CN109369868A - A method of improving phenolic resin adhesive curing rate - Google Patents
A method of improving phenolic resin adhesive curing rate Download PDFInfo
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- CN109369868A CN109369868A CN201811406435.0A CN201811406435A CN109369868A CN 109369868 A CN109369868 A CN 109369868A CN 201811406435 A CN201811406435 A CN 201811406435A CN 109369868 A CN109369868 A CN 109369868A
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- phenolic resin
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- resin adhesive
- reaction
- curing rate
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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
- C08G8/28—Chemically modified polycondensates
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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
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09J161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C09J161/14—Modified 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
The present invention relates to new function material technical fields, disclose a kind of method for improving phenolic resin adhesive curing rate, during phenolic resin preparation, phenolic aldehyde is reacted with formaldehyde according to the proportion that molar ratio is 1:1.9-2.0, whole phenolic resin is added in three-necked flask by the first step, and the formaldehyde that mass percent is 17-20% is then added, after mixing, the modified catalyst being prepared is added;Remaining formaldehyde is added in reaction system, passes through catalytic modification by second step, space steric effect is reduced, phenol ortho reactivity is improved, inhibits the generation of gaseous aldehyde, successfully improve its curing performance and thermal stability, existing phenolic resin adhesive is overcome since water content is higher, water diffusion is obstructed, and curing rate is slow, the problem of stability difference, and durability and bonding strength are high, improve to the resistance of temperature, significantly extend the service life of phenolic resin adhesive.
Description
Technical field
The invention belongs to new function material technical fields, and in particular to a kind of raising phenolic resin adhesive curing rate
Method.
Background technique
Phenolic resin is the general designation that phenols and aldehydes form resin under the action of catalyst.It is industrialization earliest (1910
Year, German Bakelite) synthesis high molecular material.In the time in a nearly century, it is used for many industrial fields, now
Still it is important synthesis high molecular material.In wood processing field phenolic resin be using one of extensive main glue kind,
Dosage is only second to Lauxite.Especially phenolic resin has special meaning in terms of producing water-fast, weatherability woodwork.Phenol
Urea formaldehyde adhesive have it is heat-resist, adhesive strength is high, ageing-resistant performance is good and electrical insulating property is excellent, and it is inexpensive it is easy-to-use grade spies
Point, therefore have obtained relatively broad application.
With the development of adhesive industry, the adhesive of more and more kinds is developed and used, and phenolic resin glue
There is colors for glutinous agent relatively deeply, has certain brittleness, is easily cracked, and especially water soluble phenol resin solidifies compared with Lauxite
Time is longer, solidification temperature is high, requires the disadvantages of stringent to Veneer moisture, especially curing time length has seriously affected gluing
The service performance of agent limits the development and utilization and market prospects of phenolic resin adhesive.And existing method of modifying, technique
Complexity, modified effect is general, and higher cost, is difficult to keep the stability of bonding strength.
Summary of the invention
The purpose of the present invention is being directed to existing problem, a kind of side for improving phenolic resin adhesive curing rate is provided
Method reduces space steric effect by catalytic modification, improves phenol ortho reactivity, inhibits the generation of gaseous aldehyde, at
Function improves its curing performance and thermal stability.
