CN107298760A - A kind of preparation method of modified cashew nut shell oil PPG anacardol - Google Patents
A kind of preparation method of modified cashew nut shell oil PPG anacardol Download PDFInfo
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- CN107298760A CN107298760A CN201710397864.5A CN201710397864A CN107298760A CN 107298760 A CN107298760 A CN 107298760A CN 201710397864 A CN201710397864 A CN 201710397864A CN 107298760 A CN107298760 A CN 107298760A
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
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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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The present invention discloses a kind of preparation method of modified cashew nut shell oil PPG anacardol, instead of traditional phenol by cashew nut shell oil and is reacted；Reaction raw materials cashew nut shell oil is subjected to chloromethylation by add that chloromethylation reagents can be more thoroughly；Make it have higher reactivity；Obtained cashew nut oil modified alkyd resin can obtain cashew nut shell oil PPG as a kind of intermediate resin by hydroxylating, and viscosity is relatively low, and degree of functionality is higher.Also there is higher reactivity using oxalic acid as acidic catalyst, it is possible to increase reaction efficiency, and environmental protection.
Description
Technical field
Present method invention is related to organic high molecular compound preparing technical field, is related to a kind of modified cashew nut shell oil polyethers many
The preparation method of first alcohol anacardol.
Background technology
The main component of cashew nut shell oil is anacardol, both phenol hydroxyl containing rigid phenyl ring and high activity in its molecular structure
Base, again containing strong hydrophobic flexible aliphatic side chain, thus itself just has splendid corrosion resistance and fabulous mechanicalness
Energy.In addition, cashew nut shell oil derives from the cashew nut shell of Nantural non-toxic, belong to complete natural environmental-protective, green renewable resource.It is positive because
In this way, it is intended that cashew nut shell oil is incorporated into conventional urethane coating to improve its combination property particularly alkali resistance.
Cashew nut shell oil is successfully introduced into polyurethane coating systems by prior art, but still is come with some shortcomings, and is such as existed
In United States Patent (USP) 2005/0192423A1, its raw material is anacardol dilution（cardanol-depleted）Cashew nut shell oil is mixed
Thing, viscosity reaches 5000~20000cps at its 25 DEG C, and the PPG viscosity produced with it is also higher, very not
Beneficial to actual production and site operation, in Japan Patent JP48029530, introduce oxirane or expoxy propane reacted,
Its toxicity is larger, and oxirane is that gas is difficult to control at room temperature.Such as a kind of Publication No. CN103073689B cashew nut
Shell oil modified phenolic resin and with its preparation cashew nut shell oil PPG preparation method in, cashew nut shell oil PPG
Applied in polyurethane coating, it uses cooperatively as hydroxy-containing resin and isocyanate component and forms polyurethane coating systems,
It has corrosion resistance especially alkali resistance good, the features such as mechanical performance is excellent, but during the utilization of anacardol, exists anti-
The problem of answering active relatively low.
The content of the invention
It is an object of the invention to provide a kind of preparation method of modified cashew nut shell oil PPG anacardol, to solve
The problem of being proposed in above-mentioned background technology.
In order to solve the above-mentioned technical problem, the technical scheme is that：A kind of modified cashew nut shell oil PPG waist
The preparation method of fruit phenol, comprises the following steps：
1) 45-55 parts of cashew nut shell oil, 45-55 parts of alkene carbonic ester, 8-13 parts of oxalic acid and chlorination are first sequentially added into reactor
7-11 parts of mixing of aluminium, after 10 minutes, then 13-17 parts of the chloromethylation reagents of addition into reactor, carried out under 20 DEG C of environment anti-
Should, it is rear standby；
2) to step 1）6-9 parts of paraformaldehydes are added in the mixture of gained, is then maintained under 20 DEG C of environment and stirs 6 minutes,
Then heat up, control system temperature treats that paraformaldehyde is completely dissolved, obtain solution at 55~60 DEG C；
3) at normal atmospheric pressure, by step 2）The solution of gained is warming up to 70 DEG C of reaction 3h, and solution is warming up into 75~95 DEG C
Vacuum dehydration 3h, obtains cashew nut oil modified alkyd resin；
4) to step 3）In the cashew nut oil modified alkyd resin of gained, 7-12 parts of potassium hydroxide and 3-6 parts of propylene carbonates are added
Ester, is mixed, and 5~15h is reacted at 120~200 DEG C, is cooled down, and filtering, standing obtains cashew nut shell oil PPG.
Further, step 1）In each raw material reaction time be 6h.
Further, the chloromethylation reagents are ClCH2O (CH2) 3CH3 and (ClCH2O) 2 (CH2) 3.
