CN101962526A - Low-viscosity dimer acid type polyamine hot melt adhesive and preparation method thereof - Google Patents
Low-viscosity dimer acid type polyamine hot melt adhesive and preparation method thereof Download PDFInfo
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- CN101962526A CN101962526A CN2010102974363A CN201010297436A CN101962526A CN 101962526 A CN101962526 A CN 101962526A CN 2010102974363 A CN2010102974363 A CN 2010102974363A CN 201010297436 A CN201010297436 A CN 201010297436A CN 101962526 A CN101962526 A CN 101962526A
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Abstract
The invention relates to a low-viscosity dimer acid type polyamine hot melt adhesive and a preparation method thereof. The hot melt adhesive consists of the following raw materials in percentage by mole: 55 to 95 percent of dimer acid, 5 to 45 percent of aliphatic dibasic acid, 60 to 95 percent of aliphatic diamine, 5 to 40 percent of polyoxypropylene polyamine, 0.1 to 5 percent of molecular weight regulator, and the balance of water and antioxidant, wherein the dosage of the water accounts for 1 to 30 percent of the total mass of the acide and the amine; and the dosage of the antioxidant accounts for 0.1 to 2 percent of total mass of the acid and the amine. The preparation method comprises the following steps: salifying in the protection of nitrogen by using the dimer acid, the aliphatic dibasic acid and the diamine, the antioxidant and the molecular weight regulator as raw materials and introducing proper water at early stage; and heating and polycondensating. The polyamine hot melt adhesive has high and low temperature resistance, low high-temperature viscosity and simple molding process, and is mainly applied in automobile and electronic industries.
Description
Technical field
The present invention relates to a kind of low viscosity dimeric acid type polyamide hot melt adhesive and preparation method thereof, belong to the hotmelt field.
Background technology
Dimeric acid type polyamide hot melt adhesive is to be formed by dimeracid and diamine or polyamine condensation, various polar substrates all there is good adhesiveproperties, has snappiness preferably, applied range, environment-friendly solvent-free, chemical resistance and excellent advantages such as processability can be widely used in industries such as electronic apparatus, automobile, packing, machinery preferably.Yet common polyamide hot resistance to low temperature is poor, and softening temperature is also lower, and the high temperature viscosity height is unfavorable for moulding, can not satisfy the particular requirement of electronics, automobile and other industries.
Publication number provides a kind of synthetic method of dimer acid type polyamide resin for the patent of CN109887, the method that in reaction system, adds an amount of organic inert solvent by the initial period of reaction, solved the uppity shortcoming of initial stage volume, make system keep stable response behaviour in the early stage, and prevented the caking phenomenon that reaction system may occur, but used organic inert solvent in the invention, caused pollution easily environment.If melt phase polycondensation, in the process that early stage, aliphatic diamine dripped temperature raise very fast, and diamine highly volatile, its equivalent is difficult to control, repeatability is relatively poor.
Summary of the invention
The present invention is directed to the deficiencies in the prior art, a kind of low viscosity dimeric acid type polyamide hot melt adhesive and preparation method thereof is provided, so that it is high temperature resistant, low temperature flexibility is good, and high temperature viscosity is low, and good reproducibility is free from environmental pollution, and cost is low, is easy to produce.
The technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of low viscosity dimeric acid type polyamide hot melt adhesive, described hot melt adhesive is made up of each raw material of following molar percentage: dimeracid 55～95%, aliphatic dibasic acid 5～45%, aliphatic diamine 60～95%, polyether polyamine 5～40%, molecular weight regulator 0.1～5%, also contain antioxidant and water, the consumption of described antioxidant is 0.1～2% of acid and an amine total mass, and the consumption of described water is 1～30% of acid and an amine total mass.
The beneficial effect of low viscosity dimeric acid type polyamide hot melt adhesive of the present invention is: polyamide hot high temperature viscosity of the present invention is low, be easy to moulding, high and low temperature resistance and mechanical property preferably, water-intake rate is extremely low, environment-friendly solvent-free, can be widely used in automobile, electron trade, and with water is solvent, and material easily disperses, and the initial reaction stage temperature is low, the amine volatile quantity is little, environmentally safe.
