CN113717678A - Light-moisture dual-curing polyurethane hot melt adhesive - Google Patents
Light-moisture dual-curing polyurethane hot melt adhesive Download PDFInfo
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- CN113717678A CN113717678A CN202111062244.9A CN202111062244A CN113717678A CN 113717678 A CN113717678 A CN 113717678A CN 202111062244 A CN202111062244 A CN 202111062244A CN 113717678 A CN113717678 A CN 113717678A
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- curing polyurethane
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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
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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
- C09J11/06—Non-macromolecular additives organic
Abstract
The invention relates to a light-moisture dual-curing polyurethane hot melt adhesive, which comprises the following components in parts by mass: 30-80 parts of polyol polymer, 20-40 parts of polyisocyanate compound, 0.5-10 parts of photobase generator, 5-30 parts of thermoplastic resin, 3-12 parts of tackifying resin, 0.1-5 parts of photosensitizer and 0.01-3 parts of catalyst. The photobase generator capable of generating primary amine by illumination is introduced into a polyurethane system, primary amino groups generated by illumination react with isocyanate groups quickly, carbon dioxide gas is not generated, bubbles are avoided, and the opening time has a certain adjustable space due to the delayed reaction characteristic of anions, so that the photobase generator can be used for bonding non-light-transmitting materials; due to the relatively fast crosslinking reaction, the polyurethane can be quickly fixed, and the initial adhesion of the polyurethane is improved.
Description
Technical Field
The invention relates to a reactive polyurethane hot melt adhesive, in particular to a light-moisture curing polyurethane hot melt adhesive, and belongs to the technical field of adhesives.
Background
The reactive polyurethane hot melt adhesive is an environment-friendly hot melt adhesive, not only has the process characteristic of convenient operation of common hot melt adhesives, but also can still be subjected to curing crosslinking reaction with moisture in the air at normal temperature due to the active isocyanate groups, so that excellent bonding performance, good flexibility, weather resistance and the like are obtained, and the reactive polyurethane hot melt adhesive is widely applied to various industries such as consumer electronics, woodwork, household appliances, textile and the like.
But because of the slow reaction rate of moisture and the low initial strength, a long dwell time is generally required to limit its application. The initial strength can be increased without changing the formulation body, usually by two approaches: 1) the amount of the catalyst is increased, but the thermal stability of the adhesive is deteriorated, and the generation of colloidal bubbles is caused by an excessively high curing rate. 2) A photo-curing system is introduced, the currently common free radical system has cation polymerization inhibition and no post-curing characteristic, and cannot be used for bonding of non-transparent materials, and the cation curing system is sensitive to moisture and corrosive to metals, so that the application of the cation curing system is limited.
Disclosure of Invention
In order to achieve the purpose, the invention introduces a kind of photobase generator, generates primary amine after being irradiated by ultraviolet light, and directly and rapidly reacts with isocyanate groups to achieve the effect of rapid positioning without influencing other properties after moisture curing. The invention provides a light-moisture dual-curing polyurethane hot melt adhesive which has certain controllable operation time, ensures that a cured product is not easy to generate bubbles, and can provide higher initial adhesion.
The technical scheme for solving the technical problems is as follows:
a light-moisture dual-curing polyurethane hot melt adhesive comprises the following components in parts by mass: 30-80 parts of polyol polymer, 20-40 parts of polyisocyanate compound, 0.5-10 parts of photobase generator, 5-30 parts of thermoplastic resin, 3-12 parts of tackifying resin, 0.1-5 parts of photosensitizer and 0.01-3 parts of catalyst.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, the photobase generator is a substance which can generate primary amine after light irradiation, and can be cobalt-ammonia complex, carbamate or formamide, etc., preferably a photobase generator of Fuji carbamate type, such as one or more of WPG041, WPG174 and WPG 025.
Further, the polyisocyanate compound is one or a mixture of several of methylene diphenyl diisocyanate (MDI), Hydrogenated Methylene Diphenyl Isocyanate (HMDI), Hexamethylene Diisocyanate (HDI), isophorone diisocyanate (IPDI), polymeric methylene diphenyl diisocyanate, Toluene Diisocyanate (TDI), polymethylene polyphenyl diisocyanate, Naphthalene Diisocyanate (NDI) or polymethylene polyphenyl isocyanate (PAPI).