The present invention is achieved by the following technical solutions:
A method of phenolic resin adhesive curing rate being improved, during phenolic resin preparation, phenolic aldehyde and formaldehyde are according to rubbing
, than being that the proportion of 1:1.9-2.0 is reacted, whole phenolic resin is added in three-necked flask by the first step for you, then plus
Enter the formaldehyde that mass percent is 17-20% the modified catalyst being prepared is added, is warming up to 66-68 DEG C after mixing
It closes heater afterwards to be reacted, reaction was carried out to after 30-35 minutes, controlled reaction temperature in 88-90 DEG C of range, the reaction was continued
40-50 minutes;Remaining formaldehyde is added in reaction system by second step, is reacted 35-40 minutes under 85-88 DEG C of range, from
It so is cooled to 34-36 DEG C, it can plastic emitting;The preparation method of the modified catalyst the following steps are included:
(1) 18.5-18.7 grams of Zinc diacetate dihydrate and 1.9-2.0 grams of nano-titanium dioxide are weighed, is added sequentially to equipped with 150-
In the beaker of 160 milliliters of dehydrated alcohols, beaker is placed on magnetic stirring apparatus, is stirred 45-50 minutes, is then added dropwise dropwise
Ammonia spirit, regulation system pH value is between 9.8-10.0, then places the beaker heat preservation in 70-80 DEG C of insulating box and place 10-
12 hours;
(2) standing mixt in step (1) is taken out, is poured into four-hole boiling flask, lower water-bath is stirred and is heated to 45-55 DEG C, to
7.5-8.0 milliliters of vinyl trichlorosilanes are added in flask, 3.0-3.4 grams of polyvinyl alcohol is added after stirring evenly into flask,
Warming-in-water is heated to 85-90 DEG C, and persistently stirring is lower carries out insulation reaction, reaction to dropwise addition acetum body after 30-40 minutes
It is pH value between 7.4-7.6, is cooled to 60-65 DEG C, continues insulation reaction 1.0-2.0 hours, after reaction, filter and make
It is washed with deionized to obtain solid reaction product, be subsequently placed in drying box small with the dry 10-12 of 75-80 DEG C of Temperature Vacuum
When, place into 380-400 DEG C of resistance furnace high temperature heating and calcining 30-40 minutes, grinding obtains powder after cooling to room temperature with the furnace
Shape product is the modified catalyst.
It is further described as to above scheme, step (1) the ammonia spirit pH value is between 11.0-11.2.
It is further described as to above scheme, step (2) the acetum mass concentration is 24-28%.
It is further described as to above scheme, step (2) the modified catalyst particle size being prepared exists
Between 75-80 nanometers.
It is further described as to above scheme, the modified catalyst dosage is the 0.55-0.60% of formaldehyde quality.
The present invention has the advantage that compared with prior art in order to solve the problems, such as that existing phenolic resin adhesive exists, this hair
Bright to provide a kind of method for improving phenolic resin adhesive curing rate, during phenolic resin preparation, phenolic aldehyde is pressed with formaldehyde
It is reacted according to the proportion that molar ratio is 1:1.9-2.0, the first step is added the modified catalyst being prepared, is reacted;The
Remaining formaldehyde is added in reaction system by two steps, by catalytic modification, reduces space steric effect, it is adjacent to improve phenol
Position reactivity, inhibits the generation of gaseous aldehyde, successfully improves its curing performance and thermal stability, overcome existing phenolic aldehyde
Resin adhesive since water content is higher, be obstructed by water diffusion, and curing rate is slow, the problem of stability difference, and durability
With bonding strength height, the resistance of temperature is improved, significantly extends the service life of phenolic resin adhesive, material it is resistance to
The comprehensive performances such as mill, heat-resisting, adhesiveness are significantly increased compared with existing level, and when film forming and physical mechanical property obtain long
Between ensure, the method for the raising phenolic resin adhesive curing rate that the present invention uses solves existing phenolic resin adhesive and deposits
The problem of, keep higher curing rate, taken into account the promotion of service performance and service life, improve phenolic resin gluing
The development and utilization of agent composite material can be realized the extension phenolic resin adhesive materials'use service life and extend its suitable application area
Realistic meaning, be a kind of technical solution being extremely worth of widely use.
Specific embodiment
To make the purpose of the present invention, technical solution and effect clearer, clear and definite, combined with specific embodiments below to this hair
It is bright to be described further, it should be understood that the specific embodiments described herein are merely illustrative of the present invention, is not used to limit
Technical solution provided by the present invention.
