CN103649042B - 用于环氧树脂的低排放固化剂 - Google Patents
用于环氧树脂的低排放固化剂 Download PDFInfo
- Publication number
- CN103649042B CN103649042B CN201280034517.1A CN201280034517A CN103649042B CN 103649042 B CN103649042 B CN 103649042B CN 201280034517 A CN201280034517 A CN 201280034517A CN 103649042 B CN103649042 B CN 103649042B
- Authority
- CN
- China
- Prior art keywords
- epoxy resin
- amine
- polyamines
- composition
- amino
- 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.)
- Active
Links
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 106
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 102
- 239000004848 polyfunctional curative Substances 0.000 title description 2
- 150000001412 amines Chemical class 0.000 claims abstract description 87
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 72
- 238000000576 coating method Methods 0.000 claims abstract description 31
- 239000011248 coating agent Substances 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims description 82
- -1 cardanol amine Chemical class 0.000 claims description 63
- 229920000768 polyamine Polymers 0.000 claims description 56
- 150000002118 epoxides Chemical group 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- 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 claims description 22
- 239000007788 liquid Substances 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000007711 solidification Methods 0.000 claims description 14
- 230000008023 solidification Effects 0.000 claims description 14
- 150000004985 diamines Chemical class 0.000 claims description 13
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 9
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 8
- 239000011342 resin composition Substances 0.000 claims description 8
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 8
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 claims description 7
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 claims description 7
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 7
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 claims description 7
- 239000004952 Polyamide Substances 0.000 claims description 7
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 229920002647 polyamide Polymers 0.000 claims description 7
- 229930185605 Bisphenol Natural products 0.000 claims description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 6
- 239000004698 Polyethylene Substances 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 claims description 5
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 5
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 5
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 4
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 claims description 3
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 claims description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 3
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 2
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 claims description 2
- 241000276489 Merlangius merlangus Species 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 10
- 238000007712 rapid solidification Methods 0.000 abstract description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract description 5
- 235000019445 benzyl alcohol Nutrition 0.000 abstract description 5
- 229960004217 benzyl alcohol Drugs 0.000 abstract description 5
- 238000010790 dilution Methods 0.000 abstract description 3
- 239000012895 dilution Substances 0.000 abstract description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 27
- 239000000463 material Substances 0.000 description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000003973 paint Substances 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229940106691 bisphenol a Drugs 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000004417 polycarbonate Substances 0.000 description 8
- 229920000515 polycarbonate Polymers 0.000 description 8
- 238000005932 reductive alkylation reaction Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 206010009866 Cold sweat Diseases 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 150000003014 phosphoric acid esters Chemical class 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000037452 priming Effects 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000003566 sealing material Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000005352 clarification Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000008431 aliphatic amides Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 229920006272 aromatic hydrocarbon resin Polymers 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000005574 benzylation reaction Methods 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000004359 castor oil Chemical class 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000004567 concrete Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000007278 cyanoethylation reaction Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000002397 field ionisation mass spectrometry Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Chemical class 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 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 239000010440 gypsum Substances 0.000 description 2
- 229910052602 gypsum Inorganic materials 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012939 laminating adhesive Substances 0.000 description 2
- 238000000004 low energy electron diffraction Methods 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 229920000909 polytetrahydrofuran Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000013535 sea water Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 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
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 1
