CN113480967B - High-temperature-resistant polyurethane hot melt adhesive and preparation method thereof - Google Patents
High-temperature-resistant 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
- C09J175/06—Polyurethanes from polyesters
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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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4202—Two or more polyesters of different physical or chemical nature
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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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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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
- C08G18/4804—Two or more polyethers of different physical or chemical nature
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- 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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Abstract
The invention provides a high-temperature-resistant polyurethane hot melt adhesive and a preparation method thereof, wherein the high-temperature-resistant polyurethane hot melt adhesive comprises a polymer formed by the reaction of the following components: 1-5 parts by mass of a cross-linking agent, 15-25 parts by mass of a first component polyether polyol, 5-25 parts by mass of a second component polyether polyol, 25-55 parts by mass of a polyester polyol, isocyanate and an additive. The adhesive film does not contain solvent and has the solid content of 100%, no micromolecule is released in the using process, the adhesive film is safe, environment-friendly and pollution-free, has the advantages of environment friendliness, long service life, high bonding strength, safety, reliability and the like, does not have the phenomena of particles and bubbling after sizing, is flexible and elastic after being cured, has extremely high temperature resistance, can be stably used at 200 ℃, and can be widely applied to the composite bonding of steel, wood, plastic products and other composite materials.
Description
Technical Field
The invention relates to the technical field of polyurethane hot melt adhesives, in particular to a high-temperature-resistant polyurethane hot melt adhesive and a preparation method thereof.
Background
Polyurethane hot melt adhesive is also called wet reaction type polyurethane hot melt adhesive, is solvent-free glue with NCO end capped and capable of reacting with water vapor in air to obtain extremely high strength, and is widely applied to industries such as automobile industry, wood industry, shoe bag industry, building industry, printing ink industry, bookbinding, railway construction and the like since the fact that the German researchers in 1940 find that triphenylmethane-4, 4' -triisocyanate can bond metal and sodium butyrate rubber. Compared with the traditional hot melt adhesive, the polyurethane hot melt adhesive has more excellent comprehensive performance, has the characteristics of no solvent, high initial viscosity, quick positioning during assembly and the like of the common hot melt adhesive, and has the specific performances of water resistance, heat resistance, cold resistance, creep resistance, medium resistance and the like of the reactive liquid adhesive. The glue-applying temperature (120 ℃) is lower than that of the common hot melt adhesive (150-180 ℃), can be used for bonding and compounding certain plastic parts, and is favored by the modern automatic assembly industry. The adhesive has the characteristics of no water and solvent and 100% of solid content, is a high-performance environment-friendly adhesive, meets the requirements of increasingly important environments at home and abroad, and has extremely high development in recent years. However, domestic high-performance polyurethane hot melt adhesive is subject to technical reasons, is late to start, has weak foundation, and is seriously dependent on import, wherein the high-temperature-resistant polyurethane hot melt adhesive applied to the aerospace field and the high-speed railway field is a direction needing key breakthrough, international factories such as 3M, bostii, HBs Fuller, national Starch, astand and other companies monopolize core technologies, especially the current trade protection is mainly raised, and certain developed international congestion technologies monopolize to be supplied for threat, so that the supply chain safety of related industries is seriously affected. Although the development of the domestic polyurethane hot melt adhesive is rapid, the high-end product is still deficient, so that the development of corresponding imported substitutes is extremely important. In view of the above, the inventor has developed a new high temperature resistant polyurethane hot melt adhesive and a preparation method thereof through long-term special research.
Disclosure of Invention
The invention aims to solve the technical problems, and is realized by adopting the following technical scheme:
in a first aspect, the invention provides a high temperature resistant hydrolysis resistant polyurethane hot melt adhesive, which is characterized in that the hot melt adhesive comprises a polymer formed by the reaction of the following components:
a cross-linking agent, a first component polyether polyol, a second component polyether polyol, a polyester polyol, isocyanate and a proper amount of additives;
wherein the crosslinking agent is a high molecular aliphatic polyfunctional hydroxyl compound, characterized in that the polyfunctional hydroxyl compound has 3 to 10 hydroxyl groups, preferably the polyfunctional hydroxyl compound has 4 to 7 hydroxyl groups, more preferably the polyfunctional hydroxyl compound has 4 to 6 hydroxyl groups, most preferably the polyfunctional hydroxyl compound has 6 hydroxyl groups.
