品的附加方法步骤c),由此获得成品。
方法步骤c)优选进行直到消耗掉在方法步骤b)开始时在可聚合组合物中原始存在的异氰酸酯基团的90%。
对于方法步骤c),优选温度在200℃和250℃之间。方法步骤c)的优选持续时间为1小时至8小时,更优选2小时至6小时。
优选方法步骤c)在方法步骤b)完成后1天至30天,更优选3天至14天开始。此外,优选进行方法步骤c)的位置与进行方法步骤b)的位置相距至少1km,更优选至少10km,即在第二固化步骤之前将半成品运输到不同的位置。
方法步骤c)得到完全固化的产物。
在又一个实施方案中,本发明涉及通过本发明的方法获得或可获得的成品,该方法包括如上所限定的方法步骤a)、b)和c)。
优选地,成品形成层压板、覆金属层压板或印制电路板,更优选地形成覆铜层压板或印制电路板的一部分。
成品是多异氰脲酸酯塑料,即它是交联基团主要是异氰脲酯基团的聚合物。与其它聚合物相比,该产品的特征在于优异的硬度和耐热性。此外,即使没有添加专用阻燃剂,它本质上也是防火的。
以下实施例仅意在说明本发明。它们不应以任何方式限制权利要求的范围。
实施例
当前25℃的普遍环境温度在本实验部分中被描述为RT。
通过FT-IR测定NCO含量:
在Perkin Elmer,Inc.的配备有ATR单元的Spectrum of FT-IR光谱仪上记录IR光谱。通过记录异氰酸酯基团的变化来监测残留NCO含量(2270cm-1处的谱带)。
通过DSC测定固化树脂的Tg值:
根据IPC-TM-650 2.4.25,通过差示扫描量热法(DSC)在TA DSC Q20上测定后固化后预浸料的玻璃化转变温度(Tg)。
通过DMA测定CCL的Tg值:
根据IPC-TM-650 2.4.24.4,使用动态力学分析来测定没有覆盖层的基底层压材料的玻璃化转变温度Tg。
通过DMA测定CCL的Td值:
根据IPC-TM-650 2.4.24.6,使用热重分析法测定没有覆盖层的基底层压材料的热分解温度Td以记录样品的质量比在50℃下测得的其质量小5.0%时的温度Td(5%)。
通过SPDR测定CCL的Dk和Df值:
根据IEC 61189-2-721,使用分裂柱介质谐振器(SPDR)在10G微波频率下来测定没有覆盖层的基底层压材料的介电常数(Dk)和耗散因子(Df)。
原材料:
Desmodur N 3600是具有23.0重量%NCO含量的六亚甲基二异氰酸酯(HDI)三聚体(NCO官能度>3),在23℃下粘度为约1200mPas(DIN EN ISO 3219/A.3),来自Covestro AG。
Desmodur N 3900是具有23.5重量%NCO含量的HDI三聚体(NCO官能度>3),在23℃下粘度为约730mPas(DIN EN ISO 3219/A.3),来自Covestro AG。
Desmodur eco N 7300是具有21.9重量%NCO含量的生物基五亚甲基二异氰酸酯(PDI)三聚体(NCO官能度>3),在23℃下粘度为约9500mPas(DIN EN ISO 3219/A.3),来自Covestro AG。
Desmodur Z4470是具有70重量%固体含量、11.9重量%NCO含量的在乙酸丁酯(BA)或溶剂石脑油(SN)中的异佛尔酮二异氰酸酯(IPDI)三聚体(NCO官能度>3),在23℃下粘度为约1500mPas(DIN EN ISO 3219/A.3),来自Covestro AG。
Desmodur IL是具有51重量%固体含量、8.0重量%NCO含量的在乙酸丁酯(BA)或乙酸乙酯(EA)中的甲苯二异氰酸酯(TDI)三聚体(NCO官能度>3),在23℃下粘度为700-2000mPas(DIN EN ISO 3219/A.3),来自Covestro AG。
Desmodur XP 2489是具有21.0重量%NCO含量的HDI异佛尔酮二异氰酸酯(IPDI)多异氰酸酯(NCO官能度>3),在23℃下的粘度为约22,500mPas(DIN EN ISO 3219/A.3),来自Covestro AG
催化剂:2-[2-(二甲基氨基)乙基-甲基氨基]乙醇购自TCI Co.Ltd.。
溶剂:纯度≥99.0%的乙酸丁酯购自Sinopharm Chemical Reagent Co.Ltd.。
二氧化硅粉末购自日本Denka Co.。
2116型E-玻璃纤维编织布购自CTM glass fiber Co.,Ltd.。
制备树脂组合物和预浸料的通用方法
1.将表1和表2中列出的成分加入到混合容器中;
2.在室温下使用SpeedMixer DAC 400FV以2500rpm将成分混合60-300秒。此时,该组合物已准备好使用。
3.将2116编织玻璃布浸渍到充分混合的组合物中,并控制以具有适当的厚度。
3.将经浸渍的玻璃布在180-200℃的烘箱中烘制2-15分钟,以除去溶剂并部分固化树脂组合物来制备预浸料。
通过FT-IR监测残留NCO含量。
通过使用FT-IR监测几天后的残留NCO含量来检查储存稳定性。
4.然后将预浸料在200-220℃下压制,并且优选地提供一些压力,例如5巴,以提供纤维复合组分。
通过FT-IR监测后固化后的残留NCO含量
通过DSC和TGA监测复合中的固化树脂的Tg和Td。
应用实施例:
为了制备CCL,将来自实施例1、实施例2和对比例2的树脂组合物分别与30重量%的二氧化硅粉末在乙酸丁酯中按一定比例混合,并且将胶溶液的固体含量控制为65%。将2116玻璃布浸渍到上述胶水溶液中,并控制以具有适当的厚度,然后在180-200℃的烘箱中放置2-15分钟以预浸预浸料。然后将6个预浸料片材堆叠在一起,其中两侧堆叠有铜箔,并在170-250℃的固化温度和25-50巴的固化压力下固化200-300分钟,以获得覆铜层压板。
