CN111234125A - Aldehyde-adsorbable VOC (volatile organic compound) resin and synthesis method thereof - Google Patents
Aldehyde-adsorbable VOC (volatile organic compound) resin and synthesis method thereof Download PDFInfo
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- CN111234125A CN111234125A CN202010194176.0A CN202010194176A CN111234125A CN 111234125 A CN111234125 A CN 111234125A CN 202010194176 A CN202010194176 A CN 202010194176A CN 111234125 A CN111234125 A CN 111234125A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
- C08F283/008—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00 on to unsaturated polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/2845—Monohydroxy epoxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The invention relates to a synthesis method of aldehyde-adsorbable VOC (volatile organic compound) type resin, which comprises the following steps of reacting dihydric alcohol and diisocyanate according to a molar ratio of 1:2-2.3 at 70-90 ℃ to a-NCO group to a design value under the protection of dry inert gas; then adding hydroxyl epoxy with the same molar quantity with the selected dihydric alcohol, and continuously reacting until the-NCO group reaches the design value; finally, monohydroxy acrylate is added, the reaction is continued until-NCO group disappears, epoxy modified urethane acrylate is obtained, then metal acrylate, acryloyl oxygen acid anhydride compound, stabilizer and thermal initiator are added, and the reaction is carried out for 0.5 to 3 hours at 50 to 80 ℃ until the required viscosity value is reached, thus obtaining the adsorbable aldehyde VOC type resin; the resin prepared by the invention greatly reduces the release of aldehyde VOC, can increase intermolecular crosslinking density so as to improve the mechanical property of a cured product, and has good storage stability.
Description
Technical Field
The invention relates to an aldehyde-adsorbable VOC (volatile organic compound) type violet resin and a synthesis method thereof, belonging to the field of photocuring materials.
Background
Due to the advantages of high curing speed, low energy consumption, excellent performance, low VOC content and emission and the like, the photocuring adhesive is widely applied to various industrial and electronic fields. Nevertheless, the photo-curing adhesive still has many problems to be improved, for example, most photo-curing adhesives release small-molecule Volatile Organic Compounds (VOCs) during curing and subsequent working use, the small-molecule VOCs mainly are cracking products of the photo-initiator such as benzaldehyde besides the volatilization of the reactive diluent, and the small-molecule VOCs are slowly and continuously released during subsequent working, and have harmful effects on the environment and human bodies. With the improvement of science and technology and the enhancement of environmental awareness of people, the governments of all countries have stricter and stricter regulations on VOC emission, and the requirements of all-round product experience of consumers are higher and higher, and the lower the VOC emission is, the better the VOC emission is on the premise of meeting the laws and regulations. Aiming at the problem of aldehyde VOC generated after the photoinitiator is cracked, attention has not been paid at present, relevant research is only rarely reported, and people think that the macromolecular photoinitiator can be used, but the types of the macromolecular photoinitiator are few at present, and in terms of mechanism, part of the macromolecular photoinitiator can still generate volatile aldehyde VOC after the photoinitiator is cracked, and most importantly, the macromolecular photoinitiator is difficult to meet the required performances, such as surface dryness, curing degree, curing speed and the like, so that the use of the macromolecular photoinitiator is limited. Aiming at the problem of aldehyde VOC, the invention provides a resin capable of adsorbing aldehyde VOC to solve the problem.
Disclosure of Invention
In order to solve the problem of harmful aldehyde VOC release in the curing process and the subsequent working and using processes of the existing light-cured adhesive, the invention provides an aldehyde VOC adsorbable resin and a synthesis method thereof, so as to achieve the purpose of reducing the aldehyde VOC release.
The technical scheme for solving the technical problems is as follows:
the aldehyde-adsorbable VOC resin comprises the following components in parts by mass: 50-95 parts of epoxy modified polyurethane acrylate, 1-15 parts of metal acrylate, 1-20 parts of acryloyl oxygen acid anhydride compounds and 0.001-1 part of stabilizing agent.