The crosslinking agent is an aliphatic polyfunctional hydroxyl compound, characterized in that the polyfunctional hydroxyl compound has an average molecular weight of 3000 to 50000, preferably the polyfunctional hydroxyl compound has an average molecular weight of 5000 to 20000.
Examples of commercially available high molecular weight polyol curing agents include specflex R, voralux R polyol from dow chemistry, voralux R polyol, and multranol R polyol multranol R-specific polyol and ultra cel flexible polyol from bayer materials science, ltd.
The first component polyether polyol is aliphatic polyether polyol, and is characterized in that the polyether polyol has two functionalities, and the polyether polyol is selected from homopolymers or copolymers formed by polymerizing one or more monomers of ethylene glycol, 1, 3-butanediol, 1, 4-butanediol, diethylene glycol, neopentyl glycol, 2-methyl-1, 3-propanediol, hexanediol, 3-methyl-1, 5-pentanediol and 1, 4-cyclohexanedimethanol, preferably, the polyether polyol is selected from homopolymers or copolymers formed by hexanediol and 1, 4-butanediol. The polyether polyol is characterized in that the polyether polyol has an average molecular weight of 200 to 4000, preferably a molecular weight of 500 to 3000.
The second component polyether polyol is aromatic ring-containing polyether polyol, and is characterized in that the aromatic ring-containing polyether polyol contains 1-25wt% of aromatic rings.
Preferably, the polyether polyol containing aromatic rings contains 4 to 15 weight percent of aromatic rings.
The polyether polyol containing aromatic rings is characterized in that the aromatic rings in the polyol are all-carbon aromatic rings or heteroatom-containing aromatic rings. The aromatic ring is one of hydroquinone, resorcinol, naphthalene diphenol, bisphenol A, bisphenol S, terephthalyl alcohol, isophthalyl alcohol, phthalic acid dimethanol, 2, 5-furan dimethanol, terephthalyl alcohol or diphenyl ether diphenol.
The molecular weight of the polyether polyol containing the aromatic ring is 190-6000, preferably 500-5000.
The polyester polyol is aliphatic polyester polyol, and is characterized in that the polyester polyol is obtained by reacting aliphatic dibasic acid with aliphatic dihydric alcohol. Wherein the aliphatic dihydric alcohol is any one or a mixture of more than one of ethylene glycol, 1, 3-butanediol, 1, 4-butanediol, diethylene glycol, neopentyl glycol, 2-methyl-1, 3-propanediol, hexanediol, 3-methyl-1, 5-pentanediol and 1, 4-cyclohexanedimethanol, and preferably the aliphatic dihydric alcohol is 1, 4-butanediol, hexanediol or a mixture thereof.
The aliphatic polybasic acid is any one or a mixture of a plurality of succinic acid, adipic acid, azelaic acid and sebacic acid;
the isocyanate comprises one or two of aromatic isocyanate and aliphatic isocyanate. The aromatic isocyanate is preferably used in an amount of 90 mol% or more, more preferably 95 mol% or more, and particularly preferably 100 mol%.
The aromatic isocyanate may be an aromatic diisocyanate. Aromatic diisocyanates include, but are not limited to, one or more of 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, 2' -diphenylmethane diisocyanate, 2,4' -diphenylmethane diisocyanate, 4' -diphenylmethane diisocyanate, 1, 5-naphthalene diisocyanate, p-phenylene diisocyanate, m-phenylene diisocyanate.
The aliphatic isocyanate may be aliphatic diisocyanate. Aliphatic diisocyanates include, but are not limited to, one or more of ethylene diisocyanate, 2, 4-trimethylhexamethylene diisocyanate, 1, 6-hexamethylene diisocyanate. The aliphatic isocyanate may be an alicyclic diisocyanate. Alicyclic diisocyanates include, but are not limited to, one or more of 1, 4-cyclohexane diisocyanate, 4' -dicyclohexylmethane diisocyanate, isophorone diisocyanate, and norbornane diisocyanate.
Preferably, the isocyanate is TDI or MDI, more preferably the isocyanate is MDI
The optional additives in the polyurethane hot melt adhesive comprise one or more of catalysts, stabilizers, antioxidants and anti-aging agents, wherein the catalysts are preferably amine catalysts, more preferably DMDEE, the stabilizers are preferably benzoyl chloride, the antioxidants are preferably Irganox 245, the anti-aging auxiliary agents are preferably UV-531, and the additives are all available commercially and can be used according to the instruction of the commodity instruction.
