CN100547044C - The preparation method of aqueous polyurethane and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive - Google Patents
The preparation method of aqueous polyurethane and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive Download PDFInfo
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- CN100547044C CN100547044C CNB2006100960374A CN200610096037A CN100547044C CN 100547044 C CN100547044 C CN 100547044C CN B2006100960374 A CNB2006100960374 A CN B2006100960374A CN 200610096037 A CN200610096037 A CN 200610096037A CN 100547044 C CN100547044 C CN 100547044C
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- 239000011248 coating agent Substances 0.000 title claims abstract description 26
- 238000000576 coating method Methods 0.000 title claims abstract description 26
- 239000000853 adhesive Substances 0.000 title claims abstract description 24
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 24
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 20
- 239000004814 polyurethane Substances 0.000 title claims abstract description 17
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 17
- 150000004812 organic fluorine compounds Chemical class 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001298 alcohols Chemical class 0.000 claims abstract description 13
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims abstract description 12
- DODVWSSKXYVHOR-UHFFFAOYSA-N fluoro(hydroxy)silicon Chemical compound O[Si]F DODVWSSKXYVHOR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 11
- XQSFXFQDJCDXDT-UHFFFAOYSA-N hydroxysilicon Chemical compound [Si]O XQSFXFQDJCDXDT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000009775 high-speed stirring Methods 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000008367 deionised water Substances 0.000 claims abstract description 5
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 3
- 230000001105 regulatory effect Effects 0.000 claims abstract description 3
- 239000001384 succinic acid Substances 0.000 claims abstract description 3
- -1 alcohol compounds Chemical class 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 5
- CVPISOYTFIHLKP-UHFFFAOYSA-N OC(O)[SiH3] Chemical compound OC(O)[SiH3] CVPISOYTFIHLKP-UHFFFAOYSA-N 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical group CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 3
- NHBNYQRCRFGJJA-UHFFFAOYSA-N ethyl(dihydroxy)silane Chemical compound CC[SiH](O)O NHBNYQRCRFGJJA-UHFFFAOYSA-N 0.000 claims description 3
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- 241000894006 Bacteria Species 0.000 abstract description 5
- 239000004744 fabric Substances 0.000 abstract description 2
- 230000002070 germicidal effect Effects 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 7
- 230000000845 anti-microbial effect Effects 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
Abstract
The present invention relates to the preparation method of a kind of aqueous polyurethane and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive.This method is with vulcabond and diatomic alcohol compounds, alkane silicol, hydroxyl fluorosilicon oil, dimethylol propionic acid reaction, produces end group to be-performed polymer of NCO, uses 1 then, the 4-chain expansion of succinic acid.Regulate the pH value to neutrality with amine at last, add the deionized water high-speed stirring that contains antiseptic-germicide, after adding water and regulating viscosity, promptly obtain water-proof air-moisture-permeable antibacterial adhesive coating.Coat the surface of fabric, water-proof air-moisture-permeable not only, also to common bacterium, mould has very strong germicidal action.
Description
Technical field
The present invention relates to a kind of polyurethane water-proof air-moisture-permeable coating adhesive, be specifically related to the preparation method of a kind of aqueous polyurethane and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive.Belong to field of chemical technology.
Background technology
Polyurethane water-proof air-moisture-permeable coating adhesive can be given the coating waterproof in weaving, the widespread use of leather field, saturating wet special efficacy.At present, the coating adhesive of urethane is emitted a large amount of deleterious organic solvents, not environmental protection of the utmost point still based on oiliness urethane when producing and be coated with.And novel water-base polyurethane material is dispersion medium because of using nontoxic water, and the utmost point has market potential.But aqueous coating glue is more vulnerable to the infringement of bacterium.
Summary of the invention
The objective of the invention is to overcome above-mentioned deficiency, a kind of high water-proof air-moisture-permeable performance that not only has is provided, and the preparation method of the anti-aqueous polyurethane that kills effect and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable coating adhesive can be arranged most of bacteriums.