Embodiment 1
A method of phenolic resin adhesive curing rate being improved, during phenolic resin preparation, phenolic aldehyde and formaldehyde are according to rubbing
, than being that the proportion of 1:1.9 is reacted, whole phenolic resin is added in three-necked flask, matter is then added by the first step for you
The modified catalyst being prepared is added after mixing in the formaldehyde that amount percentage is 17%, and heating is closed after being warming up to 66 DEG C
Device is reacted, and reaction was carried out to after 30 minutes, is controlled reaction temperature in 88-90 DEG C of range, is continued the reaction for 40 minutes;Second
Step, remaining formaldehyde is added in reaction system, reacts 35 minutes under 85-88 DEG C of range, naturally cools to 34 DEG C
Plastic emitting;The preparation method of the modified catalyst the following steps are included:
(1) 18.5 grams of Zinc diacetate dihydrates and 1.9 grams of nano-titanium dioxides are weighed, are added sequentially to equipped with 150 milliliters of anhydrous second
In the beaker of alcohol, beaker is placed on magnetic stirring apparatus, is stirred 45 minutes, ammonia spirit is then added dropwise dropwise, adjusts body
It is pH value between 9.8-10.0, then places the beaker heat preservation in 70 DEG C of insulating box and place 10 hours;
(2) standing mixt in step (1) is taken out, is poured into four-hole boiling flask, lower water-bath is stirred and is heated to 45 DEG C, to flask
3.0 grams of polyvinyl alcohol, warming-in-water heating is added in 7.5 milliliters of vinyl trichlorosilanes of middle addition into flask after stirring evenly
To 85 DEG C, lasting stirring is lower to carry out insulation reaction, reaction to be added dropwise after 30 minutes acetum system pH 7.4-7.6 it
Between, it is cooled to 60 DEG C, continues insulation reaction 1.0 hours, after reaction, filter and make to be washed with deionized to obtain solid anti-
Product is answered, is subsequently placed in drying box with Temperature Vacuum drying 10 hours of 75 DEG C, places into 380 DEG C of resistance furnace high temperatures heating
Calcining 30 minutes, cooling to after room temperature that grinding obtains powdery product with the furnace is the modified catalyst.
It is further described as to above scheme, step (1) the ammonia spirit pH value is between 11.0-11.2.
It is further described as to above scheme, step (2) the acetum mass concentration is 24%.
It is further described as to above scheme, step (2) the modified catalyst particle size being prepared exists
Between 75-80 nanometers.
It is further described as to above scheme, the modified catalyst dosage is the 0.55% of formaldehyde quality.
Embodiment 2
A method of phenolic resin adhesive curing rate being improved, during phenolic resin preparation, phenolic aldehyde and formaldehyde are according to rubbing
, than being that the proportion of 1:1.95 is reacted, whole phenolic resin is added in three-necked flask, matter is then added by the first step for you
The modified catalyst being prepared is added after mixing in the formaldehyde that amount percentage is 18.5%, closes and adds after being warming up to 67 DEG C
Hot device is reacted, and reaction was carried out to after 32 minutes, controls reaction temperature in 88-90 DEG C of range, the reaction was continued 45 minutes;Second
Step, remaining formaldehyde is added in reaction system, reacts 38 minutes under 85-88 DEG C of range, naturally cools to 35 DEG C
Plastic emitting;The preparation method of the modified catalyst the following steps are included:
(1) 18.6 grams of Zinc diacetate dihydrates and 1.95 grams of nano-titanium dioxides are weighed, are added sequentially to equipped with 155 milliliters of anhydrous second
In the beaker of alcohol, beaker is placed on magnetic stirring apparatus, is stirred 48 minutes, ammonia spirit is then added dropwise dropwise, adjusts body
It is pH value between 9.8-10.0, then places the beaker heat preservation in 75 DEG C of insulating box and place 11 hours;
(2) standing mixt in step (1) is taken out, is poured into four-hole boiling flask, lower water-bath is stirred and is heated to 50 DEG C, to flask
3.2 grams of polyvinyl alcohol, warming-in-water heating is added in 7.8 milliliters of vinyl trichlorosilanes of middle addition into flask after stirring evenly
To 87 DEG C, lasting stirring is lower to carry out insulation reaction, reaction to be added dropwise after 35 minutes acetum system pH 7.4-7.6 it
Between, it is cooled to 63 DEG C, continues insulation reaction 1.5 hours, after reaction, filter and make to be washed with deionized to obtain solid anti-
Product is answered, is subsequently placed in drying box with Temperature Vacuum drying 11 hours of 78 DEG C, places into 390 DEG C of resistance furnace high temperatures heating
Calcining 35 minutes, cooling to after room temperature that grinding obtains powdery product with the furnace is the modified catalyst.
It is further described as to above scheme, step (1) the ammonia spirit pH value is between 11.0-11.2.
It is further described as to above scheme, step (2) the acetum mass concentration is 26%.
It is further described as to above scheme, step (2) the modified catalyst particle size being prepared exists
Between 75-80 nanometers.
It is further described as to above scheme, the modified catalyst dosage is the 0.58% of formaldehyde quality.
