CN103468182A - Preparation method of boron modified phenolic resin adhesive - Google Patents
Preparation method of boron modified phenolic resin adhesive Download PDFInfo
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- CN103468182A CN103468182A CN2013103773204A CN201310377320A CN103468182A CN 103468182 A CN103468182 A CN 103468182A CN 2013103773204 A CN2013103773204 A CN 2013103773204A CN 201310377320 A CN201310377320 A CN 201310377320A CN 103468182 A CN103468182 A CN 103468182A
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- modified phenolic
- phenolic resin
- boron modified
- sizing agent
- weight parts
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Abstract
The invention relates to a preparation method of a boron modified phenolic resin adhesive, which comprises the following steps of 1, synthesizing polyborosiloxane (PBSH), 2, synthesizing modified phenolic resin, and 3, preparing the boron modified phenolic resin adhesive. In the boron modified phenolic resin adhesive, the method for preparing PBSH is relatively mild in condition, simple to operate, green and environment-friendly, and has no harmful gas generation; obtained PBSH is excellent in high-temperature resistance, contains a great amount of terminated hydroxy, and can improve the high-temperature resistance and the bonding strength of the phenolic resin when serving as a modifying agent; and the feasible method is provided for preparing the high-temperature-resistant phenolic resin adhesive.
Description
Technical field
The invention belongs to chemical field, relate in particular to a kind of making method of utilizing polyborosiloxane and modified phenolic resins synthetic adhesive.
Background technology
The resol price is very low, raw material has easily been bought, production technique and production unit simple, become one of indispensable material of industrial sector, apply very extensive.Pure phenolic aldehyde resin thermal stability and high thermal resistance are not high enough, and people have carried out large quantity research to its modification, to improve its thermotolerance and cohesive strength.
Polyborosiloxane (PBS) has excellent resistance toheat.There are research and utilization boric acid and organosilicon preformed polymer to prepare polyborosiloxane, and use it for the modification of resol, resin carbon residue rate after modification significantly improves, but the cohesive force of the phenolic resin adhesive after modification does not obviously improve (Zhang Bin etc., polymer material science and engineering, 2008,152).There is research to introduce the Resorcinol structure in polyborosiloxane, obtain polyborosiloxane PBSH, the following technological line of main employing prepares PBSH at present: in nitrogen atmosphere, first by two halosilanes and boric acid, carry out bulk reaction, add afterwards Resorcinol solution to continue reaction, obtain PBSH(expense ease big, coatings industry .1991,3,8).There is following problem in above-mentioned route: wherein adopt halosilanes and acid reaction, generate the HCl gas that pungent odour is arranged, there is very high corrodibility.
Summary of the invention
The present invention has designed a kind of making method of boron modified phenolic resin sizing agent, and it is high temperature resistant altogether that its purpose is to provide, and the sizing agent of high bond strength, improves the preparation method of polyborosiloxane (PBSH) simultaneously, overcomes the problems of the prior art.
To achieve these goals, the present invention has adopted following scheme:
A kind of boron modified phenolic resin sizing agent comprises following steps:
Step 1: synthetic polyborosiloxane (PBSH);
Step 2: synthesis modification resol;
Step 3: prepare the boron modified phenolic resin sizing agent.
Described step 1 is that organo-siloxane and boric acid are joined in organic solvent, under the condition existed at catalyzer, in nitrogen atmosphere, progressively is warmed up to 200 ℃, reaction 1-5h from 90 ℃ in lower 3 hours; Then add polyphenol, reaction 4-10h, after water pump Depressor response 1.5～3h, obtain polyborosiloxane (PBSH);
Described step 2 is to get the Resorcinol of the methoxyl group parylene monomer of 20 weight parts, 20 weight parts and an acidic catalyst of 1.5 weight parts, react 1-4h under the condition of 125 ℃, after cooling down, add the basic catalyst of 1.5 weight parts, the organic solvent of 12 weight parts and the formaldehyde of 18 weight parts, dehydration reaction under the vacuum of 0.6KPa obtains modified phenolic resins after transparent;
Described step 3 is to get modified phenolic resins that the polyborosiloxane that makes in step 1 and step 2 make to mix by the mass ratio of 1-6:10, obtains the boron modified phenolic resin tackiness agent.
The described organo-siloxane of step 1: boric acid: the mol ratio of polyphenol is 1:1～2:0.25～1, and catalyst levels is 1 of monomer total mass～2 ‰.
The described organo-siloxane of step 1 is the mixture that phenyltrimethoxysila,e and methyltrimethoxy silane are made according to weight fraction 1:2.
The described solvent of step 1 is diethylene glycol dimethyl ether or dioxane.
The described catalyzer of step 1 is any one in tin protochloride, titanium tetrachloride, Indian red.
The described polyphenol of step 1 is a kind of or several mixing in pyrocatechol, Resorcinol, Resorcinol, Phloroglucinol, pyrogallol.
The tosic acid that the described an acidic catalyst of step 2 is 25wt%, the ammoniacal liquor that described basic catalyst is 20wt%, described organic solvent is vinylbenzene.
The mass ratio of the described polyborosiloxane of step 3 and modified phenolic resins is 2-5:10.
The making method of this boron modified phenolic resin sizing agent has following beneficial effect:
1, the present invention is by organo-siloxane and boric acid, polyphenol polycondensation, the synthetic polyborosiloxane that contains a large amount of terminal hydroxy group and have excellent heat resistance; After resol mixes, can improve its thermotolerance and bonding strength.
2, the present invention prepares polyborosiloxane method mild condition, simple to operate, without harmful gas generation, environmental protection, gained polyborosiloxane resistance to elevated temperatures excellence.
Embodiment
Below in conjunction with specific embodiment, the present invention will be further described:
Embodiment 1
Step 1: mixture and boric acid that phenyltrimethoxysila,e and methyltrimethoxy silane are made according to weight fraction 1:2 join in diethylene glycol dimethyl ether, under the condition existed at tin protochloride, progressively be warmed up to 200 ℃ from 90 ℃ in lower 3 hours of nitrogen atmosphere, continue reaction 5h; Then add Resorcinol, reaction 6h, after water pump Depressor response 2h, obtain polyborosiloxane (PBSH); Organo-siloxane: boric acid: the mol ratio of Resorcinol is 1:1:1, and catalyst levels is 1 ‰ of monomer total mass;
Step 2: the tosic acid of getting the 25wt% of the Resorcinol of methoxyl group parylene monomer, 20 weight parts of 20 weight parts and 1.5 weight parts, react 2h under the condition of 125 ℃, after cooling down, add the ammoniacal liquor of the 20wt% of 1.5 weight parts, the vinylbenzene of 12 weight parts and the formaldehyde of 18 weight parts, dehydration reaction under the vacuum of 0.6KPa obtains modified phenolic resins after transparent;
Step 3: get modified phenolic resins that the polyborosiloxane that makes in step 1 and step 2 make and mix by the mass ratio of 2:10, obtain the boron modified phenolic resin tackiness agent.
Embodiment 2
Step 1: mixture and boric acid that phenyltrimethoxysila,e and methyltrimethoxy silane are made according to weight fraction 1:2 join in dioxane, under the condition existed at tin protochloride, progressively be warmed up to 200 ℃ from 90 ℃ in lower 3 hours of nitrogen atmosphere, continue reaction 5h; Then add Resorcinol, reaction 6h, after water pump Depressor response 2h, obtain polyborosiloxane (PBSH); Organo-siloxane: boric acid: the mol ratio of Resorcinol is 1:1:1, and catalyst levels is 1 ‰ of monomer total mass;
Step 2: the tosic acid of getting the 25wt% of the Resorcinol of methoxyl group parylene monomer, 20 weight parts of 20 weight parts and 1.5 weight parts, react 2h under the condition of 125 ℃, after cooling down, add the ammoniacal liquor of the 20wt% of 1.5 weight parts, the vinylbenzene of 12 weight parts and the formaldehyde of 18 weight parts, dehydration reaction under the vacuum of 0.6KPa obtains modified phenolic resins after transparent;
Step 3: get modified phenolic resins that the polyborosiloxane that makes in step 1 and step 2 make and mix by the mass ratio of 3:10, obtain the boron modified phenolic resin tackiness agent.
Embodiment 3
Step 1: mixture and boric acid that phenyltrimethoxysila,e and methyltrimethoxy silane are made according to weight fraction 1:2 join in dioxane, under the condition existed at titanium tetrachloride, progressively be warmed up to 200 ℃ from 90 ℃ in lower 3 hours of nitrogen atmosphere, continue reaction 5h; Then add Resorcinol, reaction 6h, after water pump Depressor response 2h, obtain polyborosiloxane (PBSH); Organo-siloxane: boric acid: the mol ratio of Resorcinol is 1:1:1, and catalyst levels is 1 ‰ of monomer total mass;
Step 2: the tosic acid of getting the 25wt% of the Resorcinol of methoxyl group parylene monomer, 20 weight parts of 20 weight parts and 1.5 weight parts, react 2h under the condition of 125 ℃, after cooling down, add the ammoniacal liquor of the 20wt% of 1.5 weight parts, the vinylbenzene of 12 weight parts and the formaldehyde of 18 weight parts, dehydration reaction under the vacuum of 0.6KPa obtains modified phenolic resins after transparent;
Step 3: get modified phenolic resins that the polyborosiloxane that makes in step 1 and step 2 make and mix by the mass ratio of 4:10, obtain the boron modified phenolic resin tackiness agent.
Embodiment 4
Step 1: mixture and boric acid that phenyltrimethoxysila,e and methyltrimethoxy silane are made according to weight fraction 1:2 join in diethylene glycol dimethyl ether, under the condition existed at Indian red, progressively be warmed up to 200 ℃ from 90 ℃ in lower 3 hours of nitrogen atmosphere, continue reaction 5h; Then add Resorcinol, reaction 6h, after water pump Depressor response 2h, obtain polyborosiloxane (PBSH); Organo-siloxane: boric acid: the mol ratio of Resorcinol is 1:1:1, and catalyst levels is 1 ‰ of monomer total mass;
Step 2: the tosic acid of getting the 25wt% of the Resorcinol of methoxyl group parylene monomer, 20 weight parts of 20 weight parts and 1.5 weight parts, react 2h under the condition of 125 ℃, after cooling down, add the ammoniacal liquor of the 20wt% of 1.5 weight parts, the vinylbenzene of 12 weight parts and the formaldehyde of 18 weight parts, dehydration reaction under the vacuum of 0.6KPa obtains modified phenolic resins after transparent;
Step 3: get modified phenolic resins that the polyborosiloxane that makes in step 1 and step 2 make and mix by the mass ratio of 5:10, obtain the boron modified phenolic resin tackiness agent.
Polyphenol in above-described embodiment 1-4 has all been selected Resorcinol, in the essentially identical situation of all the other conditions, only change the reaction ratio of polyborosiloxane and modified phenolic resins, then to the product that obtains in embodiment through gluing, solidify, measure its cohesive strength.Experimental result shows, the cohesive strength maximum of the sizing agent obtained when polyborosiloxane and modified phenolic resins mix by the mass ratio of 4:10.
The above has carried out exemplary description to the present invention in conjunction with the embodiments; obvious realization of the present invention is not subject to the restrictions described above; as long as the various improvement that adopted method design of the present invention and technical scheme to carry out; or without improving, design of the present invention and technical scheme are directly applied to other occasion, all in protection scope of the present invention.
Claims (9)
1. the making method of a boron modified phenolic resin sizing agent, comprise the following steps: step 1: synthetic polyborosiloxane (PBSH); Step 2: synthesis modification resol; Step 3: prepare the boron modified phenolic resin sizing agent.
2. the making method of boron modified phenolic resin sizing agent according to claim 1, it is characterized in that: described step 1 is that organo-siloxane and boric acid are joined in organic solvent, under the condition existed at catalyzer, progressively be warmed up to 200 ℃, reaction 1-5h from 90 ℃ in lower 3 hours of nitrogen atmosphere; Then add polyphenol, reaction 4-10h, after water pump Depressor response 1.5～3h, obtain polyborosiloxane (PBSH); Described step 2 is to get the Resorcinol of the methoxyl group parylene monomer of 20 weight parts, 20 weight parts and an acidic catalyst of 1.5 weight parts, react 1-4h under the condition of 125 ℃, after cooling down, add the basic catalyst of 1.5 weight parts, the organic solvent of 12 weight parts and the formaldehyde of 18 weight parts, dehydration reaction under the vacuum of 0.6KPa obtains modified phenolic resins after transparent; Described step 3 is to get modified phenolic resins that the polyborosiloxane that makes in step 1 and step 2 make to mix by the mass ratio of 1-6:10, obtains the boron modified phenolic resin tackiness agent.
