CN104479107A - Elastic epoxy resin pavement material prepared from cardanolpolycyclic carbonate and preparation method of elastic epoxy resin pavement material - Google Patents
Elastic epoxy resin pavement material prepared from cardanolpolycyclic carbonate and preparation method of elastic epoxy resin pavement material Download PDFInfo
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- CN104479107A CN104479107A CN201410817332.9A CN201410817332A CN104479107A CN 104479107 A CN104479107 A CN 104479107A CN 201410817332 A CN201410817332 A CN 201410817332A CN 104479107 A CN104479107 A CN 104479107A
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Abstract
The invention provides an elastic epoxy resin pavement material prepared from cardanolpolycyclic carbonate and a preparation method of the elastic epoxy resin pavement material. Apreparation method of the cardanolpolycyclic carbonate comprises the following steps: cardanolglycidyl ether is oxidized with existence of m-chloroperoxybenzoic acid to generateepoxidizedcardanolglycidyl ether; and epoxidizedcardanolglycidyl ether and carbon dioxide react under catalysis of quaternary ammonium salt to generate cardanolpolycyclic carbonate. Further, 30-70 parts of cardanolpolycyclic carbonate, 30-60 parts of epoxy resin and 19-40 parts of anamine curing agent are stirred and mixed uniformly, bubbles are removed, and the mixture is cured for 24-168 h at the temperature of 25-80 DEG C to obtain the elastic epoxy resin pavement material. The tensile elongation at break of the elastic epoxy resin pavement material can reach 90%, the strength can reach 20 MPa simultaneously, and the elastic epoxy resin pavement material is a polymer pavement paving resin and curing agent system with high strength, high toughness and ultra-thin paving capacity.
Description
Technical field
The present invention relates to a kind of preparation method of elastic epoxy resin ground surface material, particularly relate to the preparation method of the polynary cyclic carbonate-modified epoxy resin pavement material of a kind of cardanol.
Background technology
In recent years, highway communication particularly high-grade highway and bridge construction flourish, using character and the function of the development road pavement of highway are had higher requirement.The use properties of the road pavement such as the design of the suitability of ground surface material, quality, composition and construction technology plays conclusive effect.Road surface can be divided into by the difference according to used ground surface material: soil, stone road surface, bituminous pavement and cement pavement.Soil stone road surface is the most original Expressway Pavement Material.China produces the aboundresources of cement, and cement concrete pavement has again the advantages such as bearing capacity is large, maintenance costs is few, the life-span is long, driving fuel-economizing, therefore cement concrete pavement becomes one of main road surface types of China.But cement concrete pavement rigidity is too large, cannot be applied to mating formation of Steel Bridge Deck, difficult after destroying repairing of bearing a heavy burden.Bituminous pavement is through long-term development, and its kind, making technique, use properties are constantly expanded and improved, and has become the main pavement structure in current world high-grade highway.The reason that bituminous pavement can occupy dominant position is that this kind of road surface has lot of advantages, as: surfacing, drive a vehicle comfortable, noise is little, has well damping, old asphalt mixture reproducible utilization etc.Although bituminous pavement has above-mentioned advantage, if material composition, construction technology are improper, and be subject to the effect of various factors, bituminous pavement top just there will be the bad phenomenon such as hot mastication, cold cracking, poor durability.
Because bituminous material defect inherently still exists, i.e. oxidizable and ultraviolet degraded, water tolerance, sliding resistance and poor durability, high temperature anti-rut behavior and low temperature elasticity resistance to cleavage are always the problem being mutually difficult to balance, after causing Large Span Bridges to build up soon, namely bridge deck pavement enters the repairing period of safeguarding.Along with increasing sharply of the volume of traffic and heavy goods vehicles, particularly overloading is serious in recent years, the destruction situation making deck paving is more and more serious, and after having bridge quite a lot to be open to traffic soon, deck paving just having occurred crack, gather around bag in various degree, rut, fragmentation, the disease such as come off.Therefore, deck paving becomes a gordian technique of restriction big-span steel bridge construction and development.For the deck paving of the large Large Span Bridges of the volume of traffic, safeguard more difficult, once destroy, just must keep in repair, cause traffic jam, thus cause the loss of economic benefit difficult to the appraisal and social benefit.
