WO2024027960A1 - Epoxy resin composition with bio-based granular material - Google Patents
Epoxy resin composition with bio-based granular material Download PDFInfo
- Publication number
- WO2024027960A1 WO2024027960A1 PCT/EP2023/059067 EP2023059067W WO2024027960A1 WO 2024027960 A1 WO2024027960 A1 WO 2024027960A1 EP 2023059067 W EP2023059067 W EP 2023059067W WO 2024027960 A1 WO2024027960 A1 WO 2024027960A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bis
- epoxy resin
- weight
- resin composition
- amine
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 142
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 101
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 98
- 239000008187 granular material Substances 0.000 title claims abstract description 44
- 229920005989 resin Polymers 0.000 claims abstract description 56
- 239000011347 resin Substances 0.000 claims abstract description 56
- 239000004848 polyfunctional curative Substances 0.000 claims abstract description 44
- 238000000576 coating method Methods 0.000 claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 21
- 229920005610 lignin Polymers 0.000 claims abstract description 17
- 239000004593 Epoxy Substances 0.000 claims abstract description 16
- 239000002245 particle Substances 0.000 claims abstract description 14
- 150000001412 amines Chemical group 0.000 claims description 51
- -1 polyoxypropylene Polymers 0.000 claims description 20
- 238000002156 mixing Methods 0.000 claims description 19
- 240000007817 Olea europaea Species 0.000 claims description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 15
- 239000011248 coating agent Substances 0.000 claims description 15
- 239000010426 asphalt Substances 0.000 claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 13
- 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 12
- ACYBVNYNIZTUIL-UHFFFAOYSA-N n'-benzylethane-1,2-diamine Chemical compound NCCNCC1=CC=CC=C1 ACYBVNYNIZTUIL-UHFFFAOYSA-N 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 11
- 239000002689 soil Substances 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 9
- 239000011256 inorganic filler Substances 0.000 claims description 8
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 8
- 239000006004 Quartz sand Substances 0.000 claims description 7
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000007789 sealing Methods 0.000 claims description 7
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 7
- 244000226021 Anacardium occidentale Species 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 235000020226 cashew nut Nutrition 0.000 claims description 6
- 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 claims description 5
- 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 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 5
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 5
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 5
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000004575 stone Substances 0.000 claims description 5
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 4
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 claims description 4
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 claims description 4
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 claims description 4
- 244000068645 Carya illinoensis Species 0.000 claims description 4
- 235000009025 Carya illinoensis Nutrition 0.000 claims description 4
- 240000007049 Juglans regia Species 0.000 claims description 4
- 235000009496 Juglans regia Nutrition 0.000 claims description 4
- DPNYVVLIXCRDQZ-UHFFFAOYSA-N [5-(aminomethyl)-2-bicyclo[2.2.1]heptanyl]methanamine [6-(aminomethyl)-2-bicyclo[2.2.1]heptanyl]methanamine Chemical compound NCC1CC2CC1CC2CN.NCC1CC2CC(CN)C1C2 DPNYVVLIXCRDQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 claims description 4
- 229960005323 phenoxyethanol Drugs 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 235000020234 walnut Nutrition 0.000 claims description 4
- NDXNCTAJOQSKIO-UHFFFAOYSA-N 2-butyl-2-ethylpentane-1,5-diamine Chemical compound CCCCC(CC)(CN)CCCN NDXNCTAJOQSKIO-UHFFFAOYSA-N 0.000 claims description 3
- YQRCJEREOOTZMX-UHFFFAOYSA-N [3-[(benzylamino)methyl]phenyl]methanamine Chemical compound NCC1=CC=CC(CNCC=2C=CC=CC=2)=C1 YQRCJEREOOTZMX-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229920006272 aromatic hydrocarbon resin Polymers 0.000 claims description 3
- SDYAGGMEBLMHCR-UHFFFAOYSA-N n'-(furan-2-ylmethyl)ethane-1,2-diamine Chemical compound NCCNCC1=CC=CO1 SDYAGGMEBLMHCR-UHFFFAOYSA-N 0.000 claims description 3
- UZXQTTITYSXQQH-UHFFFAOYSA-N n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound NCCNCC1CCCO1 UZXQTTITYSXQQH-UHFFFAOYSA-N 0.000 claims description 3
- OMKZWUPRGQMQJC-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]propane-1,3-diamine Chemical compound CN(C)CCCNCCCN OMKZWUPRGQMQJC-UHFFFAOYSA-N 0.000 claims description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 244000144725 Amygdalus communis Species 0.000 claims description 2
- 235000011437 Amygdalus communis Nutrition 0.000 claims description 2
- 244000144730 Amygdalus persica Species 0.000 claims description 2
- 244000205479 Bertholletia excelsa Species 0.000 claims description 2
- 235000012284 Bertholletia excelsa Nutrition 0.000 claims description 2
- 244000060011 Cocos nucifera Species 0.000 claims description 2
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 2
- 240000009226 Corylus americana Species 0.000 claims description 2
- 235000001543 Corylus americana Nutrition 0.000 claims description 2
- 235000007466 Corylus avellana Nutrition 0.000 claims description 2
- 235000018330 Macadamia integrifolia Nutrition 0.000 claims description 2
- 240000000912 Macadamia tetraphylla Species 0.000 claims description 2
- 235000003800 Macadamia tetraphylla Nutrition 0.000 claims description 2
- 240000006711 Pistacia vera Species 0.000 claims description 2
- 235000003447 Pistacia vera Nutrition 0.000 claims description 2
- 244000018633 Prunus armeniaca Species 0.000 claims description 2
- 235000009827 Prunus armeniaca Nutrition 0.000 claims description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 claims description 2
- 244000299461 Theobroma cacao Species 0.000 claims description 2
- 235000009470 Theobroma cacao Nutrition 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 235000020224 almond Nutrition 0.000 claims description 2
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims description 2
- 235000013399 edible fruits Nutrition 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 235000020233 pistachio Nutrition 0.000 claims description 2
- 239000004576 sand Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 7
- 125000003277 amino group Chemical group 0.000 abstract description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 9
- 239000000835 fiber Substances 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000003700 epoxy group Chemical group 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 229920000768 polyamine Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- ZENOXNGFMSCLLL-UHFFFAOYSA-N vanillyl alcohol Chemical compound COC1=CC(CO)=CC=C1O ZENOXNGFMSCLLL-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 239000004568 cement Substances 0.000 description 5
- 239000004567 concrete Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- 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 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 229940106691 bisphenol a Drugs 0.000 description 4
- 239000011083 cement mortar Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000010903 husk Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 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 4
- 229920003986 novolac Polymers 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000004006 olive oil Substances 0.000 description 4
- 235000008390 olive oil Nutrition 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920003319 Araldite® Polymers 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- 239000010428 baryte Substances 0.000 description 3
- 229910052601 baryte Inorganic materials 0.000 description 3
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 3
- 239000011449 brick Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- UBDPGWZWCACARC-UHFFFAOYSA-N 2,4,6-tris[[3-(dimethylamino)propylamino]methyl]phenol Chemical compound CN(C)CCCNCC1=CC(CNCCCN(C)C)=C(O)C(CNCCCN(C)C)=C1 UBDPGWZWCACARC-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 2
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KWOIWTRRPFHBSI-UHFFFAOYSA-N 4-[2-[3-[2-(4-aminophenyl)propan-2-yl]phenyl]propan-2-yl]aniline Chemical compound C=1C=CC(C(C)(C)C=2C=CC(N)=CC=2)=CC=1C(C)(C)C1=CC=C(N)C=C1 KWOIWTRRPFHBSI-UHFFFAOYSA-N 0.000 description 2
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 description 2
- HESXPOICBNWMPI-UHFFFAOYSA-N 4-[2-[4-[2-(4-aminophenyl)propan-2-yl]phenyl]propan-2-yl]aniline Chemical compound C=1C=C(C(C)(C)C=2C=CC(N)=CC=2)C=CC=1C(C)(C)C1=CC=C(N)C=C1 HESXPOICBNWMPI-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 2
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000003677 Sheet moulding compound Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [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
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000011151 fibre-reinforced plastic Substances 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 235000013980 iron oxide Nutrition 0.000 description 2
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 230000005923 long-lasting effect Effects 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
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 235000014571 nuts Nutrition 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000011505 plaster Substances 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000005932 reductive alkylation reaction Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- RZUNIXAGSKNOIB-HSFFGMMNSA-N (1z,3e)-cyclododeca-1,3-diene Chemical compound C1CCCC\C=C/C=C/CCC1 RZUNIXAGSKNOIB-HSFFGMMNSA-N 0.000 description 1
- XMNDMAQKWSQVOV-UHFFFAOYSA-N (2-methylphenyl) diphenyl phosphate Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 XMNDMAQKWSQVOV-UHFFFAOYSA-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
- BGGGMYCMZTXZBY-UHFFFAOYSA-N (3-hydroxyphenyl) phosphono hydrogen phosphate Chemical compound OC1=CC=CC(OP(O)(=O)OP(O)(O)=O)=C1 BGGGMYCMZTXZBY-UHFFFAOYSA-N 0.000 description 1
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 1
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- YVVYMSXDQGDASK-UHFFFAOYSA-N 1,2,3-tribromo-4-[2-(2,3,4-tribromophenoxy)ethoxy]benzene Chemical compound BrC1=C(Br)C(Br)=CC=C1OCCOC1=CC=C(Br)C(Br)=C1Br YVVYMSXDQGDASK-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
- YUAPUIKGYCAHGM-UHFFFAOYSA-N 1,2-dibromo-3-(2,3-dibromopropoxy)propane Chemical compound BrCC(Br)COCC(Br)CBr YUAPUIKGYCAHGM-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- WZRRRFSJFQTGGB-UHFFFAOYSA-N 1,3,5-triazinane-2,4,6-trithione Chemical compound S=C1NC(=S)NC(=S)N1 WZRRRFSJFQTGGB-UHFFFAOYSA-N 0.000 description 1
- NZUPFZNVGSWLQC-UHFFFAOYSA-N 1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound BrCC(Br)CN1C(=O)N(CC(Br)CBr)C(=O)N(CC(Br)CBr)C1=O NZUPFZNVGSWLQC-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-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
- ZPANWZBSGMDWON-UHFFFAOYSA-N 1-[(2-hydroxynaphthalen-1-yl)methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 ZPANWZBSGMDWON-UHFFFAOYSA-N 0.000 description 1
- XPNHFNJYPSXRRG-UHFFFAOYSA-N 1-[2-(2-aminobutoxy)ethoxy]butan-2-amine Chemical compound CCC(N)COCCOCC(N)CC XPNHFNJYPSXRRG-UHFFFAOYSA-N 0.000 description 1
- VTAMQDCTAXRISX-UHFFFAOYSA-N 1-[2-(2-aminopropoxy)ethoxy]propan-2-amine Chemical compound CC(N)COCCOCC(C)N VTAMQDCTAXRISX-UHFFFAOYSA-N 0.000 description 1
- UOWSVNMPHMJCBZ-UHFFFAOYSA-N 1-[2-(2-butoxypropoxy)propoxy]butane Chemical compound CCCCOCC(C)OCC(C)OCCCC UOWSVNMPHMJCBZ-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-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
- WDQDOALSJXWMIU-UHFFFAOYSA-N 1-n-(1-aminopentan-3-yl)pentane-1,3-diamine Chemical compound CCC(N)CCNC(CC)CCN WDQDOALSJXWMIU-UHFFFAOYSA-N 0.000 description 1
- QEXJEJPSPOSZIS-UHFFFAOYSA-N 1-n-benzylpropane-1,2-diamine Chemical compound CC(N)CNCC1=CC=CC=C1 QEXJEJPSPOSZIS-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
- BIZBXUGHSYSUGJ-UHFFFAOYSA-N 1-propan-2-ylbiphenylene Chemical group C12=CC=CC=C2C2=C1C=CC=C2C(C)C BIZBXUGHSYSUGJ-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- VGKUQBORKKSJMG-UHFFFAOYSA-N 2,2,6-trimethylcyclohexane-1,4-diamine Chemical compound CC1CC(N)CC(C)(C)C1N VGKUQBORKKSJMG-UHFFFAOYSA-N 0.000 description 1
- CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 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
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
- BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 description 1
- BLPURQSRCDKZNX-UHFFFAOYSA-N 2,4,6-tris(oxiran-2-ylmethoxy)-1,3,5-triazine Chemical compound C1OC1COC(N=C(OCC1OC1)N=1)=NC=1OCC1CO1 BLPURQSRCDKZNX-UHFFFAOYSA-N 0.000 description 1
- SCSMZMBYJMIJTK-UHFFFAOYSA-N 2,4,9,10,11-pentaoxa-5,8-diaza-1lambda5,3lambda5-diphosphatricyclo[6.1.1.13,5]undecane 1,3-dioxide Chemical compound O1P(=O)(O2)ON2CCN2OP1(=O)O2 SCSMZMBYJMIJTK-UHFFFAOYSA-N 0.000 description 1
- IVJXXQSXKSRPIL-UHFFFAOYSA-N 2,4-bis[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=C(O)C(CN(C)C)=C1 IVJXXQSXKSRPIL-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
- VUENIEFVRKDJAS-UHFFFAOYSA-N 2,6-bis[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=CC(CN(C)C)=C1O VUENIEFVRKDJAS-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- JPEGUDKOYOIOOP-UHFFFAOYSA-N 2-(hexoxymethyl)oxirane Chemical compound CCCCCCOCC1CO1 JPEGUDKOYOIOOP-UHFFFAOYSA-N 0.000 description 1
- QNYBOILAKBSWFG-UHFFFAOYSA-N 2-(phenylmethoxymethyl)oxirane Chemical compound C1OC1COCC1=CC=CC=C1 QNYBOILAKBSWFG-UHFFFAOYSA-N 0.000 description 1
- RJNVSQLNEALZLC-UHFFFAOYSA-N 2-[(2-methoxyphenoxy)methyl]oxirane Chemical compound COC1=CC=CC=C1OCC1OC1 RJNVSQLNEALZLC-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
- MSWONMWDQHSVIY-UHFFFAOYSA-N 2-[(4-dodecylphenoxy)methyl]oxirane Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1OCC1OC1 MSWONMWDQHSVIY-UHFFFAOYSA-N 0.000 description 1
- AVWGFHZLPMLKBL-UHFFFAOYSA-N 2-[(4-methoxyphenoxy)methyl]oxirane Chemical compound C1=CC(OC)=CC=C1OCC1OC1 AVWGFHZLPMLKBL-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
- AVKQYWUBGXNBCW-UHFFFAOYSA-N 2-[(4-nonylphenoxy)methyl]oxirane Chemical compound C1=CC(CCCCCCCCC)=CC=C1OCC1OC1 AVKQYWUBGXNBCW-UHFFFAOYSA-N 0.000 description 1
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-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
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 1
- HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 description 1
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-UHFFFAOYSA-N 0.000 description 1
- CUZKCNWZBXLAJX-UHFFFAOYSA-N 2-phenylmethoxyethanol Chemical compound OCCOCC1=CC=CC=C1 CUZKCNWZBXLAJX-UHFFFAOYSA-N 0.000 description 1
- ZDRSNHRWLQQICP-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 ZDRSNHRWLQQICP-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- RKSBPFMNOJWYSB-UHFFFAOYSA-N 3,3-Bis(4-hydroxyphenyl)pentane Chemical compound C=1C=C(O)C=CC=1C(CC)(CC)C1=CC=C(O)C=C1 RKSBPFMNOJWYSB-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
- JOLVYUIAMRUBRK-AOSYACOCSA-N 3-(8,11,14-Pentadecatrienyl)phenol Chemical compound OC1=CC=CC(CCCCCCC\C=C\C\C=C\CC=C)=C1 JOLVYUIAMRUBRK-AOSYACOCSA-N 0.000 description 1
- POTQBGGWSWSMCX-UHFFFAOYSA-N 3-[2-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCCN POTQBGGWSWSMCX-UHFFFAOYSA-N 0.000 description 1
- ANOPCGQVRXJHHD-UHFFFAOYSA-N 3-[3-(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]propan-1-amine Chemical compound C1OC(CCCN)OCC21COC(CCCN)OC2 ANOPCGQVRXJHHD-UHFFFAOYSA-N 0.000 description 1
- YOOSAIJKYCBPFW-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)butoxy]propan-1-amine Chemical compound NCCCOCCCCOCCCN YOOSAIJKYCBPFW-UHFFFAOYSA-N 0.000 description 1
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 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
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- MLDIQALUMKMHCC-UHFFFAOYSA-N 4,4-Bis(4-hydroxyphenyl)heptane Chemical compound C=1C=C(O)C=CC=1C(CCC)(CCC)C1=CC=C(O)C=C1 MLDIQALUMKMHCC-UHFFFAOYSA-N 0.000 description 1
- DYIZJUDNMOIZQO-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O DYIZJUDNMOIZQO-UHFFFAOYSA-N 0.000 description 1
- KOGSPLLRMRSADR-UHFFFAOYSA-N 4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine Chemical compound CC(C)(N)C1CCC(C)(N)CC1 KOGSPLLRMRSADR-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- JHCBFGGESJQAIQ-UHFFFAOYSA-N 4-[(4-amino-3,5-dimethylcyclohexyl)methyl]-2,6-dimethylcyclohexan-1-amine Chemical compound C1C(C)C(N)C(C)CC1CC1CC(C)C(N)C(C)C1 JHCBFGGESJQAIQ-UHFFFAOYSA-N 0.000 description 1
- OZTBUYKEBWNOKR-UHFFFAOYSA-N 4-[(4-amino-3-ethyl-5-methylcyclohexyl)methyl]-2-ethyl-6-methylcyclohexan-1-amine Chemical compound C1C(C)C(N)C(CC)CC1CC1CC(CC)C(N)C(C)C1 OZTBUYKEBWNOKR-UHFFFAOYSA-N 0.000 description 1
- HCJLTNJVGXHKTN-UHFFFAOYSA-N 4-[(4-amino-3-ethylcyclohexyl)methyl]-2-ethylcyclohexan-1-amine Chemical compound C1CC(N)C(CC)CC1CC1CC(CC)C(N)CC1 HCJLTNJVGXHKTN-UHFFFAOYSA-N 0.000 description 1
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 1
- AZZWZMUXHALBCQ-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CC=2C=C(C)C(O)=C(C)C=2)=C1 AZZWZMUXHALBCQ-UHFFFAOYSA-N 0.000 description 1
- MIFGCULLADMRTF-UHFFFAOYSA-N 4-[(4-hydroxy-3-methylphenyl)methyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(CC=2C=C(C)C(O)=CC=2)=C1 MIFGCULLADMRTF-UHFFFAOYSA-N 0.000 description 1
- XWCCUTVLIUTJHB-UHFFFAOYSA-N 4-[(4-hydroxynaphthalen-1-yl)methyl]naphthalen-1-ol Chemical compound C12=CC=CC=C2C(O)=CC=C1CC1=CC=C(O)C2=CC=CC=C12 XWCCUTVLIUTJHB-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
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- OBZFGWBLZXIBII-UHFFFAOYSA-N 4-[3-(4-hydroxy-3,5-dimethylphenyl)-3-methylbutyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CCC(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 OBZFGWBLZXIBII-UHFFFAOYSA-N 0.000 description 1
- NIRYBKWMEWFDPM-UHFFFAOYSA-N 4-[3-(4-hydroxyphenyl)-3-methylbutyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)CCC1=CC=C(O)C=C1 NIRYBKWMEWFDPM-UHFFFAOYSA-N 0.000 description 1
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004114 Ammonium polyphosphate Substances 0.000 description 1
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920000459 Nitrile rubber Polymers 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 compound 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
- 241000207836 Olea <angiosperm> Species 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical group C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 239000004823 Reactive adhesive Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- WOURXYYHORRGQO-UHFFFAOYSA-N Tri(3-chloropropyl) phosphate Chemical compound ClCCCOP(=O)(OCCCCl)OCCCCl WOURXYYHORRGQO-UHFFFAOYSA-N 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 244000263375 Vanilla tahitensis Species 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PYXVXICPPTUQQZ-BFHYXJOUSA-N [(3R,4R,5S)-4-acetamido-5-azaniumyl-3-pentan-3-yloxycyclohexen-1-yl]-methoxyphosphinate Chemical compound CCC(CC)O[C@@H]1C=C(P([O-])(=O)OC)C[C@H]([NH3+])[C@H]1NC(C)=O PYXVXICPPTUQQZ-BFHYXJOUSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-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
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- SXQXMCWCWVCFPC-UHFFFAOYSA-N aluminum;potassium;dioxido(oxo)silane Chemical compound [Al+3].[K+].[O-][Si]([O-])=O.[O-][Si]([O-])=O SXQXMCWCWVCFPC-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 1
- 229920001276 ammonium polyphosphate Polymers 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000000035 biogenic effect Effects 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
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- IUTYMBRQELGIRS-UHFFFAOYSA-N boric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OB(O)O.NC1=NC(N)=NC(N)=N1 IUTYMBRQELGIRS-UHFFFAOYSA-N 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- UGQQAJOWXNCOPY-UHFFFAOYSA-N dechlorane plus Chemical compound C12CCC3C(C4(Cl)Cl)(Cl)C(Cl)=C(Cl)C4(Cl)C3CCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl UGQQAJOWXNCOPY-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-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
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- IWBOPFCKHIJFMS-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl) ether Chemical compound NCCOCCOCCN IWBOPFCKHIJFMS-UHFFFAOYSA-N 0.000 description 1
- 239000004794 expanded polystyrene Substances 0.000 description 1
- 239000004795 extruded polystyrene foam 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
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000010881 fly ash Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 239000002241 glass-ceramic Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000010438 granite Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- PBBGSZCBWVPOOL-UHFFFAOYSA-N hexestrol Chemical compound C=1C=C(O)C=CC=1C(CC)C(CC)C1=CC=C(O)C=C1 PBBGSZCBWVPOOL-UHFFFAOYSA-N 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229920002681 hypalon Polymers 0.000 description 1
- 229960002479 isosorbide Drugs 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- GBTLMWXVQMOHRC-UHFFFAOYSA-N n'-(1-aminopentan-3-yl)-2-methylpentane-1,5-diamine Chemical compound NCCC(CC)NCCCC(C)CN GBTLMWXVQMOHRC-UHFFFAOYSA-N 0.000 description 1
- DTSDBGVDESRKKD-UHFFFAOYSA-N n'-(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCNCCN DTSDBGVDESRKKD-UHFFFAOYSA-N 0.000 description 1
- IRYWPHGCDAOHJJ-UHFFFAOYSA-N n'-(3-aminopropyl)-2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCNCCCN IRYWPHGCDAOHJJ-UHFFFAOYSA-N 0.000 description 1
- IZBVZYNGZBUGAZ-UHFFFAOYSA-N n'-[2-(benzylamino)ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCC1=CC=CC=C1 IZBVZYNGZBUGAZ-UHFFFAOYSA-N 0.000 description 1
- XXOQMYGARAONKF-UHFFFAOYSA-N n'-[2-[2-(benzylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCC1=CC=CC=C1 XXOQMYGARAONKF-UHFFFAOYSA-N 0.000 description 1
- FOJGLBMCIUPMNG-UHFFFAOYSA-N n'-[2-[benzyl-[2-(benzylamino)ethyl]amino]ethyl]ethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCNCCN)CCNCC1=CC=CC=C1 FOJGLBMCIUPMNG-UHFFFAOYSA-N 0.000 description 1
- AZZHHQHXUXFIJP-UHFFFAOYSA-N n,n'-bis(1-aminopentan-3-yl)-2-methylpentane-1,5-diamine Chemical compound NCCC(CC)NCCCC(C)CNC(CC)CCN AZZHHQHXUXFIJP-UHFFFAOYSA-N 0.000 description 1
- GMYKINUEQHRTNE-UHFFFAOYSA-N n-[[3-(aminomethyl)-2-hexylphenyl]methyl]ethanamine Chemical compound CCCCCCC1=C(CN)C=CC=C1CNCC GMYKINUEQHRTNE-UHFFFAOYSA-N 0.000 description 1
- MDBDINBDBKSVKE-UHFFFAOYSA-N n-[[3-(aminomethyl)phenyl]methyl]-2-phenylethanamine Chemical compound NCC1=CC=CC(CNCCC=2C=CC=CC=2)=C1 MDBDINBDBKSVKE-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- UGFMBZYKVQSQFX-UHFFFAOYSA-N para-methoxy-n-methylamphetamine Chemical compound CNC(C)CC1=CC=C(OC)C=C1 UGFMBZYKVQSQFX-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 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
- 150000003013 phosphoric acid derivatives Chemical class 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 239000011388 polymer cement concrete Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged 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
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 238000005029 sieve analysis Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 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
- NMWCVZCSJHJYFW-UHFFFAOYSA-M sodium;3,5-dichloro-2-hydroxybenzenesulfonate Chemical compound [Na+].OC1=C(Cl)C=C(Cl)C=C1S([O-])(=O)=O NMWCVZCSJHJYFW-UHFFFAOYSA-M 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000000600 sorbitol Substances 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
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 239000011145 styrene acrylonitrile resin Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ALVKHVFHUNINLV-UHFFFAOYSA-N tert-butyl 2-bromo-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1C=C(Br)S2 ALVKHVFHUNINLV-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229920002397 thermoplastic olefin Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-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
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 229910052727 yttrium Inorganic materials 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
- 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
- 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
Definitions
- the invention relates to the field of cold-curing epoxy resin compositions for floor coatings.
- Epoxy resin-based floor coating products are widely used in construction. They consist of liquid resin and hardener components, which are mixed before application and then react at ambient temperatures to form a solid coating.