Further, the alkene carbonic ester is one kind or two in ethylene carbonate, propene carbonate, butylene
Plant the mixing of the above.
Further, the phenolic hydroxyl group average functionality of the cashew nut shell oil is 2.5~3.0.
Further, the chloromethylation reagents are made up of paraformaldehyde with hydrochloric acid.
The technology of the present invention effect major embodiment is in the following areas：The present invention instead of traditional phenol by cashew nut shell oil and enter
Row reaction；Reaction raw materials cashew nut shell oil is subjected to chloromethylation by add that chloromethylation reagents can be more thoroughly；Have it
There is higher reactivity；Obtained cashew nut oil modified alkyd resin can pass through hydroxylating as a kind of intermediate resin
Reaction obtains cashew nut shell oil PPG, and viscosity is relatively low, and degree of functionality is higher.Also have using oxalic acid as acidic catalyst
There is higher reactivity, it is possible to increase reaction efficiency, and environmental protection.
Embodiment
The technical scheme in the embodiment of the present invention is clearly and completely described below, it is clear that described embodiment
Only a part of embodiment of the invention, rather than whole embodiments, based on the embodiment in the present invention, the common skill in this area
The every other embodiment that art personnel are obtained under the premise of creative work is not made, belongs to the model that the present invention is protected
Enclose.
Embodiment 1
A kind of preparation method of modified cashew nut shell oil PPG anacardol, comprises the following steps：
1）45 parts of cashew nut shell oil, 45 parts of alkene carbonic ester, the 7 parts of mixing of 8 parts of oxalic acid and aluminium chloride are first sequentially added into reactor,
After 10 minutes, then 13 parts of the chloromethylation reagents of addition into reactor, reacted under 20 DEG C of environment, it is rear standby；
2）To step 1）6 parts of paraformaldehydes are added in the mixture of gained, stirring 6 minutes under 20 DEG C of environment are then maintained at, so
After heat up, control system temperature treats that paraformaldehyde is completely dissolved, obtains solution at 55 DEG C；
3) at normal atmospheric pressure, by step 2）The solution of gained is warming up to 70 DEG C of reaction 3h, and solution is warming up into 75 DEG C of vacuum
3h is dehydrated, cashew nut oil modified alkyd resin is obtained；
4) to step 3）In the cashew nut oil modified alkyd resin of gained, 7 parts of potassium hydroxide and 3 parts of propene carbonates are added, are mixed
It is even, 5h is reacted at 120 DEG C, is cooled down, filtering, standing obtains cashew nut shell oil PPG.
Step 1）In each raw material reaction time be 6h.
The chloromethylation reagents are ClCH2O (CH2) 3CH3 and (ClCH2O) 2 (CH2) 3.
The alkene carbonic ester is more than one or both of ethylene carbonate, propene carbonate, butylene
Mixing.
The phenolic hydroxyl group average functionality of the cashew nut shell oil is 2.5.
The chloromethylation reagents are made up of paraformaldehyde with hydrochloric acid.
Embodiment 2
A kind of preparation method of modified cashew nut shell oil PPG anacardol, comprises the following steps：
1）11 parts of 55 parts of cashew nut shell oil, 55 parts of alkene carbonic ester, 13 parts of oxalic acid and aluminium chloride is first sequentially added into reactor to mix
Close, after 10 minutes, then 17 parts of the chloromethylation reagents of addition into reactor, reacted under 20 DEG C of environment, it is rear standby；
2）To step 1）9 parts of paraformaldehydes are added in the mixture of gained, stirring 6 minutes under 20 DEG C of environment are then maintained at, so
After heat up, control system temperature treats that paraformaldehyde is completely dissolved, obtains solution at 60 DEG C；
3) at normal atmospheric pressure, by step 2）The solution of gained is warming up to 70 DEG C of reaction 3h, and solution is warming up into 95 DEG C of vacuum
3h is dehydrated, cashew nut oil modified alkyd resin is obtained；
4) to step 3）In the cashew nut oil modified alkyd resin of gained, 12 parts of potassium hydroxide and 6 parts of propene carbonates are added, are mixed
It is even, 15h is reacted at 200 DEG C, is cooled down, filtering, standing obtains cashew nut shell oil PPG.
Step 1）In each raw material reaction time be 6h.
The chloromethylation reagents are ClCH2O (CH2) 3CH3 and (ClCH2O) 2 (CH2) 3.
The alkene carbonic ester is more than one or both of ethylene carbonate, propene carbonate, butylene
Mixing.
The phenolic hydroxyl group average functionality of the cashew nut shell oil is 3.0.