- OWICEWMBIBPFAH-UHFFFAOYSA-N (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1)(=O)OC1=CC=CC=C1 OWICEWMBIBPFAH-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- ABFQGXBZQWZNKI-UHFFFAOYSA-N 1,1-dimethoxyethanol Chemical compound COC(C)(O)OC ABFQGXBZQWZNKI-UHFFFAOYSA-N 0.000 description 1
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 description 1
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- RVPAFPCXAYNVQN-UHFFFAOYSA-N 1-bromo-2,2-dimethylpropane-1,3-diol Chemical compound CC(C)(CO)C(O)Br RVPAFPCXAYNVQN-UHFFFAOYSA-N 0.000 description 1
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
- IDQBJILTOGBZCR-UHFFFAOYSA-N 1-butoxypropan-1-ol Chemical compound CCCCOC(O)CC IDQBJILTOGBZCR-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- VYWBWUAOJOPFSB-UHFFFAOYSA-N 1-methyl-1-(3,3,5-trimethylcyclohexyl)hydrazine Chemical compound NN(C1CC(CC(C1)(C)C)C)C VYWBWUAOJOPFSB-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- QBVPQGCMIRSSNH-UHFFFAOYSA-N 1-methylsilylprop-2-en-1-one Chemical compound C[SiH2]C(=O)C=C QBVPQGCMIRSSNH-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 1
- YXOKJIRTNWHPFS-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diamine Chemical compound NCC(C)CCC(C)CN YXOKJIRTNWHPFS-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- PQWKLUKTIZEJHB-UHFFFAOYSA-N 2-(hexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)OCC1CO1 PQWKLUKTIZEJHB-UHFFFAOYSA-N 0.000 description 1
- JPEGUDKOYOIOOP-UHFFFAOYSA-N 2-(hexoxymethyl)oxirane Chemical compound CCCCCCOCC1CO1 JPEGUDKOYOIOOP-UHFFFAOYSA-N 0.000 description 1
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 1
- DXEHULHXWHEJJD-UHFFFAOYSA-N 2-[(4-butylphenoxy)methyl]oxirane Chemical compound C1=CC(CCCC)=CC=C1OCC1OC1 DXEHULHXWHEJJD-UHFFFAOYSA-N 0.000 description 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 1
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NTYQWXQLHWROSQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2,2,2-tris(sulfanyl)acetic acid Chemical compound OC(=O)C(S)(S)S.CCC(CO)(CO)CO NTYQWXQLHWROSQ-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 1
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 1
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 1
- YHCFCGMLDLHIOQ-UHFFFAOYSA-N 3-(1-amino-2-methylpropyl)-3,5,5-trimethyl-n-propan-2-ylcyclohexan-1-amine Chemical class CC(C)NC1CC(C)(C)CC(C)(C(N)C(C)C)C1 YHCFCGMLDLHIOQ-UHFFFAOYSA-N 0.000 description 1
- DVFGEIYOLIFSRX-UHFFFAOYSA-N 3-(2-ethylhexoxy)propan-1-amine Chemical compound CCCCC(CC)COCCCN DVFGEIYOLIFSRX-UHFFFAOYSA-N 0.000 description 1
- PWGVOCGNHYMDLS-UHFFFAOYSA-N 3-(2-methoxyethoxy)propan-1-amine Chemical compound COCCOCCCN PWGVOCGNHYMDLS-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- YOOSAIJKYCBPFW-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)butoxy]propan-1-amine Chemical class NCCCOCCCCOCCCN YOOSAIJKYCBPFW-UHFFFAOYSA-N 0.000 description 1
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- JOZZAIIGWFLONA-UHFFFAOYSA-N 3-methylbutan-2-amine Chemical compound CC(C)C(C)N JOZZAIIGWFLONA-UHFFFAOYSA-N 0.000 description 1
- LVACOMKKELLCHJ-UHFFFAOYSA-N 3-trimethoxysilylpropylurea Chemical compound CO[Si](OC)(OC)CCCNC(N)=O LVACOMKKELLCHJ-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 1
- VIOMIGLBMQVNLY-UHFFFAOYSA-N 4-[(4-amino-2-chloro-3,5-diethylphenyl)methyl]-3-chloro-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C(=C(CC)C(N)=C(CC)C=2)Cl)=C1Cl VIOMIGLBMQVNLY-UHFFFAOYSA-N 0.000 description 1
- HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 description 1
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 description 1
- KZTROCYBPMKGAW-UHFFFAOYSA-N 4-[[4-amino-3,5-di(propan-2-yl)phenyl]methyl]-2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=C(N)C(C(C)C)=CC(CC=2C=C(C(N)=C(C(C)C)C=2)C(C)C)=C1 KZTROCYBPMKGAW-UHFFFAOYSA-N 0.000 description 1
- LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 description 1
- PNWSHHILERSSLF-UHFFFAOYSA-N 4-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C(O)=O PNWSHHILERSSLF-UHFFFAOYSA-N 0.000 description 1
- LHRYNURXGHTOSZ-UHFFFAOYSA-N 5,6-dihydrobenzo[b][1]benzoxepine Chemical compound C1CC2=CC=CC=C2OC2=CC=CC=C12 LHRYNURXGHTOSZ-UHFFFAOYSA-N 0.000 description 1
- IRPDMKHBZJZAMO-UHFFFAOYSA-N 5-hydrazinylpentan-1-amine Chemical compound NCCCCCNN IRPDMKHBZJZAMO-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 239000004114 Ammonium polyphosphate Substances 0.000 description 1
- 244000226021 Anacardium occidentale Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DJHUPTRFHSUXHK-UHFFFAOYSA-N C(C(O)CO)OC(C1CO1)(C1=CC=CC=C1)CCCCCCCCC Chemical compound C(C(O)CO)OC(C1CO1)(C1=CC=CC=C1)CCCCCCCCC DJHUPTRFHSUXHK-UHFFFAOYSA-N 0.000 description 1
- QDALQNOXBIWAEI-UHFFFAOYSA-N C(C)(C1=C2C(C(=O)N(C2=O)Br)=C(C(=C1Br)Br)Br)C1=C2C(C(=O)N(C2=O)Br)=C(C(=C1Br)Br)Br Chemical compound C(C)(C1=C2C(C(=O)N(C2=O)Br)=C(C(=C1Br)Br)Br)C1=C2C(C(=O)N(C2=O)Br)=C(C(=C1Br)Br)Br QDALQNOXBIWAEI-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- GABQNAFEZZDSCM-RMKNXTFCSA-N Cinnamyl anthranilate Chemical compound NC1=CC=CC=C1C(=O)OC\C=C\C1=CC=CC=C1 GABQNAFEZZDSCM-RMKNXTFCSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 101100264657 Enterobacteria phage T4 y12D gene Proteins 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- MKYLOMHWHWEFCT-UHFFFAOYSA-N Manthidine Natural products C1C2=CC=3OCOC=3C=C2C2C3=CC(OC)C(O)CC3N1C2 MKYLOMHWHWEFCT-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241001112258 Moca Species 0.000 description 1
- SNFRINMTRPQQLE-JQWAAABSSA-N Montanin Chemical compound O[C@H]([C@@]1(CO)O[C@H]1[C@H]1[C@H]2O3)[C@]4(O)C(=O)C(C)=C[C@H]4[C@]11OC3(CCCCCCCCCCC)O[C@@]2(C(C)=C)C[C@H]1C SNFRINMTRPQQLE-JQWAAABSSA-N 0.000 description 1