On the basis of technique scheme, the present invention can also do following improvement.
Further, described dimeracid is all or part of hydrogenant dimeracid, and dimeric content is greater than 98% in the described dimeracid, and the tripolymer acid content is less than 2%, and monomer acids content is less than 0.5%.
Adopt the beneficial effect of above-mentioned further scheme to be, used dimeracid from unsaturated fatty acids in soybean oil, Oleum Gossypii semen, Oleum Verniciae fordii, the vegetable seed wet goods vegetables oil through being polymerized, so its raw material sources are abundant, relative low price, are renewable resources, environmental sound.Adopt hydrogenated dimer acids can improve the ageing-resistant performance of polyamide hot again.
Further, described aliphatic dibasic acid is C
2-18A kind of or any several mixture in the aliphatic dibasic acid.
Adopt the beneficial effect of above-mentioned further scheme to be, improve the softening temperature of polyamide hot by the consumption that increases diprotic acid.
Further, described aliphatic diamine is C
2-10The mixture of one or more in aliphatic diamine, the Piperazine anhydrous.
Adopt the beneficial effect of above-mentioned further scheme to be, adjust the mechanical property of polyamide hot by the consumption of adjusting diamine.
Further, described polyether polyamine is amino for containing 2～3 ends, and molecular weight is 100～3000 polyether polyamine, and polyether polyamine is a kind of or any several mixture among trade mark polyetheramine D-230, polyetheramine D-400, polyetheramine D-2000, the polyetheramine T-403.
Adopt the beneficial effect of above-mentioned further scheme to be, can adjust the resistance to low temperature of polyamide hot by the consumption of adjusting polyether polyamine.
Further, described molecular weight regulator is low-molecular-weight monofunctional acid or monofunctional amines.
Adopt the beneficial effect of above-mentioned further scheme to be, can adjust the viscosity of polyamide hot by the consumption of adjusting monofunctional acid or amine, the viscosity that makes institute's synthetic polyamide hot is easy to moulding within certain scope.
Further, described monofunctional acid is C
2-18A kind of several mixture arbitrarily in aliphatics monofunctional acid, Whitfield's ointment, lactic acid, phenylformic acid or the toluylic acid, described monofunctional amines is C
2-6A kind of several mixture arbitrarily in aliphatics monofunctional amines and the aniline.
Further; described oxidation inhibitor is for being Hypophosporous Acid, 50, phosphoric acid, four [β-(3; the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester; tricresyl phosphite (2; the 4-di-tert-butyl-phenyl) ester, N, N '-two-[3-(3, the 5-di-tert-butyl-hydroxy phenyl) propionyl] hexanediamine, 1; a kind of or any several mixture in two (3, the 5-di-t-butyl-4-hydroxyl-phenylpropionic acid) hydrazines of 2-
Adopt the beneficial effect of above-mentioned further scheme to be, the introducing of oxidation inhibitor has effectively stoped the oxidation in hot melt adhesive high temperature building-up process, and the ageing resistance in the raising use afterwards.
Another technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of preparation method of low viscosity dimeric acid type polyamide hot melt adhesive, it is characterized in that, and said method comprising the steps of:
1) by each raw material that takes by weighing of following molar percentage: dimeracid 55～95%, aliphatic dibasic acid 5～45%, aliphatic diamine 60～95%, polyether polyamine 5～40%, to be acid and the antioxidant of amine total mass 0.1～2% and consumption be 1～30% water of sour and amine total mass for molecular weight regulator 0.1～5%, consumption.
At first dimeracid, diprotic acid, polyether polyamine, oxidation inhibitor, molecular weight regulator and water are joined in the reaction vessel, stirring heating under nitrogen protection, in 30～120 minutes, be warming up to 50～150 ℃, under this temperature in 30～90 minutes, drip molar percentage and be 60～95% aliphatic dibasic acid and finish, constantly stirring reaction is 1～5 hour;
2) and then slowly heat up, temperature rises to 220～280 ℃ in 1～5 hour, and constantly steams the water that reaction generates; under this temperature, reacting 1～3 hour; and then in keeping 1～5 hour down, at last in the nitrogen protection bottom discharge, promptly less than 1000Pa pressure.
