CN111269380A - Photocuring arabinose-based polyurethane acrylate and preparation method thereof - Google Patents
Photocuring arabinose-based polyurethane acrylate and preparation method thereof Download PDFInfo
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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Abstract
The invention discloses a photocuring arabinose-based polyurethane acrylate and a preparation method thereof, wherein the preparation step of the polyurethane acrylate comprises the steps of biological low-carbon glycol chain extension diisocyanate, semi-end capping of a photosensitive hydroxyl monomer, arabinose end capping and optical activity monomer viscosity regulation, and finally mixing the obtained resin with a photoinitiator and photocuring to obtain a biological polyurethane coating. The prepared arabinosyl polyurethane acrylate takes arabinose and biological low-carbon glycol as main raw materials, the synthetic process is green and environment-friendly, and the comprehensive performance of the photocuring coating is excellent.
Description
Technical Field
The invention relates to the technical field of photocuring materials, in particular to a method for preparing multifunctional polyurethane acrylate by taking arabinose from a biological source as a central raw material.
Background
The polyurethane acrylate is a very important photocuring oligomer, raw materials used for synthesis have various selectable structures, target products with various properties can be prepared through molecular structure design, the oligomer is the oligomer with the most product types in the field of photocuring raw materials, and the oligomer is applied to various industries such as coatings, printing ink, adhesives and the like to provide lasting protection, decoration and functionality. The urethane acrylate molecules have urethane bonds, and can form various hydrogen bonds among high molecular chains, so that the cured film has excellent wear resistance and flexibility, higher elongation at break, good chemical resistance and high and low temperature resistance, and better comprehensive performance, and mainly comprises three types of aromatic, aliphatic and alicyclic. Aromatic compounds have rigid benzene rings, are good in mechanical strength, hardness and heat resistance, but poor in flexibility and easy to yellow. The main chain of aliphatic and alicyclic is saturated alkane and cyclane, and has good weatherability and flexibility, but low strength and high price. In addition, commercial urethane acrylates are produced mainly using petrochemical raw materials, and are highly dependent on petroleum resources. Under the current global development, the prepared polyurethane acrylate with excellent performance and environmental friendliness has obvious scientific significance and practical significance.
Arabinose, also called as pectin sugar, is a levorotatory monosaccharide obtained by carrying out complex separation and purification on colloid secreted by Arabic trees by utilizing biological, physical and chemical methods. Natural arabinose rarely occurs in a free state, usually in combination with other monosaccharides, in the form of heteropolysaccharides. Has the characteristics of wide distribution and multiple sources, and the corn husks, corn cob cores, rice, wheat and other cereals and the hemicellulose and the pectin of the plant cell walls of beet, apple and other plants have higher content. In recent years, arabinose-related industries are rapidly developed, and main application fields are medicines, health-care foods, essences and flavors, bioengineering, biological tests, chemical reagents, new material synthesis and the like. In the molecular structure, four hydroxyl functional groups provide a large number of active sites which can participate in the reaction, and the six-membered heterocyclic ring structure simultaneously takes into account the flexibility and the strength, so that the arabinose has strong attraction in the field of preparation of novel bio-based photocuring materials.
The Chinese patent with application number of 201610457541.6 discloses a preparation method of bio-based photo-curing polyurethane, which comprises the steps of reacting bio-based monomer isosorbide with diisocyanate to prepare NCO-terminated monomer, reacting the NCO-terminated monomer with dihydroxy acid to synthesize polyurethane prepolymer, and then terminating the polyurethane prepolymer with acrylate monohydric alcohol to prepare the isosorbide-based photo-curing polyurethane which can be used for preparing a photoresist composition with excellent comprehensive performance.
The Chinese patent with application number 201711370211.4 discloses a preparation method of bio-based material modified UV-cured waterborne polyurethane, wherein the polyester waterborne polyurethane is subjected to end modification by sugar compounds such as sucrose, fructose, maltose and the like, and the obtained product has excellent adhesive force, hardness and hydrophilicity.
In the two patent applications, the novel-structure photo-curing polyurethane is prepared based on alcohol or sugar of biological origin, but so far, no research report about preparing photo-curing polyurethane acrylate by taking arabinose as a central raw material is found.
Disclosure of Invention
Based on the above background, the applicant of the present invention provides a photocuring arabinosyl polyurethane acrylate and a preparation method thereof. According to the invention, the biomass raw material arabinose is taken as a structural center raw material, the preparation process is safe and environment-friendly, and the development concept of green chemistry is compounded; the introduced hexabasic heterocyclic structure endows the condensate with excellent strength and flexibility, and the introduced multiple photosensitive groups realize the photocuring effect with high efficiency and high quality.
