CN116601199A - 稳定的环氧-异氰酸酯混合物和由其获得的含噁唑烷酮的聚合物 - Google Patents
稳定的环氧-异氰酸酯混合物和由其获得的含噁唑烷酮的聚合物 Download PDFInfo
- Publication number
- CN116601199A CN116601199A CN202180086174.2A CN202180086174A CN116601199A CN 116601199 A CN116601199 A CN 116601199A CN 202180086174 A CN202180086174 A CN 202180086174A CN 116601199 A CN116601199 A CN 116601199A
- Authority
- CN
- China
- Prior art keywords
- stabilizer
- acid
- diphenylmethane diisocyanate
- component
- composition according
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 74
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 3
- 229920000642 polymer Polymers 0.000 title description 3
- DLMVDBDHOIWEJZ-UHFFFAOYSA-N isocyanatooxyimino(oxo)methane Chemical compound O=C=NON=C=O DLMVDBDHOIWEJZ-UHFFFAOYSA-N 0.000 title description 2
- -1 silyl halides Chemical class 0.000 claims abstract description 41
- 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 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 30
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 30
- 239000003381 stabilizer Substances 0.000 claims abstract description 23
- 239000012948 isocyanate Substances 0.000 claims abstract description 22
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 19
- 150000002118 epoxides Chemical class 0.000 claims abstract description 18
- 239000006260 foam Substances 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000000654 additive Substances 0.000 claims abstract description 14
- 239000002168 alkylating agent Substances 0.000 claims abstract description 13
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 13
- 229920005989 resin Polymers 0.000 claims abstract description 13
- 239000011347 resin Substances 0.000 claims abstract description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000000996 additive effect Effects 0.000 claims abstract description 10
- 239000000853 adhesive Substances 0.000 claims abstract description 10
- 230000001070 adhesive effect Effects 0.000 claims abstract description 10
- 238000000576 coating method Methods 0.000 claims abstract description 10
- 239000012777 electrically insulating material Substances 0.000 claims abstract description 10
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims abstract description 10
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims abstract description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 8
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 7
- 230000002152 alkylating effect Effects 0.000 claims abstract description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 6
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract description 5
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 238000003860 storage Methods 0.000 abstract description 8
- 150000007522 mineralic acids Chemical class 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 description 24
- 229920005862 polyol Polymers 0.000 description 17
- 150000003077 polyols Chemical class 0.000 description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 229920000647 polyepoxide Polymers 0.000 description 14
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 239000004604 Blowing Agent Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 239000004593 Epoxy Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000002666 chemical blowing agent Substances 0.000 description 5