Adopt the beneficial effect of above-mentioned further scheme to be, it is low to have made high temperature viscosity, be easy to moulding, high and low temperature resistance and mechanical property preferably, the polyamide hot that water-intake rate is extremely low, and introduce an amount of water in initial reaction stage, make that the salify temperature at initial stage is lower, reaction mass disperses easily, and the volatile quantity of amine is little, and the water environmentally safe.
The preparation method's of low viscosity dimeric acid type polyamide hot melt adhesive of the present invention beneficial effect is: diamine adopts dripping method, and reaction process is comparatively stable, and amine equivalent is easy to control, good reproducibility.
The softening temperature of the polyamide hot that the present invention is prepared is 100～200 ℃.
High temperature (210 ℃) melt viscosity of institute of the present invention synthetic polyamide hot is 1000～10000mpa.s.
Embodiment
Below principle of the present invention and feature are described, institute gives an actual example and only is used to explain the present invention, is not to be used to limit scope of the present invention.
Embodiment 1
Having thermometer; agitator; add the 150.00g hydrogenated dimer acids in the 500mL four-hole boiling flask of condensing reflux and nitrogen tube; 25.50g sebacic acid; 18.12g polyetheramine D-230; 39.40g polyetheramine D-2000; 15.00g water; 1.8g four [β-(3; the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester; 1.20g propionic acid; and the 17.70g quadrol is encased in the constant pressure funnel; feed nitrogen stirring beginning heating; in 30 minutes, temperature is raised to 120 ℃; and begin slowly to drip quadrol in this temperature; dropwise in 40 minutes; this moment, temperature was raised to 130 ℃; and under this temperature salify 2 hours; and then slowly heat up; having water in this process steams; temperature is raised to 240 ℃ in 3 hours; under this temperature, kept 2 hours; then with vacuum pump vacuumize 2 hours to pressure be 100Pa, obtain light yellow adhesive tape in the nitrogen protection bottom discharge at last.
Embodiment 2
Have thermometer at one; agitator; add the 161.10g dimeracid in the 500mL four-hole boiling flask of prolong and nitrogen tube; 25.40g hexanodioic acid; 17.20g polyetheramine D-230; 28.00g polyetheramine D-2000; 12.00g water; 1.0g four [β-(3; the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester; 0.6g tricresyl phosphite (2; the 4-di-tert-butyl-phenyl) ester; 2.20g n-caproic acid; and the 22.70g quadrol is encased in the constant pressure funnel; feed nitrogen stirring beginning heating; in 60 minutes, temperature is raised to 120 ℃; and begin slowly to drip quadrol in this temperature; dropwise in 60 minutes; this moment, temperature was raised to 130 ℃; and under this temperature salify 2 hours; and then slowly heat up; having water in this process steams; temperature is raised to 280 ℃ in 3 hours, under this temperature, kept 5 hours, then with vacuum pump vacuumize 3 hours to pressure be 200Pa; in the nitrogen protection bottom discharge, obtain light yellow adhesive tape at last.
Embodiment 3
Have thermometer at one; agitator; add the 148.60g dimeracid in the 500mL four-hole boiling flask of prolong and nitrogen tube; 12.00g sebacic acid; 11.30g polyetheramine D-230; 65.63g polyetheramine D-2000; 12.00g water; 1.2g four [β-(3; the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester; 0.3g Hypophosporous Acid, 50; 4.2g stearic acid; and the 18.24g propylene diamine is encased in the constant pressure funnel; feed nitrogen stirring beginning heating; in 50 minutes, temperature is raised to 110 ℃; and begin slowly to drip propylene diamine in this temperature; dropwise in 70 minutes; this moment, temperature was raised to 130 ℃; and under this temperature salify 2 hours; and then slowly heat up; having water in this process steams; temperature is raised to 220 ℃ in 2 hours; under this temperature, kept 1 hour; then with vacuum pump vacuumize 3 hours to pressure be 400Pa, at last in the nitrogen protection bottom discharge, obtain light yellow adhesive tape.
