CN104087149A - Method for preparing light-fast waterborne polyurethane coating material - Google Patents
Method for preparing light-fast waterborne polyurethane coating material Download PDFInfo
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Abstract
The invention discloses a method for preparing a light-fast waterborne polyurethane coating material. The method comprises the steps: mixing polytetrahydrofuran ether glycol and isophorone diisocyanate in the presence of a dibutyltin dilaurate catalyst, reacting for 1-4 hours at the temperature of 80-100 DEG C, adding liposome and coroxon, and reacting for 2 hours at the temperature of 90 DEG C, so as to obtain a polyurethane prepolymer A; adding a chain extender, 1,4-dioxane and riboflavin sodium phosphate into the prepolymer A, reacting for 1.5-3.5 hours at the temperature of 65-85 DEG C, adding a mixed solution A, reacting for 1-2 hours at the temperature of 75-85 DEG C, adding triethylamine to carry out neutralization reaction for 30-50 minutes, and adding water to emulsify, thereby obtaining the light-fast waterborne polyurethane coating material. The prepared light-fast polyurethane coating material is environment-friendly and cheap, is widely applied to the surfaces of walls, furniture and metallic utensils and serves as a binder of plastics, glass, paper making and textiles.
Description
technical fieldthe present invention relates to the preparation method of coating, particularly a kind of preparation method of photostabilization aqueous polyurethane coating.
Background technology
Urethane is mainly used in the aspects such as leather finish, textile printing and dyeing, paper-making industry, building coating, tackiness agent, be sprayed at coating and the paint on external and internal wall, furniture, hardware surface, all the time all directly or indirectly contacting with the mankind, poisonous, harmful coating is the moment health that threatening people also.Because the field using often contacts sunlight, owing to containing a large amount of UV-light harmful to coloured object in solar ray, approximately 290～460nm of its wavelength, these harmful UV-light, by redoxomorphism chemically, make the variation of coating generation color.
Urethane carries out polymerization and often adopts dibutyl tin laurate to make catalyzer, but because Heavy Metal, Sn works the mischief to environment along with the degraded of urethane, liposome is the self-assembly of lipid molecule (lipoid), it is a kind of structure by coated micro-water in the middle of one or more lipid bilayers, liposome can naturally exist, also can synthetic, its liposome, as a kind of carrier, has the feature of oneself.
Utilize liposome to dibutyl tin laurate, the tin of catalysis remnants to be fixed, reduce the harm of polyurethane coating resistates to environment.
The normal employing of urethane photostabilization adds UV light absorber and antioxidant to improve photostabilization, but traditional synthetized oxidation preventive agent has butylhydroxy anisole, t-butyl hydroperoxide, Tert. Butyl Hydroquinone etc., there is larger toxic side effect and carinogenicity, therefore need to find high-efficiency environment friendly, fast light technology.
summary of the invention
Technical problem to be solved by this invention is, a kind of photostabilization aqueous polyurethane coating preparation method is provided, select dibutyl tin laurate to make catalyzer, PTMG is reacted with isophorone diisocyanate, utilize liposome and coumaphos oxygen analog to be fixed dibutyl tin laurate, with photostabilization material as chainextender, 1, 4-dioxane replaces the synthetic solvent using of conventional urethane, with riboflavin sodium phosphate raising 1, the hydrophilic and oleophilic of 4-dioxane and dispersiveness, with the complex compound of rare earth to polyurethane-modified, make a kind of photostabilization aqueous polyurethane.