- 238000006735 epoxidation reaction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- XFSAZBKSWGOXRH-UHFFFAOYSA-N 2-(2-carbonochloridoyloxyethoxy)ethyl carbonochloridate Chemical compound ClC(=O)OCCOCCOC(Cl)=O XFSAZBKSWGOXRH-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004970 Chain extender Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 235000010338 boric acid Nutrition 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000012963 UV stabilizer Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical group C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000004872 foam stabilizing agent Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- VAUOPRZOGIRSMI-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CNC1=CC=CC=C1 VAUOPRZOGIRSMI-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 210000001170 unmyelinated nerve fiber Anatomy 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 1
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- LNSBXPNZJPZBQZ-UPHRSURJSA-N (e)-1-bromo-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C(Br)=C(/F)C(F)(F)F LNSBXPNZJPZBQZ-UPHRSURJSA-N 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- ZFDWWDZLRKHULH-UHFFFAOYSA-N 1,2-dimethyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C ZFDWWDZLRKHULH-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- FCQPNTOQFPJCMF-UHFFFAOYSA-N 1,3-bis[3-(dimethylamino)propyl]urea Chemical compound CN(C)CCCNC(=O)NCCCN(C)C FCQPNTOQFPJCMF-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- WFELVFKXQJYPSL-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(Cl)=O WFELVFKXQJYPSL-UHFFFAOYSA-N 0.000 description 1
- QFSNCROGCLRZHC-UHFFFAOYSA-N 2,3-dihydroxypropoxyboronic acid Chemical compound OCC(O)COB(O)O QFSNCROGCLRZHC-UHFFFAOYSA-N 0.000 description 1
- GTZXSBQCNBNWPK-UHFFFAOYSA-N 2-(2-chloro-2-oxoethoxy)acetyl chloride Chemical compound ClC(=O)COCC(Cl)=O GTZXSBQCNBNWPK-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- VSZURNDHYWQPTO-UHFFFAOYSA-N 2-bromo-1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=C(Br)C(F)(F)F VSZURNDHYWQPTO-UHFFFAOYSA-N 0.000 description 1
- JDTUPLBMGDDPJS-UHFFFAOYSA-N 2-methoxy-2-phenylethanol Chemical compound COC(CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-UHFFFAOYSA-N 0.000 description 1
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- PKZCRWFNSBIBEW-UHFFFAOYSA-N 2-n,2-n,2-trimethylpropane-1,2-diamine Chemical compound CN(C)C(C)(C)CN PKZCRWFNSBIBEW-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- XDVOLDOITVSJGL-UHFFFAOYSA-N 3,7-dihydroxy-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B(O)OB2OB(O)OB1O2 XDVOLDOITVSJGL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SPZXNEBFTNEDGH-UHFFFAOYSA-N 3-bromo-1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)Br SPZXNEBFTNEDGH-UHFFFAOYSA-N 0.000 description 1
- MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- AHIPJALLQVEEQF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=C1)=CC=C1N(CC1OC1)CC1CO1 AHIPJALLQVEEQF-UHFFFAOYSA-N 0.000 description 1
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 1
- BRKHZWFIIVVNTA-UHFFFAOYSA-N 4-cyclohexylmorpholine Chemical compound C1CCCCC1N1CCOCC1 BRKHZWFIIVVNTA-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 229920001342 Bakelite® Polymers 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000015842 Hesperis Nutrition 0.000 description 1
- 235000012633 Iberis amara Nutrition 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical compound O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 description 1
- IGGHSANJNRYSQB-UHFFFAOYSA-N OS([SiH3])(=O)=O Chemical class OS([SiH3])(=O)=O IGGHSANJNRYSQB-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- SVZSOVXXWFZQHH-UHFFFAOYSA-N [[hydroxymethyl(dimethyl)silyl]oxy-dimethylsilyl]methanol Chemical compound OC[Si](C)(C)O[Si](C)(C)CO SVZSOVXXWFZQHH-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000004637 bakelite Substances 0.000 description 1
