CN114958272A - Moisture-curing polyurethane hot melt adhesive for aluminum-plastic compounding - Google Patents

Moisture-curing polyurethane hot melt adhesive for aluminum-plastic compounding Download PDF

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Publication number
CN114958272A
CN114958272A CN202210695937.XA CN202210695937A CN114958272A CN 114958272 A CN114958272 A CN 114958272A CN 202210695937 A CN202210695937 A CN 202210695937A CN 114958272 A CN114958272 A CN 114958272A
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China
Prior art keywords
aluminum
hot melt
melt adhesive
moisture
polyurethane hot
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CN202210695937.XA
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Inventor
李禹函
刘文凯
孟旭
武金笔
吴林志
顾刘峰
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Zhengzhou Huapu Sealing Material Co ltd
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Zhengzhou Huapu Sealing Material Co ltd
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/42Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44Polycarbonates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67Unsaturated compounds having active hydrogen
    • C08G18/69Polymers of conjugated dienes
    • C08G18/698Mixtures with compounds of group C08G18/40
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/74Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/757Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02Non-macromolecular additives
    • C09J11/06Non-macromolecular additives organic

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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)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The invention discloses a moisture-curing polyurethane hot melt adhesive for aluminum-plastic compounding, which is prepared from the following raw materials in parts by weight: 20-25 parts of polycarbonate diol, 10-25 parts of dicyclopentadiene, 10-20 parts of hydroxyl-terminated polybutadiene, 4-10 parts of alicyclic diisocyanate, 15-45 parts of filler and 0.1-0.5 part of catalyst. The polycarbonate type and polybutadiene type polyols can regulate and control the body strength and toughness of the cured adhesive layer, are favorable for bonding with PET, polyvinyl chloride and polypropylene substrates, and the polybutadiene soft segment and dicyclopentadiene can effectively improve the bonding effect with low-surface-energy substrates. The adopted dimer acid diisocyanate DDI contains two long aliphatic chains, can promote the compatibility of polybutadiene soft segments in the synthesis stage, can permeate into the surface of a low-surface-energy base material to form an interface layer in the melt sizing stage, realizes the improvement of the bonding performance of the base material, can be used for bonding between aluminum materials and plastics, and can also be used for bonding between metals.

