CN113583617B - Self-repairing reaction type polyurethane hot melt adhesive and preparation method thereof - Google Patents
Self-repairing reaction type polyurethane hot melt adhesive and preparation method thereof Download PDFInfo
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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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
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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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/06—Polyurethanes from polyesters
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
A self-repairing reaction type polyurethane hot melt adhesive and a preparation method thereof. The invention belongs to the field of polyurethane hot melt adhesives. The invention aims to solve the technical problems that the existing material for realizing self-repair by introducing a disulfide bond can not realize quick repair and the mechanical property is reduced along with the increase of the repair times. The self-repairing reaction type polyurethane hot melt adhesive is prepared from polymer polyol, polyisocyanate, a disulfide chain extender, a catalyst, tackifying resin, a viscosity regulator, a polymerization inhibitor and a filler. The method comprises the following steps: step 1, mixing materials; step 2, generating a prepolymer; step 3, chain extension reaction; and 4, finishing the reaction and discharging. The method is simple, raw materials are easy to obtain, processes of glue picking and repairing, glue repairing and the like are omitted, the cost is greatly saved, the self-repairing function can be still realized in a heating mode after the curing is realized under the condition of moisture, the self-repairing speed is high, and the mechanical property can still maintain a high value along with the increase of the repairing times.
Description
Technical Field
The invention belongs to the field of polyurethane hot melt adhesives, and particularly relates to a self-repairing reactive polyurethane hot melt adhesive and a preparation method thereof.
Background
The polyurethane hot melt is an environment-friendly solvent-free green adhesive, and is widely applied to the fields of electronic device assembly, automobile part bonding, wood processing and the like. The existing polyurethane hot melt adhesives are mainly divided into thermoplastic polyurethane hot melt adhesives (TPU) and reactive polyurethane hot melt adhesives (PUR). The thermoplastic polyurethane hot melt adhesive has a linear chemical structure and shows poor bonding strength and solvent resistance; the reactive polyurethane hot melt adhesive is a polyurethane prepolymer terminated by isocyanate, can further react with moisture in the atmosphere to finally form a crosslinked chemical structure, has excellent bonding strength and solvent resistance, but has slow curing speed, often needs a period of several days to be completely cured, is difficult to disassemble once the crosslinked structure is formed, cannot be recycled, and has relatively short storage life due to the existence of reactive isocyanate groups. These drawbacks limit the use of polyurethane hot melt adhesives. The introduction of disulfide bonds constructs the dynamically connected polyurethane hot melt adhesive, and integrates the advantages of the existing polyurethane hot melt adhesive.
The self-repairing polyurethane hot melt adhesive can repair cracks and damages and improve the reliability and durability of the material. The repair mechanism can be divided into two categories of intrinsic self-repair and external self-repair. Intrinsic self-repairing is realized by means of dynamic non-covalent bonds, reversible covalent bonds, electrostatic action and the like. Compared with the external type which needs to repair damage by external repair agents wrapped by microcapsules, hollow fibers and the like, the intrinsic type can realize multiple repairs only by simple conditions such as illumination, external force, temperature, pH change and the like, even without external stimulation.
The bonding energy of the dynamic covalent bond is relatively high, and the dynamic covalent bond generally has excellent mechanical properties, so that the service life and the use safety of the material can be effectively improved. The disulfide bond can realize dynamic reversibility, and has mild repair condition and simple and convenient use. The disulfide bond is introduced into the adhesive, so that the processes of repairing, glue repairing and the like can be omitted in use, the cost is greatly saved, and the operation period is shortened. Therefore, a disulfide bond is introduced, a polyurethane hot melt adhesive which gives consideration to mild repair conditions and excellent performance is provided, and a preparation method of the material has significant scientific and industrial values for the application of the self-repairing reaction type polyurethane. However, in the current materials for realizing self-repair by introducing disulfide bonds, the problems of not achieving quick repair and not achieving the problem of keeping the mechanical property unchanged along with the increase of repair times are solved.
