EP4069792A1 - Système hybride de durcissement par réaction de michael destiné à être utilisé dans une technologie de fixation chimique - Google Patents
Système hybride de durcissement par réaction de michael destiné à être utilisé dans une technologie de fixation chimiqueInfo
- Publication number
- EP4069792A1 EP4069792A1 EP20819664.2A EP20819664A EP4069792A1 EP 4069792 A1 EP4069792 A1 EP 4069792A1 EP 20819664 A EP20819664 A EP 20819664A EP 4069792 A1 EP4069792 A1 EP 4069792A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acrylate
- diacrylate
- hybrid system
- component
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000126 substance Substances 0.000 title claims description 13
- 238000005516 engineering process Methods 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 229920005989 resin Polymers 0.000 claims abstract description 29
- 239000011347 resin Substances 0.000 claims abstract description 29
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 15
- 238000000576 coating method Methods 0.000 claims abstract description 9
- 239000000853 adhesive Substances 0.000 claims abstract description 7
- 230000001070 adhesive effect Effects 0.000 claims abstract description 7
- 239000011248 coating agent Substances 0.000 claims abstract description 7
- 239000003973 paint Substances 0.000 claims abstract 2
- -1 hydroxyethyl- Chemical group 0.000 claims description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 29
- 230000000035 biogenic effect Effects 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 20
- 238000004873 anchoring Methods 0.000 claims description 16
- 150000003141 primary amines Chemical class 0.000 claims description 15
- 239000004593 Epoxy Substances 0.000 claims description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 239000004567 concrete Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 10
- 229920000728 polyester Polymers 0.000 claims description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 9
- 239000004615 ingredient Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 239000000470 constituent Substances 0.000 claims description 8
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 6
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004386 diacrylate group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229920000768 polyamine Polymers 0.000 claims description 6
- 229910000077 silane Inorganic materials 0.000 claims description 6
- 150000003512 tertiary amines Chemical group 0.000 claims description 6
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-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
- 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 5
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 5
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000003860 storage Methods 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 4
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 claims description 4
- BNYFUBOZYDQIDU-UHFFFAOYSA-N 3-[diethoxy(ethyl)silyl]propan-1-amine Chemical compound CCO[Si](CC)(OCC)CCCN BNYFUBOZYDQIDU-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 4
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 4
- 238000004040 coloring Methods 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- 150000002118 epoxides Chemical class 0.000 claims description 4
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 4
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 4
- 229920003986 novolac Polymers 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- RHNJVKIVSXGYBD-UHFFFAOYSA-N 10-prop-2-enoyloxydecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCOC(=O)C=C RHNJVKIVSXGYBD-UHFFFAOYSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 claims description 3
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 claims description 3
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 3
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 3
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 235000019438 castor oil Nutrition 0.000 claims description 3
- 239000004359 castor oil Substances 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004744 fabric Substances 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 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 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920000223 polyglycerol Polymers 0.000 claims description 3
- 150000004760 silicates Chemical class 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 3
- 239000013008 thixotropic agent Substances 0.000 claims description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 2
- IQGIEMYBDGDBMR-UHFFFAOYSA-N (3-methyl-5-prop-2-enoyloxypentyl) prop-2-enoate Chemical compound C=CC(=O)OCCC(C)CCOC(=O)C=C IQGIEMYBDGDBMR-UHFFFAOYSA-N 0.000 claims description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 2
- RZCMFVQMQKCVEN-UHFFFAOYSA-N 1-methoxypentane-2,4-dione Chemical compound COCC(=O)CC(C)=O RZCMFVQMQKCVEN-UHFFFAOYSA-N 0.000 claims description 2
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 claims description 2
- RGYDDAILUUUYRN-UHFFFAOYSA-N 1-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(CCC)OC(=O)C=C RGYDDAILUUUYRN-UHFFFAOYSA-N 0.000 claims description 2
- YWOYCXNNAGNDKT-UHFFFAOYSA-N 1-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OC(C)OC(=O)C=C YWOYCXNNAGNDKT-UHFFFAOYSA-N 0.000 claims description 2
- JCUZDQXWVYNXHD-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diamine Chemical compound NCCC(C)CC(C)(C)CN JCUZDQXWVYNXHD-UHFFFAOYSA-N 0.000 claims description 2
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 claims description 2
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 claims description 2
- JWTVQZQPKHXGFM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diamine Chemical compound CC(C)(N)CCC(C)(C)N JWTVQZQPKHXGFM-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 2
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 claims description 2
- ZNYBQVBNSXLZNI-UHFFFAOYSA-N 2-ethylhexyl 2-cyanoacetate Chemical compound CCCCC(CC)COC(=O)CC#N ZNYBQVBNSXLZNI-UHFFFAOYSA-N 0.000 claims description 2
- QAUIAXORENGBSN-UHFFFAOYSA-N 2-ethylhexyl 3-oxobutanoate Chemical compound CCCCC(CC)COC(=O)CC(C)=O QAUIAXORENGBSN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- SGLKIEOMYXTGBH-UHFFFAOYSA-N 2-methoxyethyl 2-cyanoacetate Chemical compound COCCOC(=O)CC#N SGLKIEOMYXTGBH-UHFFFAOYSA-N 0.000 claims description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