3. the making method of boron modified phenolic resin sizing agent according to claim 2, it is characterized in that: the described organo-siloxane of step 1: boric acid: the mol ratio of polyphenol is 1:1～2:0.25～1, catalyst levels is 1 of monomer total mass～2 ‰.
4. the making method of boron modified phenolic resin sizing agent according to claim 2, it is characterized in that: the described organo-siloxane of step 1 is the mixture that phenyltrimethoxysila,e and methyltrimethoxy silane are made according to weight fraction 1:2.
5. the making method of boron modified phenolic resin sizing agent according to claim 2, it is characterized in that: the described solvent of step 1 is diethylene glycol dimethyl ether or dioxane.
6. the making method of boron modified phenolic resin sizing agent according to claim 2, it is characterized in that: the described catalyzer of step 1 is any one in tin protochloride, titanium tetrachloride, Indian red.
7. the making method of boron modified phenolic resin sizing agent according to claim 2, it is characterized in that: the described polyphenol of step 1 is a kind of or several mixing in pyrocatechol, Resorcinol, Resorcinol, Phloroglucinol, pyrogallol.
8. the making method of boron modified phenolic resin sizing agent according to claim 2 is characterized in that: the tosic acid that the described an acidic catalyst of step 2 is 25wt%, and the ammoniacal liquor that described basic catalyst is 20wt%, described organic solvent is vinylbenzene.
9. the making method of boron modified phenolic resin sizing agent according to claim 2, it is characterized in that: the mass ratio of the described polyborosiloxane of step 3 and modified phenolic resins is 2-5:10.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
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| CN201310377320.4A CN103468182B (en) | 2013-08-27 | 2013-08-27 | Preparation method of boron modified phenolic resin adhesive |
| CN201510000880.7A CN104592918B (en) | 2013-08-27 | 2013-08-27 | A kind of making method of boron modified phenolic resin sizing agent |
| CN201510000868.6A CN104592917B (en) | 2013-08-27 | 2013-08-27 | A kind of making method of boron modified phenolic resin sizing agent |
| CN201510000866.7A CN104592916B (en) | 2013-08-27 | 2013-08-27 | A kind of making method of boron modified phenolic resin sizing agent |
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| CN201310377320.4A CN103468182B (en) | 2013-08-27 | 2013-08-27 | Preparation method of boron modified phenolic resin adhesive |
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| CN201510000868.6A Division CN104592917B (en) | 2013-08-27 | 2013-08-27 | A kind of making method of boron modified phenolic resin sizing agent |
| CN201510000866.7A Division CN104592916B (en) | 2013-08-27 | 2013-08-27 | A kind of making method of boron modified phenolic resin sizing agent |
| CN201510000880.7A Division CN104592918B (en) | 2013-08-27 | 2013-08-27 | A kind of making method of boron modified phenolic resin sizing agent |
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| CN201510000866.7A Active CN104592916B (en) | 2013-08-27 | 2013-08-27 | A kind of making method of boron modified phenolic resin sizing agent |
| CN201310377320.4A Active CN103468182B (en) | 2013-08-27 | 2013-08-27 | Preparation method of boron modified phenolic resin adhesive |
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| CN104892009A (en) * | 2015-05-13 | 2015-09-09 | 武汉科技大学 | Modified resin used for unfired slide plates with higher volume-stability, and preparation method thereof |
| CN106543390A (en) * | 2016-10-21 | 2017-03-29 | 沈阳化工大学 | A kind of tetrahydroxy polyhedral silsesquioxane heat-resistant phenolic resins preparation method |
| CN109867965A (en) * | 2019-03-26 | 2019-06-11 | 华东理工大学 | A kind of high-temperature-resisting silicon rubber material and the preparation method and application thereof |
Also Published As
| Publication number | Publication date |
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| CN104592917B (en) | 2016-02-03 |
| CN104592918B (en) | 2016-02-03 |
| CN104592917A (en) | 2015-05-06 |
| CN103468182B (en) | 2014-11-26 |
| CN104592918A (en) | 2015-05-06 |
| CN104592916A (en) | 2015-05-06 |
| CN104592916B (en) | 2016-02-03 |
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