Description

Moisture-cured polyurethane hot melt adhesive for aluminum-plastic compounding
Technical Field
The invention relates to a moisture-curing polyurethane hot melt adhesive for aluminum-plastic compounding, belonging to the technical field of polyurethane adhesives.
Background
The traditional moisture curing polyurethane hot melt adhesive (PUR for short) is a polyurethane adhesive containing terminal isocyanic acid radical (-NCO) and is also a reaction type hot melt adhesive. When in use, the glue is applied after being heated and melted, after the glue layer is cooled and physically solidified to generate primary bonding force, the isocyanic acid radical in the glue layer reacts with moisture in the air or an active hydrogen compound on the surface of an adherend to generate chemical crosslinking solidification. Compared with other types of hot melt adhesives, the hot melt adhesive has the advantages of convenience in use, high elasticity, solvent resistance, wear resistance and the like. Therefore, the moisture-curing polyurethane hot melt adhesive is widely applied to the automobile industry, the shoe industry, the textile industry, the wood industry, the electronic industry, the book binding industry and the like. The moisture-curing polyurethane hot melt adhesive is developed in the beginning of the 20 th century and the 80 th century in the United states at first, and the research and development of polyurethane adhesives in China are relatively late, so that the high-end brand of the polyurethane adhesives is still monopolized abroad at present.
At present, the existing moisture-curing polyurethane hot melt adhesive has the problem that the surface of a plastic substrate is easy to debond in the aspect of aluminum-plastic composite bonding, and the problem is caused by relatively low surface energy of PVC (polyvinyl chloride), polyesters and particularly polyolefin resin. In addition, the hot melt adhesive still has the problems of high melt viscosity, short opening time, high cost and the like, needs to be further improved, and the variety of the adhesive is relatively less, so that the variety of products needs to be enriched.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide the moisture curing polyurethane hot melt adhesive for aluminum-plastic compounding.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows: a moisture curing polyurethane hot melt adhesive for aluminum-plastic compounding is prepared from the following raw materials in parts by weight:
20-25 parts of polycarbonate diol;
10-25 parts of dicyclopentadiene;
10-20 parts of hydroxyl-terminated polybutadiene;
4-10 parts of alicyclic diisocyanate;
15-45 parts of a filler;
0.1-0.5 part of catalyst.
The number average molecular weight of the polycarbonate diol is 2000-4000g/mol, the number average molecular weight of the hydroxyl-terminated polybutadiene is 3000-5000g/mol, the alicyclic diisocyanate is dimer acid diisocyanate DDI, and the chemical structural formula is
Figure BDA0003702212580000011
The filler is one or a mixture of heavy calcium carbonate, nano calcium carbonate and light calcium carbonate.
The catalyst is dibutyltin dilaurate.
The mass fraction of isocyanic acid radical (NCO) in the moisture curing polyurethane hot melt adhesive for aluminum-plastic compounding is 3-6%.
The invention also provides a preparation method of the moisture curing polyurethane hot melt adhesive for aluminum-plastic compounding, which comprises the following steps: putting polycarbonate diol and hydroxyl-terminated polybutadiene into a reaction kettle, mixing, heating to 110 ℃ under the vacuum degree of-0.1 MPa, removing water for 1 hour, cooling to 80 ℃, adding a set amount of alicyclic diisocyanate, adding a catalyst dibutyltin dilaurate, stirring for 1 hour, sequentially adding dicyclopentadiene and a filler, monitoring the NCO content by a potentiometric titration method, stopping the reaction after the NCO content reaches a preset requirement, taking out of the kettle, and packaging to obtain the hot melt adhesive.
The melt viscosity of the moisture-curing polyurethane hot melt adhesive for aluminum-plastic composite at 140 ℃ is 6700-9550mPa & s, which is measured according to Brookfield-ASTM D3236.
The opening time of the moisture curing polyurethane hot melt adhesive for aluminum-plastic composite is less than 5 minutes, and is determined according to HG/T3716-2003.
The initial bonding strength and the shear strength of the moisture-cured polyurethane hot melt adhesive for aluminum-plastic compounding to polypropylene, PET and polyvinyl chloride are respectively greater than 0.55MPa and 3.50MPa, and the initial bonding strength and the shear strength to aluminum alloy are respectively greater than 1.50MPa and 7.0MPa, and the moisture-cured polyurethane hot melt adhesive for aluminum-plastic compounding can be used for bonding between aluminum materials and plastics and bonding between metal and metal according to GB/T7214-2008.
Compared with the prior art, the invention has the beneficial effects that: (1) the polycarbonate type and polybutadiene type polyols are compounded, so that the strength and toughness of the cured adhesive layer can be regulated and controlled, the two can be favorably bonded with PET, polyvinyl chloride and polypropylene substrates, and the bonding effect of the polybutadiene soft segment and dicyclopentadiene with the low-surface-energy substrate can be effectively improved; (2) the adopted dimer acid diisocyanate DDI contains two long fatty chains, can promote the compatibility of polybutadiene soft segments in the synthesis stage, and can permeate into the surface of a low-surface-energy base material to form an interface layer in the melt sizing stage, so that the bonding performance of the three base materials is improved.
Detailed description of the preferred embodiment
To better illustrate the objects, aspects and advantages of the present invention, the present invention will be further described with reference to specific examples.
The following raw materials are used in the experiments of the examples and comparative examples of the present invention, but the present invention is not limited to the following raw materials, and the following raw materials are used as specific examples to further specifically illustrate the effects of the moisture-curable polyurethane hot melt adhesive for aluminum-plastic lamination in the present invention.
Polycarbonate diol: PCDL, designation UH-CARB200, nan tong run-rich petrochemical.
Dicyclopentadiene DCPD, kowadd chemical.
Hydroxyl-terminated polybutadiene: the number average molecular weight of the type I HTPB in the astronomical chemical industry is 4000 g/mol.
Alicyclic diisocyanate: DDI, molecular weight 600g/mol, Riming chemical research design institute.
Aromatic diisocyanate: MDI-100, Tantai Wanhua.
Filling: heavy calcium carbonate and nano calcium carbonate in a weight ratio of 4: 1.
Catalyst: dibutyl tin dilaurate, DBTDL.
Table 1: examples 1-6 and comparative examples 1-3 formulations
Figure BDA0003702212580000031
Examples 1-6 and comparative examples 1-3 were prepared as follows: according to a set proportion, putting PCDL and I type HTPB into a reaction kettle, heating to 110 ℃ under the vacuum degree of-0.1 MPa to remove water for 1 hour, cooling to 80 ℃, adding DDI or MDI-100 with a set amount, adding a catalyst DBTDL, stirring for 1 hour, putting heavy calcium carbonate, nano calcium carbonate and DCPD with the mass ratio of 4:1, and stopping the reaction until the NCO content in the system reaches a preset requirement.
The finished products prepared in the examples and the comparative examples of the invention are applied with glue at 130 ℃ to prepare samples, and the test method of each performance index is specifically shown in Table 2.
Table 2: test method
Test items Unit of Reference standard
Viscosity of the oil mPa·s Brookfield-ASTMD3236(140℃)
Open time Minute (min) HG/T3716-2003
Initial bondingStrength of MPa GB/T7124-2008
Shear strength MPa GB/T7124-2008
Table 3: results of evaluating the Properties of samples of examples 1 to 6 and comparative examples 1 to 3
Figure BDA0003702212580000032
Figure BDA0003702212580000041
The polyurethane hot melt adhesives of the embodiments 1-6 of the invention have low viscosity, high initial bonding strength and shear strength to four base materials, short opening time, and suitability for rapid assembly on an assembly line, and the hot melt adhesives of the comparative examples 1-3 have high viscosity and inferior bonding performance to the embodiments.
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.