A preparation method for photostabilization aqueous polyurethane coating, is characterized in that:
(1) the aqueous nitric acid dissolved oxygen cerium 0.2g and the yttrium oxide 0.5g that are, 0.1mol/L by 5mL concentration, 40 DEG C of rising temperature, add Sunmorl N 60S 0.1g and cis-1,3,5-trimethyl cyclohexylamine-1,3,5-, tri-carboxylic acid 0.21g, adjusting mixing solutions pH is 4, reaction 1h, 50 DEG C add 2-(2 ˊ-hydroxyl-5 ˊ-aminomethyl phenyl) benzotriazole 0.5g, fully stirring reaction 2h, obtains mixed liquor A;
(2), under the condition existing at dibutyltin dilaurate catalyst, by PTMG with isophorone diisocyanate according to mixing 2.5:1 ~ 4.5: 1 mix, at 80 ~ 100 DEG C, react 1 ~ 4h, add liposome and coumaphos oxygen analog, reaction times 2h, 90 DEG C of temperature of reaction, obtain base polyurethane prepolymer for use as A, described catalyst levels is 0.2 ~ 0.5% of PTMG and isophorone diisocyanate gross weight, liposome consumption is PTMG, isophorone diisocyanate, 0.1 ~ 0.4% of dibutyl tin laurate gross weight, coumaphos oxygen analog is PTMG, isophorone diisocyanate, 0.2 ~ 0.5% of dibutyl tin laurate gross weight,
(3), add 1 of the chainextender of performed polymer weight 1.2 ~ 3.2% and performed polymer A weight 12 ~ 25% to performed polymer A, 4-dioxane and riboflavin sodium phosphate, under 65 ~ 85 DEG C of conditions, react 1.5 ~ 3.5h, add mixed liquor A, 75 ~ 85 DEG C of temperature of reaction, reaction times 1 ~ 2h, the triethylamine that is 10 ~ 15% by performed polymer weight carries out neutralization reaction 30 ~ 50min, add water and carry out emulsification 30min, obtain photostabilization aqueous polyurethane coating, riboflavin sodium phosphate and mixed liquor A are respectively 5 ~ 8% and 3 ~ 7% of performed polymer A weight;
The molecular weight of PTMG is 1000; Liposome is the one of sphingophospholipid, vincristine sulphate fat, dihydro sphingophospholipid, distearoyl phosphatidylcholine, polyxyethylated ammonium; Chainextender is any one in gallic acid, l-Epicatechol, lycium barbarum polysaccharide, myo-Inositol hexaphosphate, norepinephrine.
The present invention has following characteristics:
(1) liposome and coumaphos oxygen analog are fixed catalyzer, have reduced urethane due to the toxicity difficult problem that Heavy Metal, Sn causes, improve the levelling property of polyurethane film simultaneously;
(2) selecting fast light material is chainextender and rare-earth complex, has improved fast light efficiency, and the fast light material environment friendly of selecting;
(3) Isosorbide-5-Nitrae-dioxane replaces the synthetic solvent using of conventional urethane, improves hydrophilic and oleophilic and the dispersiveness of Isosorbide-5-Nitrae-dioxane with riboflavin sodium phosphate, and the solvent toxicity that urethane is used reduces greatly.
embodimentfurther illustrate the present invention below in conjunction with example.
example one
(1) the aqueous nitric acid dissolved oxygen cerium 1g and the yttrium oxide 2.5g that are, 0.1mol/L by 25mL concentration, 40 DEG C of rising temperature, add Sunmorl N 60S 0.5g and cis-1,3,5-trimethyl cyclohexylamine-1,3,5-, tri-carboxylic acid 1.05g, adjusting mixing solutions pH is 4, reaction 1h, 50 DEG C add 2-(2 ˊ-hydroxyl-5 ˊ-aminomethyl phenyl) benzotriazole 2.5g, fully stirring reaction 2h, obtains mixed liquor A;
(2), in the four-hole boiling flask of 500ml that stirring arm, thermometer, prolong are housed, PTMG 83.3g is mixed with isophorone diisocyanate 33.3g, under the condition existing at dibutyltin dilaurate catalyst 0.23g, at 80 DEG C, react 1h, add sphingophospholipid 0.12g and coumaphos oxygen analog 0.23g, reaction times 2h, 90 DEG C of temperature of reaction, obtain 116g base polyurethane prepolymer for use as A;
(3), in performed polymer A, add gallic acid 1.39g and 1,4-dioxane 13.9g and riboflavin sodium phosphate 5.8g, under 65 DEG C of conditions, react 1.5h, add mixed liquor A 3.48g, 75 DEG C of temperature of reaction, reaction times 1h, adds triethylamine 11.6g and carries out neutralization reaction 30min, the 120g that adds water carries out emulsification 30min, obtains photostabilization aqueous polyurethane coating.
