JP2015525246A - 撥水性オルガノポリシロキサン材料 - Google Patents
撥水性オルガノポリシロキサン材料 Download PDFInfo
- Publication number
- JP2015525246A JP2015525246A JP2015509433A JP2015509433A JP2015525246A JP 2015525246 A JP2015525246 A JP 2015525246A JP 2015509433 A JP2015509433 A JP 2015509433A JP 2015509433 A JP2015509433 A JP 2015509433A JP 2015525246 A JP2015525246 A JP 2015525246A
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- JP
- Japan
- Prior art keywords
- water
- microcapsules
- product
- composition
- water repellent
- 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.)
- Granted
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 77
- 239000005871 repellent Substances 0.000 title claims abstract description 52
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 44
- 230000002940 repellent Effects 0.000 title claims abstract description 39
- 239000000463 material Substances 0.000 title claims description 21
- 239000003094 microcapsule Substances 0.000 claims abstract description 81
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000011162 core material Substances 0.000 claims abstract description 12
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 10
- 239000010703 silicon Substances 0.000 claims abstract description 10
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 239000000839 emulsion Substances 0.000 claims description 47
- 239000000758 substrate Substances 0.000 claims description 27
- 150000003377 silicon compounds Chemical class 0.000 claims description 25
- 239000004568 cement Substances 0.000 claims description 21
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 19
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 19
- 239000002023 wood Substances 0.000 claims description 17
- -1 polydimethylsiloxane Polymers 0.000 claims description 16
- 239000004927 clay Substances 0.000 claims description 12
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 10
- 239000011449 brick Substances 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 239000010440 gypsum Substances 0.000 claims description 6
- 229910052602 gypsum Inorganic materials 0.000 claims description 6
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 5
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 5
- 239000004571 lime Substances 0.000 claims description 5
- 230000001413 cellular effect Effects 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 239000000725 suspension Substances 0.000 description 24
- 239000002245 particle Substances 0.000 description 13
- 239000000654 additive Substances 0.000 description 11
- 125000002091 cationic group Chemical group 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- 239000003093 cationic surfactant Substances 0.000 description 9
- 230000002209 hydrophobic effect Effects 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000004567 concrete Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000002280 amphoteric surfactant Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- WSFMFXQNYPNYGG-UHFFFAOYSA-M dimethyl-octadecyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical group [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC WSFMFXQNYPNYGG-UHFFFAOYSA-M 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000005470 impregnation Methods 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000004566 building material Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011094 fiberboard Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-M 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC([O-])=O YPIFGDQKSSMYHQ-UHFFFAOYSA-M 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000018783 Dacrycarpus dacrydioides Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 240000007320 Pinus strobus Species 0.000 description 1