通过DMA监测CCL的Tg
通过TGA监测CCL的Td
通过SPDR监测CCL的DK、Df
CCL的性能如表3中所示。
/>
/>
实施例1至7表明,本发明的树脂组合物提供了具有良好储存稳定性的可行的预浸料溶液。如果需要高耐热性作为附加性质,则与实施例7相比,实施例1至6表明,与其使用不对称三聚体(实施例7),不如使用具有异氰脲酸酯结构的多异氰酸酯(实施例1至6)。
对比例1(10%IPDI三聚体+90%HDI三聚体)和对比例4(20%IPDI三聚体+80%PDI三聚体)表明低含量的IPDI三聚体也导致低Tg。
对比例2表明(i)该体系的Tg太低而不能满足CCL应用要求,以及(ii)仅具有脂族多异氰酸酯的体系在第一固化步骤之后几乎已经完全固化,在第二固化步骤中,只有少量的NCO基团被进一步消耗,这将导致用于制备复合材料的较差的粘附性或层间强度。这个问题为如对比应用实施例1中所示。
对比例3表明,纯芳族三聚体将使体系对水分敏感,并将迅速成为高粘度体系,该体系不能容易地用于浸渍纤维。在储存过程中,自由异氰酸酯将很容易消耗掉,因此没剩下足够的残留NCO含量用于第二固化步骤的进一步压制。因此,该体系不适用于工业应用。
Claims (15)
1.一种可聚合组合物,其不含异氰酸酯反应性基团或异氰酸酯组分的异氰酸酯基团与异氰酸酯反应性基团的摩尔比为至少2.0:1.0,其包含
a)至少一种脂族多异氰酸酯;
b)至少一种脂环族多异氰酸酯;和
c)至少一种三聚催化剂;
其中基于所述可聚合组合物中存在的所有多异氰酸酯的总质量计,所述脂环族多异氰酸酯的浓度为25重量%-75重量%;并且
其中所述组合物中脲二酮形成催化剂的浓度不大于所述可聚合组合物中存在的脲二酮形成催化剂和三聚催化剂的总质量的10重量%。
2.根据权利要求1所述的可聚合组合物,还包含基于所有多异氰酸酯、所有三聚催化剂和所有溶剂的总和计的10重量%-50重量%的至少一种惰性溶剂。
3.根据权利要求1或2所述的可聚合组合物,其中所述至少一种脂族多异氰酸酯占所述可聚合组合物中存在的所有多异氰酸酯的总量的10重量%-80重量%。
4.根据权利要求1至3中任一项所述的可聚合组合物,其中所述至少一种脂族多异氰酸酯和/或所述至少一种脂环族多异氰酸酯是含有基于相应多异氰酸酯中存在的低聚结构的总和计的至少50mol%异氰脲酸酯结构的低聚多异氰酸酯,所述低聚结构选自脲二酮、异氰脲酯、脲基甲酸酯、缩二脲、亚氨基噁二嗪二酮和噁二嗪三酮。
5.根据权利要求1至5中任一项所述的可聚合组合物,其中使用根据式(I)的三聚催化剂或其加合物
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、支化的C5-烷基、非支化的C5烷基、支化的C6烷基、非支化的C6烷基、支化的C7烷基和非支化的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。
6.根据权利要求1至5中任一项所述的可聚合组合物,其还包含有机或无机填料。
7.一种方法,其包括以下步骤:
a)提供如权利要求1至6中任一项所限定的可聚合组合物;和
b)在150℃和200℃之间的温度下固化所述可聚合组合物,从而获得半成品。
8.根据权利要求7所述的方法,其中方法步骤b)持续进行直到所述可聚合组合物达到30,000-750,000mPas的粘度。
9.根据权利要求7或8所述的方法,其中方法步骤持续进行直到消耗掉在方法步骤b)开始时存在的自由异氰酸酯基团的2%至60%。
10.根据权利要求7-9中任一项所述的方法,还包括用方法步骤a)中提供的可聚合组合物涂覆至少一种有机或无机纤维的方法步骤al)。
11.根据权利要求7-10中任一项所述的方法,还包括固化所述半成品的方法步骤c),由此获得成品。
12.根据权利要求11所述的方法,其中方法步骤c)在方法步骤b)完成后1天至30天开始。
13.半成品,其通过权利要求7-10中任一项所述的方法获得或可获得。
14.成品,其通过权利要求11或12所述的方法获得或可获得。
15.覆铜层压板或印制电路板,其包括根据权利要求11或12所述的产品。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNPCT/CN2021/083529 | 2021-03-29 | ||
CN2021083529 | 2021-03-29 | ||
EP21171053.8 | 2021-04-28 | ||
EP21171053 | 2021-04-28 | ||
PCT/EP2022/058061 WO2022207532A1 (en) | 2021-03-29 | 2022-03-28 | Polyisocyanurate-prepregs and fiber composite components produced therefrom |
Publications (1)
Publication Number | Publication Date |
---|---|
CN117136205A true CN117136205A (zh) | 2023-11-28 |
Family
ID=80913126
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202280025110.6A Pending CN117136205A (zh) | 2021-03-29 | 2022-03-28 | 多异氰脲酸酯预浸料及由其生产的纤维复合材料组分 |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP4314102A1 (zh) |