Embodiment 3
A method of phenolic resin adhesive curing rate being improved, during phenolic resin preparation, phenolic aldehyde and formaldehyde are according to rubbing
, than being that the proportion of 1:2.0 is reacted, whole phenolic resin is added in three-necked flask, matter is then added by the first step for you
The modified catalyst being prepared is added after mixing in the formaldehyde that amount percentage is 20%, and heating is closed after being warming up to 68 DEG C
Device is reacted, and reaction was carried out to after 35 minutes, controls reaction temperature in 88-90 DEG C of range, the reaction was continued 50 minutes;Second
Step, remaining formaldehyde is added in reaction system, reacts 40 minutes under 85-88 DEG C of range, naturally cools to 36 DEG C
Plastic emitting;The preparation method of the modified catalyst the following steps are included:
(1) 18.7 grams of Zinc diacetate dihydrates and 2.0 grams of nano-titanium dioxides are weighed, are added sequentially to equipped with 160 milliliters of anhydrous second
In the beaker of alcohol, beaker is placed on magnetic stirring apparatus, is stirred 50 minutes, ammonia spirit is then added dropwise dropwise, adjusts body
It is pH value between 9.8-10.0, then places the beaker heat preservation in 80 DEG C of insulating box and place 12 hours;
(2) standing mixt in step (1) is taken out, is poured into four-hole boiling flask, lower water-bath is stirred and is heated to 55 DEG C, to flask
3.4 grams of polyvinyl alcohol, warming-in-water heating is added in 8.0 milliliters of vinyl trichlorosilanes of middle addition into flask after stirring evenly
To 90 DEG C, lasting stirring is lower to carry out insulation reaction, reaction to be added dropwise after forty minutes acetum system pH 7.4-7.6 it
Between, it is cooled to 65 DEG C, continues insulation reaction 2.0 hours, after reaction, filter and make to be washed with deionized to obtain solid anti-
Product is answered, is subsequently placed in drying box with Temperature Vacuum drying 12 hours of 80 DEG C, places into 400 DEG C of resistance furnace high temperatures heating
Calcining 40 minutes, cooling to after room temperature that grinding obtains powdery product with the furnace is the modified catalyst.
It is further described as to above scheme, step (1) the ammonia spirit pH value is between 11.0-11.2.
It is further described as to above scheme, step (2) the acetum mass concentration is 28%.
It is further described as to above scheme, step (2) the modified catalyst particle size being prepared exists
Between 75-80 nanometers.
It is further described as to above scheme, the modified catalyst dosage is the 0.60% of formaldehyde quality.
Comparative example 1
Difference with embodiment 1 is only that, during phenolic resin preparation, phenolic aldehyde and formaldehyde are matching for 1:2.5 according to molar ratio
Than being reacted, remaining is consistent.
Comparative example 2
Difference with embodiment 2 is only that, in the preparation of phenolic acid Resin adhesive, replaces the modification in the application to urge using zinc acetate
Agent, remaining is consistent.
Comparative example 3
Difference with embodiment 3 is only that in the preparation of phenolic acid Resin adhesive, the first that mass percent is 30% is added in the first step
Aldehyde, remaining is consistent.
Comparative example 4
Difference with embodiment 3 is only that, in the preparation of the modified catalyst, omits the addition of the nano-titanium dioxide,
Remaining is consistent.
Comparative example 5
Difference with embodiment 3 is only that, in the preparation of the modified catalyst, omits adding for the vinyl trichlorosilane
Add, remaining is consistent.
Comparative experiments
Phenolic resin adhesive curing rate is improved using the method for embodiment 1-3 and comparative example 1-5 respectively, with patent publication No.