The object of the present invention is achieved like this: the preparation method of a kind of aqueous polyurethane and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive, it is characterized in that it is with vulcabond and diatomic alcohol compounds, alkane silicol, hydroxyl fluorosilicon oil, dimethylol propionic acid reaction, produce end group to be-performed polymer of NCO; Use 1 then, the 4-chain expansion of succinic acid; Regulate the pH value to neutrality with amine at last, add the deionized water high-speed stirring that contains antiseptic-germicide, after adding water and regulating viscosity, promptly obtain water-proof air-moisture-permeable antibacterial adhesive coating.
Concrete technology of the present invention is: add diatomic alcohol compounds in reactor, alkane silicol and hydroxyl fluorosilicon oil, 100-120 ℃ vacuumized 1.5～2.5 hours, add dimethylol propionic acid, after the dissolving, cool to 70-80 ℃, add vulcabond and catalyzer dibutyl tin laurate (DBTDL), insulated and stirred 90-100min, be cooled to 60-70 ℃, add 1,4-butyleneglycol, insulated and stirred 40-50min, be cooled to 15-25 ℃, add the amine neutralization, add the deionized water that contains antiseptic-germicide, high-speed stirring, after adding water adjusting viscosity, promptly obtain water-proof air-moisture-permeable antibacterial adhesive coating.
Each material of the present invention is to react according to following proportioning:
-NCO :-OH=3-4: 1, wherein-NCO represents isocyanate group;
The mol ratio of alkane silicol, hydroxyl fluorosilicon oil and diatomic alcohol compounds is: the alkane silicol: the hydroxyl fluorosilicon oil: diatomic alcohol compounds=1: 0.4～0.6: 10～12;
The mol ratio of dimethylol propionic acid and diatomic alcohol compounds is: dimethylol propionic acid: diatomic alcohol compounds=1: 12～15;
1, the mol ratio of 4-butyleneglycol and diatomic alcohol compounds is: 1, and 4-butyleneglycol: diatomic alcohol compounds 1: 12～15.
Diatomic alcohol compounds of the present invention is polyoxyethylene glycol or polypropylene glycol;
Alkane silicol of the present invention is dihydroxy ethyl silane or dihydroxymethyl silane;
Amine of the present invention is quadrol or hexanediamine;
Vulcabond of the present invention is an isophorone diisocyanate (IPDI), 1,6-hexamethylene diisocyanate (HDI), tolylene diisocyanate (TDI) or diphenylmethanediisocyanate (MDI);
Molecular weight polyethylene glycol of the present invention is 800-1200; The polypropylene glycol molecular weight is 800-1200; The number-average molecular weight of water-proof air-moisture-permeable antibacterial adhesive coating is 10000-20000, and viscosity is 800-1000cps;
Antiseptic-germicide of the present invention is inorganic carrying silver antimicrobials, and median size is below the 5 μ m.
The present invention not only has high water-proof air-moisture-permeable performance, and can the anti-effect of killing be arranged to most of bacteriums.The present invention coats the surface of fabric, water-proof air-moisture-permeable not only, and also to common bacterium, mould has very strong germicidal action.
Embodiment
Embodiment 1:
Adding 120g polyoxyethylene glycol in flask (molecular weight: 1000), 8g dihydroxymethyl silane, 4g hydroxyl fluorosilicon oil, 100 ℃ vacuumized 2 hours, added the 8g dimethylol propionic acid, after the dissolving, cool to 72 ℃, add 28gHDI and 6 catalyzer DBTDL, insulated and stirred 90min, be cooled to 63 ℃, add 7.6g1, the 4-butyleneglycol, insulated and stirred 40min is cooled to 25 ℃, adds quadrol 10g, the water 228g that is dispersed with 6g and does not have airborne silver-colored silicon oxide is added fast, high-speed stirring 1 hour, product.Detect anti-microbial property (pressing JIS Z2801:2000 standard) after being coated with, its anti-microbial activity value is greater than 4.0.