- JCEZOHLWDIONSP-UHFFFAOYSA-N 3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOCCCN JCEZOHLWDIONSP-UHFFFAOYSA-N 0.000 claims description 2
- GFLJTEHFZZNCTR-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC(=O)C=C GFLJTEHFZZNCTR-UHFFFAOYSA-N 0.000 claims description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- IHSFHIUGYHMYNR-UHFFFAOYSA-N 4-(3-oxobutanoyloxy)butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCOC(=O)CC(C)=O IHSFHIUGYHMYNR-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 2
- BDBZTOMUANOKRT-UHFFFAOYSA-N 4-[2-(4-aminocyclohexyl)propan-2-yl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1C(C)(C)C1CCC(N)CC1 BDBZTOMUANOKRT-UHFFFAOYSA-N 0.000 claims description 2
- MSUHVBQCWASIKB-UHFFFAOYSA-N 4-[diethoxy(ethyl)silyl]butan-1-amine Chemical compound CCO[Si](CC)(OCC)CCCCN MSUHVBQCWASIKB-UHFFFAOYSA-N 0.000 claims description 2
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 claims description 2
- PVVNFQFWDCPPNQ-UHFFFAOYSA-N 6-(3-oxobutanoyloxy)hexyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCCCOC(=O)CC(C)=O PVVNFQFWDCPPNQ-UHFFFAOYSA-N 0.000 claims description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 2
- 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 class 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 claims description 2
- PGDIJTMOHORACQ-UHFFFAOYSA-N 9-prop-2-enoyloxynonyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCOC(=O)C=C PGDIJTMOHORACQ-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- WOFAGNLBCJWEOE-UHFFFAOYSA-N Benzyl acetoacetate Chemical compound CC(=O)CC(=O)OCC1=CC=CC=C1 WOFAGNLBCJWEOE-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- 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 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims description 2
- NCXJHEBVPMOSEM-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CC(C)(CO)CO Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CC(C)(CO)CO NCXJHEBVPMOSEM-UHFFFAOYSA-N 0.000 claims description 2
- 239000005062 Polybutadiene Substances 0.000 claims description 2
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- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- PTMPDDZWMNMUMJ-UHFFFAOYSA-N (2-ethyl-1,3-dioxan-5-yl)methyl prop-2-enoate Chemical compound CCC1OCC(CO1)COC(=O)C=C PTMPDDZWMNMUMJ-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- PLHCSZRZWOWUBW-UHFFFAOYSA-N 2-methoxyethyl 3-oxobutanoate Chemical compound COCCOC(=O)CC(C)=O PLHCSZRZWOWUBW-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LVACOMKKELLCHJ-UHFFFAOYSA-N 3-trimethoxysilylpropylurea Chemical compound CO[Si](OC)(OC)CCCNC(N)=O LVACOMKKELLCHJ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 241000551547 Dione <red algae> Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 101100537098 Mus musculus Alyref gene Proteins 0.000 description 1
- 101100269674 Mus musculus Alyref2 gene Proteins 0.000 description 1
- YVTVFZKHLXIJEY-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.C1OC1COCC1CO1 Chemical compound OC(=O)C=C.OC(=O)C=C.C1OC1COCC1CO1 YVTVFZKHLXIJEY-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000011398 Portland cement Substances 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- 229920004482 WACKER® Polymers 0.000 description 1
- QEZUPGGLXBERBY-UHFFFAOYSA-N [2-ethyl-2-(3-oxobutanoyloxymethyl)hexyl] 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC(CC)(CCCC)COC(=O)CC(C)=O QEZUPGGLXBERBY-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000013006 addition curing Methods 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 229920013820 alkyl cellulose Polymers 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 101150095908 apex1 gene Proteins 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZVLDTJJIODWPHK-UHFFFAOYSA-N butyl 3,5-dioxo-5-phenylpentanoate Chemical compound C(C1=CC=CC=C1)(=O)CC(CC(=O)OCCCC)=O ZVLDTJJIODWPHK-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000010431 corundum Substances 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000001033 granulometry Methods 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- HTEAGOMAXMOFFS-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical group OC(=O)C=C.COC(=O)C(C)=C HTEAGOMAXMOFFS-UHFFFAOYSA-N 0.000 description 1
- PROOHRFTWYWZAA-UHFFFAOYSA-N methyl 5,7-dioxooctanoate Chemical compound COC(=O)CCCC(=O)CC(C)=O PROOHRFTWYWZAA-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Chemical class 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- FEUIEHHLVZUGPB-UHFFFAOYSA-N oxolan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC1CCCO1 FEUIEHHLVZUGPB-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- UVVFKNZCYIIHGM-UHFFFAOYSA-L tetrabutylazanium;carbonate Chemical compound [O-]C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC UVVFKNZCYIIHGM-UHFFFAOYSA-L 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/02—Polyamines
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- 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
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J165/00—Adhesives based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Adhesives based on derivatives of such polymers
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B13/00—Dowels or other devices fastened in walls or the like by inserting them in holes made therein for that purpose
- F16B13/14—Non-metallic plugs or sleeves; Use of liquid, loose solid or kneadable material therefor
- F16B13/141—Fixing plugs in holes by the use of settable material
- F16B13/142—Fixing plugs in holes by the use of settable material characterised by the composition of the setting material or mixture
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
Definitions
- the invention relates to a hybrid system (hereinafter also referred to as hybrid resin system or hybrid adhesive) for chemical fastening technology, in particular for fastening anchoring means in boreholes, which comprises a reaction resin based on ⁇ , ⁇ -unsaturated compounds, a reaction resin based on compounds containing CH-acidic methylene groups , and includes a polyamine, as well as its use and further aspects (embodiments) of the invention mentioned below.
