CN102391448B - Preparation method of phenolic resin for resin grinding wheel adhesive and thermosetting liquid phenolic resin - Google Patents
Preparation method of phenolic resin for resin grinding wheel adhesive and thermosetting liquid phenolic resin Download PDFInfo
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- CN102391448B CN102391448B CN 201110243013 CN201110243013A CN102391448B CN 102391448 B CN102391448 B CN 102391448B CN 201110243013 CN201110243013 CN 201110243013 CN 201110243013 A CN201110243013 A CN 201110243013A CN 102391448 B CN102391448 B CN 102391448B
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Abstract
The invention provides a preparation method of phenolic resin for a resin grinding wheel adhesive, which comprises the following steps that: in the presence of an organic amine catalyst, a phenolic compound and formaldehyde are subjected to a condensation reaction; a mixture obtained by the condensation reaction is subjected to vacuum distillation, and then a coupling agent is added to the mixture to obtain a phenolic resin. The invention also provides a thermosetting liquid phenolic resin with a metal ion concentration of less than 100PPM. In the method provided by the invention, on one hand, organic amine is used as the catalyst to improve the water resistance of the phenolic resin, on the other hand, the coupling agent is used to improve the adhesion strength of the phenolic resin and other materials, so that the situation that the phenolic resin has higher adhesion strength for a long time is ensured, and thus the performance degradation of a resin grinding wheel is not easily caused by reduced adhesion strength of the phenolic resin in a storage period, and the service life of the resin grinding wheel is prolonged.
Description
Technical field
The present invention relates to polymeric material field, particularly a kind of preparation method and heat curing-type liquid phenolic resin of the resol for the resin wheel tackiness agent.
Background technology
Resol claims again bakelite, is made by phenolic compound and formaldehyde condensation.Resol is the synthetic resins of realizing the earliest suitability for industrialized production, and it has excellent resistance to elevated temperatures, also can keep the globality of its structure and the stability of size under hot conditions.Just because of this, resol is widely used as refractory materials, friction materials and tackiness agent etc.
Tackiness agent is the topmost application of phenolic resin material, and resol just is used as the tackiness agent of the coated abrasive tools such as resin wheel, brake band and clutch surface from the sixties in 20th century.Material usually finish grindes and polishes by the organic resin grinding tool in carrying out ground finish, and organic grinding tool has certain elastic deformation, the available buffer grinding force, thereby grinding and polishing effect are good, can reduce the roughness of material surface.The resol resistance toheat is good, and mechanical strength is high, and flame retardant resistance and electrical insulation capability are good, and high temperature resistant creep property is excellent and cheap, is one of most important tackiness agent in the coated abrasive tool technique.
Resin wheel is with binding agent abrasive material to be sticked to the circular bonded abrasive tool that the central authorities of making on the resin base material are provided with through hole.During use, the emery wheel high speed rotating can be roughly ground cylindrical, inner circle and the multiple profile of metal or non-metal workpiece, half correct grinding, correct grinding, fluting or cut-out etc., is a kind of grinding tool that a kind of consumption is maximum, use range is the widest.In the existing resin wheel industry, especially the difficult problem that ultra-thin resin wheel industry all exists: resin wheel performance degradation always occurs at memory period, be embodied in: the emery wheel of harsh product is when cutting operation, has very high cutting ratio, but product is after storage for some time, about about 1 month, the performance of emery wheel will reduce about 30% ~ 60%.This usability and mill that has had a strong impact on emery wheel is cut the life-span.
Summary of the invention
Existing resin wheel adopts resol usually with binding agent, and the inventor finds after deliberation: the reduction of phenolic resin bonded intensity is to affect one of principal element of grinding wheel performance decline.Existing heat curing-type liquid phenolic resin mostly is water soluble resin, and catalyzer is alkali-metal oxyhydroxide or oxide compound, and the most common is NaOH.Behind resin solidification, base metal catalysts can all remain in the resol, and namely base metal catalysts is present in the resin wheel system.Emery wheel is in storage process, the moisture of external environment can infiltrate resin system, and along with the increase of moisture in the resin wheel, basic metal produces ionizing event under the effect of water molecules, destroy the cohesive action between resin and the abrasive material, thereby caused the decline of resin property.
The technical problem that the present invention solves is to provide a kind of preparation method of the resol for the resin wheel binding agent, and this resol can keep higher cohesive strength for a long time.
In view of this, the invention provides a kind of preparation method of the resol for the resin wheel binding agent, comprising:
Under the condition that the organic amine catalyzer exists, phenolic compound and formaldehyde generation condensation reaction;
Add coupling agent after the mixture vacuum distilling that condensation reaction is obtained, obtain resol.
Preferably, described organic amine catalyzer is hydramine.
Preferably, described hydramine is one or more in Monoethanolamine MEA BASF, diethanolamine, trolamine, dimethyl hydramine, the diglycolamine.
Preferably, described phenolic compound is one or more in phenol, Resorcinol, meta-cresol, the p-tert-butylphenol.
Preferably, described coupling agent is organo silane coupling agent.
Preferably, the weight ratio of described organic amine catalyzer and phenolic compound is 100:(1 ~ 5).
Preferably, the mol ratio of described phenolic compound and formaldehyde is 1:(1 ~ 1.6).
Preferably, the weight ratio of described phenolic compound and coupling agent is 100:(0.1 ~ 1).
Preferably, the temperature 70 C of described condensation reaction ~ 85 ℃.
The present invention also provides a kind of heat curing-type liquid phenolic resin, and its concentration of metal ions is no more than 100PPM.
The invention provides a kind of preparation method of the resol for the resin wheel tackiness agent, comprise the steps: under the condition that the organic amine catalyzer exists phenolic compound and formaldehyde generation condensation reaction; Add coupling agent after the mixture vacuum distilling that condensation reaction is obtained, obtain resol.By such scheme as can be known, the present invention is in order to improve the bond strength of resol, at first, adopt organic amine as catalyzer, because organic amine is volatile, residual quantity after the reaction in resol is lower, and the organic amine that remains in the resol also can crosslinked and stable being present in the resin system occur with resol, meets water and ionizing event can not occur.Improve thus the water resistance of resol self, make resol have for a long time preferably bond strength, reduce water molecules to the destructive force of resol and emery wheel bonding strength.Secondly, add coupling agent to reacted resol, improve the bond strength of resol and other materials.
Therefore, one aspect of the present invention adopts organic amine to improve the water resistance of resol as catalyzer, adopt on the other hand coupling agent to improve the bond strength of resol and other materials, guarantee that thus resol can have higher bond strength for a long time, so that resin wheel is difficult for causing performance degradation because of the reduction of phenolic resin adhesion intensity at memory period, prolonged the work-ing life of resin wheel.
Embodiment
In order further to understand the present invention, below in conjunction with embodiment the preferred embodiment of the invention is described, but should be appreciated that these describe just as further specifying the features and advantages of the present invention, rather than to the restriction of claim of the present invention.
The embodiment of the invention discloses a kind of preparation method of the resol for the resin wheel tackiness agent, comprising:
Under the condition that the organic amine catalyzer exists, phenolic compound and formaldehyde generation condensation reaction;
Add coupling agent after the mixture vacuum distilling that condensation reaction is obtained, obtain resol.
Among the above-mentioned preparation method, the first step is the operation of using organic amine catalysis phenolic compound and formaldehyde to carry out condensation.With respect to the catalyzer of alkaline metal salt, the present invention selects organic amine to be as the purpose of catalyzer: at first, organic amine also has preferably katalysis to above-mentioned condensation reaction; Secondly, organic amine is more volatile, and the residual quantity in resol is little; At last, residual a small amount of organic amine can occur crosslinkedly with resol, and stable is present in the phenolic resin system, meets water and also ionizing event can not occur.Therefore, adopt organic amine can improve the water resistance of resol as the catalyzer of condensation reaction, reduce water molecules to the destructive force of resol and emery wheel bonding strength.
The organic amine catalyzer preferably adopts hydramine, and itself and phenol have preferably consistency, and more volatile, and the later stage easily removes, less residue in resol.More preferably adopt in Monoethanolamine MEA BASF, diethanolamine, trolamine, dimethyl hydramine, the diglycolamine one or more.Phenolic compound preferably adopts one or more in phenol, Resorcinol, meta-cresol, the p-tert-butylphenol, and more preferably phenol or Resorcinol most preferably adopt phenol.
In the condensation reaction, the weight ratio of phenolic compound and organic amine catalyzer is preferably 100:(1 ~ 5), catalyst levels crosses that I haven't seen you for ages and reduces the resultant velocity of resol, greatly reduces production efficiency; The excessive one side of catalyst levels can make speed of response too fast, and reaction is not easy control, also can cause on the other hand catalyzer too much residual, affects the hardness of resin.For this reason, more preferably controlling phenolic compound and weight ratio organic amine is 100:(2.5 ~ 4).
The mol ratio of phenolic compound and formaldehyde preferably is controlled to be 1:(1 ~ 1.6), formaldehyde is very few, and the phenolic resin curing cross-linking density is little, and intensity is lower, and resistance toheat descends; Formaldehyde is too much, and the resol cross-linking density is large, although intensity is high, resistance toheat is good, and resin fragility increases.
The temperature of above-mentioned condensation reaction preferably is made as 70 ℃ ~ 85 ℃, preferably carries out in the following manner:
Phenolic compound and organic amine catalyst mix is even, obtain the mixing solutions of phenolic compound and organic amine catalyzer;
Under 70 ℃ ~ 85 ℃, add formaldehyde in the described mixing solutions in batches and carry out condensation reaction, preferably add complete at 60min ~ 120min formaldehyde.Then solution is warming up to 80 ℃ ~ 85 ℃ and continues reaction, the reaction times preferably is controlled to be 1.5h ~ 3h, and the concentration of formaldehyde is less than 1.2% in the control reactant.
The mixture that needs after the condensation reaction reaction is obtained carries out vacuum distilling, and phenol resin solution is concentrated, and also can remove the organic amine catalyzer simultaneously.Pressure preferably is made as 60mmHg ~ 80mmHg in the vacuum distilling operation, and temperature preferably is controlled to be 35 ℃ ~ 45 ℃.The water content that preferably will be distilled to phenol resin solution is 6% ~ 14%, and viscosity is 300 ~ 2000cp25 ℃.
Add coupling agent in the backward phenol resin solution of vacuum distilling, the purpose that adds coupling agent is to improve the bonding strength of resol and inorganic materials.Coupling agent preferably adopts organo silane coupling agent, and more preferably adopting model is the coupling agent of KH550, KH560, KH570, KH792, DL602 or DL171.The add-on of coupling agent and the weight ratio of phenolic compound are preferably (0.1 ~ 1): 100.Coupling agent adds the bonding strength that too much can reduce on the contrary resol, also can the water resistance of resol be impacted simultaneously.Adding coupling agent in the phenol resin solution mixes rear discharging and just obtains resol for the resin wheel tackiness agent.
By such scheme as can be known, the present invention is in order to improve the bond strength of resol, at first, adopt organic amine as catalyzer, because organic amine is volatile, residual quantity after the reaction in resol is lower, and the organic amine that remains in the resol also can crosslinked and stable being present in the resin system occur with resol, meets water and ionizing event can not occur.Improve thus the water resistance of resol self, make resol have for a long time preferably bond strength, reduce water molecules to the destructive force of resol and emery wheel bonding strength.Secondly, add coupling agent to reacted resol, improve the bond strength of resol and other materials.Therefore, one aspect of the present invention adopts organic amine to improve the water resistance of resol as catalyzer, adopt on the other hand coupling agent to improve the bond strength of resol and other materials, guarantee that thus resol can have higher bond strength for a long time, so that resin wheel is difficult for causing performance degradation because of the reduction of phenolic resin adhesion intensity at memory period, prolonged the work-ing life of resin wheel.
The present invention also provides a kind of heat curing-type liquid phenolic resin, its concentration of metal ions is no more than 100PPM, it can prepare according to the method described above, owing to be to adopt organic amine as catalyzer, organic amine is volatile, residual quantity after the reaction in resol is lower, crosslinked and stable being present in the resin system also can occur with resol in the organic amine that remains in the resol, therefore, this heat curing-type liquid phenolic is met water ionizing event can not occur, can keep for a long time higher bonding strength, be suitable as the tackiness agent of resin wheel.
In order further to understand the present invention, below in conjunction with embodiment the preparation method of the resol for the resin wheel tackiness agent provided by the invention is described, protection scope of the present invention is not limited by the following examples.Silane coupling agent in following examples by Nanjing forward chemical industry company limited provide.
Embodiment 1
With phenol 500g, Monoethanolamine MEA BASF catalyzer 10g drops into reactor, under atmospheric pressure state, reactant is warmed up to 80 ℃, adding concentration under 80 ℃ of temperature is 37% formaldehyde solution 517g, added in 90 minutes, then keep 80 ℃ to react, react after 2 hours, concentration of formaldehyde is 0.7% in the sampling detecting reactant; Vacuum distilling reaction solution, pressure are at 70mmHg, and Heating temperature is 38 ℃, are distilled to moisture content 9.2%, and viscosity 500cp25 ℃, be cooled to rapidly below 40 degree, add the 1g Silane coupling agent KH550, mixed discharging 1 hour.
