EP4069797A1 - Michael-additions-härtendes kunstharz für die chemische befestigungstechnik - Google Patents
Michael-additions-härtendes kunstharz für die chemische befestigungstechnikInfo
- Publication number
- EP4069797A1 EP4069797A1 EP20820070.9A EP20820070A EP4069797A1 EP 4069797 A1 EP4069797 A1 EP 4069797A1 EP 20820070 A EP20820070 A EP 20820070A EP 4069797 A1 EP4069797 A1 EP 4069797A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- synthetic resin
- acrylate
- resin system
- component
- bisphenol
- 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
- 229920003002 synthetic resin Polymers 0.000 title claims abstract description 70
- 239000000057 synthetic resin Substances 0.000 title claims abstract description 70
- 239000000126 substance Substances 0.000 title claims abstract description 20
- 238000005516 engineering process Methods 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- 229920005989 resin Polymers 0.000 claims abstract description 36
- 239000011347 resin Substances 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 20
- 238000004873 anchoring Methods 0.000 claims abstract description 17
- 239000000853 adhesive Substances 0.000 claims abstract description 8
- 230000001070 adhesive effect Effects 0.000 claims abstract description 8
- -1 hydroxypropyl Chemical group 0.000 claims description 40
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 32
- 230000000035 biogenic effect Effects 0.000 claims description 30
- 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 25
- 238000004132 cross linking Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 15
- 239000004593 Epoxy Substances 0.000 claims description 14
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 14
- 239000004567 concrete Substances 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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 8
- 239000002585 base 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
- 229920000642 polymer Polymers 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 239000004615 ingredient 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
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-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
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 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
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 235000012424 soybean oil Nutrition 0.000 claims description 6
- 239000003549 soybean oil Substances 0.000 claims description 6
- 239000002318 adhesion promoter Substances 0.000 claims description 5
- 239000004359 castor oil Substances 0.000 claims description 5
- 235000019438 castor oil Nutrition 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 5
- 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 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 claims description 5
- 229920000058 polyacrylate Polymers 0.000 claims description 5
- 229920005906 polyester polyol Polymers 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- 238000003860 storage Methods 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 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 4
- 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
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 claims description 4
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 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 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
- 125000004386 diacrylate group Chemical group 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-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
- VERHEKWGDRQWPH-UHFFFAOYSA-N n-(trimethoxysilylmethyl)prop-2-enamide Chemical compound CO[Si](OC)(OC)CNC(=O)C=C VERHEKWGDRQWPH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 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
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 3
- 239000007983 Tris buffer 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
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 3
- 239000004744 fabric Substances 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 235000011187 glycerol Nutrition 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229920003986 novolac Polymers 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 229920000223 polyglycerol Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 235000010356 sorbitol Nutrition 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
- 239000013008 thixotropic agent Substances 0.000 claims description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 3
- 239000008158 vegetable oil Substances 0.000 claims description 3
- 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
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-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
- 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 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
- PLHCSZRZWOWUBW-UHFFFAOYSA-N 2-methoxyethyl 3-oxobutanoate Chemical compound COCCOC(=O)CC(C)=O PLHCSZRZWOWUBW-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
- 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
- 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
- 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-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
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-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
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
- MXHUVJDCDLWMKY-UHFFFAOYSA-N [1-(3-oxobutanoyloxymethyl)cyclohexyl]methyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC1(COC(=O)CC(C)=O)CCCCC1 MXHUVJDCDLWMKY-UHFFFAOYSA-N 0.000 claims description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229920000180 alkyd Polymers 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 claims description 2