Further, the molecular weight of the polyol polymer is 300-.
Further, the polyol polymer is one or a mixture of more of polyester polyol polymer, polyether polyol polymer and other polymers containing hydroxyl functions.
Still further, the polyester polyol polymer is one or more than two of common polyester polyol polymer, polycaprolactone polyol polymer and polycarbonate polyol polymer.
Wherein the common polyester polyol is a polymer produced by reacting acid or acid anhydride with corresponding alcohol, and is polymerized by at least one acid of adipic acid, sebacic acid, dodecanoic acid, isophthalic acid, terephthalic acid, phthalic anhydride and at least one alcohol of 1, 4-butanediol, diethylene glycol, neopentyl glycol, ethylene glycol, cyclohexanediol, diethylene glycol, 1, 6-hexanediol and 3-methyl-1, 5-pentanediol.
Wherein the polycaprolactone polyol is poly-epsilon-caprolactone polyol obtained by ring-opening polymerization of epsilon-caprolactone, and preferably one or two of Dasely PCL 210 and PCL 220.
Wherein the polycarbonate polyol is a polymer containing polycarbonate groups, such as one or more of polycarbonate 1, 6-hexanediol polyol, pentanediol, hexanediol, butanediol, propylene glycol copolyester, and polycyclohexane carbonate ethylene glycol polyol.
Still further, the polyether polyol may be at least one of a ring-opening polymer of ethylene glycol, propylene glycol, tetrahydrofuran, 3-methyltetrahydrofuran, and a random copolymer or a block copolymer of these or derivatives thereof.
Furthermore, the thermoplastic resin is thermoplastic acrylic resin, and the acrylic resin can contain hydroxyl active groups. Preferred examples thereof include BR103 and BR116 of Mitsubishi, ELVACITE 4197 or ELVACITE 2903 of Dianal Inc.
Further, the tackifying resin is one or a mixture of terpene resin, rosin resin and petroleum resin.
Further, the photosensitizer is one or more of acetophenone, benzophenone, Michler's ketone, benzil, benzoin ether, benzil dimethyl ketal, benzoyl benzoate, alpha-oxime acyl ester, thioxanthone, allylthiourea, o-tolylthiourea, sodium diethyldithiophosphate, soluble salts of aromatic sulfinic acid, N-disubstituted p-aminobenzonitrile compounds, tri-N-butyl phosphine, N-nitrosohydroxylamine derivatives, oxazolidine compounds, tetrahydro-1, 3-oxazine compounds, condensates of formaldehyde or acetaldehyde and diamine, anthracene and derivatives.
Further, the catalyst is one or more of dibutyltin dilaurate, stannous octoate, dibutylene acetate, triethylene diamine and DMDEE (dimorpholinyl diethyl ether).
The preparation method of the light-moisture dual-curing polyurethane hot melt adhesive comprises the following steps:
step one, heating 40-80 parts of polyol polymer, 10-30 parts of thermoplastic resin and tackifying resin to 120-140 ℃, and dehydrating for 2 hours in vacuum under the stirring condition of 300 r/min;
and step two, cooling to 100 ℃, continuously adding 10-30 parts of polyisocyanate compound, reacting for 1h at a stirring speed of 400r/min under a vacuum condition, adding the photobase generator and the photosensitizer subjected to vacuum dehydration in advance, stirring the catalyst for 30min under a vacuum condition, discharging, and storing in a vacuum seal and in a dark place.
The invention has the beneficial effects that: the photobase generator capable of generating primary amine by illumination is introduced into a polyurethane system, primary amino groups produced by illumination react with isocyanate groups quickly, carbon dioxide gas is not generated, bubbles are avoided, and meanwhile, due to the delayed reaction characteristic of anions, the opening time has a certain adjustable space, so that the photobase generator can be used for bonding non-light-transmitting materials. Due to the relatively fast crosslinking reaction, the polyurethane can be quickly fixed, and the initial adhesion of the polyurethane is improved.