- MLWPJXZKQOPTKZ-UHFFFAOYSA-N benzenesulfonyl benzenesulfonate Chemical compound C=1C=CC=CC=1S(=O)(=O)OS(=O)(=O)C1=CC=CC=C1 MLWPJXZKQOPTKZ-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- ZXOATMQSUNJNNG-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OCC2OC2)=CC=1C(=O)OCC1CO1 ZXOATMQSUNJNNG-UHFFFAOYSA-N 0.000 description 1
- NEPKLUNSRVEBIX-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OCC2OC2)C=CC=1C(=O)OCC1CO1 NEPKLUNSRVEBIX-UHFFFAOYSA-N 0.000 description 1
- KBWLNCUTNDKMPN-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) hexanedioate Chemical compound C1OC1COC(=O)CCCCC(=O)OCC1CO1 KBWLNCUTNDKMPN-UHFFFAOYSA-N 0.000 description 1
- 125000005619 boric acid group Chemical class 0.000 description 1
- OZCRKDNRAAKDAN-UHFFFAOYSA-N but-1-ene-1,4-diol Chemical compound O[CH][CH]CCO OZCRKDNRAAKDAN-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- QYJXDIUNDMRLAO-UHFFFAOYSA-N butyl 4-methylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=C(C)C=C1 QYJXDIUNDMRLAO-UHFFFAOYSA-N 0.000 description 1
- NIKBCKTWWPVAIC-UHFFFAOYSA-N butyl benzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=CC=C1 NIKBCKTWWPVAIC-UHFFFAOYSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- AIXMJTYHQHQJLU-UHFFFAOYSA-N chembl210858 Chemical compound O1C(CC(=O)OC)CC(C=2C=CC(O)=CC=2)=N1 AIXMJTYHQHQJLU-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000010431 corundum Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- WNIMXDGIDSPYDW-UHFFFAOYSA-N ethyl hexane-1-sulfonate Chemical compound CCCCCCS(=O)(=O)OCC WNIMXDGIDSPYDW-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000001034 iron oxide pigment Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- SWKKKZKIPZOMBG-UHFFFAOYSA-N methyl 3-nitrobenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 SWKKKZKIPZOMBG-UHFFFAOYSA-N 0.000 description 1
- ZAXQRWRRNPKBNK-UHFFFAOYSA-N methyl butane-1-sulfonate Chemical compound CCCCS(=O)(=O)OC ZAXQRWRRNPKBNK-UHFFFAOYSA-N 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- QUFIXTQDTDCCLJ-UHFFFAOYSA-N methyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC)=CC=CC2=C1 QUFIXTQDTDCCLJ-UHFFFAOYSA-N 0.000 description 1
- AFVPRVLDAPXRCX-UHFFFAOYSA-N methyl naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)OC)=CC=C21 AFVPRVLDAPXRCX-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- XFLSMWXCZBIXLV-UHFFFAOYSA-N n,n-dimethyl-2-(4-methylpiperazin-1-yl)ethanamine Chemical compound CN(C)CCN1CCN(C)CC1 XFLSMWXCZBIXLV-UHFFFAOYSA-N 0.000 description 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
- JKWQIKWWHDGDFT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine;trichloroborane Chemical compound ClB(Cl)Cl.CCCCCCCCN(C)C JKWQIKWWHDGDFT-UHFFFAOYSA-N 0.000 description 1
- WFBDWTZOYPUBQZ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]formamide Chemical compound CN(C)CCCNC=O WFBDWTZOYPUBQZ-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- WYZDCUGWXKHESN-UHFFFAOYSA-N n-benzyl-n-methyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(C)CC1=CC=CC=C1 WYZDCUGWXKHESN-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- UKQMUPLYHOXQQR-UHFFFAOYSA-N phenylmethanedithiol Chemical compound SC(S)C1=CC=CC=C1 UKQMUPLYHOXQQR-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound 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
- 239000012779 reinforcing material Substances 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KEBMUYGRNKVZOX-UHFFFAOYSA-N tetra(propan-2-yl)silane Chemical compound CC(C)[Si](C(C)C)(C(C)C)C(C)C KEBMUYGRNKVZOX-UHFFFAOYSA-N 0.000 description 1