The technical scheme of the invention is as follows:
a preparation method of the photocuring arabinose-based polyurethane acrylate resin comprises the following steps:
(1) chain extension: putting biological low-carbon glycol, a catalyst and an antioxidant into a reaction vessel, stirring to form a homogeneous solution, and introducing N through a guide pipe2Slowly adding diisocyanate through a dropping device, and stirring and reacting for 4-6h at 45-55 ℃;
(2) half end capping: slowly adding solvent and polymerization inhibitor into the product obtained in the step (1), heating to 65-75 ℃, stirring, and adding N2Dripping a photosensitive hydroxyl monomer under the condition, and reacting for 5-8h under the condition of heat preservation;
(3) end capping: adding arabinose into the product in the step (2) in batches, heating to 90-100 ℃, stirring, and adding N2Keeping the temperature and reacting for 10 hours under the condition;
(4) and (3) viscosity adjustment: and after the reaction is finished, removing the solvent by reduced pressure evaporation, and finally adding an active diluent to adjust the viscosity of the system to obtain the photocuring arabinose-based polyurethane acrylate resin.
The biological method low-carbon diol is one or more of 1, 3-propylene glycol, 1, 4-butanediol and 2-methyl-1, 4-butanediol.
The catalyst is one or more of dioctyltin dilaurate, organic bismuth and N-methylmorpholine, and the dosage of the catalyst is 0.5-1% of the total mass of the dihydric alcohol and the diisocyanate.
The antioxidant is one or more of 2, 6-di-tert-butyl-p-cresol, thiodipropionic acid diester and dihydroquinoline, and the dosage of the antioxidant is 0.3-0.5% of the total mass of the dihydric alcohol and the diisocyanate.
The diisocyanate is one or more of isophorone diisocyanate, toluene diisocyanate, hexamethylene diisocyanate and dicyclohexylmethane diisocyanate.
The solvent is one or more of toluene, isooctane and methyl isobutyl ketone, and the dosage of the solvent is 0.3 to 0.5 time of the total mass of the dihydric alcohol, the diisocyanate and the photosensitive hydroxyl monomer.
The polymerization inhibitor is one or more of p-hydroxyanisole, hydroquinone and phenothiazine, and the dosage of the polymerization inhibitor is 0.3-0.5% of the total mass of the dihydric alcohol, the diisocyanate and the photosensitive hydroxyl monomer.
The photosensitive hydroxyl monomer is one or more of hydroxyethyl acrylate, 2-hydroxyethyl methacrylate and hydroxypropyl acrylate.
The active diluent is one or more of tetrahydrofuran acrylate, tripropylene glycol diacrylate, 1, 6-hexanediol diacrylate and dipropylene glycol diacrylate, and the dosage of the active diluent is 0.2-0.4 times of the total mass of the dihydric alcohol, the diisocyanate, the photosensitive hydroxyl monomer and the arabinose.
The molar ratio of the biological low-carbon diol to the diisocyanate to the photosensitive hydroxyl monomer to the arabinose is 1:2:1: 0.25.
The arabinose-based polyurethane acrylate can be used as main resin, is used for preparing a bio-based photocuring coating under the action of a free radical type photoinitiator 2-hydroxy-2-methyl-1-phenyl-1-acetone, and has the comprehensive properties of good hardness, flexibility and weather resistance.
The beneficial technical effects of the invention are as follows:
the light-cured polyurethane acrylate is prepared by the steps of low-carbon glycol chain extension diisocyanate compound, photosensitive hydroxyl monomer half-terminated end, arabinose hydroxyl addition terminated end, vacuum pumping concentration, reactive diluent viscosity adjustment and the like. Compared with the traditional petroleum-based polyurethane acrylate, the raw material selection, the preparation process and the subsequent curing technology involved in the invention have obvious advantages of green and sustainability: 1. and (4) selecting raw materials. The arabinose is used as a skeleton raw material, has wide source, effectively reduces the consumption and dependence on petroleum resources, and has the characteristics of environmental friendliness and sustainable development; the low-carbon diol is used as a chain extension raw material and is produced by a biological method, the production conditions are mild and safe, the toxicity is low, and the new economic development requirement of environmental protection is met. 2. A preparation process. The chemical reaction involved in the invention is mainly the addition between hydroxyl and isocyanate, the synthesis technology is mature and reliable, and the operability is strong; the feeding proportion of various raw materials is strictly controlled, and the feed is non-toxic and harmless and has no obvious discharge of three wastes. 3. And (5) subsequent curing. The photo-curing technology is adopted, so that the efficiency is high, the condition is mild, and the energy is saved and the environment is protected. The multifunctional photosensitive group in the molecular structure of the arabinosyl polyurethane acrylate provides high photocuring reaction activity and high crosslinking network density, and the six-membered heterocycle enables a cured product to have excellent hardness, flexibility and weather resistance.