Claims (9)

1. The moisture-curing polyurethane hot melt adhesive for aluminum-plastic compounding is characterized by being prepared from the following raw materials in parts by weight: 20-25 parts of polycarbonate diol, 10-25 parts of dicyclopentadiene, 10-20 parts of hydroxyl-terminated polybutadiene, 4-10 parts of alicyclic diisocyanate, 15-45 parts of filler and 0.1-0.5 part of catalyst.
2. The moisture-curable polyurethane hot melt adhesive for aluminum-plastic composite as claimed in claim 1, wherein the polycarbonate diol has a number average molecular weight of 2000-4000g/mol, the hydroxyl-terminated polybutadiene has a number average molecular weight of 3000-5000g/mol, the alicyclic diisocyanate is dimer acid diisocyanate DDI, and the chemical structural formula is shown in the specification
Figure FDA0003702212570000011
3. The moisture-curing polyurethane hot melt adhesive for aluminum-plastic composite according to claim 1, wherein the filler is one or more of ground calcium carbonate, nano calcium carbonate and light calcium carbonate.
4. The moisture-curing polyurethane hot melt adhesive for aluminum-plastic composite according to claim 1, wherein the catalyst is dibutyltin dilaurate.
5. The moisture-curing polyurethane hot melt adhesive for aluminum-plastic composite according to claim 1, wherein the mass fraction of isocyanato NCO in the moisture-curing polyurethane hot melt adhesive for aluminum-plastic composite is 3-6%.
6. The moisture-curing polyurethane hot melt adhesive for aluminum-plastic compounding of any one of claims 1 to 5, wherein the preparation method of the moisture-curing polyurethane hot melt adhesive for aluminum-plastic compounding comprises the following steps:
putting polycarbonate diol and hydroxyl-terminated polybutadiene into a reaction kettle, mixing, heating to 110 ℃ under the vacuum degree of-0.1 MPa to remove water for 1 hour, cooling to 80 ℃, adding a set amount of alicyclic diisocyanate, adding a catalyst, stirring for 1 hour, sequentially adding dicyclopentadiene and a filler, monitoring the NCO content by a potentiometric titration method to meet a preset requirement, stopping reaction, taking out of the kettle, and packaging to obtain the hot melt adhesive.
7. The moisture-curable polyurethane hot melt adhesive for aluminum-plastic composite according to any one of claims 1 to 5, wherein the melt viscosity at 140 ℃ is 6700-9550 mPa-s according to Brookfield-ASTM D3236.
8. The moisture-curable polyurethane hot melt adhesive for aluminum-plastic composite as claimed in any one of claims 1 to 5, wherein the open time of the moisture-curable polyurethane hot melt adhesive for aluminum-plastic composite is less than 5 minutes as determined by HG/T3716-2003.
9. The moisture-curing polyurethane hot melt adhesive for aluminum-plastic compounding as claimed in any one of claims 1 to 5, wherein the initial bonding strength and the shear strength to polypropylene, PET and polyvinyl chloride are respectively greater than 0.55MPa and 3.50MPa, and the initial bonding strength and the shear strength to aluminum alloy are respectively greater than 1.50MPa and 7.0MPa, as determined by GB/T7214-2008, and the moisture-curing polyurethane hot melt adhesive for aluminum-plastic compounding can be used for bonding between aluminum materials and plastics and bonding between metals and metals.
CN202210695937.XA 2022-06-20 2022-06-20 Moisture-curing polyurethane hot melt adhesive for aluminum-plastic compounding Pending CN114958272A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116144311A (en) * 2022-12-24 2023-05-23 烟台德邦科技股份有限公司 Polyurethane hot melt adhesive and preparation method thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1502640A (en) * 2002-11-20 2004-06-09 F.C.I.株式会社 Thermoplastic polyurethane, method and apparatus for producing same
JP2020097651A (en) * 2018-12-17 2020-06-25 Dic株式会社 Moisture-curable polyurethane hot-melt resin composition, adhesive, and article
WO2021159377A1 (en) * 2020-02-13 2021-08-19 Henkel Ag & Co. Kgaa Reactive hot melt adhesive composition and use thereof
CN114479753A (en) * 2022-02-21 2022-05-13 北京高盟新材料股份有限公司 Single-component moisture curing reaction type power battery tab insulating adhesive and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1502640A (en) * 2002-11-20 2004-06-09 F.C.I.株式会社 Thermoplastic polyurethane, method and apparatus for producing same
JP2020097651A (en) * 2018-12-17 2020-06-25 Dic株式会社 Moisture-curable polyurethane hot-melt resin composition, adhesive, and article
WO2021159377A1 (en) * 2020-02-13 2021-08-19 Henkel Ag & Co. Kgaa Reactive hot melt adhesive composition and use thereof
CN114479753A (en) * 2022-02-21 2022-05-13 北京高盟新材料股份有限公司 Single-component moisture curing reaction type power battery tab insulating adhesive and preparation method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
化学工业部科学技术情报研究所: "《新型聚氨酯树脂涂料生产技术与应用》", vol. 1, 化学工业部科学技术情报研究所出版, pages: 370 - 371 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116144311A (en) * 2022-12-24 2023-05-23 烟台德邦科技股份有限公司 Polyurethane hot melt adhesive and preparation method thereof

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Application publication date: 20220830