CN109486466A - A method of improving dimer acid polyamide adhesive adhesive property - Google Patents
A method of improving dimer acid polyamide adhesive adhesive property Download PDFInfo
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- CN109486466A CN109486466A CN201811406446.9A CN201811406446A CN109486466A CN 109486466 A CN109486466 A CN 109486466A CN 201811406446 A CN201811406446 A CN 201811406446A CN 109486466 A CN109486466 A CN 109486466A
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- dimer acid
- acid polyamide
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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
- C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
- C09J177/06—Polyamides derived from polyamines and polycarboxylic acids
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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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
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- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyamides (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention relates to new function material technical fields, disclose a kind of method for improving dimer acid polyamide adhesive adhesive property, in dimer acid polyamide preparation process, first dimer acid material is added in four-hole boiling flask, the active catalyst being prepared is added dropwise with 40-45 drop/minute speed and carries out polycondensation reaction, catalytic polymerization is carried out using the active catalyst being prepared, it can reduce polymerization temperature, reduce the formation of imidazole ring, the viscosity of resin will not be greatly reduced with the raising of reaction temperature, the hydrogen bond number of product structure is increased simultaneously, improve intermolecular linkage resultant force, reinforce the thermo oxidative stability of polymer, improve the wetting ability of adhesive, to enhance caking property, existing dimer acid polyamide adhesive is overcome in viscosity, insufficient problem present on mechanical property and softening point, Significantly extend the service life of dimer acid polyamide adhesive.
Description
Technical field
The invention belongs to new function material technical fields, and in particular to a kind of raising dimer acid polyamide adhesive bonding
The method of performance.
Background technique
Dimer acid polyamide adhesive is reacted with polyamine through pyrocondensation by dimeric dibasic acid.Dimer acid polyamide gluing
Agent belongs to one kind of hot melt adhesive, and hot melt adhesive refers to excellent cementability, is at room temperature in solid-state, but work as and be heated to its fusing point
It is in a liquid state when left and right, and can form high-intensitive bonding after cooling rapidly together with other adhering objects.Due to hot melt
Glue is not necessarily to solvent flashing in use, therefore does not pollute the environment, and is conducive to the regeneration of resource and the protection of environment；And
Hot melt adhesive product can be made into bulk, film-form, strip or granular, and packaging, storing and use are all extremely convenient；In addition, hot melt
Adhesive is easy to use, and adhering speed is fast, is suitble to the automated production operation of the modern industrial sector and wanting for high production efficiency
It asks.
Dimer acid polyamide adhesive has rapid bonding, nonhazardous and has the spies such as bonding well to polar material
Point, is widely used, and applies in general to the bonding between the different materials such as metal, glass, plastics, timber, industrial to have very
Good application prospect.And the basic model dimer acid polyamide adhesive of existing synthesis is in viscosity, mechanical property and softening point
On there are the insufficient disadvantages of performance, this is because resin reaction of salt-forming stage in synthesis is incomplete, due to reaction temperature compared with
Height, leads in polymerization reaction that carboxyl cannot sufficiently react in dimer acid material, prevent acid value is from being effectively reduced, the amine of product
It is worth higher.
Summary of the invention
The purpose of the present invention is being directed to existing problem, a kind of raising dimer acid polyamide adhesive adhesive property is provided
Method, overcome existing dimer acid polyamide adhesive in problem insufficient present on viscosity, mechanical property and softening point,
And wash resistant, salt tolerant, resistance to acid and alkali are high, improve to the resistance of temperature.
The present invention is achieved by the following technical solutions:
A method of dimer acid polyamide adhesive adhesive property being improved, in dimer acid polyamide preparation process, first by two
Polyacids raw material is added in the four-hole boiling flask equipped with agitating device, nitrogen protection device, thermometer and water segregator, with 7-8 DEG C/minute
The speed of clock is warming up to 80-90 DEG C, and the active catalyst being prepared is added dropwise with 40-45 drop/minute speed, drips subsequent
The continuous speed with 4-5 DEG C/min is warming up to 130-135 DEG C, and ethylenediamine is added dropwise under insulated and stirred and carries out constant temperature prepolymerization reaction 45-
50 minutes, it then is warming up to 180-185 DEG C with 5-6 DEG C/min of speed, continues insulated and stirred reaction 2.5-2.8 hours, finally
It carries out vacuumizing decompression polycondensation 25-30 minutes, blowing can be carried out by naturally cooling to 150-155 DEG C；The active catalyst
Preparation method the following steps are included:
(1) it weighs 5.56-5.60 grams of zinc nitrate to be put into clean beaker, 60-70 ml deionized water is added under stiring,
It is made into zinc nitrate aqueous solution, 35-40 milliliters of phosphate aqueous solutions are added into beaker, place the beaker on magnetic stirring apparatus, is continued
It is uniformly mixed within stirring 25-30 minutes, heating water bath is warming up to 48-50 DEG C, and 2.4-2.6 grams of two silicon nitrogen of hexamethyl is added dropwise under stiring
Alkane；
(2) step (1) mixed liquor is transferred in round-bottomed flask, is warming up to 56-60 DEG C, in 270-300 revs/min of stirring speed
1.0-1.2 ml acetic anhydride is slowly added dropwise with 20-30 drop/minute speed under degree, is continuously heating to 72-75 DEG C after dripping,
Return stirring reacts 1.0-1.4 hours under nitrogen protection, is placed in ice-water bath is cooled to 20-24 DEG C after reaction.