Drawings
FIG. 1 is a schematic diagram showing the reaction mechanism of example 1 of the present invention;
FIG. 2 is a NMR chart of arabinosyl polyurethane acrylate obtained in example 1 of the present invention;
FIG. 3 is the NMR spectrum of the arabinose-based polyurethane acrylate obtained in example 1 of the present invention;
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and examples; the raw materials are calculated according to parts by weight.
Example 1
The preparation method of the photocuring arabinose-based polyurethane acrylate comprises the following steps:
(1) chain extension: 30.048g of 1, 4-butanediol, 1.068g of dioctyltin dilaurate and 0.64g of 2, 6-di-tert-butyl-p-cresol were placed in a 500mL four-necked flask equipped with a mechanical stirrer, a thermometer, a reflux condenser and a gas conduit, and stirred to form a homogeneous solution, N was introduced into the homogeneous solution2177.832g of isophorone diisocyanate is dripped into the mixture through a constant pressure dropping funnel, and the mixture is stirred and reacts for 6 hours at 50 ℃;
(2) half end capping: adding 78.08g of toluene and 0.78g of p-hydroxyanisole slowly into the product obtained in the step (1), heating to 70 ℃, stirring, and adding N246.448g of hydroxyethyl acrylate is dripped under the condition, and the reaction is carried out for 8 hours under the condition of heat preservation;
(3) end capping: 15.012g of arabinose are added into the product in the step (2) in batches, the temperature is raised to 100 ℃, and the mixture is stirred and N2Keeping the temperature and reacting for 10 hours under the condition;
(4) and (3) viscosity adjustment: after the reaction is finished, removing toluene by reduced pressure evaporation, and finally adding 55.068g of tetrahydrofuran acrylate to adjust the viscosity of the system to obtain the photocuring arabinose-based polyurethane acrylate.
Example 2
The preparation method of the photocuring arabinose-based polyurethane acrylate comprises the following steps:
(1) chain extension: 30.44g of 1, 3-propanediol, 1.02g of organic bismuth and 0.596g of thiodipropionic acid diester were put into a 500mL four-necked flask equipped with a mechanical stirrer, a thermometer, a reflux condenser and a gas conduit, and stirred to form a homogeneous solution, and N was introduced into the homogeneous solution2139.32g of toluene diisocyanate is added dropwise through a constant pressure dropping funnel, and the mixture is stirred and reacted for 4 hours at the temperature of 45 ℃;
(2) half end capping: 77.636g of isooctane and 0.776g of hydroquinone are slowly added into the product in the step (1), the temperature is raised to 65 ℃, stirring is carried out, and N252.06g of 2-hydroxyethyl methacrylate is dripped under the condition, and the reaction is carried out for 7 hours under the condition of heat preservation;
(3) end capping: 15.012g of arabinose are added into the product in the step (2) in batches, the temperature is raised to 90 ℃, and the mixture is stirred and N2Keeping the temperature and reacting for 10 hours under the condition;
(4) and (3) viscosity adjustment: after the reaction is finished, decompressing and evaporating to remove isooctane, and finally adding 94.732g of tripropylene glycol diacrylate to adjust the viscosity of the system to obtain the photocuring arabinose-based polyurethane acrylate.
Example 3
The preparation method of the photocuring arabinose-based polyurethane acrylate comprises the following steps:
(1) chain extension: 41.66g of 2-methyl-1, 4-butanediol, 1.232g N-methylmorpholine and 0.704g of dihydroquinoline were put into a 500mL four-necked flask equipped with a mechanical stirrer, a thermometer, a reflux condenser and a gas introduction tube, and stirred to form a homogeneous solution, and N was introduced thereinto2134.56g of hexamethylene diisocyanate is added dropwise through a constant pressure dropping funnel, and the mixture is stirred and reacted for 5 hours at the temperature of 55 ℃;
(2) half end capping: 91.312g of methyl isobutyl ketone and 0.912g of phenothiazine are slowly added into the product in the step (1), the temperature is increased to 75 ℃, stirring is carried out, and N252.056g of hydroxypropyl acrylate is dripped under the condition, and the reaction is carried out for 5 hours under the condition of heat preservation;
(3) end capping: 15.012g of arabinose are added into the product in the step (2) in batches, the temperature is raised to 90 ℃, and the mixture is stirred and N2Keeping the temperature and reacting for 10 hours under the condition;
(4) and (3) viscosity adjustment: after the reaction is finished, reducing pressure and evaporating to remove isooctane, and finally adding 72.988g of 1, 6-hexanediol diacrylate to adjust the viscosity of the system to obtain the photocuring arabinose-based polyurethane acrylate.