For a kind of boron modified phenolic resin adhesive disclosed in CN106675470A preparation method as a control group, according to each group method
Processing prepares phenolic resin adhesive, carries out performance detection, to the phenolic resin being prepared carry out bonding strength performance and
Curing performance compares, in bonding strength performance test, by each group adhesive to having a size of (500 millimeters × 500 millimeters × 1.5 millis
Rice) glued board carries out gluing, three layers of glued plate sample are prepared, at 120 DEG C, the glue that hot pressing obtains after 8 minutes under 1.3MPa
Plywood is further cut into sample (having a size of 100 millimeters × 25 millimeters), balances 24 hours at 25 DEG C, be placed in 100 DEG C of boiling water
It is middle to impregnate 2 hours, it is then hung at 25 DEG C 15 minutes, reuses general-purpose mechanics machine and carry out bonding strength performance test,
Specific test method keeps in test that irrelevant variable is consistent referring to GB/T 17657-2013, counts effective average value, as a result such as
Shown in following table:
(burst size of methanal is measured using condensed steam water, and the measuring method of curing time is according to GB/T 14072-2006;)
The method for the raising phenolic resin adhesive curing rate that the present invention uses solves existing phenolic resin adhesive and exists
The problem of, higher curing rate is kept, the promotion of service performance and service life has been taken into account, has improved phenolic resin adhesive
The development and utilization of composite material can be realized the extension phenolic resin adhesive materials'use service life and extend its suitable application area
Realistic meaning is a kind of technical solution being extremely worth of widely use.
Claims (5)
1. a kind of method for improving phenolic resin adhesive curing rate, which is characterized in that during phenolic resin preparation, phenolic aldehyde
It is reacted with formaldehyde according to the proportion that molar ratio is 1:1.9-2.0, whole phenolic resin is added to three mouthfuls of burnings by the first step
In bottle, the formaldehyde that mass percent is 17-20% is then added, the modified catalyst being prepared is added after mixing, rise
Temperature to closing heater after 66-68 DEG C is reacted, and reaction was carried out to after 30-35 minutes, controlled reaction temperature in 88-90 DEG C of model
It encloses, the reaction was continued 40-50 minutes;Remaining formaldehyde is added in reaction system by second step, is reacted under 85-88 DEG C of range
35-40 minutes, 34-36 DEG C is naturally cooled to, it can plastic emitting;The preparation method of the modified catalyst the following steps are included:
(1) 18.5-18.7 grams of Zinc diacetate dihydrate and 1.9-2.0 grams of nano-titanium dioxide are weighed, is added sequentially to equipped with 150-
In the beaker of 160 milliliters of dehydrated alcohols, beaker is placed on magnetic stirring apparatus, is stirred 45-50 minutes, is then added dropwise dropwise
Ammonia spirit, regulation system pH value is between 9.8-10.0, then places the beaker heat preservation in 70-80 DEG C of insulating box and place 10-
12 hours;
(2) standing mixt in step (1) is taken out, is poured into four-hole boiling flask, lower water-bath is stirred and is heated to 45-55 DEG C, to
7.5-8.0 milliliters of vinyl trichlorosilanes are added in flask, 3.0-3.4 grams of polyvinyl alcohol is added after stirring evenly into flask,
Warming-in-water is heated to 85-90 DEG C, and persistently stirring is lower carries out insulation reaction, reaction to dropwise addition acetum body after 30-40 minutes
It is pH value between 7.4-7.6, is cooled to 60-65 DEG C, continues insulation reaction 1.0-2.0 hours, after reaction, filter and make
It is washed with deionized to obtain solid reaction product, be subsequently placed in drying box small with the dry 10-12 of 75-80 DEG C of Temperature Vacuum
When, place into 380-400 DEG C of resistance furnace high temperature heating and calcining 30-40 minutes, grinding obtains powder after cooling to room temperature with the furnace
Shape product is the modified catalyst.
2. a kind of method for improving phenolic resin adhesive curing rate as described in claim 1, which is characterized in that step (1)
The ammonia spirit pH value is between 11.0-11.2.
3. a kind of method for improving phenolic resin adhesive curing rate as described in claim 1, which is characterized in that step (2)
The acetum mass concentration is 24-28%.
4. a kind of method for improving phenolic resin adhesive curing rate as described in claim 1, which is characterized in that step (2)
The modified catalyst particle size being prepared is between 75-80 nanometers.
5. a kind of method for improving phenolic resin adhesive curing rate as described in claim 1, which is characterized in that the modification
Catalyst amount is the 0.55-0.60% of formaldehyde quality.
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109385215A (en) * | 2018-10-23 | 2019-02-26 | 含山县领创新材料科技有限公司 | A kind of building water-proof anticracking gel rubber material |
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CN109385215A (en) * | 2018-10-23 | 2019-02-26 | 含山县领创新材料科技有限公司 | A kind of building water-proof anticracking gel rubber material |
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