- 235000008578 Pinus strobus Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910004283 SiO 4 Inorganic materials 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- MXMZCLLIUQEKSN-UHFFFAOYSA-N benzimidazoline Chemical compound C1=CC=C2NCNC2=C1 MXMZCLLIUQEKSN-UHFFFAOYSA-N 0.000 description 1
- UHWHEIKTDHONME-UHFFFAOYSA-M benzyl-decyl-dimethylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 UHWHEIKTDHONME-UHFFFAOYSA-M 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 1
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- KZOIWQKIVZDOGH-UHFFFAOYSA-M didodecyl(dimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC KZOIWQKIVZDOGH-UHFFFAOYSA-M 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VBVQYGNPGUXBIS-UHFFFAOYSA-M dimethyl(dioctadecyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC VBVQYGNPGUXBIS-UHFFFAOYSA-M 0.000 description 1
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 1
- JVQOASIPRRGMOS-UHFFFAOYSA-M dodecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[N+](C)(C)C JVQOASIPRRGMOS-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- WJLUBOLDZCQZEV-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)C WJLUBOLDZCQZEV-UHFFFAOYSA-M 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 238000000614 phase inversion technique Methods 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 239000010875 treated wood Substances 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- STYCVOUVPXOARC-UHFFFAOYSA-M trimethyl(octyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCC[N+](C)(C)C STYCVOUVPXOARC-UHFFFAOYSA-M 0.000 description 1
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010876 untreated wood Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
- B01J13/18—In situ polymerisation with all reactants being present in the same phase
-
- 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
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/40—Compounds containing silicon, titanium or zirconium or other organo-metallic compounds; Organo-clays; Organo-inorganic complexes
- C04B24/42—Organo-silicon compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/02—Processes; Apparatus
- B27K3/15—Impregnating involving polymerisation including use of polymer-containing impregnating agents
- B27K3/153—Without in-situ polymerisation, condensation, or cross-linking reactions
-
- 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
- C04B20/00—Use of materials as fillers for mortars, concrete or artificial stone according to more than one of groups C04B14/00 - C04B18/00 and characterised by shape or grain distribution; Treatment of materials according to more than one of the groups C04B14/00 - C04B18/00 specially adapted to enhance their filling properties in mortars, concrete or artificial stone; Expanding or defibrillating materials
- C04B20/10—Coating or impregnating
- C04B20/1051—Organo-metallic compounds; Organo-silicon compounds, e.g. bentone
-
- 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
- C04B28/00—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements
- C04B28/02—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements containing hydraulic cements other than calcium sulfates
-
- 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
- C04B38/00—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof
- C04B38/10—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof by using foaming agents or by using mechanical means, e.g. adding preformed foam
-
- 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
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
-
- 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
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/49—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes
- C04B41/4905—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon
- C04B41/495—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as oligomers or polymers
- C04B41/4961—Polyorganosiloxanes, i.e. polymers with a Si-O-Si-O-chain; "silicones"
-
- 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
