CN105647389A - Method for preparing esters with rosin acrylic acid and GMA (glycidyl methacrylate) - Google Patents
Method for preparing esters with rosin acrylic acid and GMA (glycidyl methacrylate) Download PDFInfo
- Publication number
- CN105647389A CN105647389A CN201610138985.3A CN201610138985A CN105647389A CN 105647389 A CN105647389 A CN 105647389A CN 201610138985 A CN201610138985 A CN 201610138985A CN 105647389 A CN105647389 A CN 105647389A
- Authority
- CN
- China
- Prior art keywords
- rosin
- mass parts
- acrylic acid
- glycidyl methacrylate
- gma
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 32
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 32
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 32
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 title claims abstract description 24
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 9
- 150000002148 esters Chemical class 0.000 title abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000002253 acid Substances 0.000 claims abstract description 29
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 claims abstract description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 150000007942 carboxylates Chemical class 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 5
- 230000006837 decompression Effects 0.000 claims description 5
- 238000007599 discharging Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 abstract description 4
- 239000000178 monomer Substances 0.000 abstract description 3
- 238000004132 cross linking Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000007259 addition reaction Methods 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 238000001291 vacuum drying Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 5
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- -1 papermaking Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing esters with rosin acrylic acid and GMA (glycidyl methacrylate). The method includes: allowing addition reaction of rosin and acrylic acid to obtain a rosin acrylic acid addition product, dissolving the rosin acrylic acid addition product into methylbenzene, adding the glycidyl methacrylate, a catalyst triethylamine and a polymerization inhibitor hydroquinone, ultrasonically and uniformly dispersing, stirring at a constant-speed, starting a heating reaction, stopping the reaction when an acid value is below 10mgKOH/g, and carrying out reduced pressure distillation and vacuum drying to obtain the esters of the rosin acrylic acid and the GMA. The rosin which is a raw material is extensive in source, a synthesis method is simple, easiness in end point control, environment friendliness and benefits to further development and utilization of the rosin are realized, and the esters can serve as crosslinking monomers to be used for polymer synthesis and the like.
Description
Technical field
The present invention relates to the method that one utilizes rosin and crylic acid and glycidyl methacrylate (GMA) to prepare carboxylate.
Background technology
Colophonium is a kind of reproducible natural resources, has many excellent characteristics, such as anticorrosion, protection against the tide, insulation, bonding, emulsifying, softening etc., has a wide range of applications at numerous areas such as soap, papermaking, paint, rubber, binding agent, intermetallic composite coating. But Colophonium also exists again the easily shortcoming such as oxidized, color burn, crisp, the poor heat stability of qualitative change, thus having limited to its application. The active group conjugated double bond of rosin acid is modified, in the defect overcoming Colophonium in varying degrees, the range of application not only making Colophonium expands further, but also can increase the surcharge of Colophonium, therefore Colophonium is carried out deep processing and has important practical significance. Containing epoxy radicals, double bond functional group in glycidyl methacrylate (GMA) structure, carboxylate can be obtained with Colophonium and derivant generation ring-opening reaction thereof, and then it is introduced into the petroleum base monomer that polymer replacement is traditional, raising Colophonium deep processed product and added value is significant. After rosin esterification, not only can reducing its acid number, improve heat stability, it is also possible to strengthening the ability that Colophonium is acidproof, alkaline-resisting, thus significantly having widened the application of Colophonium. Therefore, esterification has become one of Abietyl modified most basic means, current various rosin ester product accounts for more than the 60% of Abietyl modified product, is widely used in the industries such as coating, cable, furniture, ink, rubber, adhesive, is considerable chemical products in national economy.
First Colophonium and acrylic acid are synthesized rosin and crylic acid addition product by Diels-Alder by the present invention, again rosin and crylic acid addition product, glycidyl methacrylate, catalyst of triethylamine, hydroquinone of polymerization retarder are dissolved in toluene, are prepared the carboxylate of rosin and crylic acid and glycidyl methacrylate by solvent method. This carboxylate, with two hydroxyls and two double bonds, can be widely applied to polymer and polymer microballoon field. Using toluene as solvent, adopt solvent method to prepare abietyl carboxylate and there is the advantages such as reaction temperature is low, simple to operate, safety, cost are low, esterification yield is high, product post processing is simple, Colophonium is introduced in carboxylate simultaneously, expand the use scope of Colophonium further, increase its use value.
Summary of the invention
It is an object of the invention to provide the method that one utilizes rosin and crylic acid and glycidyl methacrylate (GMA) to prepare carboxylate.