JP (1) | JP2024514474A (zh) |
CN (1) | CN117136205A (zh) |
WO (1) | WO2022207532A1 (zh) |
Family Cites Families (52)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB809809A (en) | 1956-11-16 | 1959-03-04 | Ici Ltd | Polymeric isocyanates and their manufacture |
GB1200542A (en) | 1967-01-19 | 1970-07-29 | Takeda Chemical Industries Ltd | A method for producing isocyanate trimers |
DE1954093C3 (de) | 1968-11-15 | 1978-12-21 | Mobay Chemical Corp., Pittsburgh, Pa. (V.St.A.) | Verfahren zur Herstellung von polymeren organischen Isocyanaten |
GB1386399A (en) | 1971-07-16 | 1975-03-05 | Ici Ltd | Isocyanurate polymers |
GB1391066A (en) | 1971-07-16 | 1975-04-16 | Ici Ltd | Urethane oils |
DE2414413C3 (de) | 1974-03-26 | 1978-08-24 | Bayer Ag, 5090 Leverkusen | Verwendung von Lösungen von Polyisocyanaten mit Isocyanuratstruktur in Zweikomponenten-Polyurethan-Lacken |
DE2452532C3 (de) | 1974-11-06 | 1978-08-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyisocyanaten mit Isocyanurat-Struktur |
US4040992A (en) | 1975-07-29 | 1977-08-09 | Air Products And Chemicals, Inc. | Catalysis of organic isocyanate reactions |
DE2641380C2 (de) | 1976-09-15 | 1989-11-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyisocyanaten mit Isocyanuratstruktur |
DE2901479A1 (de) | 1979-01-16 | 1980-07-24 | Bayer Ag | Neue isocyanato-isocyanurate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als isocyanatkomponente in polyurethan-lacken |
CA1127644A (en) | 1980-01-28 | 1982-07-13 | Anupama Mishra | Isocyanurate products and polyurethanes therefrom |
DE3033860A1 (de) | 1980-09-09 | 1982-04-15 | Bayer Ag, 5090 Leverkusen | Neue isocyanato-isocyanurate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als isocyanatkomponente in polyurethanlacken |
DE3100263A1 (de) | 1981-01-08 | 1982-08-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung bei der herstellung von polyurethanen |
DE3100262A1 (de) | 1981-01-08 | 1982-08-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten, als katalysator-komponente fuer dieses verfahren geeignete loesungen, sowie die verwendung der verfahrensprodukte als isocyanat-komponente bei der herstellung von polyurethanen |
JPS58162581A (ja) | 1982-03-19 | 1983-09-27 | Nippon Polyurethan Kogyo Kk | ポリウレタン塗料用組成物 |