Example 4
The preparation method of the photocuring arabinose-based polyurethane acrylate comprises the following steps:
(1) chain extension: in a 500mL four-necked flask equipped with a mechanical stirrer, a thermometer, a reflux condenser and a gas introduction tube, 26.635g of 1, 3-propanediol, 1.684g of organic bismuth and 0.945g of thiodipropionic acid diester were put, and stirred to form a homogeneous solution, and N was introduced thereinto2183.645g of dicyclohexylmethane diisocyanate is added dropwise through a constant pressure dropping funnel, and the mixture is stirred and reacted for 5 hours at 50 ℃;
(2) half end capping: 112.914g of toluene and 1.131g of hydroquinone are slowly added into the product in the step (1), the temperature is raised to 70 ℃, the mixture is stirred, and N is added240.642g of hydroxyethyl acrylate is dripped under the condition, and the reaction is carried out for 8 hours under the condition of heat preservation;
(3) end capping: 15.012g of arabinose are added into the product in the step (2) in batches, the temperature is raised to 100 ℃, and the mixture is stirred and N2Keeping the temperature and reacting for 10 hours under the condition;
(4) and (3) viscosity adjustment: after the reaction is finished, removing toluene by reduced pressure evaporation, and finally adding 50.812g of tetrahydrofuran acrylate to adjust the viscosity of the system to obtain the photocuring arabinose-based polyurethane acrylate.
Example 5
The preparation method of the photocuring arabinose-based polyurethane acrylate comprises the following steps:
(1) chain extension: in a 500mL four-necked flask equipped with a mechanical stirrer, a thermometer, a reflux condenser and a gas conduit were charged 36.048g of 1, 4-butanediol, 1.708g of dioctyltin dilaurate and 0.852g of 2, 6-di-t-butyl-p-cresol, and stirred to form a homogeneous solution, N was introduced into the homogeneous solution2134.56g of hexamethylene diisocyanate is added dropwise through a constant pressure dropping funnel, and the mixture is stirred and reacted for 6 hours at 50 ℃;
(2) half end capping: 111.336g of methyl isobutyl ketone and 1.112g of p-hydroxybenzene methylSlowly adding ether into the product obtained in the step (1), heating to 65 ℃, stirring, and adding N252.06g of 2-hydroxyethyl methacrylate is dripped under the condition, and the reaction is carried out for 7 hours under the condition of heat preservation;
(3) end capping: 15.012g of arabinose are added into the product in the step (2) in batches, the temperature is raised to 90 ℃, and the mixture is stirred and N2Keeping the temperature and reacting for 10 hours under the condition;
(4) and (3) viscosity adjustment: and after the reaction is finished, evaporating under reduced pressure to remove toluene, and finally adding 71.304g of dipropylene glycol diacrylate to adjust the viscosity of the system to obtain the photocuring arabinose-based polyurethane acrylate.
Test example
10g of the arabinourethane acrylate prepared in inventive example 1 was uniformly mixed with 0.3g of 2-hydroxy-2-methyl-1-phenyl-1-propanone and coated on a tin plate to a thickness of about 90 μm at 800mJ/cm2And exposing under a high-pressure mercury lamp with energy to obtain the bio-based photocureable coating, wherein the pencil hardness is 3H (750g load), the T bend test is 0T, and the xenon lamp weather resistance test exceeds 1000H.
Claims (11)
1. The preparation method of the photocuring arabinose-based polyurethane acrylate is characterized by comprising the following steps:
(1) chain extension: putting biological low-carbon glycol, a catalyst and an antioxidant into a reaction vessel, stirring to form a homogeneous solution, and introducing N through a guide pipe2Slowly adding diisocyanate by a dripping device, and stirring and reacting at 45-55 ℃ for 4-6 h;
(2) half end capping: slowly adding solvent and polymerization inhibitor into the product obtained in the step (1), heating to 65-75 ℃, stirring, and adding N2Dripping a photosensitive hydroxyl monomer under the condition, and reacting for 5-8h under the condition of heat preservation;
(3) end capping: adding arabinose into the product in the step (2) in batches, heating to 90-100 ℃, stirring, and adding N2Keeping the temperature and reacting for 10 hours under the condition;
(4) and (3) viscosity adjustment: and after the reaction is finished, removing the solvent by reduced pressure evaporation, and finally adding an active diluent to adjust the viscosity of the system to obtain the photocuring arabinose-based polyurethane acrylate resin.