It is further described as to above scheme, it is single in dimer acid material in the dimer acid polyamide preparation process
Body acid content is between 4.8-5.0%.
It is further described as to above scheme, in the dimer acid polyamide preparation process, temperature when vacuumizing decompression
Degree is in 170-175 DEG C of range.
It is further described as to above scheme, step (1) the phosphate aqueous solution pH value is between 4.5-4.6.
It is further described as to above scheme, in the dimer acid polyamide preparation process, dimeric dibasic acid and ethylenediamine
Reaction mass ratio is 11-12:1.
It is further described as to above scheme, the active catalyst dosage is the 0.13- of dimeric dibasic acid quality
0.15%。
The present invention has the advantage that there are caking property in order to solve existing dimer acid polyamide adhesive not compared with prior art
The problem of foot, the present invention provides a kind of methods for improving dimer acid polyamide adhesive adhesive property, use what is be prepared
Active catalyst carries out catalytic polymerization, can reduce polymerization temperature, reduces the formation of imidazole ring, and the viscosity of resin will not be with
The raising of reaction temperature and be greatly reduced, while increasing the hydrogen bond number of product structure, improve intermolecular linkage resultant force, reinforce
The thermo oxidative stability of polymer, improves the wetting ability of adhesive, to enhance caking property, overcomes existing dimeric dibasic acid
Polyamide adhesive is in problem insufficient present on viscosity, mechanical property and softening point, and wash resistant, salt tolerant, acid and alkali-resistance
Property it is high, the resistance of temperature is improved, significantly extends the service life of dimer acid polyamide adhesive, gluing agent material it is resistance to
The comprehensive performances such as mill, antidetonation, resistance to dust are significantly increased compared with existing level, and when film forming and physical mechanical property obtain long
Between ensure, the method for the raising dimer acid polyamide adhesive adhesive property that the present invention uses solves existing dimer acid polyamide
Adhesive there are the problem of, keep higher binding speed, taken into account the promotion of adhesive property and service life, improved dimerization
The development and utilization of sour polyamide adhesive composite material, can be realized extend the dimer acid polyamide adhesive materials'use service life with
And the realistic meaning of its suitable application area is extended, it is 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 dimer acid polyamide adhesive adhesive property being improved, in dimer acid polyamide preparation process, first by two
Polyacids raw material is added in the four-hole boiling flask equipped with agitating device, nitrogen protection device, thermometer and water segregator, with 7 DEG C/min
Speed be warming up to 80 DEG C, the active catalyst that is prepared is added dropwise with 40 drops/minute speed, continue after dripping with 4 DEG C/
Minute speed be warming up to 130 DEG C, under insulated and stirred be added dropwise ethylenediamine carry out constant temperature prepolymerization reaction 45 minutes, then with 5 DEG C/
The speed of minute is warming up to 180 DEG C, continues insulated and stirred and reacts 2.5 hours, finally carries out vacuumizing decompression polycondensation 25 minutes, from
So blowing can be carried out by being cooled to 150 DEG C；The preparation method of the active catalyst the following steps are included:
(1) it weighs 5.56 grams of zinc nitrate to be put into clean beaker, 60 ml deionized waters is added under stiring, are made into nitric acid
35 milliliters of phosphate aqueous solutions are added into beaker, place the beaker on magnetic stirring apparatus for zinc aqueous solution, persistently stir 25 minutes and mix
It closes uniformly, heating water bath is warming up to 48 DEG C, and 2.4 grams of hexamethyldisilazane are added dropwise under stiring；
(2) step (1) mixed liquor is transferred in round-bottomed flask, is warming up to 56 DEG C, under 270 revs/min of mixing speed with
1.0 ml acetic anhydrides are slowly added dropwise in 20 drops/minute speed, and 72 DEG C are continuously heating to after dripping, is flowed back under nitrogen protection
It is stirred to react 1.0 hours, is placed in ice-water bath after reaction and is cooled to 20 DEG C.