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/50—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with inorganic materials
- C04B41/502—Water
-
- 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
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/60—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only artificial stone
- C04B41/61—Coating or impregnation
- C04B41/62—Coating or impregnation with organic materials
- C04B41/64—Compounds having one or more carbon-to-metal of carbon-to-silicon linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K2240/00—Purpose of the treatment
- B27K2240/70—Hydrophobation treatment
-
- 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
- C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
- C04B2103/0045—Polymers chosen for their physico-chemical characteristics
- C04B2103/0052—Hydrophobic 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
- C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
- C04B2103/0045—Polymers chosen for their physico-chemical characteristics
- C04B2103/0058—Core-shell 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
- C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
- C04B2103/40—Surface-active agents, dispersants
-
- 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
- C04B2111/20—Resistance against chemical, physical or biological attack
- C04B2111/27—Water resistance, i.e. waterproof or water-repellent materials
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2207/00—Properties characterising the ingredient of the composition
- C08L2207/53—Core-shell polymer
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Forests & Forestry (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Silicon Polymers (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Aftertreatments Of Artificial And Natural Stones (AREA)
Abstract
Description
粘度が25℃で9 000mm2/sの33.3%撥水性PDMSを、高剪断ローターステーターミキサーを使用して、カチオン性界面活性剤である0.3%塩化ヘキサデシルトリメチルアンモニウムを含有する66.4%の水中で乳化した。N−オクタデシル−N,N−ジメチル−トリメトキシシリルプロピルアンモニウムクロリドを、生成したエマルションに添加した。10% TEOSをエマルションに攪拌しながら添加した。中位径3μmのマイクロカプセルが懸濁液中で生成した。マイクロカプセルは、PDMSのコアと、シリカ単位及びN−オクタデキシル−N,N−ジメチル−トリメトキシシリルプロピルアンモニウムクロリド由来のカチオン性シロキサン単位を含むTEOSのネットワークポリマーのシェルとを含んでいた。
・等級1:10分後、表面は湿っていない。水滴の跡が全く残っていない。
・等級2:接触部分の最大50%が湿っている(やや暗色)。
・等級3:接触部分100%が湿っている(暗色)。
・等級4:水滴の周りに小さな拡散リングがあり、滴の最大10%が吸収されている。
・等級5:水滴の周りに顕著な拡散リングがあり、滴の最大50%が吸収されている。
・等級6:滴が完全に吸収されている。
実施例1で生成したマイクロカプセルの懸濁液を水で希釈して3%のPDMS(実施例2)又は1%のPDMS(実施例3)を含有するようにした。希釈懸濁液を、予め形成したコンクリートブロックの表面上に噴霧し、実施例1に記載の通り検査した。塗布量と検査結果を表1に示す。
実施例4:粘度が25℃で50 000mm2/sの25%撥水性シラノール末端PDMSを、高剪断ローターステーターミキサーを使用して、カチオン性界面活性剤である0.11%塩化ヘキサデシルトリメチルアンモニウムを含有する66.2%の水中で乳化した。3.2%のN−オクタデシル−N,N−ジメチル−トリメトキシシリルプロピルアンモニウムクロリドを、生成したエマルションに添加した。4.8% TEOSを、エマルションに攪拌しながら添加した。中位径3μmのマイクロカプセルを懸濁液中で生成した。マイクロカプセルは、シラノール末端PDMSのコアと、シリカ単位及びN−オクタデシル−N,N−ジメチル−トリメトキシシリルプロピルアンモニウムクロリド由来のカチオン性シロキサン単位を含むTEOSのネットワークポリマーのシェルとを含んでいた。
−木材:サイズ50×27×18mmのホワイトパインのブロック。
−パインのブロックを、一定重量が記録されるまで、40℃のオーブン中で乾燥する(24時間間隔)。
−ブロックを、4kPa(40mbar)で、20分間、真空下に置く(図1A)。撥水性組成物をフラスコ内に入れ、木質ブロックを浸水させる(図1B)。
−ブロックを、大気圧下、20分間、撥水性組成物(1%活物質)に浸す(図1C)。
−次いで、ブロックを取り除き、ペーパーで軽く叩いて乾燥し、その重量を記録する。
−次いで、ブロックを40℃のオーブン中で4日間乾燥する。
−上で処理されたブロックを、2片のガラス上に直立に(最小断面27×18mmを接する面にして)置き、木質ブロックの僅か2mmのみが水に接触することを確認する(図2)。
−毛管力が水吸収率を促進する。
−次いで、ブロックを取り除き、ペーパーで軽く叩いて乾燥し、秤量してガラス棒の上に再度置く。次いで、水と接触させてから1、3、6、8及び24時間後に重量を記録する。
Claims (10)
- 多孔質製品又は前記製品を与える組成物を撥水性材料で処理することによって前記製品の疎水性を向上する方法であって、前記多孔質製品又は前記製品を与える組成物がマイクロカプセルの水性懸濁液で処理され、前記マイクロカプセルが、撥水性オルガノポリシロキサンコア材と、シリカ単位を含むケイ素系ネットワークポリマーのシェルと、を含むことを特徴とする、方法。
- 前記撥水性オルガノポリシロキサンコア材がポリジメチルシロキサンを含む、請求項2に記載の方法。
- 前記マイクロカプセルが、テトラアルコキシシランを含む水反応性ケイ素化合物を、撥水性オルガノポリシロキサンの水性エマルションに添加することによって得られ、前記水反応性ケイ素化合物が、前記エマルション中の液滴の界面で、縮合し、重合して、前記マイクロカプセルを形成する、請求項1又は2に記載の方法。
- 前記水反応性ケイ素化合物がテトラエトキシシランである、請求項3に記載の方法。
- 四級化アミノアルキルアルコキシシランを、前記水反応性ケイ素化合物より前、又は同時に、前記水性エマルションに添加する、請求項3又は4に記載の方法。