DE3227489A1 (de) | 1982-07-23 | 1984-01-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung als isocyanatkomponente zur herstellung von polyurethanen |
PT77070B (en) | 1982-07-29 | 1986-01-27 | Dsm Resins Bv | Oligomerisation of polyisocyanates |
AT375652B (de) | 1982-10-29 | 1984-08-27 | Valentina Alexandro Postnikova | Verfahren zur herstellung von arylaliphatischen polyisozyanuraten |
JPH0678418B2 (ja) | 1986-03-10 | 1994-10-05 | 大日本インキ化学工業株式会社 | 樹脂組成物 |
DE3700209A1 (de) | 1987-01-07 | 1988-07-21 | Bayer Ag | Verfahren zur herstellung von polyisocyanaten mit biuretstruktur |
DE3811350A1 (de) | 1988-04-02 | 1989-10-19 | Bayer Ag | Verfahren zur herstellung von isocyanuratpolyisocyanaten, die nach diesem verfahren erhaltenen verbindungen und ihre verwendung |
DE3814167A1 (de) | 1988-04-27 | 1989-11-09 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
CA1334848C (en) | 1988-08-05 | 1995-03-21 | William E. Slack | Process for the production of polyisocyanates which contain isocyanurate groups |
CA1334849C (en) | 1988-08-24 | 1995-03-21 | Bayer Corporation | Process for the production of polyisocyanates which contain isocyanurate groups |
DE3900053A1 (de) | 1989-01-03 | 1990-07-12 | Bayer Ag | Verfahren zur herstellung von uretdion- und isocyanuratgruppen aufweisenden polyisocyanaten, die nach diesem verfahren erhaeltlichen polyisocyanate und ihre verwendung in zweikomponenten-polyurethanlacken |
DE3902078A1 (de) | 1989-01-25 | 1990-07-26 | Bayer Ag | Verfahren zur herstellung von modifizierten, isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
DE3928503A1 (de) | 1989-08-29 | 1991-03-07 | Bayer Ag | Verfahren zur herstellung von loesungen von isocyanuratgruppen aufweisenden polyisocyanaten in lackloesungsmitteln und ihre verwendung |
DE4005762A1 (de) | 1990-02-23 | 1991-08-29 | Bayer Ag | Trimerisierungskatalysatoren, ein verfahren zu ihrer herstellung und ihre verwendung bei der herstellung von isocyanuratgruppen aufweisenden polyisocyanaten |
DE4405054A1 (de) | 1994-02-17 | 1995-08-24 | Basf Ag | Modifizierte (cyclo)aliphatische Polyisocyanatmischungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
DE4405055A1 (de) | 1994-02-17 | 1995-08-24 | Basf Ag | Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten und ihre Verwendung |
DE19611849A1 (de) | 1996-03-26 | 1997-10-02 | Bayer Ag | Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
GB9709166D0 (en) | 1997-05-06 | 1997-06-25 | Cytec Ind Inc | Preforms for moulding process and resins therefor |
