CN1858076A - 细乳液聚合法制备有机硅改性丙烯酸酯共聚物乳液的方法 - Google Patents
细乳液聚合法制备有机硅改性丙烯酸酯共聚物乳液的方法 Download PDFInfo
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- CN1858076A CN1858076A CN 200610050461 CN200610050461A CN1858076A CN 1858076 A CN1858076 A CN 1858076A CN 200610050461 CN200610050461 CN 200610050461 CN 200610050461 A CN200610050461 A CN 200610050461A CN 1858076 A CN1858076 A CN 1858076A
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- organic silicon
- methyl
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- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000000839 emulsion Substances 0.000 title claims abstract description 20
- 229920001577 copolymer Polymers 0.000 title claims abstract description 15
- 229910052710 silicon Inorganic materials 0.000 title claims description 15
- 239000010703 silicon Substances 0.000 title claims description 15
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims description 12
- 230000000379 polymerizing effect Effects 0.000 title abstract 2
- 239000000178 monomer Substances 0.000 claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 23
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 16
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 16
- 238000007599 discharging Methods 0.000 claims abstract description 11
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 11
- 239000003999 initiator Substances 0.000 claims abstract description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 24
- 239000012071 phase Substances 0.000 claims description 23
- 239000008346 aqueous phase Substances 0.000 claims description 20
- -1 (methyl) acryloyl-oxy methyl Chemical group 0.000 claims description 19
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 10
- 239000004141 Sodium laurylsulphate Substances 0.000 claims description 10
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 10
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 10
- 150000001282 organosilanes Chemical class 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 7
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- 229960003328 benzoyl peroxide Drugs 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000006353 oxyethylene group Chemical group 0.000 claims description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 abstract description 9
- 230000008569 process Effects 0.000 abstract description 8
- 238000001816 cooling Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000010008 shearing Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 238000009833 condensation Methods 0.000 description 11
- 230000005494 condensation Effects 0.000 description 11
- 238000000576 coating method Methods 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 229920000058 polyacrylate Polymers 0.000 description 9
- 239000004159 Potassium persulphate Substances 0.000 description 8
- 238000013019 agitation Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000006392 deoxygenation reaction Methods 0.000 description 8
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 238000010907 mechanical stirring Methods 0.000 description 8
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 8
- 235000019394 potassium persulphate Nutrition 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000002525 ultrasonication Methods 0.000 description 8
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 125000005375 organosiloxane group Chemical group 0.000 description 3
- 230000002028 premature Effects 0.000 description 3
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 3