- floor coating products contain inorganic fillers, depending on the desired application and technical requirements. For certain applications, however, products are desired that are largely free of inorganic fillers. Alternatives to classic fillers that meet the requirements for floor coating products are therefore of great interest.
- DE 10 2008 026 266 A1 describes moldings for use as a floor or soundproofing element, which are produced by bonding ground granules from olive pits with reactive adhesives based on polyurethanes or epoxy resins.
- WO 2015/018466 describes adhesives for fastening technology, which can contain so-called biogenic fillers.
- Alkylated amines such as N-benzyl-1,2-ethanediamine are known as hardeners for epoxy resins, for example from WO 2017/037069. They enable low-emission epoxy resin coatings with beautiful surfaces.
- the object of the present invention is to provide an epoxy resin composition suitable for floor coating purposes, which contains additives that mix well and can be easily redispersed after storage, enabling optically high-quality coatings with a flawless and smooth surface.
- This task is achieved with the epoxy resin composition as described in claim 1.
- the bio-based granules contained in the composition with a lignin content of at least 10% by weight have a surprisingly low tendency to rot Settling and remains excellently redispersible even after prolonged storage and transport of the components. After curing, the composition exhibits a remarkably smooth, visually flawless surface.
- bio-based granules with no or too low lignin content are difficult or impossible to redisperse after storage, which is disadvantageous for their applicability.
- compositions which contain at least one amine of the formula (I) in the amine hardener show particularly good flow behavior of the mixed components.
- the bio-based granules in combination with the amine of formula (I) enable a particularly low viscosity and, in addition, particularly rapid curing in the cold, which means that corresponding coatings are particularly easy to process and can be walked on quickly even in cold ambient conditions.
- compositions according to the invention which are largely free of inorganic fillers, with the bio-based granules being considered as part of the organic binder.
- Such a composition also known as “unfilled”, has a reduced content of petro-based binders and thinners and is therefore particularly sustainable.
- the epoxy resin composition enables particularly sustainable floor coating systems that can be stored well before use, are easy to apply and ensure technically high-quality and long-lasting protection with a highly visually appealing appearance.
- the subject matter of the invention is an epoxy resin composition comprising
- bio-based granulate with a particle size ⁇ 200 pm and a lignin content of at least 10% by weight, preferably at least 15% by weight, the bio-based granulate being part of the resin and/or the hardener component and the content of bio-based granulate based on the entire epoxy resin composition is 1 to 40% by weight, preferably 2 to 30% by weight, in particular 5 to 25% by weight.
- epoxy liquid resin is a technical polyepoxide with a glass transition temperature below 25°C.
- a “primary amino group” is an amino group that is bonded to a single organic residue and carries two hydrogen atoms
- a “secondary amino group” is an amino group that is bonded to two organic residues, which can also be part of a ring, and carries a hydrogen atom
- a “tertiary amino group” is an amino group that is bonded to three organic residues, two or three of which can be part of one or more rings, and does not contain a hydrogen atom.
- amine hydrogen The hydrogen atoms of primary and secondary amino groups are referred to as “amine hydrogen”.
- Substance names beginning with “Poly” such as polyamine, polyol or polyepoxide refer to substances that formally contain two or more of the functional groups appearing in their name per molecule.
- live pit refers in particular to the residue from olive pit shells after the oil has been pressed or extracted from the olives.
- cashew nut shells in this document refer in particular to the remaining shell fragments of the cashew nuts after the cashew nut shell oil has been pressed or extracted from the hard shells.
- a “thinner” is a substance that is soluble in an epoxy resin and reduces its viscosity and is not chemically bound into the epoxy polymer during curing.
- Molecular weight is the molar mass (in grams per mole) of a molecule.
- the “average molecular weight” is the number average M n of a polydisperse mixture of oligomeric or polymeric molecules, which is usually determined using gel permeation chromatography (GPC) against polystyrene as a standard.
- room temperature A temperature of 23°C is referred to as “room temperature”.
- the resin component and the hardener component of the epoxy resin composition are preferably stored separately from one another before application of the composition.
- the resin component and the hardener component of the epoxy resin composition are therefore preferably present separately from one another.
- the separate ones Components can be stored for a period of a few months to a year or longer without losing their usability.
- the bio-based granules with a lignin content of at least 10% by weight have a particle size of ⁇ 200 pm, preferably ⁇ 100 pm.
- the particle size is preferably determined using sieve analysis as described in ASTM C136/C136M-2014.
- a particle size of more than 200 pm is disadvantageous in that it results in coatings whose surface properties have unevenness that can be clearly seen by the eye. This can be seen, for example, in Table 1 in the comparison of the composition Z-1 with Z-2 (Ref.) and Z-3 (Ref.).
- the epoxy resin composition contains 1 to 40% by weight, preferably 2 to 30% by weight, in particular 5 to 25% by weight, of bio-based granules.
- a proportion of bio-based granules of more than 40% by weight based on the total weight of the epoxy resin composition is disadvantageous in that this means that the epoxy resin composition is no longer sufficiently dispersible. This can be seen, for example, in Table 1 in the comparison of the compositions Z-1 and Z-6 to Z-8 with Z-9 (Ref.).
- the preferred ranges mentioned are advantageous in that good dispersibility of the epoxy resin composition as well as a high proportion of bio-based granules can be achieved.
- the bio-based granules preferably have a moisture content of less than 15% by weight, preferably less than 12% by weight. Such granules can be mixed particularly well into the respective component and ensure trouble-free curing of the composition
- All types of shredded wood with a lignin content of at least 10% by weight are suitable as bio-based granules.
- Preferred bio-based granules are waste products from agricultural products, in particular foods such as gels, nuts or seeds, with inedible components in the form of shells, pods or cores made of woody material with a lignin content of at least 10% by weight. This are prepared for use according to the invention and ground to the desired particle size or particle distribution and, if necessary, further treated, in particular dried or sieved.
- bio-based granulate with a lignin content of at least 10% by weight selected from the group consisting of ground olive kernels, coconut shells, almond shells, walnut shells, pecan shells, Brazil nut shells, hazelnut shells, macadamia nut shells, cashew nut shells, pistachio shells, cocoa fruit shells, apricot kernel shells, peach kernel shells and plum kernel shells .
- the bio-based granules are granules made from olive stones. This granulate is available in large quantities and of good quality and enables epoxy resin compositions with particularly good redispersibility after storage of the components and particularly good processability at cold temperatures, in particular 12 ° C.
- a suitable granulate of olive pits is preferably available from olive pit shell fragments from the production of olive oil, which are dried, ground and sieved.
- the olive kernel granules preferably have a lignin content of at least 15% by weight and an oil content of less than 3% by weight, preferably less than 1% by weight, particularly preferably less than 0.5% by weight.
- the olive stone granules preferably have a Mohs hardness of 3 to 4.
- the bio-based granules are preferably part of the resin component.
- the resin component preferably has a content of bio-based granules of 2 to 45% by weight, particularly preferably 4 to 35% by weight, in particular 6 to 30% by weight, based on the total resin component.
- the resin component of the epoxy resin composition contains at least one epoxy liquid resin.
- a suitable epoxy liquid resin is obtained in a known manner, in particular from the oxidation of the corresponding olefins or from the reaction of epichlorohydrin with the corresponding polyols, polyphenols or amines.
- Suitable epoxy liquid resins are in particular aromatic epoxy resins, in particular the glycidyl ethers of:
- bisphenol A bisphenol F or bisphenol A/F, where A stands for acetone and F for formaldehyde, which served as starting materials for the production of these bisphenols.
- A stands for acetone and F for formaldehyde, which served as starting materials for the production of these bisphenols.
- positional isomers may also be present, in particular derived from 2,4'- or 2,2'-hydroxyphenylmethane;
- Dihydroxybenzene derivatives such as resorcinol, hydroquinone or catechol;
- bisphenols or polyphenols such as bis(4-hydroxy-3-methylphenyl)methane, 2,2-bis(4-hydroxy-3-methylphenyl)propane (bisphenol C), bis(3,5-dimethyl-4-hydroxyphenyl) methane, 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3- tert-butylphenyl)propane, 2,2-bis(4-hydroxyphenyl)butane (bisphenol B), 3,3-bis(4-hydroxyphenyl)pentane, 3,4-bis(4-hydroxyphenyl)hexane, 4,4- Bis(4-hydroxyphenyl)heptane, 2,4-bis(4-hydroxyphenyl)-2-methylbutane, 2,4-bis(3,5-dimethyl-4-hydroxyphenyl)-2-methylbutane, 1,1-bis(4
- aromatic amines such as aniline, toluidine, 4-aminophenol, 4,4'-methylenediphenyldiamine, 4,4'-methylenediphenyldi-(N-methyl)amine, 4,4'-[1,4-phenylene-bis( 1-methylethylidene)]bisaniline (bisaniline-P) or 4,4'-[1,3-phenylene-bis(1-methylethylidene)]bisaniline (bisaniline-M).
- aniline toluidine
- 4-aminophenol 4,4'-methylenediphenyldiamine, 4,4'-methylenediphenyldi-(N-methyl)amine
- 4,4'-[1,4-phenylene-bis( 1-methylethylidene)]bisaniline bisaniline-P
- 4,4'-[1,3-phenylene-bis(1-methylethylidene)]bisaniline bisaniline-M
- epoxy liquid resins are aliphatic or cycloaliphatic polyepoxides, in particular
- - glycidyl ethers of saturated or unsaturated, branched or unbranched, cyclic or open-chain di-, tri- or tetrafunctional C2 to Cso alcohols, in particular ethylene glycol, propylene glycol, butylene glycol, hexanediol, octanediol, polypropylene glycols, dimethylolcyclohexane, neopentyl glycol, dibromoneopentyl glycol, castor oil, Trimethylolpropane , trimethylolethane, pentaerythrol, sorbitol or glycerin, or alkoxylated glycerin or alkoxylated trimethylolpropane;
- N-glycidyl derivative of amides or heterocyclic nitrogen bases such as triglycidyl cyanurate or triglycidyl isocyanurate, or reaction products of epichlorohydrin with hydantoin;
- olefins such as in particular vinylcylohexene, dicyclopentadiene, cyclohexadiene, cyclododecadiene, cyclododecatriene, isoprene, 1,5-hexadiene, butadiene, polybutadiene or divinylbenzene.
- epoxy liquid resins which are at least partially based on renewable raw materials, such as in particular diglycidyl ether of vanillin alcohol, diglycidyl ether of isosorbide or triglycidyl ether of glycerol, as well as bisphenol A diglycidyl ether of bio-based epichlorohydrin.
- the epoxy resin liquid resin is in particular an aromatic liquid resin based on a bisphenol or novolak, in particular with an average epoxy equivalent weight in the range from 156 to 210 g/eq.
- Particularly suitable is a bisphenol A diglycidyl ether and/or bisphenol F diglycidyl ether, such as those commercially available, for example, as Araldite® GY 250, Araldite® PY 304, Araldite® GY 282 (from Huntsman) or DERTM 331 or DERTM 330 (from Dow ) or EponTM Resin 828 (from Hexion) are available.
- Such liquid resins have a low viscosity for epoxy resins and enable rapid curing and high hardness.
- a bisphenol A diglycidyl ether from the reaction of bisphenol A with bio-based epichlorohydrin is also particularly preferred. This enables particularly sustainable epoxy resin compositions.
- phenol-formaldehyde novolak glycidyl ethers in particular with an average functionality in the range from 2.3 to 4, preferably 2.5 to 3. They can contain portions of other epoxy resins, in particular bisphenol A diglycidyl ether or bisphenol F diglycidyl ether.
- the resin component preferably additionally contains at least one reactive diluent containing epoxy groups, in particular 1 to 15% by weight, preferably 1.5 to 10% by weight, in particular 2 to 8% by weight, of reactive diluent containing epoxy groups, based on the total weight of the epoxy resin. Composition.
- Preferred reactive diluents containing epoxy groups are butanediol diglycidyl ether, hexanediol diglycidyl ether, trimethylolpropane di- or triglycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether, guaiacol glycidyl ether, 4-methoxyphenyl glycidyl ether, p-n-butylphenyl glycidyl ether, p-tert-butylphenyl glycidyl ether, 4-nonylphenyl glycidyl ether, 4- Dodecylphenyl glycidyl ether, vanilla glycidyl ether, cardanol glycidyl ether, Benzyl glycidyl ether, allyl glycidyl ether, butyl glycid
- Glycidyl ethers of natural alcohols in particular C12 to C14 alkyl glycidyl ethers, are particularly preferred. This results in particularly easy-to-process epoxy resin compositions.
- the resin component additionally contains portions of solid epoxy resin.
- the hardener component of the epoxy resin composition contains at least one amine hardener.
- Suitable amine hardeners are in particular aliphatic, cycloaliphatic or arylaliphatic diamines or triamines with at least 3 amine hydrogens, such as in particular
- - primary di- or triamines in particular 2, 2-dimethyl-1,3-propanediamine, 1,3-pentanediamine (DAMP), 1,5-pentanediamine, 1,5-diamino-2-methylpentane (MPMD), 2- Butyl-2-ethyl-1,5-pentanediamine (C11-neodiamine), 1,6-hexanediamine, 2,5-dimethyl-1,6-hexanediamine, 2,2(4),4-trimethylhexamethylenediamine (TMD), 1 ,7-heptanediamine,
- DAMP 1,3-pentanediamine
- MPMD 1,5-pentanediamine
- MPMD 1,5-diamino-2-methylpentane
- C11-neodiamine 2- Butyl-2-ethyl-1,5-pentanediamine
- TMD 2,2(4),4-trimethylhexamethylenediamine
- Aliphatic primary di- or triamines containing ether groups in particular bis(2-aminoethyl) ether, 3,6-dioxaoctane-1,8-diamine, 4,7-dioxadecane-1,10-diamine, 4,7-dioxadecane 2,9-diamine, 4,9-dioxadodecane-1, 12-diamine, 5,8-dioxadodecane-3, 10-diamine, 4,7,10-trioxatridecan-1, 13-diamine or higher oligomers of these diamines, Bis(3-aminopropyl)polytetrahydrofurans or other polytetrahydrofurandiamines, or polyoxyalkylenedi- or triamines, in particular the Jeffamine® D-230, D-400, D-2000, EDR-104, EDR-148, EDR-176, T-403, T-3000 or Jeffamine® T
- the amine hardener preferably contains at least one aliphatic, cycloaliphatic or arylaliphatic diamine or triamine with at least 3 amine hydrogens, in particular selected from the group consisting of 2-butyl-2-ethyl-1,5-pentanediamine (C11 - neodiamine), 2,2( 4),4-trimethylhexamethylenediamine (TMD), 1,2-diaminocyclohexane, bis(4-aminocyclohexyl)methane, isophoronediamine (IPDA), 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 2 (4)-Methyl-1,3-diaminocyclohexane, 2,5(2,6)-bis(aminomethyl)bicyclo[2.2.1]heptane (NBDA), 1,3-bis(aminomethyl)benzene (MXDA), polyoxypropyl
- the amine hardener also preferably contains 1,3-bis(aminomethyl)benzene (MXDA). This amine enables particularly rapid curing.
- MXDA 1,3-bis(aminomethyl)benzene
- the amine hardener also preferably contains 1,3-bis(aminomethyl)cyclohexane. This amine enables rapid curing and a particularly low tendency to yellowing.
- the amine hardener contains at least one amine of the formula (I),
- A represents a divalent alkylene or cycloalkylene radical with 2 to 8 carbon atoms
- Y represents an optionally substituted phenyl radical with 6 to 12 carbon atoms, furfuryl or a naphthyl radical, the two nitrogen atoms to which the radical A is bonded being separated from one another by at least two carbon atoms.
- the amine of the formula (I) enables a particularly low viscosity of the freshly mixed composition even at low quantities and thus particularly easy processing and application, especially on flat surfaces, and additionally particularly rapid curing in the cold, which is particularly important in cold ambient conditions enables quick access.
- a in formula (I) is preferably selected from the group consisting of 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,4-butylene, 1,3-butylene, 2-methyl-1, 2-propylene, 1,3-pentylene, 1,5-pentylene, 2,2-dimethyl-1,3-propylene, 1,6-hexylene, 2-methyl-1,5-pentylene, 1,7-heptylene, 1,8-octylene, 2,5-dimethyl-1,6-hexylene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 4(2)-methyl-1,3-cyclohexylene, 1 ,3-Cyclohexylene-bis(methylene) and 1,4-cyclohexylene-bis(methylene), in particular 1,2-ethylene, 1,2-propylene, 2-methyl-1,5-pentylene and 1,3-cyclohexylene bis(methylene).
- A represents 1,2-ethylene.
- Y in formula (I) is preferably selected from the group consisting of phenyl, 4-methylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 4-methoxyphenyl, 4-dimethylaminophenyl, furfuryl and 1-naphthyl.
- Y particularly preferably represents phenyl or furfuryl, in particular phenyl.
- A is 1,2-ethylene and Y is phenyl.
- the amine of formula (I) is therefore most preferably N-benzyl-1,2-ethanediamine.
- the amine hardener preferably contains at least one further amine with two primary amino groups, in particular selected from the group consisting of isophoronediamine, 1,3-bis(aminomethyl)benzene, 1,3-bis(aminomethyl) cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 2,2(4),4-trimethylhexamethylenediamine, bis(4-aminocyclohexyl)methane, 2(4)-methyl-1,3-diaminocyclohexane and 2 ,5(2,6)-Bis(aminomethy I) bi cy cl o[2.2.1 ]heptane.
- two primary amino groups in particular selected from the group consisting of isophoronediamine, 1,3-bis(aminomethyl)benzene, 1,3-bis(aminomethyl) cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 2,2(4),4-
- isophoronediamine 1,3-bis(aminomethyl)benzene and/or 1,3-bis(aminomethyl)cyclohexane are preferred.
- the amine hardener preferably contains so much amine of the formula (I) that 3 to 40%, particularly preferably 5 to 30%, in particular 6 to 20%, of all amine hydrogens in the epoxy resin composition come from the amine of the formula (I).
- the amine of the formula (I) is in particular a reaction product from the reductive alkylation of a superstoichiometric amount of the amine of the formula H2N-A-NH2 with the aldehyde of the formula Y-CHO and hydrogen, in particular after removal of the excess amine of the formula H2N-A- NH2.
- a reaction product can contain the corresponding dialkylated amine of the formula Y-CH2-NH-A-NH-CH2-Y, in particular in an amount of 10 to 30% by weight based on the total from amine of formula (I) and corresponding dialkylated amine.
- N-Benzyl-1,2-ethanediamine can therefore be used in particular as a mixture with a content of 10 to 30% by weight of N,N'-dibenzyl-1,2-ethanediamine based on the sum of N-benzyl-1,2- ethanediamine and N,N'-dibenzyl-1,2-ethanediamine can be used.
- the hardener component of the epoxy resin composition preferably further contains at least one tertiary amine of the formula where R represents one
- R is preferably methylene and n is 2 or in particular 3.
- Such a tertiary amine in the composition acts in particular as an accelerator during curing.
- the tertiary amine is selected from the group consisting of 2-(dimethylaminomethyl)phenol, 2,6-bis(dimethylaminomethyl)phenol, 2,4-bis-(dimethylaminomethyl)phenol, 2,4,6-tris(dimethylaminomethyl)phenol and 2,4,6-Tris(((3-(dimethylamino)propyl)amino)methyl)phenol, especially 2,4,6-Tris(((3-(dimethylamino)propyl)amino)methyl)phenol and 2,4,6-Tris(dimethylaminomethyl)phenol.
- the epoxy resin composition may additionally contain other components.
- the epoxy resin composition preferably further contains at least one diluent, which is present in particular only in a small amount.
- the epoxy resin composition preferably contains, based on the total epoxy resin composition, less than 20% by weight, in particular less than 15% by weight, preferably less than 10% by weight, of diluent with a boiling point at normal pressure of at least 180 ° C , in particular at least 200 °C.
- Suitable thinners are in particular 2-phenoxyethanol, 2-benzyloxyethanol,
- Benzyl alcohol ethylene glycol, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol diphenyl ether, diethylene glycol, Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, di-ethylene glycol mono-n-butyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol di-n-butylyl ether, propylene glycol butyl ether, propylene glycol phenyl ether, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol di-n-butyl ether, diphenylmethane , diisopropylnaphthalene, petroleum fractions such as Solvesso® -Types (from Exxon), alkylphenols such as tert.
- petroleum fractions such
- Preferred diluents are selected from the list consisting of benzyl alcohol, 2-phenoxyethanol, cardanol, styrenated phenol, diisopropylnaphthalene, isopropylbiphenylene and aromatic hydrocarbon resins containing phenol groups. Benzyl alcohol and/or diisopropylnaphthalene are particularly preferred.
- the epoxy resin composition may contain at least one further filler.
- Suitable further fillers are, in particular, inorganic fillers such as ground or precipitated calcium carbonate, which is optionally coated with fatty acid, in particular stearate, barite (barite), talc, quartz powder, quartz sand, silicon carbide, iron mica, dolomite, wollastonite, kaolin, mica (potassium aluminum -silicate), titanium dioxide, iron oxides, molecular sieve, aluminum oxide, aluminum hydroxide, magnesium hydroxide, silica, cement, gypsum or fly ash, as well as other fillers such as soot, graphite, metal powder such as aluminum, copper, iron, zinc, silver or steel, PVC Powder or hollow spheres.
- inorganic fillers such as ground or precipitated calcium carbonate, which is optionally coated with fatty acid, in particular stearate, barite (barite), talc, quartz powder, quartz sand, silicon carbide, iron mica
- Inorganic fillers are preferably selected from the list consisting of calcium carbonate, barite, quartz powder, quartz sand, titanium dioxide and iron oxides.
- the epoxy resin composition contains little or no inorganic fillers.
- the epoxy resin composition has the entire epoxy resin Composition has an inorganic filler content of less than 5% by weight, preferably less than 2% by weight, in particular less than 1% by weight.
- the content of petro-based binders and thinners is particularly low, making the composition particularly sustainable and in particular the CO2 footprint of the composition is significantly smaller than with conventional unfilled epoxy resin compositions.
- the epoxy resin composition contains further auxiliaries and additives, in particular the following:
- amines in particular monoamines such as benzylamine or furfurylamine, polyamidoamines, Mannich bases or aromatic polyamines such as in particular 4,4'-diaminodiphenylmethane, 2,4(6)-toluenediamine, or 3,5-diethyl-2,4(6 )-toluenediamine;
- accelerators in particular acids such as salicylic acid or p-toluenesulfonic acid, nitrates such as calcium nitrate, phenols, in particular bisphenols, phenol resins such as phenol-formaldehyde resins, also called novolaks, or phosphites such as di- or triphenyl phosphites;
- Polymers in particular polyamides, polysulfides, polyvinyl formal (PVF), polyvinyl butyral (PVB), polyurethanes (PUR), polymers with carboxyl groups, polyamides, butadiene-acrylonitrile copolymers, styrene-acrylonitrile copolymers, butadiene-styrene copolymers, homo- or Copolymers of unsaturated monomers, in particular from the group comprising ethylene, propylene, butylene, isobutylene, isoprene, vinyl acetate or alkyl (meth)acrylates, in particular chlorosulfonated polyethylenes or fluorine-containing polymers or sulfonamide-modified melamines;
- Fibers in particular glass fibers, carbon fibers, metal fibers, ceramic fibers or plastic fibers such as polyamide fibers or polyethylene fibers;
- Rheology modifiers especially thickeners or anti-settling agents
- Adhesion improvers especially organoalkoxysilanes
- - flame-retardant substances in particular the fillers already mentioned aluminum hydroxide or magnesium hydroxide, antimony trioxide, antimony pentoxide, boric acid (B(OH)s), zinc borate, zinc phosphate, melamine borate, melamine cyanurate, ammonium polyphosphate, melamine phosphate, melamine pyrophosphate, polybrominated diphenyl oxides or diphenyl ethers, phosphates such as in particular diphenyl cresyl phosphate, Resorcinol bis(diphenyl phosphate), resorcinol diphosphate oligomer, tetraphenyl resorcinol diphosphite, ethylenediamine diphosphate, bisphenol A bis(diphenyl phosphate), tris(chloroethyl) phosphate, tris(chloropropyl) phosphate,
- Additives such as, in particular, wetting agents, leveling agents, defoamers, deaerators, stabilizers against oxidation, heat, light or UV radiation or biocides.
- components of the epoxy resin composition can be contained in the resin and/or the hardener component.
- Components reactive with amine groups are preferably part of the resin component, substances reactive with epoxy groups are preferably part of the hardener component.
- the epoxy resin composition contains at least one surface-active additive selected from defoamers and deaerators, in particular in an amount based on the total epoxy resin composition of 0.01 to 1% by weight, preferably 0.02 to 0.5% by weight.
- a composition is particularly suitable as a floor coating and allows surface application in the liquid state to form a more attractive surface, in particular without defects caused by air bubbles such as craters or so-called pinholes.
- the epoxy resin composition preferably contains only a small content of solvents with a boiling point at normal pressure of less than 180 ° C, preferably less than 1% by weight, in particular less than 0.5% by weight, based on the entire epoxy resin composition. Such a largely solvent-free composition hardly causes any VOC emissions.
- the epoxy resin composition preferably contains less than 5% by weight of water.
- Such a non-water-based epoxy resin composition is particularly versatile and particularly water-resistant.
- the resin and hardener components are mixed together shortly before or during application.
- the mixing ratio is preferably chosen so that the ratio of the number of groups reactive towards epoxide groups, in particular amine hydrogens, to the number of epoxide groups is in the range from 0.5 to 1.5, in particular 0.7 to 1.2.