- a hybrid system hereinafter also referred to as hybrid resin system or hybrid adhesive
- hybrid resin system or hybrid adhesive for chemical fastening technology, in particular for fastening anchoring means in boreholes, which comprises a reaction resin based on ⁇ , ⁇ -unsaturated compounds, a reaction resin based on compounds containing CH-acidic methylene groups , and includes a polyamine, as well as its use and further aspects (embodiments) of the invention mentioned below.
- Radically curing systems are characterized by rapid low-temperature curing (e.g. - 10 ° C), but show a relatively high shrinkage ("shrinkage") and not very high pull-out values.
- Systems based on epoxy amine show a significantly slower curing rate at low temperatures (e.g. ⁇ + 5 ° C), but have significantly less shrinkage and significantly higher pull-out values.
- a further object for preferred aspects of the present invention is the provision of a fastening compound in the form of a hybrid system which avoids ingredients that are highly hazardous to health and preferably does not require labeling.
- DE 40 34279 A1 describes an enamine reaction for the production of crosslinked products for use as a coating.
- the enamine reaction occurs spontaneously between polyacetoacetates (reaction resin with CH-acidic methylene groups) and polyamines.
- DE 4034279 A1 suggests the use of primary aminosilanes.
- the crosslinking reaction is no longer part of the enamine reaction, but rather depends on the hydrolysis and condensation reaction of the silane.
- a composition based on vinyl polymers and amines curable by aza-Michael addition (N-Michael addition) is described in EP 1 970480 A1.
- epoxy resins which can also react with the amines, are additionally present in the curable composition.
- the invention relates to a hybrid system which comprises the following components: a) reaction resin based on ⁇ , ⁇ -unsaturated compounds, b) reaction resin which contains compounds bearing CH-acidic methylene groups, and c) primary amine.
- the hybrid system advantageously contains a catalyst.
- the hybrid system is preferably multi-component, in particular two-component, implemented, preferably as a multi-component, such as two-component kit.
- the invention also relates to the use of a multi-component, in particular two-component hybrid system composed as just described, as an adhesive, in particular for fastening anchoring means in substrates such as masonry or concrete, or furthermore for fastening fibers, scrims, fabrics or composites for Reinforcement of structures.
- a hybrid system based on components a), b) and c) combines the advantages found on the one hand in radical curing and, on the other hand, in chemical fastening systems curing by polyaddition, although no radical curing is involved. This is surprising insofar as the reactions taking place in parallel here have never been combined in a hybrid system for chemical fastening technology.
- the following reactions can occur between components a), b) and c): i. Michael addition (a, ß-unsaturated compound + CH-acidic compound) ii. Aza-Michael addition (a, ß-unsaturated compound + amine) iii. Enamine reaction (CH-acidic compound + amine).
- reaction types i. to iii. are, each on their own, from the field of Beschich lines, specifically as a floor coating, known (see the above-mentioned ent speaking patents). Since the forces occurring in the borehole are completely different from those of a (floor) coating, it was not obvious to the person skilled in the field of fastening technology for anchoring means that the reaction types i. to iii. to be considered on its own, or in particular as a hybrid system, for chemical fastening systems for use. From a macroscopic point of view, for example, enormous shear stresses occur in the borehole when subjected to axial loading, which the system has to withstand, whereas a (floor) coating should withstand rather high compressive strengths and abrasion resistance.
- a hybrid system based on components a), b) and c) fulfills the criteria applicable to usability under construction site conditions. These include, on the one hand, sufficient stability at high temperatures ( ⁇ 45 ° C) to prevent running on and / or running out of the borehole, and on the other hand, a sufficiently low viscosity at low temperatures (> - 25 ° C) ) in order to ensure that they can be pressed out by hand from cartridges or the like.
- Consist (d) of means that, in addition to the components or features mentioned, others may also be present, so it stands for a non-exhaustive list, in contrast to “consist (d) of”, which is a final list of the means components or features listed when it is used. In embodiments of the invention, “include” or “comprise” may be replaced by “consist (d) of”.
- the ⁇ , ⁇ -unsaturated compound In a reaction resin based on ⁇ , ⁇ -unsaturated compounds, the ⁇ , ⁇ -unsaturated compound generally contains an ethylenically unsaturated compound in which the carbon double bond is activated by an electron-withdrawing group (for example a carbonyl group in a-position).