- VCZQFJFZMMALHB-UHFFFAOYSA-N tetraethylsilane Chemical compound CC[Si](CC)(CC)CC VCZQFJFZMMALHB-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- INPZSKMAWFGEOP-UHFFFAOYSA-N tetrapropylsilane Chemical compound CCC[Si](CCC)(CCC)CCC INPZSKMAWFGEOP-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 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 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DWAWYEUJUWLESO-UHFFFAOYSA-N trichloromethylsilane Chemical compound [SiH3]C(Cl)(Cl)Cl DWAWYEUJUWLESO-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl 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
- C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/58—Epoxy resins
-
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
Abstract
本发明涉及一种包含储存稳定的树脂混合物的组合物，所述树脂混合物包含(a)多异氰酸酯，其包含至少一种二苯基甲烷二异氰酸酯的异构体和至少一种二苯基甲烷二异氰酸酯的高级同系物，(b)至少一种含有至少一个环氧基团的有机化合物，以及(c)至少一种选自烷基化剂的烷基化稳定剂(c1)和至少一种酸稳定剂(c2)，其选自羧酸、羧酸衍生物、无机酸、碳酸衍生物、硼酸、硼酸酯，至少一种选自溴化铵、氯化铵和氯化锂的盐，甲硅烷基卤化物、甲硅烷基醚及其两种或更多种的混合物。此外，本发明涉及一种通过添加催化剂组分以及如有必要，助剂材料和添加剂材料来制备模制品、电绝缘材料、涂料、粘合剂和泡沫的方法，所述催化剂组分包含用于异氰酸酯/环氧化物反应的催化剂。以及通过这种方法制备的模制品、电绝缘材料、涂料、粘合剂和泡沫。
Description
本发明涉及包含液体、储存稳定的树脂混合物的组合物，所述树脂混合物包含(a)多异氰酸酯，其包含至少一种二苯基甲烷二异氰酸酯的异构体，或者可替代地，由至少一种二苯基甲烷二异氰酸酯的异构体和至少一种二苯基甲烷二异氰酸酯的高级同系物组成的混合物，(b)至少一种含有至少一个环氧基团的有机化合物，以及(c)至少一种选自烷基化剂的烷基化稳定剂(c1)和至少一种酸稳定剂(c2)，其选自羧酸、羧酸衍生物、无机酸、碳酸衍生物、硼酸、硼酸酯，至少一种选自溴化铵、氯化铵和氯化锂的盐，甲硅烷基卤化物、甲硅烷基醚及其两种或更多种的混合物。此外，本发明涉及一种通过添加催化剂组分以及如有必要，助剂材料和添加剂材料制备模制品、电绝缘材料、涂料、粘合剂和泡沫的方法，所述催化剂组分包含用于异氰酸酯/环氧化物反应的催化剂。以及通过这种方法制备的模制品、电绝缘材料、涂料、粘合剂和泡沫。
用于制备聚氨酯(例如用于产生模制品)的异氰酸酯基树脂体系或用于制备作为聚氨酯泡沫的泡沫的异氰酸酯衍生泡沫早已为人所知，并且经常用于各种应用和技术中。这类化合物的一大优点是它们可通过简单地混合两种预先配制的组合物来制备：一种为包含多异氰酸酯的异氰酸酯组分，一种为包含异氰酸酯反应性化合物(通常为多元醇和催化剂)的异氰酸酯反应性组分。因此，基于这种异氰酸酯基体系的最终产品的制造商不需要详细的配方知识。
然而，使用此类材料时的一大挑战是温度稳定性。由于氨基甲酸酯基团在较高温度下的逆反应，此类聚氨酯在较高温度下的用途有限。为了解决这个问题，可将有机多异氰酸酯与环氧化物反应。多异氰酸酯与环氧化合物的原则性反应由文献已知。它在高温下产生噁唑烷酮。这类化合物以具有出色的温度稳定性而闻名。不幸的是，所应用的催化剂会激活环氧化物以及异氰酸酯。因此，为了在聚氨酯化学中使用两种组分，有必要一种组分包含多异氰酸酯和环氧化物，而第二种组分包含催化剂和任选地附加的化合物，例如多元醇或用于催化剂的溶剂。
数项专利涉及多异氰酸酯、环氧化合物和/或聚氨酯的混合物的制备、加工和使用。因此，US 4118373和DE 3600764记载了一种制备含有环氧化合物和多异氰酸酯的混合物的树脂体系的方法。此外，DE 3600764公开了技术人员已知的一般问题，即环氧化物和多异氰酸酯的混合物仅具有条件储存稳定性。随着时间的推移，这两种物质类别的液体混合物显示出粘度的强烈增加。从实用的观点来看这是不利的。
WO201280185和WO2012150201公开了一种两步反应，其中在第一步中，异氰酸酯和环氧化物之间的反应通过添加烷氧基化剂而停止在中间的高粘度状态。然后通过添加另外的催化剂和发泡剂在第二步中结束反应以形成阻燃泡沫。不期望使用如此高粘度的中间体。
为防止含有多异氰酸酯和环氧化合物的混合物的粘度增加，EP331996提出了一种方法，即允许从多异氰酸酯和环氧化合物制备液体、储存稳定的树脂混合物。EP0331996教导了抑制性烷基化剂的使用生成这两种物质的储存稳定的混合物。此外，EP0331996记载了从异氰酸酯化学中已知的反应阻滞剂或终止剂(例如酸和酰卤)不会导致此类混合物的永久稳定。在实施例1、2和9中，EP0331996清楚地显示出，单体亚甲基二苯基二异氰酸酯(MDI)或碳二亚胺改性的单体MDI与抑制性烷基化剂和环氧化合物结合的混合物会生成储存稳定的混合物。此外，EP331996在实施例10中公开了聚合MDI、聚环氧化物化合物和烷基化剂的混合物。然而，EP 0331996在该实施例中未公开关于此类混合物的储存稳定性的任何信息。当重复该实施例时，已经发现包含聚合MDI的混合物不能通过如EP331996中公开的方法有效地稳定。
由于聚合物MDI是不同聚氨酯树脂或泡沫体系的非常重要的结构单元，因此本发明的目的是找到一种方法来提供包含聚合物MDI和环氧树脂的液体、储存稳定的混合物。
出人意料地，该目的已通过液体、储存稳定的树脂混合物而解决，所述混合物包含(a)多异氰酸酯，其包含至少一种二苯基甲烷二异氰酸酯的异构体和至少一种二苯基甲烷二异氰酸酯的高级同系物，(b)至少一种含有至少一个环氧基团的有机化合物，以及(c)至少一种选自烷基化剂的烷基化稳定剂(c1)和至少一种酸稳定剂(c2)，其选自羧酸、羧酸衍生物、无机酸、碳酸衍生物、硼酸、硼酸酯，至少一种选自溴化铵、氯化铵和氯化锂的盐，甲硅烷基卤化物、甲硅烷基醚及其两种或更多种的混合物。
此外，本发明涉及一种通过添加催化剂组分以及如有必要，助剂材料和添加剂材料来制备模制品、电绝缘材料、涂料、粘合剂和泡沫的方法，所述催化剂组分包含用于异氰酸酯/环氧化物反应的催化剂。以及通过这种方法制备的模制品、电绝缘材料、涂料、粘合剂和泡沫。
根据本发明，本发明的储存稳定的树脂混合物在25℃下为液体。在这个意义上，液体意指根据DIN 53015测量的粘度低于1000Pa.s，优选低于500Pa.s并且最优选低于100Pa.s。
多异氰酸酯(a)在本发明的上下文中是指每分子包含两个或更多个反应性异氰酸酯基团的任何有机化合物，即，官能度为至少2。当使用的多异氰酸酯或两种或更多种多异氰酸酯的混合物不具有单一官能度时，所使用的组分a)的数加权平均官能度为至少2。多异氰酸酯a)的平均异氰酸酯官能度优选为至少2.2，并且更优选至少2.4。组分a)的平均官能度大于2，优选为2.2至4，优选为2.5至3.8，并且更优选为2.7至3.5。
考虑将本身已知的脂族、脂环族、芳脂族多官能异氰酸酯和优选地芳族多官能异氰酸酯用作多异氰酸酯a)。这种类型的多官能异氰酸酯本身是已知的或可通过本身已知的方法获得。更特别地，也可将多官能异氰酸酯作为混合物使用，在这种情况下，组分a)相应地包含各种多官能异氰酸酯。考虑用作多异氰酸酯的多官能异氰酸酯每分子具有两个(下文称为二异氰酸酯)或多于两个异氰酸酯基团。