Embodiment 4
Have thermometer at one; agitator; add the 150.50g dimeracid in the 500mL four-hole boiling flask of prolong and nitrogen tube; 15.20g sebacic acid; 30.56g polyetheramine D-400; 55.57g polyetheramine D-2000; 11.00g water; 0.7g N; N '-two-[3-(3; the 5-di-tert-butyl-hydroxy phenyl) propionyl] hexanediamine; 0.5g 1; 2-two (3; 5-di-t-butyl-4-hydroxyl-phenylpropionic acid) hydrazine; 0.6g four [β-(3; the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester; 1.93g positive enanthic acid; and the 18.01g propylene diamine is encased in the constant pressure funnel; feed nitrogen stirring beginning heating; when being raised to 110 ℃, temperature begins slowly to drip propylene diamine; dropwise in 40 minutes; this moment, temperature was raised to 130 ℃; and under this temperature salify 2 hours; and then slowly heat up; having water in this process steams; temperature is raised to 250 ℃ in 3 hours; under this temperature, kept 4 hours; then with vacuum pump vacuumize 3 hours to pressure be 600Pa; in the nitrogen protection bottom discharge, obtain light yellow adhesive tape at last.
Embodiment 5
Have thermometer at one; agitator; add the 300.50g dimeracid in the four-hole boiling flask of the 1000mL of prolong and nitrogen tube; 55.93g nonane diacid; 12.22g Piperazine anhydrous; 133.48g polyetheramine D-2000; 2.5g four [β-(3; the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester; 1.0g tricresyl phosphite (2; the 4-di-tert-butyl-phenyl) ester; 0.3g phosphoric acid; 20.00g water; 1.3g propionic acid; and the 37.60g quadrol is encased in the constant pressure funnel; feed nitrogen stirring beginning heating; when being raised to 110 ℃, temperature begins slowly to drip quadrol; dropwise in 40 minutes; this moment, temperature was raised to 130 ℃; and under this temperature salify 2 hours; and then slowly heat up; having water in this process steams; temperature is raised to 260 ℃ in 2 hours; under this temperature, kept 2 hours; then with vacuum pump vacuumize 3 hours to pressure be 800Pa, at last in the nitrogen protection bottom discharge, obtain light yellow adhesive tape.
Concrete verification experimental verification
Performance by following verification experimental verification the above embodiment of the present invention 1～5 described hot melt adhesive sample and common dimeric acid type polyamide hot melt adhesive.
Test experiments 1: softening temperature is measured according to GB/T 15332-94
Test experiments 2: melt viscosity is measured according to HG/T 3660-1999
Test experiments 3: resistance to low temperature is measured according to ASTM-D3111.
Test result is as shown in table 1 below.
The sample of table 1 embodiment 1-5 and common dimeric acid type polyamide hot melt adhesive performance comparison test result
As can be seen from Table 1, institute of the present invention synthetic dimeric acid type polyamide hot melt adhesive has higher softening temperature, more shallow color, the lower happy and harmonious viscosity of high temperature and resistance to low temperature preferably, so institute of the present invention synthetic polyamide hot has high and low temperature resistance preferably, lower high temperature viscosity, moulding process is simple, is specially adapted to automobile and electron trade.
The above only is preferred embodiment of the present invention, and is in order to restriction the present invention, within the spirit and principles in the present invention not all, any modification of being done, is equal to replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (10)
1. low viscosity dimeric acid type polyamide hot melt adhesive, it is characterized in that, described hot melt adhesive is made up of each raw material of following molar percentage: dimeracid 55～95%, aliphatic dibasic acid 5～45%, aliphatic diamine 60～95%, polyether polyamine 5～40%, molecular weight regulator 0.1～5%, also contain antioxidant and water, the consumption of described antioxidant is 0.1～2% of acid and an amine total mass, and the consumption of described water is 1～30% of acid and an amine total mass.
2. low viscosity dimeric acid type polyamide hot melt adhesive according to claim 1 is characterized in that, described dimeracid is all or part of hydrogenant dimeracid, and dimeric content is more than 98% in the described dimeracid.
3. low viscosity dimeric acid type polyamide hot melt adhesive according to claim 1 is characterized in that, described aliphatic dibasic acid is C
2-18A kind of or any several mixture in the aliphatic dibasic acid.