Disclosure of Invention
The invention aims to solve the technical problems that the existing material for realizing self-repairing by introducing a disulfide bond cannot realize quick repairing and the mechanical property is reduced along with the increase of repairing times, and provides a self-repairing reaction type polyurethane hot melt adhesive and a preparation method thereof.
The self-repairing reaction type polyurethane hot melt adhesive is prepared from the following components in parts by weight:
20 to 55 portions of polymer polyol,
10-20 parts of polyisocyanate,
1-5 parts of a disulfide chain extender,
0.01 to 0.05 portion of catalyst,
5 to 15 parts of tackifying resin,
6 to 10 portions of viscosity regulator,
0.01 to 0.05 portion of polymerization inhibitor,
0.1 to 3 portions of filling material,
the molar ratio of-NCO/-OH in the self-repairing reactive polyurethane hot melt adhesive is more than 1.
Further defined, the polymer polyol is one of a polyester polyol or a polyether polyol.
Further, the polyisocyanate is 4,4' -methylene diphenyl diisocyanate, toluene diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate or a mixture of several of liquefied MDI according to any ratio.
Further limiting, the disulfide chain extender is one or a mixture of a plurality of bis (2-hydroxyethyl) disulfide, 3,3-dihydroxy diphenyl disulfide, cystine, 4,4-dithiodiphenylamine and bis (11-hydroxyundecyl) disulfide according to any ratio.
Further limiting, the catalyst is one or a mixture of two of dibutyltin dilaurate, stannous octoate, triethylamine and dimorpholinyl diethyl ether in any ratio.
The tackifying resin is further limited to be one or a mixture of several of rosin and derivatives thereof, terpene resin, acrylic resin and synthetic series resin according to any ratio.
Further limit, the viscosity regulator is one or a mixture of several of paraffin wax, microcrystalline wax and synthetic wax according to any ratio.
Further limited, the polymerization inhibitor is p-benzoquinone or hydroquinone.
Further defined, the filler is carbon black, gas phase SiO 2 One or more of talcum powder, white carbon black, barite powder, mica powder, calcium carbonate, calcium oxide, asbestos powder, titanium dioxide, aluminum powder, iron powder, corundum powder and carborundum in any ratioA compound (I) is provided.
The preparation method of the self-repairing reaction type polyurethane hot melt adhesive disclosed by the invention comprises the following steps of:
step 1, mixing materials: mixing and stirring polymer polyol and tackifying resin at the temperature of 110-120 ℃ and the rpm of 100, mixing to be homogeneous, and then carrying out vacuum dehydration treatment;
step 2, generating a prepolymer: adding the mixture treated in the step one into a vacuum reaction kettle, dropwise adding polyisocyanate into the system at the temperature of 60-75 ℃, stirring for 1-2 h in vacuum, heating to 80-90 ℃, adding a catalyst, and carrying out vacuum reaction for 0.5-1 h;
step 3, chain extension reaction: slowly adding a disulfide chain extender into the system, and reacting for 1-2 h at the temperature of 80-90 ℃;
and 4, finishing the reaction and discharging: and (3) reducing the temperature of the system to 60-70 ℃, then adding the filler, the viscosity regulator and the polymerization inhibitor, reacting for 20-40 min under vacuum, stopping heating, filling nitrogen and discharging to obtain the self-repairing reactive polyurethane hot melt adhesive.
Further limiting, the speed of slowly adding the disulfide chain extender in the step 3 is 0.04 g/min-0.06 g/min.
Further defined, the discharge temperature in step 4 is < 50 ℃.
Compared with the prior art, the invention has the advantages that:
1) The invention provides a self-repairing reaction type polyurethane hot melt adhesive and a preparation method thereof, the preparation method is simple, raw materials are easy to obtain, the processes of adhesive picking, repairing, adhesive repairing and the like are omitted, and the cost is greatly saved.