优选地可使用芳族多异氰酸酯，例如甲苯2,4-二异氰酸酯和甲苯2,6-二异氰酸酯以及相应的异构体混合物。
对于本发明必不可少的是多异氰酸酯组分包含至少一种二苯基甲烷二异氰酸酯的异构体，例如2,2’-二苯基甲烷二异氰酸酯、2,4’-二苯基甲烷二异氰酸酯、4,4’-二苯基甲烷二异氰酸酯或二苯基甲烷二异氰酸酯的这些异构体中的2种或三种的混合物。除了二苯基甲烷二异氰酸酯的异构体之外，多异氰酸酯(a)包含至少一种二苯基甲烷二异氰酸酯的高级同系物，其包括至少3个芳族核的二苯基甲烷二异氰酸酯的多核缩合产物并且具有的异氰酸酯官能度为至少3，尤其是3或4或5。此类二苯基甲烷的异构体和同系物的混合物通常通过苯胺与甲醛的缩合和随后的光气化制备(粗二苯基甲烷二异氰酸酯)。通过对获得的粗MDI馏分进行蒸馏和再混合，可获得具有不同量的单个异构体和高级同系物的各种等级的MDI。这些包含MDI的高级同系物的混合物通常也称为聚合MDI或聚合物MDI。聚合MDI通常以其在25℃下的粘度表征。在根据本发明的优选实施方案中，共混物的粘度为50mPas至3.3500mPas，优选80mPas至3000mPas，更优选100mPas至2500，甚至更优选400至2300并且最优选500至800mPas。根据本发明，单独以及在混合物中的二苯甲烷的异构体和二苯甲烷的高级同系物通常称为MDI，包含高级同系物的混合物称为聚合物-MDI。此外，根据本发明，术语“聚合MDI”或“聚合物-MDI”是指包含MDI的高级同系物的MDI。
基于MDI的多官能异氰酸酯或两种或更多种多官能异氰酸酯的混合物是已知的并且例如由BASF以M20或/>M50的名称进行销售。
包含聚合MDI的多异氰酸酯的(平均)官能度可在2.2至4、更特别地2.5至3.8、更具体地2.7至3.5的范围内变化。这种具有不同官能度的基于MDI的多官能异氰酸酯的混合物尤其是在MDI制备中作为中间体获得的粗MDI。
根据本发明的多异氰酸酯组分(a)优选包含基于组分(a)的总重量计至少70重量％、更优选至少90重量％、尤其优选100重量％的MDI的高级同系物和一种或多种选自2,2’-MDI、2,4’-MDI、4,4’-MDI的多异氰酸酯。
含环氧化物的组分(b)包括任何所期望的脂族、脂环族、芳族和/或杂环化合物，其包括至少一个环氧基团。可用作组分b)的优选的环氧化物每分子具有1至4个、更优选2至4个、尤其优选2个环氧基团，并且优选环氧化物当量重量为90至500g/eq，更优选140至220g/eq。
合适的环氧化物为例如以下多元酚的多缩水甘油醚，例如邻苯二酚、间苯二酚、对苯二酚、4,4'-二羟基二苯基丙烷(双酚A)、4,4'-二羟基-3,3'-二甲基二苯基甲烷、4,4'-二羟基二苯基甲烷(双酚F)、4,4'-二羟基二苯基环己烷、4,4'-二羟基-3,3'-二甲基二苯基丙烷、4,4'-二羟基联苯、4,4'-二羟基二苯基砜(双酚S)、三(4-羟基苯基)甲烷、上述二酚的氯化和溴化产物、酚醛清漆(即来自一元或多元酚和/或甲酚与醛、特别是甲醛在当量比小于1:1的酸性催化剂的存在下的反应产物)、通过将2mol芳族羟基羧酸的钠盐用一摩尔二卤代烷烃或二卤代二烷基酯酯化获得的二酚(参见英国专利1 017 612)或通过酚和含有至少两个卤素原子的长链卤代石蜡缩合获得的多酚(参见GB专利1 024 288)。可进一步提及：基于芳族胺和环氧氯丙烷的聚环氧化物化合物，例如N-二(2,3-环氧丙基)苯胺、N,N'-二甲基-N,N'-二环氧丙基-4,4'-二氨基二苯基甲烷、N,N-二环氧丙基-4-氨基苯基缩水甘油醚(参见GB专利772 830和816 923)。
其他可能性是：多元芳族、脂族和脂环族羧酸的缩水甘油酯，例如邻苯二甲酸二缩水甘油酯、间苯二甲酸二缩水甘油酯、对苯二甲酸二缩水甘油酯、己二酸二缩水甘油酯和1mol芳族或脂环族二羧酸酐和1/2mol二醇或1/n mol的具有n个羟基的多元醇的反应产物的缩水甘油酯或六氢邻苯二甲酸二缩水甘油酯，其可任选地被甲基取代。
同样可使用多元醇的缩水甘油醚，多元醇例如1,4-丁二醇(DY-D,Huntsman)、1,4-丁烯二醇、丙三醇、三羟甲基丙烷(/>DY-T/CH,Huntsman)、季戊四醇和聚乙二醇。同样感兴趣的是异氰脲酸三缩水甘油酯、N,N'-二环氧丙氧基酰胺、多羟基硫醇的多缩水甘油基硫醚，例如二巯基甲基苯、二缩水甘油基三亚甲基三砜、基于乙内酰脲的多缩水甘油醚。
最后还可使用多不饱和化合物如植物油及其转化产物的环氧化产物。同样可以使用二烯烃和聚烯烃的环氧化产物，所述二烯烃和聚烯烃例如丁二烯、乙烯基环己烷、1,5-环辛二烯、1,5,9-环十二碳三烯、可进行环氧化的链增长加成聚合物和仍含有双键的互聚物，例如基于聚丁二烯、聚异戊二烯、丁二烯-苯乙烯互聚物、二乙烯基苯、二环戊二烯、不饱和聚酯，还有烯烃的环氧化产物，其可通过Diels-Alder加成随后通过用过氧化物化合物环氧化而转化为聚环氧化物获得，或含有两个通过桥接原子或桥接原子团连接的环戊烯或环己烯环的化合物的环氧化产物。
根据本发明，优选将以下聚环氧化物化合物或其混合物用作组分b)：
多元酚，特别是双酚A(GY250,Huntsman；/>0162,BakeliteAG；/>Resin 162,Hexion Specialty Chemicals GmbH；Eurepox 710,BrenntagGmbH；/>GY250,Hunstman,D.E.R.TM 332,The Dow Chemical Company；/>A18-00,LEUNA-Harze GmbH)或双酚F(4,4'-二羟基二苯基甲烷，/>GY281,Huntsman；/>F 16-01,LEUNA-Harze GmbH；/>F17-00,LEUNA-Harze GmbH)的多缩水甘油醚，基于芳族胺的聚环氧化合物，尤其是双(N-环氧丙基)苯胺、N,N'-二甲基-N,N'-二环氧丙基-4,4'-二氨基二苯基甲烷和N,N-二环氧丙基-4-氨基苯基缩水甘油醚；脂环族二羧酸的多缩水甘油酯，尤其是六氢邻苯二甲酸二缩水甘油酯和聚环氧化物，其来自nmol六氢邻苯二甲酸酐和1mol具有n个羟基的多元醇(n＝2-6的整数)、尤其是3mol六氢邻苯二甲酸酐和一摩尔1,1,1-三羟甲基丙烷的反应产物；3,4-环氧环己基甲基3,4-环氧环己烷羧酸酯。
双酚A和双酚F以及酚醛清漆的多缩水甘油醚是非常特别优选的，特别是双酚F的多缩水甘油醚。
液态聚环氧化物或低粘度双环氧化物，例如双(N-环氧丙基)苯胺或乙烯基环己烷双环氧化物，在特殊情况下可进一步降低已经液态的聚环氧化物的粘度或将固态聚环氧化物转化为液体混合物。
组分b)的用量优选对应异氰酸酯基团与环氧基团的当量比为1.0:10至600:1，更优选1.1:1至500:1，更优选1.2:1至150:1，并且尤其优选1.3:1至50:1。
稳定剂(c)包含至少一种烷基化稳定剂(c1)和至少一种酸稳定剂(c2)。
烷基化稳定剂(c1)选自烷基化剂。合适的烷基化剂(c1)基本上包括有机磺酸的任何烷基化酯，优选分子量为50至600g/mol、更优选80至400g/mol并且最优选110至250g/mol的那些酯。此类烷基化酯能够将烷基转移至其他分子中的合适反应的位点。优选的烷基化剂(c1)含有优选具有1至20个、更优选1至15个、甚至更优选1至10个并且特别优选1至4个碳原子的可转移烷基。例如，可使用有机磺酸烷基酯如脂族和芳族磺酸烷基酯。合适的脂族磺酸烷基酯包括丁磺酸甲酯、正全氟丁磺酸甲酯和己磺酸乙酯。合适的芳族磺酸烷基酯包括苯磺酸甲酯、乙酯或丁酯，对甲苯磺酸甲酯、乙酯或丁酯，1-萘磺酸甲酯，3-硝基苯磺酸甲酯，和2-萘磺酸甲酯。卤代烷，例如碘甲烷或碘乙烷，硫酸二甲酯，苯磺酰氯，苯磺酰酐，甲硅烷基磺酸酯，例如三氟甲磺酸三甲基甲硅烷基酯，苄基卤化物，例如苄基氯，烯丙基卤化物，例如烯丙基碘，酸酐，羧酸卤化物和碳酸酯以及甲酸酯卤化物，例如二乙二醇-双氯甲酸酯也可用作组分(c1)。在优选的实施方案中，烷基化稳定剂(c1)选自有机磺酸烷基酯、卤代烷、硫酸二甲酯及其混合物。尤其优选作为组分(c1)的是芳族磺酸酯，特别是对甲苯磺酸甲酯
烷基化稳定剂(c1)的用量优选为0.0005至5重量％，优选0.001至2重量％，更优选0.002至1重量％，并且最优选0.005至0.3重量％，基于组分(a)和(b)的总重量计。可将组分(c1)以纯形式或例如作为在组分(a)中的溶液添加至多组分体系中。