- the mixing ratio between the resin and hardener components is typically in the range of approximately 1:1 to 20:1.
- the components are mixed using a suitable process; it can be done continuously or batchwise.
- the mixing takes place in particular at ambient temperature, which is typically in the range from 5 to 45°C, preferably 10 to 35°C.
- Curing typically takes place at ambient temperature, in particular in the range from 5 to 45 ° C, preferably 10 to 35 ° C, and typically extends over a few hours to days.
- Another subject of the invention is a cured composition obtained from curing the epoxy resin composition after mixing the components.
- the epoxy resin composition is preferably applied to at least one substrate, with the following being particularly suitable:
- PCC polymer-modified cement mortar
- ECO epoxy resin-modified cement mortar
- Metals or alloys such as aluminum, iron, steel or non-ferrous metals, or surface-refined metals or alloys such as galvanized or chrome-plated metals;
- Plastics in particular hard or soft PVC, ABS, SAN, polycarbonate (PC), polyamide (PA), polyester, polystyrene, PMMA, epoxy resins, phenolic resins, PUR, POM, TPO, PE, PP, EPM or EPDM, whereby the plastics are optionally surface-treated using plasma, corona or flames;
- CFRP carbon fiber-reinforced plastics
- GFP glass fiber-reinforced plastics
- SMC sheet molding compounds
- Insulating foams in particular made of EPS, XPS, PUR, PIR, rock wool, glass wool or foamed glass (Foamglas);
- - coated substrates in particular painted tiles, painted concrete, powder-coated metals or alloys or painted sheets;
- the substrates can be pretreated before applying the epoxy resin composition.
- the epoxy resin composition described is preferably used as a covering, coating, leveling, sealing or adhesive primer, in particular as a component of a floor covering, in particular for offices, industrial halls, gymnasiums, cold rooms, balconies, terraces, parking decks or bridges.
- the epoxy resin composition is particularly used as a self-leveling or slightly thixotropic coating on a predominantly flat surface Applied to surfaces. It preferably has a liquid consistency with low viscosity and good flow properties. Preferably, 5 minutes after mixing the components, it has a viscosity at 20 ° C of 200 to 4,000 mPa s, particularly preferably 300 to 2,000 mPa s, in particular 400 to 1,000 mPa s, determined using plate Plate viscometer with plate diameter 50 mm, plate-to-plate distance 0.5 mm and shear rate 100 s' 1 .
- the epoxy resin composition has a viscosity at 12 ° C of less than 2,800 mPa s, preferably less than 2,400 mPa s, in particular less than 2,300 mPa s, 5 minutes after mixing the components , determined using a plate-plate viscometer with a plate diameter of 50 mm, a plate-plate distance of 0.5 mm and a shear rate of 100 s -1 , based on the entire epoxy resin composition, in particular less than 10% by weight of thinner with a boiling point at normal pressure of at least 180 ° C and in particular less than 5% by weight of reactive diluents containing epoxy groups.
- the epoxy resin composition preferably contains at least one amine of the formula (I) in the amine hardener, as described above.
- the mixed composition is preferably applied flatly as a thin film with a layer thickness of typically about 50 ⁇ m to about 5 mm, preferably 0.1 to 3 mm, onto a substrate, typically at ambient temperature, in particular in the range of about 5 to 45 ° C , preferably 10 to 35°C.
- the application is carried out in particular by pouring it onto the substrate to be coated and then spreading it evenly with, for example, a brush, a roller, a roller, a squeegee or a toothed trowel.
- the application can also be carried out as a spray application.
- the use of the epoxy resin composition results in an article comprising the cured composition.
- Another subject of the invention is a method for coating comprising the following steps a) mixing the components of the described epoxy resin composition, b) applying the mixed composition to at least one substrate, in particular a floor, in particular in a layer thickness in the range from 0.1 to 3 mm, c) allowing the applied coating to harden under ambient conditions, in particular at a temperature in the range of 5 to 45°C.
- step a) can be carried out continuously or batchwise. Mixing in batches in an open vessel using an agitator is preferred until a macroscopically homogeneous liquid is obtained.
- the application in step b) is preferably carried out by pouring onto the substrate and then evenly distributing, in particular using a brush, roller, roller, squeegee or toothed trowel. Care must be taken to ensure that the application takes place within the period of time within which the mixed composition has a viscosity suitable for the application, with a low viscosity making the application easier. This period of time suitable for processing is also referred to as "processing time”.
- substrates are particularly suitable as substrates, with the substrate preferably being in the form of a soil.
- Preferred substrates are concrete, mortar, cement screed, fiber cement, brick, brick, plaster, natural stone, asphalt, bitumen, PCC (polymer-modified cement mortar), ECO (epoxy resin-modified cement mortar), wood, wood materials bound with resins, resin-Texti I composite materials , plastics, fiber-reinforced plastics, painted tiles, painted concrete or coated floors of all kinds.
- Steps a), b) and c) are preferably all carried out at ambient temperatures, in particular at 5 to 45 ° C, particularly preferably at 5 to 30 ° C.
- the epoxy resin composition is, in particular, a component of a floor covering
- a sealing layer - one or more layers of a base layer, which is optionally sprinkled with quartz sand,
- the epoxy resin composition according to the invention can represent the adhesive primer and/or the leveling layer and/or the sealing layer and/or the base layer and/or the sealing of the floor covering. Further layers that do not correspond to the epoxy resin composition according to the invention can also be an epoxy resin composition, or another material, in particular a polyurethane or polyurea coating, or bitumen or asphalt.
- the epoxy resin composition according to the invention is used as a component of a soil protection system in which the epoxy resin composition according to the invention represents the base layer and/or the seal.
- the base layer is preferably sprinkled with quartz sand.
- Such a floor protection system is used in particular in industrial halls, warehouses, cold rooms or cellars, or on balconies, terraces, parking decks or bridges.
- the epoxy resin composition is used as a component of a soil protection system, in which the epoxy resin composition according to the invention represents a sealing layer which is covered with bitumen and then with asphalt.
- the sealing layer is preferably sprinkled with quartz sand.
- Such a soil protection system is used in particular on bridges.
- the epoxy resin composition according to the invention protects the underlying bridge structure from moisture penetration and thus from corrosion.
- a further subject of the invention is a soil protection system comprising i) at least one layer of the epoxy resin composition according to the invention in a layer thickness of 0.1 to 3 mm, ii) quartz sand which is scattered in and/or on, in particular on, the epoxy resin composition i). became, iii) optionally at least one further layer of the epoxy resin composition according to the invention, which is applied in particular in a layer thickness of 0.1 to 1 mm on the layer sprinkled with sand, iv) optionally at least one layer of bitumen, which is applied to the epoxy resin composition i) or iii ) is applied, and v) optionally at least one layer of asphalt which is applied to the bitumen layer.
- layer iii) is preferably present and forms the seal and thus the top layer or surface of the soil protection system.
- the soil protection system is preferably applied to a bridge and the epoxy resin composition according to the invention serves as a seal, which protects the underlying bridge structure from penetrating water and thus from corrosion.
- Layer iii) is preferably also present and layer iv) is thus applied to the epoxy resin composition iii).
- the floor protection system is particularly sustainable, easy to apply and enables technically high-quality and long-lasting protection with a visually appealing appearance.
- the content of petro-based binders and thinners and therefore the CO2 footprint is particularly low.
- a “standard climate” is a temperature of 23 ⁇ 1°C and a relative humidity of 50 ⁇ 5%.
- AHEW stands for amine hydrogen equivalent weight
- Epoxy liquid resin 1 bisphenol A diglycidyl ether, EEW approx. 187 g/eq (Araldit® GY-250, from Huntsman)
- Epoxy liquid resin 2 1:1 mixture of bisphenol A diglycidyl ether and bisphenol F diglycidyl ether, EEW approx. 177 g/eq (Epikote® Resin 05447, from Hexion)
- Olive pits ⁇ 100 pm Olive pits from the production of olive oil, dried, ground, particle size ⁇ 100 pm, lignin content > 20% by weight (from Micronizados Vegetales S.L)
- Pecan shells ⁇ 200 pm ground pecan shells, particle size ⁇ 200 pm, lignin content > 25 wt.% (from Composition Materials Co.)
- Walnut shells ⁇ 200 pm ground walnut shells, particle size ⁇ 200 pm, lignin content > 15 wt.% (from Composition Materials Co.)
- compositions Z-1 to Z-9 are Compositions Z-1 to Z-9:
- the resin component ingredients listed in Table 1 were mixed in the specified amounts (in parts by weight) with a dissolver and stored in a sealed container.
- the ingredients of the hardener component listed in Table 1 were mixed using a magnetic stirrer and stored in a sealed container.
- compositions designated "(Ref.)" are compositions not according to the invention and serve as a comparison.
- the ingredients of the resin component were mixed with a dissolver as described. 1 kg of the resin component mixed in this way was then stored in a sealed container on a shaking table at 45 ° C for 14 days. The sediment formed in the resin component was then stirred again using the dissolver. If the sediment could be evenly distributed again in the resin component after a short mixing time, the redispersibility was rated as "+", whereas if an even distribution could not be achieved after a short mixing time, the redispersibility was rated as "-”. The results can be seen in Table 1.
- the freshly mixed composition was applied to a concrete slab in an amount of 0.5 g/m 2 using a roller and stored in a standard climate for 7 days.
- compositions Z-1 and Z-6 to Z-8 according to the invention all had a viscosity in the range from 0.4 to 2 Pa s.
- compositions Z-10 to Z-15 The compositions were prepared according to the ingredients of the resin component and the hardener component given in Table 2 as described for composition Z-1.
- the dispersibility and redispersibility of the resin component were determined as described for Composition Z-1.
- the resin and hardener components were mixed in the weight ratio shown in Table 2 using a drill agitator.
- the mixed viscosity was measured 5 minutes after mixing the resin and hardener components at 12 ° C or at 20 ° C on a thermostatized plate-plate viscometer (plate diameter 50 mm, plate-plate distance 0.5 mm, shear rate 100 s-1) determined.
- the surface finish was tested as described for Composition Z-1.
- the Shore D hardness was determined according to DIN 53505 on two cylindrical test specimens (diameter 20 mm, thickness 5 mm), one stored at 8 ° C and one at 23 ° C and the hardness was measured after the specified time.
- compositions designated "(Ref.)" are compositions not according to the invention and serve as a comparison.
- a composition with a hardener containing N-benzyl-1,2-ethanediamine and a bio-based granulate according to the invention has a surprisingly low viscosity, especially at 12 ° C (Z-10 in comparison to Z-11 ), while with corresponding compositions with N-benzyl-1,2-ethanediamine in the hardener and quartz powder instead of the bio-based granules, this viscosity advantage does not exist (Z-12 (Ref.) compared to Z-13 (Ref.)).
Abstract
The present invention relates to epoxy resin compositions comprising a resin component containing at least one epoxy liquid resin, a hardener component containing at least one amine hardener, and at least one bio-based granular material with a particle size ≤ 200 µm and a lignin content of at least 10 wt.%, wherein the bio-based granular material is part of the resin and/or the hardener component and the content of bio-based granular material, in relation to the total epoxy resin composition, is 1 to 40 wt.%, preferably 2 to 30 wt.%, in particular 5 to 25 wt.%. The bio-based granular material can be well mixed into the resin and/or hardener component and well re-dispersed after storage. It enables visually high-value coatings with a defect-free and smooth surface.
Description
EPOXIDHARZ-ZUSAMMENSETZUNG MIT BIOBASIERTEM GRANULAT EPOXY RESIN COMPOSITION WITH BIO-BASED GRANULES
Technisches Gebiet Technical area
Die Erfindung betrifft das Gebiet der kalthärtenden Epoxidharz-Zusammensetzungen für Bodenbeschichtungen. The invention relates to the field of cold-curing epoxy resin compositions for floor coatings.
Stand der Technik State of the art
Bodenbeschichtungsprodukte auf Epoxidharz-Basis sind im Bauwesen weit verbreitet. Sie bestehen aus flüssigen Harz- und Härterkomponenten, welche vor der Applikation gemischt werden und dann bei Umgebungstemperaturen zur festen Beschichtung ausreagieren. Epoxy resin-based floor coating products are widely used in construction. They consist of liquid resin and hardener components, which are mixed before application and then react at ambient temperatures to form a solid coating.
Viele Bodenbeschichtungsprodukte enthalten anorganische Füllstoffe, abhängig von der gewünschten Anwendung und technischen Anforderung. Für gewisse Anwendungen sind jedoch Produkte gewünscht, welche weitgehend frei von anorganischen Füllstoffen sind. Alternativen zu klassischen Füllstoffen, welche den Anforderungen für Bodenbeschichtungsprodukten genügen, sind daher von grossem Interesse. Many floor coating products contain inorganic fillers, depending on the desired application and technical requirements. For certain applications, however, products are desired that are largely free of inorganic fillers. Alternatives to classic fillers that meet the requirements for floor coating products are therefore of great interest.
DE 10 2008 026 266 A1 beschreibt Formkörper zur Verwendung als Boden- oder Schallschutzelement, die durch Verkleben von vermahlenen Granulaten aus Olivenkernen mit reaktiven Klebstoffen auf Basis von Polyurethanen oder Epoxidharzen hergestellt werden. DE 10 2008 026 266 A1 describes moldings for use as a floor or soundproofing element, which are produced by bonding ground granules from olive pits with reactive adhesives based on polyurethanes or epoxy resins.
WO 2015/018466 beschreibt Klebstoffe für die Befestigungstechnik, welche sogenannt biogene Füllstoffe enthalten können. WO 2015/018466 describes adhesives for fastening technology, which can contain so-called biogenic fillers.
Alkylierte Amine wie N-Benzyl-1 ,2-ethandiamin sind bekannt als Härter für Epoxidharze, beispielsweise aus WO 2017/037069. Sie ermöglichen emissionsarme Epoxidharz-Beschichtungen mit schönen Oberflächen. Alkylated amines such as N-benzyl-1,2-ethanediamine are known as hardeners for epoxy resins, for example from WO 2017/037069. They enable low-emission epoxy resin coatings with beautiful surfaces.
Darstellung der Erfindung Presentation of the invention
Aufgabe der vorliegenden Erfindung ist es, eine für Bodenbeschichtungszwecke geeignete Epoxidharz-Zusammensetzung zur Verfügung zu stellen, welche Zusätze enthält, die sich gut einmischen und nach Lagerung gut redispergieren lassen, optisch hochwertige Beschichtungen mit fehlerfreier und glatter Oberfläche ermöglichen. Diese Aufgabe wird mit der Epoxidharz-Zusammensetzung wie in Anspruch 1 beschrieben gelöst. Das in der Zusammensetzung enthaltene biobasierte Granulat mit einem Ligningehalt von mindestens 10 Gew.-% neigt überraschend wenig zum
Absetzen und bleibt auch nach längerer Lagerung und Transport der Komponenten ausgezeichnet redispergierbar. Nach der Aushärtung zeigt die Zusammensetzung eine bemerkenswert glatte, optisch einwandfreie Oberfläche. Im Gegensatz dazu sind biobasierte Granulate ohne oder mit zu geringem Ligningehalt nach Lagerung nicht oder nur sehr schwer redispergierbar, was für ihre Anwendbarkeit nachteilig ist. Besonders überraschend ist, dass Zusammensetzungen, welche im Aminhärter mindestens ein Amin der Formel (I) enthalten, ein besonders gutes Fliessverhalten der vermischten Komponenten zeigen. Dabei ermöglicht das biobasierte Granulat in Kombination mit dem Amin der Formel (I) eine besonders niedrige Viskosität und zusätzlich eine besonders schnelle Aushärtung in der Kälte, wodurch entsprechende Beschichtungen auch bei kalten Umgebungsbedingungen besonders gut verarbeitbar und schnell begehbar sind. The object of the present invention is to provide an epoxy resin composition suitable for floor coating purposes, which contains additives that mix well and can be easily redispersed after storage, enabling optically high-quality coatings with a flawless and smooth surface. This task is achieved with the epoxy resin composition as described in claim 1. The bio-based granules contained in the composition with a lignin content of at least 10% by weight have a surprisingly low tendency to rot Settling and remains excellently redispersible even after prolonged storage and transport of the components. After curing, the composition exhibits a remarkably smooth, visually flawless surface. In contrast, bio-based granules with no or too low lignin content are difficult or impossible to redisperse after storage, which is disadvantageous for their applicability. It is particularly surprising that compositions which contain at least one amine of the formula (I) in the amine hardener show particularly good flow behavior of the mixed components. The bio-based granules in combination with the amine of formula (I) enable a particularly low viscosity and, in addition, particularly rapid curing in the cold, which means that corresponding coatings are particularly easy to process and can be walked on quickly even in cold ambient conditions.
Besonders interessant sind erfindungsgemässe Zusammensetzungen, welche weitgehend frei von anorganischen Füllstoffen sind, wobei das biobasierte Granulat als Teil des organischen Bindemittels betrachtet wird. Eine solche auch als „ungefüllt“ bezeichnete Zusammensetzung weist einen reduzierten Gehalt an petrobasierten Bindemitteln und Verdünnern auf und ist somit besonders nachhaltig. Particularly interesting are compositions according to the invention which are largely free of inorganic fillers, with the bio-based granules being considered as part of the organic binder. Such a composition, also known as “unfilled”, has a reduced content of petro-based binders and thinners and is therefore particularly sustainable.
Die Epoxidharz-Zusammensetzung ermöglicht besonders nachhaltige Bodenbeschichtungssysteme, die vor der Verwendung gut lagerfähig sind, einfach applizierbar sind und einen technisch hochwertigen und langlebigen Schutz bei optisch hochansprechender Erscheinung gewährleisten. The epoxy resin composition enables particularly sustainable floor coating systems that can be stored well before use, are easy to apply and ensure technically high-quality and long-lasting protection with a highly visually appealing appearance.
Weitere Aspekte der Erfindung sind Gegenstand weiterer unabhängiger Ansprüche. Besonders bevorzugte Ausführungsformen der Erfindung sind Gegenstand der abhängigen Ansprüche. Further aspects of the invention are the subject of further independent claims. Particularly preferred embodiments of the invention are the subject of the dependent claims.
Wege zur Ausführung der Erfindung Ways of carrying out the invention
Gegenstand der Erfindung ist eine Epoxidharz-Zusammensetzung umfassend The subject matter of the invention is an epoxy resin composition comprising
- eine Harz-Komponente enthaltend mindestens ein Epoxid-Flüssigharz, - a resin component containing at least one epoxy liquid resin,
- eine Härter-Komponente enthaltend mindestens einen Aminhärter, und - a hardener component containing at least one amine hardener, and
- mindestens ein biobasiertes Granulat mit einer Partikelgrösse < 200 pm und einem Ligningehalt von mindestens 10 Gew.-%, bevorzugt mindestens 15 Gew.-%, wobei das biobasierte Granulat Teil der Harz- und/oder der Härterkomponente ist und der Gehalt an biobasiertem Granulat bezogen auf die gesamte Epoxidharz- Zusammensetzung 1 bis 40 Gew.-%, bevorzugt 2 bis 30 Gew.-%, insbesondere 5 bis 25 Gew.-%, beträgt.
Als „Epoxid-Flüssigharz“ wird ein technisches Polyepoxid mit einer Glasübergangstemperatur unterhalb von 25°C bezeichnet. - at least one bio-based granulate with a particle size <200 pm and a lignin content of at least 10% by weight, preferably at least 15% by weight, the bio-based granulate being part of the resin and/or the hardener component and the content of bio-based granulate based on the entire epoxy resin composition is 1 to 40% by weight, preferably 2 to 30% by weight, in particular 5 to 25% by weight. “Epoxy liquid resin” is a technical polyepoxide with a glass transition temperature below 25°C.
Als „primäre Aminogruppe“ wird eine Aminogruppe bezeichnet, die an einen einzigen organischen Rest gebunden ist und zwei Wasserstoffatome trägt; als „sekundäre Aminogruppe“ wird eine Aminogruppe bezeichnet, die an zwei organische Reste, welche auch gemeinsam Teil eines Rings sein können, gebunden ist und ein Wasserstoffatom trägt; und als „tertiäre Aminogruppe“ wird eine Aminogruppe bezeichnet, die an drei organische Reste, welche auch zu zweit oder zu dritt Teil eines oder mehrerer Ringe sein können, gebunden ist und kein Wasserstoffatom trägt. A “primary amino group” is an amino group that is bonded to a single organic residue and carries two hydrogen atoms; A “secondary amino group” is an amino group that is bonded to two organic residues, which can also be part of a ring, and carries a hydrogen atom; and a “tertiary amino group” is an amino group that is bonded to three organic residues, two or three of which can be part of one or more rings, and does not contain a hydrogen atom.
Als „Aminwasserstoff“ werden die Wasserstoffatome von primären und sekudären Aminogruppen bezeichnet. The hydrogen atoms of primary and secondary amino groups are referred to as “amine hydrogen”.
Mit „Poly“ beginnende Substanznamen wie Polyamin, Polyol oder Polyepoxid bezeichnen Substanzen, die formal zwei oder mehr der in ihrem Namen vorkommenden funktionellen Gruppen pro Molekül enthalten. Substance names beginning with “Poly” such as polyamine, polyol or polyepoxide refer to substances that formally contain two or more of the functional groups appearing in their name per molecule.
Als „Olivenkern“ wird im vorliegenden Dokument insbesondere der Rückstand aus Olivenkernschalen nach dem Auspressen oder Extrahieren des Öls aus den Oliven bezeichnet. Ebenso werden als „Cashewnussschalen“ im vorliegenden Dokument insbesondere die übrigbleibenden Schalenbruchstücke der Cashewnüsse nach dem Auspressen oder Extrahieren des Cashewnussschalenöls aus den harten Schalen bezeichnet. In this document, “olive pit” refers in particular to the residue from olive pit shells after the oil has been pressed or extracted from the olives. Likewise, “cashew nut shells” in this document refer in particular to the remaining shell fragments of the cashew nuts after the cashew nut shell oil has been pressed or extracted from the hard shells.
Als „Verdünner“ wird eine in einem Epoxidharz lösliche und dessen Viskosität senkende Substanz bezeichnet, welche bei der Aushärtung chemisch nicht in das Epoxid-Polymer eingebunden wird. A “thinner” is a substance that is soluble in an epoxy resin and reduces its viscosity and is not chemically bound into the epoxy polymer during curing.
Als „Molekulargewicht“ wird die molare Masse (in Gramm pro Mol) eines Moleküls bezeichnet. Als „mittleres Molekulargewicht“ wird das Zahlenmittel Mn einer polydispersen Mischung von oligomeren oder polymeren Molekülen bezeichnet, welches üblicherweise mittels Gelpermeationschromatographie (GPC) gegen Polystyrol als Standard bestimmt wird. “Molecular weight” is the molar mass (in grams per mole) of a molecule. The “average molecular weight” is the number average M n of a polydisperse mixture of oligomeric or polymeric molecules, which is usually determined using gel permeation chromatography (GPC) against polystyrene as a standard.
Als „Raumtemperatur“ wird eine Temperatur von 23°C bezeichnet. A temperature of 23°C is referred to as “room temperature”.
Die Harz-Komponente und die Härter-Komponente der Epoxidharz-Zusammensetzung werden vor der Applikation der Zusammensetzung vorzugsweise getrennt voneinander gelagert. Die Harz-Komponente und die Härter-Komponente der Epoxidharz- Zusammensetzung liegen somit bevorzugt getrennt voneinander vor. Die separaten
Komponenten sind über einen Zeitraum von einigen Monaten bis zu einem Jahr oder länger lagerfähig, ohne dabei ihre Anwendbarkeit zu verlieren. The resin component and the hardener component of the epoxy resin composition are preferably stored separately from one another before application of the composition. The resin component and the hardener component of the epoxy resin composition are therefore preferably present separately from one another. The separate ones Components can be stored for a period of a few months to a year or longer without losing their usability.
Das biobasierte Granulat mit einem Ligningehalt von mindestens 10 Gew.-% hat eine Partikelgrösse von < 200 pm, vorzugsweise von < 100 pm. Die Partikelgrösse wird vorzugsweise mittels Siebanalyse wie in ASTM C136/C136M-2014 beschrieben bestimmt. Eine Partikelgrösse von mehr als 200 pm ist dahingehend von Nachteil, dass dadurch Beschichtungen erhalten werden, deren Oberflächenbeschaffenheit von Auge deutlich feststellbare Unebenheiten aufweist. Dies ist beispielsweise in Tabelle 1 im Vergleich der Zusammensetzung Z-1 mit Z-2 (Ref.) und Z-3 (Ref.) ersichtlich. The bio-based granules with a lignin content of at least 10% by weight have a particle size of <200 pm, preferably <100 pm. The particle size is preferably determined using sieve analysis as described in ASTM C136/C136M-2014. A particle size of more than 200 pm is disadvantageous in that it results in coatings whose surface properties have unevenness that can be clearly seen by the eye. This can be seen, for example, in Table 1 in the comparison of the composition Z-1 with Z-2 (Ref.) and Z-3 (Ref.).
Die Epoxidharz-Zusammensetzung enthält 1 bis 40 Gew.-%, bevorzugt 2 bis 30 Gew.- %, insbesondere 5 bis 25 Gew.-%, biobasiertes Granulat. The epoxy resin composition contains 1 to 40% by weight, preferably 2 to 30% by weight, in particular 5 to 25% by weight, of bio-based granules.
