CN104788644B - One kind can UV/ moistures double cured resin and its synthetic method - Google Patents
One kind can UV/ moistures double cured resin and its synthetic method Download PDFInfo
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- CN104788644B CN104788644B CN201510211498.0A CN201510211498A CN104788644B CN 104788644 B CN104788644 B CN 104788644B CN 201510211498 A CN201510211498 A CN 201510211498A CN 104788644 B CN104788644 B CN 104788644B
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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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
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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
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
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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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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention provide it is a kind of can UV/ moisture double cured resins synthetic method, including：HDI trimer, hydroxy acrylate, polymerization inhibitor MEHQ, catalyst dibutyltin dilaurylate are added in the three-necked flask with thermometer, it is warming up to 65 degree, start dropwise addition two (γ trimethoxy-silylpropyls) amine, by temperature control at 70 75 degree, 2 3h are reacted.NCO group is analyzed with infrared spectrometer, when NCO peaks are unchanged, stop heating response, can obtain UV/ moisture double cured resins.The resin that the present invention is designed can UV photocurings, it is and moisture cured, solve the problem of dash area can not solidify in photo-polymerization process；Moreover, with resin of the methoxy silane as moisture-curable reactive group, comparing with the resin blocked using isocyanates as reactive group, with more stable reaction speed and solidfied material effect, product deep cure effect is more preferable.
Description
Technical field
Can UV/ moistures double cured resin and its synthetic method the present invention relates to one kind, it is adaptable to shading or trnaslucent materials
Bonding application, belong to photo-curing material field.
Background technology
Curable adhesive is because its curing rate is fast, environment-friendly, energy-output ratio is few, solvent-free volatilization etc. is numerous prominent
Go out advantage and be widely studied, and promoted rapidly in all trades and professions.But curable adhesive also has the office of itself
Limit, trnaslucent materials or component shading light part to the absorption of ultraviolet light, stop and reflect, often efficiency of initiation is not or not light trigger
Height, adhesive is not easy completion of cure so that adhesive glue-line mechanical property is substantially reduced.
To solve the shortcoming that dash area can not solidify in photo-polymerization process, researchers have been developed photocuring and other
The dual UV curable paint that curing mode combines.In dual UV curable paint, the crosslinking of system or polymerisation are by two
What the individual independent stage with differential responses principle completed, one of them stage is and another rank by photocuring reaction
Section is carried out by dark reaction, and dark reaction includes heat cure, moisture-curable, oxygen solidification or anaerobic curing reaction etc..So
Just it can make system fast shaping using photocuring or reach " surface drying ", and make " shade " part or floor portions using dark reaction
Completion of cure, so as to reach " doing solid work " of system.
The content of the invention
In view of the deficiencies of the prior art, the present invention provides one kind can UV/ moistures double cured resin and its synthetic method so that
Curable adhesive is fully cured in dash area, and photocuring reaction and moisture-curable reaction combine well, make
Reaction system performance is homogeneous.
The technical scheme that the present invention solves above-mentioned technical problem is as follows：One kind can UV/ moisture double cured resins, it is described can
UV/ moistures double cured resin is methoxy silane blocking modification acrylate, and its structural formula is by following formulas（Ⅰ）Represent：
（Ⅰ）
Wherein：R1Representative-C2H4-、-C3H6-、-C4H8- in one or more；R2Representative-H ,-CH3In one kind or two
Kind.
Present invention also offers it is a kind of can UV/ moisture double cured resins synthetic method, including：
By HDI trimer（Beyer Co., Ltd, desmodur N3300）80-110g, hydroxy acrylate 5-12g, polymerization inhibitor
MEHQ 0.1g, catalyst dibutyltin dilaurylate 0.01g are added in the three-necked flask with thermometer, heating
To 65 degree, start dropwise addition two (γ-trimethoxy-silylpropyl) amine（cas：82985-35-1）3-6g, temperature control is existed
70-75 degree, reacts 2-3h.NCO group is analyzed with infrared spectrometer, when NCO peaks are unchanged, stops heating response, can obtain
UV/ moisture double cured resins.Reaction equation is as follows：
On the basis of above-mentioned technical proposal, the present invention can also do following improvement.
Further, hydroxy acrylate described in synthetic method is hydroxy-ethyl acrylate, hydroxyethyl methacrylate, propylene
One kind or any several mixture in sour hydroxypropyl acrylate or hydroxy propyl methacrylate etc..