- an electron-withdrawing group for example a carbonyl group in a-position
- T riethylenglykoldiacrylat, riisopropylenglykoldiacryalat T, dipropylene glycol diacrylate, neopentyl glycol diacrylate, ethoxylated or propoxylated neopentylglycol diacrylate, tripropylene glycol diacrylate, bisphenol A, bisphenol F, bisphenol AF or bisphenol-S diglycidyl ether diacrylate, bisphenol-A-polyethoxydiacrylat, bisphenol F polyethoxydiacrylat, Polyethylene glycol, polypropylene glycol diacrylate, trimethylolpropane triacrylate, di- trimethylolpropane tetraacrylate, Trimethylolpropanpolyethoxytriacrylat, ethoxylated or propoxylated trimethylolpropane triacrylate, glycerol triacrylate, ethoxylated or propoxylated glycerol triacrylate,
- WO2006 / 087079 A1 such as acrylatomethyl-trimethoxysilane, -methyldimethoxysilane, -dimethylmethoxysilane, -triethoxysilane or -methyldiethoxysilane, acryl-amidomethyl-trimethoxysilane, -methoxysilane, -trimethoxysilane, -methoxysilane, -trimethoxysilane, -methoxysilane, -trimethoxysilane, -methoxy - methyldiethoxysilane, or -methyl-dimethylethoxysilane.
- a reaction resin based on ⁇ , ⁇ -unsaturated compounds can also be understood as a polyester resin based on maleic and / or fumaric and / or itaconic acid, as well as their anhydride.
- Polyester, polyurethane, polyether and / or alkyd resins which carry activated, ethylenically unsaturated groups are also to be understood as such reaction resins.
- Acrylates (particularly preferred), fumarates, itaconates and maleates, particularly characterized as preferred in the present disclosure, are preferred reactive resins.
- the compounds mentioned can also be present as mixtures of two or more thereof.
- Mono-acrylates are also possible. However, because of their chain-breaking effect, these are less preferred or are present as admixtures with di- or polyacrylates.
- Commercially available acrylates and / or fumarates and / or maleates and / or itaconates can be used. Examples of representatives of the mono-acrylates are tetrahydrofurfuryl acrylate, 2-phenoxyethyl acrylate, isobornyl acrylate and / or cyclic trimethylolpropane formal acrylate.
- the more preferred mono-acrylates include acrylated amines, available from Sartomer, for example.
- the monoacrylates, monoacrylates, maleates and / or itaconates can also be mixed with di- or polyacrylates, fumarates, maleates and / or itaconates.
- b-unsaturated compounds with a biogenic component belong to the preferred compounds of this class, i.e. in particular those that are caused by (preferably biogenic) acrylic acid, for example via OH- or SH- or amino (NH2-) or imino (-NH-) contained in the (preferably also biogenic) complementary educts (raw materials) (at least part of the acrylic acid and / or the complementary educts being biogenic) -Groups, or two or more of these groups, are functionalized, in particular those that contain hydroxyl groups and are thus functionalized to (correspondingly fully or at least partially biogenic) acrylic acid esters, such as acrylates (preferably with a biogenic acrylate content) of hydroxy-containing vegetable oils, such as castor oil or soybean oil, wholly or at least partially biogenic (eg C1-C10) alkane (mono-, di-, tri-, tetra-, pe nt
- epoxidized Sojabohnenölacrylat 1,10-Decandiol- diacrylate, nylacrylat tetrahydrofuryl acrylate, isobornyl acrylate, Sorbitolacrylat, lauryl (meth) acrylate, behenyl, propoxylated glyceryl triacrylate, pentaerythritol triacrylate, Pentaerythritoltetra- acrylate, di-Pentaerythritolpentaacrylat, tetrahydrofurfuryl methacrylate, polyethylene glycol di methacrylate, polyester , acrylated fusel oil, or biogenic glycerol triacrylate or such in which at least the acrylate component is biogenic.
- Biogenic urethane acrylates (obtainable, for example, by reaction of isocyanates (such as: Desmodur Eco N 7300) with an acrylate containing OH groups, such as hydroxyethyl, hydroxypropyl, hydroxybutyl or pentaerythritol tri-acrylate, and polyester acrylate resins, e.g. tetrafunctional, are also particularly preferred Polyester acrylates).
- the proportion of bio-based carbon is carried out on the basis of ASTM 6866 (Standard Test Method for Determining the Biobased Content of Solid, Liquid and Gaseous Samples Using Radiocarbon Analysis, using the 14 C content (ASTM International, D6866: 2008 Method A).
- the proportion of the reaction resin based on ⁇ , ⁇ -unsaturated compounds is preferably 1 to 80% by weight, in particular 2 to 60% by weight.
- a reaction resin which contains compounds bearing (one or more) CH-acidic methylene groups (activated methylene groups) includes, in particular, a malonic acid or malonic acid ester, such as malonic acid dimethyl ester, malonic acid diethyl ester, malonic acid di-n-propyl ester, malonic acid diisopropyl ester, malonic acid dibutyl ester -di (2-ethylhexyl) ester or malonic acid dilauryl ester; Cyanoacetic acid esters, such as 2-ethylhexyl cyanoacetate, butyl cyanoacetate, octyl cyanoacetate, 2-methoxyethyl cyanoacetate; Diones, such as pentane-2,4-dione, hexane-2,4-dione, heptane-2,4-dione, 1-methoxy-2,4-pentanedione, 1-phenyl-1
- the reaction resin bearing CH-acidic methylene groups is very particularly preferably an acetoacetate with at least 2 or more acetoacetate groups.
- the acetoacetates can be aliphatic, heteroaliphatic, cyclic, heterocyclic, cycloaliphatic and / or araliphatic.