Ein Anteil an biobasiertem Granulat von mehr als 40 Gew.-% bezogen auf das Gesamtgewicht der Epoxidharz-Zusammensetzung ist dahingehend von Nachteil, dass dadurch eine ausreichende Dispergierbarkeit der Epoxidharz-Zusammensetzung nicht mehr gegeben ist. Dies ist beispielsweise in Tabelle 1 im Vergleich der Zusammensetzungen Z-1 und Z-6 bis Z-8 mit Z-9 (Ref.) ersichtlich. A proportion of bio-based granules of more than 40% by weight based on the total weight of the epoxy resin composition is disadvantageous in that this means that the epoxy resin composition is no longer sufficiently dispersible. This can be seen, for example, in Table 1 in the comparison of the compositions Z-1 and Z-6 to Z-8 with Z-9 (Ref.).
Erwähnte bevorzugte Bereiche sind dahingehend von Vorteil, dass dadurch eine gute Dispergierbarkeit der Epoxidharz-Zusammensetzung sowie ein hoher Anteil an biobasiertem Granulat erreicht werden kann. The preferred ranges mentioned are advantageous in that good dispersibility of the epoxy resin composition as well as a high proportion of bio-based granules can be achieved.
Bevorzugt weist das biobasierte Granulat einen Feuchtigkeitsgehalt von weniger als 15 Gew.-%, bevorzugt weniger als 12 Gew.-%, auf. Ein solches Granulat ist besonders gut in die jeweilige Komponente einmischbar und gewährleistet eine störungsfreie Aushärtung der Zusammensetzung The bio-based granules preferably have a moisture content of less than 15% by weight, preferably less than 12% by weight. Such granules can be mixed particularly well into the respective component and ensure trouble-free curing of the composition
Als biobasiertes Granulat geeignet sind zerkleinerte Hölzer aller Art mit einem Ligningehalt von mindestens 10 Gew.-%. All types of shredded wood with a lignin content of at least 10% by weight are suitable as bio-based granules.
Als biobasiertes Granulat bevorzugt sind Abfallprodukte von landwirtschaftlichen Erzeugnissen, insbesondere Nahrungsmitteln wie insbesondere Gelen, Nüssen oder Samen, wobei nicht essbare Anteile in Form von Schalen, Hülsen oder Kernen aus verholztem Material mit einem Ligningehalt von mindestens 10 Gew.-% anfallen. Diese
werden für die erfindungsgemässe Verwendung aufbereitet und auf die gewünschte Partikelgrösse bzw. Partikelverteilung gemahlen und gegebenenfalls weiter behandelt, insbesondere getrocknet oder gesiebt. Preferred bio-based granules are waste products from agricultural products, in particular foods such as gels, nuts or seeds, with inedible components in the form of shells, pods or cores made of woody material with a lignin content of at least 10% by weight. This are prepared for use according to the invention and ground to the desired particle size or particle distribution and, if necessary, further treated, in particular dried or sieved.
Besonders bevorzugt ist das biobasierte Granulat mit einem Ligningehalt von mindestens 10 Gew.-% ausgewählt aus der Gruppe bestehend aus gemahlenen Olivenkernen, Kokosnussschalen, Mandelschalen, Walnussschalen, Pecannussschalen, Paranussschalen, Haselnussschalen, Macadamianussschalen, Cashewnussschalen, Pistazienschalen, Kakaofruchtschalen, Aprikosenkernschalen, Pfirsichkernschalen und Zwetschgenkernschalen. Particularly preferred is the bio-based granulate with a lignin content of at least 10% by weight selected from the group consisting of ground olive kernels, coconut shells, almond shells, walnut shells, pecan shells, Brazil nut shells, hazelnut shells, macadamia nut shells, cashew nut shells, pistachio shells, cocoa fruit shells, apricot kernel shells, peach kernel shells and plum kernel shells .
Am meisten bevorzugt ist das biobasierte Granulat ein Granulat aus Olivenkernen. Dieses Granulat ist in hoher Menge und guter Qualität verfügbar und ermöglicht Epoxidharz-Zusammensetzungen mit besonders guter Redispergierbarkeit nach Lagerung der Komponenten und einer besonders guten Verarbeitbarkeit bei kalten Temperaturen wie insbesondere 12 °C. Most preferably, the bio-based granules are granules made from olive stones. This granulate is available in large quantities and of good quality and enables epoxy resin compositions with particularly good redispersibility after storage of the components and particularly good processability at cold temperatures, in particular 12 ° C.
Ein geeignetes Granulat aus Olivenkernen ist vorzugsweise erhältlich von Olivenkernschalenbruch aus der Gewinnung von Olivenöl, welcher getrocknet, gemahlen und gesiebt wird. Vorzugsweise weist das Granulat aus Olivenkernen einen Ligningehalt von mindestens 15 Gew.-% und einen Ölgehalt von weniger als 3 Gew.- %, vorzugsweise weniger als 1 Gew.-%, besonders bevorzugt von weniger als 0.5 Gew.-%, auf. Vorzugsweise weist das Granulat aus Olivenkernen eine Härte nach Mohs von 3 bis 4 auf. A suitable granulate of olive pits is preferably available from olive pit shell fragments from the production of olive oil, which are dried, ground and sieved. The olive kernel granules preferably have a lignin content of at least 15% by weight and an oil content of less than 3% by weight, preferably less than 1% by weight, particularly preferably less than 0.5% by weight. The olive stone granules preferably have a Mohs hardness of 3 to 4.
Überraschenderweise wurde gefunden, dass die Zugabe von vergleichbaren Mengen an biobasierten Granulaten mit geringem Ligningehalt oder ohne Lignin, wie beispielsweise Reishülsen mit einer Partikelgrösse von 1 bis 30 pm, zu einer fast doppelt so hohen Viskosität führen. Insbesondere liessen sich die damit hergestellten Harz-Komponenten nach Lagerung und Absetzen der Reishülsen nicht wieder redispergieren. Bei Verwendung der erfindungsgemässen Granulate mit einem Ligningehalt von mindestens 10 Gew.-%, bevorzugt mindestens 15 Gew.-%, war ein erneutes Dispergieren nach Lagerung und Absetzen des Granulats hingegen problemlos möglich. Dies ist beispielsweise in Tabelle 1 im Vergleich der Zusammensetzungen Z-1 und Z-6 bis Z-8 mit Z-4 (Ref.) und Z-5 (Ref.) ersichtlich.
Bevorzugt ist das biobasierte Granulat ein Bestandteil der Harz-Komponente. Bevorzugt weist die Harz-Komponente bezogen auf die gesamte Harz-Komponente einen Gehalt an biobasiertem Granulat von 2 bis 45 Gew.-%, besonders bevorzugt 4 bis 35 Gew.-%, insbesondere 6 bis 30 Gew.-%, auf. Surprisingly, it was found that the addition of comparable amounts of bio-based granules with low lignin content or without lignin, such as rice husks with a particle size of 1 to 30 pm, lead to a viscosity that is almost twice as high. In particular, the resin components produced with it could not be redispersed again after storage and settling of the rice husks. However, when using the granules according to the invention with a lignin content of at least 10% by weight, preferably at least 15% by weight, redispersion after storage and settling of the granules was possible without any problems. This can be seen, for example, in Table 1 in the comparison of the compositions Z-1 and Z-6 to Z-8 with Z-4 (Ref.) and Z-5 (Ref.). The bio-based granules are preferably part of the resin component. The resin component preferably has a content of bio-based granules of 2 to 45% by weight, particularly preferably 4 to 35% by weight, in particular 6 to 30% by weight, based on the total resin component.
Die Harz-Komponente der Epoxidharz-Zusammensetzung enthält mindestens ein Epoxid-Flüssigharz. The resin component of the epoxy resin composition contains at least one epoxy liquid resin.
Ein geeignetes Epoxid-Flüssigharz wird auf bekannte Art und Weise erhalten, insbesondere aus der Oxidation der entsprechenden Olefine oder aus der Reaktion von Epichlorhydrin mit den entsprechenden Polyolen, Polyphenolen oder Aminen. A suitable epoxy liquid resin is obtained in a known manner, in particular from the oxidation of the corresponding olefins or from the reaction of epichlorohydrin with the corresponding polyols, polyphenols or amines.
Geeignete Epoxid-Flüssigharze sind insbesondere aromatische Epoxidharze, insbesondere die Glycidylether von: Suitable epoxy liquid resins are in particular aromatic epoxy resins, in particular the glycidyl ethers of:
- Bisphenol A, Bisphenol F oder Bisphenol A/F, wobei A für Aceton und F für Formaldehyd steht, welche als Edukte zur Herstellung dieser Bisphenole dienten. Im Fall von Bisphenol F können auch Stellungsisomere vorhanden sein, insbesondere abgeleitet von 2,4'- oder 2,2'-Hydroxyphenylmethan; - Bisphenol A, bisphenol F or bisphenol A/F, where A stands for acetone and F for formaldehyde, which served as starting materials for the production of these bisphenols. In the case of bisphenol F, positional isomers may also be present, in particular derived from 2,4'- or 2,2'-hydroxyphenylmethane;
- Dihydroxybenzol-Derivaten wie Resorcin, Hydrochinon oder Brenzkatechin; - Dihydroxybenzene derivatives such as resorcinol, hydroquinone or catechol;
- weiteren Bisphenolen oder Polyphenolen wie Bis(4-hydroxy-3-methylphenyl)methan, 2,2-Bis(4-hydroxy-3-methylphenyl)propan (Bisphenol C), Bis(3,5-dimethyl-4- hydroxyphenyl)methan, 2,2-Bis(3,5-dimethyl-4-hydroxyphenyl)propan, 2,2-Bis(3,5- dibromo-4-hydroxyphenyl)propan, 2,2-Bis(4-hydroxy-3-tert.butylphenyl)propan, 2,2- Bis(4-hydroxyphenyl)butan (Bisphenol B), 3,3-Bis(4-hydroxyphenyl)pentan, 3,4- Bis(4-hydroxyphenyl)hexan, 4,4-Bis(4-hydroxyphenyl)heptan, 2,4-Bis(4- hydroxyphenyl)-2-methylbutan, 2,4-Bis(3,5-dimethyl-4-hydroxyphenyl)-2- methylbutan, 1 ,1-Bis(4-hydroxyphenyl)cyclohexan (Bisphenol Z), 1 ,1-Bis(4- hydroxyphenyl)-3,3,5-trimethylcyclohexan (Bisphenol TMC), 1 ,1-Bis(4- hydroxyphenyl)-1 -phenylethan, 1 ,4-Bis[2-(4-hydroxyphenyl)-2-propyl]benzol (Bisphenol-P), 1 ,3-Bis[2-(4-hydroxyphenyl)-2-propyl]benzol (Bisphenol M), 4,4'- Dihydroxydiphenyl (DOD), 4,4'-Dihydroxybenzophenon, Bis(2-hydroxynaphth-1- yl)methan, Bis(4-hydroxynaphth-1-yl)methan, 1 ,5-Dihydroxynaphthalin, Tris(4- hydroxyphenyl)methan, 1 ,1 ,2,2-Tetrakis(4-hydroxyphenyl)ethan, Bis(4- hydroxyphenyl)ether oder Bis(4-hydroxyphenyl)sulfon;
- Novolaken, welche insbesondere Kondensationsprodukte von Phenol oder Kresolen mit Formaldehyd bzw. Paraformaldehyd oder Acetaldehyd oder Crotonaldehyd oder Isobutyraldehyd oder 2-Ethylhexanal oder Benzaldehyd oder Furfural sind; - other bisphenols or polyphenols such as bis(4-hydroxy-3-methylphenyl)methane, 2,2-bis(4-hydroxy-3-methylphenyl)propane (bisphenol C), bis(3,5-dimethyl-4-hydroxyphenyl) methane, 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3- tert-butylphenyl)propane, 2,2-bis(4-hydroxyphenyl)butane (bisphenol B), 3,3-bis(4-hydroxyphenyl)pentane, 3,4-bis(4-hydroxyphenyl)hexane, 4,4- Bis(4-hydroxyphenyl)heptane, 2,4-bis(4-hydroxyphenyl)-2-methylbutane, 2,4-bis(3,5-dimethyl-4-hydroxyphenyl)-2-methylbutane, 1,1-bis( 4-hydroxyphenyl)cyclohexane (Bisphenol Z), 1,1-Bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (Bisphenol TMC), 1,1-Bis(4-hydroxyphenyl)-1-phenylethane, 1, 4-Bis[2-(4-hydroxyphenyl)-2-propyl]benzene (Bisphenol-P), 1,3-Bis[2-(4-hydroxyphenyl)-2-propyl]benzene (Bisphenol M), 4,4 '-Dihydroxydiphenyl (DOD), 4,4'-dihydroxybenzophenone, bis(2-hydroxynaphth-1-yl)methane, bis(4-hydroxynaphth-1-yl)methane, 1,5-dihydroxynaphthalene, tris(4-hydroxyphenyl) methane, 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)ether or bis(4-hydroxyphenyl)sulfone; - Novolaks, which are in particular condensation products of phenol or cresols with formaldehyde or paraformaldehyde or acetaldehyde or crotonaldehyde or isobutyraldehyde or 2-ethylhexanal or benzaldehyde or furfural;
- aromatischen Aminen, wie Anilin, Toluidin, 4-Aminophenol, 4,4'-Methylendiphe- nyldiamin, 4,4'-Methylendiphenyldi-(N-methyl)amin, 4,4'-[1 ,4-Phenylen-bis(1- methylethyliden)]bisanilin (Bisanilin-P) oder 4,4'-[1 ,3-Phenylen-bis(1- methylethyliden)]bisanilin (Bisanilin-M). - aromatic amines, such as aniline, toluidine, 4-aminophenol, 4,4'-methylenediphenyldiamine, 4,4'-methylenediphenyldi-(N-methyl)amine, 4,4'-[1,4-phenylene-bis( 1-methylethylidene)]bisaniline (bisaniline-P) or 4,4'-[1,3-phenylene-bis(1-methylethylidene)]bisaniline (bisaniline-M).
Weitere geeignete Epoxid-Flüssigharze sind aliphatische oder cycloaliphatische Polyepoxide, insbesondere Other suitable epoxy liquid resins are aliphatic or cycloaliphatic polyepoxides, in particular
- Glycidylether von gesättigten oder ungesättigten, verzweigten oder unverzweigten, zyklischen oder offenkettigen di-, tri- oder tetrafunktionellen C2- bis Cso-Alkoholen, insbesondere Ethylenglykol, Propylenglykol, Butylenglykol, Hexandiol, Octandiol, Polypropylenglykolen, Dimethylolcyclohexan, Neopentylglykol, Dibromoneopentylglykol, Rizinusöl, Trimethylolpropan, Trimethylolethan, Pentaerythrol, Sorbit oder Glycerin, oder alkoxyliertes Glycerin oder alkoxyliertes Trimethylolpropan; - glycidyl ethers of saturated or unsaturated, branched or unbranched, cyclic or open-chain di-, tri- or tetrafunctional C2 to Cso alcohols, in particular ethylene glycol, propylene glycol, butylene glycol, hexanediol, octanediol, polypropylene glycols, dimethylolcyclohexane, neopentyl glycol, dibromoneopentyl glycol, castor oil, Trimethylolpropane , trimethylolethane, pentaerythrol, sorbitol or glycerin, or alkoxylated glycerin or alkoxylated trimethylolpropane;
- hydrierte Bisphenol A-, F- oder A/F-Flüssigharze, beziehungsweise die Glycidylisierungsprodukte von hydriertem Bisphenol A, F oder A/F; - hydrogenated bisphenol A, F or A/F liquid resins, or the glycidylation products of hydrogenated bisphenol A, F or A/F;
- ein N-Glycidylderivat von Amiden oder heterocyclischen Stickstoffbasen, wie Triglycidylcyanurat oder Triglycidylisocyanurat, oder Umsetzungsprodukte von Epichlorhydrin mit Hydantoin; - an N-glycidyl derivative of amides or heterocyclic nitrogen bases, such as triglycidyl cyanurate or triglycidyl isocyanurate, or reaction products of epichlorohydrin with hydantoin;
- Epoxidharze aus der Oxidation von Olefinen, wie insbesondere Vinylcylohexen, Dicyclopentadien, Cyclohexadien, Cyclododecadien, Cyclododecatrien, Isopren, 1 ,5- Hexadien, Butadien, Polybutadien oder Divinylbenzol. - Epoxy resins from the oxidation of olefins, such as in particular vinylcylohexene, dicyclopentadiene, cyclohexadiene, cyclododecadiene, cyclododecatriene, isoprene, 1,5-hexadiene, butadiene, polybutadiene or divinylbenzene.
Weiterhin geeignet sind Epoxid-Flüssigharze, welche zumindest teilweise auf nachwachsenden Rohstoffen basieren, wie insbesondere Diglycidylether von Vanillinalkohol, Diglycidylether von Isosorbid oder Triglycidylether von Glycerin, sowie Bisphenol A-Diglycidylether von biobasiertem Epichlorhydrin. Also suitable are epoxy liquid resins which are at least partially based on renewable raw materials, such as in particular diglycidyl ether of vanillin alcohol, diglycidyl ether of isosorbide or triglycidyl ether of glycerol, as well as bisphenol A diglycidyl ether of bio-based epichlorohydrin.
Das Epoxidharz-Flüssigharz ist insbesondere ein aromatisches Flüssigharz auf der Basis eines Bisphenols oder Novolaks, insbesondere mit einem mittleren Epoxid- Equivalentgewicht im Bereich von 156 bis 210 g/eq.
Besonders geeignet ist ein Bisphenol A-Diglycidylether und/oder Bisphenol F- Diglycidylether, wie sie kommerziell beispielsweise als Araldite® GY 250, Araldite® PY 304, Araldite® GY 282 (von Huntsman) oder D.E.R.™ 331 oder D.E.R.™ 330 (von Dow) oder Epon™ Resin 828 (von Hexion) erhältlich sind. Solche Flüssigharze weisen eine für Epoxidharze niedrige Viskosität auf und ermöglichen eine schnelle Aushärtung und hohe Härten. The epoxy resin liquid resin is in particular an aromatic liquid resin based on a bisphenol or novolak, in particular with an average epoxy equivalent weight in the range from 156 to 210 g/eq. Particularly suitable is a bisphenol A diglycidyl ether and/or bisphenol F diglycidyl ether, such as those commercially available, for example, as Araldite® GY 250, Araldite® PY 304, Araldite® GY 282 (from Huntsman) or DER™ 331 or DER™ 330 (from Dow ) or Epon™ Resin 828 (from Hexion) are available. Such liquid resins have a low viscosity for epoxy resins and enable rapid curing and high hardness.
Besonders bevorzugt ist weiterhin ein Bisphenol A-Diglycidylether aus der Umsetzung von Bisphenol A mit biobasiertem Epichlorhydrin. Dies ermöglicht besonders nachhaltige Epoxidharz-Zusammensetzungen. A bisphenol A diglycidyl ether from the reaction of bisphenol A with bio-based epichlorohydrin is also particularly preferred. This enables particularly sustainable epoxy resin compositions.
Weiterhin besonders geeignet sind Phenol-Formaldehyd Novolak-Glycidylether, insbesondere mit einer mittleren Funktionalität im Bereich von 2.3 bis 4, bevorzugt 2.5 bis 3. Sie können Anteile von weiteren Epoxidharzen enthalten, insbesondere Bisphenol A-Diglycidylether oder Bisphenol F-Diglycidylether. Also particularly suitable are phenol-formaldehyde novolak glycidyl ethers, in particular with an average functionality in the range from 2.3 to 4, preferably 2.5 to 3. They can contain portions of other epoxy resins, in particular bisphenol A diglycidyl ether or bisphenol F diglycidyl ether.
Weiterhin besonders geeignet sind Diglycidylether von Vanillinalkohol oder Triglycidylether von Glycerol, insbesondere Diglycidylether von Vanillinalkohol. Dies ermöglicht besonders nachhaltige Epoxidharz-Zusammensetzungen. Diglycidyl ethers of vanillin alcohol or triglycidyl ethers of glycerol, in particular diglycidyl ethers of vanillin alcohol, are also particularly suitable. This enables particularly sustainable epoxy resin compositions.
Bevorzugt enthält die Harz-Komponente zusätzlich mindestens einen Epoxidgruppenhaltige Reaktivverdünner, insbesondere 1 bis 15 Gew.-%, bevorzugt 1.5 bis 10 Gew.- %, insbesondere 2 bis 8 Gew.-%, Epoxidgruppen-haltige Reaktivverdünner bezogen auf das Gesamtgewicht der Epoxidharz-Zusammensetzung. The resin component preferably additionally contains at least one reactive diluent containing epoxy groups, in particular 1 to 15% by weight, preferably 1.5 to 10% by weight, in particular 2 to 8% by weight, of reactive diluent containing epoxy groups, based on the total weight of the epoxy resin. Composition.
Bevorzugte Epoxidgruppen-haltige Reaktivverdünner sind Butandioldiglycidylether, Hexandioldiglycidylether, Trimethylolpropandi- oder -triglycidylether, Phenylglyci- dylether, Kresylglycidylether, Guaiacolglycidylether, 4-Methoxyphenylglycidylether, p-n- Butylphenylglycidylether, p-tert.Butylphenylglycidylether, 4-Nonylphenylglycidylether, 4- Dodecylphenylglycidylether, Vanillinglycidylether, Cardanolglycidylether, Benzylglycidylether, Allylglycidylether, Butylglycidylether, Hexylglycidylether, 2- Ethylhexylglycidylether oder Glycidylether von natürlichen Alkoholen wie insbesondere Cs- bis Cw- oder C12- bis C14- oder C13- bis Cis-Alkylglycidylether. Preferred reactive diluents containing epoxy groups are butanediol diglycidyl ether, hexanediol diglycidyl ether, trimethylolpropane di- or triglycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether, guaiacol glycidyl ether, 4-methoxyphenyl glycidyl ether, p-n-butylphenyl glycidyl ether, p-tert-butylphenyl glycidyl ether, 4-nonylphenyl glycidyl ether, 4- Dodecylphenyl glycidyl ether, vanilla glycidyl ether, cardanol glycidyl ether, Benzyl glycidyl ether, allyl glycidyl ether, butyl glycidyl ether, hexyl glycidyl ether, 2-ethylhexyl glycidyl ether or glycidyl ether of natural alcohols such as in particular Cs to Cw or C12 to C14 or C13 to cis alkyl glycidyl ethers.
Besonders bevorzugt sind Glycidylether von natürlichen Alkoholen, insbesondere C12- bis Ci4-Alkylglycidylether. Damit werden besonders gut verarbeitbare Epoxidharz- Zusammensetzungen erhalten. Glycidyl ethers of natural alcohols, in particular C12 to C14 alkyl glycidyl ethers, are particularly preferred. This results in particularly easy-to-process epoxy resin compositions.
Gegebenenfalls enthält die Harz-Komponente zusätzlich Anteile von Epoxid-Festharz.
Die Härter-Komponente der Epoxidharz-Zusammensetzung enthält mindestens einen Aminhärter. If necessary, the resin component additionally contains portions of solid epoxy resin. The hardener component of the epoxy resin composition contains at least one amine hardener.