- 撥水性オルガノポリシロキサンコア材と、シリカ単位を含むケイ素系ネットワークポリマーのシェルとを含むマイクロカプセルを、セメント系組成物に添加し、前記組成物を成形し硬化してセメント系製品を形成する、請求項1に記載の方法。
- 前記マイクロカプセルを発泡性セメント系組成物に添加する、撥水性気泡セメント製品を作製するための、請求項6に記載の方法。
- 撥水性オルガノポリシロキサンコア材と、シリカ単位を含むケイ素系ネットワークポリマーのシェルとを含むマイクロカプセルを、粘土系組成物に添加し、前記組成物を成形し硬化してレンガ又はタイル製品を形成する、請求項1に記載の方法。
- 撥水性オルガノポリシロキサンコア材と、シリカ単位を含むケイ素系ネットワークポリマーのシェルと、を含む、多孔質製品のための撥水剤としてのマイクロカプセルの使用。
- 前記多孔質製品が、セメント系基材、粘土系レンガ、石膏系基材、石灰系基材又は木質系基材からなる群から選択される、請求項9に記載のマイクロカプセルの使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB201207662A GB201207662D0 (en) | 2012-05-02 | 2012-05-02 | Water repellent organopolysiloxane materials |
GB1207662.6 | 2012-05-02 | ||
PCT/EP2013/059081 WO2013164381A1 (en) | 2012-05-02 | 2013-05-02 | Water repellent organopolysiloxane materials |
Publications (2)
Publication Number | Publication Date |
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JP2015525246A true JP2015525246A (ja) | 2015-09-03 |
JP6178408B2 JP6178408B2 (ja) | 2017-08-09 |
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JP2015509433A Active JP6178408B2 (ja) | 2012-05-02 | 2013-05-02 | 撥水性オルガノポリシロキサン材料 |
Country Status (9)
Country | Link |
---|---|
US (1) | US20150087747A1 (ja) |
EP (1) | EP2844383B1 (ja) |
JP (1) | JP6178408B2 (ja) |
CN (1) | CN104271226B (ja) |
GB (1) | GB201207662D0 (ja) |
IN (1) | IN2014DN09957A (ja) |
RU (1) | RU2634780C2 (ja) |
SG (1) | SG11201406783PA (ja) |
WO (1) | WO2013164381A1 (ja) |
Cited By (3)
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KR20200052514A (ko) * | 2018-11-06 | 2020-05-15 | (주)제이엔티아이엔씨 | 건축물의 콘크리트 구조체의 미세기공에 대한 침투율을 조절할 수 있는 콘크리트 보호재의 제조방법 및 이를 이용하여 제조된 건축물의 콘크리트 보호재 |
WO2021187520A1 (ja) * | 2020-03-17 | 2021-09-23 | ダウ・東レ株式会社 | プレキャストコンクリート成形体 |
WO2021187522A1 (ja) * | 2020-03-17 | 2021-09-23 | ダウ・東レ株式会社 | セメント組成物及びその硬化物 |
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KR102554516B1 (ko) * | 2017-01-30 | 2023-07-13 | 다우 도레이 캄파니 리미티드 | 콘크리트 구조물용 코팅제 |
JP6926925B2 (ja) * | 2017-10-17 | 2021-08-25 | 信越化学工業株式会社 | シリカ被覆シリコーンエラストマー球状粒子の製造方法及びシリカ被覆シリコーンエラストマー球状粒子 |
CN111410454A (zh) * | 2019-01-08 | 2020-07-14 | 疏科纳米疏水科技(嘉兴)有限公司 | 一种制备高效内掺型纳米超疏水混凝土或水泥砂浆的方法 |
CN111908860B (zh) * | 2020-07-09 | 2021-12-21 | 长安大学 | 寒区裂缝自愈合超高性能水泥基复合材料及制备方法 |
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- 2012-05-02 GB GB201207662A patent/GB201207662D0/en not_active Ceased
-
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- 2013-05-02 SG SG11201406783PA patent/SG11201406783PA/en unknown
- 2013-05-02 IN IN9957DEN2014 patent/IN2014DN09957A/en unknown
- 2013-05-02 RU RU2014145021A patent/RU2634780C2/ru active
- 2013-05-02 JP JP2015509433A patent/JP6178408B2/ja active Active
- 2013-05-02 EP EP13720910.2A patent/EP2844383B1/en active Active
- 2013-05-02 CN CN201380022769.7A patent/CN104271226B/zh active Active
- 2013-05-02 WO PCT/EP2013/059081 patent/WO2013164381A1/en active Application Filing
- 2013-05-02 US US14/396,229 patent/US20150087747A1/en not_active Abandoned
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KR20200052514A (ko) * | 2018-11-06 | 2020-05-15 | (주)제이엔티아이엔씨 | 건축물의 콘크리트 구조체의 미세기공에 대한 침투율을 조절할 수 있는 콘크리트 보호재의 제조방법 및 이를 이용하여 제조된 건축물의 콘크리트 보호재 |
KR102196117B1 (ko) | 2018-11-06 | 2020-12-30 | 박명주 | 건축물의 콘크리트 구조체의 미세기공에 대한 침투율을 조절할 수 있는 콘크리트 보호재의 제조방법 및 이를 이용하여 제조된 건축물의 콘크리트 보호재 |
WO2021187520A1 (ja) * | 2020-03-17 | 2021-09-23 | ダウ・東レ株式会社 | プレキャストコンクリート成形体 |
WO2021187522A1 (ja) * | 2020-03-17 | 2021-09-23 | ダウ・東レ株式会社 | セメント組成物及びその硬化物 |
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EP2844383A1 (en) | 2015-03-11 |
RU2634780C2 (ru) | 2017-11-03 |
JP6178408B2 (ja) | 2017-08-09 |
IN2014DN09957A (ja) | 2015-08-14 |
GB201207662D0 (en) | 2012-06-13 |
WO2013164381A1 (en) | 2013-11-07 |
US20150087747A1 (en) | 2015-03-26 |
CN104271226A (zh) | 2015-01-07 |
RU2014145021A (ru) | 2016-06-27 |
CN104271226B (zh) | 2016-12-21 |
SG11201406783PA (en) | 2014-11-27 |
EP2844383B1 (en) | 2018-04-04 |
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