In international traffic industry, polymer materials is successfully widely used in road surface and deck paving.Have a lot of excellent character, the most outstanding feature is: can carry out superthin layer and mat formation, total thickness is 0.6-2cm only, easy construction, good weatherability, long service life.For the asphalt that pavement thickness must reach more than 8cm, polymer thin pave-load layer can alleviate the deadweight of pave-load layer 70%, for some very high built old bridges that bear a heavy burden itself, there is special significance, make bridge more more stable and stronger, the of ac grown with each passing day can be adapted to, thus extend the work-ing life of bed rearrangement bridge.Particularly, can normal temperature pavement construction, avoid conventional pitch class material at high temperature paving process to produce the infringement of thermal stresses for steel bridge construction.Do not need special preparation of construction, require lower for workman's state of the art.Research proves, the shock-resistant and wear resistant of polymer materials is the highest, is about steel iron type materials and cement concrete material 5 ~ 20 times.Polymkeric substance is by small molecule monomer by polyreaction, forms chemical bond-linking and is connected into three-dimensional crosslinked network structure.By the proprietary design that polymeric synthesizes, by the advantage of formed polymkeric substance modified monomer separately, the novel pavement pavement material of excellent properties can be formed.
Epoxide resin material is high owing to having rigidity, the feature that good heat resistance, shrinking percentage are low and adhesiveproperties is excellent, adds that output is high, cheap outward, epoxide resin material is become and is best suited for one of thermoset copolymer material of road surface and deck paving.But the texture material after the solidification of traditional pure epoxy resin is crisp, toughness and poor flexibility, be a difficult problem for synthesizing polymeric material subject, be also the focus that domestic and international polymeric material scholar researches and develops for many years always.
Cardanol unit loop carbonic ether has had patent to relate at present.Chinese patent (CN103265523A) discloses a kind of cardanol cyclic carbonate ester and quaternary ammonium salt derivative thereof and preparation method, and the method is with cardanol glycidyl ether and CO
2reactive Synthesis cardanol one membered ring carbonate under quaternary ammonium salt catalyst effect, and with it for the cardanol quaternary ammonium salt derivative of raw material preparation containing carbamate groups.Can only there is addition reaction with an amino in this cardanol one membered ring carbonate, cannot carry out crosslinking reaction.
Summary of the invention
The problem of crosslinking reaction cannot be carried out in order to solve prior art cardanol one membered ring carbonate, the invention discloses elastic epoxy resin ground surface material prepared by the polynary cyclic carbonate ester of a kind of cardanol and preparation method thereof, polynary for cardanol cyclic carbonate ester is introduced epoxy-resin systems, develop a kind of tension fracture elongation rate and can reach 90%, intensity can reach polymkeric substance paving resin and the curative systems of 20MPa simultaneously.
Technical scheme: elastic epoxy resin ground surface material prepared by the polynary cyclic carbonate ester of a kind of cardanol, raw material composition is counted by mass parts:
The polynary cyclic carbonate ester of cardanol 30 ~ 70 parts;
Epoxy resin 30 ~ 60 parts;
Amine curing agent 19 ~ 40 parts;
Wherein, the polynary cyclic carbonate ester of described cardanol is that cardanol glycidyl ether is oxidized generation epoxidation cardanol glycidyl ether under the existence of m-chloro-benzoic acid peroxide, then, epoxidation cardanol glycidyl ether and carbonic acid gas are obtained by reacting the polynary cyclic carbonate ester of cardanol under the catalysis of quaternary ammonium salt.Above-mentioned epoxy resin can be bisphenol A epoxide resin, cycloaliphatic epoxy resin a kind of or several mixture wherein.
Described epoxy resin is a kind of or several mixture in bisphenol A epoxide resin, cycloaliphatic epoxy resin.
Described amine curing agent is a kind of or several mixture in aliphatic amide, polyetheramine, aliphatic cyclic amine.
Described quaternary ammonium salt is any one in Tetrabutyl amonium bromide, benzyltriethylammoinium chloride or tetrabutylammonium chloride.
The preparation method of elastic epoxy resin ground surface material prepared by the polynary cyclic carbonate ester of described cardanol, polynary for cardanol cyclic carbonate ester, epoxy resin and amine curing agent are uniformly mixed, remove bubble, 25-80 DEG C of solidification obtained elastic epoxy resin ground surface material after 24-168 hour.
Beneficial effect:
1. after cardanol is prepared into cardanol glycidyl ether by the present invention, with superoxide, the double bond on cardanol alkyl segment is oxidized to epoxy group(ing) again, then the polynary cyclic carbonate ester of cardanol is prepared into, introduce epoxy-resin systems, thus improve the snappiness of system cured article, reach the performance requriements of deck paving resin.Compared with prior art cardanol one membered ring carbonate, the polynary cyclic carbonate ester of cardanol has the advantage that can be cross-linked, and can form linear or space network polymer material, can give epoxy-resin systems high strength and high tenacity with polynary amine curing agent.
2. compared with the paving material formed with prior art, this elastic epoxy resin ground surface material that the present invention provides, there is higher modulus, intensity, tension set and erosion resistance, snappiness is good, can ultra-thinly mat formation, if be applied to road surface particularly Steel Bridge Deck, can greatly alleviate pave-load layer weight, thus can save bridge construction cost and cost of mating formation.