Geeignete Aminhärter sind insbesondere aliphatische, cycloaliphatische oder arylaliphatische Di- oder Triamine mit mindestens 3 Aminwasserstoffen, wie insbesondere Suitable amine hardeners are in particular aliphatic, cycloaliphatic or arylaliphatic diamines or triamines with at least 3 amine hydrogens, such as in particular
- primäre Di- oder Triamine, insbesondere 2, 2-Dimethyl-1 ,3-propandiamin, 1 ,3- Pentandiamin (DAMP), 1 ,5-Pentandiamin, 1 ,5-Diamino-2-methylpentan (MPMD), 2- Butyl-2-ethyl-1 ,5-pentandiamin (C11-Neodiamin), 1 ,6-Hexandiamin, 2,5-Dimethyl- 1 ,6-hexandiamin, 2,2(4),4-Trimethylhexamethylendiamin (TMD), 1 ,7-Heptandiamin,- primary di- or triamines, in particular 2, 2-dimethyl-1,3-propanediamine, 1,3-pentanediamine (DAMP), 1,5-pentanediamine, 1,5-diamino-2-methylpentane (MPMD), 2- Butyl-2-ethyl-1,5-pentanediamine (C11-neodiamine), 1,6-hexanediamine, 2,5-dimethyl-1,6-hexanediamine, 2,2(4),4-trimethylhexamethylenediamine (TMD), 1 ,7-heptanediamine,
1.8-Octandiamin, 1 ,9-Nonandiamin, 1 ,10-Decandiamin, 1 ,11-Undecandiamin, 1 ,12- Dodecandiamin, 1 ,2-, 1 ,3- oder 1 ,4-Diaminocyclohexan, Bis(4-aminocyclohexyl)- methan, Bis(4-amino-3-methylcyclohexyl)methan, Bis(4-amino-3-ethylcyclo- hexyl)methan, Bis(4-amino-3,5-dimethylcyclohexyl)methan, Bis(4-amino-3-ethyl-5- methylcyclohexyl)methan, 1-Amino-3-aminomethyl-3,5,5-trimethylcyclohexan (Isophorondiamin oder lPDA), 1 ,3-Bis(aminomethyl)cyclohexan, 1 ,4- Bis(aminomethyl)cyclohexan, 2(4)-Methyl-1 ,3-diaminocyclohexan, 2, 5(2,6)- Bis(aminomethyl)bicyclo[2.2.1]heptan (NBDA), 3(4),8(9)-Bis(amino- methyl)tricyclo[5.2.1 .02’6]decan, 1 ,4-Diamino-2,2,6-trimethylcyclohexan (TMCDA),1,8-octanediamine, 1,9-nonanediamine, 1,10-decanediamine, 1,11-undecanediamine, 1,12-dodecanediamine, 1,2-, 1,3- or 1,4-diaminocyclohexane, bis(4-aminocyclohexyl) - methane, bis(4-amino-3-methylcyclohexyl)methane, bis(4-amino-3-ethylcyclohexyl)methane, bis(4-amino-3,5-dimethylcyclohexyl)methane, bis(4-amino-3 -ethyl-5-methylcyclohexyl)methane, 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (isophoronediamine or lPDA), 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 2(4)-Methyl-1,3-diaminocyclohexane, 2, 5(2,6)-bis(aminomethyl)bicyclo[2.2.1]heptane (NBDA), 3(4),8(9)-bis(amino - methyl)tricyclo[5.2.1 .0 2 ' 6 ]decane, 1,4-diamino-2,2,6-trimethylcyclohexane (TMCDA),
1 .8-Menthandiamin, 3,9-Bis(3-aminopropyl)-2,4,8, 10-tetraoxaspiro[5.5]undecan, 1 ,3- Bis(aminomethyl)benzol (MXDA) oder 1 ,4-Bis(aminomethyl)benzol, 1,8-menthanediamine, 3,9-bis(3-aminopropyl)-2,4,8, 10-tetraoxaspiro[5.5]undecane, 1,3-bis(aminomethyl)benzene (MXDA) or 1,4-bis( aminomethyl)benzene,
- Ethergruppen-haltige aliphatische primäre Di- oder Triamine, insbesondere Bis(2- aminoethyl)ether, 3,6-Dioxaoctan-1 ,8-diamin, 4,7-Dioxadecan-1 ,10-diamin, 4,7- Dioxadecan-2,9-diamin, 4,9-Dioxadodecan-1 , 12-diamin, 5,8-Dioxadodecan-3, 10- diamin, 4,7,10-T rioxatridecan-1 , 13-diamin oder höhere Oligomere dieser Diamine, Bis(3-aminopropyl)polytetrahydrofurane oder andere Polytetrahydrofurandiamine, oder Polyoxyalkylendi- oder -triamine, insbesondere die Jeffamine® D-230, D-400, D-2000, EDR-104, EDR-148, EDR-176, T-403, T-3000 oder Jeffamine® T-5000 (alle von Huntsman), oder entsprechende Amine von BASF oder Nitroil; - Aliphatic primary di- or triamines containing ether groups, in particular bis(2-aminoethyl) ether, 3,6-dioxaoctane-1,8-diamine, 4,7-dioxadecane-1,10-diamine, 4,7-dioxadecane 2,9-diamine, 4,9-dioxadodecane-1, 12-diamine, 5,8-dioxadodecane-3, 10-diamine, 4,7,10-trioxatridecan-1, 13-diamine or higher oligomers of these diamines, Bis(3-aminopropyl)polytetrahydrofurans or other polytetrahydrofurandiamines, or polyoxyalkylenedi- or triamines, in particular the Jeffamine® D-230, D-400, D-2000, EDR-104, EDR-148, EDR-176, T-403, T-3000 or Jeffamine® T-5000 (all from Huntsman), or corresponding amines from BASF or Nitroil;
- sekundäre Aminogruppen aufweisende Polyamine, wie insbesondere 2-Ami- noethylpiperazin, 3-Dimethylaminopropylamin (DMAPA), 3-(3-(Dimethylami- no)propylamino)propylamin (DMAPAPA), Bis(hexamethylen)triamin (BHMT), Diethylentriamin (DETA), Triethylentetramin (TETA), Tetraethylenpentamin (TEPA), Pentaethylenhexamin (PEHA) oder höhere Homologe linearer Polyethylenamine, Dipropylentriamin (DPTA), N-(2-Aminoethyl)-1 ,3-propandiamin (N3-Amin), N,N'-
Bis(3-aminopropyl)ethylendiamin (N4-Amin), N,N'-Bis(3-aminopropyl)-1 ,4- diaminobutan, N5-(3-Aminopropyl)-2-methyl-1 ,5-pentandiamin, N3-(3-Aminopentyl)- 1 ,3-pentandiamin, N5-(3-Amino-1-ethylpropyl)-2-methyl-1 ,5-pentandiamin, N,N'- Bis(3-amino-1-ethylpropyl)-2-methyl-1 ,5-pentandiamin, Produkte aus der reduktiven Alkylierung von primären Polyaminen mit Aldehyden oder Ketonen, insbesondere N- Benzyl-1 ,2-ethandiamin, N-Furfuryl-1 ,2-ethandiamin, N-Tetrahydrofurfuryl-1 ,2- ethandiamin, N-Benzyl-1 ,2-propandiamin, N-Benzyl-1 ,3-bis(aminomethyl)benzol, N- 2-Ethylhexyl-1 ,3-bis(aminomethyl)benzol, N-Benzyldiethylentriamin, N,N'- Dibenzyldiethylentriamin, N-Benzyltriethylentetramin, N,N'- Dibenzyltriethylentetramin, N"-Benzyl-N,N'-bis(3-aminopropyl)ethylendiamin, N",N"'- Dibenzyl-N,N'-bis(3-aminopropyl)ethylendiamin, oder partiell styrolisierte Polyamine wie zum Beispiel styrolisiertes MXDA enthaltend N-Phenylethyl-1 ,3- bis(aminomethyl)benzol (erhältlich als Gaskamine® 240 von Mitsubishi Gas Chemical); sowie - Polyamines containing secondary amino groups, such as in particular 2-aminoethylpiperazine, 3-dimethylaminopropylamine (DMAPA), 3-(3-(dimethylamino)propylamino)propylamine (DMAPAPA), bis(hexamethylene)triamine (BHMT), diethylenetriamine (DETA ), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA) or higher homologues of linear polyethyleneamines, dipropylenetriamine (DPTA), N-(2-aminoethyl)-1,3-propanediamine (N3-amine), N,N' - Bis(3-aminopropyl)ethylenediamine (N4-amine), N,N'-bis(3-aminopropyl)-1,4-diaminobutane, N5-(3-aminopropyl)-2-methyl-1,5-pentanediamine, N3 -(3-Aminopentyl)- 1,3-pentanediamine, N5-(3-amino-1-ethylpropyl)-2-methyl-1,5-pentanediamine, N,N'-Bis(3-amino-1-ethylpropyl) -2-methyl-1,5-pentanediamine, products from the reductive alkylation of primary polyamines with aldehydes or ketones, in particular N-benzyl-1,2-ethanediamine, N-furfuryl-1,2-ethanediamine, N-tetrahydrofurfuryl-1 ,2-ethanediamine, N-benzyl-1,2-propanediamine, N-benzyl-1,3-bis(aminomethyl)benzene, N-2-ethylhexyl-1,3-bis(aminomethyl)benzene, N-benzyldiethylenetriamine, N "N'-dibenzyldiethylenetriamine, N-benzyltriethylenetetramine, N,N'-dibenzyltriethylenetetramine, N"-benzyl-N,N'-bis(3-aminopropyl)ethylenediamine, N",N"'-dibenzyl-N,N'-bis (3-aminopropyl)ethylenediamine, or partially styrenized polyamines such as styrenized MXDA containing N-phenylethyl-1,3-bis(aminomethyl)benzene (available as Gaskamine® 240 from Mitsubishi Gas Chemical); as well as
- aminfunktionelle Addukte der obengenannten oder weiterer Polyamine mit Epoxiden oder Epoxidharzen, insbesondere aminfunktionelle Addukte mit aromatischen Diepoxiden. - Amine-functional adducts of the above-mentioned or other polyamines with epoxides or epoxy resins, in particular amine-functional adducts with aromatic diepoxides.
Bevorzugt enthält der Aminhärter mindestens ein aliphatisches, cycloaliphatisches oder arylaliphatisches Di- oder Triamin mit mindestens 3 Aminwasserstoffen, insbesondere ausgewählt aus der Gruppe bestehend aus 2-Butyl-2-ethyl-1 ,5-pentandiamin (C11 - Neodiamin), 2,2(4),4-Trimethylhexamethylendiamin (TMD), 1 ,2-Diaminocyclohexan, Bis(4-aminocyclohexyl)methan, Isophorondiamin (IPDA), 1 ,3- Bis(aminomethyl)cyclohexan, 1 ,4-Bis(aminomethyl)cyclohexan, 2(4)-Methyl-1 ,3- diaminocyclohexan, 2,5(2,6)-Bis(aminomethyl)bicyclo[2.2.1]heptan (NBDA), 1 ,3- Bis(aminomethyl)benzol (MXDA), Polyoxypropylendiaminen mit mittlerem Molekulargewicht Mn von 200 bis 500 g/mol, Polyoxypropylentriaminen mit mittlerem Molekulargewicht Mn von 300 bis 500 g/mol, 3-(3- (Dimethylamino)propylamino)propylamin (DMAPAPA), Bis(hexamethylen)triamin (BHMT), Triethylentetramin (TETA), Tetraethylenpentamin (TEPA), Pentaethylenhexamin (PEHA) N,N'-Bis(3-aminopropyl)ethylendiamin (N4-Amin), N- Benzyl-1 ,2-ethandiamin, N-Furfuryl-1 ,2-ethandiamin, N-Tetrahydrofurfuryl-1 ,2- ethandiamin, N-Benzyl-1 ,3-bis(aminomethyl)benzol und aminfunktionellen Addukten dieser Amine mit aromatischen Diepoxiden.
Bevorzugt enthält der Aminhärter Isophorondiamin (IPDA). Dieses Amin ermöglicht eine hohe Glasumwandlungstemperatur und wenig Neigung zum Vergilben. The amine hardener preferably contains at least one aliphatic, cycloaliphatic or arylaliphatic diamine or triamine with at least 3 amine hydrogens, in particular selected from the group consisting of 2-butyl-2-ethyl-1,5-pentanediamine (C11 - neodiamine), 2,2( 4),4-trimethylhexamethylenediamine (TMD), 1,2-diaminocyclohexane, bis(4-aminocyclohexyl)methane, isophoronediamine (IPDA), 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 2 (4)-Methyl-1,3-diaminocyclohexane, 2,5(2,6)-bis(aminomethyl)bicyclo[2.2.1]heptane (NBDA), 1,3-bis(aminomethyl)benzene (MXDA), polyoxypropylenediamines with an average molecular weight M n of 200 to 500 g/mol, polyoxypropylenetriamines with an average molecular weight M n of 300 to 500 g/mol, 3-(3-(dimethylamino)propylamino)propylamine (DMAPAPA), bis(hexamethylene)triamine (BHMT) , triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA) N,N'-bis(3-aminopropyl)ethylenediamine (N4-amine), N-benzyl-1,2-ethanediamine, N-furfuryl-1,2 -ethanediamine, N-tetrahydrofurfuryl-1,2-ethanediamine, N-benzyl-1,3-bis(aminomethyl)benzene and amine-functional adducts of these amines with aromatic diepoxides. The amine hardener preferably contains isophoronediamine (IPDA). This amine enables a high glass transition temperature and little tendency to yellowing.
Weiterhin bevorzugt enthält der Aminhärter 1 ,3-Bis(aminomethyl)benzol (MXDA). Dieses Amin ermöglicht eine besonders schnelle Aushärtung. The amine hardener also preferably contains 1,3-bis(aminomethyl)benzene (MXDA). This amine enables particularly rapid curing.
Weiterhin bevorzugt enthält der Aminhärter 1 ,3-Bis(aminomethyl)cyclohexan. Dieses Amin ermöglicht eine schnelle Aushärtung und besonders wenig Neigung zum Vergilben. The amine hardener also preferably contains 1,3-bis(aminomethyl)cyclohexane. This amine enables rapid curing and a particularly low tendency to yellowing.
In einer besonders bevorzugten Ausführungsform der Erfindung enthält der Aminhärter mindestens ein Amin der Formel (I), In a particularly preferred embodiment of the invention, the amine hardener contains at least one amine of the formula (I),
NH2-A— NH— CH2-Y (I) wobei NH 2 -A— NH— CH 2 -Y (I) where
A für einen zweiwertigen Alkylen- oder Cycloalkylen-Rest mit 2 bis 8 C-Atomen steht, und A represents a divalent alkylene or cycloalkylene radical with 2 to 8 carbon atoms, and
Y für einen gegebenenfalls substituierten Phenyl-Rest mit 6 bis 12 C-Atomen, Furfuryl oder einen Naphthyl-Rest steht, wobei die beiden Stickstoffatome, an welche der Rest A gebunden ist, durch mindestens zwei C-Atome voneinander getrennt sind. Y represents an optionally substituted phenyl radical with 6 to 12 carbon atoms, furfuryl or a naphthyl radical, the two nitrogen atoms to which the radical A is bonded being separated from one another by at least two carbon atoms.
Das Amin der Formel (I) ermöglicht bereits bei niedriger Einsatzmenge eine besonders niedrige Viskosität der frisch vermischten Zusammensetzung und somit eine besonders einfache Verarbeitbarkeit und Applizierbarkeit, insbesondere auf ebenen Flächen, und zusätzlich eine besonders schnelle Aushärtung in der Kälte, was bei kalten Umgebungsbedingungen eine besonders schnelle Begehbarkeit ermöglicht. The amine of the formula (I) enables a particularly low viscosity of the freshly mixed composition even at low quantities and thus particularly easy processing and application, especially on flat surfaces, and additionally particularly rapid curing in the cold, which is particularly important in cold ambient conditions enables quick access.
Bevorzugt ist A in Formel (I) ausgewählt aus der Gruppe bestehend aus 1 ,2-Ethylen, 1 ,2-Propylen, 1 ,3-Propylen, 1 ,4-Butylen, 1 ,3-Butylen, 2-Methyl-1 ,2-propylen, 1 ,3- Pentylen, 1 ,5-Pentylen, 2,2-Dimethyl-1 ,3-propylen, 1 ,6-Hexylen, 2-Methyl-1 ,5-pentylen, 1 ,7-Heptylen, 1 ,8-Octylen, 2,5-Dimethyl-1 ,6-hexylen, 1 ,2-Cyclohexylen, 1 ,3- Cyclohexylen, 1 ,4-Cyclohexylen, 4(2)-Methyl-1 ,3-cyclohexylen, 1 ,3-Cyclohexylen- bis(methylen) und 1 ,4-Cyclohexylen-bis(methylen), insbesondere 1 ,2-Ethylen, 1 ,2- Propylen, 2-Methyl-1 ,5-pentylen und 1 ,3-Cyclohexylen-bis(methylen). A in formula (I) is preferably selected from the group consisting of 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,4-butylene, 1,3-butylene, 2-methyl-1, 2-propylene, 1,3-pentylene, 1,5-pentylene, 2,2-dimethyl-1,3-propylene, 1,6-hexylene, 2-methyl-1,5-pentylene, 1,7-heptylene, 1,8-octylene, 2,5-dimethyl-1,6-hexylene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 4(2)-methyl-1,3-cyclohexylene, 1 ,3-Cyclohexylene-bis(methylene) and 1,4-cyclohexylene-bis(methylene), in particular 1,2-ethylene, 1,2-propylene, 2-methyl-1,5-pentylene and 1,3-cyclohexylene bis(methylene).
Am meisten bevorzugt steht A für 1 ,2-Ethylen.
Bevorzugt ist Y in Formel (I) ausgewählt aus der Gruppe bestehend aus Phenyl, 4- Methylphenyl, 4-lsopropylphenyl, 4-tert.Butylphenyl, 4-Methoxyphenyl, 4- Dimethylaminophenyl, Furfuryl und 1-Naphthyl. Most preferably, A represents 1,2-ethylene. Y in formula (I) is preferably selected from the group consisting of phenyl, 4-methylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 4-methoxyphenyl, 4-dimethylaminophenyl, furfuryl and 1-naphthyl.
Besonders bevorzugt steht Y für Phenyl oder Furfuryl, insbesondere für Phenyl. Y particularly preferably represents phenyl or furfuryl, in particular phenyl.
Am meisten bevorzugt stehen in Formel (I) A für 1 ,2-Ethylen und Y für Phenyl. Das Amin der Formel (I) ist somit am meisten bevorzugt N-Benzyl-1 ,2-ethandiamin. Most preferably in formula (I) A is 1,2-ethylene and Y is phenyl. The amine of formula (I) is therefore most preferably N-benzyl-1,2-ethanediamine.
Bevorzugt enthält der Aminhärter zusätzlich zu mindestens einem Amin der Formel (I) mindestens ein weiteres Amin mit zwei primären Aminogruppen, insbesondere ausgewählt aus der Gruppe bestehend aus Isophorondiamin, 1 ,3- Bis(aminomethyl)benzol, 1 ,3-Bis(aminomethyl)cyclohexan, 1 ,4-Bis(aminome- thyl)cyclohexan, 2,2(4),4-T rimethylhexamethylendiamin, Bis(4-aminocyclo- hexyl)methan, 2(4)-Methyl-1 ,3-diaminocyclohexan und 2,5(2,6)-Bis(aminome- thy I) bi cy cl o[2.2.1 ]heptan. In addition to at least one amine of the formula (I), the amine hardener preferably contains at least one further amine with two primary amino groups, in particular selected from the group consisting of isophoronediamine, 1,3-bis(aminomethyl)benzene, 1,3-bis(aminomethyl) cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 2,2(4),4-trimethylhexamethylenediamine, bis(4-aminocyclohexyl)methane, 2(4)-methyl-1,3-diaminocyclohexane and 2 ,5(2,6)-Bis(aminomethy I) bi cy cl o[2.2.1 ]heptane.
Davon bevorzugt sind Isophorondiamin, 1 ,3-Bis(aminomethyl)benzol und/oder 1 ,3-Bis- (aminomethyl)cyclohexan. Of these, isophoronediamine, 1,3-bis(aminomethyl)benzene and/or 1,3-bis(aminomethyl)cyclohexane are preferred.
Bevorzugt enthält der Aminhärter so viel Amin der Formel (I), dass 3 bis 40 %, besonders bevorzugt 5 bis 30 %, insbesondere 6 bis 20 %, aller Aminwasserstoffe der Epoxidharz-Zusammensetzung vom Amin der Formel (I) stammen. The amine hardener preferably contains so much amine of the formula (I) that 3 to 40%, particularly preferably 5 to 30%, in particular 6 to 20%, of all amine hydrogens in the epoxy resin composition come from the amine of the formula (I).
Das Amin der Formel (I) ist insbesondere ein Reaktionsprodukt aus der reduktiven Alkylierung einer überstöchiometrischen Menge des Amins der Formel H2N-A-NH2 mit dem Aldehyd der Formel Y-CHO und Wasserstoff, insbesondere nach Entfernung des überschüssigen Amins der Formel H2N-A-NH2. Zusätzlich zum Amin der Formel (I) kann ein solches Reaktionsprodukt das entsprechende dialky lierte Amin der Formel Y- CH2-NH-A-NH-CH2-Y enthalten, insbesondere in einer Menge von 10 bis 30 Gew.-% bezogen auf die Summe aus Amin der Formel (I) und entsprechendem dialkyliertem Amin. The amine of the formula (I) is in particular a reaction product from the reductive alkylation of a superstoichiometric amount of the amine of the formula H2N-A-NH2 with the aldehyde of the formula Y-CHO and hydrogen, in particular after removal of the excess amine of the formula H2N-A- NH2. In addition to the amine of the formula (I), such a reaction product can contain the corresponding dialkylated amine of the formula Y-CH2-NH-A-NH-CH2-Y, in particular in an amount of 10 to 30% by weight based on the total from amine of formula (I) and corresponding dialkylated amine.
N-Benzyl-1 ,2-ethandiamin kann somit insbesondere als Gemisch mit einem Gehalt von 10 bis 30 Gew.-% N,N’-Dibenzyl-1 ,2-ethandiamin bezogen auf die Summe aus N- Benzyl-1 ,2-ethandiamin und N,N’-Dibenzyl-1 ,2-ethandiamin eingesetzt werden.
Die Härter-Komponente der Epoxidharz-Zusammensetzung enthält bevorzugt weiterhin mindestens ein tertiäres Amin der Formel
wobei R für eineN-Benzyl-1,2-ethanediamine can therefore be used in particular as a mixture with a content of 10 to 30% by weight of N,N'-dibenzyl-1,2-ethanediamine based on the sum of N-benzyl-1,2- ethanediamine and N,N'-dibenzyl-1,2-ethanediamine can be used. The hardener component of the epoxy resin composition preferably further contains at least one tertiary amine of the formula where R represents one
Alkylengruppe mit 1 bis 20 C-Atomen, welche gegebenenfalls substituiert ist und gegebenenfalls Hetereoatome aufweist, steht, und n für einen Wert von 1 bis 3 steht, bevorzugt in einer Menge von 0.25 bis 5 Gew.-%, insbesondere 0.5 bis 3 Gew.-%, bezogen auf das Gesamtgewicht der Epoxidharz-Zusammensetzung. Alkylene group with 1 to 20 carbon atoms, which is optionally substituted and optionally has heteroatoms, and n represents a value of 1 to 3, preferably in an amount of 0.25 to 5% by weight, in particular 0.5 to 3% by weight. -%, based on the total weight of the epoxy resin composition.
Bevorzugt steht R für Methylen und n für 2 oder insbesondere 3. R is preferably methylene and n is 2 or in particular 3.
Ein solches tertiäres Amin wirkt in der Zusammensetzung insbesondere als Beschleuniger bei der Aushärtung. Such a tertiary amine in the composition acts in particular as an accelerator during curing.
Vorzugsweise ist das tertiäre Amin ausgewählt aus der Gruppe bestehend aus 2- (Dimethylaminomethyl)phenol, 2,6-Bis(dimethylaminomethyl)phenol, 2,4-Bis- (dimethylaminomethyl)phenol, 2,4,6-Tris(dimethylaminomethyl)phenol und 2,4,6- T ris(((3-(dimethylamino)propyl)amino)methyl)phenol, insbesondere 2,4,6-T ris(((3- (dimethylamino)propyl)amino)methyl)phenol und 2,4,6-Tris(dimethyl- aminomethyl)phenol. Preferably, the tertiary amine is selected from the group consisting of 2-(dimethylaminomethyl)phenol, 2,6-bis(dimethylaminomethyl)phenol, 2,4-bis-(dimethylaminomethyl)phenol, 2,4,6-tris(dimethylaminomethyl)phenol and 2,4,6-Tris(((3-(dimethylamino)propyl)amino)methyl)phenol, especially 2,4,6-Tris(((3-(dimethylamino)propyl)amino)methyl)phenol and 2,4,6-Tris(dimethylaminomethyl)phenol.
Am meisten bevorzugt ist 2,4,6-Tris(dimethylaminomethyl)phenol. Dieses tertiäre Amin ist kommerziell beispielsweise als Ancamine® K54 von Evonik erhältlich. Most preferred is 2,4,6-tris(dimethylaminomethyl)phenol. This tertiary amine is commercially available, for example, as Ancamine® K54 from Evonik.
Die Epoxidharz-Zusammensetzung kann zusätzlich weitere Bestandteile enthalten. The epoxy resin composition may additionally contain other components.
Bevorzugt enthält die Epoxidharz-Zusammensetzung weiterhin mindestens einen Verdünner, welcher insbesondere nur in einer geringen Menge vorhanden ist. The epoxy resin composition preferably further contains at least one diluent, which is present in particular only in a small amount.
Vorzugsweise enthält die Epoxidharz-Zusammensetzung bezogen auf die gesamte Epoxidharz-Zusammensetzung weniger als 20 Gew.-%, insbesondere weniger als 15 Gew.-%, bevorzugt weniger als 10 Gew.-%, Verdünner mit einem Siedepunkt bei Normaldruck von mindestens 180 °C, insbesondere mindestens 200 °C. The epoxy resin composition preferably contains, based on the total epoxy resin composition, less than 20% by weight, in particular less than 15% by weight, preferably less than 10% by weight, of diluent with a boiling point at normal pressure of at least 180 ° C , in particular at least 200 °C.
Geeignete Verdünner sind insbesondere 2-Phenoxyethanol, 2-Benzyloxyethanol,Suitable thinners are in particular 2-phenoxyethanol, 2-benzyloxyethanol,
Benzylalkohol, Ethylenglykol, Ethylenglykoldimethylether, Ethylenglykoldiethylether, Ethylenglykoldibutylether, Ethylenglykoldiphenylether, Diethylenglykol,
Diethylenglykolmonomethylether, Diethylenglykolmonoethylether, Di- ethylenglykolmono-n-butylether, Diethylenglykoldimethylether, Diethylenglykol- diethylether, Diethylenglykoldi-n-butylylether, Propylenglykolbutylether, Propylenglykolphenylether, Dipropylenglykol, Dipropylenglykolmonomethylether, Dipropylenglykoldimethylether, Dipropylenglykoldi-n-butylether, Diphenylmethan, Diisopropylnaphthalin, Erdölfraktionen wie zum Beispiel Solvesso®-Typen (von Exxon), Alkylphenole wie tert. Butylphenol, Nonylphenol, Dodecylphenol, Cardanol (aus Cashewschalen-Öl, enthaltend als Hauptbestandteil 3-(8,11 ,14- Pentadecatrienyl)phenol), styrolisiertes Phenol, Biphenole, aromatische Kohlenwasserstoffharze, insbesondere Phenolgruppen-haltige Typen, alkoxyliertes Phenol, insbesondere ethoxyliertes oder propoxyliertes Phenol, insbesondere 2- Phenoxyethanol, Isopropylbiphenyle, Adipate, Sebacate, Phthalate, Benzoate, organische Phosphor- oder Sulfonsäureester oder Sulfonamide. Benzyl alcohol, ethylene glycol, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol diphenyl ether, diethylene glycol, Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, di-ethylene glycol mono-n-butyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol di-n-butylyl ether, propylene glycol butyl ether, propylene glycol phenyl ether, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol di-n-butyl ether, diphenylmethane , diisopropylnaphthalene, petroleum fractions such as Solvesso® -Types (from Exxon), alkylphenols such as tert. Butylphenol, nonylphenol, dodecylphenol, cardanol (from cashew shell oil, containing 3-(8,11,14-pentadecatrienyl)phenol as the main component), styrenized phenol, biphenols, aromatic hydrocarbon resins, in particular types containing phenol groups, alkoxylated phenol, in particular ethoxylated or propoxylated phenol, in particular 2-phenoxyethanol, isopropylbiphenyls, adipates, sebacates, phthalates, benzoates, organic phosphorus or sulfonic acid esters or sulfonamides.
