CN103436155A - Preparation method of light-resistant water-based polyurethane coating - Google Patents
Preparation method of light-resistant water-based polyurethane coating Download PDFInfo
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- CN103436155A CN103436155A CN2013104078354A CN201310407835A CN103436155A CN 103436155 A CN103436155 A CN 103436155A CN 2013104078354 A CN2013104078354 A CN 2013104078354A CN 201310407835 A CN201310407835 A CN 201310407835A CN 103436155 A CN103436155 A CN 103436155A
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- photostabilization
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- polyurethane coating
- stirring reaction
- aqueous polyurethane
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- 239000011527 polyurethane coating Substances 0.000 title claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 11
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000004970 Chain extender Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims abstract description 7
- 239000012975 dibutyltin dilaurate Substances 0.000 claims abstract description 7
- 238000004945 emulsification Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 230000000176 photostabilization Effects 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- -1 isocyanic acid tri-methyl hexamethylene esters Chemical class 0.000 claims description 4
- KJTLQQUUPVSXIM-ZCFIWIBFSA-N (R)-mevalonic acid Chemical group OCC[C@](O)(C)CC(O)=O KJTLQQUUPVSXIM-ZCFIWIBFSA-N 0.000 claims description 3
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 3
- KJTLQQUUPVSXIM-UHFFFAOYSA-N DL-mevalonic acid Natural products OCCC(O)(C)CC(O)=O KJTLQQUUPVSXIM-UHFFFAOYSA-N 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007998 bicine buffer Substances 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 abstract description 11
- 229920002635 polyurethane Polymers 0.000 abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000005442 diisocyanate group Chemical group 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 11
- 238000009835 boiling Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229920006264 polyurethane film Polymers 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002086 nanomaterial Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a preparation method of a light-resistant water-based polyurethane coating. The preparation method comprises the following steps of: mixing bisphenol S and diisocyanate in the presence of a dibutyltin dilaurate catalyst, and stirring to react at 60-85 DEG C for 1.5-3.5 hours to obtain a polyurethane prepolymer A; adding a hydrophilic chain extender with carboxyl content accounting for 1.2%-4.6% of the weight of A into A, then adding a solvent which accounts for 15%-35% of the weight of A, and stirring to react under the condition of 80-95 DEG C for 1.0-4.0 hours; adding triethylamine according to the condition that the mole ratio of COOH/NH2 is 0.6:(1-1.6):1 for neutralization, stirring to react for 30-70 minutes, and adding water for emulsification to form the light-resistant water-based polyurethane coating. The prepared light-resistant water-based polyurethane is environmentally-friendly and low in cost and can meet the requirement of the market on the property of light-resistant polyurethane.
Description
Technical field
The present invention relates to a kind of preparation method of aqueous polyurethane, particularly a kind of preparation method of photostabilization aqueous polyurethane coating.
Background technology
Aqueous polyurethane be take water as dispersion medium, nonpoisonous and tasteless, free from environmental pollution, is widely used in woodwork coating, automobile repairing paint, protective system, building coating, floor paint, electronic paint, speciality coating, polyurethane water-proof paint etc.But because the use field often contacts sunlight, contain a large amount of UV-light harmful to light object in solar ray, its wavelength 290 ~ 460nm, these UV-light, by redoxomorphism chemically, make material surface generation colour-change, affect appearance.
At present sunproof polyurethane has two kinds of preparation methods, and one carries out pre-polymerization with polycarbonate diol instead of polyesters dibasic alcohol or polyether Glycols and isocyanic ester, and the synthetic urethane of this mode has photostabilization preferably, but the polyurethane film of synthesized is too hard; Another kind of mode is that urethane and nano material is as composite as nano titanium oxide, nano zine oxide, carbon nanotube etc., the photostabilization of raising urethane, but due to the less stable of nano material emulsion, and the standby urethane stability in storage of this legal system is poor.
Summary of the invention
The present invention has adopted following technical scheme.