The aldehyde VOC adsorbable resin has the following molecular structural general formula:
wherein R is1represents-H or-CH3；R2Represents a portion of the diisocyanate molecule that does not contain NCO groups; r3Represents a portion of a diol such as polyether, polyester, polycarbonate or polyolefin, which does not contain an-OH group; r4represents-CH2-or-CH2CH2CH2CH2OCH2-；R5represents-K, -Na or-Li; r represents
-K, -Na or-Li, wherein x, y and z are all positive integers of 1-50.
The invention also provides a synthesis method of the aldehyde-adsorbable VOC type resin, which comprises the following steps of reacting dihydric alcohol and diisocyanate according to a molar ratio of 1:2-2.3 at 70-90 ℃ to enable a-NCO group to reach a design value under the protection of dry inert gas; then adding hydroxyl epoxy with the same molar quantity with the selected dihydric alcohol, and continuously reacting until the-NCO group reaches the design value; and finally, adding monohydroxy acrylate, continuously reacting until-NCO groups disappear to obtain epoxy modified polyurethane acrylate, then adding metal acrylate, an acryloyl oxygen acid anhydride compound, a stabilizer and a thermal initiator accounting for 0.1-3% of the total weight, and reacting for 0.5-3h at 50-80 ℃ to obtain the aldehyde-adsorbable VOC type resin.
Further, in the synthesis method, the diisocyanate is one or a mixture of Toluene Diisocyanate (TDI), isophorone diisocyanate (IPDI), diphenylmethane diisocyanate (MDI) or Hexamethylene Diisocyanate (HDI).
Further, the diol in the synthesis method includes, but is not limited to, one or more of polyether, polyester, polycarbonate or polyolefin diol with molecular weight of 100-. The selection of the other properties to be achieved by the synthetic resin may be made according to the properties desired, such as surface drying, resistance to humidity and heat, resistance to chemical agents, tensile strength, adhesive strength, dielectric properties, etc.
Further, in the synthesis method, the hydroxyl epoxy is in a structure that one end of a molecular chain is hydroxyl and the other end is epoxy, and the hydroxyl epoxy comprises but is not limited to one or a mixture of epoxypropanol and 4- (ethylene oxide-2-methoxy) -1-butanol.
Further, the monohydroxy acrylate in the synthesis method is a structure with one end of a molecular chain being hydroxyl and the other end being acryloxy, and includes but is not limited to one or a mixture of more of hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate and hydroxybutyl (meth) acrylate.
Further, in the synthesis method, the metal acrylate is one or a mixture of sodium (meth) acrylate, potassium (meth) acrylate and lithium (meth) acrylate.
Further, in the synthesis method, the compound of the acryloxy acid anhydride is in a structure that one end of a molecular chain is anhydride and the other end is acryloxy, and the compound of the acryloxy acid anhydride comprises but is not limited to one or a mixture of two of 4-acryloxy ethyl trimellitic anhydride and 4-methacryloxy ethyl trimellitic anhydride.
Further, the stabilizer in the synthesis method is one or a mixture of boric acid ester, aluminum chelate and organic acid, including 2, 2-methoxy bis (5, 5-dimethyl-1, 3, 2-oxaborole), trimethyl borate, triethyl borate, tri-n-propyl borate, triisopropyl borate, tri-n-butyl borate, tripentyl borate, trihexyl borate, tricyclohexyl borate, trioctyl borate, tridecyl borate, dodecyl borate, trihexadecyl borate, trioctadecyl borate, tris (2-ethylhexyloxy) borane, bis (1,4,7, 10-tetraoxaundecyl) (1,4,7, 13-pentaoxatetradecyl) (1,4,7 ー -trioxaundecyl) borane, tribenzyl borate, triphenyl borate, or a mixture of boric acid and organic acid, Tricresyl borate, triethanolamine borate, barbituric acid, and the like.
Further, the thermal initiator is Benzoyl Peroxide (BPO) or Azobisisobutyronitrile (AIBN).