Embodiment 2:
Adding 120g polypropylene glycol in flask (molecular weight: 1000), 10g dihydroxy ethyl silane, 5g hydroxyl fluorosilicon oil, 100 ℃ vacuumized 2 hours, added the 7.8g dimethylol propionic acid, after the dissolving, cool to 75 ℃, add 30gIPDI and 6 catalyzer DBTDL, insulated and stirred 90min.Be cooled to 60 ℃, adding 7.5g1, the 4-butyleneglycol, insulated and stirred 40min is cooled to 20 ℃, adds quadrol 9g, does not have the water 230 grams adding fast of airborne silver-colored titanium oxide with being dispersed with 6g, and high-speed stirring 1 hour gets product.Detect anti-microbial property (pressing JIS Z2801:2000 standard) after being coated with, its anti-microbial activity value is greater than 4.0.
Embodiment 3:
Adding 120g polyoxyethylene glycol in flask (molecular weight: 800), 9g dihydroxymethyl silane, 4.5g hydroxyl fluorosilicon oil, 100 ℃ vacuumized 2 hours, added the 9g dimethylol propionic acid, after the dissolving, cool to 72 ℃, add 28gHDI and 6 catalyzer DBTDL, insulated and stirred 90min.Be cooled to 65 ℃, add 8.0g1, the 4-butyleneglycol, insulated and stirred 40min is cooled to 20 ℃, adds hexanediamine 10g, the water 230g that is dispersed with 8g and does not have airborne silver-colored silicon oxide is added fast, high-speed stirring 1 hour, product.Detect anti-microbial property (pressing JIS Z2801:2000 standard) after being coated with, its anti-microbial activity value is greater than 4.7.
Claims (8)
1, the preparation method of a kind of aqueous polyurethane and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive, it is characterized in that it is with vulcabond and diatomic alcohol compounds, alkane silicol, hydroxyl fluorosilicon oil, dimethylol propionic acid reaction, produce end group to be-performed polymer of NCO; Use 1 then, the 4-chain expansion of succinic acid; Regulate the pH value to neutrality with amine at last, add the deionized water high-speed stirring that contains antiseptic-germicide, after adding water and regulating viscosity, promptly obtain water-proof air-moisture-permeable antibacterial adhesive coating,
Concrete technology is: add diatomic alcohol compounds, alkane silicol and hydroxyl fluorosilicon oil in reactor, 100-120 ℃ vacuumized 1.5～2.5 hours, add dimethylol propionic acid, after the dissolving, cool to 70-80 ℃, add vulcabond and catalyzer dibutyl tin laurate, insulated and stirred 90-100min, be cooled to 60-70 ℃, add 1,4-butyleneglycol, insulated and stirred 40-50min, be cooled to 15-25 ℃, add the amine neutralization, add the deionized water that contains antiseptic-germicide, high-speed stirring, after adding water adjusting viscosity, promptly obtain water-proof air-moisture-permeable antibacterial adhesive coating.
2, the preparation method of a kind of aqueous polyurethane according to claim 1 and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive is characterized in that each material is to react according to following proportioning:
-NCO :-OH=3-4: 1, wherein-NCO represents isocyanate group;
The mol ratio of alkane silicol, hydroxyl fluorosilicon oil and diatomic alcohol compounds is: the alkane silicol: the hydroxyl fluorosilicon oil: diatomic alcohol compounds=1: 0.4～0.6: 10～12;
The mol ratio of dimethylol propionic acid and diatomic alcohol compounds is: dimethylol propionic acid: diatomic alcohol compounds=1: 12～15;
1, the mol ratio of 4-butyleneglycol and polyol compound is: 1, and 4-butyleneglycol: polyol compound 1: 12～15.