Bevorzugte Verdünner sind ausgewählt aus der Liste bestehend aus Benzylalkohol, 2- Phenoxyethanol, Cardanol, styrolisiertem Phenol, Diisopropylnaphthalin, Isopropylbiphenylen und phenolgruppenhaltigen aromatischen Kohlenwasserstoffharzen. Besonders bevorzugt sind Benzylalkohol und/oder Diisopropylnaphthalin. Preferred diluents are selected from the list consisting of benzyl alcohol, 2-phenoxyethanol, cardanol, styrenated phenol, diisopropylnaphthalene, isopropylbiphenylene and aromatic hydrocarbon resins containing phenol groups. Benzyl alcohol and/or diisopropylnaphthalene are particularly preferred.
Die Epoxidharz-Zusammensetzung kann mindestens einen weiteren Füllstoff enthalten. Geeignete weitere Füllstoffe sind insbesondere anorganische Füllstoffe wie gemahlenes oder gefälltes Calciumcarbonat, welches gegebenenfalls mit Fettsäure, insbesondere Stearaten, beschichtet ist, Baryt (Schwerspat), Talk, Quarzmehl, Quarzsand, Siliciumcarbid, Eisenglimmer, Dolomit, Wollastonit, Kaolin, Mica (Kalium- Aluminium-Silikat), Titandioxid, Eisenoxide, Molekularsieb, Aluminiumoxid, Aluminiumhydroxid, Magnesiumhydroxid, Kieselsäure, Zement, Gips oder Flugasche, sowie weitere Füllstoffe wie Russ, Graphit, Metall-Pulver wie Aluminium, Kupfer, Eisen, Zink, Silber oder Stahl, PVC-Pulver oder Hohlkugeln. The epoxy resin composition may contain at least one further filler. Suitable further fillers are, in particular, inorganic fillers such as ground or precipitated calcium carbonate, which is optionally coated with fatty acid, in particular stearate, barite (barite), talc, quartz powder, quartz sand, silicon carbide, iron mica, dolomite, wollastonite, kaolin, mica (potassium aluminum -silicate), titanium dioxide, iron oxides, molecular sieve, aluminum oxide, aluminum hydroxide, magnesium hydroxide, silica, cement, gypsum or fly ash, as well as other fillers such as soot, graphite, metal powder such as aluminum, copper, iron, zinc, silver or steel, PVC Powder or hollow spheres.
Bevorzugt sind anorganische Füllstoffe ausgewählt aus der Liste bestehend aus Calciumcarbonat, Baryt, Quarzmehl, Quarzsand, Titandioxid und Eisenoxiden. Inorganic fillers are preferably selected from the list consisting of calcium carbonate, barite, quartz powder, quartz sand, titanium dioxide and iron oxides.
In einer bevorzugten Ausführungsform der Erfindung enthält die Epoxidharz- Zusammensetzung nur wenig oder keine anorganischen Füllstoffe. Insbesondere weist die Epoxidharz-Zusammensetzung bezogen die gesamte Epoxidharz-
Zusammensetzung einen Gehalt an anorganischen Füllstoffen von weniger als 5 Gew.- %, bevorzugt weniger als 2 Gew.-%, insbesondere weniger als 1 Gew.-%, auf. In einer solchen auch als "ungefüllt" bezeichneten Epoxidharz-Zusammensetzung ist der Gehalt an petrobasierten Bindemitteln und Verdünnern besonders gering, wodurch die Zusammensetzung besonders nachhaltig ist und insbesondere der CO2-Fussabdruck der Zusammensetzung deutlich kleiner ist als bei herkömmlichen ungefüllten Epoxidharz-Zusammensetzungen. In a preferred embodiment of the invention, the epoxy resin composition contains little or no inorganic fillers. In particular, the epoxy resin composition has the entire epoxy resin Composition has an inorganic filler content of less than 5% by weight, preferably less than 2% by weight, in particular less than 1% by weight. In such an epoxy resin composition, also known as "unfilled", the content of petro-based binders and thinners is particularly low, making the composition particularly sustainable and in particular the CO2 footprint of the composition is significantly smaller than with conventional unfilled epoxy resin compositions.
Gegebenenfalls enthält die Epoxidharz-Zusammensetzung weitere Hilfs- und Zusatzstoffe, insbesondere die Folgenden: If necessary, the epoxy resin composition contains further auxiliaries and additives, in particular the following:
- weitere Amine, insbesondere Monoamine wie insbesondere Benzylamin oder Furfurylamin, Polyamidoamine, Mannich-Basen oder aromatische Polyamine wie insbesondere 4,4'-Diaminodiphenylmethan, 2,4(6)-Toluylendiamin, oder 3,5-Diethyl- 2,4(6)-toluylendiamin; - other amines, in particular monoamines such as benzylamine or furfurylamine, polyamidoamines, Mannich bases or aromatic polyamines such as in particular 4,4'-diaminodiphenylmethane, 2,4(6)-toluenediamine, or 3,5-diethyl-2,4(6 )-toluenediamine;
- Mercaptogruppen aufweisende Verbindungen, insbesondere flüssige Mercaptan- terminierte Polysulfidpolymere, Mercaptan-terminierte Polyoxyalkylenether, Mer- captan-terminierte Polyoxyalkylen-Derivate, Polyester von Thiocarbonsäuren, 2,4,6- Trimercapto-1 ,3,5-triazin, Triethylenglykoldimercaptan oder Ethandithiol; - Compounds containing mercapto groups, in particular liquid mercaptan-terminated polysulfide polymers, mercaptan-terminated polyoxyalkylene ethers, mercaptan-terminated polyoxyalkylene derivatives, polyesters of thiocarboxylic acids, 2,4,6-trimercapto-1,3,5-triazine, triethylene glycol dimercaptan or ethanedithiol;
- weitere Beschleuniger, insbesondere Säuren wie insbesondere Salicylsäure oder p- Toluolsulfansäure, Nitrate wie insbesondere Calciumnitrat, Phenole, insbesondere Bisphenole, Phenol-Harze wie insbesondere Phenol-Formaldehyd-Harze, auch Novolake genannt, oder Phosphite wie insbesondere Di- oder Triphenylphosphite;- other accelerators, in particular acids such as salicylic acid or p-toluenesulfonic acid, nitrates such as calcium nitrate, phenols, in particular bisphenols, phenol resins such as phenol-formaldehyde resins, also called novolaks, or phosphites such as di- or triphenyl phosphites;
- Polymere, insbesondere Polyamide, Polysulfide, Polyvinylformal (PVF), Polyvinylbutyral (PVB), Polyurethane (PUR), Polymere mit Carboxylgruppen, Polyamide, Butadien-Acrylnitril-Copolymere, Styrol-Acrylnitril-Copolymere, Butadien- Styrol-Copolymere, Homo- oder Copolymere von ungesättigten Monomeren, insbesondere aus der Gruppe umfassend Ethylen, Propylen, Butylen, Isobutylen, Isopren, Vinylacetat oder Alkyl(meth)acrylate, insbesondere chlorsulfonierte Polyethylene oder Fluor-haltige Polymere oder Sulfonamid-modifizierte Melamine;- Polymers, in particular polyamides, polysulfides, polyvinyl formal (PVF), polyvinyl butyral (PVB), polyurethanes (PUR), polymers with carboxyl groups, polyamides, butadiene-acrylonitrile copolymers, styrene-acrylonitrile copolymers, butadiene-styrene copolymers, homo- or Copolymers of unsaturated monomers, in particular from the group comprising ethylene, propylene, butylene, isobutylene, isoprene, vinyl acetate or alkyl (meth)acrylates, in particular chlorosulfonated polyethylenes or fluorine-containing polymers or sulfonamide-modified melamines;
- Fasern, insbesondere Glasfasern, Kohlefasern, Metallfasern, Keramikfasern oder Kunststofffasern wie Polyamidfasern oder Polyethylenfasern; - Fibers, in particular glass fibers, carbon fibers, metal fibers, ceramic fibers or plastic fibers such as polyamide fibers or polyethylene fibers;
- Nanofüllstoffe, insbesondere Carbon Nanotubes; - Nanofillers, especially carbon nanotubes;
- Farbstoffe oder Pigmente; - dyes or pigments;
- Lösemittel; - solvents;
- Rheologie-Modifizierer, insbesondere Verdicker oder Antiabsetzmittel;
- Haftverbesserer, insbesondere Organoalkoxysilane; - Rheology modifiers, especially thickeners or anti-settling agents; - Adhesion improvers, especially organoalkoxysilanes;
- flammhemmende Substanzen, insbesondere die bereits genannten Füllstoffe Aluminiumhydroxid oder Magnesiumhydroxid, Antimontrioxid, Antimonpentoxid, Borsäure (B(OH)s), Zinkborat, Zinkphosphat, Melaminborat, Melamincyanurat, Ammoniumpolyphosphat, Melaminphosphat, Melaminpyrophosphat, polybromierte Diphenyloxide oder Diphenylether, Phosphate wie insbesondere Diphenylkresylphosphat, Resorcinol-bis(diphenylphosphat), Resorcinoldiphosphat- Oligomer, Tetraphenylresorcinoldiphosphit, Ethylendiamindiphosphat, Bisphenol A- bis(diphenylphosphat), T ris(chloroethyl)phosphat, T ris(chloropropyl)phosphat,- flame-retardant substances, in particular the fillers already mentioned aluminum hydroxide or magnesium hydroxide, antimony trioxide, antimony pentoxide, boric acid (B(OH)s), zinc borate, zinc phosphate, melamine borate, melamine cyanurate, ammonium polyphosphate, melamine phosphate, melamine pyrophosphate, polybrominated diphenyl oxides or diphenyl ethers, phosphates such as in particular diphenyl cresyl phosphate, Resorcinol bis(diphenyl phosphate), resorcinol diphosphate oligomer, tetraphenyl resorcinol diphosphite, ethylenediamine diphosphate, bisphenol A bis(diphenyl phosphate), tris(chloroethyl) phosphate, tris(chloropropyl) phosphate,
T ris(dichloroisopropyl)phosphat, T ris[3-bromo-2,2-bis(bromomethyl)propyl]phosphat, Tetrabromo-Bisphenol-A, Bis(2,3-dibromopropylether) von Bisphenol A, bromierte Epoxidharze, Ethylen-bis(tetrabromophthalimid), Ethylen- bis(dibromonorbornandicarboximid), 1 ,2-Bis(tribromophenoxy)ethan, Tris(2,3- dibromopropyl)isocyanurat, T ribromophenol, Hexabromocyclododecan, Bis(hexachlorocyclopentadieno)cyclooctan oder Chlorparaffine; oder T ris(dichloroisopropyl) phosphate, T ris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate, tetrabromo-bisphenol-A, bis(2,3-dibromopropyl ether) of bisphenol A, brominated epoxy resins, ethylene-bis (tetrabromophthalimide), ethylene-bis(dibromonorbornanedicarboximide), 1,2-bis(tribromophenoxy)ethane, tris(2,3-dibromopropyl)isocyanurate, tribromophenol, hexabromocyclododecane, bis(hexachlorocyclopentadieno)cyclooctane or chlorinated paraffins; or
- Additive wie insbesondere Netzmittel, Verlaufmittel, Entschäumer, Entlüfter, Stabilisatoren gegen Oxidation, Wärme, Licht oder UV-Strahlung oder Biozide. - Additives such as, in particular, wetting agents, leveling agents, defoamers, deaerators, stabilizers against oxidation, heat, light or UV radiation or biocides.
Weitere Bestandteile der Epoxidharz-Zusammensetzung können in der Harz- und/oder der Härter-Komponente enthalten sein. Mit Amingruppen reaktive Bestandteile sind bevorzugt Bestandteil der Harz-Komponente, mit Epoxidgruppen reaktive Substanzen sind bevorzugt Bestandteil der Härter-Komponente. Other components of the epoxy resin composition can be contained in the resin and/or the hardener component. Components reactive with amine groups are preferably part of the resin component, substances reactive with epoxy groups are preferably part of the hardener component.
In einer bevorzugten Ausführungsform der Erfindung enthält die Epoxidharz- Zusammensetzung mindestens ein oberflächenaktives Additiv ausgewählt aus Entschäumern und Entlüftern, insbesondere in einer Menge bezogen auf die gesamte Epoxidharz-Zusammensetzung von 0.01 bis 1 Gew.-%, bevorzugt 0.02 bis 0.5 Gew.-%. Eine solche Zusammensetzung ist besonders geeignet als Bodenbeschichtung und erlaubt eine flächige Apüplikation im flüssigen Zustand unter Ausbildung einer schöneren Oberfläche, insbesondere ohne durch Luftblasen verursachte Fehler wie Krater oder sogenannte Pinholes. In a preferred embodiment of the invention, the epoxy resin composition contains at least one surface-active additive selected from defoamers and deaerators, in particular in an amount based on the total epoxy resin composition of 0.01 to 1% by weight, preferably 0.02 to 0.5% by weight. Such a composition is particularly suitable as a floor coating and allows surface application in the liquid state to form a more attractive surface, in particular without defects caused by air bubbles such as craters or so-called pinholes.
Bevorzugt enthält die Epoxidharz-Zusammensetzung nur einen geringen Gehalt an Lösemitteln mit einem Siedepunkt bei Normaldruck von weniger als 180 °C, bevorzugt weniger als 1 Gew.-%, insbesondere weniger als 0.5 Gew.-%, bezogen auf die
gesamte Epoxidharz-Zusammensetzung. Eine solche weitgehend lösemittelfreie Zusammensetzung verursacht kaum VOC Emissionen. The epoxy resin composition preferably contains only a small content of solvents with a boiling point at normal pressure of less than 180 ° C, preferably less than 1% by weight, in particular less than 0.5% by weight, based on the entire epoxy resin composition. Such a largely solvent-free composition hardly causes any VOC emissions.
Bevorzugt enthält die Epoxidharz-Zusammensetzung weniger als 5 Gew.-% Wasser. Eine solche, nicht-wasserbasierte Epoxidharz-Zusammensetzung ist besonders vielseitig verwendbar und besonders wasserbeständig. The epoxy resin composition preferably contains less than 5% by weight of water. Such a non-water-based epoxy resin composition is particularly versatile and particularly water-resistant.
Zur Anwendung der Epoxidharz-Zusammensetzung werden die Harz- und die Härter- Komponente kurz vor oder während der Applikation miteinander vermischt. To use the epoxy resin composition, the resin and hardener components are mixed together shortly before or during application.
Das Mischungsverhältnis wird bevorzugt so gewählt, dass das Verhältnis der Anzahl gegenüber Epoxidgruppen reaktiven Gruppen, insbesondere Aminwasserstoffen, zur Anzahl Epoxidgruppen im Bereich von 0.5 bis 1.5, insbesondere 0.7 bis 1.2, liegt. In Gewichtsteilen liegt das Mischungsverhältnis zwischen der Harz- und der Härter- Komponente typischerweise im Bereich von etwa 1 :1 bis 20:1. The mixing ratio is preferably chosen so that the ratio of the number of groups reactive towards epoxide groups, in particular amine hydrogens, to the number of epoxide groups is in the range from 0.5 to 1.5, in particular 0.7 to 1.2. In parts by weight, the mixing ratio between the resin and hardener components is typically in the range of approximately 1:1 to 20:1.
Die Vermischung der Komponenten erfolgt mittels eines geeigneten Verfahrens; sie kann kontinuierlich oder batchweise erfolgen. Die Vermischung erfolgt insbesondere bei Umgebungstemperatur, welche typischerweise im Bereich von 5 bis 45°C, bevorzugt 10 bis 35°C, liegt. The components are mixed using a suitable process; it can be done continuously or batchwise. The mixing takes place in particular at ambient temperature, which is typically in the range from 5 to 45°C, preferably 10 to 35°C.
Mit der Vermischung der Komponenten beginnt die Aushärtung durch chemische Reaktion. Dabei reagieren die in der Epoxidharz-Zusammensetzung vorhandenen Aminwasserstoffe und gegebenenfalls vorhandene weitere gegenüber Epoxidgruppen reaktive Gruppen mit den Epoxidgruppen unter deren Ringöffnung (Additionsreaktion). Als Ergebnis hauptsächlich dieser Reaktion polymerisiert die Zusammensetzung und härtet dadurch aus. When the components are mixed, hardening begins through a chemical reaction. The amine hydrogens present in the epoxy resin composition and any other groups that are reactive towards epoxy groups react with the epoxy groups, causing their ring to open (addition reaction). As a result primarily of this reaction, the composition polymerizes and thereby hardens.
Die Aushärtung erfolgt typischerweise bei Umgebungstemperatur, insbesondere im Bereich von 5 bis 45°C, bevorzugt 10 bis 35°C, und erstreckt sich typischerweise über einige Stunden bis Tage. Curing typically takes place at ambient temperature, in particular in the range from 5 to 45 ° C, preferably 10 to 35 ° C, and typically extends over a few hours to days.
Ein weiterer Gegenstand der Erfindung ist eine ausgehärtete Zusammensetzung erhalten aus der Aushärtung der Epoxidharz-Zusammensetzung nach dem Vermischen der Komponenten.
Die Applikation der Epoxidharz-Zusammensetzung erfolgt bevorzugt auf mindestens ein Substrat, wobei die Folgenden besonders geeignet sind: Another subject of the invention is a cured composition obtained from curing the epoxy resin composition after mixing the components. The epoxy resin composition is preferably applied to at least one substrate, with the following being particularly suitable:
- Glas, Glaskeramik, Beton, Mörtel, Zementestrich, Faserzement, Backstein, Ziegel, Gips oder Natursteine wie Granit oder Marmor; - Glass, glass ceramic, concrete, mortar, cement screed, fiber cement, brick, tile, plaster or natural stone such as granite or marble;
- Asphalt oder Bitumen; - asphalt or bitumen;
- Reparatur- oder Nivelliermassen auf Basis PCC (Polymer-modifizierter Zementmörtel) oder ECO (Epoxidharz-modifizierter Zementmörtel); - Repair or leveling compounds based on PCC (polymer-modified cement mortar) or ECO (epoxy resin-modified cement mortar);
- Metalle oder Legierungen wie Aluminium, Eisen, Stahl oder Buntmetalle, oder oberflächenveredelte Metalle oder Legierungen wie verzinkte oder verchromte Metalle; - Metals or alloys such as aluminum, iron, steel or non-ferrous metals, or surface-refined metals or alloys such as galvanized or chrome-plated metals;
- Leder, Textilien, Papier, Holz, mit Harzen, beispielsweise Phenol-, Melamin- oder Epoxidharzen, gebundene Holzwerkstoffe, Harz-Textil-Verbundwerkstoffe oder weitere sogenannte Polymer-Composites; - Leather, textiles, paper, wood, with resins, for example phenolic, melamine or epoxy resins, bonded wood materials, resin-textile composites or other so-called polymer composites;
- Kunststoffe, insbesondere Hart- oder Weich-PVC, ABS, SAN, Polycarbonat (PC), Polyamid (PA), Polyester, Polystyrol, PMMA, Epoxidharze, Phenolharze, PUR, POM, TPO, PE, PP, EPM oder EPDM, wobei die Kunststoffe gegebenenfalls mittels Plasma, Corona oder Flammen oberflächenbehandelt sind; - Plastics, in particular hard or soft PVC, ABS, SAN, polycarbonate (PC), polyamide (PA), polyester, polystyrene, PMMA, epoxy resins, phenolic resins, PUR, POM, TPO, PE, PP, EPM or EPDM, whereby the plastics are optionally surface-treated using plasma, corona or flames;
- Faserverstärkte Kunststoffe, wie Kohlefaser- verstärkte Kunststoffe (CFK), Glasfaserverstärkte Kunststoffe (GFK) oder Sheet Moulding Compounds (SMC); - Fiber-reinforced plastics, such as carbon fiber-reinforced plastics (CFRP), glass fiber-reinforced plastics (GRP) or sheet molding compounds (SMC);
- Isolierschäume, insbesondere aus EPS, XPS, PUR, PIR, Steinwolle, Glaswolle oder geschäumtem Glas (Foamglas); - Insulating foams, in particular made of EPS, XPS, PUR, PIR, rock wool, glass wool or foamed glass (Foamglas);
- beschichtete Substrate, insbesondere lackierte Fliesen, gestrichener Beton, pulverbeschichtete Metalle oder Legierungen oder lackierte Bleche; - coated substrates, in particular painted tiles, painted concrete, powder-coated metals or alloys or painted sheets;
- Beschichtungen, Farben oder Lacke, insbesondere beschichtete Böden, welche mit einer weiteren Bodenbelagsschicht überschichtet werden. - Coatings, paints or varnishes, especially coated floors, which are covered with another layer of floor covering.
Die Substrate können bei Bedarf vor dem Applizieren der Epoxidharz- Zusammensetzung vorbehandelt werden. If necessary, the substrates can be pretreated before applying the epoxy resin composition.
Bevorzugt wird die beschriebene Epoxidharz-Zusammensetzung verwendet als Belag, Beschichtung, Egalisierung, Abdichtung oder Haftgrundierung, insbesondere als Bestandteil eines Bodenbelags, insbesondere für Büros, Industriehallen, Turnhallen, Kühlräume, Balkone, Terrassen, Parkdecks oder Brücken. The epoxy resin composition described is preferably used as a covering, coating, leveling, sealing or adhesive primer, in particular as a component of a floor covering, in particular for offices, industrial halls, gymnasiums, cold rooms, balconies, terraces, parking decks or bridges.
Für eine solche Verwendung wird die Epoxidharz-Zusammensetzung insbesondere als selbstverlaufende oder leicht thixotropierte Beschichtung auf überwiegend ebene
Flächen appliziert. Sie weist dabei bevorzugt eine flüssige Konsistenz mit niedriger Viskosität und guten Verlaufseigenschaften auf. Bevorzugt weist sie 5 min nach dem Vermischen der Komponenten eine Viskosität bei 20 °C von 200 bis 4’000 mPa s, besonders bevorzugt 300 bis 2’000 mPa s, insbesondere 400 bis 1’000 mPa s, auf, bestimmt mittels Platte-Platte Viskosimeter mit Plattendurchmesser 50 mm, Platte- Platte-Abstand 0.5 mm und Scherrate 100 s'1. For such use, the epoxy resin composition is particularly used as a self-leveling or slightly thixotropic coating on a predominantly flat surface Applied to surfaces. It preferably has a liquid consistency with low viscosity and good flow properties. Preferably, 5 minutes after mixing the components, it has a viscosity at 20 ° C of 200 to 4,000 mPa s, particularly preferably 300 to 2,000 mPa s, in particular 400 to 1,000 mPa s, determined using plate Plate viscometer with plate diameter 50 mm, plate-to-plate distance 0.5 mm and shear rate 100 s' 1 .
In einer bevorzugten Ausführungsform der Erfindung weist die Epoxidharz- Zusammensetzung 5 min nach dem Vermischen der Komponenten eine Viskosität bei 12 °C von weniger als 2'800 mPa s, bevorzugt weniger als 2'400 mPa s, insbesondere weniger als 2'300 mPa s, auf, bestimmt mittels Platte-Platte Viskosimeter mit Plattendurchmesser 50 mm, Platte-Platte-Abstand 0.5 mm und Scherrate 100 s-1, wobei bezogen auf die gesamte Epoxidharz-Zusammensetzung insbesondere weniger als 10 Gew.% Verdünner mit einem Siedepunkt bei Normaldruck von mindestens 180 °C und insbesondere weniger als 5 Gew.-% Epoxidgruppen-haltige Reaktivverdünner enthalten sind. Eine solche Zusammensetzung ist besonders emissionsarm und auch bei kühlen Umgebungsbedingungen hervorragend applizierbar, insbesondere auch in dünnen Schichten im Bereich von 0.1 bis 1 mm. Bevorzugt enthält die Epoxidharz- Zusammensetzung dabei mindestens ein Amin der Formel (I) im Aminhärter, wie vorgängig beschrieben. In a preferred embodiment of the invention, the epoxy resin composition has a viscosity at 12 ° C of less than 2,800 mPa s, preferably less than 2,400 mPa s, in particular less than 2,300 mPa s, 5 minutes after mixing the components , determined using a plate-plate viscometer with a plate diameter of 50 mm, a plate-plate distance of 0.5 mm and a shear rate of 100 s -1 , based on the entire epoxy resin composition, in particular less than 10% by weight of thinner with a boiling point at normal pressure of at least 180 ° C and in particular less than 5% by weight of reactive diluents containing epoxy groups. Such a composition is particularly low in emissions and can be easily applied even in cool ambient conditions, especially in thin layers in the range of 0.1 to 1 mm. The epoxy resin composition preferably contains at least one amine of the formula (I) in the amine hardener, as described above.