Example two
(1) the aqueous nitric acid dissolved oxygen cerium 1g and the yttrium oxide 2.5g that are, 0.1mol/L by 25mL concentration, 40 DEG C of rising temperature, add Sunmorl N 60S 0.5g and cis-1,3,5-trimethyl cyclohexylamine-1,3,5-, tri-carboxylic acid 1.05g, adjusting mixing solutions pH is 4, reaction 1h, 50 DEG C add 2-(2 ˊ-hydroxyl-5 ˊ-aminomethyl phenyl) benzotriazole 2.5g, fully stirring reaction 2h, obtains mixed liquor A;
(2), in the four-hole boiling flask of 500ml that stirring arm, thermometer, prolong are housed, PTMG 75.2g is mixed with isophorone diisocyanate 16.7g, under the condition existing at dibutyltin dilaurate catalyst 0.46g, at 100 DEG C, react 4h, add vincristine sulphate fat 0.37g and coumaphos oxygen analog 0.46g, reaction times 2h, 90 DEG C of temperature of reaction, obtain 92g base polyurethane prepolymer for use as A;
(3), in performed polymer A, add l-Epicatechol 2.94g, 1,4-dioxane 23g and riboflavin sodium phosphate 7.4g, under 85 DEG C of conditions, react 3.5h, add mixed liquor A 6.4g, 85 DEG C of temperature of reaction, reaction times 2h, adds triethylamine 13.8g and carries out neutralization reaction 50min, the 110g that adds water carries out emulsification 30min, obtains photostabilization aqueous polyurethane coating.
example three
(1) the aqueous nitric acid dissolved oxygen cerium 1g and the yttrium oxide 2.5g that are, 0.1mol/L by 25mL concentration, 40 DEG C of rising temperature, add Sunmorl N 60S 0.5g and cis-1,3,5-trimethyl cyclohexylamine-1,3,5-, tri-carboxylic acid 1.05g, adjusting mixing solutions pH is 4, reaction 1h, 50 DEG C add 2-(2 ˊ-hydroxyl-5 ˊ-aminomethyl phenyl) benzotriazole 2.5g, fully stirring reaction 2h, obtains mixed liquor A;
(2), in the four-hole boiling flask of 500ml that stirring arm, thermometer, prolong are housed, PTMG 116.6g is mixed with isophorone diisocyanate 33.3g, under the condition existing at dibutyltin dilaurate catalyst 0.52g, at 90 DEG C, react 3.5h, add dihydro sphingophospholipid 0.38g and coumaphos oxygen analog 0.53g, reaction times 2h, 90 DEG C of temperature of reaction, obtain 150g base polyurethane prepolymer for use as A;
(3), in performed polymer A, add lycium barbarum polysaccharide 3.3g, 1,4-dioxane 27.8g and riboflavin sodium phosphate 9.8g, under 75 DEG C of conditions, react 2.5h, add mixed liquor A 7.5g, 80 DEG C of temperature of reaction, reaction times 1.5h, adds triethylamine 18.8g and carries out neutralization reaction 40min, the 120g that adds water carries out emulsification 30min, obtains photostabilization aqueous polyurethane coating.
example four
(1) the aqueous nitric acid dissolved oxygen cerium 1g and the yttrium oxide 2.5g that are, 0.1mol/L by 25mL concentration, 40 DEG C of rising temperature, add Sunmorl N 60S 0.5g, cis-1,3,5-trimethyl cyclohexylamine-1,3,5-, tri-carboxylic acid 1.05g and basic copper chloride 0.2g, adjusting mixing solutions pH is 4, reaction 1h, 50 DEG C add 2-(2 ˊ-hydroxyl-5 ˊ-aminomethyl phenyl) benzotriazole 2.5g, fully stirring reaction 2h, obtains mixed liquor A;
(2), in the four-hole boiling flask of 500ml that stirring arm, thermometer, prolong are housed, PTMG 83.3g is mixed with isophorone diisocyanate 33.3g, under the condition existing at dibutyltin dilaurate catalyst 0.23g, at 80 DEG C, react 1h, add distearoyl phosphatidylcholine 0.12g, coumaphos oxygen analog 0.23g and tetraphenylporphyrin iron 0.01g, reaction times 2h, 90 DEG C of temperature of reaction, obtain 116g base polyurethane prepolymer for use as A;
(3), in performed polymer A, add myo-Inositol hexaphosphate 1.39g, 1,4-dioxane 13.9g and riboflavin sodium phosphate 5.8g, under 65 DEG C of conditions, react 1.5h, add mixed liquor A 3.48g, 75 DEG C of temperature of reaction, reaction times 1h, adds triethylamine 11.6g and carries out neutralization reaction 30min, the 120g that adds water carries out emulsification 30min, obtains photostabilization aqueous polyurethane coating.