It is further described as to above scheme, it is single in dimer acid material in the dimer acid polyamide preparation process
Body acid content is between 4.8-5.0%.
It is further described as to above scheme, in the dimer acid polyamide preparation process, temperature when vacuumizing decompression
Degree is in 170-175 DEG C of range.
It is further described as to above scheme, step (1) the phosphate aqueous solution pH value is between 4.5-4.6.
It is further described as to above scheme, in the dimer acid polyamide preparation process, dimeric dibasic acid and ethylenediamine
Reaction mass ratio is 11:1.
It is further described as to above scheme, the active catalyst dosage is the 0.13% of dimeric dibasic acid quality.
Embodiment 2
A method of dimer acid polyamide adhesive adhesive property being improved, in dimer acid polyamide preparation process, first by two
Polyacids raw material is added in the four-hole boiling flask equipped with agitating device, nitrogen protection device, thermometer and water segregator, with 7.5 DEG C/minute
The speed of clock is warming up to 85 DEG C, and the active catalyst that is prepared is added dropwise with 42 drops/minute speed, continue after dripping with
4.5 DEG C/min of speed is warming up to 132 DEG C, ethylenediamine progress constant temperature prepolymerization reaction 48 minutes is added dropwise under insulated and stirred, then
182 DEG C are warming up to 5.5 DEG C/min of speed, continues insulated and stirred and reacts 2.6 hours, finally carry out vacuumizing decompression polycondensation
28 minutes, blowing can be carried out by naturally cooling to 152 DEG C；The preparation method of the active catalyst the following steps are included:
(1) it weighs 5.58 grams of zinc nitrate to be put into clean beaker, 65 ml deionized waters is added under stiring, are made into nitric acid
38 milliliters of phosphate aqueous solutions are added into beaker, place the beaker on magnetic stirring apparatus for zinc aqueous solution, persistently stir 28 minutes and mix
It closes uniformly, heating water bath is warming up to 49 DEG C, and 2.5 grams of hexamethyldisilazane are added dropwise under stiring；
(2) step (1) mixed liquor is transferred in round-bottomed flask, is warming up to 58 DEG C, under 280 revs/min of mixing speed with
1.1 ml acetic anhydrides are slowly added dropwise in 25 drops/minute speed, and 73 DEG C are continuously heating to after dripping, is flowed back under nitrogen protection
It is stirred to react 1.2 hours, is placed in ice-water bath after reaction and is cooled to 22 DEG C.
It is further described as to above scheme, it is single in dimer acid material in the dimer acid polyamide preparation process
Body acid content is between 4.8-5.0%.
It is further described as to above scheme, in the dimer acid polyamide preparation process, temperature when vacuumizing decompression
Degree is in 170-175 DEG C of range.
It is further described as to above scheme, step (1) the phosphate aqueous solution pH value is between 4.5-4.6.
It is further described as to above scheme, in the dimer acid polyamide preparation process, dimeric dibasic acid and ethylenediamine
Reaction mass ratio is 11.5:1.
It is further described as to above scheme, the active catalyst dosage is the 0.14% of dimeric dibasic acid quality.
Embodiment 3
A method of dimer acid polyamide adhesive adhesive property being improved, in dimer acid polyamide preparation process, first by two
Polyacids raw material is added in the four-hole boiling flask equipped with agitating device, nitrogen protection device, thermometer and water segregator, with 8 DEG C/min
Speed be warming up to 90 DEG C, the active catalyst that is prepared is added dropwise with 45 drops/minute speed, continue after dripping with 5 DEG C/
Minute speed be warming up to 135 DEG C, under insulated and stirred be added dropwise ethylenediamine carry out constant temperature prepolymerization reaction 50 minutes, then with 6 DEG C/
The speed of minute is warming up to 185 DEG C, continues insulated and stirred and reacts 2.8 hours, finally carries out vacuumizing decompression polycondensation 30 minutes, from
So blowing can be carried out by being cooled to 155 DEG C；The preparation method of the active catalyst the following steps are included:
(1) it weighs 5.60 grams of zinc nitrate to be put into clean beaker, 70 ml deionized waters is added under stiring, are made into nitric acid
40 milliliters of phosphate aqueous solutions are added into beaker, place the beaker on magnetic stirring apparatus for zinc aqueous solution, persistently stir 30 minutes and mix
It closes uniformly, heating water bath is warming up to 50 DEG C, and 2.6 grams of hexamethyldisilazane are added dropwise under stiring；
(2) step (1) mixed liquor is transferred in round-bottomed flask, is warming up to 60 DEG C, under 300 revs/min of mixing speed with
1.2 ml acetic anhydrides are slowly added dropwise in 30 drops/minute speed, and 75 DEG C are continuously heating to after dripping, is flowed back under nitrogen protection
It is stirred to react 1.4 hours, is placed in ice-water bath after reaction and is cooled to 24 DEG C.