(1), under the condition that exists at dibutyltin dilaurate catalyst, by the mol ratio of NCO/OH, be 1.2:1 ~ 3.5:1, bisphenol S is mixed with vulcabond, in 60 ~ 85 ℃ of lower stirring reaction 1.5 ~ 3.5h, obtain base polyurethane prepolymer for use as A; Described catalyst levels is 0.3 ~ 0.6% of bisphenol S and vulcabond gross weight;
(2), in A, add the hydrophilic chain extender that carboxyl-content is A weight 1.2 ~ 4.6%, the stirring reaction time is 40 ~ 80min, adds the solvent of A weight 15 ~ 35%, and stirring reaction 1.0 ~ 4.0h under 80 ~ 95 ℃ of conditions, press COOH/NH
2mol ratio be 0.6:1 ~ 1.6:1, add triethylamine to be neutralized, stirring reaction 30 ~ 70min, add water and carry out emulsification, forms a kind of photostabilization aqueous polyurethane coating B;
Vulcabond be in hexamethylene diisocyanate, isophorone diisocyanate, two isocyanic acid tri-methyl hexamethylene esters, lysinediisocyanate any one; Hydrophilic chain extender is mevalonic acid, 2,3 dihydroxybutanedioic acid, N, N-bicine N-, 2, any one in 2-dimethylolpropionic acid, 3-hydroxyl-2-(methylol)-2 Methylpropionic acid; Solvent is any one in dimethyl sulfoxide (DMSO), methylethylketone, pyridine.
The present invention has following characteristics:
(1), prepared photostabilization aqueous polyurethane and material compatibility are good;
(2) vulcabond of, selecting has good photostabilization;
(3), adopt bisphenol S to replace traditional polyester diol or polyether Glycols, prepared urethane photostabilization is good, institute's film forming is neither too hard, nor too soft, solvent resistance and wear resistance significantly improve;
(4), dimethyl sulfoxide (DMSO), methylethylketone, pyridine replace the synthetic DMF solvent used of traditional urethane, reduced the toxicity of urethane.
embodimentfurther illustrate the present invention below in conjunction with example.
example one
(1), in the four-hole boiling flask of the 500ml that stirring arm, thermometer, prolong are housed, bisphenol S 25g is mixed with hexamethylene diisocyanate 20.2g, under the condition existed at dibutyltin dilaurate catalyst 0.14g, in 60 ℃ of lower stirring reaction 1.5h, obtain 45.1g base polyurethane prepolymer for use as A;
(2), in base polyurethane prepolymer for use as, add hydrophilic chain extender mevalonic acid 1.64g, the stirring reaction time is 40min, add dimethyl sulfoxide (DMSO) 6.8g in A, stirring reaction 1.0h under 80 ℃ of conditions, add triethylamine 2.0g to be neutralized, stirring reaction 30min, add water 150g and carry out emulsification, forms a kind of photostabilization aqueous polyurethane coating B;
example two
(1), in the four-hole boiling flask of the 500ml that stirring arm, thermometer, prolong are housed, bisphenol S 25g is mixed with isophorone diisocyanate 77.7g, under the condition existed at dibutyltin dilaurate catalyst 0.62g, in 85 ℃ of lower stirring reaction 3.5h, obtain 102.5g base polyurethane prepolymer for use as A;
(2), in base polyurethane prepolymer for use as, add hydrophilic chain extender 2,3-dyhydrobutanedioic acid 7.9g, the stirring reaction time is 80min, add methylethylketone 35.9g in A, stirring reaction 4.0h under 95 ℃ of conditions, add triethylamine 6.6g to be neutralized, stirring reaction 70min, add water 160g and carry out emulsification, form a kind of photostabilization aqueous polyurethane coating B;
example three
(1), in the four-hole boiling flask of the 500ml that stirring arm, thermometer, prolong are housed, bisphenol S 25g is mixed with two isocyanic acid tri-methyl hexamethylene ester 50.4g, under the condition existed at dibutyltin dilaurate catalyst 0.34g, in 75 ℃ of lower stirring reaction 2.5h, obtain 75.1g base polyurethane prepolymer for use as A;
(2), in base polyurethane prepolymer for use as, add hydrophilic chain extender N, N-bicine N-7.9g, the stirring reaction time is 60min, add pyridine 18.8g in A, stirring reaction 2.5h under 90 ℃ of conditions, add triethylamine 4.5g to be neutralized, stirring reaction 50min, add water 170g and carry out emulsification, form a kind of photostabilization aqueous polyurethane coating B;