DE19734048A1 (de) | 1997-08-06 | 1999-02-11 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten, damit hergestellte Polyisocyanate und deren Verwendung |
ZA9810038B (en) | 1997-11-04 | 2000-05-03 | Rhodia Chimie Sa | A catalyst and a method for the trimerization of isocyanates. |
ATE225777T1 (de) | 1998-06-02 | 2002-10-15 | Bayer Ag | Verfahren zur herstellung iminooxadiazindiongruppen enhaltender polyisocyanate |
DE10065176A1 (de) | 2000-12-23 | 2002-06-27 | Degussa | Katalysator und Verfahren zur Herstellung von niedrigviskosen und farbreduzierten isocyanuratgruppenhaltigen Polyisocyanaten |
CA2516089C (en) | 2003-02-28 | 2013-05-14 | Dow Global Technologies Inc. | Preparation of isocyanurate group containing polyisocyanate mixtures |
DE102004012571A1 (de) | 2004-03-12 | 2005-09-29 | Basf Ag | Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten und ihre Verwendung |
DE102010041247A1 (de) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Verfahren zur Herstellung von lagerstabilen Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung in Lösung |
US9399705B2 (en) | 2012-03-20 | 2016-07-26 | Bayer Intellectual Property Gmbh | Storage-stable polyurethane-prepregs and fibre composite components produced therefrom |
WO2013167404A1 (en) | 2012-05-08 | 2013-11-14 | Basf Se | Preparation of polyisocyanates having isocyanurate groups and their use |
US10167369B2 (en) * | 2014-08-29 | 2019-01-01 | Covestro Deutschland Ag | Lightfast polyurethane prepregs and fiber composite elements produced therefrom |
EP3286244B1 (en) | 2015-04-21 | 2023-11-01 | Covestro Intellectual Property GmbH & Co. KG | Polyisocyanurate polymers and process for the production of polyisocyanurate polymers |
US10597484B2 (en) | 2015-04-21 | 2020-03-24 | Covestro Deutschland Ag | Polyisocyanurate plastics having high thermal stability |
KR20170139022A (ko) | 2015-04-21 | 2017-12-18 | 코베스트로 도이칠란트 아게 | 단열성 조건 하에 제조된 폴리이소시아누레이트 중합체를 기재로 하는 고형물 |
KR20190006169A (ko) * | 2016-05-04 | 2019-01-17 | 코베스트로 도이칠란트 아게 | 복합 폴리이소시아누레이트 재료를 제조하는 방법 |
EP3538585A1 (de) | 2016-11-14 | 2019-09-18 | Covestro Deutschland AG | Kompositwerkstoffe basierend auf isocyanuratpolymeren mit dualer härtung |
WO2019197639A1 (de) * | 2018-04-13 | 2019-10-17 | Covestro Deutschland Ag | Addukte von aminkatalysatoren zur herstellung von isocyanuratpolymeren |