酸稳定剂(c2)选自羧酸、羧酸衍生物、无机酸、碳酸衍生物、硼酸、硼酸酯，至少一种选自溴化铵、氯化铵和氯化锂的盐，甲硅烷基卤化物、甲硅烷基醚及其两种或更多种的混合物。优选的羧酸包括单羧酸(例如甲酸、乙酸、丙酸)、羟基羧酸、氨基酸、酮酸(例如丙酮酸、乙酰乙酸)、芳族羧酸(例如苯甲酸、苯乙酸、氢化肉桂酰氯)、二羧酸(如丙二酸、苹果酸、琥珀酸、戊二酸、己二酸、马来酸、富马酸、邻苯二甲酸等)和聚羧酸。优选的羧酸衍生物为羧酸卤化物(例如乙酰氯、乙酰溴、丙酰氯、丙酰溴、丁酰氯、异丁酰氯、琥珀酰氯、戊酰氯、3,3,3-三氟丙酰氯、氯乙酰氯、甲氧基乙酰氯、苯乙酰氯、4-甲氧基苯甲酰氯、二甲基氨基甲酰氯、全氟丁酰氯、环丙烷碳酰氯、乙酰氧基乙酰氯、丙二酰氯、氧二亚乙基双(氯甲酸酯)和2,2’-氧化二乙酰氯(diglycolyl chloride)。优选的无机酸为盐酸、硝酸、磷酸、膦酸、硫酸、磺酸、硼酸、氢氟酸、氢溴酸、高氯酸和/或氢碘酸。优选的碳酸和碳酸衍生物为卤甲酸酯(例如碳酸甲酯、碳酸乙酯、碳酸亚丙酯、氯甲酸甲酯、溴甲酸甲酯、氯甲酸乙酯、溴甲酸乙酯、氯甲酸2-氟乙酯)和/或硫代碳酸酯。优选的硼酸为硼酸、偏硼酸、四硼酸、频哪醇硼酸(pinacoboric acid)、甘露醇合硼酸和甘油硼酸(glyceroboric acid)。优选的硼酸酯为硼酸三甲酯、硼酸三乙酯、硼酸频哪乙酯(pinacomoethyl borate)和硼酸甘油甲酯(glyceromethyl borate)。优选的甲硅烷基卤化物为四氯硅烷、二氯二甲基硅烷和三氯甲基硅烷。优选的甲硅烷基醚为四甲基硅烷、四乙基硅烷、四丙基硅烷和四异丙基硅烷。在特别优选的实施方案中，酸稳定剂(c2)选自磷酸和羧酸卤化物如氧二亚乙基双(氯甲酸酯)，特别优选氧二亚乙基双(氯甲酸酯)作为酸稳定剂(c2)。
酸稳定剂(c2)的用量优选为0.001至1重量％，优选0.005至0.3重量％，基于组分(a)和(b)的总重量计。可将组分(c2)以纯形式或例如作为在组分(b)中的溶液或作为在相应溶剂例如水或乙二醇中的溶液加入至多组分体系中。
液体、储存稳定的树脂混合物可进一步包含助剂材料和添加剂材料(d)。或者，助剂材料和添加剂材料(d)，如果使用的话，可添加至催化剂组分中或可单独添加，例如在单独的流中。在其他替代方案中，可将助剂材料和添加剂材料(d)添加至两者中，即所述液体储存稳定的树脂混合物以及催化剂组分。优选地，不将包含异氰酸酯反应性基团的化合物添加至液体储存稳定的树脂混合物中。
所用的添加剂材料d)可为，例如，聚醚醇(poetherol)、聚酯醇、聚醚酯醇(polyetheresterol)多胺、聚醚胺、发泡剂(化学和/或物理发泡剂)、交联剂、扩链剂、催化剂、填料、表面活性物质如乳化剂、泡沫稳定剂和泡孔调节剂、阻燃剂、脱模剂，以及已知的UV稳定剂和水解抑制剂。
多元醇包括具有至少2个、更特别地2至8个并且优选地2至3个醇羟基和分子量为62至8000g/mol的化合物。这种化合物本身作为聚氨酯的合成组分是已知的并且包括低分子质量扩链剂和数均分子量大于200g/mol的多元醇。扩链剂的实例为简单的多元醇，例如乙二醇、六-1,6-二醇、丙三醇或三羟甲基丙烷；多元醇的实例为含有二甲基硅氧烷单元的多元醇，例如双(二甲基羟甲基甲硅烷基)醚；含有酯基团的多羟基化合物，例如蓖麻油，或多羟基聚酯，其可通过过量的刚刚例举的类型的简单多元醇与优选二元羧酸和/或其氢化物(例如，己二酸、邻苯二甲酸或邻苯二甲酸酐)的缩聚获得；可通过将环氧烷烃如环氧丙烷和/或环氧乙烷加成至合适的起始分子如水、例如刚刚所述的简单醇、或具有至少两个氨基NH键的胺上获得的多羟基聚醚；或聚碳酸酯多元醇，其可例如由多元醇和碳酸酯或光气获得。
可使用的多胺为具有至少两个异氰酸酯反应性氢原子的化合物，其中至少一个属于伯氨基或仲氨基。它们包含聚醚胺和分子量小于500g/mol的化合物。聚醚胺从聚氨酯化学中已知并且可通过聚醚多元醇的末端胺化获得。它们优选具有500至8000g/mol的分子量。优选使用的具有两个氨基且分子量小于500g/mol的化合物更优选具有58至300g/mol且更特别地100至200g/mol的分子量。这些化合物的异氰酸酯反应性基团优选为两个伯氨基。在一个特别优选的实施方案中，伯氨基与芳族碳原子键合，优选与芳族6元环键合，更特别地在间位或对位。
优选使用小于20重量％、更优选小于10重量％的多元醇和/或多胺，并且更特别地无多元醇和/或多胺。在使用多元醇和/或多胺的情况下，优选以以下量进行：使得多异氰酸酯(a)中的异氰酸酯基团与组分(d)的异氰酸酯反应性化合物的比值大于1.5:1，优选大于5:1且更特别地大于10:1。
用于制备本发明泡沫的发泡剂包括化学发泡剂，例如水、甲酸及其混合物。除了甲酸和水之外，合适的化学发泡剂为二乙氧膦酰硫胆碱氧化物(phospholine oxide)。这些试剂与异氰酸酯基团反应形成二氧化碳并且，在甲酸的情况下，形成二氧化碳和一氧化碳。由于这些发泡剂通过与异氰酸酯基团的化学反应释放气体，因此将它们称为化学发泡剂。也可使用物理发泡剂，例如低沸点烃。特别合适的是对多异氰酸酯a)呈惰性且在大气压力下沸点低于100℃、优选低于50℃的液体，以便它们在放热加聚反应的影响下蒸发。优选使用的此类液体的实例为烷烃，例如庚烷、己烷、正戊烷和异戊烷，优选正戊烷和异戊烷、正丁烷和异丁烷和丙烷的技术混合物，环烷烃，例如环戊烷和/或环己烷，醚，例如呋喃、二甲醚和二乙醚，酮，例如丙酮和甲基乙基酮，羧酸的烷基酯，例如甲酸甲酯、草酸二甲酯和乙酸乙酯，并且卤代烃选自但不限于顺式或反式-1,3,3,3-四氟丙-1-烯、1,1,1-三氟-2-氯丙-1-烯、1-氯-3,3,3-三氟丙-1-烯、1-氯-2,3,3,3-四氟丙-1-烯(顺式或反式)，1,1,1,2,3-五氟丙-1-烯(顺式或反式)，1,1,1,4,4,4-六氟丁-2-烯、1-溴五氟丙-1-烯、2-溴五氟丙-1-烯、3-溴五氟丙-1-烯、1,1,2,3,3,4,4-七氟-1-丁烯、3,3,4,4,5,5,5-七氟-1-戊烯、1-溴-2,3,3,3-四氟丙-1-烯、2-溴-1,3,3,3-四氟丙-1-烯、3-溴-1,1,3,3-四氟丙-1-烯、2-溴-3,3,3-三氟丙-1-烯、(E)-1-溴-3,3,3-三氟丙-1-烯、3,3,3-三氟-2-(三氟甲基)丙-1-烯、1-氯-3,3,3-三氟丙-1-烯、2-氯-3,3,3-三氟丙-1-烯、1,1,1-三氟-2-丁烯及其混合物。也可使用这些低沸点液体与另一种和/或与其他取代或未取代烃的混合物。物理发泡剂优选可溶于组分(b)。
优选用作化学发泡剂的为水、甲酸/水混合物或甲酸，并且特别优选的化学发泡剂为甲酸-水混合物或甲酸。优选用作物理发泡剂的为戊烷异构体或戊烷异构体的混合物。在一个特别优选的实施方案中，使用小于5重量％、优选小于2重量％、更优选小于0.5重量％并且更特别地小于0.1重量％的发泡剂，在每种情况下基于组分(a)至(d)的总重量计。
任选伴随使用的其它助剂和添加剂(d)例如为填料，例如细磨的石英、白垩、白云石(Microdol)、氧化铝、碳化硅、石墨或刚玉；颜料，例如二氧化钛、氧化铁或有机颜料如酞菁颜料；增塑剂，例如邻苯二甲酸二辛酯、磷酸三丁酯或磷酸三苯酯；可结合的相容剂如甲基丙烯酸、β-羟丙基酯、马来酸酯和富马酸酯；增强阻燃性的物质，如红磷或氧化镁；可溶性染料或增强材料，例如玻璃纤维或玻璃织物。同样合适的为C纤维和C纤维织物和其他有机聚合物纤维，例如芳族聚酰胺纤维或LC聚合物纤维(LC＝“液晶”)。还考虑作为填料的是金属填料，例如铝、铜、铁和/或钢。金属填料更特别地以颗粒形式和/或粉末形式使用。
此外，助剂和添加剂(d)还可包括已知的聚醚硅氧烷类型的泡沫稳定剂、脱模剂，例如聚酰胺蜡和/或硬脂酸衍生物和/或天然蜡，例如巴西棕榈蜡，以及已知的UV稳定剂和水解抑制剂。
用于催化剂组分的催化剂对含有至少一个环氧基团的化合物(b)与多异氰酸酯(a)的反应具有明显的催化作用。合适的催化剂的实例为如也已知用于制备聚氨酯的常规的胺催化剂。实例包括脒，例如2,3-二甲基-3,4,5,6-四氢嘧啶，叔胺，例如三乙胺、三丁胺、三亚乙基二胺、二甲基环己胺、二甲基辛胺、N,N-二甲基苄胺、N-甲基吗啉、N-乙基吗啉、N-环己基吗啉、N,N,N',N'-四甲基乙二胺、N,N,N',N'-四甲基丁二胺、N,N,N',N'-四甲基己二胺、五甲基二亚乙基三胺、四甲基二氨基乙醚、双(N,N-二甲基氨基乙基)醚、双(二甲基氨基丙基)脲、二甲基哌嗪、1,2-二甲基咪唑、1-氮杂双环(3,3,0)辛烷和优选地1,4-二氮杂双环(2,2,2)辛烷。同样合适的是例如五甲基二亚乙基三胺、N-甲基-N'-二甲基氨基乙基哌嗪、N,N-二乙基乙醇胺以及硅吗啉(silamorpholine)、三氯化硼/叔胺加合物以及N-[3-(二甲基氨基)丙基]甲酰胺。其他催化剂优选地包含三氯化硼/叔胺加合物、N,N-二甲基苄胺和/或N,N-甲基二苄胺和/或三氯(N,N-二甲基辛胺)硼。