It is further described as to above scheme, it is single in dimer acid material in the dimer acid polyamide preparation process
Body acid content is between 4.8-5.0%.
It is further described as to above scheme, in the dimer acid polyamide preparation process, temperature when vacuumizing decompression
Degree is in 170-175 DEG C of range.
It is further described as to above scheme, step (1) the phosphate aqueous solution pH value is between 4.5-4.6.
It is further described as to above scheme, in the dimer acid polyamide preparation process, dimeric dibasic acid and ethylenediamine
Reaction mass ratio is 12:1.
It is further described as to above scheme, the active catalyst dosage is the 0.15% of dimeric dibasic acid quality.
Comparative example 1
Difference with embodiment 1 is only that, in dimer acid polyamide preparation process, prepolymerization reaction temperature is 140 DEG C, remaining guarantor
It holds consistent.
Comparative example 2
Difference with embodiment 2 is only that, in the preparation of phenolic acid Resin adhesive, 240 DEG C is warming up to after prepolymerization reaction, reaction 3
Hour, remaining is consistent.
Comparative example 3
Difference with embodiment 3 is only that, in dimer acid polyamide preparation process, is replaced using the phosphate aqueous solution of same concentrations
Activated catalyst in the application, remaining is consistent.
Comparative example 4
Difference with embodiment 3 is only that, in the preparation of the activated catalyst, the preparation for omitting the zinc nitrate aqueous solution adds
Add, remaining is consistent.
Comparative example 5
Difference with embodiment 3 is only that, in the preparation of the activated catalyst, omits the addition of the acetic anhydride, remaining guarantor
It holds consistent.
Comparative experiments
Dimer acid polyamide adhesive adhesive property is improved using the method for embodiment 1-3 and comparative example 1-5 respectively, is with pH value
It is that 10:1 carries out polymerization reaction, prepolymerization that 4.0 phosphate aqueous solution, which is catalyst, dimeric dibasic acid and ethylenediamine according to mass ratio,
Temperature is 140 DEG C, and then heating to 230 DEG C, the reaction was continued 3 hours, and the method for finally carrying out vacuumizing decompression polycondensation 40 minutes is made
For control group, preparation dimer acid polyamide adhesive is processed according to each group method, performance detection is carried out, to the dimerization being prepared
Sour polyamide carries out adhesion strength performance and compares, and obtained experimental data is the average value of 5 samples, keeps irrelevant variable in test
Unanimously, effective average value is counted, as a result as shown in the table:
| Project | Tensile strength (MPa) | Softening point (DEG C) | Viscosity (mpa.s) |
| Embodiment 1 | 18.9 | 140 | 3936 |
| Embodiment 2 | 19.1 | 141 | 3955 |
| Embodiment 3 | 19.0 | 140 | 3940 |
| Comparative example 1 | 12.4 | 122 | 2830 |
| Comparative example 2 | 11.2 | 116 | 2795 |
| Comparative example 3 | 8.6 | 108 | 2560 |
| Comparative example 4 | 13.5 | 127 | 3052 |
| Comparative example 5 | 14.8 | 133 | 3340 |
| Control group | 7.6 | 104 | 896 |
(measurement of tensile strength is tested at rate of extension 5Omm/min according to ASTME-D638 standard, using universal testing machine
The tensile strength of sample；The measurement of softening point is according to GB 12007.6-1989, using the softening point of ring and ball method measurement product；It is viscous
Degree measurement is measured product viscosity using rotational viscometer according to GB/T 2794-1995 standard.)
The method for the raising dimer acid polyamide adhesive adhesive property that the present invention uses solves existing dimer acid polyamide glue
Glutinous agent there are the problem of, keep higher binding speed, taken into account the promotion of adhesive property and service life, improved dimeric dibasic acid
The development and utilization of polyamide adhesive composite material, can be realized extend the dimer acid polyamide adhesive materials'use service life and
The realistic meaning for extending its suitable application area is a kind of technical solution being extremely worth of widely use.
