CN104292251B - 一种防水剂、制备方法及其应用 - Google Patents
一种防水剂、制备方法及其应用 Download PDFInfo
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- CN104292251B CN104292251B CN201410464462.9A CN201410464462A CN104292251B CN 104292251 B CN104292251 B CN 104292251B CN 201410464462 A CN201410464462 A CN 201410464462A CN 104292251 B CN104292251 B CN 104292251B
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- Prior art keywords
- water
- silicon chip
- carboxylic
- cyclopropylmethylamide
- proofing
- 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.)
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- 238000004078 waterproofing Methods 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 84
- 239000010703 silicon Substances 0.000 claims abstract description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 44
- -1 fluoroalkyl saline Chemical compound 0.000 claims abstract description 38
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 26
- 239000007822 coupling agent Substances 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 104
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 78
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- 235000019441 ethanol Nutrition 0.000 claims description 17
- 150000002460 imidazoles Chemical class 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000005886 esterification reaction Methods 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 229910000077 silane Inorganic materials 0.000 claims description 8
- 238000010792 warming Methods 0.000 claims description 8
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 claims description 7
- 230000006837 decompression Effects 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 5
- 238000011938 amidation process Methods 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- 238000005292 vacuum distillation Methods 0.000 claims description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 2
- BHWUCEATHBXPOV-UHFFFAOYSA-N 2-triethoxysilylethanamine Chemical group CCO[Si](CCN)(OCC)OCC BHWUCEATHBXPOV-UHFFFAOYSA-N 0.000 claims description 2
- QHQNYHZHLAAHRW-UHFFFAOYSA-N 2-trimethoxysilylethanamine Chemical compound CO[Si](OC)(OC)CCN QHQNYHZHLAAHRW-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 230000004044 response Effects 0.000 claims description 2
- 239000001384 succinic acid Substances 0.000 claims description 2
- 229940014800 succinic anhydride Drugs 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 claims 1
- 238000001338 self-assembly Methods 0.000 abstract description 45
- 239000000463 material Substances 0.000 abstract description 21
- 150000003376 silicon Chemical class 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 239000000126 substance Substances 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 7
- 239000011159 matrix material Substances 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 78
- 230000000640 hydroxylating effect Effects 0.000 description 26
- 238000004140 cleaning Methods 0.000 description 13
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000008367 deionised water Substances 0.000 description 12
- 229910021641 deionized water Inorganic materials 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229910001882 dioxygen Inorganic materials 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000013557 residual solvent Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000002242 deionisation method Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000002120 nanofilm Substances 0.000 description 5
- 238000010998 test method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- DXAOXPFFQPRUGW-UHFFFAOYSA-N FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)F.Cl Chemical compound FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)F.Cl DXAOXPFFQPRUGW-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- WWBITQUCWSFVNB-UHFFFAOYSA-N 3-silylpropan-1-amine Chemical compound NCCC[SiH3] WWBITQUCWSFVNB-UHFFFAOYSA-N 0.000 description 1
- 241000252506 Characiformes Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005376 alkyl siloxane group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- YENOLDYITNSPMQ-UHFFFAOYSA-N carboxysilicon Chemical compound OC([Si])=O YENOLDYITNSPMQ-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- FWARNCMTCYKUBS-UHFFFAOYSA-N ethyl n-(ethoxycarbonylcarbamoyl)carbamate Chemical compound CCOC(=O)NC(=O)NC(=O)OCC FWARNCMTCYKUBS-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Laminated Bodies (AREA)
Abstract
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CN201410464462.9A CN104292251B (zh) | 2014-09-12 | 2014-09-12 | 一种防水剂、制备方法及其应用 |
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CN201410464462.9A CN104292251B (zh) | 2014-09-12 | 2014-09-12 | 一种防水剂、制备方法及其应用 |
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CN104292251A CN104292251A (zh) | 2015-01-21 |
CN104292251B true CN104292251B (zh) | 2017-02-15 |
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Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN105801618A (zh) * | 2016-05-04 | 2016-07-27 | 厦门建霖工业有限公司 | 一种含氟超疏水疏油剂的制备方法 |
CN112127157B (zh) * | 2020-09-28 | 2021-11-09 | 苏州大学 | 一种聚氨基酸接枝改性拒水织物及其制备方法 |
CN112194638B (zh) * | 2020-09-28 | 2022-07-19 | 苏州大学 | 苯胺基酸酐及其制备方法与聚氨基酸接枝链 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1487959A (zh) * | 2001-01-19 | 2004-04-07 | 3M | 用于使基材防油和防水的水溶性或可水分散氟化物硅烷 |
CN101889018A (zh) * | 2007-12-04 | 2010-11-17 | 纳幕尔杜邦公司 | 氟代烷基硅烷 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58172245A (ja) * | 1982-04-02 | 1983-10-11 | Asahi Glass Co Ltd | ガラスの表面処理剤 |
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- 2014-09-12 CN CN201410464462.9A patent/CN104292251B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1487959A (zh) * | 2001-01-19 | 2004-04-07 | 3M | 用于使基材防油和防水的水溶性或可水分散氟化物硅烷 |
CN101889018A (zh) * | 2007-12-04 | 2010-11-17 | 纳幕尔杜邦公司 | 氟代烷基硅烷 |
Non-Patent Citations (1)
Title |
---|
氟硅烷自组装单分子膜的制备及其摩擦学性能;谷国团等;《物理化学学报》;20020731;第669-672页 * |
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