- SNFRINMTRPQQLE-OFGNMXNXSA-N Montanin Natural products O=C1[C@@]2(O)[C@@H](O)[C@@]3(CO)O[C@H]3[C@@H]3[C@H]4[C@@]5(C(=C)C)O[C@](CCCCCCCCCCC)(O4)O[C@@]3([C@H](C)C5)[C@@H]2C=C1C SNFRINMTRPQQLE-OFGNMXNXSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- JHXVRRJXCDAINK-UHFFFAOYSA-N NC(=O)N.N#CC#N Chemical compound NC(=O)N.N#CC#N JHXVRRJXCDAINK-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- YHDJLQXSHIIBAQ-UHFFFAOYSA-N OP(O)OP(O)O.C1(=CC=CC=C1)C1=C(C(=C(C(=C1O)C1=CC=CC=C1)O)C1=CC=CC=C1)C1=CC=CC=C1 Chemical class OP(O)OP(O)O.C1(=CC=CC=C1)C1=C(C(=C(C(=C1O)C1=CC=CC=C1)O)C1=CC=CC=C1)C1=CC=CC=C1 YHDJLQXSHIIBAQ-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241001149930 Protura <class> Species 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000405217 Viola <butterfly> Species 0.000 description 1
- QTZPBQMTXNEKRX-UHFFFAOYSA-N Voacristine pseudoindoxyl Natural products N1C2=CC=C(OC)C=C2C(=O)C21CCN(C1)C3C(C(C)O)CC1CC32C(=O)OC QTZPBQMTXNEKRX-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- IDWDEHYPSCTKFU-UHFFFAOYSA-N [3,5-bis(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC(CN)=CC(CN)=C1 IDWDEHYPSCTKFU-UHFFFAOYSA-N 0.000 description 1
- BQPNUOYXSVUVMY-UHFFFAOYSA-N [4-[2-(4-diphenoxyphosphoryloxyphenyl)propan-2-yl]phenyl] diphenyl phosphate Chemical compound C=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 BQPNUOYXSVUVMY-UHFFFAOYSA-N 0.000 description 1
- MCEBKLYUUDGVMD-UHFFFAOYSA-N [SiH3]S(=O)=O Chemical compound [SiH3]S(=O)=O MCEBKLYUUDGVMD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003619 algicide Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- RREGISFBPQOLTM-UHFFFAOYSA-N alumane;trihydrate Chemical compound O.O.O.[AlH3] RREGISFBPQOLTM-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- BLVPVLRUOJHVHB-UHFFFAOYSA-N aluminum;potassium;silicate Chemical compound [Al+3].[K+].[O-][Si]([O-])([O-])[O-] BLVPVLRUOJHVHB-UHFFFAOYSA-N 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 1
- 229920001276 ammonium polyphosphate Polymers 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical class O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 description 1
- 230000006208 butylation Effects 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000020226 cashew nut Nutrition 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
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 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
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- BVURNMLGDQYNAF-UHFFFAOYSA-N dimethyl(1-phenylethyl)amine Chemical compound CN(C)C(C)C1=CC=CC=C1 BVURNMLGDQYNAF-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940093495 ethanethiol Drugs 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- 229960005082 etohexadiol Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011151 fibre-reinforced plastic Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000002241 glass-ceramic Substances 0.000 description 1
- 239000010438 granite Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229920002681 hypalon Polymers 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- VDQVKPUWSIBXEI-UHFFFAOYSA-N n'-(2-ethylhexyl)ethane-1,2-diamine Chemical compound CCCCC(CC)CNCCN VDQVKPUWSIBXEI-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- DFPGBRPWDZFIPP-UHFFFAOYSA-N n'-butylethane-1,2-diamine Chemical compound CCCCNCCN DFPGBRPWDZFIPP-UHFFFAOYSA-N 0.000 description 1
- FCZQPWVILDWRBN-UHFFFAOYSA-N n'-cyclohexylethane-1,2-diamine Chemical compound NCCNC1CCCCC1 FCZQPWVILDWRBN-UHFFFAOYSA-N 0.000 description 1
- ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 description 1
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 1
- ADKFRZBUXRKWDL-UHFFFAOYSA-N n'-hexylethane-1,2-diamine Chemical compound CCCCCCNCCN ADKFRZBUXRKWDL-UHFFFAOYSA-N 0.000 description 1
- LDQWVRMGQLAWMN-UHFFFAOYSA-N n,n'-diethylhexane-1,6-diamine Chemical compound CCNCCCCCCNCC LDQWVRMGQLAWMN-UHFFFAOYSA-N 0.000 description 1
- RUSPWDWPGXKTFO-UHFFFAOYSA-N n-ethyl-2-methoxyaniline Chemical compound CCNC1=CC=CC=C1OC RUSPWDWPGXKTFO-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 description 1
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 description 1
- LTEKQAPRXFBRNN-UHFFFAOYSA-N piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1 LTEKQAPRXFBRNN-UHFFFAOYSA-N 0.000 description 1
- 239000013308 plastic optical fiber Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 239000000441 potassium aluminium silicate Substances 0.000 description 1
- 235000012219 potassium aluminium silicate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 230000008698 shear stress Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000005480 shot peening Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-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
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 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
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
Abstract
本发明涉及用于环氧树脂的低气味低粘度的固化剂,其包含式(I)的胺,
Description
技术领域
本发明涉及胺及其作为用于环氧树脂的固化剂的用途的领域,以及包含胺的环氧树脂-组合物及其特别是作为涂料的用途。
背景技术
环氧树脂组合物应具有一系列性能从而可以用作高品质涂料。其一方面应具有低粘度,以便其在环境温度下可以良好操作并且是自流平的,并且其应即使在湿冷条件下仍然快速固化而无所谓的泛白效应。“泛白”表示在固化时通常通过胺与空气中的二氧化碳(CO2)形成盐而造成的缺陷,例如浑浊、斑点和粗糙或粘性的表面,其中高空气湿度和低温会促进泛白效应。环氧树脂涂料在经固化状态下应具有平坦表面而无浑浊、斑点或凹穴,并且其应具有高硬度和尽可能低的脆性,从而良好抵抗机械负荷,这例如在作为保护涂料或作为地面覆层的用途中是特别重要的。为了实现这些性能,在根据现有技术的环氧树脂涂料中通常使用稀释剂。所述稀释剂(例如苯甲醇或酚)改进可操作性并且剧烈降低脆性,然而在固化时不结合至树脂基质中。目前对于低排放体系的需求变得日益重要,所述低排放体系在固化之后具有低含量的、可以通过蒸发过程或扩散过程释放的物质。因此,对于低排放体系,仅以极少的量使用或完全不使用非结合性的稀释剂。稀释环氧树脂组合物的另一种可能性是加入低分子量的胺,例如异佛尔酮二胺、二甲苯二胺或二甲基氨基丙胺。然而,所述低分子量的胺大多具有强烈气味并且剧烈刺激皮肤,并且在湿冷条件下造成泛白效应。
US2009/0163676描述了包含至少一种苄基化聚亚烷基多胺和至少一种其他的胺的用于环氧树脂的固化剂。US6′562′934描述了包含二胺与烯基化合物的反应产物的用于环氧树脂的固化剂。这两篇文献的固化剂具有的缺点在于,其特别是在低温下与环氧树脂缓慢固化并且在不加入非结合性稀释剂的情况下造成相当脆的涂层。
发明内容
因此本发明的目的是提供用于环氧树脂的固化剂,所述固化剂为低气味和低粘度的并且可以与环氧树脂良好加工,即使在湿冷条件下即使不存在非结合性稀释剂仍然迅速固化而无泛白。
出人意料地发现,根据权利要求1的包含式(I)的胺的固化剂实现所述目的。所述固化剂为低气味和低粘度的并且与环氧树脂出色地相容。所述固化剂即使在湿冷条件下仍然与环氧树脂迅速固化并且形成膜,所述膜无粘性、具有高光泽度、无浑浊和表面缺陷并且具有出人意料的高硬度。由于式(I)的胺不具有伯氨基,而是仅具有两个仲氨基和相对高的NH-当量,所以本领域技术人员本会预期得到缓慢固化的粘性和/或低硬度的膜。
利用根据权利要求1的固化剂可得到低排放的环氧树脂体系,所述环氧树脂体系满足环境认证标准(例如Emicode(EC1Plus)、AgBB、DIBt、DerBlaueEngel、AFSSET、RTS(M1)和美国绿色建筑协会(LEED))的条件并且同时满足加工性能和使用性能方面的高要求,而现有技术的固化剂无法实现这些。