Concretely comprise the following steps:
(1) 100 mass parts Colophonium are added in the there-necked flask with agitating device, condensing tube, thermometer, nitrogen conduit and charging hopper; it is stirred under 400r/min after adding heat fusing; it is simultaneously directed nitrogen protection, heats after 230 DEG C, be slowly added dropwise 28.6 mass parts chemical pure acrylic acid; after within 1 hour, adding; continuing reaction 2 hours, cool the temperature to 200 DEG C of dischargings, after cooling, finely ground warm water repeatedly washes away unreacted acrylic acid; dry 72 hours, namely obtain rosin and crylic acid addition product.
(2) the rosin and crylic acid addition product of 100 mass parts is dissolved in 138 ~ 184 mass parts analytical pure toluene solvants, add the glycidyl methacrylate (GMA) that 38 ~ 84 mass parts mass percentage content are 97%, it is uniformly dispersed, add the hydroquinone of polymerization retarder of 0.1 ~ 1 mass parts of catalyst analytical pure triethylamine and 0.1 ~ 1 mass parts, mixing post-heating, reaction temperature is made to maintain 100 ~ 120 DEG C, react 3 ~ 6 hours, stopped reaction when acid number reaches below 10mgKOH/g, decompression is distilled off toluene, obtains the carboxylate of rosin and crylic acid and GMA.
The most outstanding feature of the present invention is that the carboxylate of preparation has two double bonds, it is possible to uses as cross-linking monomer, expands the use scope of Colophonium with Colophonium and GMA for raw material.
Detailed description of the invention
Embodiment 1:
(1) 100 mass parts Colophonium are added in the there-necked flask with agitating device, condensing tube, thermometer, nitrogen conduit and charging hopper; it is stirred under 400r/min after adding heat fusing; it is simultaneously directed nitrogen protection, heats after 230 DEG C, be slowly added dropwise 28.6 mass parts chemical pure acrylic acid; after within 1 hour, adding; continuing reaction 2 hours, cool the temperature to 200 DEG C of dischargings, after cooling, finely ground warm water repeatedly washes away unreacted acrylic acid; dry 72 hours, namely obtain rosin and crylic acid addition product.
(2) the rosin and crylic acid addition product of 100 mass parts is dissolved in 176 mass parts analytical pure toluene solvants, add the glycidyl methacrylate (GMA) that 76 mass parts mass percentage content are 97%, it is uniformly dispersed, add the hydroquinone of polymerization retarder of 0.7 mass parts of catalyst analytical pure triethylamine and 0.4 mass parts, mixing post-heating, reaction temperature is made to maintain 120 DEG C, react 4 hours, survey acid number is 1.2mgKOH/g, decompression is distilled off toluene, obtains the carboxylate of rosin and crylic acid and GMA.
Embodiment 2:
(1) 100 mass parts Colophonium are added in the there-necked flask with agitating device, condensing tube, thermometer, nitrogen conduit and charging hopper; it is stirred under 400r/min after adding heat fusing; it is simultaneously directed nitrogen protection, heats after 230 DEG C, be slowly added dropwise 28.6 mass parts chemical pure acrylic acid; after within 1 hour, adding; continuing reaction 2 hours, cool the temperature to 200 DEG C of dischargings, after cooling, finely ground warm water repeatedly washes away unreacted acrylic acid; dry 72 hours, namely obtain rosin and crylic acid addition product.
(2) the rosin and crylic acid addition product of 100 mass parts is dissolved in 184 mass parts analytical pure toluene solvants, add the glycidyl methacrylate (GMA) that 84 mass parts mass percentage content are 97%, it is uniformly dispersed, add the hydroquinone of polymerization retarder of 0.5 mass parts of catalyst analytical pure triethylamine and 0.4 mass parts, mixing post-heating, reaction temperature is made to maintain 120 DEG C, react 4 hours, survey acid number is 1.1mgKOH/g, decompression is distilled off toluene, obtains the carboxylate of rosin and crylic acid and GMA.
Embodiment 3:
(1) 100 mass parts Colophonium are added in the there-necked flask with agitating device, condensing tube, thermometer, nitrogen conduit and charging hopper; it is stirred under 400r/min after adding heat fusing; it is simultaneously directed nitrogen protection, heats after 230 DEG C, be slowly added dropwise 28.6 mass parts chemical pure acrylic acid; after within 1 hour, adding; continuing reaction 2 hours, cool the temperature to 200 DEG C of dischargings, after cooling, finely ground warm water repeatedly washes away unreacted acrylic acid; dry 72 hours, namely obtain rosin and crylic acid addition product.