- DJACTCNGCHPGOI-UHFFFAOYSA-N butyl 2-cyanoacetate Chemical compound CCCCOC(=O)CC#N DJACTCNGCHPGOI-UHFFFAOYSA-N 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- NFKGQHYUYGYHIS-UHFFFAOYSA-N dibutyl propanedioate Chemical compound CCCCOC(=O)CC(=O)OCCCC NFKGQHYUYGYHIS-UHFFFAOYSA-N 0.000 claims description 2
- LKNAVAQNRCASPT-UHFFFAOYSA-N didodecyl propanedioate Chemical compound CCCCCCCCCCCCOC(=O)CC(=O)OCCCCCCCCCCCC LKNAVAQNRCASPT-UHFFFAOYSA-N 0.000 claims description 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- QRVSDVDFJFKYKA-UHFFFAOYSA-N dipropan-2-yl propanedioate Chemical compound CC(C)OC(=O)CC(=O)OC(C)C QRVSDVDFJFKYKA-UHFFFAOYSA-N 0.000 claims description 2
- LWIWFCDNJNZEKB-UHFFFAOYSA-N dipropyl propanedioate Chemical compound CCCOC(=O)CC(=O)OCCC LWIWFCDNJNZEKB-UHFFFAOYSA-N 0.000 claims description 2
- KCHWKBCUPLJWJA-UHFFFAOYSA-N dodecyl 3-oxobutanoate Chemical compound CCCCCCCCCCCCOC(=O)CC(C)=O KCHWKBCUPLJWJA-UHFFFAOYSA-N 0.000 claims description 2
- 239000001760 fusel oil Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- ILPNRWUGFSPGAA-UHFFFAOYSA-N heptane-2,4-dione Chemical compound CCCC(=O)CC(C)=O ILPNRWUGFSPGAA-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- NDOGLIPWGGRQCO-UHFFFAOYSA-N hexane-2,4-dione Chemical compound CCC(=O)CC(C)=O NDOGLIPWGGRQCO-UHFFFAOYSA-N 0.000 claims description 2
- ZZXXBDPXXIDUBP-UHFFFAOYSA-N hydroxymethyl prop-2-enoate Chemical compound C(C=C)(=O)OCO.C(C=C)(=O)OCO ZZXXBDPXXIDUBP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
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- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 150000002430 hydrocarbons Chemical class 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
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 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
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- SJPCQNABHNCLPB-UHFFFAOYSA-N methyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OC SJPCQNABHNCLPB-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Chemical class 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000006855 networking Effects 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
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920005650 polypropylene glycol diacrylate 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 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
- 239000000376 reactant Substances 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000004432 silane-modified polyurethane 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
- 239000007787 solid Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007655 standard test method Methods 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
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Chemical group 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
- C04B26/02—Macromolecular compounds
- C04B26/10—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- 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
- F16B11/00—Connecting constructional elements or machine parts by sticking or pressing them together, e.g. cold pressure welding
- F16B11/006—Connecting constructional elements or machine parts by sticking or pressing them together, e.g. cold pressure welding by gluing
-
- 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
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
- C04B2111/00474—Uses not provided for elsewhere in C04B2111/00
- C04B2111/00715—Uses not provided for elsewhere in C04B2111/00 for fixing bolts or the like
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/13—Morphological aspects
- C08G2261/135—Cross-linked structures
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/334—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing heteroatoms
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/60—Glass transition temperature
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/62—Mechanical aspects
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/76—Post-treatment crosslinking
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
Definitions
- the invention relates to a synthetic resin system for chemical fastening technology, in particular for fastening anchoring means in boreholes, which contains a reaction resin based on ⁇ , ⁇ -unsaturated compounds, a reaction resin based on compounds containing CH-acidic methylene groups, and a catalyst, 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.
- the object of the present invention is to provide a synthetic resin system which allows rapid low-temperature curing as in the case of free-radically polymerizable Systems with significantly higher pull-out values as in polyaddition-curing systems (epoxy-amine) combined.
- Another object for preferred aspects of the present invention is the provision of a fastening compound in the form of a synthetic resin system, which avoids ingredients that are highly hazardous to health and preferably does not require labeling.
- US 4217396 also describes crosslinked acrylate-acetoacetate polymers for use as floor coatings.
- the acetoacetates used are exclusively diacetoacetates, which in combination with polyfunctional acrylates form the floor coating.
- the crosslinking index used in the examples is 2.9.
- US 4602 061 describes a paint composition curable at room temperature, which consists of an ⁇ , ß-unsaturated carbonyl compound and a compound with activated CH groups (such as oligomers or polymeric esters containing malonate groups).