Accompanying drawing explanation
Fig. 1 is the infrared spectra of the polynary cyclic carbonate ester of cardanol.
Embodiment
Following examples further illustrate content of the present invention, but should not be construed as limitation of the present invention.Without departing from the spirit and substance of the case in the present invention, the amendment do the inventive method, step or condition and replacement, all belong to scope of the present invention.
If do not specialize, the conventional means that technique means used in embodiment is well known to those skilled in the art.
Reagent used in embodiment: epoxy resin 128 (South Asia resin processing plant), cardanol glycidyl ether (according to document " study on the synthesis of n-octyl glycidyl ether, Jilin Institute of Chemical Technology journal; 20 (4); 2003,7-8. " preparation)
M-chloro-benzoic acid peroxide (Aladdin reagent), carbonic acid gas (55 institute), benzyltriethylammoinium chloride (Aladdin reagent).
Below be mass parts.
Embodiment 1
1mol cardanol glycidyl ether is oxidized under the existence of 1mol m-chloro-benzoic acid peroxide and generates epoxidation cardanol glycidyl ether.Epoxidation cardanol glycidyl ether and carbonic acid gas are under the catalysis of Tetrabutyl amonium bromide, and in reactor, 120 DEG C of reactions obtain the polynary cyclic carbonate ester of cardanol for 2 hours.Because the most composition of cardanol is all with the side chain of at least one double bond, the molecular formula of the polynary cyclic carbonate ester of this cardanol can be expressed as:
By above-mentioned cardanol cyclic carbonate ester 70 parts, epoxy resin 30 parts, isophorone diamine 32 parts, is uniformly mixed, removes bubble, and 25 DEG C of solidifications obtained elastic epoxy resin ground surface material after 168 hours.
Embodiment 2
1mol cardanol glycidyl ether is oxidized under the existence of 1mol m-chloro-benzoic acid peroxide and generates epoxidation cardanol glycidyl ether.Epoxidation cardanol glycidyl ether and carbonic acid gas under the catalysis of tetrabutylammonium chloride in a kettle. 120 DEG C react and within 2 hours, obtain the polynary cyclic carbonate ester of cardanol.
By above-mentioned cardanol cyclic carbonate ester 40 parts, epoxy resin 60 parts, hexanediamine 19 parts, is uniformly mixed, removes bubble, and 80 DEG C of solidifications obtained elastic epoxy resin ground surface material after 24 hours.
Embodiment 3
1mol cardanol glycidyl ether is oxidized under the existence of 1mol m-chloro-benzoic acid peroxide and generates epoxidation cardanol glycidyl ether.Epoxidation cardanol glycidyl ether and carbonic acid gas under the catalysis of benzyltriethylammoinium chloride in a kettle. 120 DEG C react and within 2 hours, obtain the polynary cyclic carbonate ester of cardanol.
By above-mentioned cardanol cyclic carbonate ester 50 parts, epoxy resin 50 parts, polyetheramine (D230) 40 parts, is uniformly mixed, removes bubble, and 60 DEG C of solidifications obtained elastic epoxy resin ground surface material after 72 hours.
Embodiment 4
1mol cardanol glycidyl ether is oxidized under the existence of 1mol m-chloro-benzoic acid peroxide and generates epoxidation cardanol glycidyl ether.Epoxidation cardanol glycidyl ether and carbonic acid gas under the catalysis of benzyltriethylammoinium chloride in a kettle. 120 DEG C react and within 2 hours, obtain the polynary cyclic carbonate ester of cardanol.
By above-mentioned cardanol cyclic carbonate ester 50 parts, epoxy resin 50 parts, hexanediamine 20 parts, polyetheramine (D230) 20 parts, is uniformly mixed, removes bubble, and 40 DEG C of solidifications obtained elastic epoxy resin ground surface material after 120 hours.
Embodiment 5
By the elastic epoxy resin ground surface material obtained in embodiment 1-4, the test of tensile strength, tensile modulus, elongation at break and ultimate compression strength is carried out according to GB/T 2567-2008, the test of shock strength is carried out according to GB/T 2567-2008, the test of bonding is just being drawn according to GB/T 6329-1996, carry out the test of steel-steel shearing resistance according to GB/T 7124-2008, carry out the test of shore hardness according to GB/T 22374-2008.Test result is as shown in table 1 below:
The mechanical experimental results of the elastic epoxy resin ground surface material that table 1 embodiment 1-4 obtains
Claims (5)
1. the elastic epoxy resin ground surface material prepared of the polynary cyclic carbonate ester of cardanol, is characterized in that, raw material composition is counted by mass parts:
The polynary cyclic carbonate ester of cardanol 30 ~ 70 parts;
Epoxy resin 30 ~ 60 parts;
Amine curing agent 19 ~ 40 parts;
Wherein, the polynary cyclic carbonate ester of described cardanol is that cardanol glycidyl ether is oxidized generation epoxidation cardanol glycidyl ether under the existence of m-chloro-benzoic acid peroxide, then, epoxidation cardanol glycidyl ether and carbonic acid gas are obtained by reacting the polynary cyclic carbonate ester of cardanol under the catalysis of quaternary ammonium salt.