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000006911 nucleation Effects 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 238000001016 Ostwald ripening Methods 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- ARLJCLKHRZGWGL-UHFFFAOYSA-N ethenylsilicon Chemical compound [Si]C=C ARLJCLKHRZGWGL-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VLCAYQIMSMPEBW-UHFFFAOYSA-N methyl 3-hydroxy-2-methylidenebutanoate Chemical compound COC(=O)C(=C)C(C)O VLCAYQIMSMPEBW-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 238000002464 physical blending Methods 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
实施例 | 平均粒径(nm) | 接触角(度) | 吸水率(%) | 贮存稳定性 |
1 | 76.5 | 95.9 | 8.52 | 好 |
2 | 70.4 | 103.2 | 6.36 | 好 |
3 | 70.9 | 105.5 | 6.79 | 好 |
比较实施例1 | 80.9 | 73.9 | 13.97 | 好 |
比较实施例2 | 74.3 | 104.6 | 6.96 | 好 |
比较实施例3 | 74.8 | 104.7 | 6.54 | 好 |
4 | 72.3 | 105.7 | 5.39 | 好 |
5 | 73.4 | 104.8 | 6.14 | 好 |
Claims (6)
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CNB2006100504615A CN100348627C (zh) | 2006-04-21 | 2006-04-21 | 细乳液聚合法制备有机硅改性丙烯酸酯共聚物乳液的方法 |
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CNB2006100504615A CN100348627C (zh) | 2006-04-21 | 2006-04-21 | 细乳液聚合法制备有机硅改性丙烯酸酯共聚物乳液的方法 |
Publications (2)
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CN1858076A true CN1858076A (zh) | 2006-11-08 |
CN100348627C CN100348627C (zh) | 2007-11-14 |
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CNB2006100504615A Expired - Fee Related CN100348627C (zh) | 2006-04-21 | 2006-04-21 | 细乳液聚合法制备有机硅改性丙烯酸酯共聚物乳液的方法 |
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CN (1) | CN100348627C (zh) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100560592C (zh) * | 2006-12-13 | 2009-11-18 | 中国科学院广州化学研究所 | 一种含硅(甲基)丙烯酸酯单体及其共聚物和它们的制备方法 |
CN101386663B (zh) * | 2008-10-30 | 2010-10-06 | 上海三瑞高分子材料有限公司 | 一种多功能丙烯酸酯乳液 |
CN101575398B (zh) * | 2009-06-05 | 2011-04-20 | 天津碧海蓝天水性高分子材料有限公司 | 有机硅改性丙烯酸酯乳液及用于制造无粉手套的涂饰剂的制备方法 |
CN101638451B (zh) * | 2008-08-01 | 2012-05-09 | 上海富臣化工有限公司 | 水性木器漆用纳米聚丙烯酸酯乳液及其制备方法 |
CN102464784A (zh) * | 2010-11-19 | 2012-05-23 | 北京佳盛世纪科技有限公司 | 一种有机硅改性丙烯酸酯共聚物的合成方法 |
CN101293941B (zh) * | 2007-04-24 | 2013-05-29 | 关西涂料株式会社 | 颜料分散性树脂的生产方法 |
CN105218762A (zh) * | 2015-10-28 | 2016-01-06 | 广州中国科学院工业技术研究院 | 新型有机硅拒水剂及其制备方法 |
CN106916263A (zh) * | 2017-02-08 | 2017-07-04 | 佛山沛涂科技有限公司 | 一种有机硅改性汽车漆用水性丙烯酸树脂的方法 |
CN117468268A (zh) * | 2023-12-27 | 2024-01-30 | 湖南大道新材料有限公司 | 一种阻水纸袋及其制备方法与应用 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI425083B (zh) * | 2011-12-08 | 2014-02-01 | Taiwan Textile Res Inst | 乳液之製造方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1594380A (zh) * | 2004-07-09 | 2005-03-16 | 中山大学 | 一种硅丙乳液的制备方法 |
-
2006
- 2006-04-21 CN CNB2006100504615A patent/CN100348627C/zh not_active Expired - Fee Related
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100560592C (zh) * | 2006-12-13 | 2009-11-18 | 中国科学院广州化学研究所 | 一种含硅(甲基)丙烯酸酯单体及其共聚物和它们的制备方法 |
CN101293941B (zh) * | 2007-04-24 | 2013-05-29 | 关西涂料株式会社 | 颜料分散性树脂的生产方法 |
CN101638451B (zh) * | 2008-08-01 | 2012-05-09 | 上海富臣化工有限公司 | 水性木器漆用纳米聚丙烯酸酯乳液及其制备方法 |
CN101386663B (zh) * | 2008-10-30 | 2010-10-06 | 上海三瑞高分子材料有限公司 | 一种多功能丙烯酸酯乳液 |
CN101575398B (zh) * | 2009-06-05 | 2011-04-20 | 天津碧海蓝天水性高分子材料有限公司 | 有机硅改性丙烯酸酯乳液及用于制造无粉手套的涂饰剂的制备方法 |
CN102464784A (zh) * | 2010-11-19 | 2012-05-23 | 北京佳盛世纪科技有限公司 | 一种有机硅改性丙烯酸酯共聚物的合成方法 |
CN105218762A (zh) * | 2015-10-28 | 2016-01-06 | 广州中国科学院工业技术研究院 | 新型有机硅拒水剂及其制备方法 |
CN106916263A (zh) * | 2017-02-08 | 2017-07-04 | 佛山沛涂科技有限公司 | 一种有机硅改性汽车漆用水性丙烯酸树脂的方法 |
CN117468268A (zh) * | 2023-12-27 | 2024-01-30 | 湖南大道新材料有限公司 | 一种阻水纸袋及其制备方法与应用 |
CN117468268B (zh) * | 2023-12-27 | 2024-03-22 | 湖南大道新材料有限公司 | 一种阻水纸袋及其制备方法与应用 |
Also Published As
Publication number | Publication date |
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CN100348627C (zh) | 2007-11-14 |
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