2) After the thermosetting polyurethane hot melt adhesive prepared by the invention is cured under the condition of moisture, the thermosetting polyurethane hot melt adhesive can still carry out the self-repairing function in a heating mode, the self-repairing speed is high, and the mechanical property can still maintain a high value along with the increase of the repairing times.
3) Disulfide bonds (-S-S-) exist in the chain extender, are introduced into the main body structure and can be uniformly dispersed in the colloid, wherein the disulfide bonds in the long chain can improve the flexibility of the long chain, so that the overall flexibility of the material can be improved.
Detailed Description
Example 1: the self-repairing reaction type polyurethane hot melt adhesive is prepared from the following components in parts by weight: 43.5g of polymer polyol PTMG-2000, 14.15g of isophorone diisocyanate, 4.2g of bis (2-hydroxyethyl) disulfide, 0.01g of dibutyltin dilaurate, 8g of terpene resin, 6g of paraffin wax, 0.01g of p-benzoquinone, 1g of carbon black;
the preparation method of the self-repairing reactive polyurethane hot melt adhesive of preparation example 1 was carried out according to the following steps:
step 1, mixing materials: mixing 43.5g of polymer polyol PTMG-2000 and 8g of terpene resin at 110 ℃ and 100rpm, stirring, mixing to obtain a homogeneous phase, and performing vacuum dehydration treatment;
step 2, generating a prepolymer: adding the mixture treated in the step one into a vacuum reaction kettle, dropwise adding 14.15g of isophorone diisocyanate into the system at 70 ℃, stirring for 1.5h in vacuum, then heating to 80 ℃, adding 0.01g of dibutyltin dilaurate, and carrying out vacuum reaction for 0.5h;
step 3, chain extension reaction: adding 4.2g of bis (2-hydroxyethyl) disulfide into the system at the speed of 0.05g/min, and reacting for 2 hours at the temperature of 80 ℃;
and 4, finishing the reaction and discharging: and (3) cooling the system to 60 ℃, adding 1g of carbon black, 6g of paraffin and 0.01g of p-benzoquinone, reacting for 30min under vacuum until the reactant is thickened, stopping heating, filling nitrogen for discharging, and discharging at the discharging temperature of 30 ℃ to obtain the self-repairing reactive polyurethane hot melt adhesive.
Example 2: the self-repairing reaction type polyurethane hot melt adhesive is prepared from the following components in parts by weight: 43.5g of polymer polyol PTMG-2000, 14.15g of isophorone diisocyanate, 3g of 3,3-dihydroxydiphenyl disulfide, 0.01g of dibutyltin dilaurate, 8g of terpene resin, 6g of paraffin wax, 0.01g of p-benzoquinone, 1g of carbon black;
the preparation method of the self-repairing reaction type polyurethane hot melt adhesive of the preparation example 2 comprises the following steps:
step 1, mixing materials: mixing 43.5g of polymer polyol PTMG-2000 and 8g of terpene resin at 110 ℃ and 100rpm, stirring, mixing to obtain a homogeneous phase, and performing vacuum dehydration treatment;
step 2, generating a prepolymer: adding the mixture treated in the step one into a vacuum reaction kettle, dropwise adding 14.15g of isophorone diisocyanate into the system at 70 ℃, stirring for 1.5h in vacuum, then heating to 80 ℃, adding 0.01g of dibutyltin dilaurate, and carrying out vacuum reaction for 0.5h;
step 3, chain extension reaction: 3g of 3,3-dihydroxy diphenyl disulfide are added into the system at the speed of 0.05g/min and reacted for 2h at 80 ℃;
and 4, finishing the reaction and discharging: and (3) cooling the system to 60 ℃, adding 1g of carbon black, 6g of paraffin and 0.01g of p-benzoquinone, reacting for 30min under vacuum until the reactant is thickened, stopping heating, filling nitrogen for discharging, and discharging at the discharging temperature of 30 ℃ to obtain the self-repairing reactive polyurethane hot melt adhesive.