- the paint composition cures quickly and without the application of heat and has excellent hardness.
- the crosslinking indices used in the compositions range from 2.0 to 2.7.
- the American patent application US 2005/0081995 A1 is based on an adhesive composition which consists of at least one Michael donor, at least one Michael acceptor and at least one anion of a Michael donor.
- the adhesive composition is used to make adhesive strips and has a crosslinking index in the range from 2.0 to 2.2.
- the invention relates to a synthetic resin 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) a catalyst.
- the synthetic resin system is preferably multi-component, in particular two-component, designed, 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 synthetic resin system composed as just described as an adhesive, in particular for fastening anchoring means in substrates such as masonry or concrete, or for fastening fibers, scrims, fabrics or composites for Reinforcement of structures.
- Corresponding methods and methods for grouting anchoring elements in holes or crevices in which a multi-component, in particular two-component, synthetic resin system according to the invention is used for mortaring (gluing) anchoring means, the synthetic resin system and an anchoring means one after the other, in particular first the synthetic resin system, then the anchoring means, or (at least substantially) simultaneously, are introduced into a hole or a gap in a substrate (also in a cracked substrate, such as cracked concrete), or mixed forms, each with partial introduction, form an embodiment of the invention.
- a synthetic resin system based on components a), b) and c) combines the advantages that can be 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 reaction taking place here has never been used in a synthetic resin system for chemical fastening technology.
- the Michael addition is known from the field of coatings, especially for floor coatings (see the above-mentioned corresponding Patents). Since the forces occurring in the borehole are completely different from those of a (floor) coating, it was not obvious to those skilled in the field of fastening technology for anchors to carry the Michael addition between ⁇ , ⁇ -unsaturated compounds and CH-acidic methylene groups To consider compounds as a synthetic resin system for chemical fastening systems for use. In the borehole - viewed macroscopically - enormous shear stresses occur in the event of an axial load, which the system has to withstand, whereas a (floor) coating should withstand rather high compressive strengths and abrasion strengths.
- the inventors have also surprisingly found that a synthetic resin system based on a Michael addition also has a high performance in the borehole when using highly functionalized starting materials.
- the inventors were also able to determine that the higher the crosslinking index, the higher the pull-out values from concrete. This is surprising insofar as the European patent application EP 3299432 A1 teaches on pages 2 and 3 that the polymerisation shrinkage increases with an increasing proportion of functional groups (here (meth) acrylate groups) and the load-bearing behavior of the chemical composite dowel is significantly impaired as a result.
- the invention relates to a synthetic resin system which comprises the following components: a) reaction resin based on a, ß-unsaturated compounds with an average functionality> 2 b) reaction resin which contains CH-acidic methylene group-bearing compounds with an average functionality> 4, and c) a catalyst.
- crosslinking density for the cured product is based on a crosslinking index in the range of 3.0 or higher, the crosslinking index IV generally being determined using the following formula:
- - ni is the amount of substance (number) of the corresponding groups of molecule i of the overall system
- - fi is the respective (possibly mean in the case of mixtures) functionality of the reactive molecules, taking into account the number of possible reactions with a potential reactant; Two-component system) so that, according to the invention, the amount of excess reactive groups of a component should preferably not deviate by more than 20% from the stoichiometrically correct amount, preferably by less than 10%, even more preferably by less than 0.5%, and where full implementation is accepted.
- the crosslinking index is thus also a theoretically determined (mean) variable which can be obtained or determined from the data Ai, ni and fi or corresponding information for the methods for determining reactive groups (for example, commercially available or known to those skilled in the art according to methods known to the person skilled in the art) ) Educts is determined.
- the person skilled in the art can readily understand that a wide variety of crosslinking indices can be achieved by mixing compounds with different functionalities in suitable ratios to one another (see also the above formula).