example four
(1), in the four-hole boiling flask of the 500ml that stirring arm, thermometer, prolong are housed, bisphenol S 25g is mixed with lysinediisocyanate 54.2g, under the condition existed at dibutyltin dilaurate catalyst 0.35g, in 75 ℃ of lower stirring reaction 2.5h, obtain 78.1g base polyurethane prepolymer for use as A;
(2), in base polyurethane prepolymer for use as, add hydrophilic chain extender 3-hydroxyl-2-(methylol)-2 Methylpropionic acid 5g, the stirring reaction time is 60min, add pyridine 15.6g in A, stirring reaction 2.5h under 90 ℃ of conditions, add triethylamine 4.9g to be neutralized, stirring reaction 50min, add water 170g and carry out emulsification, forms a kind of photostabilization aqueous polyurethane coating B;
For the light fastness of quantitative description urethane, adopt spectrophotometer to be detected, to obtain inverse difference △ E, the photostabilization of urethane is described.△ E has represented the colour-change degree, and △ E is larger, and color change is more obvious.In general, △ E value is the slight variation of 0～1.5 genus; △ E value is that 1.5～3.0 genus can be felt variation; △ E value be 3.0～6.0 belong to considerable changes (referring to Wang Fang, party's climax, Wang Liqin, the photodegradation of several organic historical relic's protection polymer coatings [J]. Northwest University's journal, 2005,35 (5): 56 ~ 58).The mechanical property of polyurethane film adopts elongation at break to weigh, and elongation at break is larger, and its mechanical property is better.The testing method of elongation at break see (Jiang Weiqi. leather finished product physical and chemical inspection [M]. China Light Industry Press, 1999,82 ~ 96).Example one is designated as respectively to D, F, G, H to the sunproof polyurethane of example four gained, selects the sunproof polyurethane PODESENG 513MS on market to be contrasted with it.
The value of chromatism △ E of the different UV-irradiation of table one urethane under the time changes
| Time/min | PODESENG? 513MS | D | F | G | H |
| 90 | 0.7 | 0.3 | 0.4 | 0.2 | 0.1 |
| 150 | 0.9 | 0.4 | 0.6 | 0.2 | 0.1 |
| 270 | 1.0 | 0.5 | 0.7 | 0.3 | 0.3 |
| 330 | 1.1 | 0.5 | 0.7 | 0.4 | 0.4 |
| 390 | 1.3 | 0.7 | 0.8 | 0.5 | 0.6 |
| 450 | 1.5 | 0.8 | 0.8 | 0.6 | 0.7 |
| 510 | 1.8 | 0.9 | 0.9 | 0.7 | 0.9 |
| 540 | 2.1 | 1.0 | 1.1 | 0.7 | 0.9 |
| 600 | 2.3 | 1.1 | 1.1 | 1.0 | 1.0 |
From table one, can find, example one four kind urethane photostabilization prepared to example four all, in slight variation range, show good photostabilization, and the sunproof polyurethane on market have belonged to and can feel variation more than 510min.
Table two photostabilization aqueous polyurethane film elongation at break
| Classification | PODESENG 513MS | D | F | G | H |
| Elongation at break/% | 188.26 | 227.67 | 222.52 | 221.80 | 223.54 |
In table two, the sunproof polyurethane film elongation at break of example one to four gained is larger than the elongation at break of the sunproof polyurethane in market.
Claims (4)
1. the preparation method of a photostabilization aqueous polyurethane coating is characterized in that:
(1), under the condition that exists at dibutyltin dilaurate catalyst, by the mol ratio of NCO/OH, be 1.2:1 ~ 3.5:1, bisphenol S is mixed with vulcabond, in 60 ~ 85 ℃ of lower stirring reaction 1.5 ~ 3.5h, obtain base polyurethane prepolymer for use as A; Described catalyst levels is 0.3 ~ 0.6% of bisphenol S and vulcabond gross weight;
(2), in A, add the hydrophilic chain extender that carboxyl-content is A weight 1.2 ~ 4.6%, the stirring reaction time is 40 ~ 80min, adds the solvent of A weight 15 ~ 35%, and stirring reaction 1.0 ~ 4.0h under 80 ~ 95 ℃ of conditions, press COOH/NH
2mol ratio be 0.6:1 ~ 1.6:1, add triethylamine to be neutralized, stirring reaction 30 ~ 70min, add water and carry out emulsification, forms a kind of photostabilization aqueous polyurethane coating B.