- the proportion of the CH-acidic compound (s) is preferably 1 to 80% by weight, in particular 2 to 60% by weight.
- CH-acidic compounds with methylene groups are, since they carry two hydrogens, to be regarded as mono- or difunctional.
- a primary amine is to be understood as meaning any common amine hardener that could be used to crosslink epoxy resins.
- primary diamines or polyamines are preferred (where “poly” also includes “oligo”).
- the amine can be either linear or branched.
- the amine molecular structure can contain aliphatic, heteroaliphatic, alicyclic, heterocyclic, aromatic, aliphatic aromatic and silane / siloxane molecular structures or two or more independently selected thereof.
- the primary amine from the group of the aminoamides, polyaminoamides, Mannich bases and the amine adducts (such as in particular epoxy-amine adducts as described, for example, in EP 0 387418 A2, isocyanate-amine adducts, Bucherer adducts and Michael Addition adducts) must be selected.
- Particularly suitable amines are, for example, from the group of the alkylamines (such as: 1,2-diaminoethane, 2-methylpentanediamine, 2,2-dimethyl-1,3-propanediamine, 2,2, 4- or 2,4,4-trimethylhexamethylene diamine), the heteroalkylamines (such as 1,13-diamino-4,7,10-trioxatridecane, commercially available amine-functionalized polyoxyalkylenes [Jeffamine] from Huntsman Corp, triethylenetetramine and / or higher homologues of the cycloalkylamines (such as, for example: isophoronediamine, 1,3- and / or 1,4-bisaminomethylcyclohexane, TCD-diamine, 1,2- and 1,4-diaminocyclohexane, bis (4-aminocyclohexyl) methane, bis (4-amino-3-methyl
- the alkylamines such
- a possible preferred amine is in particular a di- or polyamine, preferably 2-methylpentanediamine (DYTEKA), 1,2-diaminocyclohexane (DCH), 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (IPDA), 1, 3-benzenedimethanamine (MXDA), 1,4-benzenedimethanamine (PXDA), 1,6-diamino-2,2,4-trimethylhexane (TMD), triethylenetetramine (TETA), tetraethylene pentamine (TEPA), pentaethylene hexamine (PEHA), N- aminoethylpiperazine (AEP), 1,3-bis (aminomethyl) cyclohexane (1,3-BAC), TCD-diamine, Jeffamine from Huntsman, dipropylenetriamine, N, N '-Dicyclohexyl-1,6-hexanediamine, N, N' - dimethyl-1,3-diamin
- An aminoalkylsilane that contains at least one hydrolyzable group, such as alkoxy, e.g. methoxy or ethoxy - bonded to silicon - is also of particular interest as a primary amine. This can hydrolyze and condense (for example through water of reaction or water added) and thus form oligomers that carry several amino groups and meet the REACH definition for polymers.
- a preferred aminoalkylsilane of this type is selected, for example, from the group comprising one or more of the following compounds: aminoalkyltri- or -dialkoxysilanes, such as 3-aminopropyl-trimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-aminopropylethyldiethoxysilane, 3-aminopropylethyldiethoxysilane, 3-aminopropylethyldiethoxysilane , 4-aminobutyltiethoxysilane, 4-aminobutylethyldiethoxysilane, and N- (aminoalkyl) -amino-alkyltri- or -dialkoxysilanes, such as N- (2-aminoethyl) -3-aminopropyltrimethoxysilane and N- (2-aminoeth
- a copolymer of one or more of the aforementioned and furthermore other silanes is also of particular interest.
- examples of this are the Dynasilanes (such as Dynasilan 1146) from Evonik and the amino-functional organopolysiloxanes with the brand name Silres from Wacker (such as Silres HP 2000).
- the proportion of (poly) amines is preferably 0.2 to 60% by weight, in particular 1 to 40% by weight.
- a mixture of two or more (in particular those mentioned above) amines is also possible.
- One (or two or more) selected from the following catalysts can advantageously be included as a catalyst for a hybrid system according to the invention:
- Strongly basic catalysts especially with a pKa of 11 or higher
- alkali metal hydroxides e.g. sodium or potassium hydroxide
- alkali metal alkoxides e.g.
- quaternary ammonium compounds e.g. tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, tetrabutylammonium carbonate
- tertiary amines e.g. diazabicyclooctane (also referred to as DABCO) and guanicidines / amidines (e.g. tetramethylguanidines) 5.4.0] undec-7-en, 1,5-diazabicyclo [4.3.0.] Non-5-en
- silicates e.g. sodium silicate
- metal oxides e.g. calcium oxide
- phosphine catalysts e.g.
- tricyclohexylphosphine (particularly preferred) , Tricyclopentylphosphine, tri-n-hexylphosphine, tris (2,4,4-trimethylpentyl) phosphine, tris (2-ethylhexyl) phosphine, tri-n-octylphosphine (particularly preferred), tri-n-decylphosphine, tri -ndodecylphosphine (particularly preferred), tristearylphosphine and triphenylphosphine.
- a further suitable catalyst (resulting after mixing the components of a hybrid system according to the invention) is a mixture of an epoxide (with epoxy groups as (preferably as low molecular weight) glycidyl esters, glycidyl ethers, such as the diglycidyl ether of bisphenol A, or epoxidation products of alpha-olefins) with one or several tertiary amines (in particular triethylenediamine, Mannich reaction products, or the acrylated amines already mentioned above (available from Sartomer)), as described in EP 0 326723 (hereinafter also referred to as epoxy / tert-amine catalysts).