The invention has the beneficial effects that: the invention aims at aldehyde compounds generated by cracking of a photoinitiator, prepares resin capable of adsorbing aldehyde VOC, and utilizes the heat released in the photocuring process of aldehyde and acid anhydride under the base catalysis to react to generate carboxylic acid; and the carboxylic acid can react with the epoxy group, so that the benzaldehyde is grafted to a macromolecular chain instead of simple physical adsorption, and the release of aldehyde VOC is greatly reduced. And the further beneficial effect is that carboxylic acid generated after the anhydride groups on the molecular chain react with aldehydes can react with epoxy groups under the action of a catalyst, so that the intermolecular crosslinking density can be increased, and the mechanical property of the cured product can be improved. In addition, epoxy group, acid anhydride and alkaline catalyst are introduced to a molecular chain, so that the storage stability of the resin can be greatly improved.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1
Weighing 200g of dewatered polytetrahydrofuran ether glycol PTMG200 and 714g of TDI, sequentially adding into a three-neck flask, and reacting for 2h at 85 ℃ under the protection of dry nitrogen; adding 146.2g of 4- (ethylene oxide-2-yl methoxy) -1-butanol, and reacting at 85 ℃ for 1.5 h; adding 128g of hydroxyethyl acrylate, reacting at 85 ℃ for 1.5 h; 6g of potassium acrylate, 76g of 4-methacryloyloxyethyl trimellitic anhydride, 0.1g of tricetyl borate and 0.3g of benzoyl peroxide are added to react for 2 hours at 70 ℃ to obtain the aldehyde-adsorbable VOC type resin.
Example 2
Weighing 400g of dehydrated polypropylene glycol PPG400 and 344g of HDI, sequentially adding into a three-neck flask, and reacting at 85 ℃ for 2h under the protection of dry nitrogen; adding 74g of epoxy propanol, and reacting at 85 ℃ for 1.5 h; adding 128g of hydroxyethyl acrylate, reacting at 85 ℃ for 1.5 h; 6g of potassium acrylate, 76g of 4-methacryloyloxyethyl trimellitic anhydride, 0.1g of trioctadecyl borate and 0.3g of benzoyl peroxide are added to react for 2 hours at 70 ℃ to obtain the aldehyde-adsorbable VOC type resin.
Comparative example 1
Weighing 200g of dewatered polytetrahydrofuran ether glycol PTMG200 and 714g of TDI, sequentially adding into a three-neck flask, and reacting for 2h at 85 ℃ under the protection of dry nitrogen; adding 104.2g of 4-methoxy-1-butanol, and reacting at 85 ℃ for 1.5 h; adding 128g of hydroxyethyl acrylate, reacting at 85 ℃ for 1.5 h; 6g of potassium acrylate, 76g of 4-methacryloyloxyethyl trimellitic anhydride, 0.1g of tricetyl borate and 0.3g of benzoyl peroxide are added and reacted for 2 hours at 70 ℃ to obtain the product.
Comparative example 2
Weighing 200g of dewatered polytetrahydrofuran ether glycol PTMG200 and 714g of TDI, sequentially adding into a three-neck flask, and reacting for 2h at 85 ℃ under the protection of dry nitrogen; adding 146.2g of 4- (ethylene oxide-2-yl methoxy) -1-butanol, and reacting at 85 ℃ for 1.5 h; adding 128g of hydroxyethyl acrylate, reacting at 85 ℃ for 1.5 h; 76g of 4-methacryloyloxyethyl trimellitic anhydride, 0.1g of tricetyl borate and 0.3g of benzoyl peroxide are added and reacted for 2 hours at 70 ℃ to obtain the product.