2. the preparation method of a kind of photostabilization aqueous polyurethane coating as claimed in claim 1 is characterized in that: vulcabond be in hexamethylene diisocyanate, isophorone diisocyanate, two isocyanic acid tri-methyl hexamethylene esters, lysinediisocyanate any one.
3. the preparation method of a kind of photostabilization aqueous polyurethane coating as claimed in claim 1, it is characterized in that: hydrophilic chain extender is mevalonic acid, 2,3-dyhydrobutanedioic acid, N, N-bicine N-, 2, any one in 2-dimethylolpropionic acid, 3-hydroxyl-2-(methylol)-2 Methylpropionic acid.
4. the preparation method of a kind of photostabilization aqueous polyurethane coating as claimed in claim 1, it is characterized in that: solvent is any one in dimethyl sulfoxide (DMSO), methylethylketone, pyridine.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104004449A (en) * | 2014-06-15 | 2014-08-27 | 段宝荣 | Method for preparing light-resistant and flame-resistant aqueous polyurethane coatings |
| CN104073145A (en) * | 2014-07-21 | 2014-10-01 | 段小宁 | Preparation method for lightproof and waterproof polyurethane coating |
| CN104087149A (en) * | 2014-07-21 | 2014-10-08 | 段宝荣 | Method for preparing light-fast waterborne polyurethane coating material |
| CN104098995A (en) * | 2014-07-21 | 2014-10-15 | 朱蕾 | Preparation method for flame-retardant waterproof aqueous polyurethane paint |
| CN104356330B (en) * | 2014-09-28 | 2017-02-08 | 陕西科技大学 | Carboxylic acid waterborne polyurethane chain extender and preparation method thereof |
| CN107428906A (en) * | 2015-03-06 | 2017-12-01 | H.B.富乐公司 | Water based primer compositions |
| CN109354681A (en) * | 2018-11-19 | 2019-02-19 | 中国科学院青岛生物能源与过程研究所 | A kind of preparation method of non-isocyanate polyurethane |
| CN111662633A (en) * | 2020-06-24 | 2020-09-15 | 广东达尔新型材料有限公司 | Anti-static wear-resistant polyurethane floor coating and preparation method thereof |
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Cited By (13)
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| CN104004449B (en) * | 2014-06-15 | 2016-04-20 | 段宝荣 | A kind of fast light preparation method with aqueous flame retardant polyurethane coating |
| CN104004449A (en) * | 2014-06-15 | 2014-08-27 | 段宝荣 | Method for preparing light-resistant and flame-resistant aqueous polyurethane coatings |
| CN104073145B (en) * | 2014-07-21 | 2016-08-24 | 常州市天安特种涂料有限公司 | A kind of preparation method of light-resistant waterborne polyurethane coating |
| CN104098995A (en) * | 2014-07-21 | 2014-10-15 | 朱蕾 | Preparation method for flame-retardant waterproof aqueous polyurethane paint |
| CN104087149A (en) * | 2014-07-21 | 2014-10-08 | 段宝荣 | Method for preparing light-fast waterborne polyurethane coating material |
| CN104098995B (en) * | 2014-07-21 | 2016-05-04 | 广州市盛邦康体场地材料有限公司 | A kind of preparation method of fire-retardant and water proofing property aqueous polyurethane coating |
| CN104073145A (en) * | 2014-07-21 | 2014-10-01 | 段小宁 | Preparation method for lightproof and waterproof polyurethane coating |
| CN104356330B (en) * | 2014-09-28 | 2017-02-08 | 陕西科技大学 | Carboxylic acid waterborne polyurethane chain extender and preparation method thereof |
| CN107428906A (en) * | 2015-03-06 | 2017-12-01 | H.B.富乐公司 | Water based primer compositions |
| CN107428906B (en) * | 2015-03-06 | 2021-02-02 | H.B.富乐公司 | Water-based primer composition |
| CN109354681A (en) * | 2018-11-19 | 2019-02-19 | 中国科学院青岛生物能源与过程研究所 | A kind of preparation method of non-isocyanate polyurethane |
| CN111662633A (en) * | 2020-06-24 | 2020-09-15 | 广东达尔新型材料有限公司 | Anti-static wear-resistant polyurethane floor coating and preparation method thereof |
| CN111662633B (en) * | 2020-06-24 | 2021-11-30 | 广东达尔新型材料有限公司 | Anti-static wear-resistant polyurethane floor coating and preparation method thereof |
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