(2) the rosin and crylic acid addition product of 100 mass parts is dissolved in 176 mass parts analytical pure toluene solvants, add the glycidyl methacrylate (GMA) that 76 mass parts mass percentage content are 97%, it is uniformly dispersed, add the hydroquinone of polymerization retarder of 0.5 mass parts of catalyst analytical pure triethylamine and 0.4 mass parts, mixing post-heating, reaction temperature is made to maintain 110 DEG C, react 6 hours, survey acid number is 6mgKOH/g, decompression is distilled off toluene, obtains the carboxylate of rosin and crylic acid and GMA.
Claims (1)
1. one kind utilizes the method that rosin and crylic acid and glycidyl methacrylate prepare carboxylate, it is characterised in that concretely comprise the following steps:
(1) 100 mass parts Colophonium are added in the there-necked flask with agitating device, condensing tube, thermometer, nitrogen conduit and charging hopper, it is stirred under 400r/min after adding heat fusing, it is simultaneously directed nitrogen protection, heats after 230 DEG C, be slowly added dropwise 28.6 mass parts acrylic acid, after within 1 hour, adding, continuing reaction 2 hours, cool the temperature to 200 DEG C of dischargings, after cooling, finely ground warm water repeatedly washes away unreacted acrylic acid, dry 72 hours, namely obtain rosin and crylic acid addition product;
(2) the rosin and crylic acid addition product of 100 mass parts is dissolved in 138 ~ 184 mass parts analytical pure toluene solvants, adding 38 ~ 84 mass parts mass percentage content is the glycidyl methacrylate of 97%, it is uniformly dispersed, add the hydroquinone of polymerization retarder of 0.1 ~ 1 mass parts of catalyst analytical pure triethylamine and 0.1 ~ 1 mass parts, mixing post-heating, reaction temperature is made to maintain 100 ~ 120 DEG C, react 3 ~ 6 hours, stopped reaction when acid number reaches below 10mgKOH/g, decompression is distilled off toluene, obtain the carboxylate of rosin and crylic acid and glycidyl methacrylate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610138985.3A CN105647389A (en) | 2016-03-13 | 2016-03-13 | Method for preparing esters with rosin acrylic acid and GMA (glycidyl methacrylate) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610138985.3A CN105647389A (en) | 2016-03-13 | 2016-03-13 | Method for preparing esters with rosin acrylic acid and GMA (glycidyl methacrylate) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105647389A true CN105647389A (en) | 2016-06-08 |
Family
ID=56492605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610138985.3A Pending CN105647389A (en) | 2016-03-13 | 2016-03-13 | Method for preparing esters with rosin acrylic acid and GMA (glycidyl methacrylate) |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105647389A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106496369A (en) * | 2016-11-04 | 2017-03-15 | 广东天安新材料股份有限公司 | A kind of crosslinking agent and its preparation method and application |
| CN108147778A (en) * | 2018-01-10 | 2018-06-12 | 和县明生环保材料有限责任公司 | A kind of light high-strength heat preservation hollow brick and its preparation |
| CN109943234A (en) * | 2019-02-21 | 2019-06-28 | 广西藤县通轩立信化学有限公司 | A kind of epoxy group alkene and alkene ether modified rosin phenol resin |
| CN112279960A (en) * | 2020-10-28 | 2021-01-29 | 广西民族师范学院 | Preparation method of hydroxyl-containing polydehydroabietate microspheres |
| CN115926772A (en) * | 2022-12-08 | 2023-04-07 | 陕西科技大学 | Temperature-controllable trigger type rosin resin capsule gel breaker and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5825315A (en) * | 1981-08-06 | 1983-02-15 | Osaka Soda Co Ltd | Production of glycidyl (meth)acrylate/rosin adduct |
| CN1425729A (en) * | 2002-12-30 | 2003-06-25 | 中国科学院广州化学研究所 | Propylenyl pimaric acid diglycidic ester and its epoxy resin and their preparation |
| CN101544744A (en) * | 2009-04-17 | 2009-09-30 | 中国科学院广州化学研究所 | Acrylic acid rosin and epoxy resin prepolymer and preparation method thereof |
-
2016
- 2016-03-13 CN CN201610138985.3A patent/CN105647389A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5825315A (en) * | 1981-08-06 | 1983-02-15 | Osaka Soda Co Ltd | Production of glycidyl (meth)acrylate/rosin adduct |
| CN1425729A (en) * | 2002-12-30 | 2003-06-25 | 中国科学院广州化学研究所 | Propylenyl pimaric acid diglycidic ester and its epoxy resin and their preparation |