Comparative example 3
Weighing 200g of dewatered polytetrahydrofuran ether glycol PTMG200 and 714g of TDI, sequentially adding into a three-neck flask, and reacting for 2h at 85 ℃ under the protection of dry nitrogen; adding 146.2g of 4- (ethylene oxide-2-yl methoxy) -1-butanol, and reacting at 85 ℃ for 1.5 h; adding 128g of hydroxyethyl acrylate, reacting at 85 ℃ for 1.5 h; adding 6g of potassium acrylate and 0.25g of benzoyl peroxide, and reacting at 70 ℃ for 2 hours to obtain a product.
Comparative example 4
Weighing 200g of dewatered polytetrahydrofuran ether glycol PTMG200 and 714g of TDI, sequentially adding into a three-neck flask, and reacting for 2h at 85 ℃ under the protection of dry nitrogen; adding 146.2g of 4- (ethylene oxide-2-yl methoxy) -1-butanol, and reacting at 85 ℃ for 1.5 h; adding 128g of hydroxyethyl acrylate, reacting at 85 ℃ for 1.5 h; after cooling to room temperature, 6g of potassium acrylate, 76g of 4-methacryloyloxyethyl trimellitic anhydride and 0.1g of tricetyl borate were added, and the mixture was stirred until the mixture was dissolved uniformly.
The performance of one of the VOC-adsorbable resin of the present invention was tested by the following test.
1. Storage stability: both the examples and comparative examples were placed in an oven at 60 ℃ for 7 days, and the presence or absence of phase separation and gelation was observed.
VOC content test: examples and pairsRespectively adding 4 percent of photoinitiator 184 which can generate benzaldehyde after cracking into the proportional samples, and then carrying out VOC content test according to GB/T34675-2017, namely weighing a certain mass of glue solution m0Curing by ultraviolet light, placing the cured product in an oven at 110 ℃ for 1h, cooling to room temperature, and weighing m1VOC content ═ m0-m1)/m0Results are expressed as percentages.
VOC species testing: respectively adding 4% of photoinitiator 184 which can generate benzaldehyde after cracking into samples of examples and comparative examples, weighing a certain mass of glue solution, curing by using ultraviolet light, swelling and extracting residual micromolecules in a cured product by using a solvent, and testing whether aldehyde components exist in the glue solution by using a gas chromatography-mass spectrometer.
The test results are shown in table 1:
TABLE 1 comparative test results of examples and comparative examples
| Test specimen | Stability in storage | VOC content | Class of VOC |
| Example 1 | No precipitation and no gel | 0.2％ | Free of aldehydes |
| Example 2 | No precipitation and no gel | 0.16％ | Free of aldehydes |
| Comparative example 1 | No precipitation and no gel | 1.9％ | Aldehydes containing |
| Comparative example 2 | No precipitation and no gel | 1.7％ | Aldehydes containing |
| Comparative example 3 | No precipitation and no gel | 2.2％ | Aldehydes containing |
| Comparative example 4 | Severe precipitation and no gel | 1.4％ | Aldehydes containing |
From the above results, it can be seen that an aldehyde VOC adsorbable resin of the present invention can effectively reduce aldehyde VOCs generated during curing without a decrease in storage stability, as compared to conventional urethane acrylates.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (4)
1. A synthesis method of aldehyde-adsorbable VOC (volatile organic compound) type resin is characterized by comprising the following steps of reacting dihydric alcohol and diisocyanate according to a molar ratio of 1:2-2.3 at 70-90 ℃ to enable-NCO groups to reach design values under the protection of dry inert gas; then adding hydroxyl epoxy with the same molar quantity with the selected dihydric alcohol, and continuously reacting until the-NCO group reaches the design value; and finally, adding monohydroxy acrylate, continuously reacting until-NCO groups disappear to obtain epoxy modified polyurethane acrylate, then adding metal acrylate, an acryloyl oxygen acid anhydride compound, a stabilizer and a thermal initiator accounting for 0.1-3% of the total weight, and reacting for 0.5-3h at 50-80 ℃ to obtain the aldehyde-adsorbable VOC type resin.