Claims (6)
1. a kind of method for improving dimer acid polyamide adhesive adhesive property, which is characterized in that prepared in dimer acid polyamide
In the process, dimer acid material is first added to the four-hole boiling flask equipped with agitating device, nitrogen protection device, thermometer and water segregator
In, it is warming up to 80-90 DEG C with 7-8 DEG C/min of speed, the active catalytic being prepared is added dropwise with 40-45 drop/minute speed
Agent is continued to be warming up to 130-135 DEG C with 4-5 DEG C/min of speed after dripping, ethylenediamine is added dropwise under insulated and stirred and carries out constant temperature
Prepolymerization reaction 45-50 minutes, it then is warming up to 180-185 DEG C with 5-6 DEG C/min of speed, continues insulated and stirred reaction
It 2.5-2.8 hours, finally carries out vacuumizing decompression polycondensation 25-30 minutes, blowing can be carried out by naturally cooling to 150-155 DEG C；
The preparation method of the active catalyst the following steps are included:
(1) it weighs 5.56-5.60 grams of zinc nitrate to be put into clean beaker, 60-70 ml deionized water is added under stiring,
It is made into zinc nitrate aqueous solution, 35-40 milliliters of phosphate aqueous solutions are added into beaker, place the beaker on magnetic stirring apparatus, is continued
It is uniformly mixed within stirring 25-30 minutes, heating water bath is warming up to 48-50 DEG C, and 2.4-2.6 grams of two silicon nitrogen of hexamethyl is added dropwise under stiring
Alkane；
(2) step (1) mixed liquor is transferred in round-bottomed flask, is warming up to 56-60 DEG C, in 270-300 revs/min of stirring speed
1.0-1.2 ml acetic anhydride is slowly added dropwise with 20-30 drop/minute speed under degree, is continuously heating to 72-75 DEG C after dripping,
Return stirring reacts 1.0-1.4 hours under nitrogen protection, is placed in ice-water bath is cooled to 20-24 DEG C after reaction.
2. a kind of method for improving dimer acid polyamide adhesive adhesive property as described in claim 1, which is characterized in that described
In dimer acid polyamide preparation process, monomeric acid content is between 4.8-5.0% in dimer acid material.
3. a kind of method for improving dimer acid polyamide adhesive adhesive property as described in claim 1, which is characterized in that described
In dimer acid polyamide preparation process, temperature is in 170-175 DEG C of range when vacuumizing decompression.
4. a kind of method for improving dimer acid polyamide adhesive adhesive property as described in claim 1, which is characterized in that step
(1) the phosphate aqueous solution pH value is between 4.5-4.6.
5. a kind of method for improving dimer acid polyamide adhesive adhesive property as described in claim 1, which is characterized in that described
In dimer acid polyamide preparation process, dimeric dibasic acid and reacting ethylenediamine mass ratio are 11-12:1.
6. a kind of method for improving dimer acid polyamide adhesive adhesive property as described in claim 1, which is characterized in that described
Active catalyst dosage is the 0.13-0.15% of dimeric dibasic acid quality.
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| CN201811406446.9A CN109486466A (en) | 2018-11-23 | 2018-11-23 | A method of improving dimer acid polyamide adhesive adhesive property |
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| CN201811406446.9A CN109486466A (en) | 2018-11-23 | 2018-11-23 | A method of improving dimer acid polyamide adhesive adhesive property |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101928544A (en) * | 2010-09-21 | 2010-12-29 | 烟台德邦电子材料有限公司 | Polyamide hot cement with high softening point and low-temperature resistance, and preparing method thereof |
| CN102807837A (en) * | 2012-07-31 | 2012-12-05 | 烟台德邦科技有限公司 | Low-temperature-resistant dimer acid type polyamide hot melt adhesive and preparation method thereof |
| CN107556965A (en) * | 2017-09-20 | 2018-01-09 | 华特粘接材料股份有限公司 | High temperature resistant copolyamide PUR and processing method for footwear material |
-
2018
- 2018-11-23 CN CN201811406446.9A patent/CN109486466A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101928544A (en) * | 2010-09-21 | 2010-12-29 | 烟台德邦电子材料有限公司 | Polyamide hot cement with high softening point and low-temperature resistance, and preparing method thereof |
| CN102807837A (en) * | 2012-07-31 | 2012-12-05 | 烟台德邦科技有限公司 | Low-temperature-resistant dimer acid type polyamide hot melt adhesive and preparation method thereof |
| CN107556965A (en) * | 2017-09-20 | 2018-01-09 | 华特粘接材料股份有限公司 | High temperature resistant copolyamide PUR and processing method for footwear material |
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