Detailed Description
Example 1
Adding 30 parts by weight of poly (butylene adipate) polyol with molecular weight of 2000, 24 parts by weight of polyoxypropylene glycol with molecular weight of 1000, 8 parts by weight of poly (hexylene phthalate) glycol with molecular weight of 1000 and 12.5 parts by weight of polyacrylic resin BR103 into a reaction bottle, heating to 130-140 ℃, and carrying out vacuum dehydration for 2h under the stirring condition of 350 r/min; then, the temperature is reduced to 100 ℃, 24 parts of 4, 4' -diphenylmethane diisocyanate (MDI) is added, after reaction is carried out for 1 hour under the vacuum condition at the stirring speed of 450r/min, 1 part of photobase generator (WPG174), 0.3 part of photosensitizer (4-isopropyl thioxanthone) and 0.2 part of catalyst (DMDEE) are added, the mixture is continuously stirred for 30 minutes, and then the mixture is discharged and stored in a vacuum sealing and dark place.
Example 2
Adding 22 parts by weight of polyhexamethylene adipate polyol with the molecular weight of 2000, 28 parts by weight of polytetrahydrofuran with the molecular weight of 2000, 10 parts by weight of neopentyl glycol adipate diol with the molecular weight of 1000 and 18 parts by weight of polyacrylic resin (BR116) into a reaction bottle, heating to 120-140 ℃, and carrying out vacuum dehydration for 2 hours under the stirring condition of 350 r/min; then, the temperature is reduced to 100 ℃, 26 parts of 4, 4-diisocyanate dicyclohexylmethane (HMDI) is added, after reaction is carried out for 1h under the vacuum condition at the stirring speed of 450r/min, 3 parts of photobase generator (WPG174), 0.9 part of photosensitizer (2, 4-diethylthia-9-one) and 0.1 part of catalyst (DMDEE) are added, the mixture is continuously stirred for 30min, and then the mixture is discharged and stored in a vacuum sealing and dark place.
Example 3
Adding 18 parts by weight of polyhexamethylene adipate glycol with the molecular weight of 3500, 24 parts by weight of polycaprolactone glycol with the molecular weight of 2000, 17 parts by weight of polycarbonate diol with the molecular weight of 1000 and 17 parts by weight of polyacrylic resin (ELVACITE 4197) into a reaction bottle, heating to 120-140 ℃, and carrying out vacuum dehydration for 2 hours under the stirring condition of 350 r/min; then, the temperature is reduced to 100 ℃, 18 parts of 4, 4' -diphenylmethane diisocyanate (MDI) is added, after reaction is carried out for 1h under the vacuum condition at the stirring speed of 450r/min, 4.46 parts of photobase generator (WPG174), 1.46 parts of photosensitizer (2-isopropyl thioxanthone) and 0.08 part of catalyst (DMDEE) are added, the mixture is continuously stirred for 30min, and then the mixture is discharged and stored in a vacuum sealing and dark place.
Example 4
Adding 15 parts by weight of polyhexamethylene adipate glycol with a molecular weight of 3500, 25 parts by weight of polytetrahydrofuran ether glycol with a molecular weight of 1000, 15 parts by weight of polycarbonate diol with a molecular weight of 2000 and 20 parts by weight of polyacrylic resin (BR116) into a reaction bottle, heating to 120-140 ℃, and carrying out vacuum dehydration for 2 hours under the stirring condition of 350 r/min; then, the temperature is reduced to 100 ℃, 20 parts of 4, 4' -diphenylmethane diisocyanate (MDI) is added, after reaction is carried out for 1h under the vacuum condition at the stirring speed of 450r/min, 3.4 parts of photobase generator (WPG174), 1.45 parts of photosensitizer (4-isopropyl thioxanthone) and 0.15 part of catalyst (DMDEE) are added, the mixture is continuously stirred for 30min, and then the mixture is discharged and stored in a vacuum sealing and dark place.