- the subject of the present invention is thus in a further embodiment of the invention a synthetic resin system which comprises the following components: a) reaction resin based on a, ß-unsaturated compounds with an average functionality> 2 b) reaction resin which contains CH-acidic methylene group-bearing compounds with an average Functionality> 4, and c) a catalyst, characterized in that the crosslinking index of the synthetic resin system is> 3. It was also found that a synthetic resin system based on components a), b) and c) fulfills the criteria applicable for usability under construction site conditions.
- proportions or content data in percent mean weight percent (“% by weight”) or the relative weight proportion, unless otherwise stated, based on all ingredients of a synthetic resin system according to the invention (without packaging material), unless otherwise stated or evident.
- 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 when it is used means listed components or features. In embodiments of the invention, “include” or “comprise” may be replaced by “consist (d) of”.
- the average functionality of the ⁇ , ⁇ -unsaturated compounds is> 2, in particular> 2 to 20 or preferably up to 18, in particular 2.05 to 20 or preferably up to 18, preferably 2.1 to 20,.
- the average functionality of the compound bearing CH-acidic methylene groups is> 4, in particular> 4 to 12, preferably up to 7, in particular 4.05 to 12, preferably up to 7, preferably 4.1 to 12, preferably to 7.
- the crosslinking index of the synthetic resin system is> 3, preferably> 3 to 6, in particular 3.1 to 6, more preferably 3.5 to 6, more preferably 4 to 6, especially 4.1 to 4.3.
- the ⁇ , ⁇ -unsaturated compound in a reaction resin based on ⁇ , ⁇ -unsaturated compounds, can generally be 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).
- Acrylic-functional alkoxysilanes or organopolysiloxanes are also possible (cf. WO2006 / 087079 A1), such as acrylatomethyl-trimethoxysilane, -methyldimethoxysilane, -dimethylmethoxysilane, -triethoxysilane or -methyldiethoxysilane, acrylamidomethyl-trimethoxysilane, -methyl-silane, methoxysilane, acrylamidomethyl-trimethoxysilane, -methyl-di-methoxysilane, acrylamidomethyl-trimethoxysilane , or -methyl- dimethylethoxysilane.
- a reaction resin based on ⁇ , ⁇ -unsaturated compounds can also be understood to mean a polyester resin based on maleic, fumaric or itaconic acid, or in each case 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, especially those identified 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, maleates or itaconates can be used. Examples of representatives of the mono-acrylates are tetrahydrofurfuryl acrylate, 2-phenoxyethyl acrylate, isobornyl acrylate and / or cyclic trimethylolpropane formalacrylate.
- the more preferred mono-acrylates include acrylated amines, available from Sartomer, for example.
- the monoacrylates, fumarates, maleates and / or itaconates can also be mixed with di- or polyacrylates, fumarates, maleates and / or itaconates.
- a, b-unsaturated compounds with a biogenic component (characterized by the 14 C content, which is higher relative to the total carbon content than with fossil materials) belong to the preferred compounds of this class, i.e.
- epoxidized soybean oil acrylate 1,10-decanediol diacrylate, tetrahydrofuryl acrylate, isobornyl acrylate, sorbitol acrylate, lauryl (meth) acrylate, benhenyl acrylate, propoxylated glycerol triacrylate, pentaerythritol, triacrylate, pentaerythritol, triacrylate, pentaerythritol, acrylate, pentaerythritol, pentaacrylate, pentaacrylate, methacrylate, pentaacrylate, pentaacrylate, pentaacrylate, pentaacrylate , pentaacrylate , 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 polyester acrylates).
- isocyanates such as: Desmodur Eco N 7300
- an acrylate containing OH groups such as hydroxyethyl, hydroxypropyl, hydroxybutyl or pentaerythritol tri-acrylate
- polyester acrylate resins e.g. tetrafunctional 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).
- acrylates are mentioned above and below, this also includes, alternatively or in combination, the corresponding methacrylates (in the case of the more specific, to be realized by adding (“meth” before “acrylate”).
- methacrylates in the case of the more specific, to be realized by adding (“meth” before “acrylate”).
- a mixture of two or more (in particular the abovementioned) ⁇ , ⁇ -unsaturated compounds is also possible.