本发明的其它方面为其它独立权利要求的主题。本发明特别优选的实施方案为从属权利要求的主题。
发明的实施方式
本发明的主题是适合于固化环氧树脂的固化剂,所述固化剂包含式(I)的胺。
以“聚/多”为首的物质名称如多胺、多元醇或聚环氧化物,表示形式上每分子包含两个或更多个在其名称中出现的官能团的物质。
“脂族”表示其氨基键合至脂族、脂环族或芳脂族基团的胺;相应地,该基团被称为脂族氨基。
“芳族”表示其氨基键合至芳族基团的胺;相应地,该基团被称为芳族氨基。
“胺氢”表示伯氨基和仲氨基的氢原子。
“NH-当量”表示相对于固化剂或胺中存在的每个胺氢的固化剂或胺的重量份额。
“非结合性稀释剂”表示可溶于环氧树脂并且使其粘度降低的物质,所述物质在环氧树脂固化时不共价结合至树脂基质。
在本文献中术语“粘度”表示通过剪切应力和剪切速率(速度梯度)之间的比例定义并且如DINENISO3219中所述确定的动态粘度或剪切粘度。
式(I)的胺可以特别有利地通过1,3-双-(氨基甲基)苯(=间-二甲苯二胺或MXDA)与苯甲醛的还原性烷基化而获得。在此,相对于1,3-双-(氨基甲基)苯的伯氨基优选以化学计量比使用苯甲醛。还原性烷基化合适地在氢的存在下且在提高的压力下进行。这可以直接采用分子氢而进行或者间接通过其它反应试剂的氢转移而进行。优选使用分子氢。在此,有利地这样选择条件,使得一方面伯氨基尽可能完全还原性烷基化,另一方面苯环不被氢化。优选在5至100bar的氢压下,在40至120℃的温度下和合适催化剂的存在下进行操作。优选作为催化剂的是负载于炭上的钯(Pd/C)、负载于炭上的铂(Pt/C)、Adams-催化剂和雷尼镍,特别是负载于炭上的钯和负载于炭上的铂。
通过还原性烷基化以所述方式制备式(I)的胺对于用作为环氧树脂的固化剂的成分来说是特别有利的,因为伯氨基被高度选择性地烷基化,而仲氨基几乎不会进一步烷基化。通过所述制备获得的产物因此可以在还原性烷基化之后无需进一步的处理而以所述方式用于环氧树脂的固化。
式(I)的胺也可以通过不同于还原性烷基化的其它方式获得,特别是通过1,3-双-(氨基甲基)苯与苄基氯或苄基溴以合适的比例反应而获得。在此过程中形成通常具有显著量的双重烷基化的氨基的反应混合物。
式(I)的胺为具有低粘度的低挥发性的低气味物质。其具有相对于CO2的如此低的反应性使得其(不同于现有技术已知的许多胺)在空气中既不倾向于形成硬皮也不倾向于沉淀或粘度升高。其显示出与其它胺和与环氧树脂的出色的相容性。
包含式(I)的胺的固化剂具有低粘度和相对高的NH-当量并且因此良好地稀释环氧树脂。其特别是即使在低温下仍然与环氧树脂出人意料地迅速固化而无泛白。在平面应用中产生具有出人意料的高硬度的平坦无粘性的膜。
除了式(I)的胺之外,根据本发明的适合于固化环氧树脂的固化剂特别还包含至少一种多胺A,所述多胺A具有至少三个对环氧基团有反应性的胺氢。
包含与多胺A组合的式(I)的胺的固化剂还造成促进环氧树脂的固化,其中获得具有更高硬度和低脆性的经固化的树脂。这对于作为涂料的用途来说是特别有利的。包含与多胺A组合的式(I)的胺的固化剂同样具有低粘度。特别地,当多胺A具有比式(I)的胺显著更高的粘度时,固化剂的粘度也很低。特别是当多胺A具有更高的粘度时,式(I)的胺对多胺A具有显著的稀释作用。因此式(I)的胺允许有效地稀释多胺A而不使用非结合性稀释剂或强烈气味的、倾向于泛白效应的胺。稀释对于粘度高于700mPa·s,特别是高于1,500mPa·s的多胺A来说是特别有利的。通过存在式(I)的胺,出人意料地不负面影响固化剂与环氧树脂的固化速度和所述膜的硬度和表面品质,并且还降低脆性。
适合作为多胺A的特别为如下的多胺:
-脂族、脂环族或芳脂族的伯二胺,例如特别是乙二胺、1,2-丙二胺、1,3-丙二胺、2-甲基-1,2-丙二胺、2,2-二甲基-1,3-丙二胺、1,3-丁二胺、1,4-丁二胺、1,3-戊二胺(DAMP)、1,5-戊二胺、1,5-二氨基-2-甲基戊烷(MPMD)、2-丁基-2-乙基-1,5-戊二胺(C11-新二胺)、1,6-己二胺、2,5-二甲基-1,6-己二胺、2,2,4-和2,4,4-三甲基六亚甲基二胺(TMD)、1,7-庚二胺、1,8-辛二胺、1,9-壬二胺、1,10-癸二胺、1,11-十一烷二胺、1,12-十二烷二胺、1,2-、1,3-和1,4-二氨基环己烷、双-(4-氨基环己基)-甲烷(H12-MDA)、双-(4-氨基-3-甲基环己基)甲烷、双-(4-氨基-3-乙基环己基)-甲烷、双-(4-氨基-3,5-二甲基环己基)-甲烷、双-(4-氨基-3-乙基-5-甲基环己基)-甲烷(M-MECA)、1-氨基-3-氨基甲基-3,5,5-三甲基环己烷(=异佛尔酮二胺或IPDA)、2-和4-甲基-1,3-二氨基环己烷及其混合物、1,3-和1,4-双-(氨基甲基)环己烷、2,5(2,6)-双-(氨基甲基)双环[2.2.1]庚烷(NBDA)、3(4),8(9)-双-(氨基甲基)-三环[5.2.1.02,6]癸烷、1,4-二氨基-2,2,6-三甲基环己烷(TMCDA)、1,8-薄荷烷二胺、3,9-双-(3-氨基丙基)-2,4,8,10-四氧杂螺[5.5]十一烷以及1,3-和1,4-双-(氨基甲基)苯;
-脂族、脂环族或芳脂族的伯三胺,例如4-氨基甲基-1,8-辛二胺、1,3,5-三-(氨基甲基)苯、1,3,5-三-(氨基甲基)环己烷、三-(2-氨基乙基)胺、三-(2-氨基丙基)胺和三-(3-氨基丙基)胺;
-含醚基的脂族伯二胺,例如特别是双-(2-氨基乙基)醚、3,6-二氧杂辛-1,8-二胺、4,7-二氧杂癸-1,10-二胺、4,7-二氧杂癸-2,9-二胺、4,9-二氧杂十二烷-1,12-二胺、5,8-二氧杂十二烷-3,10-二胺、4,7,10-三氧杂十三烷-1,13-二胺和所述二胺的更高级的低聚物,双-(3-氨基丙基)聚四氢呋喃和其它聚四氢呋喃二胺,以及聚氧化亚烷基二胺。后者通常是通过聚氧化亚烷基二醇的胺化形成的产物并且例如可通过名称(来自Huntsman)、名称Polyetheramine(来自BASF)或名称PC(来自Nitroil)获得。特别合适的聚氧化亚烷基二胺为D-230、D-400、D-2000、D-4000、XTJ-511、ED-600、ED-900、ED-2003、XTJ-568、XTJ-569、XTJ-523、XTJ-536、XTJ-542、XTJ-559、EDR-104、EDR-148、EDR-176;PolyetheramineD230、PolyetheramineD400和PolyetheramineD2000、PCDA250、PCDA400、PCDA650和PCDA2000;
-聚氧化亚烷基-伯三胺,其通常是通过聚氧化亚烷基三醇的胺化形成的产物并且例如可通过名称(来自Huntsman)、名称Polyetheramine(来自BASF)或名称PC(来自Nitroil)获得,例如特别是T-403、T-3000、T-5000、PolyetheramineT403、PolyetheramineT5000和PCTA403;
-具有两个脂族伯氨基且含有叔氨基的多胺,例如特别是N,N’-双-(氨基丙基)哌嗪、N,N-双-(3-氨基丙基)甲胺、N,N-双-(3-氨基丙基)乙胺、N,N-双-(3-氨基丙基)丙胺、N,N-双-(3-氨基丙基)环己胺、N,N-双-(3-氨基丙基)-2-乙基-己胺,以及通过脂肪胺的双重氰乙基化和随后的还原获得的产物,所述脂肪胺源自天然脂肪酸,例如N,N-双-(3-氨基丙基)十二烷基胺和N,N-双-(3-氨基丙基)牛脂烷基胺,其可以Y12D和YT(来自AkzoNobel)获得;
-具有三个脂族伯氨基且含有叔氨基的多胺,例如特别是三-(2-氨基乙基)胺、三-(2-氨基丙基)胺和三-(3-氨基丙基)胺;
-具有两个脂族伯氨基且含有仲氨基的多胺,例如特别是3-(2-氨基乙基)氨基丙胺、双-六亚甲基三胺(BHMT)、二亚乙基三胺(DETA)、三亚乙基四胺(TETA)、四亚乙基五胺(TEPA)、五亚乙基六胺(PEHA)和线性聚亚乙基胺的更高级的同系物,例如具有5至7个亚乙基胺单元的聚亚乙基多胺(所谓的“更高级的亚乙基多胺”,HEPA),通过具有至少两个伯氨基的伯二胺和伯多胺的多重氰乙基化或氰丁基化和随后的氢化而获得的产物,例如二亚丙基三胺(DPTA)、N-(2-氨基乙基)-1,3-丙二胺(N3-胺)、N,N’-双(3-氨基丙基)亚乙基二胺(N4-胺)、N,N’-双-(3-氨基丙基)-1,4-二氨基丁烷、N5-(3-氨基丙基)-2-甲基-1,5-戊二胺、N3-(3-氨基戊基)-1,3-戊二胺、N5-(3-氨基-1-乙基丙基)-2-甲基-1,5-戊二胺和N,N’-双-(3-氨基-1-乙基丙基)-2-甲基-1,5-戊二胺。
-具有伯氨基和仲氨基的多胺,例如特别是N-甲基-1,2-乙二胺、N-乙基-1,2-乙二胺、N-丁基-1,2-乙二胺、N-己基-1,2-乙二胺、N-(2-乙基己基)-1,2-乙二胺、N-环己基-1,2-乙二胺、4-氨基甲基-哌啶、N-(2-氨基乙基)哌嗪、N-甲基-1,3-丙二胺、N-丁基-1,3-丙二胺、N-(2-乙基己基)-1,3-丙二胺、N-环己基-1,3-丙二胺、3-甲基氨基-1-戊基胺、3-乙基氨基-1-戊基胺、3-环己基氨基-1-戊基胺、脂肪二胺例如N-椰油烷基-1,3-丙二胺和通过脂族伯二胺与丙烯腈、马来酸二酯或富马酸二酯、柠康酸二酯、丙烯酸酯和甲基丙烯酸酯、丙烯酰胺和甲基丙烯酰胺和衣康酸二酯以1:1的摩尔比反应的迈克尔型加成反应而获得的产物,此外还有由脂族伯多胺与苯甲醛或其他醛或酮的部分还原性烷基化而得到的产物,以及部分苯乙烯化的多胺如Gaskamine240(来自MitsubishiGasChemical(MGC));
-芳族多胺,例如特别是间-和对-苯二胺、4,4’-、2,4’和2,2’-二氨基二苯甲烷、3,3’-二氯-4,4’-二氨基二苯甲烷(MOCA)、2,4-和2,6-甲苯二胺、3,5-二甲基硫代-2,4-和-2,6-甲苯二胺的混合物(可作为300获自Albemarle)、3,5-二乙基-2,4-和-2,6-甲苯二胺的混合物(DETDA)、3,3’,5,5’-四乙基-4,4’-二氨基二苯甲烷(M-DEA)、3,3’,5,5’-四乙基-2,2’-二氯-4,4’-二氨基二苯甲烷(M-CDEA)、3,3’-二异丙基-5,5’-二甲基-4,4’-二氨基二苯基甲烷(M-MIPA)、3,3’,5,5’-四异丙基-4,4’-二氨基二苯基甲烷(M-DIPA)、4,4’-二氨基二苯基砜(DDS)、4-氨基-N-(4-氨基苯基)苯磺酰胺、5,5’-亚甲基二羧甲基邻氨基苯甲酸、二甲基-(5,5’-亚甲基二邻氨基苯甲酸酯)、1,3-亚丙基-双-(4-氨基苯甲酸酯)、1,4-亚丁基-双-(4-氨基苯甲酸酯)、聚氧亚丁基-双-(4-氨基苯甲酸酯)(可作为获自AirProducts)、1,2-双-(2-氨基苯基硫代)乙烷、2-甲基丙基-(4-氯-3,5-二氨基苯甲酸酯)和叔丁基-(4-氯-3,5-二氨基苯甲酸酯);
-所述多胺与环氧化物和环氧树脂的加合物,特别是与二环氧化物以至少2/1的摩尔比的加合物,与单环氧化物以至少1/1的摩尔比的加合物,以及胺和表氯醇的反应产物,特别是1,3-双-(氨基甲基)苯的反应产物,其可作为328市售获得(来自MGC);
-聚酰胺基胺,所述聚酰胺基胺是一价或多价羧酸或者其酯或酸酐,特别是二聚脂肪酸,和化学计量上过量使用的脂族、脂环族或芳族的多胺,特别是聚亚烷基胺例如DETA或TETA的反应产物,特别是可市售获得的聚酰胺基胺100、125、140和150(来自Cognis)、223、250和848(来自Huntsman)、3607和530(来自Huntsman)和EH651、EH654、EH655、EH661和EH663(来自Cytec);和
-腰果酚改性胺(Phenalkamine),也被称为曼尼希碱,其是酚(特别是腰果酚)与醛(特别是甲醛)和多胺的曼尼希反应的反应产物,特别是可市售获得的腰果酚改性胺NC-541、NC-557、NC-558、NC-566、Lite2001和Lite2002(来自Cardolite)、3440、3441、3442和3460(来自Huntsman)和EH614、EH621、EH624、EH628和EH629(来自Cytec)。
优选作为多胺A的是选自如下的多胺:1,3-戊二胺(DAMP)、1,5-二氨基-2-甲基戊烷(MPMD)、2-丁基-2-乙基-1,5-戊二胺(C11-新二胺)、1,6-己二胺、2,2,4-和2,4,4-三甲基六亚甲基二胺(TMD)、1,12-十二烷二胺、1,3-二氨基环己烷、双-(4-氨基环己基)甲烷(H12-MDA)、双-(4-氨基-3-甲基环己基)甲烷、1-氨基-3-氨基甲基-3,5,5-三甲基环己烷(IPDA)、1,3-双-(氨基甲基)环己烷、1,3-双-(氨基甲基)苯(MXDA)、双-六亚甲基三胺(BHMT)、二亚乙基三胺(DETA)、三亚乙基四胺(TETA)、四亚乙基五胺(TEPA)、五亚乙基六胺(PEHA)和线性聚亚乙基胺的更高级的同系物如具有5至7个亚乙基胺单元的聚亚乙基多胺(HEPA)、二亚丙基三胺(DPTA)、N-(2-氨基乙基)-1,3-丙二胺(N3-胺)、N,N’-双(3-氨基丙基)乙二胺(N4-胺)、分子量为200至500g/mol的聚氧化亚烷基二胺和聚氧化亚烷基三胺,特别是D-230、D-400和T-403型,聚酰胺基胺、腰果酚改性胺、所述多胺的伯氨基上完全或部分烷基化的化合物和所述多胺与环氧化物和环氧树脂的加合物。
所述优选的多胺A与环氧树脂特别良好地相容并且产生具有极高品质的膜。