In a second aspect of the present invention, there is provided a method for preparing a high temperature resistant polyurethane hot melt adhesive, characterized in that the polyurethane hot melt adhesive comprises the following preparation steps: mixing a cross-linking agent, a first component polyether polyol, a second component aromatic ring-containing polyether polyol and a polyester polyol, heating to 110-150 ℃ to melt to form uniform liquid, degassing for 30min under vacuum (0.01 MPa), cooling to about 80 ℃, adding isocyanate into the uniform liquid, stirring for 30min at the temperature of 80 ℃ and normal pressure, reducing the stirring rotation speed within the last 40min, adding an additive, reducing bubble generation, and pouring into a container while the uniform liquid is hot for airtight preservation.
The preparation of the polyurethane hot melt adhesive is characterized in that the ratio of the number of NCO in isocyanate to the total number of hydroxyl groups in a cross-linking agent, a first component polyether polyol, a second component polyether polyol, a first component polyester polyol and a second component polyester polyol is R, wherein R is between 1.1 and 2.5, and preferably, the R value is between 1.3 and 2.0.
The preparation of the polyurethane hot melt adhesive is characterized in that the mass ratio of the first component polyether polyol to the second component polyether polyol to the polyester polyol to the cross-linking agent is as follows: 15-25: 5-25: 25-55: 1 to 5.
The beneficial effects of the invention are as follows:
the moisture-curing polyurethane hot melt adhesive and the preparation method thereof are characterized in that the moisture-curing polyurethane hot melt adhesive does not contain solvent, has the solid content of 100 percent, is free from micromolecule release in the use process, is safe and environment-friendly and pollution-free, has the advantages of environmental friendliness, long service life, high bonding strength, safety, reliability and the like, has no particle and bubbling phenomenon after sizing, is flexible and elastic after glue curing, has extremely high temperature resistance, can be stably used at 200 ℃, and can be widely applied to the composite bonding of steel, wood, plastic products and other composite materials.
Drawings
FIG. 1 is a schematic diagram of shear strength versus 200℃hanging weight sample preparation.
Detailed Description
In order that the manner in which the above recited features, objects and advantages of the present invention are obtained will become readily apparent, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings. Based on the examples in the embodiments, those skilled in the art can obtain other examples without making any inventive effort, which fall within the scope of the invention.
The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
Example 1
2 parts by mass of a crosslinking agent (hydroxyl number 6, mn=12000), 20 parts by mass of a first-component polyether polyol PPG1000 (mn=1000), 15 parts by mass of a second-component aromatic-ring-containing polyether polyol (polypropylene oxide with hydroquinone as an initiator, aromatic ring content 7.6%, mn=1000), 45 parts by mass of a polyhexamethylene adipate (mn=2000) were weighed, melted to form a uniform liquid, degassed under vacuum (0.01 MPa) for 30 minutes, cooled to around 80 ℃, 22 parts by mass of MDI were added thereto, stirred at 80 ℃ for 30 minutes under normal pressure, the stirring speed was reduced in the last 40 minutes, an auxiliary agent was added, bubble generation was reduced, and then the mixture was poured into a container to be hermetically stored while hot.
Example 2
Weighing 2.5 parts by mass of a cross-linking agent (hydroxyl number 4.7, mn=8225), 15 parts by mass of a first-component polyether polyol PPG2000 (Mn=2000), 8 parts by mass of PTMEG650 (Mn=650), 15 parts by mass of a second-component aromatic-ring-containing polyether polyol (polypropylene oxide with hydroquinone as an initiator, aromatic ring content 6.3%, mn=1200), 39 parts by mass of polybutylene adipate (Mn=1000), heating to 130 ℃ to melt to form uniform liquid, degassing for 30min under vacuum (0.01 MPa), cooling to about 80 ℃, adding 25 parts by mass of MDI into the mixture, stirring for 30min under normal pressure at 80 ℃, reducing stirring rotation speed in the last 40min, adding an auxiliary agent, reducing bubble generation, and pouring the mixture into a container while hot for airtight preservation.
