CN100497506C - Water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating preparing method - Google Patents
Water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating preparing method Download PDFInfo
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- CN100497506C CN100497506C CNB2006100960410A CN200610096041A CN100497506C CN 100497506 C CN100497506 C CN 100497506C CN B2006100960410 A CNB2006100960410 A CN B2006100960410A CN 200610096041 A CN200610096041 A CN 200610096041A CN 100497506 C CN100497506 C CN 100497506C
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- water
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- adhesive coating
- proof air
- antibacterial adhesive
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 239000011248 coating agent Substances 0.000 title claims abstract description 25
- 238000000576 coating method Methods 0.000 title claims abstract description 25
- 239000000853 adhesive Substances 0.000 title claims abstract description 23
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 23
- 239000004814 polyurethane Substances 0.000 title claims abstract description 17
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 17
- 239000004593 Epoxy Substances 0.000 title claims abstract description 16
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 19
- 238000000034 method Methods 0.000 title abstract 2
- 239000003822 epoxy resin Substances 0.000 claims abstract description 12
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 12
- -1 alcohol compound Chemical class 0.000 claims abstract description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- 239000008367 deionised water Substances 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims abstract description 3
- 150000001298 alcohols Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 238000009775 high-speed stirring Methods 0.000 claims description 7
- 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 5
- 229920001451 polypropylene glycol Polymers 0.000 claims description 5
- 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
- 229910021641 deionized water Inorganic materials 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-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
- 239000001384 succinic acid Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 2
- 241000790917 Dioxys <bee> Species 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 125000005442 diisocyanate group Chemical group 0.000 abstract 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 230000000845 anti-microbial effect Effects 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 4
- 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
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CVPISOYTFIHLKP-UHFFFAOYSA-N OC(O)[SiH3] Chemical compound OC(O)[SiH3] CVPISOYTFIHLKP-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 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
- NHBNYQRCRFGJJA-UHFFFAOYSA-N ethyl(dihydroxy)silane Chemical compound CC[SiH](O)O NHBNYQRCRFGJJA-UHFFFAOYSA-N 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- XQSFXFQDJCDXDT-UHFFFAOYSA-N hydroxysilicon Chemical compound [Si]O XQSFXFQDJCDXDT-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 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)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention relates to aquosity polyurethane/epoxy copolymerization water proof gasper drenching antibiotic coating adhesive preparing method. It includes the following steps: using diisocyanate to react with diatomic alcohol compound, low molecule epoxy resin, and dioxy methyl propionic acid to produce performed polymer with -NCO end group, enlarging chain by 1, 4 butylene glycol; using amine to adjust pH value to neutrality; adding de-ionized water contains anti-bacterial agent to stir at high speed; adding water to adjust viscosity. It can be coated at the fabric surface to realize water proof gasper drenching, and kill mold.
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/epoxy copolymerized 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 can the anti-preparation method who kills the water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating of effect be arranged most of bacteriums.
The object of the present invention is achieved like this: a kind of preparation method of water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating, it is characterized in that it is with vulcabond and diatomic alcohol compounds, low molecular weight epoxy, dimethylol propionic acid reaction, produce end group to be-performed polymer of NCO; Use 1,4-chain expansion of succinic acid then; 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, low-molecular-weight epoxy resin 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 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 low-molecular-weight epoxy resin and diatomic alcohol compounds is: low-molecular-weight epoxy resin: diatomic alcohol compounds=1:10～12;
The mol ratio of dimethylol propionic acid and diatomic alcohol compounds is: dimethylol propionic acid: diatomic alcohol compounds=1:12～15;
The mol ratio of 1,4-butyleneglycol and diatomic alcohol compounds is: 1,4-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 IPDI, HDI, TDI or modification diimine 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 weight concentration of antiseptic-germicide is 1-2%.
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 low-molecular-weight epoxy resin E51,100 ℃ vacuumized 2 hours, add the 8g dimethylol propionic acid, after the dissolving, cool to 72 ℃, add 28gHDI and 6 catalyzer DBTDL, insulated and stirred 90min is cooled to 63 ℃, add 7.6g 1,4-butyleneglycol, insulated and stirred 40min, be cooled to 25 ℃, add 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 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 2:
Adding 120g polypropylene glycol in flask (molecular weight: 1000), 10g low-molecular-weight epoxy resin E44,100 ℃ vacuumized 2 hours, add 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 7.5g 1,4-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 low-molecular-weight epoxy resin E20,100 ℃ vacuumized 2 hours, added the 9g dimethylol propionic acid, after the dissolving, cooled to 72 ℃, added 28gHDI and 6 catalyzer DBTDL, insulated and stirred 90min.Be cooled to 65 ℃, add 8.0g 1,4-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, a kind of preparation method of water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating, it is characterized in that it is with vulcabond and diatomic alcohol compounds, low-molecular-weight epoxy resin, dimethylol propionic acid reaction, produce end group to be-performed polymer of NCO; Use 1,4-chain expansion of succinic acid then; 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, described diatomic alcohol compounds is polyoxyethylene glycol or polypropylene glycol.