- 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 (one or more) CH-acidic methylene groups (activated methylene groups) is in particular one of malonic acid or malonic acid esters, such as malonic acid dimethyl ester, malonic acid di-ethyl 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-1,3-but
- 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.
- the methylene groups are to be regarded as difunctional for the Michael addition and the calculation of the crosslinking index.
- One (or two or more) selected from the following catalysts can advantageously be included as a catalyst for a synthetic resin 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) , Tricylopentylphosphine, tri-n-hexylphosphine, tris (2,4,4-trimethylpentyl) phosphine, tris (2-ethylhexyl) phosphine, tri-n-octylphosphine (particularly preferred), tri-n-decylphosphine, tri-n-dodecylphosphine (particularly preferred), tristearylphosphine and triphenylphosphine.
- a further suitable catalyst (resulting after mixing the components of a synthetic resin 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,
- the epoxide can advantageously be accommodated in the component with the ⁇ , ⁇ -unsaturated compound or the CH-acidic compound or both, the tertiary amine in the component with the ⁇ , ⁇ -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 used be added, for example divided in such a way that the starch-base part is contained 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 are, however, less preferred because they release CO2, 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 is to be understood as meaning, in particular, a two-component kit (preferably a two-component kit, preferably a two- or furthermore multi-chamber device, in which the components that are reactive to one another are contained in such a way that they cannot lead to undesired reactions during storage, preferably so that the reactive components do not come into contact with each other before use.
- Cartridges are possible. However, cartridges or foil bags with two or more chambers, or containers such as buckets or tubs with several chambers or sets (e.g.
- containers are particularly suitable of two or more such containers, with two or more components of the respective curable synthetic resin system, in particular two components, each spatially separated from one another as a kit or set, in which the contents, after mixing or mixing, are applied to the application site (in particular by means of devices for A.
- the multi-component kit can also include a device for emptying (for example a pressure pistol), but this can preferably also be made up or offered (for example for multiple use) independently of the kit.
- the reactive constituents of a synthetic resin system according to the invention (this primarily means constituents a), b) and c) are distributed among the components of the multicomponent system, in particular multicomponent kits, that mutually reactive constituents prior to use (especially during manufacture, storage and Transport) do not come into contact with one another (the components are separated from one another in a reaction-inhibiting manner).
- mutually reactive constituents prior to use especially during manufacture, storage and Transport
- the components are separated from one another in a reaction-inhibiting manner.
- components a) and b) are contained in one component (K1), while component c) alone or together with a non-reactive solvent / diluent / plasticizer and / or adhesion promoter in another ( Component (K2) which is immiscible in the storage state, ie separated) is included, 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, this is also divided between the two components.
- components a), b) and the epoxy part of an epoxy / tert-amine catalyst are contained in one component (K1), and component c) together with the tert - Amine 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 synthetic resin system according to the invention preferably contains one or more other additives, in particular selected from fillers, rheological aids, 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. They can be added, for example, in a proportion by weight of 0.01 to 50% by weight, in particular 0.5 to 20% by weight, for example 0.1 to 5% by weight.
- 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.
- 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 powder, rock flour, glass, porcelain, corundum, ceramics, silicates, Clays, barite, aluminum hydroxide, calcium carbonate or the like, which can be added as powder, in granular form or in the form of shaped bodies, use, or others, such as kernel or shell meal from plants, which increases the biogenic carbon content, such as olive kernel flour, coconut shell flour or also walnut shell flour, or hydraulic fillers such as gypsum, quicklime or cement (for example clay or Portland cement), water glasses or active aluminum hydroxides, ode r Mixtures of two or more thereof, wherein the fillers can furthermore or in particular also be silanized.
- medium grain size in particular chalk, sand, quartz sand, quartz powder, rock flour, glass, porcelain, corundum, ceramics, silicates
- the fillers can be present in one or more components of a multi-component synthetic resin system 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 (with the encasing material destroyed when anchoring elements are introduced (e.g. shattered glass or shattered plastic), for example shards from cartridges, as filler can be credited or preferably will).