此外，这些催化剂可包括可结合的胺催化剂。这些包括至少一个、优选1至8个并且更优选1至2个异氰酸酯反应性基团，例如伯氨基、仲氨基、羟基或脲基。本文酰胺和氨基之间的区别在于，为了本发明的目的，伯酰胺和仲酰胺不分别称为伯氨基和仲氨基。可结合的胺催化剂优选地包括伯氨基、仲氨基和/或羟基。根据本发明，可结合的胺催化剂优选地包括一个或多个叔氨基以及异氰酸酯反应性基团。优选地，可结合的催化剂的至少一个叔氨基带有至少两个脂族烃基部分，优选地每个部分具有1至10个碳原子，更优选地每个部分具有1至6个碳原子。特别优选叔氨基带有两个部分，各个部分独立地选自甲基、乙基和任何其他有机部分。
催化剂优选以0.001至8重量％、更优选0.6至6重量％、进一步优选1.5至5重量％且尤其是2.1至5重量％的浓度以催化剂或催化剂组合使用，基于组分(a)和(b)的总重量计。
为了获得根据本发明的液体、稳定的组合物，将起始材料(a)、(b)和(c)以及任何任选的助剂和添加剂(d)或其一部分同时或相继混合在一起。可将所有组分在20℃至150℃、优选60℃至130℃的温度范围内组合并加热。或者，可制备包含至少组分(b)和(c)的初始混合物，然后加热，随后添加其余组分。
将催化剂和任选地任何其他助剂和添加剂添加至中间产物用于进一步加工，任选地在它们已经溶解在合适的溶剂中之后。如果将树脂作为溶液进行后处理，则可使用惰性溶剂，例如丙酮、乙酸丁酯、甲乙酮、N-甲基吡咯烷酮或其混合物，或所谓的反应性稀释剂。用作反应性稀释剂的物质可为在(a)下例举的在室温下为液体的多异氰酸酯或在(a)下例举的在室温下也为液体的聚环氧化物。
在制备模制品、电绝缘材料、涂料、粘合剂和泡沫的方法中，通过加入包含用于异氰酸酯/环氧化物反应的催化剂的催化剂组分以及(如有必要)助剂材料和添加剂材料(d)。添加助剂材料和添加剂材料(d)时
可由如权利要求10所述的方法获得的模制品、电绝缘材料、涂料、粘合剂和泡沫。
混合物的固化发生在添加催化剂之后，优选在20℃至150℃下。为了获得最佳性能，通常建议在50℃至250℃、优选200℃至230℃的温度下对所得塑料进行后固化。
根据本发明的方法也可用于制备浸渍物质、用于电绝缘或用于玻璃纤维增强层压板。根据本发明的方法适用于通过铸造方法制备电气部件，包括制备例如印刷电路、电子钟、袖珍计算器、电子照相机、计算机、微型计算机和数字数据存储器。
通过根据本发明的方法获得的产物的耐热性、低介电损耗、耐湿性和耐磨性以及在模具中的加工性能是优异的。根据本发明的方法还适用于制备电动机和发电机中绝缘等级H和C(JEC 85/出版物84)的绝缘材料，以及制备用于飞机、火箭或其他承受严重应力的设备的结构材料。还可制备用于制备管道、容器或运动器材的绝缘体、变压器、电容器和层压板。如果将混合物与合适的发泡剂结合加工，则也可将它们用于制备泡沫。
以下实施例部分将举例说明本发明：
起始材料：
ISO 1 来自BASF的Lupranat M 20S，聚合物-MDI，NCO含量为31.5重量％，25℃下的粘度为210mPas
ISO 2 来自BASF的Lupranat MI，2,4-MDI和4,4’-MDI的混合物，NCO含量为33.5重量％，25℃下的粘度为12mPas
ISO 3 来自BASF的Lupranat MP 102，一种基于4,4’-MDI和聚醚醇的预聚物，NCO含量为22.9重量％，25℃下的粘度为650mPas
环氧树脂 来自Huntsman的Araldite GY 250，双酚-A-环氧氯丙烷环氧树脂，环氧当量重量为185g/eq，粘度为10-12Pas
终止剂1 对甲苯磺酸甲酯
终止剂2 二乙二醇双氯甲酸酯(oxydiethylenbis(chlorformate))
终止剂3 磷酸，85％水溶液
根据下表将所述组分在室温下混合并填充至几个气密密封容器中。混合和填充后，立即在23℃下测定粘度，并将剩余的密封容器在相应的时间段内储存在50℃下。在一定的储存期后，取出相应的容器并在23℃下测定粘度。
从实施例V6和V7可以看出，单独使用烷基化剂或酸或酰氯或氯甲酸酯都不会导致聚合MDI和环氧树脂的混合物稳定。出人意料地，烷基化剂与相应的酸或酰氯或氯甲酸酯的组合显示出混合物的明显稳定性。B1和B2中的混合物的粘度在短时间后稳定并且显示出粘度未显著增加。
Claims (11)
1.包含液体、储存稳定的树脂混合物的组合物，所述树脂混合物包含
(a)多异氰酸酯，其包含至少一种二苯基甲烷二异氰酸酯的异构体和至少一种二苯基甲烷二异氰酸酯的高级同系物，
(b)至少一种含有至少一个环氧基团的有机化合物，以及
(c)至少一种选自烷基化剂的烷基化稳定剂(c1)，和至少一种酸稳定剂(c2)，其选自羧酸、羧酸衍生物、无机酸、碳酸衍生物、硼酸、硼酸酯，至少一种选自溴化铵、氯化铵和氯化锂的盐，甲硅烷基卤化物、甲硅烷基醚及其两种或更多种的混合物。
2.根据权利要求1所述的组合物，其特征在于多异氰酸酯(a)由至少一种二苯基甲烷二异氰酸酯的异构体和至少一种二苯基甲烷二异氰酸酯的高级同系物组成。
3.根据权利要求1或2中任一项所述的组合物，其中组分(b)每分子含有2至4个环氧基团并且具有90至500g/eq的环氧化物当量重量。
4.根据权利要求1至3中任一项所述的组合物，其中稳定剂(c1)的烷基化剂含有具有1至4个碳原子的可转移烷基。
5.根据权利要求1至4中任一项所述的组合物，其中稳定剂(c1)选自有机磺酸烷基酯、卤代烷和硫酸二甲酯。
6.根据权利要求1至5中任一项所述的组合物，其中稳定剂(c2)选自磷酸和羧酸卤化物。
7.根据权利要求1至6中任一项所述的组合物，其中稳定剂(c1)以0.001至2重量％的量使用，基于组分(a)和(b)的总重量计。
8.根据权利要求1至7中任一项所述的组合物，其中稳定剂(c2)以0.001至1重量％的量使用，基于组分(a)和(b)的总重量计。
9.根据权利要求1至8中任一项所述的组合物，其中组分(b)以对应于组分(a)的异氰酸酯基团与组分(b)的环氧基团的当量比为1.0:10至500:1的量使用。
10.一种制备模制品、电绝缘材料、涂层、粘合剂和泡沫的方法，其通过将催化剂组分以及如有必要，助剂材料和添加剂材料(d)添加至如权利要求1至9中任一项所述的组合物中，所述催化剂组分包含用于异氰酸酯/环氧化物反应的催化剂。
11.可由如权利要求10所述的方法获得的模制品、电绝缘材料、涂料、粘合剂和泡沫。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20215903 | 2020-12-21 | ||
| EP20215903.4 | 2020-12-21 | ||
| PCT/EP2021/085872 WO2022136048A1 (en) | 2020-12-21 | 2021-12-15 | Stabilized epoxy-isocyanate mixtures and oxazolidinone containing polymers obtained therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116601199A true CN116601199A (zh) | 2023-08-15 |
Family
ID=73856071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202180086174.2A Pending CN116601199A (zh) | 2020-12-21 | 2021-12-15 | 稳定的环氧-异氰酸酯混合物和由其获得的含噁唑烷酮的聚合物 |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP4263646A1 (zh) |
| CN (1) | CN116601199A (zh) |