2. the elastic epoxy resin ground surface material prepared of the polynary cyclic carbonate ester of cardanol as claimed in claim 1, it is characterized in that, described epoxy resin is a kind of or several mixture in bisphenol A epoxide resin, cycloaliphatic epoxy resin.
3. the elastic epoxy resin ground surface material prepared of the polynary cyclic carbonate ester of cardanol as claimed in claim 1, it is characterized in that, described amine curing agent is a kind of or several mixture in aliphatic amide, polyetheramine, aliphatic cyclic amine.
4. the elastic epoxy resin ground surface material prepared of the polynary cyclic carbonate ester of cardanol as claimed in claim 1, it is characterized in that, described quaternary ammonium salt is any one in Tetrabutyl amonium bromide, benzyltriethylammoinium chloride or tetrabutylammonium chloride.
5. the preparation method of elastic epoxy resin ground surface material for preparing of the arbitrary described polynary cyclic carbonate ester of cardanol of claim 1 ~ 4, it is characterized in that, polynary for cardanol cyclic carbonate ester, epoxy resin and amine curing agent are uniformly mixed, remove bubble, 25-80 DEG C of solidification obtained elastic epoxy resin ground surface material after 24-168 hour.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109468024A (en) * | 2018-11-21 | 2019-03-15 | 重庆市智翔铺道技术工程有限公司 | Wear-resisting pouring asphalt mixture terrace covering material and preparation method thereof |
| CN110670870A (en) * | 2019-10-14 | 2020-01-10 | 安徽豪鼎金属制品有限公司 | Wear-resisting type anti-corrosion scaffold fastener |
| CN110665734A (en) * | 2019-10-14 | 2020-01-10 | 安徽豪鼎金属制品有限公司 | Method for improving surface strength of metal plate and equipment adopting method |
| CN111005286A (en) * | 2019-11-28 | 2020-04-14 | 安徽省交通控股集团有限公司 | Whole car formula weighing equipment steel sheet mesa polymer of highway is compound to be paved structure |
| CN111269459A (en) * | 2020-02-13 | 2020-06-12 | 南京工业大学 | Epoxy cardanol ether ester plasticizer and preparation method and application thereof |
| CN112940349A (en) * | 2019-12-10 | 2021-06-11 | 中蓝晨光化工研究设计院有限公司 | Combined toughening agent containing five-membered cyclic carbonate group, preparation method and application of combined toughening agent in epoxy toughening |
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| CN103265523A (en) * | 2013-04-25 | 2013-08-28 | 中国林业科学研究院林产化学工业研究所 | Cardanol cyclic carbonate and its quaternary ammonium salt derivatives and preparation method thereof |
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| CN103265523A (en) * | 2013-04-25 | 2013-08-28 | 中国林业科学研究院林产化学工业研究所 | Cardanol cyclic carbonate and its quaternary ammonium salt derivatives and preparation method thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109468024A (en) * | 2018-11-21 | 2019-03-15 | 重庆市智翔铺道技术工程有限公司 | Wear-resisting pouring asphalt mixture terrace covering material and preparation method thereof |
| CN110670870A (en) * | 2019-10-14 | 2020-01-10 | 安徽豪鼎金属制品有限公司 | Wear-resisting type anti-corrosion scaffold fastener |
| CN110665734A (en) * | 2019-10-14 | 2020-01-10 | 安徽豪鼎金属制品有限公司 | Method for improving surface strength of metal plate and equipment adopting method |
| CN111005286A (en) * | 2019-11-28 | 2020-04-14 | 安徽省交通控股集团有限公司 | Whole car formula weighing equipment steel sheet mesa polymer of highway is compound to be paved structure |
| CN112940349A (en) * | 2019-12-10 | 2021-06-11 | 中蓝晨光化工研究设计院有限公司 | Combined toughening agent containing five-membered cyclic carbonate group, preparation method and application of combined toughening agent in epoxy toughening |
| CN112940349B (en) * | 2019-12-10 | 2022-08-12 | 中蓝晨光化工研究设计院有限公司 | Combined toughening agent containing five-membered cyclic carbonate group, preparation method and application of combined toughening agent in epoxy toughening |
| CN111269459A (en) * | 2020-02-13 | 2020-06-12 | 南京工业大学 | Epoxy cardanol ether ester plasticizer and preparation method and application thereof |
| CN111269459B (en) * | 2020-02-13 | 2021-04-20 | 南京工业大学 | Epoxy cardanol ether ester plasticizer and preparation method and application thereof |
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