2. The synthesis method of claim 1, wherein the aldehyde VOC-type resin capable of adsorbing has the following molecular structural formula:
wherein R is1represents-H or-CH3；R2Represents a portion of the diisocyanate molecule that does not contain NCO groups; r3Represents a portion of a diol such as polyether, polyester, polycarbonate or polyolefin, which does not contain an-OH group; r4represents-CH2-or-CH2CH2CH2CH2OCH2-；R5represents-K, -Na or-Li; r represents
-K, -Na or-Li, wherein x, y and z are all positive integers of 1-50.
3. The synthesis method according to claim 1, wherein the diisocyanate is one or a mixture of toluene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate or hexamethylene diisocyanate; the dihydric alcohol comprises one or a mixture of more of polyether, polyester, polycarbonate or polyolefin dihydric alcohol with the molecular weight of 100-3000; the hydroxyl epoxy is one or a mixture of epoxypropanol and 4- (ethylene oxide-2-methoxyl) -1-butanol.
4. The synthesis method of claim 1, wherein the monohydroxy acrylate is one or more of hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, and hydroxybutyl (meth) acrylate; the metal acrylate is one or a mixture of more of sodium (meth) acrylate, potassium (meth) acrylate and lithium (meth) acrylate; the acryloyl oxygen anhydride compound is one or a mixture of two of 4-acryloyloxyethyl trimellitic anhydride and 4-methacryloyloxyethyl trimellitic anhydride; the stabilizer is 2, 2-monooxybis (5, 5-dimethyl-1, 3, 2-oxaborole), trimethyl borate, triethyl borate, tri-n-propyl borate, triisopropyl borate, tri-n-butyl borate, tripentyl borate, trihexyl borate, tricyclohexyl borate, trioctyl borate, tridecyl borate, dodecyl borate, hexadecyl borate, octadecyl borate, tris (2-ethylhexyloxy) borane, bis (1,4,7, 10-tetraoxaundecyl) (1,4,7,10, 13-pentaoxatetradecyl) (1,4,7 ー -trioxaundecyl) borane, tribenzyl borate, triphenyl borate, tricresyl borate, triethanolamine borate, barbituric acid, or a mixture thereof; the thermal initiator is benzoyl peroxide or azobisisobutyronitrile.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115286744A (en) * | 2022-08-18 | 2022-11-04 | 烟台德邦科技股份有限公司 | Resin capable of adsorbing aromatic aldehyde and synthesis method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH517794A (en) * | 1968-06-12 | 1972-01-15 | Bayer Ag | Process for the preparation of graft polymers containing epoxy groups |
| CN104031231A (en) * | 2014-06-19 | 2014-09-10 | 合肥工业大学 | Ultraviolet-curing waterborne epoxy-polyurethane-acrylate copolymer resin anticorrosive coating and preparation method thereof |
| CN105086771A (en) * | 2015-09-22 | 2015-11-25 | 南昌航空大学 | Preparation method for polyurethane-reinforced epoxy resin photocureable coating |
-
2020
- 2020-03-19 CN CN202010194176.0A patent/CN111234125A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH517794A (en) * | 1968-06-12 | 1972-01-15 | Bayer Ag | Process for the preparation of graft polymers containing epoxy groups |
| CN104031231A (en) * | 2014-06-19 | 2014-09-10 | 合肥工业大学 | Ultraviolet-curing waterborne epoxy-polyurethane-acrylate copolymer resin anticorrosive coating and preparation method thereof |
| CN105086771A (en) * | 2015-09-22 | 2015-11-25 | 南昌航空大学 | Preparation method for polyurethane-reinforced epoxy resin photocureable coating |
Non-Patent Citations (1)
| Title |
|---|
| VADIM V. KRONGAUZ: "Crosslink density dependence of polymer degradation kinetics: Photocrosslinked acrylates", 《THERMOCHIMICA ACTA》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115286744A (en) * | 2022-08-18 | 2022-11-04 | 烟台德邦科技股份有限公司 | Resin capable of adsorbing aromatic aldehyde and synthesis method thereof |
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