- epoxy groups as (preferably as low molecular weight) glycidyl esters, glycidyl ethers, such as the diglycidyl ether of bisphenol A, or epoxidation products of alpha-olefins)
- tertiary amines in particular triethylenediamine, Mann
- the epoxide can advantageously be accommodated in the component with the a, b-unsaturated compound or the CH-acidic compound or both, the tertiary amine in the component with the a, b-unsaturated compound.
- Salts of strong bases such as tetramethylguanidine, DABCO (1,8-diazabicyclo (5.4.0) undec-7-en) or quaternary ammonium hydroxides can also be added, for example divided in such a way that the starch Base part in one component (preferably not the one with the CH-acidic compound), the epoxide is contained in another component.
- the ingredients react when mixed and form a strong catalytically active base.
- Possible catalysts are also carbon dioxide-blocked strong bases, such as quaternary alkyl ammonium bi- or alkyl carbonates, which, however, are less preferred because they contain CO2 release, except for applications where this is not bothersome or even desirable, for example heat-insulating coatings.
- It can also contain two or more of the catalysts mentioned.
- the catalysts are preferably added in 0.01 to 15% by weight, in particular 0.1 to 10% by weight.
- a multi-component kit (or set) is to be understood as meaning, in particular, a two-component kit, preferably a two- or further multi-chamber device, in which the components that are reactive with one another are contained in such a way that they cannot lead to undesired reactions during storage, preferably such that the components that are reactive with one another do not come into contact with one another before use.
- Cartridges are possible. Particularly suitable, however, are cartridges or foil bags with two or more chambers, or containers such as buckets or tubs with several chambers or sets (e.g.
- the multi-component kit can also include a device for emptying (for example a pressure pistol), but
- the reactive constituents of a hybrid system according to the invention (this primarily means constituents a), b) and c) and the catalyst) are distributed among the components of the multicomponent system, in particular multicomponent kits, in such a way that constituents that are reactive with one another prior to use (especially during manufacture , Storage and transport) do not come into contact with each other (the components are separated from each other in a reaction-inhibiting manner).
- constituents that are reactive with one another prior to use especially during manufacture , Storage and transport
- Corresponding divisions are readily apparent to those skilled in the art.
- components a) and b) are contained in one component (K1), while component c) is contained together with the catalyst in another component (K2) (immiscible in storage, ie separated) is, it being possible for one or more further additional ingredients to be optionally present in each case.
- the catalyst is an epoxy / tert-amine catalyst, it can also be divided between the two components.
- the components a), b) and the epoxy part of an epoxy / tert-amine catalyst are included in one component (K1), and the component c) is included together with the tert -Amin part of an epoxy / tert-amine catalyst in another component (K2), it being possible for one or more additional ingredients to be optionally present here as well.
- a hybrid system according to the invention preferably contains one or more further additives, in particular selected from fillers, rheological auxiliaries, thixotropic agents, plasticizers, coloring additives and adhesion promoters, as well as solvents and / or reactive thinners.
- Customary rheological aids which cause thixotropy can be used as thixotropic agents, such as pyrogenic silica, bentonites, alkyl and methyl celluloses, castor oil derivatives or the like.
- thixotropic agents such as pyrogenic silica, bentonites, alkyl and methyl celluloses, castor oil derivatives or the like.
- they can be added in a weight proportion of 0.01 to 50% by weight, in particular 0.5 to 20% by weight, for example 0.1 to 5% by weight.
- fillers conventional fillers with a fine (e.g. medium grain d50 at 50 ⁇ m or less, in particular at 40 ⁇ m or less, preferably at 30 ⁇ m or less, preferably at 25 ⁇ m or less, e.g.
- a fine e.g. medium grain d50 at 50 ⁇ m or less, in particular at 40 ⁇ m or less, preferably at 30 ⁇ m or less, preferably at 25 ⁇ m or less, e.g.
- preferably at 20 ⁇ m or less can be used preferably at 10 pm or less, primarily 5 pm or less, first and foremost 1 pm or less) or larger medium grain size, in particular chalk, sand, quartz sand, quartz flour, rock flour, glass, porcelain, corundum, ceramics, Silicates, clays, barite, aluminum hydroxide, calcium carbonate or the like, which can be added as powder, in larger form or in the form of shaped bodies, use, or others, such as core or shell flour from plants, which increases the bio-genic carbon content, such as olive seed meal, coconut shell meal or walnut shell meal, or hydraulic fillers such as gypsum, quicklime or cement (e.g.
- fillers can further or in particular also be silanized.
- the fillers can be present in one or more components of a multi-component hybrid adhesive according to the invention, for example one or both components of a corresponding two-component kit; the proportion of fillers is preferably 0 to 90% by weight, for example 10 to 70% by weight (although the covering material (e.g. broken glass or splintered plastic), for example shards, is destroyed when anchoring elements are introduced from cartridges, which can or is preferably counted as filler).
- the mean grain d50 is defined as the grain size at which 50% by weight of the particles is smaller than the specified particle size d50.