example five
(1) the aqueous nitric acid dissolved oxygen cerium 1g and the yttrium oxide 2.5g that are, 0.1mol/L by 25mL concentration, 40 DEG C of rising temperature, add Sunmorl N 60S 0.5g, cis-1,3,5-trimethyl cyclohexylamine-1,3,5-, tri-carboxylic acid 1.05g and ethyl hydrogenation cuproprotein 0.04g, adjusting mixing solutions pH is 4, reaction 1h, 50 DEG C add 2-(2 ˊ-hydroxyl-5 ˊ-aminomethyl phenyl) benzotriazole 2.5g, fully stirring reaction 2h, obtains mixed liquor A;
(2), in the four-hole boiling flask of 500ml that stirring arm, thermometer, prolong are housed, PTMG 75.2g is mixed with isophorone diisocyanate 16.7g, under the condition existing at dibutyltin dilaurate catalyst 0.46g, at 100 DEG C, react 4h, add polyxyethylated ammonium 0.37g, coumaphos oxygen analog 0.46g and ammonium chloride iron 0.1g, reaction times 2h, 90 DEG C of temperature of reaction, obtain 92g base polyurethane prepolymer for use as A;
(3), in performed polymer A, add norepinephrine 2.94g, 1,4-dioxane 23g and riboflavin sodium phosphate 7.4g, under 85 DEG C of conditions, react 3.5h, add mixed liquor A 6.4g, 85 DEG C of temperature of reaction, reaction times 2h, adds triethylamine 13.8g and carries out neutralization reaction 50min, the 110g that adds water carries out emulsification 30min, obtains photostabilization aqueous polyurethane coating.
Further illustrate beneficial effect of the present invention below by related experiment data:
For quantitative description resistance to light of coating energy, adopt spectrophotometer to detect, to obtain inverse difference △ E, the photostabilization of coating and finish paint is described.△ E has represented 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 [J] of several organic historical relic's protection polymer coatings. Northwest University's journal, 2005,35 (5): 56 ~ 58).
Table one photostabilization aqueous polyurethane institute film forming photostabilization
| Time/min | Example one | Example two | Example three | Example four | Example five |
| 90 | 0.2 | 0.3 | 0.4 | 0.1 | 0.1 |
| 150 | 0.6 | 0.4 | 0.4 | 0.1 | 0.2 |
| 270 | 0.9 | 0.5 | 0.6 | 0.2 | 0.2 |
| 330 | 0.9 | 0.7 | 0.6 | 0.4 | 0.2 |
| 390 | 1.1 | 0.9 | 0.8 | 0.5 | 0.3 |
| 450 | 1.1 | 0.9 | 0.8 | 0.6 | 0.3 |
| 510 | 1.1 | 1.2 | 0.9 | 0.7 | 0.7 |
| 540 | 11 | 1.2 | 1.0 | 0.9 | 0.8 |
| 600 | 1.1 | 1.2 | 1.2 | 1.1 | 0.8 |
Can find from table one, example one all in slight variation range, shows good photostabilization to the prepared coating photostabilization of example five.
The sunproof mechanical property of table two photostabilization aqueous polyurethane institute's film forming
| Experimental group | Example one | Example two | Example three | Example four | Example five |
| Elongation at break (%) | 160 | 145 | 155 | 166 | 168 |
| Tensile strength (MPa) | 5.7 | 5.6 | 5.8 | 5.9 | 5.9 |
| Abrasion resisting (level) | 3.5 | 4 | 4 | 4 | 4 |
The reference of table two middle finger object detection method (Jiang Weiqi. leather finished product physical and chemical inspection [M]. China Light Industry Press, 1999), coating gained film elongation at break of the present invention, tensile strength, wear-resistant all performances are better.
