CN105017503A - Synthetic method of reaction type PU (polyurethane) hot melt adhesive prepolymer - Google Patents
Synthetic method of reaction type PU (polyurethane) hot melt adhesive prepolymer Download PDFInfo
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- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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- 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
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- 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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- 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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- 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
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
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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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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6614—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6618—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 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
- 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
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention relates to a synthetic method of a reaction type PU (polyurethane) hot melt adhesive prepolymer. MDI (methylene diphenyl diisocyanate) has a polymerization reaction with polyester diol, polycaprolactone diol and polytetrahydrofuran diol, N,N'-di-sec-butyl-4,4'-methylenedianiline is used as a chain extender in the reaction process, the high-strength reaction type PU hot melt adhesive prepolymer is obtained, and the prepolymer is applied to a reaction type PU hot melt adhesive and has higher bonding strength and long-term storage stability.
Description
Technical field
The present invention relates to a kind of synthetic method of reaction type polyurethane hot-melt adhesive prepolymer.
Background technology
Reactive polyurethane hot melt is generally make base-material with NCO client-based prepolymer, is equipped with nonreactive thermoplastic resin and the additive such as solvent misture and oxidation inhibitor, catalyzer, filler with isocyanate group formulated.Time bonding, sizing agent heating and melting fluidly applies applying glue, after two kinds of clung body laminatings, glue-line cooling cohesion obtains initial bonding force at once, active NCO group then in glue-line is reacted with the moisture of the moisture in air, adherend surface attachment and active hydrogen group again, produce chemical crosslinking cure, bonding force, thermotolerance etc. are significantly improved.In recent years, because the breakthrough of technology and equipment overcomes these problems gradually, application widely.
Crystalline polyurethane prepolymer is the important component part of moisture-curable polyurethane hot melt adhesive, and its characteristic decides the final use properties of hot melt adhesive and use range.Soft section in usual polyurethane prepolymer adopts crystalline polyether glycol (PTMEG) or polyester glycol (PBA/PHA), and hard section adopts diphenylmethanediisocyanate (i.e. MDI).The soft section of polyester glycol usually adopted is poly-hexanodioic acid-butyleneglycol type or the poly-hexanodioic acid-hexylene glycol ester type of 2000-4000 molecular weight, the MDI that hard section adopts is mainly MDI-100, because MDI-100 reactive behavior is high, usually by the main NCO client-based prepolymer in order to preparation feedback polyurethane hot melt.Great many of experiments shows, the hot melt adhesive prepolymer bonding strength adopting this synthetic technology to prepare is higher, good to the sticking power at interface, but there is the distinct disadvantage of shelf-stable difference, be mainly manifested in period of storage short, easy crystallization, incrustation phenomenon, make troubles to use, in fact limit the widespread use of reactive hot-melt.
Summary of the invention
The present invention is mainly when synthetic prepolymer, and hard section and soft section of interpolation employ diphenylmethanediisocyanate and the polycaprolactone glycol of two limbs.Namely part MDI-50 and PCL-2000 is adopted.Due to the two limbs diphenylmethanediisocyanates (namely 2, the another kind of main isomer of 4 '-MDI, MDI) containing 50% in MDI-50.MDI-50, is liquid form under normal temperature, in actual prepolymer building-up reactions, adds appropriate MDI-50, can regulate crystallization degree and the reactive behavior of performed polymer, effectively solves the package stability of hot melt adhesive.And add appropriate PCL, effectively can solve resistance to hydrolysis and the weather resisteant of hot melt adhesive, increasing action is risen to obtain to the shelf-stable improving hot melt adhesive.
In order to solve poor, the easy crystallization of the relative package stability of polyurethane hot melt in prior art, incrustation problem, the invention provides a kind of synthetic method of reactive hot-melt prepolymer, the reactive polyurethane hot melt using prepolymer of the present invention to prepare, has good bonding strength and package stability.
The technical scheme that the present invention solves the problems of the technologies described above is as follows:
Be that (hydroxyl value is 32 for the polyester glycol of 8:1:1 by mol ratio, the commercially available trade mark is POL-T3500), polyether glycol (hydroxyl value 56.1, the commercially available trade mark is PolyTHF-2000), polycaprolactone glycol (hydroxyl value 39, commercially available trade mark 220NPI) mixture and diphenylmethanediisocyanate (MDI-100 and MDI-50 mixture, MDI-50 weight ratio accounts for the 20-30% of gross weight) carry out polyreaction, the part by weight of diol mixture will and MDI mixture is 5-6:1.In reaction process, drip the two Zhong Ding aminodiphenylmethane chainextender (amine equivalent 155, commercially available trade mark WANALINK6200) of 4,4-, dripping quantity is the 1-2% of two kinds of amount of the mixture, the hot melt adhesive prepolymer that reaction generates, and NCO content controls as 2-4%.
Concrete synthetic technology condition is as follows:
The first step, by load weighted polyester glycol, (hydroxyl value is 32, the commercially available trade mark is POL-T3500), polyether glycol (hydroxyl value 56.1, the commercially available trade mark is PolyTHF-2000) first put into there-necked flask, after heating and melting, then add load weighted polycaprolactone glycol (hydroxyl value 39, commercially available trade mark 220NPI), by diol mixture will at 130 ± 5 DEG C after vacuum hydro-extraction 2 ~ 3h, cooling inflated with nitrogen is placed for subsequent use.
Second step, under nitrogen atmosphere, repeatedly joins load weighted MDI-100 and MID-50 in the there-necked flask of step 1) in batches, after adding, controls temperature of reaction 130 ± 5 DEG C, reaction 3h.