- determining the d50 e.g. by means of classifying grading curves with sieves or for example (especially for smaller particles with a diameter of less than 1 ⁇ m) by laser granulometry.
- the medium grain size may correspond to the manufacturer's specifications.
- silane coupling agents with functional groups such as amino, mercapto, epoxy, vinyl, or halogen, such as g-aminopropylmethyldimethoxysilane, g-aminopropylmethyldiethoxysilane, Y- (2-aminoethyl) aminopropyltrimethoxysilane, g-aminopropyl trimethoxysilane (2 -minoethyl) aminopropylmethyldiethoxysilane, Y- (2-aminoethyl) aminopropyltriisopropoxysilane, g-ureidopropyltrimethoxysilane, N-phenyl- g-aminopropyltrimethoxysilane, N-benzyl- g-aminopropyltrimethoxysilane, g-trimethoxinopropylsilicon, g-trimethoxinopropylsil
- additives can also be added, such as plasticizers, non-reactive diluents, flexibilizers, stabilizers, rheological aids, wetting agents and dispersants, coloring additives such as dyes or, in particular, pigments, for example for different coloring of the components for better control of them Mixing, or the like, or a mixture of two or more of them.
- coloring additives such as dyes or, in particular, pigments, for example for different coloring of the components for better control of them Mixing, or the like, or a mixture of two or more of them.
- Such further additives can preferably be added in a total of 0 to 90% by weight, for example from 0 to 40% by weight.
- Alkyl preferably denotes a linear or mono- or multiply branched saturated (acyclic) hydrocarbon radical with up to 20 carbon atoms, for example C C -C -alkyl, in particular C 1 -C 4 -alkyl, such as in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl , tert-butyl, or the like.
- CrC4-alkyl the number 1-4 always refers to the alkyl group itself (and does not include adjacent parts of the molecule, such as -carbonyl or -carbonylmethyl).
- drill holes are made in a horizontal concrete test body (concrete type C20 / 25) with a hammer drill and a hammer drill.
- the drill holes are cleaned with a hand blower and a hand brush.
- the drill holes are then filled to two thirds with the respective hardenable compound to be tested for fastening purposes.
- a threaded rod is pressed in by hand for each borehole.
- the excess mortar is removed with a spatula.
- the threaded rod is pulled until failure while measuring the failure load.
- the gel time is determined from a 30 g mixture in a plastic beaker at 23 ° C. by means of manual stirring. When the gelation point is reached, the previously liquid mixture becomes highly viscous and gel-like, which is noticeable through the formation of lumps. At this point, the clock started after the test started will be stopped. The gel time can be read off directly.
- Tg onset or glass transition temperature
- Example 1 Composition and pull-out tests from concrete of hybrid systems according to the invention (RMA + AMA preferred)
- the bond stresses listed in Table 2 demonstrate the enormous efficiency of the hybrid system according to the invention. Table 2 also shows the robustness of the hybrid system, since both the primary amine content and the molar ratios between amino groups and acrylate groups can be varied over a wide range without suffering a loss in performance.
- Example 2 Compositions and pull-out tests from concrete with different primary amines (RMA + AMA preferred)
- Table 3 shows that all primary amines can be used in the hybrid systems according to the invention.
- Table 3 also shows that the hybrid systems according to the invention can combine the advantages of the systems previously used in chemical fastening technology: a fast one Curing as with radically curing systems, with the high bond stresses of epoxy systems. This is confirmed by the gel times and bond stresses determined.
- Example B2.1 is mixed again with half the amount of TMG. The resulting gel time is 07:20 [mm: ss]. This experiment shows that the gel time can be controlled with the aid of the amount of catalyst used and set to a desired gel time.
- Example 3 Compositions and pull-out tests from concrete of hybrid systems according to the invention (RMA + En preferred)
- the following table 4 shows the constituents used and the determined composite tensions of hybrid systems according to the invention, in which the amount of primary amines used or the primary amino groups (-NH2) present in the system from them are balanced by CH-acidic methylene groups (-CH2-), whereby the reactions i. and iii. can run preferentially.
- Table 4 further illustrates the enormous performance of the hybrid systems according to the invention already shown in Table 2, as well as their robustness.
- Example 4 Pull-out tests from concrete with mixtures of the components a, b and c
- Example 6 Composition and determination of the onset or glass transition temperatures of hybrid systems according to the invention
- the glass transition temperature When the glass transition temperature is exceeded, a solid polymer changes to a rubbery to viscous state.
- the glass transition temperature is a measure of the strength under the influence of heat. Since, depending on the weather, high temperatures can occur on construction sites, the aim is to develop systems with correspondingly high glass transition temperatures. Table 7 below shows the onset or glass transition temperatures of hybrid systems according to the invention in comparison with a standard epoxy-amine system.
- FIS EM 390 S® (fischerwerke GmbH & Co. KG, Waldachtal, Germany) is a successful, well-established example on the market of a two-component injection mortar system for grouting in anchoring elements based on an epoxy-amine reaction.
- Table 7 shows that the onset temperatures of the hybrid systems according to the invention are comparable to an established injection mortar system and even exceed this in the second run in terms of the glass transition temperature.
- the hybrid systems according to the invention accordingly also have the necessary heat resistance, as required under construction site conditions.