- the proportion of fillers is preferably 0 to 90% by weight, for example 10 to 70% by weight (with the encasing material destroyed when anchoring elements are introduced (e.g. shattered glass or shattered plastic), for example shards from cartridges, as filler can be credited or preferably will).
- 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 mercapto, epoxy, vinyl, or halogen, such as g-ureidopropyltrimethoxysilane, N-vinylbenzyl-y-aminopropyltriethoxysilane, g-mercaptopropyltrimethoxysilane, g-mercaptopropyl-triethoxysilane, g-mercapto-propyl-triethoxy-methoxysilane, g-mercapto-propyl-triethoxy-methoxysilane, Mercaptopropylmethyldimethoxysilane, g-glycidyloxypropyltrimethoxysilane, g-glycidylpropyltriethoxysilane, g-glycidyloxypropylmethyldimethoxysilane, ß- (3,4-epoxycyclohexyl) et
- functional groups such as mercap
- 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 especially pigments, for example for different coloring of the components for better control of their mixing, or the like, or a mixture of two or more thereof.
- coloring additives such as dyes or especially pigments, for example for different coloring of the components for better control of their mixing, or the like, or a mixture of two or more thereof.
- Such further additives can preferably be added in total in proportions by weight of a total of 0 to 90%, for example from 0 to 40% by weight.
- Alcohols such as 2-propanol, 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane, 1,2-propanediol, 1,4-butanediol, ethylene glycol, hexylene glycol, ethoxylated bisphenol A, such as the company's Dianoie Seppic; Polyols such as polyether polyols and / or polyester polyols such as Voranoie from Dow Chemical Company; Esters, such as tris (2-ethylhexyl) -0-acetyl citrate, triethyl citrate, acetyl tri butyl citrate, glycerol triacetate, isodecyl benzoate, 2,2,4-trimethyl-1,3-pentanediol di-isobutyrate, DBE - dibasic esters, 1,2 -Cyclohexanedicarboxylic
- a biogenic, non-reactive diluent (diluent) which is liquid as such at the application temperature is to be understood as meaning in particular one which occurs as such (in unmixed form) at room temperature or in the range from 0 to 30 ° C. in liquid form.
- diluent is a vegetable oil, such as castor oil, linseed oil, epoxidized linseed oil or also corresponding hydroxylated and hydroxyalkylated oils (e.g.
- polyether polyester polyols or polyester polyols such as corresponding Merginols® from Hobum Oleochemicals GmbH, Hamburg, Germany), soybean oil, epoxidized soybean oil or rapeseed oil, or also fatty acid alkyl esters ("biodiesel”), such as fatty acid methyl esters, eg rapeseed methyl ester or soybean oil methyl ester. Castor oil is particularly preferred.
- biogenic polyol in particular biogenic glycerine and / or biogenic 1,4-butanediol, in particular of vegetable origin, can be used.
- Non-reactive means that under normal application conditions there is no or only a negligible chemical reaction of the liquid diluent with the reactive system, ie the components that polymerize and initiate the polymerization.
- 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 horizontally lying concrete test specimen (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. After 24 hours at room temperature, 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 Compositions and pull-out tests from concrete of synthetic resin systems according to the invention
- Example 2 Compositions and pull-out tests from concrete with different TMPTA ratios
- Table 3 shows that despite the deviation from the optimal mixing ratio (B2.4 - determined with DSC based on ISO 11357-2 (2013)) the bond stress remains relatively constant.
- Example 3 Compositions and pull-out tests with different catalysts and screening catalyst content
- Table 4 below shows the constituents used and the determined bond stresses of synthetic resin systems according to the invention, in which the type and amount of catalysts used are varied.
- Table 4 shows that all strongly basic compounds can be used as catalysts for the synthetic resin systems according to the invention.
- Table 4 also shows that the gel time varies with the aid of the amount of catalyst used or can be adjusted to a desired gel time.
- Table 4 also shows that the synthetic resin systems according to the invention can combine the advantages of the systems previously used in chemical fastening technology: rapid curing as in the case of radically curing systems, with the high bond stresses of epoxy systems. This is confirmed by the gel times and bond stresses determined.