Further, it is a kind of can UV/ moisture double cured resins synthetic method, including：
By HDI trimer（Beyer Co., Ltd, desmodur N3300）80g, hydroxy-ethyl acrylate 5g, polymerization inhibitor para hydroxybenzene
Methyl ether 0.1g, catalyst dibutyltin dilaurylate 0.01g are added in the three-necked flask with thermometer, are warming up to 65 degree,
Start dropwise addition two (γ-trimethoxy-silylpropyl) amine（cas：82985-35-1）3g, by temperature control at 75 degree, instead
Answer 2h.NCO group is analyzed with infrared spectrometer, when NCO peaks are unchanged, stops heating response, obtaining can the double solidification of UV/ moistures
Resin.
Further, it is a kind of can UV/ moisture double cured resins synthetic method, including：
By HDI trimer（Beyer Co., Ltd, desmodur N3300）110g, hydroxypropyl acrylate 12g, polymerization inhibitor are to hydroxyl
Methyl phenyl ethers anisole 0.1g, catalyst dibutyltin dilaurylate 0.01g are added in the three-necked flask with thermometer, are warming up to 65
Degree, starts dropwise addition two (γ-trimethoxy-silylpropyl) amine（cas：82985-35-1）6g, by temperature control at 70 degree,
React 3h.Analyze NCO group with infrared spectrometer, when NCO peaks are unchanged, stop heating response, obtain can UV/ moistures it is double solid
Change resin.
Further, it is a kind of can UV/ moisture double cured resins synthetic method, including：
By HDI trimer（Beyer Co., Ltd, desmodur N3300）100g, hydroxy-ethyl acrylate 8g, polymerization inhibitor are to hydroxyl
Methyl phenyl ethers anisole 0.1g, catalyst dibutyltin dilaurylate 0.01g are added in the three-necked flask with thermometer, are warming up to 65
Degree, starts dropwise addition two (γ-trimethoxy-silylpropyl) amine（cas：82985-35-1）4g, by temperature control at 73 degree,
React 2h.Analyze NCO group with infrared spectrometer, when NCO peaks are unchanged, stop heating response, obtain can UV/ moistures it is double solid
Change resin.
Further, it is a kind of can UV/ moisture double cured resins synthetic method, including：
By HDI trimer（Beyer Co., Ltd, desmodur N3300）90g, hydroxyethyl methacrylate 12g, polymerization inhibitor pair
Hydroxyanisol 0.1g, catalyst dibutyltin dilaurylate 0.01g are added in the three-necked flask with thermometer, are warming up to
65 degree, start dropwise addition two (γ-trimethoxy-silylpropyl) amine（cas：82985-35-1）4g, by temperature control 75
Degree, reacts 2h.NCO group is analyzed with infrared spectrometer, when NCO peaks are unchanged, stops heating response, obtaining can UV/ moisture
Double cured resin.
Further, it is a kind of can UV/ moisture double cured resins synthetic method, including：
By HDI trimer（Beyer Co., Ltd, desmodur N3300）110g, hydroxy propyl methacrylate 8g, polymerization inhibitor pair
Hydroxyanisol 0.1g, catalyst dibutyltin dilaurylate 0.01g are added in the three-necked flask with thermometer, are warming up to
65 degree, start dropwise addition two (γ-trimethoxy-silylpropyl) amine（cas：82985-35-1）5g, by temperature control 70
Degree, reacts 3h.NCO group is analyzed with infrared spectrometer, when NCO peaks are unchanged, stops heating response, obtaining can UV/ moisture
Double cured resin.
The beneficial effects of the invention are as follows：The resin of this patent design has on special chemical constitution, the strand of resin
There are 2 can carry out the acrylate group of UV photocurings, also one can carry out the methoxy silane base of moisturecuring with steam
Group, both groups make resin possess can UV photocurings, and moisture cured function solves cloudy in photo-polymerization process
The problem of shadow part can not solidify；Moreover, with resin of the methoxy silane as moisture-curable reactive group, and with isocyanates
The resin blocked as reactive group compares, with more stable reaction speed and solidfied material effect, product deep cure effect
More preferably；In addition, synthesis process is simple, be easily controlled, it is not necessary to use special equipment, solvent-free, production cost is low.
Embodiment
The principles and features of the present invention are described below, and the given examples are served only to explain the present invention, is not intended to limit
Determine the scope of the present invention.
Embodiment 1
By HDI trimer（Beyer Co., Ltd, desmodur N3300）80g, hydroxy-ethyl acrylate 5g, polymerization inhibitor para hydroxybenzene
Methyl ether 0.1g, catalyst dibutyltin dilaurylate 0.01g are added in the three-necked flask with thermometer, are warming up to 65 degree,
Start dropwise addition two (γ-trimethoxy-silylpropyl) amine（cas：82985-35-1）3g, by temperature control at 75 degree, instead
Answer 2h.NCO group is analyzed with infrared spectrometer, when NCO peaks are unchanged, stops heating response, obtaining can the double solidification of UV/ moistures
Resin.
Embodiment 2
By HDI trimer（Beyer Co., Ltd, desmodur N3300）110g, hydroxypropyl acrylate 12g, polymerization inhibitor are to hydroxyl
Methyl phenyl ethers anisole 0.1g, catalyst dibutyltin dilaurylate 0.01g are added in the three-necked flask with thermometer, are warming up to 65
Degree, starts dropwise addition two (γ-trimethoxy-silylpropyl) amine（cas：82985-35-1）6g, by temperature control at 70 degree,
React 3h.Analyze NCO group with infrared spectrometer, when NCO peaks are unchanged, stop heating response, obtain can UV/ moistures it is double solid
Change resin.
Embodiment 3
By HDI trimer（Beyer Co., Ltd, desmodur N3300）100g, hydroxy-ethyl acrylate 8g, polymerization inhibitor are to hydroxyl
Methyl phenyl ethers anisole 0.1g, catalyst dibutyltin dilaurylate 0.01g are added in the three-necked flask with thermometer, are warming up to 65
Degree, starts dropwise addition two (γ-trimethoxy-silylpropyl) amine（cas：82985-35-1）4g, by temperature control at 73 degree,
React 2h.Analyze NCO group with infrared spectrometer, when NCO peaks are unchanged, stop heating response, obtain can UV/ moistures it is double solid
Change resin.
Embodiment 4
By HDI trimer（Beyer Co., Ltd, desmodur N3300）90g, hydroxyethyl methacrylate 12g, polymerization inhibitor pair
Hydroxyanisol 0.1g, catalyst dibutyltin dilaurylate 0.01g are added in the three-necked flask with thermometer, are warming up to
65 degree, start dropwise addition two (γ-trimethoxy-silylpropyl) amine（cas：82985-35-1）4g, by temperature control 75
Degree, reacts 2h.NCO group is analyzed with infrared spectrometer, when NCO peaks are unchanged, stops heating response, obtaining can UV/ moisture
Double cured resin.
Embodiment 5
By HDI trimer（Beyer Co., Ltd, desmodur N3300）110g, hydroxy propyl methacrylate 8g, polymerization inhibitor pair
Hydroxyanisol 0.1g, catalyst dibutyltin dilaurylate 0.01g are added in the three-necked flask with thermometer, are warming up to
65 degree, start dropwise addition two (γ-trimethoxy-silylpropyl) amine（cas：82985-35-1）5g, by temperature control 70
Degree, reacts 3h.NCO group is analyzed with infrared spectrometer, when NCO peaks are unchanged, stops heating response, obtaining can UV/ moisture
Double cured resin.
Comparative example 1
Accurately weigh polyether Glycols 100g, hydroxy ethyl（HEA）8g, polymerization inhibitor MEHQ 0.1g, urge
Agent dibutyl tin laurate 0.01g, is added in the three-necked flask with thermometer, is warming up to 65 degree, starts that 21g is added dropwise
IPDI, by temperature control in 70-75 degree, reacts 2.5h.The content of NCO group is analyzed with infrared spectrometer, treats that NCO peak is complete
During disappearance, heating response can be stopped, polyether polyurethane-acrylate is can obtain.
Comparative example 2
Accurately weigh polyester diol 100g, acrylic acid hydroxypropyl（HPA）8g, polymerization inhibitor MEHQ 0.1g, urge
Agent dibutyl tin laurate 0.01g, is added in the three-necked flask with thermometer, is warming up to 65 degree, starts that 24g is added dropwise
TDI, by temperature control in 70-75 degree, reacts 2.5h.The content of NCO group is analyzed with infrared spectrometer, treats that NCO peak is complete
During disappearance, heating response can be stopped, polyester polyurethane acrylate is can obtain.
By the following experimental test present invention can UV/ moisture double cured resins performance.
The curing performance of test example 1 is tested
Embodiment 1-5 sample and existing common curable adhesive pair of mechanical property has been subjected to by the following method
Than test：
Method for making sample：Glue is coated in two blocks of translucent sheet materials and solidified；
Photo curing condition：Light intensity 14mW/cm2, light application time 100s；
Post cure condition：Room temperature is placed 7 days.
The Mechanics Performance Testing of test example 2
Hardness test：According to GB/T 531-1999 tests；
Tensile strength is tested：According to GB/T528-1998 tests；
Shear strength test：According to GB/T7124-1986 tests.
Test result is as shown in table 1.
Sample made from the embodiment 1-5 of table 1 and usual resins performance comparison test result
It can be seen from the results above that the present invention can UV/ moistures double cured resin compared with the prior art, solid state
It is good, and solidfied material mechanical property is good, can reach Special use requirement.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and
Within principle, any modification, equivalent substitution and improvements made etc. should be included in the scope of the protection.
Claims (3)
1. one kind can UV/ moisture double cured resins, it is characterised in that its structural formula is by following formulas（Ⅰ）Represent：
（Ⅰ）
Wherein：R1Representative-C2H4-、-C3H6-、-C4H8- in one kind；R2Representative-H ,-CH3In one kind；
It is described can UV/ moisture double cured resins synthetic method, including：By HDI trimer 80-110g, hydroxy acrylate 5-
12g, polymerization inhibitor MEHQ 0.1g, catalyst dibutyltin dilaurylate 0.01g are added to three mouthfuls with thermometer
In flask, 65 degree are warming up to, starts dropwise addition two (γ-trimethoxy-silylpropyl) amine 3-6g, by temperature control in 70-75
Degree, reacts 2-3h；NCO group is analyzed with infrared spectrometer, when NCO peaks are unchanged, stop heating response, obtains UV/ moistures
Double cured resin.
2. resin according to claim 1, it is characterised in that the hydroxy acrylate is hydroxy-ethyl acrylate, methyl
One kind in hydroxy-ethyl acrylate, hydroxypropyl acrylate or hydroxy propyl methacrylate.
3. resin according to claim 1, it is characterised in that the HDI trimer is Beyer Co., Ltd desmodur
N3300。
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| CN105273157B (en) * | 2015-10-22 | 2017-12-26 | 广东工业大学 | A kind of hypoxemia inhibition nano hybridization filler of uV curable and preparation method thereof |
| WO2018087743A1 (en) * | 2016-11-14 | 2018-05-17 | 積水化学工業株式会社 | Moisture-curable resin composition and assembled component |
| CN107674178A (en) * | 2017-10-17 | 2018-02-09 | 烟台信友新材料股份有限公司 | A kind of flexibility double cured resin and preparation method thereof |
| CN112552866B (en) * | 2020-12-29 | 2022-05-20 | 烟台信友新材料有限公司 | UV-LED and moisture dual-curing environment-friendly three-proofing adhesive and preparation method thereof |
| CN113185670B (en) * | 2021-04-28 | 2023-03-17 | 广州市白云化工实业有限公司 | Organic silicon modified acrylate, silane modified polyether adhesive and preparation method thereof |
| CN113980582B (en) * | 2021-10-08 | 2023-09-15 | 烟台德邦科技股份有限公司 | Light, heat and moisture curable adhesive and preparation method thereof |
| CN114163972B (en) * | 2021-12-30 | 2023-07-14 | 烟台信友新材料有限公司 | High-wettability environment-friendly three-proofing adhesive and preparation method thereof |
| CN115746602B (en) * | 2022-11-12 | 2023-12-01 | 烟台德邦科技股份有限公司 | High-reliability UV protective coating and preparation method thereof |
| CN116041656A (en) * | 2023-02-10 | 2023-05-02 | 广州五行材料科技有限公司 | Organic silicon UV moisture curing resin and preparation method thereof |
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| CN102344539B (en) * | 2011-07-15 | 2013-11-27 | 深圳职业技术学院 | Silicon-containing double-curing group resin and preparation method thereof |
| CN104194705B (en) * | 2014-09-04 | 2016-01-13 | 烟台德邦科技有限公司 | Electronic package material of a kind of room temperature fast-curing and preparation method thereof |
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