US11319402B2 (en) * | 2018-05-17 | 2022-05-03 | Covestro Intellectual Property Gmbh & Co. Kg | Method for producing a polyisocyanate polymer and a polyisocyanurate plastic |
WO2020152107A1 (de) | 2019-01-22 | 2020-07-30 | Covestro Intellectual Property Gmbh & Co. Kg | Kompositwerkstoffe basierend auf urethan- und isocyanuratpolymeren mit dualer härtung |
TW202206519A (zh) * | 2019-06-27 | 2022-02-16 | 日商旭化成股份有限公司 | 聚異氰酸酯組合物、薄膜形成用組合物、薄膜、薄膜積層體、接著性樹脂組合物及接著性樹脂硬化物、塗料用組合物及塗料硬化物 |
US11453739B2 (en) * | 2020-06-16 | 2022-09-27 | Covestro Llc | Use of thermally decomposable acid as inhibitor for preparing polyisocyanurate composites |
-
2022
- 2022-03-28 CN CN202280025110.6A patent/CN117136205A/zh active Pending
- 2022-03-28 EP EP22711573.0A patent/EP4314102A1/en active Pending
- 2022-03-28 WO PCT/EP2022/058061 patent/WO2022207532A1/en active Application Filing
- 2022-03-28 JP JP2023559762A patent/JP2024514474A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JP2024514474A (ja) | 2024-04-02 |
EP4314102A1 (en) | 2024-02-07 |
WO2022207532A1 (en) | 2022-10-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN107531874B (zh) | 聚异氰脲酸酯聚合物以及制备聚异氰脲酸酯聚合物的方法 | |
US11286332B2 (en) | Hydrophobically modified polyisocyanurate plastic and method for production thereof | |
US11613072B2 (en) | Dual-curing isocyanurate polymers | |
CN107438635B (zh) | 制造聚异氰脲酸酯塑料的方法 | |
EP3271411B1 (de) | Silangruppen enthaltende polyisocyanate auf basis von 1,5-diisocyanatopentan | |
CN107531862B (zh) | 在绝热条件下生产的基于聚异氰脲酸酯聚合物的固体 | |
KR102480612B1 (ko) | 복합 폴리이소시아누레이트 재료를 제조하는 방법 | |
CN107531876B (zh) | 具有高热稳定性的聚异氰脲酸酯塑料 | |
US11180599B2 (en) | Polyisocyanurate based polymers and fiber reinforced composites | |
EP3507321B1 (en) | Process for producing polyisocyanurate plastics by means of phosphine catalysis | |
JP2006510784A (ja) | 親水化ブロックトポリイソシアネート | |
US11597795B2 (en) | Amine catalysts for the manufacture of isocyanurate polymers | |
EP3286243B1 (en) | Process for producing polyisocvanurate plastics having functionalized surfaces | |
US11319402B2 (en) | Method for producing a polyisocyanate polymer and a polyisocyanurate plastic | |
CN113286836B (zh) | 基于双重固化的氨基甲酸酯和异氰脲酸酯聚合物的复合材料 | |
CN117136205A (zh) | 多异氰脲酸酯预浸料及由其生产的纤维复合材料组分 | |
CN111684031A (zh) | 具有高固体含量的芳族多异氰酸酯 | |
TW202309121A (zh) | 聚異氰尿酸酯預浸體及由其生產之纖維複合組件 | |
CN111479840A (zh) | 基于热潜催化剂的聚氨酯复合材料 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination |