CN107474205A - A kind of preparation method of timber oxidation Cardanol Modified PF Resin adhesive - Google Patents

A kind of preparation method of timber oxidation Cardanol Modified PF Resin adhesive Download PDF

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Publication number
CN107474205A
CN107474205A CN201710785399.2A CN201710785399A CN107474205A CN 107474205 A CN107474205 A CN 107474205A CN 201710785399 A CN201710785399 A CN 201710785399A CN 107474205 A CN107474205 A CN 107474205A
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anacardol
preparation
resin adhesive
oxidation
timber
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夏青
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G8/00Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/28Chemically modified polycondensates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G8/00Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G8/00Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/10Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J161/00Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
    • C09J161/04Condensation polymers of aldehydes or ketones with phenols only
    • C09J161/06Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J161/00Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
    • C09J161/04Condensation polymers of aldehydes or ketones with phenols only
    • C09J161/06Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • C09J161/14Modified phenol-aldehyde condensates

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

A kind of preparation method the invention discloses timber with oxidation Cardanol Modified PF Resin adhesive, including aoxidizing the preparation of anacardol and the preparation of modified phenolic resin adhesive, the preparation for wherein aoxidizing anacardol is to react anacardol, acidic catalyst and oxidant Hybrid Heating, then sodium hydroxide solution regulation pH is added to wash between 10~12 to neutrality, the preparation of modified phenolic resin adhesive will melt phenol, oxidation anacardol, formaldehyde, sodium hydroxide and add Hybrid Heating in three-necked flask, and wherein formaldehyde adds at twice.The preparation method of the present invention is to anacardol oxidation processes, simple and easy, raw material sources are abundant, cheap, and the modified phenolic resin adhesive cost of gained is low, adhesive strength is high, the content of free phenol in synvaren is reduced, avoids harm of the synvaren to environment.

Description

A kind of preparation method of timber oxidation Cardanol Modified PF Resin adhesive
Technical field
The invention belongs to wood adhesive technical field, is a kind of timber oxidation modified by cardanol phenolic aldehyde specifically The preparation method of resin adhesive.
Background technology
Phenolic resin is earliest industrialized synthetic resin, and there is raw material to be easy to get, synthesize convenient, cheap spy for it Point, there are good mechanical performance, against weather, corrosion resistance, water resistance and certain heat resistance, therefore be widely used in making mould
The industries such as plastics, adhesive, coating.But because the fragility of unmodified phenolic resin is larger, free formaldehyde and free The presence of phenol causes that its harm to environment is larger, and this causes the application field of synvaren to be restricted.
Anacardol is by cashew nut shell liquid(Cashew nut oil)Middle extraction, cashew nut oil can obtain more pure waist through vacuum distillation Fruit phenol.In commodity cashew nut oil containing about 90 % anacardol, 10 % cashew nut between diphenol and a small amount of tannic acid, glucose and Glucoside, other polymers etc..It is cashew nut oil aboundresources, cheap, there is highly important development and application to be worth, can It is widely used in synthetic surfactant, improvement natural rubber and ion exchange resin etc..There is the meta of phenolic hydroxyl group in anacardol The fatty chain substituent of one 15 carbon, make anacardol that both there is the feature of phenolic compound, there is the soft of aliphatic compound again Property, so anacardol is used as biomass modified dose of synvaren.
Publication No. CN102516911A application for a patent for invention discloses a kind of friction material modified alkyd resin glue The preparation method of stick, first phenol, formalin, amine substance, anacardol are well mixed, composite catalyst, heating is added dropwise To 80 DEG C~105 DEG C, then isothermal reaction 0.5~2 hour, acidic catalyst is then added, continues 1~2h of isothermal reaction, Obtain crocus emulsus and glue thing, the crocus emulsus dope is washed 2~5 times in 60 DEG C~70 DEG C water, dry Dehydration, obtains anacardol, amine substance modified phenolic resin adhesive.
But directly substituting part phenol synthesis phenolic resin using anacardol has a large amount of bubble formations, in the industrial production Many inconvenience can be caused, it is difficult to a large amount of to use.With the presence of many carbon-carbon double bonds on the side chain of anacardol, and carbon-carbon double bond is easy to It is oxidized, phenolic resin performance can be caused unstable.Therefore need to be modified the molecular structure of anacardol, so that cashew nut Phenol is preferably incorporated in the synthetic system of phenolic resin, to reduce synthetic resin during generate bubble amount, to increase waist The replacement amount of fruit phenol Pyrogentisinic Acid, improve the stability of phenolic resin performance.
The content of the invention
For problems of the prior art and deficiency, it is an object of the invention to provide a kind of timber oxidation cashew nut The preparation method of phenol modified phenolic resin adhesive, this method is simple and easy, and raw material sources are abundant, cheap, and gained changes Property cost PF resin adhesive is low, adhesive strength is high, reduce the content of free phenol in synvaren, avoid phenolic aldehyde tree Harm of the fat adhesive to environment.
Technical problem solved by the invention can be realized using following technical scheme:A kind of timber oxidation anacardol The preparation method of modified phenolic resin adhesive, comprises the following steps:
A. the preparation of anacardol is aoxidized:Anacardol, acidic catalyst and oxidant are mixed, are heated to 50~80 DEG C, reaction 2 ~5h, discharged after being down to room temperature, stratification, remove aqueous phase, oil phase is washed with water to neutrality, then adds sodium hydroxide solution PH is adjusted between 10~12,80 DEG C of stirring 2h is heated to, stratification, removes aqueous phase, oil phase is washed with water to neutrality;
B. the preparation of modified phenolic resin adhesive:Will melting phenol, anacardol, three mouthfuls of sodium hydroxide addition at 40~50 DEG C In flask, 10~30min is incubated;The formaldehyde for accounting for formaldehyde total amount 60% is added, is warming up to 50~70 DEG C, is incubated 50~70min;Add Enter remaining formaldehyde, be warming up to 75~80 DEG C, be incubated 50~70min;85~90 DEG C of 40~60min of backflow are warming up to, rapidly It is cooled to 40~50 DEG C of dischargings.
In order to preferably realize the present invention, further, acidic catalyst is acetic acid, oxalic acid, trifluoro second in the step A At least one of acid, methane-siliconic acid and ethyl silicic acid.
In order to preferably realize the present invention, further, oxidant is hydrogen peroxide in the step A.
In order to preferably realize the present invention, further, oxidant is 30wt.% hydrogen peroxide in the step A.
In order to preferably realize the present invention, further, the mass ratio of acid catalyst and anacardol is in the step A(1 ~10):100, the mass ratio of anacardol and oxidant is 100:(20~50).