The concentration that detects metal ion in the product is 36PPM.
Embodiment 2
With phenol 500g, diethanolamine catalyzer 20g drops into reactor, under atmospheric pressure state, reactant is warmed up to 80 ℃, adding concentration under 80 ℃ of temperature is 37% formaldehyde solution 560g, added in 60 minutes, then keep 80 ℃ to react, react after 150 minutes, concentration of formaldehyde is 0.9% in the sampling detecting reactant; Vacuum distilling reaction solution, pressure are at 70mmHg, and Heating temperature is 42 ℃, are distilled to moisture content 12%, and viscosity 600cp25 ℃, be cooled to rapidly below 40 degree, add the 5g Silane coupling agent KH550, mixed discharging 1 hour.
The concentration that detects metal ion in the product is 57PPM.
Embodiment 3
With phenol 500g, trolamine catalyzer 20g drops into reactor, under atmospheric pressure state, reactant is warmed up to 70 ℃, adding concentration under 70 ℃ of temperature is 37% formaldehyde solution 689.4g, added in 120 minutes, then keep 80 ℃ to react, react after 150 minutes, concentration of formaldehyde is less than being 1% in the sampling detecting reactant; Vacuum distilling reaction solution, pressure are at 70mmHg, and Heating temperature is 42 ℃, are distilled to moisture content 14%, and viscosity 1200cp25 ℃, be cooled to rapidly below 40 degree, add the 2.5g Silane coupling agent KH550, mixed discharging 1 hour.
The concentration that detects metal ion in the product is 87PPM.
Embodiment 4
With phenol 500g, dimethyl ethanolamine catalyst 8g drops into reactor, under atmospheric pressure state, reactant is warmed up to 80 ℃, adding concentration under 80 ℃ of temperature is 37% formaldehyde solution 560g, added in 60 minutes, then keep 85 ℃ to react, react after 150 minutes, concentration of formaldehyde is 1.0% in the sampling detecting reactant; Vacuum distilling reaction solution, pressure are at 70mmHg, and Heating temperature is 35 ℃, are distilled to moisture content 12%, and viscosity 900cp25 ℃, be cooled to rapidly below 40 degree, add the 2.5g Silane coupling agent KH550, mixed discharging 1 hour.
The concentration that detects metal ion in the product is 64PPM.
Embodiment 5
With phenol 500g, diglycolamine catalyzer 25g drops into reactor, under atmospheric pressure state, reactant is warmed up to 75 ℃, adding concentration under 75 ℃ of temperature is 37% formaldehyde solution 517g, added in 90 minutes, then keep 80 ℃ to react, react after 2 hours, concentration of formaldehyde is 0.7% in the sampling detecting reactant; Vacuum distilling reaction solution, pressure are at 70mmHg, and Heating temperature is 45 ℃, are distilled to moisture content 9.0%, and viscosity 600cp25 ℃, be cooled to rapidly below 40 degree, add the 2g Silane coupling agent KH550, mixed discharging 1 hour.
The concentration that detects metal ion in the product is 49PPM.
Comparative example 1
With phenol 500g, sodium hydroxide catalyst 8g drops into reactor, under atmospheric pressure state, reactant is warmed up to 80 ℃, adding concentration under 80 ℃ of temperature is 37% formaldehyde solution 517g, added in 90 minutes, then keep 80 ℃ to react, react after 2 hours, concentration of formaldehyde is 0.7% in the sampling detecting reactant; Vacuum distilling reaction solution, pressure are at 70mmHg, and Heating temperature is 38 ℃, are distilled to moisture content 9.2%, and viscosity 600cp25 ℃, discharging.
The concentration that detects metal ion in the product is 55300PPM.
Take by weighing respectively the embodiment 1 ~ 5 of equal in quality and the liquid phenolic resin of comparative example 1 preparation, be to be pressed into 8 word modules after the PF-2550 mixed with resin with the beautiful model of sending out F24 abrasive material that abrasive material company limited produces and holy well chemical industry and providing in itself and Zhengzhou, forming pressure is 6Mpa.Test the room temperature tensile strength of above-mentioned module, test result is listed in table 1.
Prepare respectively according to the method described above same module, soak in 25 ℃ of water and took out afterwards its water-fast tensile strength of test in 7 days, test result is listed in table 1.