2, the preparation method of a kind of water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating according to claim 1, it is characterized in that concrete technology is: in reactor, add diatomic alcohol compounds, low-molecular-weight epoxy resin, 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 is cooled to 60-70 ℃, adds 1,4-butyleneglycol, insulated and stirred 40-50min is cooled to 15-25 ℃, adds the amine neutralization, add the deionized water that contains antiseptic-germicide, high-speed stirring after adding water and regulating viscosity, promptly obtains water-proof air-moisture-permeable antibacterial adhesive coating.
3, the preparation method of a kind of water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating according to claim 2 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 low-molecular-weight epoxy resin and diatomic alcohol compounds is: low-molecular-weight epoxy resin Resins, epoxy: diatomic alcohol compounds=1:10～12;
The mol ratio of dimethylol propionic acid and diatomic alcohol compounds is: dimethylol propionic acid: diatomic alcohol compounds=1:12～15;
The mol ratio of 1,4-butyleneglycol and diatomic alcohol compounds is: 1,4-butyleneglycol: diatomic alcohol compounds 1:12～15.
4, the preparation method of a kind of water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating according to claim 3 is characterized in that described low-molecular-weight epoxy resin is E20, E44, E51.
5, the preparation method of a kind of water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating according to claim 3 is characterized in that described amine is quadrol or hexanediamine.
6, the preparation method of a kind of water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating according to claim 1 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.
7, the preparation method of a kind of water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating according to claim 3 is characterized in that described antiseptic-germicide is inorganic carrying silver antimicrobials, and median size is below the 5 μ m.
8, the preparation method of a kind of water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating according to claim 7, the weight concentration that it is characterized in that described antiseptic-germicide is 1-2%.
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| Application Number | Priority Date | Filing Date | Title |
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| CNB2006100960410A CN100497506C (en) | 2006-09-14 | 2006-09-14 | Water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating preparing method |
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| CNB2006100960410A CN100497506C (en) | 2006-09-14 | 2006-09-14 | Water-based polyurethane/epoxy copolymerized water-proof air-moisture-permeable antibacterial adhesive coating preparing method |
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| CN1935920A CN1935920A (en) | 2007-03-28 |
| CN100497506C true CN100497506C (en) | 2009-06-10 |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348982A (en) * | 2015-11-13 | 2016-02-24 | 安徽广源科技发展有限公司 | High-toughness environmental-friendly water-borne coating |
| CN105348981A (en) * | 2015-11-13 | 2016-02-24 | 安徽广源科技发展有限公司 | Environmental-friendly anti-cracking water-borne coating |
| CN105348984A (en) * | 2015-11-13 | 2016-02-24 | 安徽广源科技发展有限公司 | Impact-resistant eco-friendly aqueous paint |
| CN106676899A (en) * | 2016-12-30 | 2017-05-17 | 上海嘉乐股份有限公司 | Method for improving moisture-absorption and sweating performance of fatty polyamide fiber/polyurethane fiber fabric |
| EP3896108A4 (en) * | 2018-12-11 | 2022-08-24 | Mitsui Chemicals, Inc. | Polyurethane dispersion and layered product |
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| CN1370189A (en) * | 2000-06-22 | 2002-09-18 | 浦项综合制铁株式会社 | Prepn. of aqueous urethane resin compsn. |
| CN1401686A (en) * | 2002-09-04 | 2003-03-12 | 清华大学 | Process for preparing quick response pH-sensitive polyurethane film |
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2006
- 2006-09-14 CN CNB2006100960410A patent/CN100497506C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1370189A (en) * | 2000-06-22 | 2002-09-18 | 浦项综合制铁株式会社 | Prepn. of aqueous urethane resin compsn. |
| CN1401686A (en) * | 2002-09-04 | 2003-03-12 | 清华大学 | Process for preparing quick response pH-sensitive polyurethane film |
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