4. low viscosity dimeric acid type polyamide hot melt adhesive according to claim 1 is characterized in that, described aliphatic diamine is C
2-10A kind of or any several mixture in aliphatic diamine, the Piperazine anhydrous.
5. low viscosity dimeric acid type polyamide hot melt adhesive according to claim 1 is characterized in that, described polyether polyamine is amino for containing 2～3 ends, and molecular weight is 100～3000 polyether polyamine.
6. low viscosity dimeric acid type polyamide hot melt adhesive according to claim 5 is characterized in that, described polyether polyamine is a kind of or any several mixture among trade mark polyetheramine D-230, polyetheramine D-400, polyetheramine D-2000 or the polyetheramine T-403.
7. low viscosity dimeric acid type polyamide hot melt adhesive according to claim 1 is characterized in that, described molecular weight regulator is low-molecular-weight monofunctional acid or monofunctional amines.
8. low viscosity dimeric acid type polyamide hot melt adhesive according to claim 7 is characterized in that, described monofunctional acid is C
2-18A kind of several mixture arbitrarily in aliphatics monofunctional acid, Whitfield's ointment, lactic acid, phenylformic acid or the toluylic acid, described monofunctional amines is C
2-18A kind of several mixture arbitrarily in aliphatics monofunctional amines or the aniline.
9. low viscosity dimeric acid type polyamide hot melt adhesive according to claim 1; it is characterized in that; described oxidation inhibitor is Hypophosporous Acid, 50, phosphoric acid, four [β-(3; the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, tricresyl phosphite (2, the 4-di-tert-butyl-phenyl) ester, N; N '-two-[3-(3; the 5-di-tert-butyl-hydroxy phenyl) propionyl] hexanediamine, 1, a kind of or any several mixture in two (3, the 5-di-t-butyl-4-hydroxyl-phenylpropionic acid) hydrazines of 2-.
10. the preparation method of a low viscosity dimeric acid type polyamide hot melt adhesive is characterized in that, said method comprising the steps of:
1) by each raw material that takes by weighing of following molar percentage: dimeracid 55～95%, aliphatic dibasic acid 5～45%, polyether polyamine 5～40%, molecular weight regulator 0.1～5%, suitable quantity of water, oxidation inhibitor joins it in reaction vessel, stirring heating under nitrogen protection, in 30～120 minutes, be warming up to 50～150 ℃, under this temperature in 30～90 minutes, drip molar percentage and be 60～95% aliphatic diamine and finish, and constantly stirred into salt 1～5 hour;
2) and then slowly heat up, temperature rises to 220～280 ℃ in 1～5 hour, and constantly steams the water that reaction generates; under this temperature, reacting 1～3 hour; and then under less than the pressure of 1000Pa, kept 1～5 hour, at last in the nitrogen protection bottom discharge, promptly.
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| CN102220105A (en) * | 2011-04-29 | 2011-10-19 | 烟台德邦电子材料有限公司 | Dimer acid type polyamide hot melt adhesive and preparation method thereof |
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| CN102492135A (en) * | 2011-11-30 | 2012-06-13 | 上海天洋热熔胶有限公司 | Method for synthesizing dimer acid type polyamide hot melt adhesive |
| 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 |
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| CN103834346A (en) * | 2012-11-22 | 2014-06-04 | 上海理日化工新材料有限公司 | Dimer acid type polyamide hot-melt adhesive composition |
| CN104356998A (en) * | 2014-09-23 | 2015-02-18 | 苏州雷立特新材料科技有限公司 | Polyamide hot melt adhesive used in electronic packaging field |
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| CN102443374A (en) * | 2011-11-01 | 2012-05-09 | 烟台德邦电子材料有限公司 | Copolyamide hot melt adhesive and its preparation method |
| CN102492135A (en) * | 2011-11-30 | 2012-06-13 | 上海天洋热熔胶有限公司 | Method for synthesizing dimer acid type polyamide hot melt adhesive |
| 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 |
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| CN115746780B (en) * | 2022-11-24 | 2023-08-01 | 山东凯恩新材料科技有限公司 | Polyamide hot melt adhesive and preparation method and application thereof |
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