Table 1 resol the performance test results
Use respectively the resol of embodiment 1 ~ 5 and comparative example 1 preparation to prepare the resin wheel that model is 105 * 1 * 16mm as tackiness agent, above-mentioned resin wheel is cut consume test, cutting material is Φ 14mm round steel, 20 cuttves.Test result is listed in table 2.
Table 2 resin wheel cutting property test result
By the above results as can be known: existing resol at water-fast strength decreased 46.13%, the water-fast intensity maximum of resol of the present invention preparation has reduced by 14.48%; Also further be proven by the emery wheel cutting test: after 30 days existing resin thin slice grinding wheel performance degradation 48%, and resin wheel maximum of the present invention has failed 20.7%; 60 days afterwards existing resin thin slice grinding wheel performance degradation 60%, and the emery wheel maximum of resin of the present invention has failed 24.6%.Hence one can see that, adopts resol provided by the invention can improve water resistance and the antifading of resin wheel as tackiness agent, and work-ing life is longer.
The explanation of above embodiment just is used for helping to understand method of the present invention and core concept thereof.Should be pointed out that for those skilled in the art, under the prerequisite that does not break away from the principle of the invention, can also carry out some improvement and modification to the present invention, these improvement and modification also fall in the protection domain of claim of the present invention.
To the above-mentioned explanation of the disclosed embodiments, make this area professional and technical personnel can realize or use the present invention.Multiple modification to these embodiment will be apparent concerning those skilled in the art, and General Principle as defined herein can in the situation that does not break away from the spirit or scope of the present invention, realize in other embodiments.Therefore, the present invention will can not be restricted to these embodiment shown in this article, but will meet the widest scope consistent with principle disclosed herein and features of novelty.
Claims (6)
1. a preparation method who is used for the resol of resin wheel tackiness agent is characterized in that, comprising:
Under the condition that the organic amine catalyzer exists, phenolic compound and formaldehyde generation condensation reaction, described organic amine catalyzer is hydramine;
Add coupling agent after the mixture vacuum distilling that condensation reaction is obtained, obtain resol, described coupling agent is organo silane coupling agent, and the weight ratio of described phenolic compound and coupling agent is 100:(0.1 ~ 1).
2. preparation method according to claim 1 is characterized in that, described hydramine is one or more in Monoethanolamine MEA BASF, diethanolamine, trolamine, dimethyl hydramine, the diglycolamine.
3. preparation method according to claim 1 is characterized in that, described phenolic compound is one or more in phenol, Resorcinol, meta-cresol, the p-tert-butylphenol.
4. preparation method according to claim 1 is characterized in that, the weight ratio of described phenolic compound and organic amine catalyzer is 100:(1 ~ 5).
5. preparation method according to claim 1 is characterized in that, the mol ratio of described phenolic compound and formaldehyde is 1:(1 ~ 1.6).
6. preparation method according to claim 1 is characterized in that, the temperature 70 C of described condensation reaction ~ 85 ℃.
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| CN103481210B (en) * | 2013-09-05 | 2016-03-09 | 宁波大华砂轮有限公司 | A kind of emery wheel mesh sheet bonding agent and preparation method thereof |
| CN105885748A (en) * | 2014-10-27 | 2016-08-24 | 北京玻钢院复合材料有限公司 | Novel deposition-free environment-friendly heat-insulation material adhesive and preparation method thereof |
| CN106674454A (en) * | 2016-12-30 | 2017-05-17 | 珠海邦瑞合成材料有限公司 | Powdery phenolic resin for diamond grinding block and preparation method thereof |
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| US7642333B2 (en) * | 2007-05-21 | 2010-01-05 | Georgia-Pacific Chemicals Llc | Anhydride and resorcinol latent catalyst system for improving cure characteristics of phenolic resins |
| JP2010209216A (en) * | 2009-03-10 | 2010-09-24 | Sumitomo Bakelite Co Ltd | Phenol resin, resin composition for wet paper friction material, and wet paper friction material |
| CN102108275B (en) * | 2011-01-22 | 2014-12-17 | 江苏泰尔新材料股份有限公司 | Composite modification method for phenolic resin adhesive |
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Address after: 250204 Shengquan Industrial Park, 50 meters southwest of the intersection of Zhongfu Road and Shengquan Road, Diaozhen Town, Zhangqiu District, Jinan City, Shandong Province Patentee after: SHANDONG SHENGQUAN NEW MATERIAL CO., LTD. Address before: 250204 Chemical Industrial Park, Diao Town, Zhangqiu, Ji'nan, Shandong Patentee before: Shandong Shengquan Chemical Industry Co., Ltd. |
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