Claims (4)
1. a preparation method for photostabilization aqueous polyurethane coating, is characterized in that:
(1) the aqueous nitric acid dissolved oxygen cerium 1g and the yttrium oxide 2.5g that are, 0.1mol/L by 25mL concentration, 40 DEG C of rising temperature, add Sunmorl N 60S 0.5g and cis-1,3,5-trimethyl cyclohexylamine-1,3,5-, tri-carboxylic acid 1.05g, adjusting mixing solutions pH is 4, reaction 1h, 50 DEG C add 2-(2 ˊ-hydroxyl-5 ˊ-aminomethyl phenyl) benzotriazole 2.5g, fully stirring reaction 2h, obtains mixed liquor A;
(2), under the condition existing at dibutyltin dilaurate catalyst, PTMG is mixed by weight 2.5:1 ~ 4.5:1 with isophorone diisocyanate, at 80 ~ 100 DEG C, react 1 ~ 4h, add liposome and coumaphos oxygen analog, reaction times 2h, 90 DEG C of temperature of reaction, obtain base polyurethane prepolymer for use as A, described catalyst levels is 0.2 ~ 0.5% of PTMG and isophorone diisocyanate gross weight, liposome consumption is PTMG, isophorone diisocyanate, 0.1 ~ 0.4% of dibutyl tin laurate gross weight, coumaphos oxygen analog is PTMG, isophorone diisocyanate, 0.2 ~ 0.5% of dibutyl tin laurate gross weight,
(3), add 1 of the chainextender of performed polymer weight 1.2 ~ 3.2% and performed polymer A weight 12 ~ 25% to performed polymer A, 4-dioxane and riboflavin sodium phosphate, under 65 ~ 85 DEG C of conditions, react 1.5 ~ 3.5h, add mixed liquor A, 75 ~ 85 DEG C of temperature of reaction, reaction times 1 ~ 2h, the triethylamine that is 10 ~ 15% by performed polymer A weight carries out neutralization reaction 30 ~ 50min, add emulsifying water 30min, obtain photostabilization aqueous polyurethane coating, riboflavin sodium phosphate and mixed liquor A are respectively 5 ~ 8% and 3 ~ 7% of performed polymer A weight.
2. the preparation method of a kind of photostabilization aqueous polyurethane coating as claimed in claim 1, is characterized in that: the molecular weight of PTMG is 1000.
3. the preparation method of a kind of photostabilization aqueous polyurethane coating as claimed in claim 1, is characterized in that: liposome is the one of sphingophospholipid, vincristine sulphate fat, dihydro sphingophospholipid, distearoyl phosphatidylcholine, polyxyethylated ammonium.
4. the preparation method of a kind of photostabilization aqueous polyurethane coating as claimed in claim 1, is characterized in that: chainextender is any one in gallic acid, l-Epicatechol, lycium barbarum polysaccharide, myo-Inositol hexaphosphate, norepinephrine.
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| CN105176368A (en) * | 2015-10-26 | 2015-12-23 | 烟台大学 | Preparation method of polyurethane coating and adhesive with flame retardance and light resistance |
| CN106497385A (en) * | 2016-11-23 | 2017-03-15 | 四川大学 | A kind of preparation method of visible ray selfreparing aqueous polyurethane coating material of the main chain containing double selenium keys |
| CN109486401A (en) * | 2018-10-23 | 2019-03-19 | 上饶市天佳新型材料有限公司 | A kind of aqueous polyurethane water-repellent paint and preparation method thereof |
| CN109554096A (en) * | 2018-12-02 | 2019-04-02 | 段瑶瑶 | A kind of preparation method of light-resistant waterborne polyurethane coating |
| CN109705719A (en) * | 2018-11-29 | 2019-05-03 | 安徽开林新材料股份有限公司 | A kind of extinguishing waterborn polyurethane coating |
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| CN105176368B (en) * | 2015-10-26 | 2017-06-23 | 烟台大学 | A kind of preparation method of fire-retardant and sunproof polyurethane coating and adhesive |
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| CN106497385B (en) * | 2016-11-23 | 2018-09-14 | 四川大学 | A kind of preparation method of visible light selfreparing aqueous polyurethane coating material of the main chain containing double selenium keys |
| CN109486401A (en) * | 2018-10-23 | 2019-03-19 | 上饶市天佳新型材料有限公司 | A kind of aqueous polyurethane water-repellent paint and preparation method thereof |
| CN109705719A (en) * | 2018-11-29 | 2019-05-03 | 安徽开林新材料股份有限公司 | A kind of extinguishing waterborn polyurethane coating |
| CN109554096A (en) * | 2018-12-02 | 2019-04-02 | 段瑶瑶 | A kind of preparation method of light-resistant waterborne polyurethane coating |
| CN114921971A (en) * | 2022-04-14 | 2022-08-19 | 浙江彩蝶实业股份有限公司 | Production process of polyester curtain fabric based on biomass anti-ultraviolet coating |
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Effective date of registration: 20160802 Address after: Jiang Gao Zhen Xin Lou Cun, Baiyun District of Guangzhou City, Guangdong province 510000 Patentee after: CSE (Guangzhou) Co., Ltd. Address before: 264005 Shandong Province, Yantai city Laishan District Road No. 30 spring Patentee before: Duan Baorong |