- Example 4 Compositions and pull-out tests at low temperatures and reference tests
- Example 5 Compositions and pull-out tests after different curing times
- Table 7 shows mixtures of different acrylates and their bond stresses determined in the pull-out test, as well as their onset and glass transition temperatures.
- Table 7 shows that all acrylates can be used in the synthetic resin systems according to the invention.
- the listed onset or glass transition temperature which is a measure of the heat resistance of the respective system, shows that the synthetic resin systems according to the invention are suitable for use under construction site conditions (depending on the weather, high temperatures can occur here) and even the injection mortar FIS EM 390 Outperform S ® in the 2nd run.
- Example 7 Compositions and pull-out tests with different crosslinking indices
- the synthetic resin systems according to the invention should have a certain crosslinking index. This differs greatly from the networking indices used for (floor) coatings from the prior art.
- the following table 8 is intended to show this.
- Table 8 shows that the bond tension increases as the crosslinking index of the synthetic resins according to the invention increases.
- Table 8 also shows that the glass transition temperature (an important parameter for a fastening system because it represents an indirect measure of the heat resistance) also increases with the increasing crosslinking index. For this reason, the synthetic resins according to the invention should have a crosslinking index of> 3.
- Example 8 Cartridge formulation for pull-out tests
- a 150 ml cartridge with a volume ratio of 7: 1 is filled from the components listed in Table 9 and subjected to a setting test according to the aforementioned methods for determining parameters for “pull-out tests from concrete”. In this case, component A is filled into the larger part of the volume.
- the bond stress determined is 28 N / mm 2 .
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- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Mechanical Engineering (AREA)
- Ceramic Engineering (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
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DE102019133063 | 2019-12-04 | ||
DE102020128717.8A DE102020128717A1 (de) | 2019-12-04 | 2020-11-02 | Michael-Additions-härtendes Kunstharz für die chemische Befestigungstechnik |
PCT/EP2020/084011 WO2021110622A1 (de) | 2019-12-04 | 2020-12-01 | Michael-additions-härtendes kunstharz für die chemische befestigungstechnik |
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US (1) | US20220411680A1 (zh) |
EP (1) | EP4069797A1 (zh) |
JP (1) | JP2023505777A (zh) |
CN (1) | CN114729253A (zh) |
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Publication number | Priority date | Publication date | Assignee | Title |
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US4217396A (en) | 1979-05-10 | 1980-08-12 | Armstrong Cork Company | Acrylate-acetoacetate polymers useful as protective agents for floor coverings |
ZA852044B (en) | 1984-03-29 | 1985-11-27 | Akzo Nv | Liquid coating composition curable at ambient temperature |
EP0326723B1 (en) | 1988-02-01 | 1993-03-24 | Rohm And Haas Company | Method for reacting two components, compositions, coating compositions and uses thereof |
DE4111828A1 (de) | 1991-04-11 | 1992-10-15 | Basf Ag | Patrone fuer die chemische befestigungstechnik |
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 |
EP2357162B1 (en) | 2010-02-11 | 2012-09-05 | HILTI Aktiengesellschaft | Resin mortar suitable for construction purposes, especially for chemical anchoring |
EP2829524A1 (de) * | 2013-07-24 | 2015-01-28 | HILTI Aktiengesellschaft | Harzmischung, Reaktionsharz-Mörtel, Mehrkomponenten-Mörtelsystem und deren Verwendung |
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 |
EP3299432A1 (de) | 2016-09-26 | 2018-03-28 | HILTI Aktiengesellschaft | Zweikomponenten-mörtelmasse und deren verwendung |
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- 2020-12-01 CN CN202080083757.5A patent/CN114729253A/zh active Pending
- 2020-12-01 JP JP2022533651A patent/JP2023505777A/ja active Pending
- 2020-12-01 EP EP20820070.9A patent/EP4069797A1/de active Pending
- 2020-12-01 US US17/780,987 patent/US20220411680A1/en active Pending
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WO2021110622A1 (de) | 2021-06-10 |
DE102020128717A1 (de) | 2021-06-10 |
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