Example 3
1.5 parts by mass of a crosslinking agent (hydroxyl number 6.9, mn=12420), 23 parts by mass of a first-component polyether polyol (EO-capped PO, EO/po=1; 4, mn=1750), 22 parts by mass of a second-component aromatic-ring-containing polyether polyol (polypropylene oxide with hydroquinone as an initiator, aromatic ring content 7.6%, mn=1000), 15 parts by mass of polyhexamethylene adipate (mn=1000), 25 parts by mass of polyhexamethylene adipate (mn=2000), heating to 130 ℃ to melt to form a uniform liquid, degassing under vacuum (0.01 MPa) for 30min, cooling to around 80 ℃, adding 24 parts by mass of MDI, stirring at 80 ℃ for 30min under normal pressure, reducing stirring speed in the last 40min, adding an auxiliary agent, reducing bubble generation, and pouring into a container while hot for airtight preservation.
Note that: as shown in fig. 1, the shear strength and 200 ℃ hanging weight sample preparation modes are as follows: to press the hot melt adhesive to 12g/ft 2 The coating amount is 1inch applied to the end of a 1inch 10inch steel plate 2 In the area and the two steel plates are mutually overlapped, the coating area is 1inch 2 After curing for 48 hours, the shearing strength is tested by a universal material tester; the hanging weight at 200 ℃ is that one end is fixed, the lower end is hung with a 1kg weight, the weight is placed in a 200 ℃ oven and baked for 1h, if the weight falls, the weight is judged to be unqualified, and if the weight does not fall, the weight is judged to be qualified, and reference is made to the attached figure 1.
The foregoing has shown and described the basic principles, principal features and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the above-described embodiments, and that the above-described embodiments and descriptions are only preferred embodiments of the present invention, and are not intended to limit the invention, and that various changes and modifications may be made therein without departing from the spirit and scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (2)
1. A preparation method of high-temperature-resistant polyurethane hot melt adhesive is characterized in that,
a high temperature resistant polyurethane hot melt adhesive comprising a polymer formed by the reaction of:
1-5 parts by mass of a cross-linking agent, 15-25 parts by mass of aliphatic polyether polyol, 5-25 parts by mass of hydroquinone-containing polyether polyol, 25-55 parts by mass of polyester polyol, isocyanate and a proper amount of additives;
the aliphatic polyether polyol has two functionalities, is selected from homopolymers or copolymers formed by polymerizing one or more monomers in ethylene glycol, 1, 3-butanediol, 1, 4-butanediol, diethylene glycol, neopentyl glycol, 2-methyl-1, 3-propanediol, hexanediol, 3-methyl-1, 5-pentanediol and 1, 4-cyclohexanedimethanol, and has a molecular weight of 500-3000;
the molecular weight of the hydroquinone-containing polyether polyol is 190-6000;
the ratio of the number of NCO in the isocyanate to the total number of hydroxyl groups in the cross-linking agent, the aliphatic polyether polyol, the hydroquinone-containing polyether polyol and the polyester polyol is R, wherein R is between 1.1 and 2.5;
the cross-linking agent is aliphatic high polymer polyol with 3-10 hydroxyl groups, and the average molecular weight of the cross-linking agent is 3000-50000;
the free NCO content in the hot melt adhesive is 1-4%, and the hot melt adhesive has the viscosity of 4000-25000 mpa.s at 120 ℃;
the preparation method comprises the following preparation steps: mixing a cross-linking agent, aliphatic polyether polyol, hydroquinone-containing polyether polyol and polyester polyol, heating to 110-150 ℃ to melt to form uniform liquid, degassing for 30min under vacuum, cooling to about 80 ℃, adding isocyanate, stirring for 30min at 80 ℃ and normal pressure, reducing the stirring rotation speed within the last 40min, adding an additive, reducing bubble generation, and pouring into a container while the container is hot for airtight preservation.
2. The method for preparing the high-temperature-resistant polyurethane hot melt adhesive according to claim 1, which is characterized in that: the vacuum condition is 0.01MPa.
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| CN110358072A (en) * | 2019-08-16 | 2019-10-22 | 荆晓东 | The synthetic method of high activity aromatic series unsaturated polyether polyol |
| CN110903802A (en) * | 2019-12-06 | 2020-03-24 | 烟台德邦科技有限公司 | Moisture-curing polyurethane hot melt adhesive for acoustic elements and preparation method thereof |
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Denomination of invention: A high-temperature resistant polyurethane hot melt adhesive and its preparation method Effective date of registration: 20230829 Granted publication date: 20230523 Pledgee: Tongling Branch of Postal Savings Bank of China Ltd. Pledgor: Anhui Zhongxia Packaging Technology Co.,Ltd. Registration number: Y2023980054378 |