特别优选作为多胺A的是具有至少一个仲氨基的多胺,例如腰果酚改性胺,多胺与环氧化物和环氧树脂的加合物,以及在至少一个伯氨基上被烷基化的伯多胺,特别是苯乙烯化的1,3-双-(氨基甲基)苯和苄基化的聚亚烷基胺。所述优选的多胺A几乎不倾向于泛白效应并且即使在湿冷条件下仍然与环氧树脂形成具有特别高品质的膜。然而许多这种胺具有高粘度,使得其在不稀释的情况下作为环氧树脂涂料仅具有不足的可加工性。对于低排放涂料来说,这种胺与式(I)的胺的组合是特别有利的,因为由此可获得低粘度的固化剂,所述低粘度的固化剂几乎不具有泛白倾向并且即使在不存在非结合性稀释剂的情况下仍然固化形成具有高硬度和低脆性的膜。
适合作为多胺A的特别还有包含多种所述多胺的混合物。
最优选作为多胺A的是这样的多胺,其本身与环氧树脂具有作为涂料的良好性能,但是具有相当高的粘度,并且出于可加工性和/或过高脆性的原因而常与非结合性稀释剂(例如苯甲醇、烷基酚、苯乙烯化的酚或烃树脂)混合,从而满足高品质涂料的要求。然而由于所述非结合性稀释剂,所述组合物不适合用于需要低排放体系的应用。相反,由于在固化时完全结合至树脂基质的式(I)的胺,在固化之后不产生排放。
如果除了式(I)的胺之外固化剂还包含多胺A,则式(I)的胺的对环氧基团有反应性的胺氢的数目与多胺A的对环氧基团有反应性的胺氢的数目的比例通常为0.05至5,特别是0.05至2。所述固化剂具有降低的粘度并且与环氧树脂固化形成具有低脆性和可广泛调节的硬度的膜,所述可广泛调节的硬度为在式(I)的胺的较高用量下的适中硬度至在式(I)的胺的较低用量下的高硬度。
所述比例特别优选为0.1至1。所述固化剂的特征在于低粘度并且与环氧树脂迅速固化形成具有高硬度和低脆性的膜。
在所述固化剂中,式(I)的胺与多胺A的重量比例优选在0.2至2、特别是0.4至1.5的范围内。所述固化剂的特征在于低粘度并且与环氧树脂迅速固化形成具有高硬度和低脆性的膜。
除了式(I)的胺之外,根据本发明的固化剂还可以包含至少一种促进剂。
适合作为促进剂的是这样的物质,所述物质促进氨基和环氧基团之间的反应,特别为酸或可水解成酸的化合物,特别是有机羧酸例如乙酸,苯甲酸,水杨酸,2-硝基苯甲酸,乳酸,有机磺酸例如甲磺酸、对甲苯磺酸或4-十二烷基苯磺酸,磺酸酯,其它有机或无机酸例如特别是磷酸,或上述酸和酸酯的混合物;还有叔胺例如特别是1,4-二氮杂双环[2.2.2]辛烷、苄基二甲基胺、α-甲基苄基二甲基胺、三乙醇胺、二甲基-氨基丙基胺,咪唑例如特别是N-甲基咪唑、N-乙烯基咪唑或1,2-二甲基咪唑,所述叔胺的盐,季铵盐,例如特别是苄基三甲基氯化铵,脒例如特别是1,8-二氮杂双环[5.4.0]十一碳-7-烯,胍例如特别是1,1,3,3-四甲基胍,酚例如特别是双酚,酚树脂和曼尼希碱例如特别是2-(二甲基氨基甲基)酚、2,4,6-三-(二甲基氨基甲基)酚和由酚、甲醛和N,N-二甲基-1,3-丙二胺形成的聚合物,亚磷酸酯例如特别是二-和三苯基亚磷酸酯,以及具有巯基的化合物如上文已经提及的那些。
优选的促进剂为水杨酸和2,4,6-三-(二甲基氨基甲基)酚。
除了式(I)的胺之外,根据本发明的固化剂还可以包含至少一种非结合性稀释剂,例如特别是二甲苯、2-甲氧基乙醇、二甲氧基乙醇、2-乙氧基乙醇、2-丙氧基乙醇、2-异丙氧基乙醇、2-丁氧基乙醇、2-苯氧基乙醇、2-苄氧基乙醇、苯甲醇、乙二醇、乙二醇二甲醚、乙二醇二乙醚、乙二醇二丁醚、乙二醇二苯醚、二乙二醇、二乙二醇-单甲醚、二乙二醇-单乙醚、二乙二醇-单-正丁醚、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇二-正丁醚、丙二醇丁醚、丙二醇苯醚、二丙二醇、二丙二醇单甲醚、二丙二醇二甲醚、二丙二醇二-正丁醚、N-甲基吡咯烷酮、二苯基甲烷、二异丙基萘,石油馏分例如-型(来自Exxon),烷基酚例如叔丁基酚、壬基酚、十二烷基酚和8,11,14-十五碳三烯基醇(来自腰果壳油的腰果酚,例如可作为CardoliteNC-700获自CardoliteCorp.,USA)、苯乙烯化的酚、双酚,芳族烃树脂,特别是含酚基型的,己二酸酯、癸二酸酯、邻苯二甲酸酯、苯甲酸酯、有机磷酸酯和磺酸酯和磺酰胺。优选的是苯甲醇、十二烷基酚、叔丁基酚、苯乙烯化的酚和含酚基的芳族烃树脂,特别是-型LS500、LX200、LA300和LA700(来自Rütgers)。
所述固化剂优选不包含或仅包含少量的,特别优选小于25重量%、特别是小于10重量%和最优选小于5重量%的非结合性稀释剂。特别地,在所述固化剂中不加入非结合性稀释剂。
所述固化剂还可以包含其它对环氧基团有反应性的物质,例如特别是
-一元胺,例如特别是苄胺、环己胺、2-苯基乙胺、2-甲氧基苯基乙胺、4-甲氧基苯基乙胺、3,4-二甲氧基苯基乙胺(高藜芦胺)、1-和2-丁胺、异丁胺、叔丁胺、3-甲基-2-丁胺、1-己胺、1-辛胺、2-乙基-1-己胺、2-甲氧基-1-乙胺、2-乙氧基-1-乙胺、3-甲氧基-1-丙胺、3-乙氧基-1-丙胺、3-(2-乙基己氧基)丙胺、3-(2-甲氧基乙氧基)丙胺;
-脂族仲多胺,例如特别是N,N’-二丁基-乙二胺、N,N’-二叔丁基-乙二胺、N,N’-二乙基-1,6-己二胺、1-(1-甲基乙基-氨基)-3-(1-甲基乙基-氨基甲基)-3,5,5-三甲基环己烷(来自Huntsman的754)、N4-环己基-2-甲基-N2-(2-甲基丙基)-2,4-戊二胺、N,N’-二烷基-1,3-二甲苯二胺、双-(4-(N-3-丁基氨基)-环己基)-甲烷(来自UOP的1000)、N-烷基化的聚醚胺,例如-型SD-231、SD-401、ST-404和SD-2001(来自Huntsman),通过脂族伯多胺与迈克尔受体例如丙烯腈、马来酸二酯、富马酸二酯、柠康酸二酯、丙烯酸酯、甲基丙烯酸酯、肉桂酸酯、衣康酸二酯、乙烯基膦酸二酯、乙烯基磺酸芳基酯、乙烯砜、乙烯腈、1-硝基乙烯的迈克尔型加成反应获得的产物,或例如通过丙二酸二酯和醛例如甲醛、乙醛或苯甲醛获得的诺文葛耳-缩合产物,以及还有脂族伯多胺与苯甲醛或其它醛或酮的还原性烷基化的产物;
-硫醇封端的液体聚硫化物-聚合物,其以商标名(来自MortonThiokol;例如可获自SPISupplies,或来自TorayFineChemicals)已知,特别是LP-3、LP-33、LP-980、LP-23、LP-55、LP-56、LP-12、LP-31、LP-32和LP-2型;以及还有以商标名(来自AkzoNobel)已知的,特别是G10、G112、G131、G1、G12、G21、G22、G44和G4型;
-硫醇封端的聚氧化亚烷基-醚,其例如可通过聚氧化亚烷基二醇和聚氧化亚烷基三醇与表氯醇或与氧化烯,然后与硫氢化钠的反应获得;
-以聚氧化亚烷基衍生物形式的硫醇封端的化合物,其以商标名(来自Cognis)已知,特别是WR-8、LOF和3-800型;
-硫代羧酸的聚酯,例如季戊四醇四巯基乙酸酯、三羟甲基丙烷三巯基乙酸酯、乙二醇二巯基乙酸酯、季戊四醇四-(3-巯基丙酸酯)、三羟甲基丙烷三-(3-巯基丙酸酯)和乙二醇二-(3-巯基丙酸酯),以及聚氧化亚烷基二醇和聚氧化亚烷基三醇、乙氧基化的三羟甲基丙烷和聚酯二醇与硫代羧酸例如硫代乙醇酸和2-或3-巯基丙酸的酯化产物;和
-其它具有巯基的化合物,例如特别是2,4,6-三巯基-1,3,5-三嗪、2,2’-(亚乙基二氧基)-二乙烷硫醇(三乙二醇-二硫醇)和乙二硫醇。
本发明的另一个主题是环氧树脂组合物,其包含
a)至少一种环氧树脂,和
b)至少一种包含如上所述的式(I)的胺的固化剂。
常见的工业环氧树脂适合作为环氧树脂。其以已知的方式和方法获得,例如通过相应烯烃的氧化或者通过表氯醇与相应多元醇、多酚或胺的反应获得。
特别适合作为环氧树脂的是所谓的聚环氧化物液体树脂,下文中称为“液体树脂”。不同于所谓的固体树脂,液体树脂具有通常低于25℃的玻璃化转变温度,所述固体树脂具有高于25℃的玻璃化转变温度并且在25℃以下可以粉碎成能自由流动的粉末。
在一个实施方案中,液体树脂为芳族聚环氧化物。为此,合适的有例如式(II)的液体树脂,
其中R’和R’’彼此独立地各自表示氢原子或甲基,并且s平均表示0至1的值。优选这样的式(II)的液体树脂,其中指数s平均表示小于0.2的值。
式(II)的液体树脂为双酚-A、双酚-F和双酚-A/F的二缩水甘油醚,其中A表示丙酮和F表示甲醛,其充当用于制备所述双酚的反应物。与此相应的,双酚-A-液体树脂具有甲基,双酚-F-液体树脂具有氢原子,和双酚-A/F-液体树脂具有甲基和氢原子作为式(II)中的R’和R’’。在双酚-F的情况下也可以存在特别是源自2,4’-和2,2’-羟基苯基甲烷的位置异构体。
其它合适的芳族液体树脂为如下物质的缩水甘油基化产物:
-二羟基苯衍生物例如间苯二酚、对苯二酚和焦儿茶酚;
-其它双酚或多酚例如双-(4-羟基-3-甲基苯基)-甲烷、2,2-双-(4-羟基-3-甲基苯基)-丙烷(双酚-C)、双-(3,5-二甲基-4-羟基苯基)-甲烷、2,2-双-(3,5-二甲基-4-羟基苯基)-丙烷、2,2-双-(3,5-二溴-4-羟基苯基)-丙烷、2,2-双-(4-羟基-3-叔丁基苯基)-丙烷、2,2-双-(4-羟基苯基)-丁烷(双酚-B)、3,3-双-(4-羟基苯基)-戊烷、3,4-双-(4-羟基苯基)-己烷、4,4-双-(4-羟基苯基)-庚烷、2,4-双-(4-羟基苯基)-2-甲基丁烷、2,4-双-(3,5-二甲基-4-羟基苯基)-2-甲基丁烷、1,1-双-(4-羟基苯基)-环己烷(双酚-Z)、1,1-双-(4-羟基苯基)-3,3,5-三甲基环己烷(双酚-TMC)、1,1-双-(4-羟基苯基)-1-苯基乙烷、1,4-双[2-(4-羟基苯基)-2-丙基]-苯)(双酚-P)、1,3-双-[2-(4-羟基苯基)-2-丙基]-苯)(双酚-M)、4,4’-二羟基联苯(DOD)、4,4’-二羟基苯甲酮、双-(2-羟基萘-1-基)-甲烷、双-(4-羟基萘-1-基)-甲烷1,5-二羟基-萘、三-(4-羟基苯基)-甲烷、1,1,2,2-四-(4-羟基苯基)-乙烷、双-(4-羟基苯基)-醚、双-(4-羟基苯基)砜;
-酚与甲醛的在酸性条件下获得的缩合产物,例如酚-酚醛线性清漆或甲酚-酚醛线性清漆,也被称为双酚-F-酚醛线性清漆;
-芳族胺,例如苯胺、对甲苯胺、4-氨基酚、4,4’-亚甲基二苯基二胺(MDA)、4,4’-亚甲基二苯基二-(N-甲基)-胺、4,4′-[1,4-亚苯基-双-(1-甲基-亚乙基)]-二苯胺(二苯胺-P)、4,4′-[1,3-亚苯基-双-(1-甲基-亚乙基)]-二苯胺(二苯胺-M)。
适合作为环氧树脂的还有脂族或脂环族聚环氧化物,例如
-饱和或不饱和、支化或非支化、环状或开链的C2-至C30-二醇(例如乙二醇、丙二醇、丁二醇、己二醇、辛二醇、聚丙二醇、二羟甲基环己烷、新戊二醇或二溴-新戊二醇)的缩水甘油醚;
-三官能或四官能、饱和或不饱和、支化或非支化、环状或开链多元醇(例如蓖麻油、三羟甲基丙烷、三羟甲基乙烷、季戊四醇、山梨醇或甘油,以及烷氧基化甘油或烷氧基化的三羟甲基丙烷)的缩水甘油醚;
-氢化的双酚-A-、-F-或-A/F-液体树脂,或氢化的双酚-A-、-F-或-A/F的缩水甘油基化产物;
-酰胺或杂环氮碱的N-缩水甘油基衍生物,例如三缩水甘油基氰脲酸酯和三缩水甘油基异氰脲酸酯,以及表氯醇和乙内酰脲的反应产物。
还有可能作为环氧树脂的是双酚-A-、-F-或-A/F-固体树脂,其具有与已经提及的式(II)的液体树脂相似的结构,但是代替所述指数s而具有2至12的数值,并且具有高于25℃的玻璃化转变温度。
最后,适合作为环氧树脂的还有通过烯烃的氧化,例如通过乙烯基环己烯、二环戊二烯、环己二烯、环十二碳二烯、环十二碳三烯、异戊二烯、1,5-己二烯、丁二烯、聚丁二烯或二乙烯基苯的氧化获得的环氧树脂。
优选作为环氧树脂的为基于双酚,特别是基于双酚-A、双酚-F-或双酚-A/F的液体树脂,例如从Dow、Huntsman和Hexion市售购得的那些。这些液体树脂具有对于环氧树脂来说较低的粘度并且在固化状态下具有作为涂料的良好性能。其可以任选与双酚A-固体树脂或双酚-F-酚醛线性清漆-环氧树脂组合存在。
环氧树脂可以包含反应性稀释剂,特别是具有至少一个环氧基团的反应性稀释剂。适合作为反应性稀释剂的是例如一价或多价酚和脂族或脂环族醇的缩水甘油醚,例如特别是已经提及的二醇或多元醇的聚缩水甘油醚,以及还有特别是苯基缩水甘油醚、甲苯基缩水甘油醚、对-正丁基-苯基缩水甘油醚、对-叔丁基-苯基缩水甘油醚、壬基苯基缩水甘油醚、烯丙基缩水甘油醚、丁基缩水甘油醚、己基缩水甘油醚、2-乙基己基缩水甘油醚,以及天然醇的缩水甘油醚,例如C8-至C10-烷基缩水甘油醚或C12-至C14-烷基缩水甘油醚。向环氧树脂中加入反应性稀释剂造成粘度降低,以及——在环氧树脂组合物的固化状态下——玻璃化转变温度和机械值降低。
所述环氧树脂组合物任选包含其它成分,特别是在环氧树脂组合物中常规使用的助剂和添加剂,例如如下物质:
–溶剂、稀释剂、成膜助剂或增量剂,例如特别是已经提及的非结合性稀释剂;
–反应性稀释剂,特别是具有环氧基团的反应性稀释剂,例如上文提到的那些,环氧化豆油或亚麻籽油,具有乙酰乙酸酯基团的化合物,特别是乙酰乙酸酯化的多元醇,丁内酯,碳酸酯,醛,以及还有异氰酸酯和具有反应性基团的硅酮;
–聚合物,例如聚酰胺、聚硫化物、聚乙烯醇缩甲醛(PVF)、聚乙烯醇缩丁醛(PVB)、聚氨酯(PUR)、具有羧基的聚合物、聚酰胺、丁二烯-丙烯腈-共聚物、苯乙烯-丙烯腈-共聚物、丁二烯-苯乙烯-共聚物、不饱和单体(特别选自乙烯、丙烯、丁烯、异丁烯、异戊二烯、乙酸乙烯酯和(甲基)丙烯酸烷基酯)的均聚物或共聚物,特别是氯磺化聚乙烯和含氟聚合物、磺酰胺改性的三聚氰胺和纯化的褐煤蜡;