| CN101544744A (en) * | 2009-04-17 | 2009-09-30 | 中国科学院广州化学研究所 | Acrylic acid rosin and epoxy resin prepolymer and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| CAI-LI YU ET AL: "Preparation of polystyrene microspheres using rosin-acrylic acid diester as a cross-linking agent", 《INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH》 * |
| 任鹏等: "松香和甲基丙烯酸缩水甘油酯酯化反应研究", 《化学研究与应用》 * |
| 余彩莉等: "松香丙烯酸加成物与HEMA酯化及溴化反应研究", 《中国胶粘剂》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106496369A (en) * | 2016-11-04 | 2017-03-15 | 广东天安新材料股份有限公司 | A kind of crosslinking agent and its preparation method and application |
| CN108147778A (en) * | 2018-01-10 | 2018-06-12 | 和县明生环保材料有限责任公司 | A kind of light high-strength heat preservation hollow brick and its preparation |
| CN109943234A (en) * | 2019-02-21 | 2019-06-28 | 广西藤县通轩立信化学有限公司 | A kind of epoxy group alkene and alkene ether modified rosin phenol resin |
| CN112279960A (en) * | 2020-10-28 | 2021-01-29 | 广西民族师范学院 | Preparation method of hydroxyl-containing polydehydroabietate microspheres |
| CN115926772A (en) * | 2022-12-08 | 2023-04-07 | 陕西科技大学 | Temperature-controllable trigger type rosin resin capsule gel breaker and preparation method thereof |
| CN115926772B (en) * | 2022-12-08 | 2024-01-02 | 陕西科技大学 | Temperature-controllable trigger rosin resin capsule gel breaker and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105647389A (en) | Method for preparing esters with rosin acrylic acid and GMA (glycidyl methacrylate) | |
| Tremblay-Parrado et al. | Click chemistry for the synthesis of biobased polymers and networks derived from vegetable oils | |
| Lomège et al. | Fatty acid-based radically polymerizable monomers: from novel poly (meth) acrylates to cutting-edge properties | |
| Kim et al. | The development and comparison of bio-thermoset plastics from epoxidized plant oils | |
| Yang et al. | Novel renewable resource-based UV-curable copolymers derived from myrcene and tung oil: Preparation, characterization and properties | |
| Liang et al. | Synthesis and characterization of novel renewable tung oil-based UV-curable active monomers and bio-based copolymers | |
| Zhou et al. | Facile synthesis and characterization of urushiol analogues from tung oil via ultraviolet photocatalysis | |
| CN102659598A (en) | Method for preparing ester compound by colophony and glycidyl methacrylate | |
| Brocas et al. | Epoxidized rosin acids as co-precursors for epoxy resins | |
| Mustata et al. | Biobased epoxy matrix from diglycidyl ether of bisphenol A and epoxidized corn oil, cross-linked with Diels–Alder adduct of levopimaric acid with acrylic acid | |
| Alam et al. | Coatings derived from novel, soybean oil-based polymers produced using carbocationic polymerization | |
| Lu et al. | Crosslinkable poly (vinyl acetate) emulsions for wood adhesive | |
| CN101705044B (en) | Water-soluble ultraviolet light curing coating and method for preparing same | |
| Sahoo et al. | Synthesis and characterization of low viscous and highly acrylated epoxidized methyl ester based green adhesives derived from linseed oil | |
| CN101280056B (en) | Method for preparing C21dicarboxylic acid polyamide epoxy hardener from methyl eleostearate | |
| CN104927680A (en) | Fast-curing instant glue and preparation method thereof | |
| CN105646800A (en) | Method for preparing rosin-based hydroxylation polymer micro-spheres | |
| Wang et al. | Synthesis and characterization of a novel rosin-based monomer: free-radical polymerization and epoxy curing | |
| CN108640849A (en) | Preparation method of ultraviolet-curing terpene-based dendritic epoxy acrylate | |
| CN102838486A (en) | Ultraviolet light curing polyester acrylate and preparation method thereof | |
| Wu et al. | Development and evaluation of pressure sensitive adhesives from a fatty ester | |
| Fakhari et al. | Synthesis of new bio-based thermoset resin from palm oil | |
| CN105801406A (en) | Epoxidized soybean oil itaconate as well as preparation method and application thereof | |
| Yang et al. | Biobased Epoxies Derived from Myrcene and Plant Oil: Design and Properties of Their Cured Products | |
| CN104403515B (en) | The preparation method of attapulgite load photosensitizer and ultraviolet-curing paint |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160608 |
|
| RJ01 | Rejection of invention patent application after publication |