Die vermischte Zusammensetzung wird innerhalb der Verarbeitungszeit bevorzugt flächig als dünner Film mit einer Schichtdicke von typischerweise etwa 50 pm bis etwa 5 mm, bevorzugt 0.1 bis 3 mm, auf ein Substrat appliziert, typischerweise bei Umgebungstemperatur, insbesondere im Bereich von etwa 5 bis 45°C, bevorzugt 10 bis 35°C. Die Applikation erfolgt insbesondere durch Aufgiessen auf das zu beschichtende Substrat und anschliessendem gleichmässigem Verteilen mit beispielsweise einem Pinsel, einer Rolle, einer Walze, einem Rakel oder einer Zahntraufel. Die Applikation kann auch als Spritzapplikation erfolgen. Within the processing time, the mixed composition is preferably applied flatly as a thin film with a layer thickness of typically about 50 μm to about 5 mm, preferably 0.1 to 3 mm, onto a substrate, typically at ambient temperature, in particular in the range of about 5 to 45 ° C , preferably 10 to 35°C. The application is carried out in particular by pouring it onto the substrate to be coated and then spreading it evenly with, for example, a brush, a roller, a roller, a squeegee or a toothed trowel. The application can also be carried out as a spray application.
Aus der Verwendung der Epoxidharz-Zusammensetzung entsteht ein Artikel umfassend die ausgehärtete Zusammensetzung. The use of the epoxy resin composition results in an article comprising the cured composition.
Ein weiterer Gegenstand der Erfindung ist eine Methode zum Beschichten umfassend die Schritte
a) Vermischen der Komponenten der beschriebenen Epoxidharz-Zusammensetzung, b) Applizieren der vermischten Zusammensetzung auf mindestens ein Substrat, insbesondere einen Boden, insbesondere in einer Schichtdicke im Bereich von 0.1 bis 3 mm, c) Aushärten lassen der applizierten Beschichtung bei Umgebungsbedingungen, insbesondere bei einer Temperatur im Bereich von 5 bis 45°C. Another subject of the invention is a method for coating comprising the following steps a) mixing the components of the described epoxy resin composition, b) applying the mixed composition to at least one substrate, in particular a floor, in particular in a layer thickness in the range from 0.1 to 3 mm, c) allowing the applied coating to harden under ambient conditions, in particular at a temperature in the range of 5 to 45°C.
Das Vermischen in Schritt a) kann kontinuierlich oder batchweise erfolgen. Bevorzugt ist ein batchweises Vermischen in einem offenen Gefäss mittels einem Rührwerk bis zum Erhalt einer makroskopisch homogenen Flüssigkeit. The mixing in step a) can be carried out continuously or batchwise. Mixing in batches in an open vessel using an agitator is preferred until a macroscopically homogeneous liquid is obtained.
Das Applizieren in Schritt b) erfolgt bevorzugt mittels Aufgiessen auf das Substrat und anschliessendem gleichmässigem Verteilen, insbesondere mittels Pinsel, Rolle, Walze, Rakel oder Zahntraufel. Dabei muss darauf geachtet werden, dass die Applikation innerhalb derjenigen Zeitspanne erfolgt, innerhalb welcher die vermischte Zusammensetzung eine für die Applikation geeignete Viskosität aufweist, wobei eine niedrige Viskosität die Applikation erleichtert. Diese für die Verarbeitung geeignete Zeitspanne wird auch als "Verarbeitungszeit" bezeichnet. The application in step b) is preferably carried out by pouring onto the substrate and then evenly distributing, in particular using a brush, roller, roller, squeegee or toothed trowel. Care must be taken to ensure that the application takes place within the period of time within which the mixed composition has a viscosity suitable for the application, with a low viscosity making the application easier. This period of time suitable for processing is also referred to as "processing time".
Als Substrat geeignet sind insbesondere die bereits genannten, wobei das Substrat bevorzugt als Boden vorliegt. Bevorzugte Substrate sind Beton, Mörtel, Zementestrich, Faserzement, Backstein, Ziegel, Gips, Naturstein, Asphalt, Bitumen, PCC (Polymermodifizierter Zementmörtel), ECO (Epoxidharz-modifizierter Zementmörtel), Holz, mit Harzen gebundene Holzwerkstoffe, Harz-Texti I-Verbundwerkstoffe, Kunststoffe, faserverstärkte Kunststoffe, lackierte Fliesen, gestrichener Beton oder beschichtete Böden aller Art. Those already mentioned are particularly suitable as substrates, with the substrate preferably being in the form of a soil. Preferred substrates are concrete, mortar, cement screed, fiber cement, brick, brick, plaster, natural stone, asphalt, bitumen, PCC (polymer-modified cement mortar), ECO (epoxy resin-modified cement mortar), wood, wood materials bound with resins, resin-Texti I composite materials , plastics, fiber-reinforced plastics, painted tiles, painted concrete or coated floors of all kinds.
Die Schritte a), b) und c) erfolgen bevorzugt alle bei Umgebungstemperaturen, insbesondere bei 5 bis 45 °C, besonders bevorzugt bei 5 bis 30 °C. Steps a), b) and c) are preferably all carried out at ambient temperatures, in particular at 5 to 45 ° C, particularly preferably at 5 to 30 ° C.
Die Epoxidharz-Zusammensetzung ist insbesondere Bestandteil eines Bodenbelages umfassend The epoxy resin composition is, in particular, a component of a floor covering
- gegebenenfalls eine Egalisierungsschicht, - if necessary, a leveling layer,
- gegebenenfalls eine Haftgrundierung, - if necessary, an adhesive primer,
- gegebenenfalls eine Abdichtungsschicht,
- eine oder mehrere Lagen einer Basisschicht, welche gegebenenfalls mit Quarzsand abgestreut ist, - if necessary, a sealing layer, - one or more layers of a base layer, which is optionally sprinkled with quartz sand,
- und gegebenenfalls eine Versiegelung (Top Coat). - and if necessary a seal (top coat).
Die erfindungsgemässe Epoxidharz-Zusammensetzung kann dabei die Haftgrundierung und/oder die Egalisierungsschicht und/oder die Abdichtungsschicht und/oder die Basisschicht und/oder die Versiegelung des Bodenbelags darstellen. Bei weiteren, nicht der erfindungsgemässen Epoxidharz-Zusammensetzung entsprechenden Schichten kann es sich ebenfalls um eine Epoxidharz- Zusammensetzungen handeln, oder um ein anderes Material, insbesondere eine Polyurethan- oder Polyharnstoff-Beschichtung, oder um Bitumen oder Asphalt. The epoxy resin composition according to the invention can represent the adhesive primer and/or the leveling layer and/or the sealing layer and/or the base layer and/or the sealing of the floor covering. Further layers that do not correspond to the epoxy resin composition according to the invention can also be an epoxy resin composition, or another material, in particular a polyurethane or polyurea coating, or bitumen or asphalt.
In einer bevorzugten Ausführungsform der Erfindung wird die erfindungsgemässe Epoxidharz-Zusammensetzung verwendet als Bestandteil eines Bodenschutzsystems, bei welchem die erfindungsgemässe Epoxidharz-Zusammensetzung die Basisschicht und/oder die Versiegelung darstellt. Bevorzugt ist die Basisschicht dabei mit Quarzsand abgestreut. Ein solches Bodenschutzsystem wird insbesondere in Industriehallen, Lagerhallen, Kühlräumen oder Kellern, oder auf Baikonen, Terrassen, Parkdecks oder Brücken eingesetzt. In a preferred embodiment of the invention, the epoxy resin composition according to the invention is used as a component of a soil protection system in which the epoxy resin composition according to the invention represents the base layer and/or the seal. The base layer is preferably sprinkled with quartz sand. Such a floor protection system is used in particular in industrial halls, warehouses, cold rooms or cellars, or on balconies, terraces, parking decks or bridges.
In einer weiteren bevorzugten Ausführungsform der Erfindung wird die Epoxidharz- Zusammensetzung verwendet als Bestandteil eines Bodenschutzsystemes, bei welchem die erfindungsgemässe Epoxidharz-Zusammensetzung eine Abdichtungsschicht darstellt, welche mit Bitumen und anschliessend mit Asphalt überschichtet ist. Bevorzugt ist die Abdichtungsschicht dabei mit Quarzsand abgestreut. Ein solches Bodenschutzsystem wird insbesondere auf Brücken eingesetzt. Dabei schützt die erfindungsgemässe Epoxidharz-Zusammensetzung die untenliegende Brückenkonstruktion vor eindringender Feuchtigkeit und somit vor Korrosion. In a further preferred embodiment of the invention, the epoxy resin composition is used as a component of a soil protection system, in which the epoxy resin composition according to the invention represents a sealing layer which is covered with bitumen and then with asphalt. The sealing layer is preferably sprinkled with quartz sand. Such a soil protection system is used in particular on bridges. The epoxy resin composition according to the invention protects the underlying bridge structure from moisture penetration and thus from corrosion.
Ein weiterer Gegenstand der Erfindung ist ein Bodenschutzsystem, umfassend i) mindestens eine Schicht der erfindungsgemässen Epoxidharz-Zusammensetzung in einer Schichtdicke von 0.1 bis 3 mm, ii) Quarzsand, welcher in und/oder auf, insbesondere auf, die Epoxidharz- Zusammensetzung i) gestreut wurde,
iii) gegebenenfalls mindestens eine weitere Schicht der erfindungsgemässen Epoxidharz-Zusammensetzung, welche insbesondere in einer Schichtdicke von 0.1 bis 1 mm auf die mit Sand abgestreute Schicht appliziert ist, iv) gegebenenfalls mindestens eine Schicht Bitumen, welche auf die Epoxidharz- Zusammensetzung i) oder iii) appliziert ist, und v) gegebenenfalls mindestens eine Schicht Asphalt, welche auf die Bitumenschicht appliziert ist. A further subject of the invention is a soil protection system comprising i) at least one layer of the epoxy resin composition according to the invention in a layer thickness of 0.1 to 3 mm, ii) quartz sand which is scattered in and/or on, in particular on, the epoxy resin composition i). became, iii) optionally at least one further layer of the epoxy resin composition according to the invention, which is applied in particular in a layer thickness of 0.1 to 1 mm on the layer sprinkled with sand, iv) optionally at least one layer of bitumen, which is applied to the epoxy resin composition i) or iii ) is applied, and v) optionally at least one layer of asphalt which is applied to the bitumen layer.
Für den Fall, dass die Schichten iv) und v) nicht Bestandteil des Bodenschutzsystems sind, ist Schicht iii) bevorzugt vorhanden und bildet die Versiegelung und somit die oberste Schicht bzw. Oberfläche des Bodenschutzsystems. In the event that layers iv) and v) are not part of the soil protection system, layer iii) is preferably present and forms the seal and thus the top layer or surface of the soil protection system.
Für den Fall, dass die Schichten iv) und v) Bestandteil des Bodenschutzsystems sind, ist das Bodenschutzsystem bevorzugt auf einer Brücke appliziert und die erfindungsgemässe Epoxidharz-Zusammensetzung dient als Abdichtung, welche die untenliegende Brückenkonstruktion vor eindringendem Wasser und somit vor Korrosion schützt. Bevorzugt ist dabei Schicht iii) ebenfalls vorhanden und Schicht iv) ist somit auf die Epoxidharz-Zusammensetzung iii) appliziert. In the event that layers iv) and v) are part of the soil protection system, the soil protection system is preferably applied to a bridge and the epoxy resin composition according to the invention serves as a seal, which protects the underlying bridge structure from penetrating water and thus from corrosion. Layer iii) is preferably also present and layer iv) is thus applied to the epoxy resin composition iii).
Das Bodenschutzsystem ist besonders nachhaltig, einfach applizierbar und ermöglicht einen technisch hochwertigen und langlebigen Schutz bei optisch ansprechender Erscheinung. Der Gehalt an petrobasiertem Bindemittel und Verdünnern und somit der CO2-Fussabdruck ist dabei besonders gering. The floor protection system is particularly sustainable, easy to apply and enables technically high-quality and long-lasting protection with a visually appealing appearance. The content of petro-based binders and thinners and therefore the CO2 footprint is particularly low.
Beispiele Examples
Im Folgenden sind Ausführungsbeispiele aufgeführt, welche die beschriebene Erfindung näher erläutern sollen. Selbstverständlich ist die Erfindung nicht auf diese beschriebenen Ausführungsbeispiele beschränkt. Examples of embodiments are listed below, which are intended to explain the invention described in more detail. Of course, the invention is not limited to these described exemplary embodiments.
Als „Normklima“ wird eine Temperatur von 23±1°C und eine relative Luftfeuchtigkeit von 50±5% bezeichnet. A “standard climate” is a temperature of 23 ± 1°C and a relative humidity of 50 ± 5%.
„EEW“ steht für das Epoxid-Equivalentgewicht. “EEW” stands for epoxy equivalent weight.
„AHEW“ steht für das Aminwasserstoff-Equivalentgewicht. “AHEW” stands for amine hydrogen equivalent weight.
Verwendete Substanzen:
Epoxid-Flüssigharz 1 Bisphenol A-Diglycidylether, EEW ca. 187 g/Eq (Araldit® GY-250, von Huntsman) Substances used: Epoxy liquid resin 1 bisphenol A diglycidyl ether, EEW approx. 187 g/eq (Araldit® GY-250, from Huntsman)
Epoxid-Flüssigharz 2 1 :1 Mischung Bisphenol A-Diglycidylether und Bisphenol F-Diglycidylether, EEW ca. 177 g/Eq (Epikote® Resin 05447, von Hexion)Epoxy liquid resin 2 1:1 mixture of bisphenol A diglycidyl ether and bisphenol F diglycidyl ether, EEW approx. 177 g/eq (Epikote® Resin 05447, from Hexion)
Reaktivverdünner Monoglycidylether von Ci2-14-Alkoholen, EEW ca. 294 g/Eq (Grilonit® Epoxide 8, von Ems Chemie)Reactive diluent monoglycidyl ether of Ci2-14 alcohols, EEW approx. 294 g/eq (Grilonit® Epoxide 8, from Ems Chemie)
Diisopropylnaphthalin Ruetasolv® DI (von Rütgers) Diisopropylnaphthalene Ruetasolv® DI (from Rütgers)
Entlüfter BYK-054 (von BYK) Breather BYK-054 (from BYK)
Benzylalkohol (von Valtris) Benzyl alcohol (from Valtris)
IPDA Isophorondiamin, AHEW 42.6 g/Eq (Vestamin® IPD, von Evonik) IPDA isophoronediamine, AHEW 42.6 g/Eq (Vestamin® IPD, from Evonik)
TEPA Tetraethylenpentamin, AHEW ca. 30 g/Eq (technisch, von Huntsman) TEPA tetraethylenepentamine, AHEW approx. 30 g/eq (technical, from Huntsman)
N-Benzyl-1 ,2-ethandiamin AHEW 50.1 g/Eq, hergestellt wie nachfolgend beschrieben N-Benzyl-1,2-ethanediamine AHEW 50.1 g/eq, prepared as described below
MXDA 1 ,3-Bis(aminomethyl)benzol, AHEW 34 g/Eq (von Mitsubishi Gas Chemical) MXDA 1,3-Bis(aminomethyl)benzene, AHEW 34 g/Eq (from Mitsubishi Gas Chemical)
Polyetherdiamin Polyoxypropylendiamin, AHEW 60 g/mol (Jeffamine® D-230, von Huntsman) Polyetherdiamine Polyoxypropylenediamine, AHEW 60 g/mol (Jeffamine® D-230, from Huntsman)
Ancamine® K54 2,4,6-T ris(dimethylaminomethyl)phenol (von Evonik) Ancamine® K54 2,4,6-Tris(dimethylaminomethyl)phenol (from Evonik)
Olivenkerne < 100 pm Olivenkerne aus der Gewinnung von Olivenöl, getrocknet, gemahlen, Partikelgrösse < 100 pm, Ligningehalt > 20 Gew.-% (von Micronizados Vegetales S.L) Olive pits < 100 pm Olive pits from the production of olive oil, dried, ground, particle size < 100 pm, lignin content > 20% by weight (from Micronizados Vegetales S.L)
Olivenkerne 300-600 pm Olivenkerne aus der Gewinnung von Olivenöl, getrocknet, gemahlen, Partikelgrösse 300-600 pm (von Micronizados Vegetales S.L) Olive kernels 300-600 pm Olive kernels from the production of olive oil, dried, ground, particle size 300-600 pm (from Micronizados Vegetales S.L)
Olivenkerne 600-800 pm Olivenkerne aus der Gewinnung von Olivenöl, getrocknet, gemahlen, Partikelgrösse 600-800 pm (von Micronizados Vegetales S.L)Olive kernels 600-800 pm Olive kernels from the production of olive oil, dried, ground, particle size 600-800 pm (from Micronizados Vegetales S.L)
Pecanschalen < 200 pm gemahlene Schalen von Pecannüssen, Partikelgrösse < 200 pm, Ligningehalt > 25 Gew.-% (von Composition Materials Co.) Pecan shells < 200 pm ground pecan shells, particle size < 200 pm, lignin content > 25 wt.% (from Composition Materials Co.)
Walnussschalen < 200 pm gemahlene Schalen von Walnüssen, Partikelgrösse < 200 pm, Ligningehalt > 15 Gew.-% (von Composition Materials Co.)
Reishülsen 1-30 pm Reishülsen, gemahlen, Ligningehalt < 5 Gew.-% (von Composition Materials Co.) Walnut shells < 200 pm ground walnut shells, particle size < 200 pm, lignin content > 15 wt.% (from Composition Materials Co.) Rice husks 1-30 pm rice husks, ground, lignin content < 5% by weight (from Composition Materials Co.)
Quarzmehl < 70 pm Dorsilit® 10.000 (von Dorfner) Quartz powder < 70 pm Dorsilit® 10,000 (from Dorfner)
Herstellung von N-Benzyl-1,2-ethandiamin: Preparation of N-Benzyl-1,2-ethanediamine:
180.3 g (3 mol) 1 ,2-Ethandiamin wurden bei Raumtemperatur vorgelegt, mit einer Lösung aus 106.0 g (1 mol) Benzaldehyd in 1200 ml Isopropanol vermischt und 2 Stunden gerührt, anschliessend bei 80°C, 80 bar Wasserstoff-Druck und einem Fluss von 5 ml/min auf einer kontinuierlich arbeitenden Hydrierapparatur mit Pd/C- Festbettkatalysator hydriert und die hydrierte Lösung am Rotationsverdampfer bei 65°C eingeengt, wobei unreagiertes 1 ,2-Ethandiamin, Wasser und Isopropanol entfernt wurden. Die so erhaltene Reaktionsmischung wurde bei 80°C unter Vakuum mittels Destillation gereinigt. Erhalten wurde eine farblose Flüssigkeit mit einem mittels GC bestimmten Gehalt an N-Benzyl-1 ,2-ethandiamin von > 97%. 180.3 g (3 mol) of 1,2-ethanediamine were placed at room temperature, mixed with a solution of 106.0 g (1 mol) of benzaldehyde in 1200 ml of isopropanol and stirred for 2 hours, then at 80 ° C, 80 bar hydrogen pressure and a Flow of 5 ml/min was hydrogenated on a continuously operating hydrogenation apparatus with a Pd/C fixed bed catalyst and the hydrogenated solution was concentrated on a rotary evaporator at 65° C., unreacted 1,2-ethanediamine, water and isopropanol being removed. The reaction mixture thus obtained was purified by distillation at 80° C. under vacuum. A colorless liquid was obtained with an N-benzyl-1,2-ethanediamine content of >97%, determined by GC.
Herstellung von Epoxidharz-Zusammensetzungen: Production of epoxy resin compositions:
Zusammensetzungen Z-1 bis Z-9: Compositions Z-1 to Z-9:
Zur Herstellung der Zusammensetzungen wurden die in der Tabelle 1 angegebenen Inhaltsstoffe der Harz-Komponente in den angegebenen Mengen (in Gewichtsteilen) mit einem Dissolver vermischt und in einem verschlossenen Gebinde gelagert. To produce the compositions, the resin component ingredients listed in Table 1 were mixed in the specified amounts (in parts by weight) with a dissolver and stored in a sealed container.
Die in der Tabelle 1 angegebenen Inhaltsstoffe der Härter-Komponente wurden mit Hilfe eines Magnetrührers vermischt und in einem verschlossenen Gebinde gelagert. The ingredients of the hardener component listed in Table 1 were mixed using a magnetic stirrer and stored in a sealed container.
Die mit "(Ref.)" bezeichneten Zusammensetzungen sind nicht-erfindungsgemässe Zusammensetzungen und dienen als Vergleich. The compositions designated "(Ref.)" are compositions not according to the invention and serve as a comparison.
Dispergierbarkeit: Dispersibility:
Die Dispergierbarkeit des eingesetzten Granulats wurde bei der Herstellung der Harz- Komponente mittels Dissolver beurteilt. Eine gleichmässige Verteilung der Inhaltsstoffe nach kurzer Mischzeit wurde mit "+" bewertet. Eine gleichmässige Verteilung der Inhaltsstoffe erst nach längerer Mischzeit wurde mit "+/-" bewertet. Konnte keine gleichmässige Verteilung der Inhaltsstoffe erhalten werden, wurde dies mit "-" bewertet. Die Resultate sind in der Tabelle 1 ersichtlich.
Viskosität der Harz-Komponente: The dispersibility of the granules used was assessed using a dissolver during the production of the resin component. An even distribution of the ingredients after a short mixing time was rated “+”. An even distribution of the ingredients only after a longer mixing time was rated as “+/-”. If an even distribution of the ingredients could not be achieved, this was rated as “-”. The results can be seen in Table 1. Resin component viscosity:
Eine Stunde nach dem Vermischen der Inhaltsstoffe der Harz-Komponente wurde die Viskosität der Harz-Komponente bei 23°C auf einem thermostatisierten Platte-Platte- Viskosimeter MCR 102E (Anton Paar) (Plattendurchmesser 50 mm, Platte- Platte- Abstand 0.5 mm, Scherrate 100 s-1) bestimmt. Die Resultate sind in der Tabelle 1 ersichtlich. One hour after mixing the ingredients of the resin component, the viscosity of the resin component was measured at 23 ° C on a thermostat plate-plate viscometer MCR 102E (Anton Paar) (plate diameter 50 mm, plate-plate distance 0.5 mm, shear rate 100 s -1 ). The results can be seen in Table 1.
Redisperqierbarkeit: Redisperability:
Die Inhaltsstoffe der Harz-Komponente wurden wie beschrieben mit einem Dissolver vermischt. 1 kg der so gemischten Harz-Komponente wurde anschliessend in einem verschlossenen Gebinde während 14 Tagen bei 45°C auf einem Rütteltisch gelagert. Danach wurde der in der Harz-Komponente entstandene Bodensatz mittels dem Dissolver erneut aufgerührt. Falls der Bodensatz nach kurzer Mischzeit wieder gleichmässig in der Harz-Komponente verteilt werden konnte, wurde die Redispergierbarkeit mit "+" bewertet, konnte hingegen nach kurzer Mischzeit keine gleichmässige Verteilung erreicht werden, wurde die Redispergierbarkeit mit "-" bewertet. Die Resultate sind in der Tabelle 1 ersichtlich. The ingredients of the resin component were mixed with a dissolver as described. 1 kg of the resin component mixed in this way was then stored in a sealed container on a shaking table at 45 ° C for 14 days. The sediment formed in the resin component was then stirred again using the dissolver. If the sediment could be evenly distributed again in the resin component after a short mixing time, the redispersibility was rated as "+", whereas if an even distribution could not be achieved after a short mixing time, the redispersibility was rated as "-". The results can be seen in Table 1.
Für die folgenden Prüfungen wurden die Harz- und die Härter-Komponente im in Tabelle 1 angegebenen Gewichtsverhältnis mittels einem Bohrmaschinen-Rührwerk vermischt. For the following tests, the resin and hardener components were mixed in the weight ratio shown in Table 1 using a drill agitator.
Oberflächenbeschaffenheit: Surface texture:
Die frisch vermischte Zusammensetzung wurde in einer Menge von 0.5 g/m2 mit Hilfe einer Walze auf eine Betonplatte appliziert und 7 Tage im Normklima gelagert. The freshly mixed composition was applied to a concrete slab in an amount of 0.5 g/m 2 using a roller and stored in a standard climate for 7 days.
Anschliessend wurde die Oberflächenbeschaffenheit visuell beurteilt. Keine sichtbaren Unebenheiten auf der Oberfläche der Platte wurde mit "+" bewertet, von Auge deutlich feststellbare Unebenheiten wurde mit "-" bewertet. Die Resultate sind in der Tabelle 1 ersichtlich. The surface quality was then assessed visually. No visible unevenness on the surface of the plate was rated as "+", unevenness that was clearly visible to the eye was rated as "-". The results can be seen in Table 1.
Mischviskosität: Mixing viscosity:
5 min nach dem Vermischen der Harz- und der Härter-Komponente wurde die Viskosität bei 23°C auf einem thermostatisierten Platte-Platte-Viskosimeter MCR 102E (Anton Paar) (Plattendurchmesser 50 mm, Platte-Platte-Abstand 0.5 mm, Scherrate
100 s-1) bestimmt. Die erfindungsgemässen Zusammensetzungen Z-1 und Z-6 bis Z-8 wiesen alle eine Viskosität im Bereich von 0.4 bis 2 Pa s auf.
5 minutes after mixing the resin and hardener components, the viscosity was measured at 23 ° C on a thermostatized plate-plate viscometer MCR 102E (Anton Paar) (plate diameter 50 mm, plate-plate distance 0.5 mm, shear rate 100 s-1). The compositions Z-1 and Z-6 to Z-8 according to the invention all had a viscosity in the range from 0.4 to 2 Pa s.