–无机和有机填料,例如任选涂布有脂肪酸、特别是硬脂酸酯的研磨碳酸钙或沉淀碳酸钙,重晶石(Schwerspat),滑石,石英粉,石英砂,云母铁矿(Eisenglimmer),白云石,硅灰石,高岭土,云母(钾-铝-硅酸盐),分子筛,氧化铝,氢氧化铝,氢氧化镁,二氧化硅,水泥,石膏,飞灰,炭黑,石墨,金属粉末例如铝、铜、铁、锌、银或钢,PVC-粉末或空心球;
–纤维,特别是玻璃纤维、碳纤维、金属纤维、陶瓷纤维或塑料纤维,例如聚酰胺纤维或聚乙烯纤维;
–颜料,例如二氧化钛和氧化铁;
–上述促进剂;
–流变改性剂,例如特别是增稠剂,例如层状硅酸盐如膨润土、蓖麻油衍生物、氢化蓖麻油、聚酰胺、聚氨酯、脲化合物、热解二氧化硅、纤维素醚和疏水改性的聚氧乙烯;
–粘附促进剂,例如有机烷氧基硅烷如氨基硅烷、巯基硅烷、环氧硅烷、乙烯基硅烷、(甲基)丙烯酰基硅烷、异氰酰基硅烷、氨基甲酰基硅烷、烷基硅烷、S-(烷基羰基)-巯基硅烷和醛亚氨基硅烷以及这些硅烷的低聚形式,特别是3-缩水甘油基氧丙基三甲氧基硅烷、3-氨基丙基三甲氧基硅烷、N-(2-氨基乙基)-3-氨基丙基-三甲氧基硅烷、N-(2-氨基乙基)-N′-[3-(三甲氧基甲硅烷基)丙基]乙二胺、3-巯基丙基三甲氧基硅烷、3-异氰酰基丙基三甲氧基硅烷、3-脲基丙基三甲氧基硅烷、3-氯丙基三甲氧基硅烷、乙烯基三甲氧基硅烷,或相应的具有乙氧基代替甲氧基的有机硅烷;
–抵抗氧化、热、光和紫外线的稳定剂;
–阻燃物质,特别是如下化合物:如氢氧化铝(Al(OH)3;对于“三水合铝”也被称为ATH)、氢氧化镁(Mg(OH)2;对于“二水合镁”也被称为MDH)、硫酸铵((NH4)2SO4)、硼酸(B(OH)3)、硼酸锌、磷酸锌、硼酸三聚氰胺和氰脲酸三聚氰胺;含磷化合物例如磷酸铵((NH4)3PO4)、多磷酸铵、磷酸三聚氰胺、焦磷酸三聚氰胺、磷酸三苯酯、磷酸二苯基甲苯基酯、磷酸三甲苯基酯、磷酸三乙酯、三-(2-乙基己基)磷酸酯、磷酸三辛酯、单-、双-和三-(异丙基苯基)磷酸酯、间苯二酚-双(磷酸二苯酯)、间苯二酚-二磷酸酯-低聚物、四苯基-间苯二酚-二亚磷酸酯、乙二胺-二磷酸酯和双酚-A-双(磷酸二苯酯);含卤素的化合物例如氯烷基磷酸酯,特别是三-(氯乙基)磷酸酯、三-(氯丙基)磷酸酯和三-(二氯异丙基)磷酸酯,多溴二苯醚,特别是十溴二苯醚、多溴二苯基氧化物、三-[3-溴-2,2-双(溴甲基)丙基]磷酸酯、四溴-双酚-A、双酚-A的双-(2,3-二溴丙基醚)、溴化环氧树脂、亚乙基-双(四溴邻苯二甲酰亚胺)、亚乙基-双(二溴降莰烷二甲酰亚胺)、1,2-双-(三溴苯氧基)乙烷、三-(2,3-二溴丙基)异氰脲酸酯、三溴酚、六溴环十二烷、双-(六氯环戊二烯基)环辛烷和氯化石蜡;以及含卤素化合物和三氧化锑(Sb2O3)或五氧化锑(Sb2O5)的组合;
–表面活性物质,例如润湿剂、流平剂、脱气剂或消泡剂;
–杀生物剂,例如杀藻剂、杀真菌剂或菌类生长抑制物质。
环氧树脂组合物优选包含其它助剂和添加剂,特别是润湿剂、流平剂、消泡剂、稳定剂、颜料和促进剂,特别是水杨酸或2,4,6-三-(二甲基氨基甲基)酚。
环氧树脂组合物优选不包含或仅包含少量的,特别优选小于10重量%、特别是小于5重量%和最优选小于2重量%的非结合性稀释剂。
在环氧树脂组合物中,对环氧基团有反应性的基团的数目与环氧基团的数目的比例为0.5至1.5,优选0.7至1.2。
环氧树脂组合物中存在的胺氢和任选存在的其它对环氧基团有反应性的基团通过其开环(加成反应)与环氧基团反应。所述反应的结果是所述组合物聚合并且最终固化。本领域技术人员已知,伯氨基对于环氧基团来说是双官能的,因此伯氨基被认为是两个对环氧基团有反应性的基团。
特别地,环氧树脂组合物为由如下物质组成的双组分组合物
(i)包含至少一种环氧树脂的树脂组分,和
(ii)包含具有如上所述的式(I)的胺的固化剂的固化剂组分。
双组分组合物的组分可以分别储存在各自的容器中。双组分环氧树脂组合物的其它成分可以作为树脂组分或固化剂组分的成分存在,其中对环氧基团有反应性的其它成分优选为固化剂组分的成分。用于储存树脂组分或固化剂组分的合适的容器特别是桶、瓶、袋、斗、罐、料盒或管。组分是具有储存能力的,亦即其在使用之前可以保存数月至一年和更久,而不以与其使用相关的程度改变其各自的性能。
为了使用双组分环氧树脂组合物,在紧接着施用之前或施用过程中使树脂组分和固化剂组分彼此混合。两种组分之间的混合比例优选这样选择,使得固化剂组分的对环氧基团有反应性的基团以对树脂组分的环氧基团合适的比例存在,如上文所述。以重量份计,树脂组分和固化剂组分之间的混合比例通常为1:10至10:1。
两种组分的混合通过合适方法进行;其可以连续或间歇式进行。如果在施用之前进行混合,则必须注意的是,在组分的混合和施用之间不能停留过多的时间,因为这样会造成干扰,例如延缓地或不完全地建立对于基材的粘附。混合特别在环境温度下进行,所述环境温度通常为约5至50℃,优选约10至30℃。
通过两种组分的混合开始通过化学反应而固化,如上文所述。固化特别在环境温度下进行,所述环境温度通常为约5至50℃,优选约10至30℃。固化通常持续数天至数周,直至其在给定条件下基本完成。持续时间主要取决于温度、成分的反应性及其化学计量比以及促进剂的存在。
因此,本发明的另一个主题是通过如本申请中描述的环氧树脂组合物的固化获得的经固化的组合物。
环氧树脂组合物的施用在至少一种基材上进行,其中如下物质是特别合适的:
–玻璃、玻璃陶瓷、混凝土、砂浆、砖、瓦、石膏和天然石材例如花岗石或大理石;
–金属和合金,例如铝、铁、钢和有色金属,以及经表面处理的金属和合金,例如镀锌或镀铬的金属;
–皮革、织物、纸、木材、与树脂(例如酚树脂、三聚氰胺树脂或环氧树脂)结合的木质材料、树脂-织物-复合材料和其它所谓的聚合物复合物;
–塑料,例如聚氯乙烯(硬质和软质PVC)、丙烯腈-丁二烯-苯乙烯-共聚物(ABS)、聚碳酸酯(PC)、聚酰胺(PA)、聚酯、聚(甲基丙烯酸甲酯)(PMMA)、聚酯、环氧树脂、聚氨酯(PUR)、聚甲醛(POM)、聚烯烃(PO)、聚乙烯(PE)或聚丙烯(PP)、乙烯/丙烯-共聚物(EPM)和乙烯/丙烯/二烯-三元聚合物(EPDM),其中所述塑料优选可以通过等离子体、电晕或火焰进行表面处理;
–纤维增强的塑料,例如碳纤维增强的塑料(CFK)、玻璃纤维增强的塑料(GFK)和片状模塑复合材料(SMC);
–经涂布的基材,例如经粉末涂布的金属或合金;
–染料和漆料,特别是汽车面漆。
基材可以在需要的情况下在施用环氧树脂组合物之前进行预处理。这种预处理包括特别是物理和/或化学清洁方法,例如打磨、喷砂、喷丸、梳理等,其中有利地抽走由此产生的粉尘,以及另外用清洁剂或溶剂处理,或施加粘附促进剂、粘附促进剂剂溶液或底漆。
所述环氧树脂组合物可以有利地用作纤维复合材料(复合物)、浇铸材料、密封剂、粘合剂、覆面、涂料、涂层、漆、密封料、底涂剂、底漆、泡沫、成型块、弹性体、纤维、箔或膜。
其特别可用作浇铸材料、密封剂和粘合剂,例如用作电浇铸料、密封料、二道浆、填缝剂、安装粘合剂、车身粘合剂、夹心元件粘合剂、轴瓦粘合剂(例如用于风力发电站的转子叶片)、桥接元件粘合剂、层合粘合剂、层压粘合剂或锚固粘合剂;以及还有作为用于建筑应用和工业应用的覆面、涂料、涂层、漆、密封料、底涂剂和底漆,例如特别是作为用于室内(如办公室、工业车间、健身房或冷藏室)或室外区域(用于阳台、露台、停车场楼层(Parkdeck)、桥梁或屋顶)的地面覆面和地面涂料,作为用于混凝土、水泥、金属或塑料的保护涂料,例如用于装料区、水槽、筒仓、竖井、管道、管线、机器或钢制结构,例如船舶、码头、海上平台、闸门、水力发电站、治河工程、游泳池、风力发电站、桥梁、烟囱、水管或板桩墙的表面密封,其中所述涂料特别保护各个基材抵抗腐蚀、磨损、湿气、水影响和/或盐影响或化学试剂;以及还有用作预涂漆、粘附漆、防腐蚀底漆或用于使表面疏水化。所述组合物还特别适合在水中和水面,特别是在海水中和海水水面作为用于所谓的防重度腐蚀的涂料。特别地,当其用作涂料、覆面或刷涂料时,可以在完全或部分固化的环氧树脂组合物上施用另一涂料、另一覆面或另一刷涂料,其中所述另一层同样可以是环氧树脂组合物,但是也可以是其它材料,特别是聚氨酯涂料或聚脲涂料。
特别有利地,所述环氧树脂组合物可用作涂料。在此,涂料被理解为任何种类的平面施涂的覆面,特别是涂层、漆料、密封料、底涂剂和底漆,如上文所述。特别有利地,所述环氧树脂组合物可用于具有环境认证标准(例如Emicode(EC1Plus)、AgBB、DIBt、DerBlaueEngel、AFSSET、RTS(M1)和美国绿色建筑协会(LEED))的低排放体系。
因此,本发明的另一个主题是所述环氧树脂组合物作为涂料的用途。
作为涂料,环氧树脂组合物有利地用在涂布方法中,其中所述环氧树脂组合物具有低粘度的液体稠度和良好的流平性能,并且特别可以作为自流平涂料在基本平坦的表面上施用或者作为刷涂层施用。紧接着在混合树脂组分和固化剂组分之后,环氧树脂组合物在施用中优选具有在20℃下测得的300至2,000mPa·s、优选300至1,500mPa·s、特别是300至1,000mPa·s的粘度。在环境温度下在操作时间内将经混合的组合物以层厚度通常为约50μm至约5mm的薄膜的形式平面地施用至基材。例如通过浇铸在待涂布的基材上进行施用。在此过程中,例如借助于刮刀或抹刀使液体状态下的组合物均匀分布。此外,通过钉辊(Stachelwalze)使经分布的组合物拉平和脱气。但是所述施用也可以通过刷子或辊子手动进行或者以喷涂使用形式例如作为钢材上的防腐蚀涂料进行。在固化中通常产生具有低脆性的基本透明有光泽且无粘性的膜,所述膜对于不同基材具有良好粘附性并且具有高硬度。由于固化剂中式(I)的胺而获得自流平的环氧树脂涂料,所述自流平环氧树脂涂料不具有或仅具有少量非结合性稀释剂即已足够,并且涂料中的伯氨基的含量可以保持足够低,使得几乎不与空气中的CO2发生反应。因此,在平面使用中,即使在不利(即有利于泛白)的反应条件下,特别是在5至10℃的低固化温度和高空气湿度下,泛白效应基本上消失。
本发明的另一个主题是通过使用所述环氧树脂组合物作为涂料而获得的制品。
所述环氧树脂组合物的特征在于大量有利的性能。其仅具有很少气味并且在室温下出人意料地为稀液状,因此即使在没有其它稀释剂的情况下,特别是即使在平面使用中仍可良好操作。其在环境温度下,特别是即使在湿冷条件下仍然出人意料地迅速固化而无干扰性泛白效应,并且在固化状态下具有出人意料的高硬度和低脆性。因此其能够良好地抵抗机械负荷,这特别在作为保护涂料或作为地板覆面的用途中是特别重要的。经固化的膜通常不浑浊并且具有平坦有光泽、无凹陷和无粘性的表面。
除了式(I)的胺之外还包含至少一种多胺A的环氧树脂组合物具有特别有利的性能。所述环氧树脂组合物显示出出人意料的如下优点的组合:一方面式(I)的胺对组合物具有出色的稀释作用,因此组合物在组分的混合之后就立即具有低粘度,另一方面组合物迅速固化。式(I)的胺还降低泛白效应的倾向,并且组合物最终固化形成在透明度、光泽度、表面粘性方面具有出色品质,具有高硬度和低脆性的膜。由于式(I)的胺不包含伯氨基而仅包含两个仲氨基的事实,迅速固化、可实现的高硬度和无粘性是特别出人意料的。
实施例
下文描述实施例,所述实施例更详细地解释本发明。本发明当然不限于所描述的实施例。
1.测量方法说明
胺含量(即制备的化合物中的氨基的总含量)通过滴定确定(使用冰醋酸中的0.1NHClO4,用结晶紫作为指示剂)并且始终以mmolN/g表示。
红外光谱在Perkin-Elmer的配备有具有ZnSe-晶体的水平ATR-测量单元的FT-IR设备1600上以未稀释膜的形式进行测量;吸收谱带以波数(cm–1)表示(测量窗口:4000–650cm–1)。
1H-NMR-光谱在BrukerDPX-300型光谱仪上在300.13MHz下测量;化学位移δ相对于四甲基硅烷(TMS)以ppm表示。
质谱(FIMS)在ThermoScientificLTQOrbitrapXL型高分辨率质谱仪上测量,其中以10μl/min的注入速度和500μl/min的载体(甲醇中的1mM甲酸铵)流速将500μl溶解在甲醇中的样本(100μg/ml)直接注入质谱仪;通过电喷射离子化(ESI+)进行检测。
粘度(η)在20℃下在恒温锥板式粘度计RheotecRC30(圆锥直径50mm,圆锥角1°,锥头至板的距离0.05mm,剪切速度10–100s-1)上进行测量。
2.所使用的物质:
3.胺的制备
胺1:N,N′-二苯甲基-间-二甲苯二胺
在圆底烧瓶中在氮气氛下将21.2g苯甲醛和13.6g1,3-双-(氨基甲基)苯溶解在足量异丙醇中。溶液在室温下搅拌30分钟,然后在80bar的氢气压力、80℃的温度和3ml/min的流速下在具有Pd/C-固体床催化剂的连续操作的氢化装置上进行氢化。为了控制反应,通过红外光谱确定亚胺谱带是否在约1665cm-1处消失。之后在真空中在80℃下浓缩所述溶液。获得在20℃下的粘度为230mPa·s且胺含量为6.41mmolN/g且纯度为94.4%(通过气相色谱确定)的澄清的黄色油。
FT-IR:3024,2910,2810,1604,1494,1452,1108,1028,784,732,694。
1H-NMR(CDCl3,300K):δ7.4–7.1(m,14H,Ar-H),3.77(s,8H,CH2),1.70(s,2H,NH)。
FIMS:m/z=317.20203([MH+];C22H25N2的理论量:317.20123)。
胺2:N-苯甲基-3-(N-苯甲基)氨基甲基-3,5,5-三甲基环己胺
以与实施例1所述的相同的方式使21.2g苯甲醛和17.0g1-氨基-3-氨基甲基-3,5,5-三甲基环己烷(=异佛尔酮二胺)反应。获得在20℃下的粘度为590mPa·s且胺含量为5.82mmolN/g的澄清的无色油。