In order to preferably realize the present invention, further, the mol ratio of phenol and formaldehyde is 1 in the step B:(1.3~ 2.0), aoxidize anacardol and account for the 5~25% of phenol quality.
In order to preferably realize the present invention, further, in the step B aoxidize anacardol and account for the 10% of phenol quality.
The present invention compared with prior art, has advantages below and beneficial effect:
(1)The present invention carries out oxidation processes to anacardol, the carbon-carbon double bond destroyed on anacardol side chain, improves modified by cardanol The stability of synvaren.
(2)The present invention further adjusts waist on the basis of oxidation processes are carried out to anacardol using sodium hydroxide solution The pH of fruit phenol increases the polarity of anacardol side chain between 10~12, improves compatibility of the anacardol in phenolic resin system.
(3)The preparation method of the present invention can improve dosage of the anacardol in synvaren, substitute part phenol, Reduce free phenol content.
Embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, with reference to embodiments, to the present invention It is further elaborated.
Embodiment 1:
A kind of timber of the present embodiment preparation method of oxidation Cardanol Modified PF Resin adhesive, enters according to the following steps OK:
A. the preparation of anacardol is aoxidized:Anacardol, oxalic acid and 30wt.% hydrogen peroxide are mixed, are heated to 50 DEG C, reaction 2h, discharged after being down to room temperature, stratification, remove aqueous phase, oil phase is washed with water to neutrality, then adds sodium hydroxide solution and adjusts PH is saved between 10~12,80 DEG C of stirring 2h is heated to, stratification, removes aqueous phase, oil phase is washed with water to neutrality, its medium-height grass The mass ratio of acid and anacardol is 1:100, the mass ratio of anacardol and 30wt.% hydrogen peroxide is 100: 20;
B. the preparation of modified phenolic resin adhesive:Will melting phenol, anacardol, sodium hydroxide addition three-necked flask at 40 DEG C In, it is incubated 10min;The formaldehyde for accounting for formaldehyde total amount 60% is added, is warming up to 50 DEG C, is incubated 50min;Remaining formaldehyde is added, is heated up To 75 DEG C, 50min is incubated;85 DEG C of backflow 40min are warming up to, are quickly cooled to 40 DEG C of dischargings, wherein mole of phenol and formaldehyde Than for 1:1.3, oxidation anacardol accounts for the 5% of phenol quality.
Modified phenolic resin adhesive free phenol content made from the present embodiment is 7.0%, and the gluing intensity to timber is 1.03MPa。
Embodiment 2:
A kind of timber of the present embodiment preparation method of oxidation Cardanol Modified PF Resin adhesive, enters according to the following steps OK:
A. the preparation of anacardol is aoxidized:Anacardol, acetic acid and 30wt.% hydrogen peroxide are mixed, are heated to 60 DEG C, reacts 3h, Discharged after being down to room temperature, stratification, remove aqueous phase, oil phase is washed with water to neutrality, then adds sodium hydroxide solution regulation PH is heated to 80 DEG C of stirring 2h, stratification, removes aqueous phase, oil phase is washed with water to neutrality, wherein acetic acid between 10~12 Mass ratio with anacardol is 3:100, the mass ratio of anacardol and 30wt.% hydrogen peroxide is 100: 25;
B. the preparation of modified phenolic resin adhesive:Will melting phenol, anacardol, sodium hydroxide addition three-necked flask at 45 DEG C In, it is incubated 15min;The formaldehyde for accounting for formaldehyde total amount 60% is added, is warming up to 55 DEG C, is incubated 60min;Remaining formaldehyde is added, is heated up To 80 DEG C, 70min is incubated;90 DEG C of backflow 60min are warming up to, are quickly cooled to 50 DEG C of dischargings, wherein phenol and formaldehyde rubs You are than being 1:1.5, oxidation anacardol accounts for the 10% of phenol quality.
Modified phenolic resin adhesive free phenol content made from the present embodiment is 7.9%, and the gluing intensity to timber is 1.23MPa。
Embodiment 3:
A kind of timber of the present embodiment preparation method of oxidation Cardanol Modified PF Resin adhesive, enters according to the following steps OK:
A. the preparation of anacardol is aoxidized:Anacardol, trifluoroacetic acid and 30wt.% hydrogen peroxide are mixed, are heated to 65 DEG C, instead 3.5h is answered, is discharged after being down to room temperature, stratification, removes aqueous phase, oil phase is washed with water to neutrality, it is molten then to add sodium hydroxide Liquid adjusts pH between 10~12, is heated to 80 DEG C of stirring 2h, stratification, removes aqueous phase, oil phase is washed with water to neutrality, its The mass ratio of middle trifluoroacetic acid and anacardol is 5:100, the mass ratio of anacardol and 30wt.% hydrogen peroxide is 100: 30;
B. the preparation of modified phenolic resin adhesive:Will melting phenol, anacardol, sodium hydroxide addition three-necked flask at 50 DEG C In, it is incubated 20min;The formaldehyde for accounting for formaldehyde total amount 60% is added, is warming up to 70 DEG C, is incubated 60min;Remaining formaldehyde is added, is heated up To 80 DEG C, 65min is incubated;90 DEG C of backflow 50min are warming up to, are quickly cooled to 50 DEG C of dischargings, wherein phenol and formaldehyde rubs You are than being 1:1.7, oxidation anacardol accounts for the 15% of phenol quality.