Comparative example 1: the reactive polyurethane hot melt adhesive is prepared from the following components in parts by mass: 43.5g of polymer polyol PTMG-2000, 14.15g of isophorone diisocyanate, 3g of 1,4-butanediol, 0.01g of dibutyltin dilaurate, 8g of terpene resin, 6g of paraffin wax, 0.01g of p-benzoquinone, 1g of carbon black;
the preparation method of the reactive polyurethane hot melt adhesive of comparative example 1 was carried out according to the following steps:
step 1, mixing materials: mixing 43.5g of polymer polyol PTMG-2000 and 8g of terpene resin at 110 ℃ and 100rpm, stirring, mixing to obtain a homogeneous phase, and performing vacuum dehydration treatment;
step 2, generating a prepolymer: adding the mixture treated in the step one into a vacuum reaction kettle, dropwise adding 14.15g of isophorone diisocyanate into the system at 70 ℃, stirring for 1.5h in vacuum, then heating to 80 ℃, adding 0.01g of dibutyltin dilaurate, and carrying out vacuum reaction for 0.5h;
step 3, chain extension reaction: 3g of 1,4-butanediol is added into the system at the speed of 0.05g/min and reacted for 2h at the temperature of 80 ℃;
and 4, finishing the reaction and discharging: and (3) cooling the system to 60 ℃, adding 1g of carbon black, 6g of paraffin and 0.01g of p-benzoquinone, reacting for 30min under vacuum until the reactant is thickened, stopping heating, filling nitrogen, and discharging to obtain the reactive polyurethane hot melt adhesive.
Test one, characterization of self-healing performance: the time at which the scratch disappeared was measured by brushing the scratch with a steel wire on the surface of the polyurethane hot melt adhesive after curing (25 ℃,60% rh for 48 hours).
The results of the self-repairing performance tests on the polyurethane hot melt adhesives prepared in examples 1, 2 and 1 are shown in Table 1:
table 1 self-repair performance test results
| Test specimen | Normal temperature self-repairing time/s | Self-repairing time/s at 40 ℃ by heating |
| Example 1 | 16 | 11 |
| Example 2 | 15 | 10 |
| Comparative example 1 | Is not repaired | Is not repaired |
Test two, mechanical property characterization: tensile shear test was performed according to ASTM D1002 standards using aluminum sheet as the substrate, and the mechanical property test results are shown in table 2.
TABLE 2 mechanical Property test results
| Test specimen | Tensile strength | Elongation at break | Hardness of | Tensile shear force |
| Example 1 | 25MPa | 480％ | 80 | 2606N |
| Example 2 | 24MPa | 510％ | 80 | 2530N |
| Comparative example 1 | 20MPa | 215％ | 72 | 1001N |
And thirdly, characterizing the mechanical property after repeated repair: the polyurethane hot melt adhesive samples of example 1 after curing (48 h curing at 25 ℃,60% RH) were cut and then repaired at 40 ℃ and tested for mechanical properties after repair, the results of which are shown in Table 3.
TABLE 3 test results after repeated repairs
| Test specimen | Tensile strength | Elongation at break | Hardness of | Tensile shear force |
| Is not repaired | 25MPa | 480％ | 80 | 2606N |
| Self-repairing for 1 time | 25MPa | 477％ | 82 | 2600N |
| Self-repairing for 2 times | 24MPa | 484％ | 78 | 2570N |
| Self-repairing for 3 times | 25MPa | 481％ | 79 | 2610N |
Claims (7)
1. The self-repairing reaction type polyurethane hot melt adhesive is characterized by being prepared from the following components in parts by mass:
20-55 parts of polymer polyol, wherein the polymer polyol is one of polyester polyol or polyether polyol;
10-20 parts of polyisocyanate, wherein the polyisocyanate is one or a mixture of 4,4' -methylene diisocyanate phenyl ester, toluene diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate and liquefied MDI;
1-5 parts of a disulfide chain extender, wherein the disulfide chain extender is bis (2-hydroxyethyl) disulfide or 3,3-dihydroxy diphenyl disulfide;
0.01 to 0.05 portion of catalyst,
5-15 parts of tackifying resin,
6 to 10 portions of viscosity regulator,
0.01 to 0.05 portion of polymerization inhibitor,
0.1 to 3 portions of filler,
the molar ratio of-NCO/-OH in the self-repairing reaction type polyurethane hot melt adhesive is more than 1.
