CN114907800A - Moisture-curing polyurethane hot-melt adhesive and preparation method thereof - Google Patents
Moisture-curing polyurethane hot-melt adhesive and preparation method thereof Download PDFInfo
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- CN114907800A CN114907800A CN202210518679.8A CN202210518679A CN114907800A CN 114907800 A CN114907800 A CN 114907800A CN 202210518679 A CN202210518679 A CN 202210518679A CN 114907800 A CN114907800 A CN 114907800A
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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
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3296—Hydroxyamines being in latent form
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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
- C08G18/4825—Polyethers containing two hydroxy groups
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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
- C08G18/4829—Polyethers containing at least three hydroxy groups
-
- 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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- 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
- C08G18/65—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
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
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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
- C08G18/65—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
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6688—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a moisture-curing polyurethane hot-melt adhesive which is prepared by reacting 40-70 equivalent of polyol, 20-35 equivalent of isocyanate, 10-30 equivalent of latent curing polyurethane, 5-15 equivalent of acrylonitrile, 5-15 equivalent of methyl methacrylate and 0.5-1.5 equivalent of azodiisobutyronitrile. Firstly, mixing polyol and isocyanate to prepare a prepolymer containing NCO; adding latent curing polyurethane, dropwise adding a mixture of acrylonitrile and methyl methacrylate, adding part of azodiisobutyronitrile at intervals of 1h, and then decompressing and pumping out unreacted monomers to obtain the adhesive. When the latent curing polyurethane meets moisture or water vapor, the latent curing polyurethane is quickly decomposed into a compound containing an active hydrogen group, the compound has higher activity than water in reaction with an NCO group, the initial viscosity of the adhesive can be obviously improved, and the curing time of NCO is greatly shortened.
Description
The technical field is as follows:
the invention belongs to the field of polyurethane hot melt adhesive, and particularly relates to a moisture-curable polyurethane hot melt adhesive and a preparation method thereof.
Background art:
outdoor sports clothing must be able to absorb moisture and perspire in time, breathable and warm, skin-friendly and soft. In order to meet the requirements, a layer of waterproof moisture-permeable film is usually attached to the fabric of some current sports clothes, so that the fabric has certain waterproof performance and windproof performance, and meanwhile, because the film has a hydrophilic-hydrophobic chain segment, sweat can be discharged through the adsorption-diffusion-desorption process, so that the film has certain moisture-permeable performance. Moisture-curable Polyurethane (PUR) is mostly adopted as an adhesive in the process of compounding the film and the fabric, but the adhesive has the defects of long curing time and low bonding fastness.
The invention content is as follows:
in order to solve the problems of the adhesive, the invention provides a rapid adhesive with high cohesiveness and a preparation method thereof.
In order to achieve the purpose, the invention adopts the following technical scheme.
A moisture curing type polyurethane hot melt adhesive is prepared by reacting 40-70 equivalent of polyol, 20-35 equivalent of isocyanate, 10-30 equivalent of latent curing type polyurethane, 5-15 equivalent of acrylonitrile, 5-15 equivalent of methyl methacrylate and 0.5-1.5 equivalent of azodiisobutyronitrile.
The polyol is one or more of polyoxypropylene diol (M ═ 2000), polyoxypropylene triol (M ═ 6000) and polytetrahydrofuran diol (M ═ 5500).
The isocyanate is Toluene Diisocyanate (TDI) and diphenylmethane-4 , ,4 , -one or More of Diisocyanate (MDI), isophorone diisocyanate (IPDI), Xylylene Diisocyanate (XDI).
The latent curing polyurethane is one or more of oxazole compounds, cyclic amine compounds, ketimine compounds and the like. Preferably oxazole-4-carboxylic acid ethyl ester and toluenediamine butanone imine.
The preparation method of the moisture-curing polyurethane hot-melt adhesive comprises the following steps:
(1) firstly, mixing polyol and isocyanate to react for 2-10h at 60-100 ℃ to prepare a prepolymer containing NCO;
(2) adding a certain amount of latent curing polyurethane, and uniformly stirring;
(3) dropwise adding a mixture of acrylonitrile and methyl methacrylate for 5h, adding part of azodiisobutyronitrile at intervals of 1h, and continuously reacting at 60-100 ℃ for 5-10 h;
(4) and (3) decompressing at 125 ℃ and pumping out the unreacted monomers to obtain the prepared adhesive.