2. The urethane acrylate according to claim 1, wherein the biological low carbon diol is one or more of 1, 3-propanediol, 1, 4-butanediol, 2-methyl-1, 4-butanediol.
3. The urethane acrylate according to claim 1, wherein the catalyst is one or more of dioctyl dilaurate, organic bismuth, and N-methylmorpholine, and is used in an amount of 0.5-1% by mass based on the total mass of the diol and the diisocyanate.
4. The urethane acrylate according to claim 1, wherein the antioxidant is one or more of 2, 6-di-tert-butyl-p-cresol, thiodipropionic acid diester, dihydroquinoline, and the amount of the antioxidant is 0.3-0.5% of the total mass of the diol and the diisocyanate.
5. The urethane acrylate according to claim 1, wherein the diisocyanate is one or more of isophorone diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane diisocyanate.
6. The urethane acrylate according to claim 1, wherein the solvent is one or more of toluene, isooctane and methyl isobutyl ketone, and is used in an amount of 0.3 to 0.5 times the total mass of the diol, the diisocyanate and the photosensitive hydroxyl monomer.
7. The urethane acrylate according to claim 1, wherein the polymerization inhibitor is one or more of p-hydroxyanisole, hydroquinone and phenothiazine, and the amount of the polymerization inhibitor is 0.3-0.5% of the total mass of the dihydric alcohol, the diisocyanate and the photosensitive hydroxyl monomer.
8. The urethane acrylate according to claim 1, wherein the photosensitive hydroxyl monomer is one or more of hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, hydroxypropyl acrylate.
9. The urethane acrylate according to claim 1, wherein the reactive diluent is one or more selected from the group consisting of tetrahydrofuran acrylate, tripropylene glycol diacrylate, 1, 6-hexanediol diacrylate and dipropylene glycol diacrylate, and is used in an amount of 0.2 to 0.4 times the total mass of the diol, the diisocyanate, the photosensitive hydroxyl monomer and the arabinose.
10. The urethane acrylate according to claim 1, wherein the molar ratio of the biological low carbon diol, the diisocyanate, the photosensitive hydroxyl monomer and the arabinose is 1:2:1: 0.25.
11. A bio-based radiation cured coating prepared by using the arabinourethane acrylate as the main resin in claim 1 and 2-hydroxy-2-methyl-1-phenyl-1-acetone as a photoinitiator has the comprehensive properties of good hardness, flexibility and weather resistance.
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Citations (4)
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|---|---|---|---|---|
| US5283265A (en) * | 1983-12-08 | 1994-02-01 | Hayakawa Rubber Company Limited | Photopolymerizable rubber |
| CN103554393A (en) * | 2013-10-18 | 2014-02-05 | 华中农业大学 | Method for preparing natural polymer matrix light-cured resin |
| CN105885004A (en) * | 2016-06-22 | 2016-08-24 | 江南大学 | Bio-based photo-curable polyurethane and photoresist prepared with same |
| CN108003779A (en) * | 2017-12-19 | 2018-05-08 | 江南大学 | A kind of bio-based materials are modified the preparation method of UV solidfication water polyurethane resins |
-
2018
- 2018-12-04 CN CN201811472881.1A patent/CN111269380A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5283265A (en) * | 1983-12-08 | 1994-02-01 | Hayakawa Rubber Company Limited | Photopolymerizable rubber |
| CN103554393A (en) * | 2013-10-18 | 2014-02-05 | 华中农业大学 | Method for preparing natural polymer matrix light-cured resin |
| CN105885004A (en) * | 2016-06-22 | 2016-08-24 | 江南大学 | Bio-based photo-curable polyurethane and photoresist prepared with same |
| CN108003779A (en) * | 2017-12-19 | 2018-05-08 | 江南大学 | A kind of bio-based materials are modified the preparation method of UV solidfication water polyurethane resins |
Non-Patent Citations (3)
| Title |
|---|
| SNEGIREV, A. I.等: "Synthesis of biodegradable hydroxyl-containing polyurethanes", 《DOPOVIDI AKADEMII NAUK UKRAINS"KOI RSR, SERIYA B: GEOLOGICHNI, KHIMICHNI TA BIOLOGICHNI NAUKI》 * |
| 李医明: "《中药化学 第2版》", 31 August 2018, 上海科学技术出版社 * |
| 甘景镐等: "《天然高分子化学》", 30 September 1993, 高等教育出版社 * |
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