2. The self-repairing reactive polyurethane hot melt adhesive according to claim 1, wherein the catalyst is one or a mixture of two of dibutyltin dilaurate, stannous octoate, triethylamine and dimorpholinyl diethyl ether, and the tackifying resin is one or a mixture of several of rosin and derivatives thereof, terpene resin, acrylic resin and synthetic series resin.
3. The self-repairing reactive polyurethane hot melt adhesive of claim 1, wherein the viscosity modifier is one or a mixture of paraffin, microcrystalline wax and synthetic wax, and the polymerization inhibitor is p-benzoquinone or hydroquinone.
4. The self-repairing reactive polyurethane hot melt adhesive of claim 1, wherein the filler is carbon black or gas phase SiO 2 One or a mixture of more of talcum powder, white carbon black, barite powder, mica powder, calcium carbonate, calcium oxide, asbestos powder, titanium dioxide, aluminum powder, iron powder, corundum powder and carborundum.
5. The preparation method of the self-repairing reactive polyurethane hot melt adhesive as claimed in any one of claims 1 to 4, which is characterized by comprising the following steps:
step 1, mixing materials: mixing and stirring polymer polyol and tackifying resin at the temperature of 110-120 ℃ and the rpm of 100, mixing to be homogeneous, and then carrying out vacuum dehydration treatment;
step 2, prepolymer generation: adding the mixture treated in the step one into a vacuum reaction kettle, dropwise adding polyisocyanate into the system at the temperature of 60-75 ℃, stirring for 1-2 h in vacuum, heating to 80-90 ℃, adding a catalyst, and reacting for 0.5-1 h in vacuum;
step 3, chain extension reaction: slowly adding a disulfide chain extender into the system, and reacting for 1-2 h at the temperature of 80-90 ℃;
and 4, finishing the reaction and discharging: and (3) reducing the temperature of the system to 60-70 ℃, then adding the filler, the viscosity regulator and the polymerization inhibitor, reacting for 20-40 min under vacuum, stopping heating, filling nitrogen and discharging to obtain the self-repairing reactive polyurethane hot melt adhesive.
6. The preparation method of the self-repairing reactive polyurethane hot melt adhesive according to claim 5, wherein the speed of slowly adding the disulfide chain extender in the step 3 is 0.04g/min to 0.06g/min.
7. The preparation method of the self-repairing reactive polyurethane hot melt adhesive according to claim 5, wherein the discharging temperature in the step 4 is less than 50 ℃.
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| CN114044868B (en) * | 2021-11-26 | 2023-10-13 | 韦尔通科技股份有限公司 | Heating detachable polyurethane hot melt adhesive, preparation raw materials, preparation method and bonding method thereof |
| CN115157807A (en) * | 2021-12-31 | 2022-10-11 | 无锡上美纸制品有限公司 | Self-adhesive film for stainless steel and preparation method thereof |
| CN114849522A (en) * | 2022-04-14 | 2022-08-05 | 湖南优冠体育材料有限公司 | Preparation method and device of environment-friendly high-adhesion artificial lawn glue |
| CN115785834B (en) * | 2022-11-28 | 2024-06-14 | 广东中鼎科技发展有限公司 | TPU high-low temperature film with repairing function and preparation method thereof |
| CN117701221B (en) * | 2023-12-25 | 2024-07-19 | 深圳市道丰宁科技有限公司 | Hot melt adhesive and preparation method thereof |
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