The chloromethylation reagents are made up of paraformaldehyde with hydrochloric acid.
Embodiment 3
A kind of preparation method of modified cashew nut shell oil PPG anacardol, comprises the following steps：
1）9 parts of 50 parts of cashew nut shell oil, 50 parts of alkene carbonic ester, 10 parts of oxalic acid and aluminium chloride is first sequentially added into reactor to mix
Close, after 10 minutes, then 15 parts of the chloromethylation reagents of addition into reactor, reacted under 20 DEG C of environment, it is rear standby；
2）To step 1）7 parts of paraformaldehydes are added in the mixture of gained, stirring 6 minutes under 20 DEG C of environment are then maintained at, so
After heat up, control system temperature treats that paraformaldehyde is completely dissolved, obtains solution at 58 DEG C；
3) at normal atmospheric pressure, by step 2）The solution of gained is warming up to 70 DEG C of reaction 3h, and solution is warming up into 85 DEG C of vacuum
3h is dehydrated, cashew nut oil modified alkyd resin is obtained；
4) to step 3）In the cashew nut oil modified alkyd resin of gained, 9 parts of potassium hydroxide and 5 parts of propene carbonates are added, are mixed
It is even, 10h is reacted at 160 DEG C, is cooled down, filtering, standing obtains cashew nut shell oil PPG.
Step 1）In each raw material reaction time be 6h.
The chloromethylation reagents are ClCH2O (CH2) 3CH3 and (ClCH2O) 2 (CH2) 3.
The alkene carbonic ester is more than one or both of ethylene carbonate, propene carbonate, butylene
Mixing.
The phenolic hydroxyl group average functionality of the cashew nut shell oil is 2.8.
The chloromethylation reagents are made up of paraformaldehyde with hydrochloric acid.
The PPG of the present invention can be applied in polyurethane coating, and it is used as hydroxy-containing resin and isocyanate component
With the use of polyurethane coating systems are formed, it has corrosion resistance especially alkali resistance good, the features such as mechanical performance is excellent.
Experimental example 1：
Control group one：Conventional urethane coating；
Control group two：Imported polyurethane coating；
Experimental group：The polyurethane coating being configured to by cashew nut shell oil PPG anacardol made from the method for the present invention.
Test method：According to polyurethane water-proof paint GBT19250-2013, under equal execution conditions, three groups of machinery
Performance, acid resistance, workability carry out test and comparison.
3 groups of result of the test see the table below：
| Group | Alkali resistance | Mechanical performance | Workability |
| Control group one | Difference | Difference | Difference |
| Control group two | Typically | Typically | Typically |
| Experimental group | It is good | It is good | It is good |
By experiment, three groups of alkali resistance, mechanical performance and workability have significant difference.
Experimental example 2：
Control group one：Traditional anacardol；
Control group two：Import anacardol；
Experimental group：Pass through cashew nut shell oil PPG anacardol made from the method for the present invention.
Test method：Under equal conditions, the reactivity and viscosity to three groups of anacardol carry out test and comparison.
3 groups of result of the test see the table below：
| Group | Reactivity | Viscosity |
| Control group one | Difference | 3000cps@25℃ |
| Control group two | Typically | 2600cps@25℃ |
| Experimental group | It is good | 2400cps@25℃ |
By experiment, three groups of reactivity and viscosity have significant difference.
The technology of the present invention effect major embodiment is in the following areas：The present invention instead of traditional phenol by cashew nut shell oil and enter
Row reaction；Reaction raw materials cashew nut shell oil is subjected to chloromethylation by add that chloromethylation reagents can be more thoroughly；Have it
There is higher reactivity；Obtained cashew nut oil modified alkyd resin can pass through hydroxylating as a kind of intermediate resin
Reaction obtains cashew nut shell oil PPG, and viscosity is relatively low, and degree of functionality is higher.Also have using oxalic acid as acidic catalyst
There is higher reactivity, it is possible to increase reaction efficiency, and environmental protection.
Moreover, it will be appreciated that although the present specification is described in terms of embodiments, not each embodiment is only wrapped
Containing an independent technical scheme, this narrating mode of specification is only that for clarity, those skilled in the art should
Using specification as an entirety, the technical solutions in the various embodiments may also be suitably combined, forms those skilled in the art
It may be appreciated other embodiment.