Tabelle 1 : Zusammensetzung und Eigenschaften von Z-1 bis Z-9 "n.b." steht für "nicht bestimmt"
Table 1: Composition and properties of Z-1 to Z-9 "nb" stands for "not determined"
Tabelle 1 : (Forsetzung) Table 1: (continued)
Zusammensetzungen Z-10 bis Z-15: Die Zusammensetzungen wurden gemäss den in Tabelle 2 angegebenen Inhaltsstoffe der Harz-Komponente und der Härter-Komponente wie für Zusammensetzung Z-1 beschrieben hergestellt. Compositions Z-10 to Z-15: The compositions were prepared according to the ingredients of the resin component and the hardener component given in Table 2 as described for composition Z-1.
Die Disperqierbarkeit und die Redisperqierbarkeit der Harz-Komponente wurden wie für Zusammensetzung Z-1 beschrieben bestimmt. The dispersibility and redispersibility of the resin component were determined as described for Composition Z-1.
Für die folgenden Prüfungen wurden die Harz- und die Härter-Komponente im in Tabelle 2 angegebenen Gewichtsverhältnis mittels einem Bohrmaschinen-Rührwerk vermischt.
Die Mischviskosität wurde 5 min nach dem Vermischen der Harz- und der Härter- Komponente bei 12°C bzw. bei 20°C auf einem therm ostatisierten Platte- Platte- Viskosimeter (Plattendurchmesser 50 mm, Platte-Platte-Abstand 0.5 mm, Scherrate 100 s-1) bestimmt. For the following tests, the resin and hardener components were mixed in the weight ratio shown in Table 2 using a drill agitator. The mixed viscosity was measured 5 minutes after mixing the resin and hardener components at 12 ° C or at 20 ° C on a thermostatized plate-plate viscometer (plate diameter 50 mm, plate-plate distance 0.5 mm, shear rate 100 s-1) determined.
Die Oberflächenbeschaffenheit wurde wie für Zusammensetzung Z-1 beschrieben geprüft. The surface finish was tested as described for Composition Z-1.
Die Shore D Härte wurde gemäss DIN 53505 an zwei zylindrischen Prüfkörpern (Durchmesser 20 mm, Dicke 5 mm) bestimmt, wobei einer bei 8°C und einer bei 23°C gelagert und die Härte jeweils nach der angegebenen Zeit gemessen wurde. The Shore D hardness was determined according to DIN 53505 on two cylindrical test specimens (diameter 20 mm, thickness 5 mm), one stored at 8 ° C and one at 23 ° C and the hardness was measured after the specified time.
Die Resultate sind in der Tabelle 2 angegeben. The results are given in Table 2.
Die mit "(Ref.)" bezeichneten Zusammensetzungen sind nicht-erfindungsgemässe Zusammensetzungen und dienen als Vergleich. The compositions designated "(Ref.)" are compositions not according to the invention and serve as a comparison.
Aus der Tabelle 2 ist ersichtlich, dass eine Zusammensetzung mit einem Härter enthaltend N-Benzyl-1 ,2-ethandiamin und einem erfindungsgemässen biobasierten Granulat eine überraschend niedrige Viskosität, insbesondere bei 12 °C, aufweist (Z-10 im Vergleich zu Z-11 ), während bei entsprechenden Zusammensetzungen mit N- Benzyl-1 ,2-ethandiamin im Härter und Quarzmehl anstelle des biobasierten Granulats dieser Viskositätsvorteil nicht besteht (Z-12 (Ref.) im Vergleich zu Z-13 (Ref.)).
From Table 2 it can be seen that a composition with a hardener containing N-benzyl-1,2-ethanediamine and a bio-based granulate according to the invention has a surprisingly low viscosity, especially at 12 ° C (Z-10 in comparison to Z-11 ), while with corresponding compositions with N-benzyl-1,2-ethanediamine in the hardener and quartz powder instead of the bio-based granules, this viscosity advantage does not exist (Z-12 (Ref.) compared to Z-13 (Ref.)).
Tabelle 2: Zusammensetzung und Eigenschaften von Z-10 bis Z-15 "n.b." steht für "nicht bestimmt"
Table 2: Composition and properties of Z-10 to Z-15 "n.b." stands for "not determined"
Claims
Patentansprüche: Patent claims:
1. Epoxidharz-Zusammensetzung umfassend 1. Epoxy resin composition comprising
- eine Harz-Komponente enthaltend mindestens ein Epoxid-Flüssigharz,- a resin component containing at least one epoxy liquid resin,
- eine Härter-Komponente enthaltend mindestens einen Aminhärter, und - a hardener component containing at least one amine hardener, and
- mindestens ein biobasiertes Granulat mit einer Partikelgrösse < 200 pm und einem Ligningehalt von mindestens 10 Gew.-%, bevorzugt mindestens 15 Gew.-%, wobei das biobasierte Granulat Teil der Harz- und/oder der Härter-Komponente ist und der Gehalt an biobasiertem Granulat bezogen auf die gesamte Epoxidharz-Zusammensetzung 1 bis 40 Gew.-%, bevorzugt 2 bis 30 Gew.-%, insbesondere 5 bis 25 Gew.-%, beträgt. - at least one bio-based granulate with a particle size <200 pm and a lignin content of at least 10% by weight, preferably at least 15% by weight, the bio-based granulate being part of the resin and/or the hardener component and the content of bio-based granules based on the entire epoxy resin composition is 1 to 40% by weight, preferably 2 to 30% by weight, in particular 5 to 25% by weight.
2. Zusammensetzung gemäss Anspruch 1 , dadurch gekennzeichnet, dass die Harz- Komponente und die Härter-Komponente getrennt voneinander vorliegen. 2. Composition according to claim 1, characterized in that the resin component and the hardener component are present separately from one another.
3. Zusammensetzung gemäss einem der vorgehenden Ansprüche, dadurch gekennzeichnet, dass das biobasierte Granulat einen Feuchtigkeitsgehalt von weniger als 15 Gew.-%, bevorzugt weniger als 12 Gew.-%, aufweist. 3. Composition according to one of the preceding claims, characterized in that the bio-based granules have a moisture content of less than 15% by weight, preferably less than 12% by weight.
4. Zusammensetzung gemäss einem der vorgehenden Ansprüche, dadurch gekennzeichnet, dass das biobasierte Granulat ausgewählt ist aus der Gruppe bestehend aus gemahlenen Olivenkernen, Kokosnussschalen, Mandelschalen, Walnussschalen, Pecannussschalen, Paranussschalen, Haselnussschalen, Macadamianussschalen, Cashewnussschalen, Pistazienschalen, Kakaofruchtschalen, Aprikosenkernschalen, Pfirsichkernschalen und Zwetschgenkernschalen. 4. Composition according to one of the preceding claims, characterized in that the bio-based granules are selected from the group consisting of ground olive kernels, coconut shells, almond shells, walnut shells, pecan shells, Brazil nut shells, hazelnut shells, macadamia nut shells, cashew nut shells, pistachio shells, cocoa fruit shells, apricot kernel shells, peach kernel shells and Plum seed peels.
5 Zusammensetzung gemäss einem der vorgehenden Ansprüche, dadurch gekennzeichnet, dass das biobasierte Granulat ein Granulat aus Olivenkernen ist. 5 Composition according to one of the preceding claims, characterized in that the bio-based granules are granules made from olive stones.
6. Zusammensetzung gemäss einem der vorgehenden Ansprüche, dadurch gekennzeichnet, dass der Aminhärter mindestens ein aliphatisches, cycloaliphatisches oder arylaliphatisches Di- oder Triamin mit mindestens 3 Aminwasserstoffen enthält, insbesondere ausgewählt aus der Liste bestehend aus 2-Butyl-2-ethyl-1 ,5-pentandiamin, 2,2(4),4-Trimethylhexamethylendiamin, 1 ,2-
Diaminocyclohexan, Bis(4-aminocyclohexyl)methan, Isophorondiamin, 1 ,3- Bis(aminomethyl)cyclohexan, 1 ,4-Bis(aminomethyl)cyclohexan, 2(4)-Methyl-1 ,3- diaminocyclohexan, 2,5(2,6)-Bis(aminomethyl)bicyclo[2.2.1]heptan, 1 ,3- Bis(aminomethyl)benzol, Polyoxypropylendiaminen mit mittlerem Molekulargewicht Mn von 200 bis 500 g/mol, Polyoxypropylentriaminen mit mittlerem Molekulargewicht Mn von 300 bis 500 g/mol, 3-(3- (Dimethylamino)propylamino)propylamin, Bis(hexamethylen)triamin, Triethylentetramin, Tetraethylenpentamin, Pentaethylenhexamin N,N'-Bis(3- aminopropyl)ethylendiamin, N-Benzyl-1 ,2-ethandiamin, N-Furfuryl-1 ,2- ethandiamin, N-Tetrahydrofurfuryl-1 ,2-ethandiamin, N-Benzyl-1 , 3- bis(aminomethyl)benzol und aminfunktionellen Addukten dieser Amine mit aromatischen Diepoxiden. Zusammensetzung gemäss einem der vorgehenden Ansprüche, dadurch gekennzeichnet, dass der Aminhärter mindestens ein Amin der Formel (I) enthält, 6. Composition according to one of the preceding claims, characterized in that the amine hardener contains at least one aliphatic, cycloaliphatic or arylaliphatic diamine or triamine with at least 3 amine hydrogens, in particular selected from the list consisting of 2-butyl-2-ethyl-1,5 -pentanediamine, 2,2(4),4-trimethylhexamethylenediamine, 1,2- Diaminocyclohexane, bis(4-aminocyclohexyl)methane, isophoronediamine, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 2(4)-methyl-1,3-diaminocyclohexane, 2,5(2 ,6)-Bis(aminomethyl)bicyclo[2.2.1]heptane, 1,3-bis(aminomethyl)benzene, polyoxypropylene diamines with an average molecular weight M n of 200 to 500 g/mol, polyoxypropylene triamines with an average molecular weight M n of 300 to 500 g/mol, 3-(3-(dimethylamino)propylamino)propylamine, bis(hexamethylene)triamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine N,N'-bis(3-aminopropyl)ethylenediamine, N-benzyl-1,2-ethanediamine, N-Furfuryl-1,2-ethanediamine, N-tetrahydrofurfuryl-1,2-ethanediamine, N-benzyl-1,3-bis(aminomethyl)benzene and amine-functional adducts of these amines with aromatic diepoxides. Composition according to one of the preceding claims, characterized in that the amine hardener contains at least one amine of the formula (I),
NH2-A— NH— CH2-Y (l) wobei NH 2 -A— NH— CH 2 -Y (l) where
A für einen zweiwertigen Alkylen- oder Cycloalkylen-Rest mit 2 bis 8 C-Atomen steht, und A represents a divalent alkylene or cycloalkylene radical with 2 to 8 carbon atoms, and
Y für einen gegebenenfalls substituierten Phenyl-Rest mit 6 bis 12 C-Atomen, Furfuryl oder einen Naphthyl-Rest steht, wobei die beiden Stickstoffatome, an welche der Rest A gebunden ist, durch mindestens zwei C-Atome voneinander getrennt sind. Zusammensetzung gemäss Anspruch 7, dadurch gekennzeichnet, dass der Aminhärter zusätzlich zu mindestens einem Amin der Formel (I) mindestens ein weiteres Amin mit zwei primären Aminogruppen enthält, insbesondere ausgewählt aus der Gruppe bestehend aus Isophorondiamin, 1 ,3-Bis(aminomethyl)benzol,Y represents an optionally substituted phenyl radical with 6 to 12 carbon atoms, furfuryl or a naphthyl radical, the two nitrogen atoms to which the radical A is bonded being separated from one another by at least two carbon atoms. Composition according to claim 7, characterized in that the amine hardener contains, in addition to at least one amine of the formula (I), at least one further amine with two primary amino groups, in particular selected from the group consisting of isophoronediamine, 1,3-bis (aminomethyl) benzene,
1 ,3-Bis(aminomethyl)cyclohexan, 1 ,4-Bis(aminomethyl)cyclohexan, 2, 2(4), 4- Trimethylhexamethylendiamin, Bis(4-aminocyclohexyl)methan, 2(4)-Methyl-1 ,3- diaminocyclohexan und 2,5(2,6)-Bis(aminomethyl)bicyclo[2.2.1 ]heptan. Zusammensetzung gemäss einem der Ansprüche 7 oder 8, dadurch gekennzeichnet, dass der Aminhärter so viel Amin der Formel (I) enthält, dass 3 bis
40 %, bevorzugt 5 bis 30 %, insbesondere 6 bis 20 %, aller Aminwasserstoffe der Epoxidharz-Zusammensetzung vom Amin der Formel (I) stammen. 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 2, 2(4), 4-trimethylhexamethylenediamine, bis(4-aminocyclohexyl)methane, 2(4)-methyl-1,3- diaminocyclohexane and 2,5(2,6)-bis(aminomethyl)bicyclo[2.2.1]heptane. Composition according to one of claims 7 or 8, characterized in that the amine hardener contains so much amine of the formula (I) that 3 to 40%, preferably 5 to 30%, in particular 6 to 20%, of all amine hydrogens in the epoxy resin composition come from the amine of the formula (I).
10. Zusammensetzung gemäss einem der vorgehenden Ansprüche, dadurch gekennzeichnet, dass bezogen auf die gesamte Epoxidharz-Zusammensetzung weniger als 20 Gew.-%, insbesondere weniger als 15 Gew.-%, bevorzugt weniger als 10 Gew.-%, Verdünner mit einem Siedepunkt bei Normaldruck von mindestens 180 °C, insbesondere mindestens 200 °C, enthalten sind, vorzugsweise ausgewählt aus der Liste bestehend aus Benzylalkohol, 2- Phenoxyethanol, Cardanol, styrolisiertem Phenol, Diisopropylnaphthalin, Isopropylbiphenylen und phenolgruppenhaltigen aromatischen Kohlenwasserstoffharzen. 10. Composition according to one of the preceding claims, characterized in that, based on the entire epoxy resin composition, less than 20% by weight, in particular less than 15% by weight, preferably less than 10% by weight, of diluent with a boiling point at normal pressure of at least 180 ° C, in particular at least 200 ° C, are contained, preferably selected from the list consisting of benzyl alcohol, 2-phenoxyethanol, cardanol, styrenized phenol, diisopropylnaphthalene, isopropyl biphenyls and aromatic hydrocarbon resins containing phenol groups.
11 . Zusammensetzung gemäss einem der vorgehenden Ansprüche, dadurch gekennzeichnet, dass bezogen auf die gesamte Epoxidharz-Zusammensetzung der Gehalt an anorganischen Füllstoffen weniger als 5 Gew.-%, bevorzugt weniger als 2 Gew.-%, insbesondere weniger als 1 Gew.-%, beträgt. 11. Composition according to one of the preceding claims, characterized in that, based on the entire epoxy resin composition, the content of inorganic fillers is less than 5% by weight, preferably less than 2% by weight, in particular less than 1% by weight .
12. Zusammensetzung gemäss einem der vorgehenden Ansprüche, dadurch gekennzeichnet, dass mindestens ein oberflächenaktives Additiv ausgewählt aus Entschäumern und Entlüftern enthalten ist, insbesondere in einer Menge bezogen auf die gesamte Epoxidharz-Zusammensetzung von 0.01 bis 1 Gew.-%, bevorzugt 0.02 bis 0.5 Gew.-%. 12. Composition according to one of the preceding claims, characterized in that at least one surface-active additive selected from defoamers and deaerators is contained, in particular in an amount based on the total epoxy resin composition of 0.01 to 1% by weight, preferably 0.02 to 0.5% by weight .-%.
13. Ausgehärtete Zusammensetzung erhalten aus der Aushärtung der Epoxidharz- Zusammensetzung gemäss einem der Ansprüche 1 bis 12 nach dem Vermischen der Komponenten. 13. Cured composition obtained from curing the epoxy resin composition according to one of claims 1 to 12 after mixing the components.
14. Verwendung der Zusammensetzung gemäss einem der Ansprüche 1 bis 12 als Belag, Beschichtung, Egalisierung, Abdichtung oder Haftgrundierung, insbesondere als Bestandteil eines Bodenbelags. 14. Use of the composition according to one of claims 1 to 12 as a covering, coating, leveling, sealing or adhesive primer, in particular as a component of a floor covering.
15. Methode zum Beschichten umfassend die Schritte a) Vermischen der Komponenten der Epoxidharz-Zusammensetzung gemäss einem der Ansprüche 1 bis 12,
b) Applizieren der vermischten Zusammensetzung auf mindestens ein Substrat, insbesondere einen Boden, insbesondere in einer Schichtdicke im Bereich von 0.1 bis 3 mm, c) Aushärten lassen der applizierten Beschichtung bei Umgebungsbedingungen, insbesondere bei einer Temperatur im Bereich von 5 bis 45°C, besonders bevorzugt bei 5 bis 30 °C. Bodenschutzsystems, umfassend i) mindestens eine Schicht der Epoxidharz-Zusammensetzung gemäss einem der Ansprüche 1 bis 12 in einer Schichtdicke von 0.1 bis 3 mm, ii) Quarzsand, welcher in und/oder auf, insbesondere auf, die Epoxidharz- Zusammensetzung i) gestreut wurde, iii) gegebenenfalls mindestens eine weitere Schicht der Epoxidharz- Zusammensetzung gemäss einem der Ansprüche 1 bis 12, welche insbesondere in einer Schichtdicke von 0.1 bis 1 mm auf die mit Sand abgestreute Schicht appliziert ist, iv) gegebenenfalls mindestens eine Schicht Bitumen, welche auf die Epoxidharz- Zusammensetzung iii) appliziert ist, und v) gegebenenfalls mindestens eine Schicht Asphalt, welche auf die Bitumenschicht appliziert ist.
15. Method for coating comprising steps a) mixing the components of the epoxy resin composition according to one of claims 1 to 12, b) applying the mixed composition to at least one substrate, in particular a floor, in particular in a layer thickness in the range from 0.1 to 3 mm, c) allowing the applied coating to harden under ambient conditions, in particular at a temperature in the range from 5 to 45 ° C, particularly preferably at 5 to 30 °C. Soil protection system, comprising i) at least one layer of the epoxy resin composition according to one of claims 1 to 12 in a layer thickness of 0.1 to 3 mm, ii) quartz sand which was scattered in and/or on, in particular on, the epoxy resin composition i). , iii) optionally at least one further layer of the epoxy resin composition according to one of claims 1 to 12, which is applied in particular in a layer thickness of 0.1 to 1 mm to the layer sprinkled with sand, iv) optionally at least one layer of bitumen, which is applied to the Epoxy resin composition iii) is applied, and v) optionally at least one layer of asphalt, which is applied to the bitumen layer.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP22188606 | 2022-08-03 | ||
EP22188606.2 | 2022-08-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2024027960A1 true WO2024027960A1 (en) | 2024-02-08 |
Family
ID=82839074
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2023/059067 WO2024027960A1 (en) | 2022-08-03 | 2023-04-05 | Epoxy resin composition with bio-based granular material |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2024027960A1 (en) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008026266A1 (en) | 2008-06-02 | 2009-12-03 | Henkel Ag & Co. Kgaa | Molded body from granules of olive stones and crosslinked adhesive comprising reactive adhesive made of two-component epoxy adhesive, two- or one-component-polyurethane-adhesive, useful as floor covering and soundproofing molded body |
DE102011118507A1 (en) * | 2010-11-15 | 2012-05-16 | J. Rettenmaier & Söhne Gmbh + Co. Kg | Colored cellulose containing finely divided particles, which are coated or dyed with coloring agent in presence reactive binder, as thermosetting or elastomer layer, useful e.g. as additive e.g. for linoleum, dry mortar and concrete |
WO2015018466A1 (en) | 2013-04-05 | 2015-02-12 | Fischerwerke Gmbh & Co. Kg | Synthetic-resin adhesive having biogenic reactive diluents and resins |
WO2017037069A1 (en) | 2015-09-01 | 2017-03-09 | Sika Technology Ag | Low-emission epoxy resin composition |
-
2023
- 2023-04-05 WO PCT/EP2023/059067 patent/WO2024027960A1/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008026266A1 (en) | 2008-06-02 | 2009-12-03 | Henkel Ag & Co. Kgaa | Molded body from granules of olive stones and crosslinked adhesive comprising reactive adhesive made of two-component epoxy adhesive, two- or one-component-polyurethane-adhesive, useful as floor covering and soundproofing molded body |
DE102011118507A1 (en) * | 2010-11-15 | 2012-05-16 | J. Rettenmaier & Söhne Gmbh + Co. Kg | Colored cellulose containing finely divided particles, which are coated or dyed with coloring agent in presence reactive binder, as thermosetting or elastomer layer, useful e.g. as additive e.g. for linoleum, dry mortar and concrete |
WO2015018466A1 (en) | 2013-04-05 | 2015-02-12 | Fischerwerke Gmbh & Co. Kg | Synthetic-resin adhesive having biogenic reactive diluents and resins |
US20160060493A1 (en) * | 2013-04-05 | 2016-03-03 | Fischerwerke Gmbh & Co. Kg | Synthetic-resin adhesive compositions comprising biogenic reactive diluents and resins |
WO2017037069A1 (en) | 2015-09-01 | 2017-03-09 | Sika Technology Ag | Low-emission epoxy resin composition |
Non-Patent Citations (6)
Title |
---|
ISAM BAKR ALBAKER RUYA ET AL: "Application of various carboxylic acids modified walnut shell waste as natural filler for epoxy-based composites", JOURNAL OF APPLIED POLYMER SCIENCE, vol. 138, no. 31, 26 March 2021 (2021-03-26), US, pages 50770, XP093060887, ISSN: 0021-8995, Retrieved from the Internet <URL:https://onlinelibrary.wiley.com/doi/full-xml/10.1002/app.50770> DOI: 10.1002/app.50770 * |
MIRANDA ISABEL ET AL: "Valorization of lignocellulosic residues from the olive oil industry by production of lignin, glucose and functional sugars", BIORESOURCE TECHNOLOGY, ELSEVIER, AMSTERDAM, NL, vol. 292, 1 August 2019 (2019-08-01), XP085807800, ISSN: 0960-8524, [retrieved on 20190801], DOI: 10.1016/J.BIORTECH.2019.121936 * |
PAPANICOLAOU G. C. ET AL: "Effect of thermal fatigue on the mechanical properties of epoxy matrix composites reinforced with olive pits powder", JOURNAL OF APPLIED POLYMER SCIENCE, vol. 124, no. 1, 3 October 2011 (2011-10-03), US, pages 67 - 76, XP093018134, ISSN: 0021-8995, DOI: 10.1002/app.35092 * |
PAPANICOLAOU GEORGE C. ET AL: "Development of environmentally friendly epoxy and composite adhesives and applications in single and mixed-modulus joints", JOURNAL OF ADHESION SCIENCE AND TECHNOLOGY, vol. 35, no. 11, 27 October 2020 (2020-10-27), GB, pages 1138 - 1153, XP093018135, ISSN: 0169-4243, DOI: 10.1080/01694243.2020.1836787 * |
SAJITH S ET AL: "Comparison on mechanical properties of lignocellulosic flour epoxy composites prepared by using coconut shell, rice husk and teakwood as fillers", POLYMER TESTING, ELSEVIER, AMSTERDAM, NL, vol. 58, 14 December 2016 (2016-12-14), pages 60 - 69, XP029922255, ISSN: 0142-9418, DOI: 10.1016/J.POLYMERTESTING.2016.12.015 * |
SUTHAN R. ET AL: "Wear analysis of bio-fillers reinforced epoxy composites", MATERIALS TODAY: PROCEEDINGS, vol. 22, 1 January 2020 (2020-01-01), NL, pages 793 - 798, XP093060848, ISSN: 2214-7853, DOI: 10.1016/j.matpr.2019.10.154 * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3180383B1 (en) | Amine for low-emission epoxy resin compositions | |
EP3344677B1 (en) | Low-emission epoxy resin composition | |
EP2943464B1 (en) | Amine for low-emission epoxy resin products | |
EP3102561B1 (en) | Amine for low emission epoxy resin products | |
EP3180382B1 (en) | Amine for low-emission epoxy resin compositions | |
WO2017046292A1 (en) | Amine for low-emission epoxy resin compositions | |
EP3735433B1 (en) | Epoxy resin composition for coating applications | |
EP3350244B1 (en) | Hardener for low-emission epoxy resin compositions | |
WO2023006598A1 (en) | Amine hardener with high content in renewable carbon | |
WO2017025448A1 (en) | Amine for low-emission epoxy resin compositions | |
EP3344678B1 (en) | Amine for low-emission epoxy resin compositions | |
EP3252091B1 (en) | Tetrahydrofuran diamine | |
EP4208498A1 (en) | Electrically conductive epoxy resin coating and electrostatically dissipative floor | |
WO2024027960A1 (en) | Epoxy resin composition with bio-based granular material | |
WO2023094361A1 (en) | Epoxy resin composition with adjustable curing speed at different temperatures | |
WO2023072992A1 (en) | Mannich base with high content in renewable carbon | |
WO2023285188A1 (en) | Accelerator for epoxy resins | |
WO2023285255A1 (en) | Hardener for epoxy resins | |
WO2023247445A1 (en) | Solution of polyphenols in amine | |
EP4284853A1 (en) | Adduct of alkylated diamine and epoxy novolac resin | |
WO2023285189A1 (en) | Hardener for epoxy resins |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 23718224 Country of ref document: EP Kind code of ref document: A1 |