Comparative example
Common reactive polyurethane hot melt adhesives: adding 15 parts by weight of polyhexamethylene adipate glycol with a molecular weight of 3500, 25 parts by weight of polytetrahydrofuran ether glycol with a molecular weight of 1000, 15 parts by weight of polycarbonate diol with a molecular weight of 2000 and 20 parts by weight of polyacrylic resin (BR116) into a reaction bottle, heating to 120-140 ℃, and carrying out vacuum dehydration for 2 hours under the stirring condition of 350 r/min; then, the temperature is reduced to 100 ℃, 20 parts of 4, 4' -diphenylmethane diisocyanate (MDI) is added, the mixture reacts for 1 hour under the vacuum condition at the stirring speed of 450r/min, 0.15 part of catalyst (DMDEE) is added, the mixture is continuously stirred for 30 minutes and then discharged, and the mixture is stored in a vacuum sealing and dark place.
The results of the performance tests of the products obtained in examples 1 to 4 and comparative example are shown in Table 1.
Opening time: the hot melt adhesives obtained in the examples and comparative examples were dispensed onto a glass substrate at a certain rate by a dispenser with a single dispensing amount of about 10mg, the dispensing was terminated and a timer was started, the dispensing was covered with release paper every 30 seconds, a 100g weight was used to press the adhesive for 10 seconds until the adhesive could not be pressed down, and the time until the pressed area was significantly changed was recorded, which was the UV light exposure open time.
Using a dispenser to dispense the hot melt adhesive obtained in the examples and comparative examples onto a glass substrate at a certain speed by a plurality of single points of about 10mg, immediately irradiating the adhesive line by using a 365nm UV-LED light source after dispensing is finished, wherein the irradiation energy is 10000mJ/cm2Starting after the irradiation is finishedAnd (4) timing, covering the glue dots with release paper every 30s, pressing for 10s by using a 100g weight until the glue dots cannot be pressed down, and recording the time before the pressed area is obviously changed, wherein the time is the UV illumination opening time.
And (3) testing the bonding strength: the hot melt adhesives obtained in examples and comparative examples were applied by dispensing at 110 ℃ onto a polycarbonate substrate with a width of about 2mm using a dispenser. Then, the glue line was irradiated with UV-LED light source of 365nm at an irradiation energy of 10000mJ/cm2After the irradiation was completed, another polycarbonate substrate was then attached to the polycarbonate substrate, and the adhesive strength was measured 30min and 7d after dispensing under curing conditions of 25 ℃ temperature and 50% humidity RH. The prepared sample for evaluation of adhesive strength was pulled at a speed of 300mm/min in the shear direction using a tensile tester, and the shear strength to the polycarbonate substrate was measured. The results are shown in the following table
The comparative data show that the polyurethane hot melt adhesive prepared by the invention has higher initial adhesion and higher final adhesion strength.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. The light-moisture dual-curing polyurethane hot melt adhesive is characterized by comprising the following components in parts by mass: 30-80 parts of polyol polymer, 20-40 parts of polyisocyanate compound, 0.5-10 parts of photobase generator, 5-30 parts of thermoplastic resin, 3-12 parts of tackifying resin, 0.1-5 parts of photosensitizer and 0.01-3 parts of catalyst.
2. The photo-moisture dual-curing polyurethane hot melt adhesive according to claim 1, wherein the photo-base generator is cobalt-ammonia complex, urethane or formamide.
3. The photo-moisture dual-curing polyurethane hot melt adhesive according to claim 1, wherein the polyol polymer is a polyester polyol polymer and/or a polyether polyol polymer.
4. The photo-moisture dual-curing polyurethane hot melt adhesive as claimed in claim 3, wherein the molecular weight of the polyol polymer is 300-8000.
5. The photo-moisture dual-curing polyurethane hot melt adhesive according to claim 1,
the polyester polyol polymer is one or more than two of common polyester polyol polymer, polycaprolactone polyol polymer and polycarbonate polyol polymer;
the common polyester polyol polymer is formed by polymerizing at least one of adipic acid, sebacic acid, dodecanoic acid, isophthalic acid, terephthalic acid, phthalic acid and phthalic anhydride with at least one of 1, 4-butanediol, diethylene glycol, neopentyl glycol, ethylene glycol, cyclohexanediol, diethylene glycol, 1, 6-hexanediol and 3-methyl-1, 5-pentanediol;
the polyether polyol polymer is at least one of ring-opening polymers of ethylene glycol, propylene glycol, tetrahydrofuran and 3-methyltetrahydrofuran, and random copolymers or block copolymers of the ring-opening polymers and the ring-opening polymers or the derivatives of the ring-opening polymers.