Claims (6)
1. a kind of preparation method of modified cashew nut shell oil PPG anacardol, it is characterised in that comprise the following steps：
1）45-55 parts of cashew nut shell oil, 45-55 parts of alkene carbonic ester, 8-13 parts of oxalic acid and chlorination are first sequentially added into reactor
7-11 parts of mixing of aluminium, after 10 minutes, then 13-17 parts of the chloromethylation reagents of addition into reactor, carried out under 20 DEG C of environment anti-
Should, it is rear standby；
2) to step 1）6-9 parts of paraformaldehydes are added in the mixture of gained, is then maintained under 20 DEG C of environment and stirs 6 minutes,
Then heat up, control system temperature treats that paraformaldehyde is completely dissolved, obtain solution at 55~60 DEG C；
3) at normal atmospheric pressure, by step 2）The solution of gained is warming up to 70 DEG C of reaction 3h, and solution is warming up into 75~95 DEG C
Vacuum dehydration 3h, obtains cashew nut oil modified alkyd resin；
4) to step 3）In the cashew nut oil modified alkyd resin of gained, 7-12 parts of potassium hydroxide and 3-6 parts of propylene carbonates are added
Ester, is mixed, and 5~15h is reacted at 120~200 DEG C, is cooled down, and filtering, standing obtains cashew nut shell oil PPG.
2. preparation method according to claim 1, it is characterised in that step 1）In each raw material reaction time be 6h.
3. preparation method according to claim 1, it is characterised in that the chloromethylation reagents are ClCH2O (CH2)
3CH3 and (ClCH2O) 2 (CH2) 3.
4. preparation method according to claim 1, it is characterised in that the alkene carbonic ester is ethylene carbonate, carbonic acid
Mixing more than one or both of propylene, butylene.
5. preparation method according to claim 1, it is characterised in that the phenolic hydroxyl group average functionality of the cashew nut shell oil is
2.5~3.0.
6. preparation method according to claim 1, it is characterised in that the chloromethylation reagents are by paraformaldehyde and hydrochloric acid
Composition.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201710397864.5A CN107298760A (en) | 2017-05-31 | 2017-05-31 | A kind of preparation method of modified cashew nut shell oil PPG anacardol |
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| CN201710397864.5A CN107298760A (en) | 2017-05-31 | 2017-05-31 | A kind of preparation method of modified cashew nut shell oil PPG anacardol |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110105916A (en) * | 2019-05-05 | 2019-08-09 | 安徽省淮河制胶有限公司 | A kind of preparation method of water resistance gelatine |
| CN110982060A (en) * | 2019-12-24 | 2020-04-10 | 上海拓径新材料科技股份有限公司 | Amine-terminated polyether compound containing cardanol derivative, and preparation method and application thereof |
| CN116284720A (en) * | 2023-04-14 | 2023-06-23 | 大庆师范学院 | Cardanol-based polycarbonate demulsifier and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102702504A (en) * | 2011-10-09 | 2012-10-03 | 卡德莱化工(珠海)有限公司 | Plant oil polyether polyol prepared by using cashew shell oil as raw material and preparation method and application thereof |
| CN103012073A (en) * | 2012-12-27 | 2013-04-03 | 山东圣泉化工股份有限公司 | Preparation method of chloromethylated cardanol |
| CN103073689A (en) * | 2013-01-21 | 2013-05-01 | 卡德莱化工(珠海)有限公司 | Cashew nut shell oil-modified phenolic resin and preparation method for cashew nut shell oil polyether polyol prepared from same |
-
2017
- 2017-05-31 CN CN201710397864.5A patent/CN107298760A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102702504A (en) * | 2011-10-09 | 2012-10-03 | 卡德莱化工(珠海)有限公司 | Plant oil polyether polyol prepared by using cashew shell oil as raw material and preparation method and application thereof |
| CN103012073A (en) * | 2012-12-27 | 2013-04-03 | 山东圣泉化工股份有限公司 | Preparation method of chloromethylated cardanol |
| CN103073689A (en) * | 2013-01-21 | 2013-05-01 | 卡德莱化工(珠海)有限公司 | Cashew nut shell oil-modified phenolic resin and preparation method for cashew nut shell oil polyether polyol prepared from same |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110105916A (en) * | 2019-05-05 | 2019-08-09 | 安徽省淮河制胶有限公司 | A kind of preparation method of water resistance gelatine |
| CN110982060A (en) * | 2019-12-24 | 2020-04-10 | 上海拓径新材料科技股份有限公司 | Amine-terminated polyether compound containing cardanol derivative, and preparation method and application thereof |
| CN116284720A (en) * | 2023-04-14 | 2023-06-23 | 大庆师范学院 | Cardanol-based polycarbonate demulsifier and preparation method and application thereof |
| CN116284720B (en) * | 2023-04-14 | 2023-10-03 | 大庆师范学院 | Cardanol-based polycarbonate demulsifier and preparation method and application thereof |
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Application publication date: 20171027 |