胺3:N,N′-二苯甲基-2-甲基戊-1,5-二胺
以与实施例1所述的相同的方式使21.2g苯甲醛和11.6g1,5-二氨基-2-甲基戊烷反应。获得在20℃下的粘度为420mPa·s且胺含量为6.67mmolN/g的澄清的黄色油。
4.固化剂的制备
实施例1至5
对于每个实施例,通过离心混合机(SpeedMixerTMDAC150,FlackTekInc.)以给出的量(重量份)混合表1中给出的根据现有技术的固化剂和胺1。混合后1小时分别确定所获得的固化剂的粘度。(胺1的NH-当量的数目和根据现有技术的固化剂的NH-当量的数目之间的比例均为0.33。)
表1:实施例1至5的固化剂的组成和在20℃下测得的粘度。
5.环氧树脂组合物的制备
实施例和对比实施例6至17
对于每个实施例,通过离心混合机(SpeedMixerTMDAC150,FlackTekInc.)以给出的量(重量份)混合表2至4中给出的成分。混合后10分钟确定各个组合物的粘度(“粘度(10’)”)。此外,分别以500μm的层厚度在玻璃板上施涂第一层膜,并且在23±1℃和50±5%相对湿度(=标准气候,下文缩写为“NK”)下放置或固化。4周之后评估膜的外观(表中用“外观(NK)”表示)。“良好”表示清澈并且具有光泽和非粘性表面而无结构的膜。“结构”在此表示表面上任何种类的花纹或图案。此外,在2天之后(“硬度(NK)(2d)”)或四天之后(“硬度(NK)(4d)”)或7天之后(“硬度(NK)(7d)”)或4周之后(“硬度(NK)(4w)”)确定膜的硬度(摆撞硬度,根据DINENISO1522测量)。此外,分别以500μm的层厚度在玻璃板上施涂第二层膜,并且在施用之后立即在8℃和80%相对湿度下放置或固化7天和然后在NK下放置或固化4周。施用后24小时在膜上放置聚丙烯瓶盖,在所述瓶盖下方放置潮湿海绵。再过24小时之后除去海绵和盖并且将其放置在膜的新位置处,在该新位置处24小时之后将其再度除去并且重新放置,总共4次。然后以与针对外观(NK)所述的相同方式评估该膜的外观(在表中用“外观(8°/80%)”表示)。表中也分别给出由于潮湿海绵和/或放置的盖而在膜中可见的标记的数量。如果在标记处出现变色或浑浊,则也在表中标明。再次地,分别在8℃和80%相对湿度下在7天之后(“(8°/80%)(7d冷)”),然后在NK下再过2天之后(“(8°/80%)(+2dNK)”)或在NK下再过7天之后(“(8°/80%)(+7dNK)”)或在NK下再过4周之后(“(8°/80%)(+4wNK)”)确定经如此固化的膜的硬度。在标准气候下固化的第一层膜上在2个月之后确定作为脆性量度的碎裂倾向(在表中用“碎裂倾向”表示),方法是使用锥子通过以约45°的角度倾斜挤压从膜上剥离碎屑。如果没有破裂膜块的任何脱离碎片,碎裂倾向被评价为“无”。否则,根据在用于刨去碎屑的刀尖的压力下从膜上剥落碎块的容易程度,用“弱”、“中等”或“强”表示。
结果列于表2至4中。
表2:实施例6和对比实施例7至10的组成和性能。
“n.m.”表示“不可测量”,因为膜有粘性;表示“硬度”;
表3:实施例12和对比实施例11和13至16的组成和性能。
“l.”表示“轻微”;“schw.”表示“弱”;“s.schw.”表示“极弱”;表示“硬度”;“Vergl.”表示“对比”
表4:实施例18、20和22和对比实施例17、19和21的组成和性能。
“weiss”表示标记为白色;“schw.”表示“弱”;“s.schw.”表示“极弱”;表示“硬度”;“Vergl.”表示“对比”。
Claims (15)
1.环氧树脂组合物,其包含
a)至少一种环氧树脂,和
b)至少一种适合用于固化环氧树脂的固化剂,其包含式(I)的胺,
2.根据权利要求1所述的环氧树脂组合物,其特征在于,所述固化剂还包含至少一种多胺,所述多胺具有至少三个对环氧基团有反应性的胺氢。
3.根据权利要求2所述的环氧树脂组合物,其特征在于,所述多胺选自1,3-戊二胺、1,5-二氨基-2-甲基戊烷、2-丁基-2-乙基-1,5-戊二胺、1,6-己二胺、2,2,4-和2,4,4-三甲基六亚甲基二胺、1,12-十二烷二胺、1,3-二氨基环己烷、双-(4-氨基环己基)甲烷、双-(4-氨基-3-甲基环己基)甲烷、1-氨基-3-氨基甲基-3,5,5-三甲基环己烷、1,3-双-(氨基甲基)环己烷、1,3-双-(氨基甲基)苯、双-六亚甲基三胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、五亚乙基六胺、二亚丙基三胺、N-(2-氨基乙基)-1,3-丙二胺、N,N’-双(3-氨基丙基)乙二胺、分子量为200至500g/mol的聚氧化亚烷基二胺和聚氧化亚烷基三胺、聚酰胺基胺、腰果酚改性胺、所述多胺的伯氨基上完全或部分烷基化的化合物和所述多胺与环氧化物和环氧树脂的加合物。
4.根据权利要求2所述的环氧树脂组合物,其特征在于,所述多胺选自具有5至7个亚乙基胺单元的聚亚乙基多胺。
5.根据权利要求2或3所述的环氧树脂组合物,其特征在于,所述多胺具有至少一个仲氨基。
6.根据权利要求2至4任一项所述的环氧树脂组合物,其特征在于,式(I)的胺的对环氧基团有反应性的胺氢的数目与多胺的对环氧基团有反应性的胺氢的数目的比例在0.05至5的范围内。
7.根据权利要求2至4任一项所述的环氧树脂组合物,其特征在于,式(I)的胺和多胺的重量比例为0.2至2。
8.根据权利要求1至4任一项所述的环氧树脂组合物,其特征在于,非结合性稀释剂在固化剂中的含量小于25重量%。
9.根据权利要求1至4任一项所述的环氧树脂组合物,其特征在于,环氧树脂为基于双酚的液体树脂。
10.根据权利要求1至4任一项所述的环氧树脂组合物,其特征在于,其还包含至少一种具有至少一个环氧基团的反应性稀释剂。
11.根据权利要求1至4任一项所述的环氧树脂组合物,其特征在于,其为由如下组成的双组分组合物
(i)包含至少一种环氧树脂的树脂组分,和
(ii)包含所述固化剂的固化剂组分。
12.通过固化根据权利要求1至11任一项所述的组合物而获得的经固化的组合物。
13.根据权利要求1至11任一项所述的环氧树脂组合物作为涂料的用途。
14.通过根据权利要求13所述的用途获得的制品。
15.用于固化环氧树脂的固化剂,其包含式(I)的胺,
以及至少一种多胺,所述多胺具有至少三个对环氧基团有反应性的胺氢。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11174275.5 | 2011-07-15 | ||
EP11174275A EP2546230A1 (de) | 2011-07-15 | 2011-07-15 | Emissionsarmer Härter für Epoxidharze |
PCT/EP2012/063378 WO2013010842A1 (de) | 2011-07-15 | 2012-07-09 | Emissionsarmer härter für epoxidharze |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103649042A CN103649042A (zh) | 2014-03-19 |
CN103649042B true CN103649042B (zh) | 2016-01-27 |
Family
ID=46489229
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201280034517.1A Active CN103649042B (zh) | 2011-07-15 | 2012-07-09 | 用于环氧树脂的低排放固化剂 |
Country Status (7)
Country | Link |
---|---|
US (1) | US9212287B2 (zh) |
EP (2) | EP2546230A1 (zh) |
JP (2) | JP2014520923A (zh) |
CN (1) | CN103649042B (zh) |
ES (1) | ES2640759T3 (zh) |
RU (1) | RU2613326C2 (zh) |
WO (1) | WO2013010842A1 (zh) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8729213B2 (en) * | 2011-09-23 | 2014-05-20 | Air Products And Chemicals, Inc. | Benzylated polyamine curing agents |
EP2835389A1 (de) * | 2013-08-07 | 2015-02-11 | Evonik Industries AG | Härtbare Zusammensetzung mit hoher Bruchzähigkeit |
EP2818491A1 (de) * | 2013-06-28 | 2014-12-31 | Evonik Industries AG | Härtbare Zusammensetzung mit hoher Bruchzähigkeit |
CN105408385B (zh) | 2013-02-06 | 2018-09-18 | 赢创德固赛有限公司 | 具有高断裂韧性的可硬化组合物 |
WO2015021001A1 (en) * | 2013-08-08 | 2015-02-12 | Angus Chemical Company | High performance extended pot life epoxy hardeners |
BR112016024139A2 (pt) | 2014-04-29 | 2017-08-15 | Akzo Nobel Coatings Int Bv | método para a provisão de uma superfície metálica ou concreta de uma instalação química com um revestimento, instalação química, e composição de revestimento adequada para a provisão de uma superfície metálica ou concreta de uma instalação química com um revestimento |
BR112017001482A2 (pt) * | 2014-08-05 | 2017-12-05 | Dow Global Technologies Llc | formulações adesivas 1k pu de cura dupla utilizando poliaminas encapsuladas em matriz |
RU2674676C2 (ru) * | 2014-08-13 | 2018-12-12 | Сикэ Текнолоджи Аг | Амин для низкоэмиссионных композиций эпоксидных смол |
JPWO2016143737A1 (ja) * | 2015-03-11 | 2017-12-28 | 三菱瓦斯化学株式会社 | 新規ポリアミン化合物及びその製造方法、並びに、及びこれを用いたエポキシ樹脂用硬化剤、エポキシ樹脂組成物及びエポキシ樹脂硬化物 |
CN104829861A (zh) * | 2015-05-04 | 2015-08-12 | 林登科 | 促进剂、固化剂及稀释剂之配方方法与应用在消灭胺霜及胺浮油 |
CN104893255A (zh) * | 2015-06-05 | 2015-09-09 | 安徽凯盛众普新光源有限公司 | 一种固化剂及其制备方法 |
CN104892908A (zh) * | 2015-06-05 | 2015-09-09 | 安徽凯盛众普新光源有限公司 | 一种环氧树脂固化剂及其制备方法 |
CA2990404C (en) * | 2015-06-23 | 2024-01-23 | Arkema Inc. | Latex products having polymers and polymeric adducts as quick-setting additives |
US9834625B2 (en) * | 2015-08-14 | 2017-12-05 | Kraton Polymers U.S. Llc | Amine-containing polyalkenyl coupling agents and polymers prepared therefrom |
EP3138863A1 (de) | 2015-09-01 | 2017-03-08 | Sika Technology AG | Emissionsarme epoxidharz-zusammensetzung |
EP3144335A1 (de) | 2015-09-17 | 2017-03-22 | Sika Technology AG | Amin für emissionsarme epoxidharz-zusammensetzungen |
EP3354684B1 (en) * | 2015-09-25 | 2021-11-17 | LG Chem, Ltd. | Composition for 3d printing |
EP3205681A1 (de) | 2016-02-15 | 2017-08-16 | Sika Technology AG | Härtbare zusammensetzung |