6. The photo-moisture dual-curing polyurethane hot melt adhesive according to claim 1, wherein the polyisocyanate compound is one or more of methylene diphenyl diisocyanate, hydrogenated methylene diphenyl isocyanate, hexamethylene diisocyanate, isophorone diisocyanate, polymeric methylene diphenyl diisocyanate, toluene diisocyanate, polymethylene polyphenyl diisocyanate, naphthalene diisocyanate or polymethylene polyphenyl isocyanate.
7. The photo-moisture dual-curing polyurethane hot melt adhesive according to claim 1, wherein the thermoplastic resin is a thermoplastic acrylic resin.
8. The light-moisture dual-curing polyurethane hot melt adhesive as claimed in claim 1, wherein the tackifying resin is one or a mixture of terpene resin, rosin resin and petroleum resin.
9. The photo-moisture dual-curing polyurethane hot melt adhesive according to claim 1, wherein the photosensitizer is one or more of acetophenone, benzophenone, Michler's ketone, benzil, benzoin ether, benzil dimethyl ketal, benzoyl benzoate, α -acyloxime ester, thioxanthone, allylthiourea, o-tolylthiourea, sodium diethyldithiophosphate, soluble salts of aromatic sulfinic acids, N-disubstituted p-aminobenzonitrile compounds, tri-N-butylphosphine, N-nitrosohydroxylamine derivatives, oxazolidine compounds, tetrahydro-1, 3-oxazine compounds, condensates of formaldehyde or acetaldehyde with diamine, anthracene and derivatives.
10. The photo-moisture dual-curing polyurethane hot melt adhesive according to claim 1, wherein the catalyst is one or more of dibutyltin dilaurate, stannous octoate, dibutylene acetate, triethylene diamine and dimorpholinyl diethyl ether.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111062244.9A CN113717678A (en) | 2021-09-10 | 2021-09-10 | Light-moisture dual-curing polyurethane hot melt adhesive |
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| CN202111062244.9A CN113717678A (en) | 2021-09-10 | 2021-09-10 | Light-moisture dual-curing polyurethane hot melt adhesive |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115806795A (en) * | 2022-12-29 | 2023-03-17 | 韦尔通(厦门)科技股份有限公司 | UV (ultraviolet) delayed curing reaction type polyurethane hot melt adhesive with high initial bonding strength and low free isocyanate content and preparation method thereof |
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| JP2016074783A (en) * | 2014-10-03 | 2016-05-12 | 積水化学工業株式会社 | Photo- and moisture-curable resin composition |
| JP2017114992A (en) * | 2015-12-22 | 2017-06-29 | 三洋化成工業株式会社 | Photocurable composition |
| CN112724907A (en) * | 2020-12-29 | 2021-04-30 | 厦门韦尔通科技有限公司 | Light-moisture-curing polyurethane hot-melt adhesive for bonding opaque substrates and preparation method thereof |
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2021
- 2021-09-10 CN CN202111062244.9A patent/CN113717678A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2016074783A (en) * | 2014-10-03 | 2016-05-12 | 積水化学工業株式会社 | Photo- and moisture-curable resin composition |
| JP2017114992A (en) * | 2015-12-22 | 2017-06-29 | 三洋化成工業株式会社 | Photocurable composition |
| CN112724907A (en) * | 2020-12-29 | 2021-04-30 | 厦门韦尔通科技有限公司 | Light-moisture-curing polyurethane hot-melt adhesive for bonding opaque substrates and preparation method thereof |
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| 谢刚等: "高分子光引发剂研究进展", 《江西化工》 * |
| 钟荣等: "光产碱反应及其应用", 《高分子通报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115806795A (en) * | 2022-12-29 | 2023-03-17 | 韦尔通(厦门)科技股份有限公司 | UV (ultraviolet) delayed curing reaction type polyurethane hot melt adhesive with high initial bonding strength and low free isocyanate content and preparation method thereof |
| CN115806795B (en) * | 2022-12-29 | 2023-08-29 | 韦尔通科技股份有限公司 | UV delay curing reaction type polyurethane hot melt adhesive with high initial bonding strength and low free isocyanate content and preparation method thereof |
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