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Abstract
L'invention concerne un système hybride destiné à être utilisé comme adhésif, revêtement ou peinture, caractérisé en ce que le système hybride contient a) une résine de réaction sur la base de composés α, β-insaturés, b) une résine de réaction sur la base de composés contenant un groupe méthylène-acide CH et c) une amine primaire. L'invention concerne également un objet associé selon l'invention.
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DE102019133060 | 2019-12-04 | ||
DE102020128713.5A DE102020128713A1 (de) | 2019-12-04 | 2020-11-02 | Michael-Additions-härtendes Hybridsystem für die chemische Befestigungstechnik |
PCT/EP2020/084010 WO2021110621A1 (fr) | 2019-12-04 | 2020-12-01 | Système hybride de durcissement par réaction de michael destiné à être utilisé dans une technologie de fixation chimique |
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EP4069792A1 true EP4069792A1 (fr) | 2022-10-12 |
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EP20819664.2A Pending EP4069792A1 (fr) | 2019-12-04 | 2020-12-01 | Système hybride de durcissement par réaction de michael destiné à être utilisé dans une technologie de fixation chimique |
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US (1) | US20230002653A1 (fr) |
EP (1) | EP4069792A1 (fr) |
JP (1) | JP2023505776A (fr) |
CN (1) | CN114729224A (fr) |
DE (1) | DE102020128713A1 (fr) |
WO (1) | WO2021110621A1 (fr) |
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WO2023139231A1 (fr) * | 2022-01-21 | 2023-07-27 | Arxada Ag | Composition de résine |
CN115044012B (zh) * | 2022-06-01 | 2023-12-12 | 武汉中科先进材料科技有限公司 | 一种亲水型光固化树脂及其制备方法和应用 |
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JPH0739524B2 (ja) * | 1982-05-21 | 1995-05-01 | 日本合成化学工業株式会社 | ポリビニルアルコール系樹脂組成物及びその用途 |
EP0326723B1 (fr) | 1988-02-01 | 1993-03-24 | Rohm And Haas Company | Procédé de réaction de deux composants, compositions, compositions de revêtement et leur application |
DE3908085A1 (de) | 1989-03-13 | 1990-09-20 | Ruetgerswerke Ag | Haertungsmittel fuer epoxidverbindungen, ihre herstellung und verwendung |
DE4034279A1 (de) | 1990-10-27 | 1992-04-30 | Bayer Ag | Verwendung von alkoxysilylaminen als haerter fuer acetoacetat- oder acetoacetamidgruppen aufweisende kunststoffvorlaeufer |
DE4111828A1 (de) | 1991-04-11 | 1992-10-15 | Basf Ag | Patrone fuer die chemische befestigungstechnik |
CA2164994A1 (fr) * | 1994-12-24 | 1996-06-25 | Heinz Dietholf Becker | Liant, agents de revetement incorporant ce liant; ses utilisations |
US8013068B2 (en) * | 2003-01-02 | 2011-09-06 | Rohm And Haas Company | Michael addition compositions |
DE102005007320A1 (de) | 2005-02-17 | 2006-08-24 | Consortium für elektrochemische Industrie GmbH | Durch Michael Additionsreaktion härtbare Zusammensetzungen |
DE102006055974A1 (de) * | 2006-11-24 | 2008-05-29 | Henkel Kgaa | Reaktionsklebstoff |
DE102007012135B3 (de) | 2007-03-12 | 2008-06-19 | Miele & Cie. Kg | Verfahren zum Betreiben einer Waschmaschine oder eines Waschtrockners oder einer elektrischen Heizeinrichtung in einer Waschmaschine oder einem Waschtrockner sowie Waschmaschine oder Waschtrockner und Heizeinrichtung |
EP2357162B1 (fr) | 2010-02-11 | 2012-09-05 | HILTI Aktiengesellschaft | Mortier en résine adapté aux besoins de la construction, spécialement pour l'ancrage chimique |
DE102015003221A1 (de) * | 2014-04-11 | 2015-10-15 | Fischerwerke Gmbh & Co. Kg | CH-Acide Verbindungen und Metallsalze als Härtesystem, entsprechende Harzzusammensetzungen unter anderem für die Befestigungstechnik |
JP6837991B2 (ja) | 2015-04-17 | 2021-03-03 | オールネックス・ネザーランズ・ビー.ブイ.Allnex Netherlands B.V. | フロアコーティング組成物 |
DE102016124075A1 (de) * | 2016-12-12 | 2018-06-14 | Fischerwerke Gmbh & Co. Kg | Hybridbindemittel sowie dessen Verwendung |
-
2020
- 2020-11-02 DE DE102020128713.5A patent/DE102020128713A1/de active Pending
- 2020-12-01 EP EP20819664.2A patent/EP4069792A1/fr active Pending
- 2020-12-01 JP JP2022533649A patent/JP2023505776A/ja active Pending
- 2020-12-01 WO PCT/EP2020/084010 patent/WO2021110621A1/fr unknown
- 2020-12-01 CN CN202080083762.6A patent/CN114729224A/zh active Pending
- 2020-12-01 US US17/780,985 patent/US20230002653A1/en active Pending
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JP2023505776A (ja) | 2023-02-13 |
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US20230002653A1 (en) | 2023-01-05 |
CN114729224A (zh) | 2022-07-08 |
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