Modified phenolic resin adhesive free phenol content produced by the present invention is 10.0%, and the gluing intensity to timber is 0.93MPa。
Embodiment 4:
A kind of timber of the present embodiment preparation method of oxidation Cardanol Modified PF Resin adhesive, enters according to the following steps OK:
A. the preparation of anacardol is aoxidized:Anacardol, methane-siliconic acid and 30wt.% hydrogen peroxide are mixed, are heated to 70 DEG C, instead 4h is answered, is discharged after being down to room temperature, stratification, aqueous phase is removed, oil phase is washed with water to neutrality, then adds sodium hydroxide solution PH is adjusted between 10~12,80 DEG C of stirring 2h is heated to, stratification, removes aqueous phase, oil phase is washed with water to neutrality, wherein The mass ratio of trifluoroacetic acid and anacardol is 7:100, the mass ratio of anacardol and 30wt.% hydrogen peroxide is 100: 35;
B. the preparation of modified phenolic resin adhesive:Will melting phenol, anacardol, sodium hydroxide addition three-necked flask at 45 DEG C In, it is incubated 25min;The formaldehyde for accounting for formaldehyde total amount 60% is added, is warming up to 55 DEG C, is incubated 60min;Remaining formaldehyde is added, is heated up To 80 DEG C, 70min is incubated;85 DEG C of backflow 60min are warming up to, are quickly cooled to 50 DEG C of dischargings, wherein phenol and formaldehyde rubs You are than being 1:2, oxidation anacardol accounts for the 20% of phenol quality.
Modified phenolic resin adhesive free phenol content made from the present embodiment is 8.5%, and the gluing intensity to timber is 1.21MPa。
Embodiment 5:
A kind of timber of the present embodiment preparation method of oxidation Cardanol Modified PF Resin adhesive, enters according to the following steps OK:
A. the preparation of anacardol is aoxidized:Anacardol, acidic catalyst and 30wt.% hydrogen peroxide are mixed, are heated to 50~80 DEG C, 2~5h is reacted, is discharged after being down to room temperature, stratification, aqueous phase is removed, oil phase is washed with water to neutrality, then adds hydrogen-oxygen Change sodium solution and adjust pH between 10~12, be heated to 80 DEG C of stirring 2h, stratification, remove aqueous phase, oil phase is washed with water extremely The mass ratio of neutrality, wherein trifluoroacetic acid and anacardol is 7:100, the mass ratio of anacardol and 30wt.% hydrogen peroxide is 100: 50;
B. the preparation of modified phenolic resin adhesive:Will melting phenol, anacardol, three mouthfuls of sodium hydroxide addition at 40~50 DEG C In flask, 10~30min is incubated;The formaldehyde for accounting for formaldehyde total amount 60% is added, is warming up to 50~70 DEG C, is incubated 50~70min;Add Enter remaining formaldehyde, be warming up to 75~80 DEG C, be incubated 50~70min;85~90 DEG C of 40~60min of backflow are warming up to, rapidly 40~50 DEG C of dischargings are cooled to, the wherein mol ratio of phenol and formaldehyde is 1:1.4, oxidation anacardol accounts for the 10% of phenol quality.
Modified phenolic resin adhesive free phenol content made from the present embodiment is 9.1%, and the gluing intensity to timber is 1.12MPa。
Embodiment 6:
A kind of timber of the present embodiment preparation method of oxidation Cardanol Modified PF Resin adhesive, enters according to the following steps OK:
A. the preparation of anacardol is aoxidized:Anacardol, ethyl silicic acid and oxidant are mixed, are heated to 50~80 DEG C, reaction 2~ 5h, discharged after being down to room temperature, stratification, remove aqueous phase, oil phase is washed with water to neutrality, then adds sodium hydroxide solution and adjusts PH is saved between 10~12,80 DEG C of stirring 2h is heated to, stratification, removes aqueous phase, oil phase is washed with water to neutrality, wherein second The mass ratio of base silicic acid and anacardol is 7:100, the mass ratio of anacardol and 30wt.% hydrogen peroxide is 100: 35;
B. the preparation of modified phenolic resin adhesive:Will melting phenol, anacardol, three mouthfuls of sodium hydroxide addition at 40~50 DEG C In flask, 10~30min is incubated;The formaldehyde for accounting for formaldehyde total amount 60% is added, is warming up to 50~70 DEG C, is incubated 50~70min;Add Enter remaining formaldehyde, be warming up to 75~80 DEG C, be incubated 50~70min;85~90 DEG C of 40~60min of backflow are warming up to, rapidly 40~50 DEG C of dischargings are cooled to, the wherein mol ratio of phenol and formaldehyde is 1:1.8, oxidation anacardol accounts for the 25% of phenol quality.
Modified phenolic resin adhesive free phenol content made from the present embodiment is 10.1%, and the gluing intensity to timber is 0.90MPa。
Table 1 is that the free phenol content of modified phenolic resin adhesive and the gluing intensity to timber is made in embodiment 1~6
Finally illustrate, the general principle and principal character and advantages of the present invention of the present invention has been shown and described above.This Art personnel it should be appreciated that the present invention is not limited to the above embodiments, described in above-described embodiment and specification only It is the principle of the present invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, this A little changes and improvements all fall within the protetion scope of the claimed invention.