When the latent curing polyurethane meets moisture or water vapor, the latent curing polyurethane is quickly decomposed into a compound containing an active hydrogen group, the compound has higher activity than water in reaction with an NCO group, the initial viscosity of the adhesive can be obviously improved, and the curing time of NCO is greatly shortened.
The specific implementation mode is as follows:
example 1
20 equivalents of polyoxypropylene glycol (M2000), 50 equivalents of polytetrahydrofuran diol (5500), 10 equivalents of Toluene Diisocyanate (TDI), 15 equivalents of Xylylene Diisocyanate (XDI) were taken, and the mixture was refluxed at 100 ℃ for 10 hours, and then 20 equivalents of toluenediamine butanone imine was added thereto and stirred uniformly. And then, dropwise adding a mixture of 10 equivalents of acrylonitrile and 5 equivalents of methyl methacrylate for 5 times, wherein the dropwise adding time is 5 hours, 0.05 equivalent of azodiisobutyronitrile is added at intervals of 1 hour, continuously reacting for 6 hours at 80 ℃, and extracting the unreacted monomers under reduced pressure at 125 ℃ to obtain the prepared adhesive.
Example 2
20 equivalents of polyoxypropylene triol (M6000), 30 equivalents of polytetrahydrofuran diol (5500) and 35 equivalents of isophorone diisocyanate (IPDI) are taken to perform reflux reaction at 100 ℃ for 6 hours, and then 10 equivalents of oxazole-4-carboxylic acid ethyl ester are added to be uniformly stirred. And then, dropwise adding a mixture of 5 equivalents of acrylonitrile and 15 equivalents of methyl methacrylate for 5 times, wherein the dropwise adding time is 5 hours, 0.1 equivalent of azodiisobutyronitrile is added at intervals of 1 hour, continuously reacting for 10 hours at 60 ℃, and extracting the unreacted monomers under reduced pressure at 125 ℃ to obtain the prepared adhesive.
Example 3
20 equivalents of polyoxypropylene diol (M2000), 30 equivalents of polyoxypropylene triol (M6000) and 25 equivalents of Toluene Diisocyanate (TDI) were taken, reacted at 60 ℃ under reflux for 10 hours, and then 30 equivalents of toluene diamine butanone imine was added and stirred uniformly. And then, dropwise adding a mixture of 5 equivalents of acrylonitrile and 15 equivalents of methyl methacrylate for 5 times, wherein the dropwise adding time is 5h, 0.05 equivalent of azodiisobutyronitrile is added at intervals of 1h, continuously reacting for 6h at 80 ℃, and pumping out unreacted monomers under reduced pressure at 125 ℃ to finally obtain the prepared adhesive.
Example 4
7050 equivalents of polytetrahydrofuran diol (5500), 25 equivalents of Toluene Diisocyanate (TDI), and 10-lane diphenylmethane-4 are taken , ,4 , And (3) carrying out reflux reaction on diisocyanate (MDI) at 80 ℃ for 6 hours, then adding 15 equivalents of oxazole-4-carboxylic acid ethyl ester and 15 equivalents of toluenediamine butanone imine, and stirring uniformly. And then dropwise adding a mixture of 15 equivalents of methyl methacrylate for 5 times, wherein the dropwise adding time is 5 hours, adding 0.1 equivalent of azodiisobutyronitrile at intervals of 1 hour, continuously reacting for 4 hours at 100 ℃, and extracting the unreacted monomers under reduced pressure at 125 ℃ to obtain the prepared adhesive.
Comparative example 1
15 equivalents of polyoxypropylene diol (M2000), 15 equivalents of polyoxypropylene triol (M6000), 25 equivalents of polytetrahydrofuran diol (5500), and 25 equivalents of Toluene Diisocyanate (TDI) were taken and reacted at 80 ℃ under reflux for 6 hours. And then, dropwise adding a mixture of 15 equivalents of acrylonitrile and 15 equivalents of methyl methacrylate for 5 times, wherein the dropwise adding time is 5 hours, 0.04 equivalent of azodiisobutyronitrile is added at intervals of 1 hour, continuously reacting for 10 hours at 60 ℃, and extracting the unreacted monomers under reduced pressure at 125 ℃ to obtain the prepared adhesive.