3, the preparation method of a kind of aqueous polyurethane according to claim 2 and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive is characterized in that described diatomic alcohol compounds is polyoxyethylene glycol or polypropylene glycol.
4, the preparation method of a kind of aqueous polyurethane according to claim 2 and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive is characterized in that described alkane silicol is dihydroxy ethyl silane or dihydroxymethyl silane.
5, the preparation method of a kind of aqueous polyurethane according to claim 2 and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive is characterized in that described amine is quadrol or hexanediamine.
6, the preparation method of a kind of aqueous polyurethane according to claim 2 and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive, it is characterized in that described vulcabond is an isophorone diisocyanate, 1,6-hexamethylene diisocyanate, tolylene diisocyanate or diphenylmethanediisocyanate.
7, the preparation method of a kind of aqueous polyurethane according to claim 3 and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive is characterized in that described molecular weight polyethylene glycol is 800-1200; The polypropylene glycol molecular weight is 800-1200; The number-average molecular weight of water-proof air-moisture-permeable antibacterial adhesive coating is 10000-20000, and viscosity is 800-1000cps.
8, the preparation method of a kind of aqueous polyurethane according to claim 2 and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive is characterized in that described antiseptic-germicide is inorganic carrying silver antimicrobials, and median size is below the 5 μ m.
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| CNB2006100960374A CN100547044C (en) | 2006-09-14 | 2006-09-14 | The preparation method of aqueous polyurethane and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive |
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| CNB2006100960374A CN100547044C (en) | 2006-09-14 | 2006-09-14 | The preparation method of aqueous polyurethane and organosilicon, organofluorine copllymerized water-proof air-moisture-permeable antibacterial coating adhesive |
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| CN100547044C true CN100547044C (en) | 2009-10-07 |
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| CN101161747B (en) * | 2007-09-20 | 2010-06-02 | 华明扬 | Preparation method of polycaprolactone siloxane aqueous polyurethane paint for woodenware |
| CN101157822B (en) * | 2007-09-20 | 2010-06-16 | 华明扬 | Method for preparing casing fabric wave-absorption coating glue |
| CN100560673C (en) * | 2007-09-20 | 2009-11-18 | 华明扬 | The preparation method of environment-friendly type wear-resisting weather-proof brightener used for artificial leather |
| CN101186798B (en) * | 2007-11-08 | 2012-03-28 | 江阴市诺科科技有限公司 | Method for preparing water polyurethane siloxane ventilating coating adhesive used for automobiles and shoes |
| CN102418277A (en) * | 2011-11-01 | 2012-04-18 | 吴江市北厍盛源纺织品助剂厂 | Preparation method of antibacterial polyurethane textile finishing liquid |
| CN102505491A (en) * | 2011-11-01 | 2012-06-20 | 吴江市北厍盛源纺织品助剂厂 | Synthesizing method of polyurethane-modified organosilicon antimicrobial auxiliary agent |
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| CN103554426B (en) * | 2013-10-29 | 2015-08-26 | 上海汇得化工有限公司 | The burnt discoloration wet polyurethane resin that a kind of hydrolytic resistance is good |
| CN104499295A (en) * | 2014-11-17 | 2015-04-08 | 浙江梦娜袜业股份有限公司 | Water, oil and dirty repellent finishing agent for silk stockings and silk stocking production technology |
| CN105504194B (en) * | 2015-12-28 | 2019-01-01 | 安徽安大华泰新材料有限公司 | A kind of preparation method of hydrophobic thermal polyurethane resin |
| CN106480724B (en) * | 2016-11-16 | 2018-08-24 | 丹东优耐特纺织品有限公司 | The processing method of anti-aging, cold-resistant, antibacterial, high moisture-inhibiting raincoat fabric |
| CN107190350A (en) * | 2017-05-18 | 2017-09-22 | 颍上县鸿达纺织有限公司 | A kind of uvioresistant waterproof spinning of environmental sanitation fabric |
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