Claims (7)

1. a kind of timber preparation method of oxidation Cardanol Modified PF Resin adhesive, it is characterised in that including following step Suddenly:A. the preparation of anacardol is aoxidized:Anacardol, acidic catalyst and oxidant are mixed, are heated to 50~80 DEG C, reaction 2 ~5h, discharged after being down to room temperature, stratification, remove aqueous phase, oil phase is washed with water to neutrality, then adds sodium hydroxide solution PH is adjusted between 10~12,80 DEG C of stirring 2h is heated to, stratification, removes aqueous phase, oil phase is washed with water to neutrality;
B. the preparation of modified phenolic resin adhesive:Will melting phenol, oxidation anacardol, sodium hydroxide addition at 40~50 DEG C In three-necked flask, 10~30min is incubated;Add and account for the formaldehyde of formaldehyde total amount 60%, be warming up to 50~70 DEG C, insulation 50~ 70min;Remaining formaldehyde is added, is warming up to 75~80 DEG C, is incubated 50~70min;Be warming up to 85~90 DEG C backflow 40~ 60min, it is quickly cooled to 40~50 DEG C of dischargings.
2. a kind of preparation method of timber oxidation Cardanol Modified PF Resin adhesive according to claim 1, its It is characterised by:In the step A acidic catalyst be acetic acid, oxalic acid, trifluoroacetic acid, methane-siliconic acid and ethyl silicic acid at least It is a kind of.
3. a kind of preparation method of timber oxidation Cardanol Modified PF Resin adhesive according to claim 1, its It is characterised by:Oxidant is hydrogen peroxide in the step A.
4. a kind of preparation method of timber oxidation Cardanol Modified PF Resin adhesive according to claim 3, its It is characterised by:Oxidant is 30wt.% hydrogen peroxide in the step A.
5. a kind of preparation method of timber oxidation Cardanol Modified PF Resin adhesive according to claim 1, its It is characterised by:The mass ratio of acid catalyst and anacardol is in the step A(1~10):100, the matter of anacardol and oxidant Amount is than being 100:(20~50).
6. according to a kind of timber according to any one of claims 1 to 5 oxidation Cardanol Modified PF Resin adhesive Preparation method, it is characterised in that:The mol ratio of phenol and formaldehyde is 1 in the step B:(1.3~2.0), aoxidize anacardol and account for The 5~25% of phenol quality.
7. a kind of preparation method of timber oxidation Cardanol Modified PF Resin adhesive according to claim 6, its It is characterised by:Anacardol is aoxidized in the step B and accounts for the 10% of phenol quality.
CN201710785399.2A 2017-09-04 2017-09-04 A kind of preparation method of timber oxidation Cardanol Modified PF Resin adhesive Pending CN107474205A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109351911A (en) * 2018-11-07 2019-02-19 合肥凯大新型材料科技有限公司 A kind of phenolic resin adhesive reducing resin content

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CN102516911A (en) * 2011-12-14 2012-06-27 黄石金朝阳粉末材料有限责任公司 Modified phenolic resin adhesive for friction material and preparation method for modified phenolic resin adhesive
CN103122054A (en) * 2013-02-19 2013-05-29 中国西电集团公司 Method for modifying phenolic resin by using cardanol
CN104497244A (en) * 2014-12-11 2015-04-08 贵阳学院 Preparation method of anacardol modified phenolic resin
CN104974320A (en) * 2015-06-25 2015-10-14 中国林业科学研究院林产化学工业研究所 Oxidized cardanol-modified phenolic resin and preparation method and application thereof
CN106750062A (en) * 2016-12-16 2017-05-31 沙县宏盛塑料有限公司 A kind of phenolic resin of modified by cardanol and the preparation method of phenolaldehyde moulding compound

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102408672A (en) * 2011-08-05 2012-04-11 江苏星源航天材料股份有限公司 Production method for cardanol modified phenolic resin
CN102516911A (en) * 2011-12-14 2012-06-27 黄石金朝阳粉末材料有限责任公司 Modified phenolic resin adhesive for friction material and preparation method for modified phenolic resin adhesive
CN103122054A (en) * 2013-02-19 2013-05-29 中国西电集团公司 Method for modifying phenolic resin by using cardanol
CN104497244A (en) * 2014-12-11 2015-04-08 贵阳学院 Preparation method of anacardol modified phenolic resin
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109351911A (en) * 2018-11-07 2019-02-19 合肥凯大新型材料科技有限公司 A kind of phenolic resin adhesive reducing resin content

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