The products of examples 1 to 4, the product of comparative example 1 and the commercial product (4663 moisture-curable hot melt adhesive, Han Germany) were subjected to peel strength tests for 6h, 12h, 18h and 24h, respectively, according to the following test methods: preheating a hot melt adhesive product at 120 ℃ for 2h, coating the hot melt adhesive product on the surface of a wood board coated on a mesh plastic floor, controlling the gluing amount to be 30g/m2, gluing, compounding with a PVC film, naturally curing for 6h, 12h, 18h and 24h respectively in an environment with the room temperature of 25 ℃ and the relative humidity of 50% for 5s under pressure, and carrying out peeling test on the wood-plastic floor board cut pieces of 2.5 multiplied by 15cm by referring to GB/T2790-1995 by using an SANS tensile testing machine.
Open time tests were conducted on the products of examples 1-4, comparative example 1 and commercial products; the test method comprises the following steps: the products of examples 1 to 4 and comparative example 1 were preheated at 120 ℃ for 2h and poured onto smooth plates, with reference to the industry standard HG/T3716-2003, and the time (min) for which the surface of the adhesive layer was tacky was recorded at 1min intervals.
TABLE 1 product Performance test results for the examples, comparative examples and commercial products
Claims (5)
1. A moisture curing type polyurethane hot melt adhesive is prepared by reacting 40-70 equivalent weight of polyol, 20-35 equivalent weight of isocyanate, 10-30 equivalent weight of latent curing type polyurethane, 5-15 equivalent weight of acrylonitrile, 5-15 equivalent weight of methyl methacrylate and 0.5-1.5 equivalent weight of azodiisobutyronitrile.
2. The moisture-curable polyurethane hot melt adhesive according to claim 1, wherein: the polyol is one or more of polyoxypropylene diol (M ═ 2000), polyoxypropylene triol (M ═ 6000) and polytetrahydrofuran diol (M ═ 5500).
3. The moisture-curable polyurethane hot melt adhesive according to claim 1, wherein: the isocyanate is Toluene Diisocyanate (TDI) and diphenylmethane-4 , ,4 , -one or More of Diisocyanate (MDI), isophorone diisocyanate (IPDI), Xylylene Diisocyanate (XDI).
4. The moisture-curable polyurethane hot melt adhesive according to claim 1, wherein: the latent curing polyurethane is one or more of oxazole compounds, cyclic amine compounds, ketimine compounds and the like.
5. The preparation method of the moisture-curable polyurethane hot melt adhesive according to any one of claims 1 to 4 comprises the following steps:
(1) firstly, mixing polyol and isocyanate to react for 2-10h at 60-100 ℃ to prepare a prepolymer containing NCO;
(2) adding a certain amount of latent curing polyurethane, and uniformly stirring;
(3) dropwise adding a mixture of acrylonitrile and methyl methacrylate for 5h, adding part of azodiisobutyronitrile at intervals of 1h, and continuously reacting at 60-100 ℃ for 5-10 h;
(4) and (3) decompressing at 125 ℃ and pumping out the unreacted monomers to obtain the prepared adhesive.
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CN202210518679.8A CN114907800A (en) | 2022-05-12 | 2022-05-12 | Moisture-curing polyurethane hot-melt adhesive and preparation method thereof |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107922581A (en) * | 2015-06-29 | 2018-04-17 | 巴斯夫欧洲公司 | Reactive hot melt adhesive |
CN110698622A (en) * | 2019-10-12 | 2020-01-17 | 北京长润化工有限公司 | Ketimine latent curing agent, reactive polyurethane hot melt adhesive with ketimine latent curing agent and application of reactive polyurethane hot melt adhesive |
CN112852373A (en) * | 2021-02-04 | 2021-05-28 | 东莞市德聚胶接技术有限公司 | Moisture-curing type polyurethane hot melt adhesive |
CN114045143A (en) * | 2021-11-23 | 2022-02-15 | 广州市白云化工实业有限公司 | High-transparency reactive polyurethane hot melt adhesive and preparation method thereof |
-
2022
- 2022-05-12 CN CN202210518679.8A patent/CN114907800A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107922581A (en) * | 2015-06-29 | 2018-04-17 | 巴斯夫欧洲公司 | Reactive hot melt adhesive |
CN110698622A (en) * | 2019-10-12 | 2020-01-17 | 北京长润化工有限公司 | Ketimine latent curing agent, reactive polyurethane hot melt adhesive with ketimine latent curing agent and application of reactive polyurethane hot melt adhesive |
CN112852373A (en) * | 2021-02-04 | 2021-05-28 | 东莞市德聚胶接技术有限公司 | Moisture-curing type polyurethane hot melt adhesive |
CN114045143A (en) * | 2021-11-23 | 2022-02-15 | 广州市白云化工实业有限公司 | High-transparency reactive polyurethane hot melt adhesive and preparation method thereof |
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