| WO (1) | WO2022136048A1 (zh) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1011618B (de) | 1954-12-06 | 1957-07-04 | Bayer Ag | Verfahren zur Herstellung basischer Diepoxydharze |
| GB816923A (en) | 1954-12-06 | 1959-07-22 | Bayer Ag | Process for the production of basic n,n-diepoxides |
| DE1222076C2 (de) | 1962-02-03 | 1976-01-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von diepoxiden |
| CH448513A (de) | 1963-11-14 | 1967-12-15 | Bayer Ag | Verfahren zur Herstellung von geformten Gebilden auf Basis von Epoxydharzen |
| US4118373A (en) | 1977-05-04 | 1978-10-03 | The Dow Chemical Company | Preparation of urethane elastomers from epoxy resin, polyols and polyisocyanates using a catalyst composition of an organometal salt with either nitrogen or phosphorus compounds |
| DE3600764A1 (de) | 1986-01-14 | 1987-07-16 | Bayer Ag | Waermehaertbare reaktionsharzgemische und ein verfahren zur herstellung von formkoerpern unter verwendung dieser gemische |
| DE3807660A1 (de) | 1988-03-09 | 1989-09-21 | Bayer Ag | Lagerstabile reaktionsharzmischung, herstellung und verwendung |
| EP2651997B1 (de) | 2010-12-15 | 2015-08-12 | Bayer Intellectual Property GmbH | Hochtemperaturbeständige schaumstoffe |
| CN103619927A (zh) | 2011-05-02 | 2014-03-05 | 拜耳知识产权有限责任公司 | 具有低导热性的耐高温泡沫材料 |
| EP3604370A1 (en) * | 2018-08-03 | 2020-02-05 | Covestro Deutschland AG | Catalysts for the synthesis of oxazolidinones |
-
2021
- 2021-12-15 EP EP21824601.5A patent/EP4263646A1/en active Pending
- 2021-12-15 CN CN202180086174.2A patent/CN116601199A/zh active Pending
- 2021-12-15 WO PCT/EP2021/085872 patent/WO2022136048A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| EP4263646A1 (en) | 2023-10-25 |
| WO2022136048A1 (en) | 2022-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1257739A (en) | Thermosetting reactive resin mixtures and a process for the production of moldings using these mixtures | |
| EP3170849B1 (en) | Nitrogen-containing heterocyclic epoxy curing agents, compositions and methods | |
| JP2597121B2 (ja) | 成形品製造のための二段階法 | |
| US9481776B2 (en) | Foams of high thermal stability | |
| US5021536A (en) | Storage stable resin reaction mixtures, and the preparation and use thereof | |
| JP2015504110A (ja) | ポリイソシアネート組成物を含む硬化性組成物 | |
| KR20120017023A (ko) | 폴리이소시아네이트 조성물 | |
| US20150065611A1 (en) | Curable Polyisocyanate Composition Comprising an Epoxy | |
| US20140093721A1 (en) | High-temperature-resistant foams having low thermal conductivity | |
| CA2028678A1 (en) | High temperature resistant foams | |
| KR102611262B1 (ko) | 옥사졸리디논 기를 포함하는 복합물의 제조 방법 | |
| CN107250229B (zh) | 具有高阻燃性的基于异氰酸酯的耐温泡沫 | |
| US10822519B2 (en) | Method for producing compact polyurethanes with improved hydrolytic stability | |
| EP3504258B1 (en) | Polyester-epoxide polymer compositions | |
| EP3601406B1 (en) | Polyether-epoxide polymer compositions | |
| US20140256909A1 (en) | Curable compositions | |
| US5266662A (en) | Thermosetting reaction mixtures, process for their production and the use thereof for production of moldings and molding material | |
| CN116601199A (zh) | 稳定的环氧-异氰酸酯混合物和由其获得的含噁唑烷酮的聚合物 | |
| EP3409707A1 (en) | Method for producing functionalized polyesters | |
| WO2020126544A1 (en) | Method for producing functionalized polyesters | |
| CA3109888A1 (en) | Fast curing epoxy system for producing rigid foam and use of the foam in composites or as insulation material | |
| JPH0148928B2 (zh) | ||
| CN117677646A (zh) | 具有低脆性和有所改善的附着性的异氰酸酯-环氧树脂混合泡沫材料 | |
| KR20230061880A (ko) | 우레탄계 강인화제를 포함하는 에폭시 수지 조성물 및 이의 제조방법 | |
| JPS6253527B2 (zh) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |