CN105418419A - Dimer acid modified epoxy resin and preparation method therefor - Google Patents
Dimer acid modified epoxy resin and preparation method therefor Download PDFInfo
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- CN105418419A CN105418419A CN201510736988.2A CN201510736988A CN105418419A CN 105418419 A CN105418419 A CN 105418419A CN 201510736988 A CN201510736988 A CN 201510736988A CN 105418419 A CN105418419 A CN 105418419A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Epoxy Resins (AREA)
Abstract
The invention discloses dimer acid modified epoxy resin. The epoxy resin has a structural formula represented by a formula shown in the description. The invention also discloses a method for preparing the dimer acid modified epoxy resin. The method comprises the following steps: weighing epoxy resin, putting the weighed epoxy resin in a three-mouthed flask, adding dimer acid into the three-mouthed flask, introducing dry nitrogen gas into the three-mouthed flask, heating the three-mouthed flask to the temperature of 100-110 DEG C, and adding 2wt% of 1,4-dioxane into the three-mouthed flask; and after the temperature is maintained stable, adding a catalyst tetrabutylammonium bromide into the three-mouthed flask, stopping nitrogen gas introducing, adding a polymerization inhibitor into a system when the acid number of the system is lower than 30mgKOH/g during reaction, adding acrylic acid or methylacrylic acid into the three-mouthed flask, stopping the reaction when the acid number of the system is lower than 10mgKOH/g during the reaction, thereby obtaining the product. The dimer acid modified epoxy resin and the preparation method therefor have the advantages that the toughening effect is good, the functionality of modified resin is not changed, the curing rate is higher, and the hardness is not lowered obviously.
Description
Technical field
The invention belongs to the light-cured resin synthesis field of coatings industry, particularly relate to a kind of dimer acid modified epoxy resin and preparation method thereof.
Technical background
Ultraviolet light polymerization is a kind of surface treatment technology of material occurred the sixties in 20th century, utilizes UV-light initiation to have chemically active liquid material rapid polymerization and is cross-linked, solidify to form solid-state coating.Photocuring technology is the surface treatment technology of material of a kind of efficient, environmental protection, energy-conservation, high-quality.There is the feature such as efficient, wide adaptability, economy, energy-conservation, environmental friendliness.Photocuring resin is the photoresist that a kind of molecular weight is lower, has the functional group that can carry out photocuring reaction, as acrylic double bond, epoxy etc.In photocuring product compositions, resin is the main body of photocuring product, and its performance determines the performance of the rear material of solidification substantially.
Epocryl is most widely used general, the Photocurable oligomers that consumption is maximum of curtain wall, is generally obtained by epoxy resin and acroleic acid esterification.The most frequently used is bisphenol-a epoxy acrylate resin.Containing benzene ring structure in bisphenol A epoxy acrylate molecular structure, after solidification, material has higher rigidity, intensity, thermostability, and the hydroxyl of side chain is conducive to the attachment of polar substrates simultaneously, is also conducive to the wetting of pigment.In addition, also there is the advantages such as the chemical proofing of quick solidifying, high gloss, high rigidity and excellence.But there is the shortcomings such as cured film flexibility is poor, fragility is high.Therefore, by high flexibility material, an epoxide modified main direction of studying is become to epoxy resin modification.
Vegetables oil dimeracid is by being decomposed into by vegetables oil by polymerization processes therewith after vegetable oil acid, the dimer with the oleic acid of C36 structure prepared.Because its raw material sources are in natural vegetable oil acid, there is the features such as low price, flexible, skin irritation is little.Traditional oleic acid or plant oil modified epoxy resin, vegetables oil dimer acid modified epoxy resin vegetables oil link be positioned on the molecular side chain of modified epoxy resin, its toughening effect, solidification rate and hardness are to be improved.
Summary of the invention
The present invention is directed to above-mentioned technical problem, provide that a kind of toughening effect is good, the functionality that do not change modified resin, there is the dimer acid modified epoxy resin and preparation method thereof of higher solidification rate, not obvious reduction hardness.
The present invention is solved the problems of the technologies described above by following technique means: a kind of dimer acid modified epoxy resin, is characterized in that, the structural formula of described epoxy resin is:
The present invention also discloses a kind of method preparing above-mentioned dimer acid modified epoxy resin, and described method comprises the steps:
(1) take epoxy resin in there-necked flask, add dimeracid, pass into drying nitrogen, be warming up to 100 DEG C-110 DEG C, and add 2wt%1,4-dioxane;
(2) temperature maintain stable after, add catalyzer Tetrabutyl amonium bromide, stop passing into nitrogen, the acid number reacted to system is less than 30mgKOH/g;
(3) add stopper to system, and add acrylic or methacrylic acid, react stopped reaction when being less than 10mgKOH/g to system acid number, obtain product.
Preferably, described epoxy resin can be bisphenol A type epoxy resin E51 or bisphenol A type epoxy resin E44.
Preferably, in described dimeracid, dimer is 80wt%, and tripolymer is 20wt%, and carboxyl-content is 0.35mol/100g.
Preferably, in described dimeracid, dimer is 95wt%, and tripolymer is 5wt%, and carboxyl-content is 0.35mol/100g.
Preferably, the mol ratio of epoxy group(ing) and carboxyl is 1.05:1; Its epoxy group is provided by epoxy resin, and carboxyl is provided by dimeracid and acrylic or methacrylic acid, and the carboxyl mol ratio that dimeracid and acrylic or methacrylic acid provide is 1-4:1.
Preferably, described stopper comprises relative to the acrylic or methacrylic acid MEHQ of 0.5wt% and the cupric chloride of 0.1wt%.
Preferably, catalyzer is Tetrabutyl amonium bromide, and add-on is the 0.5wt%-1wt% of step (2) system.
The present invention for raw material, prepares dimer acid modified epoxy resin by carboxyl and epoxy reaction with dimeracid and bisphenol A type epoxy resin, then with acrylic or methacrylic acid-respons, preparation has the modified epoxy acrylic ester resin of photocuring activity.Its reaction equation is as follows:
Dimer acid modified epoxy resin prepared by the present invention, because dimeracid structure is positioned on the main chain of molecular chain, but not be positioned on side chain, the flexibility of molecule can be improved, do not reduce the functionality of epoxy simultaneously, play self-plasticizing action to epoxy molecule, synthesized resin viscosity is starkly lower than epoxy acrylate viscosity of the same type.Meanwhile, the toughness of epoxy resin is improved.By regulating molecular weight and the molecular weight distribution of the adjustable resin of mol ratio of dimeracid carboxyl and epoxy group(ing), thus regulate Tg and the hardness of resin.Fatty acid for modification derives from natural product, low irritant, cheap and easy to get, environmental friendliness.
Specific embodiment
Embodiment 1
Take 100g bisphenol A type epoxy resin E51 in there-necked flask, (dimer is 80wt%, and tripolymer is 20wt% to add dimeracid, carboxyl-content is 0.35mol/100g) 71.4g, pass into drying nitrogen, be warming up to 100 DEG C, and add the Isosorbide-5-Nitrae-dioxane of 5ml; Temperature adds catalyzer Tetrabutyl amonium bromide 1g after maintaining and stablizing, stop passing into nitrogen, react when being less than 30mgKOH/g to the acid number of system, stopper MEHQ 0.09g, cupric chloride 0.01g is added to system, and add vinylformic acid 18g, stopped reaction when reaction is less than 10mgKOH/g to system acid number, obtains product.Tested viscosity is 25000mPas (60 DEG C).
Embodiment 2
Take 100g bisphenol A type epoxy resin E51 in there-necked flask, (dimer is 80wt%, and tripolymer is 20wt% to add dimeracid, carboxyl-content is 0.35mol/100g) 109.3g, pass into drying nitrogen, be warming up to 100 DEG C, and add the Isosorbide-5-Nitrae-dioxane of 5ml; Temperature adds catalyzer Tetrabutyl amonium bromide 1.5g after maintaining and stablizing, stop passing into nitrogen, react when being less than 30mgKOH/g to the acid number of system, stopper MEHQ 0.05g, cupric chloride 0.005g is added to system, and add vinylformic acid 9.18g, stopped reaction when reaction is less than 10mgKOH/g to system acid number, obtains product.Tested viscosity is 20000mPas (60 DEG C).
Embodiment 3
Take 100g bisphenol A type epoxy resin E51 in there-necked flask, (dimer is 95wt%, and tripolymer is 5wt% to add dimeracid, carboxyl-content is 0.35mol/100g) 71.4g, pass into drying nitrogen, be warming up to 105 DEG C, and add 5ml1,4-dioxane; Temperature adds catalyzer Tetrabutyl amonium bromide 1g after maintaining and stablizing, stop passing into nitrogen, react when being less than 30mgKOH/g to the acid number of system, stopper MEHQ 0.09g, cupric chloride 0.01g is added to system, and add vinylformic acid 18g, stopped reaction when reaction is less than 10mgKOH/g to system acid number, obtains product.Tested viscosity is 14000mPas.
Embodiment 4
Take 100g bisphenol A type epoxy resin E51 in there-necked flask, (dimer is 95wt%, and tripolymer is 5wt% to add dimeracid, carboxyl-content is 0.35mol/100g) 109.4g, pass into drying nitrogen, be warming up to 105 DEG C, and add the Isosorbide-5-Nitrae-dioxane of 5ml; Temperature adds catalyzer Tetrabutyl amonium bromide 1.5g after maintaining and stablizing, stop passing into nitrogen, react when being less than 30mgKOH/g to the acid number of system, stopper MEHQ 0.05g, cupric chloride 0.005g is added to system, and add vinylformic acid 9.18g, stopped reaction when reaction is less than 10mgKOH/g to system acid number, obtains product.Tested viscosity is 12000mPas.Embodiment 5
Take 100g bisphenol A type epoxy resin E44 in there-necked flask, (dimer is 80wt%, and tripolymer is 20wt% to add dimeracid, carboxyl-content is 0.35mol/100g) 62.9g, pass into drying nitrogen, be warming up to 105 DEG C, and add the Isosorbide-5-Nitrae-dioxane of 5ml; Temperature adds catalyzer Tetrabutyl amonium bromide 0.8g after maintaining and stablizing, stop passing into nitrogen, react when being less than 30mgKOH/g to the acid number of system, stopper MEHQ 0.09g, cupric chloride 0.01g is added to system, and add vinylformic acid 18g, stopped reaction when reaction is less than 10mgKOH/g to system acid number, obtains product.Tested viscosity is 35000mPas.
Embodiment 6
Take 100g bisphenol A type epoxy resin E44 in there-necked flask, (dimer is 80wt%, and tripolymer is 20wt% to add dimeracid, carboxyl-content is 0.35mol/100g) 94.2g, pass into drying nitrogen, be warming up to 110 DEG C, and add 5ml1,4-dioxane; Temperature adds catalyzer Tetrabutyl amonium bromide 1.3g after maintaining and stablizing, stop passing into nitrogen, react when being less than 30mgKOH/g to the acid number of system, stopper MEHQ 0.05g, cupric chloride 0.005g is added to system, and add vinylformic acid 9.18g, stopped reaction when reaction is less than 10mgKOH/g to system acid number, obtains product.Tested viscosity is 30000mPas.
Embodiment 7
Take 100g bisphenol A type epoxy resin E44 in there-necked flask, (dimer is 95wt%, and tripolymer is 5wt% to add dimeracid, carboxyl-content is 0.35mol/100g) 62.9g, pass into drying nitrogen, be warming up to 110 DEG C, and add the Isosorbide-5-Nitrae-dioxane of 5ml; Temperature adds catalyzer Tetrabutyl amonium bromide 1g after maintaining and stablizing, stop passing into nitrogen, react when being less than 30mgKOH/g to the acid number of system, stopper MEHQ 0.09g, cupric chloride 0.01g is added to system, and add vinylformic acid 18g, stopped reaction when reaction is less than 10mgKOH/g to system acid number, obtains product.Tested viscosity is 32000mPas.
Embodiment 8
Take 100g bisphenol A type epoxy resin E44 in there-necked flask, (dimer is 95wt%, and tripolymer is 5wt% to add dimeracid, carboxyl-content is 0.35mol/100g) 94.2g, pass into drying nitrogen, be warming up to 100 DEG C, and add the Isosorbide-5-Nitrae-dioxane of 5ml; Temperature adds catalyzer Tetrabutyl amonium bromide 1.2g after maintaining and stablizing, stop passing into nitrogen, react when being less than 30mgKOH/g to the acid number of system, stopper MEHQ 0.05g, cupric chloride 0.005g is added to system, and add vinylformic acid 9.18g, stopped reaction when reaction is less than 10mgKOH/g to system acid number, obtains product.Tested viscosity is 28000mPas.
Claims (8)
1. a dimer acid modified epoxy resin, is characterized in that, the structural formula of described epoxy resin is:
。
2. prepare a method for epoxy resin dimer acid modified as claimed in claim 1, it is characterized in that, described method comprises the steps:
(1) take epoxy resin in there-necked flask, add dimeracid, pass into drying nitrogen, be warming up to 100 DEG C-110 DEG C, and add 2wt%1,4-dioxane;
(2) temperature maintain stable after, add catalyzer Tetrabutyl amonium bromide, stop passing into nitrogen, the acid number reacted to system is less than 30mgKOH/g;
(3) add stopper to system, and add acrylic or methacrylic acid, react stopped reaction when being less than 10mgKOH/g to system acid number, obtain product.
3. a kind of method preparing dimer acid modified epoxy resin according to claim 2, is characterized in that, described epoxy resin can be bisphenol A type epoxy resin E51 or bisphenol A type epoxy resin E44.
4. a kind of method preparing dimer acid modified epoxy resin according to claim 2, is characterized in that, in described dimeracid, dimer is 80wt%, and tripolymer is 20wt%, and carboxyl-content is 0.35mol/100g.
5. a kind of method preparing dimer acid modified epoxy resin according to claim 2, is characterized in that, in described dimeracid, dimer is 95wt%, and tripolymer is 5wt%, and carboxyl-content is 0.35mol/100g.
6. a kind of method preparing dimer acid modified epoxy resin according to claim 2, is characterized in that, the mol ratio of epoxy group(ing) and carboxyl is 1.05:1; Its epoxy group is provided by epoxy resin, and carboxyl is provided by dimeracid and acrylic or methacrylic acid; The carboxyl mol ratio that dimeracid and acrylic or methacrylic acid provide is 1-4:1.
7. a kind of method preparing dimer acid modified epoxy resin according to claim 2, is characterized in that, described stopper comprises relative to the acrylic or methacrylic acid MEHQ of 0.5wt% and the cupric chloride of 0.1wt%.
8. a kind of method preparing dimer acid modified epoxy resin according to claim 2, is characterized in that, catalyzer is Tetrabutyl amonium bromide, and add-on is the 0.5wt%-1wt% of step (2) system.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105969061A (en) * | 2016-06-17 | 2016-09-28 | 安庆市虹泰新材料有限责任公司 | Method for preparing dimer acid/SiO2/epoxy resin composite paint |
| CN106010103A (en) * | 2016-06-17 | 2016-10-12 | 安庆市虹泰新材料有限责任公司 | Preparation method of dimer acid and SiO2 nanoparticle modified epoxy resin paint |
| CN106118379A (en) * | 2016-06-17 | 2016-11-16 | 安庆市虹泰新材料有限责任公司 | A kind of dimeric dibasic acid/SiO2the preparation method of/epoxy resin ternary coating |
| CN106188496A (en) * | 2016-07-16 | 2016-12-07 | 北京化工大学 | A kind of dimer acid modified epoxy acrylate photopolymerization resin emulsion and preparation method thereof |
| CN111153793A (en) * | 2019-11-21 | 2020-05-15 | 池州瑞亚特新材料有限公司 | Toughening agent and preparation and use methods thereof |
| CN111647136A (en) * | 2020-06-19 | 2020-09-11 | 合肥福纳科技有限公司 | Resin packaging material and preparation method of QLED device |
| CN112538310A (en) * | 2020-12-10 | 2021-03-23 | 中电保力（北京）科技有限公司 | Flexible epoxy acrylate UV curing coating and application thereof in cable joint |
| KR102355781B1 (en) * | 2020-09-25 | 2022-02-07 | (주)엘프스 | self-assembled conductive bonding compound for LED chip bonding having excellent self-assembly, LED chip-circuit board bonding module comprising the same and manufacturing method thereof |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105969061A (en) * | 2016-06-17 | 2016-09-28 | 安庆市虹泰新材料有限责任公司 | Method for preparing dimer acid/SiO2/epoxy resin composite paint |
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| CN106118379A (en) * | 2016-06-17 | 2016-11-16 | 安庆市虹泰新材料有限责任公司 | A kind of dimeric dibasic acid/SiO2the preparation method of/epoxy resin ternary coating |
| CN106188496A (en) * | 2016-07-16 | 2016-12-07 | 北京化工大学 | A kind of dimer acid modified epoxy acrylate photopolymerization resin emulsion and preparation method thereof |
| CN111153793A (en) * | 2019-11-21 | 2020-05-15 | 池州瑞亚特新材料有限公司 | Toughening agent and preparation and use methods thereof |
| CN111153793B (en) * | 2019-11-21 | 2022-08-30 | 重庆集凯科技服务有限公司 | Toughening agent and preparation and use methods thereof |
| CN111647136A (en) * | 2020-06-19 | 2020-09-11 | 合肥福纳科技有限公司 | Resin packaging material and preparation method of QLED device |
| CN111647136B (en) * | 2020-06-19 | 2023-10-27 | 合肥福纳科技有限公司 | Resin packaging material and preparation method of QLED device |
| KR102355781B1 (en) * | 2020-09-25 | 2022-02-07 | (주)엘프스 | self-assembled conductive bonding compound for LED chip bonding having excellent self-assembly, LED chip-circuit board bonding module comprising the same and manufacturing method thereof |
| CN112538310A (en) * | 2020-12-10 | 2021-03-23 | 中电保力（北京）科技有限公司 | Flexible epoxy acrylate UV curing coating and application thereof in cable joint |
| CN112538310B (en) * | 2020-12-10 | 2022-03-15 | 中电保力（北京）科技有限公司 | Flexible epoxy acrylate UV curing coating and application thereof in cable joint |
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Application publication date: 20160323 |