EP3205682A1 (de) | 2016-02-15 | 2017-08-16 | Sika Technology AG | Härter für emissionsarme epoxidharz-zusammensetzungen |
KR20180116366A (ko) * | 2016-02-22 | 2018-10-24 | 에보닉 데구사 게엠베하 | 벤질화 마니히 염기 경화제, 조성물, 및 방법 |
WO2018013889A1 (en) * | 2016-07-15 | 2018-01-18 | Aculon, Inc | Coated articles that demonstrate push-through electrical connectivity |
CN106380576B (zh) * | 2016-08-29 | 2018-06-26 | 湖北绿色家园材料技术股份有限公司 | 一种曼尼希碱环氧树脂固化剂 |
EP3536740A4 (en) * | 2016-11-04 | 2019-11-13 | LG Chem, Ltd. | THERMOSETTING COMPOSITION |
EP3642253B1 (de) * | 2017-06-19 | 2023-05-10 | Sika Technology AG | Blockierungsmittel für amine, latente härter und polyurethanzusammensetzungen |
JP7049152B2 (ja) * | 2018-03-29 | 2022-04-06 | 株式会社カネカ | 塗料用エポキシ樹脂組成物 |
WO2019185567A1 (en) * | 2018-03-30 | 2019-10-03 | Evonik Degussa Gmbh | Phenalkamine epoxy curing agents and epoxy resin compositions containing the same |
EP3861047B1 (de) * | 2018-10-01 | 2022-08-03 | Sika Technology AG | Härter für epoxidharze |
KR102287964B1 (ko) * | 2021-01-18 | 2021-08-09 | 이수진 | 습윤성 및 급결성이 우수한 보수제 및 이를 이용한 콘크리트 균열 보수공법 |
EP4119591A1 (de) | 2021-07-12 | 2023-01-18 | Sika Technology AG | Härter für epoxidharze |
EP4124630A1 (en) * | 2021-07-28 | 2023-02-01 | Jotun A/S | Binder composition comprising trimethylolethane triglycidyl ether |
EP4124631A1 (de) | 2021-07-28 | 2023-02-01 | Sika Technology AG | Aminhärter mit hohem erneuerbarem kohlenstoffanteil |
US20230151253A1 (en) | 2021-11-12 | 2023-05-18 | Ascend Performance Materials Operations Llc | Bhm in adhesive compositions |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1188740A2 (en) * | 2000-09-12 | 2002-03-20 | Mitsubishi Gas Chemical Company, Inc. | Amino compound and process for producing the same |
CN1551910A (zh) * | 2001-09-05 | 2004-12-01 | ������ѧ��ʽ���� | 气体阻隔性层压制品用粘合剂和层压膜 |
CN102066452A (zh) * | 2008-06-13 | 2011-05-18 | Sika技术股份公司 | 具有降低的发白的多胺及其作为环氧树脂的固化剂的用途 |
EP2336213A1 (de) * | 2009-12-08 | 2011-06-22 | Sika Technology AG | Niedrigviskose Epoxidharz-Zusammensetzung mit geringem Blushing |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3634316A (en) * | 1968-08-23 | 1972-01-11 | Showa Denko Kk | Sulfur-vulcanizable natural and synthetic rubbery polymers containing xylylene diamines as antiozonants |
US3597149A (en) * | 1969-04-29 | 1971-08-03 | Showa Denko Kk | Inhibition of gas-fume fading of dyed cellulose acetate material |
JPS4917418B1 (zh) * | 1970-12-09 | 1974-04-30 | ||
GB1422224A (en) * | 1973-11-05 | 1976-01-21 | Showa Denko Kk | Gas fading inhibitor for polyurethanes |
US4308085A (en) * | 1980-07-28 | 1981-12-29 | Jenoptik Jena Gmbh | Process for the preparation of high molecular thermoplastic epoxide-amine-polyadducts |
JPS6134017A (ja) * | 1984-07-27 | 1986-02-18 | Mitsui Toatsu Chem Inc | 熱硬化性組成物 |
JPH1160680A (ja) * | 1997-08-20 | 1999-03-02 | Nagase Chiba Kk | ポリアミン樹脂及びその製造方法 |
US8168296B2 (en) | 2007-02-07 | 2012-05-01 | Air Products And Chemicals, Inc. | Benzylated polyalkylene polyamines and uses thereof |
US8731210B2 (en) | 2009-09-21 | 2014-05-20 | Mediatek Inc. | Audio processing methods and apparatuses utilizing the same |
-
2011
- 2011-07-15 EP EP11174275A patent/EP2546230A1/de not_active Withdrawn
-
2012
- 2012-07-09 US US14/125,672 patent/US9212287B2/en not_active Expired - Fee Related
- 2012-07-09 EP EP12733490.2A patent/EP2731927B1/de active Active
- 2012-07-09 WO PCT/EP2012/063378 patent/WO2013010842A1/de active Application Filing
- 2012-07-09 JP JP2014519518A patent/JP2014520923A/ja not_active Ceased
- 2012-07-09 CN CN201280034517.1A patent/CN103649042B/zh active Active
- 2012-07-09 RU RU2013151135A patent/RU2613326C2/ru active
- 2012-07-09 ES ES12733490.2T patent/ES2640759T3/es active Active
-
2016
- 2016-05-06 JP JP2016093404A patent/JP6294383B2/ja active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1188740A2 (en) * | 2000-09-12 | 2002-03-20 | Mitsubishi Gas Chemical Company, Inc. | Amino compound and process for producing the same |
CN1551910A (zh) * | 2001-09-05 | 2004-12-01 | ������ѧ��ʽ���� | 气体阻隔性层压制品用粘合剂和层压膜 |
CN102066452A (zh) * | 2008-06-13 | 2011-05-18 | Sika技术股份公司 | 具有降低的发白的多胺及其作为环氧树脂的固化剂的用途 |
EP2336213A1 (de) * | 2009-12-08 | 2011-06-22 | Sika Technology AG | Niedrigviskose Epoxidharz-Zusammensetzung mit geringem Blushing |
Non-Patent Citations (1)
Title |
---|
Uber Derivate von m-Xylylen-diamin;von Paul Ruggli等;《Helvetica Chimica Acta》;19470101;第30卷;第1846页第4段 * |
Also Published As
Publication number | Publication date |
---|---|
RU2013151135A (ru) | 2015-08-27 |
RU2613326C2 (ru) | 2017-03-16 |
EP2731927A1 (de) | 2014-05-21 |
JP2014520923A (ja) | 2014-08-25 |
US9212287B2 (en) | 2015-12-15 |
EP2731927B1 (de) | 2017-07-05 |
ES2640759T3 (es) | 2017-11-06 |
EP2546230A1 (de) | 2013-01-16 |
US20140107313A1 (en) | 2014-04-17 |
JP6294383B2 (ja) | 2018-03-14 |
JP2016169390A (ja) | 2016-09-23 |
WO2013010842A1 (de) | 2013-01-24 |
CN103649042A (zh) | 2014-03-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103649042B (zh) | 用于环氧树脂的低排放固化剂 | |
RU2725889C2 (ru) | Праймер или адгезив на основе эпоксидной смолы холодного отверждения | |
CN104854077B (zh) | 用于低排放环氧树脂产品的胺 | |
CN103874717A (zh) | 用于环氧树脂涂料的固化剂 | |
CN104884496A (zh) | 用于低排放环氧树脂产品的固化剂 | |
CN103930462A (zh) | 用于环氧树脂涂料的固化剂 | |
CN105939992B (zh) | 用于低排放环氧树脂产物的胺 | |
CN103649161B (zh) | 用于环氧树脂的固化剂 | |
CN103917573B (zh) | 用于环氧树脂的具有芳族氨基的固化剂 | |
CN107922585A (zh) | 低排放环氧树脂组合物 | |
AU2015303289A1 (en) | Amine for low-emission epoxy resin compositions | |
CN104870509A (zh) | 用于低排放环氧树脂产品的固化剂 | |
CN108699220A (zh) | 低排放环氧树脂组合物的固化剂 | |
US20170226278A1 (en) | Amine for low-emission epoxy resin compositions | |
CN111566142A (zh) | 用于涂覆目的的环氧树脂组合物 | |
US10662280B2 (en) | Amine for low-emission epoxy resin compositions | |
CN103930460B (zh) | 用于环氧树脂的具有吡啶基团的固化剂 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160127 |