3rd step, less than 120 DEG C are cooled to after second step completes, start to drip in advance with 4,4-two Zhong Ding aminodiphenylmethane (amine equivalent 155, commercially available trade mark WANALINK6200) of molecular sieve process with dropping funnel, it is per second that rate of addition is that 1-2 drips, after being added dropwise to complete, controlling temperature of reaction is 130 ± 5 DEG C, continues reaction 2h, after having reacted, obtain Reactive hot melt adhesive prepolymer.
Embodiment
Embodiment 1
Weigh 280 grams of POL-T3500,20 grams of PolyTHF-2000 put into there-necked flask, setting Heating temperature is 128 DEG C, and heating and melting under nitrogen atmosphere, after material melting, add load weighted 20 grams of 220NPI, after being warming up to 128 DEG C, starting timing and vacuumize dehydration 3h, after the time, be cooled to 80 DEG C, under nitrogen atmosphere, gradation adds the MDI-100 52.6 grams, the MDI-50 13.2 grams that measure, after adding, control temperature of reaction 128 DEG C, clock reaction 3h.80 DEG C are cooled to after the time, start to drip the WANALINK6200 4.0 grams that ready molecular sieve removed water, rate of addition be 2 per second, after being added dropwise to complete, controlling temperature of reaction is 130 DEG C, continues reaction 2 hours, after the time, be cooled to 100 DEG C of dischargings, obtain Reactive hot melt adhesive prepolymer, NCO content is 3.7%.
Embodiment 2
Weigh 280 grams of POL-T3500,20 grams of PolyTHF-2000 put into there-necked flask, set Heating temperature as at 128 DEG C, heating and melting under nitrogen atmosphere, after material melting, add load weighted 20 grams of 220NPI, after being warming up to 128 DEG C, starting timing and vacuumize dehydration 3h, after the time, be cooled to 80 DEG C, under nitrogen atmosphere, gradation adds the MDI-100 49.3 grams, the MDI-50 16.5 grams that measure, after adding, control temperature of reaction 128 DEG C, clock reaction 3h.80 DEG C are cooled to after the time, start to drip the WANALINK6200 6.0 grams that ready molecular sieve removed water, rate of addition be 2 per second, after being added dropwise to complete, controlling temperature of reaction is 128 DEG C, continues reaction 2 hours, after the time, be cooled to 100 DEG C of dischargings, obtain Reactive hot melt adhesive prepolymer, NCO content is 3.1%.
Embodiment 3
Weigh 280 grams of POL-T3500,20 grams of PolyTHF-2000 put into there-necked flask, set Heating temperature as at 128 DEG C, heating and melting under nitrogen atmosphere, after material melting, add load weighted 20 grams of 220NPI, after being warming up to 128 DEG C, starting timing and vacuumize dehydration 3h, after the time, be cooled to 80 DEG C, under nitrogen atmosphere, gradation adds the MDI-100 38.4 grams, the MDI-50 16.4 grams that measure, after adding, control temperature of reaction 130 DEG C, clock reaction 3h.80 DEG C are cooled to after the time, start to drip the WANALINK6200 7.5 grams that ready molecular sieve removed water, rate of addition be 2 per second, after being added dropwise to complete, controlling temperature of reaction is 125 DEG C, continues reaction 2 hours, after the time, be cooled to 100 DEG C of dischargings, obtain Reactive hot melt adhesive prepolymer, NCO content is 2.3%.
The Comparison study citing of prepolymer of the present invention in reaction type polyurethane hot-melt adhesive.
Get commercially available conventional polyether/polyester-MDI prepolymer (being numbered P205P in advance, without any modification), appropriate with prepolymer of the present invention, NCO content is 3.1%.Be mixed with tackiness agent by the part that cooks noodle respectively and do contrast test.
First: P205P prepolymer 400 grams, tackifying resin, filler, oxidation inhibitor, catalyzer are appropriate.
Second: prepolymer of the present invention 400 grams, tackifying resin, filler, oxidation inhibitor, catalyzer are appropriate.
The first and second two of preparation glue samples are made aluminium aluminium to shear sample and carry out two 85 hot and humid tests, test is according to GB GB-T7124-2008-1993, and test data is in table one.
table one
| Two 85 digestion time h | Residue shearing resistance MPa | |
| First glue (commercially available conventional prepolymer) | 1000 | 2.5 |
| First glue (commercially available conventional prepolymer) | 0 | 10.64 |
| Second glue (modified prepolymers of the present invention) | 1000 | 9.82 |
| Second glue (modified prepolymers of the present invention) | 0 | 10.64 |
From table viewed from data, employ commercially available conventional prepolymer in first glue formula, after have passed through two 85 weathering tests, shearing resistance declines by a big margin, and residue shearing resistance fall is very large.And in second glue formula, employ prepolymer of the present invention, after two 85 anti-aging tests of 1000 hours, performance has almost no change, and embodies good adhesiveproperties and package stability.
Claims (7)
1. a synthetic method for reaction type polyurethane hot-melt adhesive prepolymer, is characterized in that, comprises following steps:
1) load weighted polyester glycol, polyether glycol are put into there-necked flask, after heating and melting, then add load weighted polycaprolactone glycol, by diol mixture will at 130 ± 5 DEG C after vacuum hydro-extraction 2 ~ 3h, cooling inflated with nitrogen is placed for subsequent use;
2) under nitrogen atmosphere, load weighted MDI-100 and MID-50 is repeatedly joined in the there-necked flask of step 1) in batches, after adding, control temperature of reaction 130 ± 5 DEG C, reaction 3h;
3) second step is cooled to less than 120 DEG C after completing, start to drip in advance with 4 of molecular sieve process with dropping funnel, the two Zhong Ding aminodiphenylmethane of 4-, it is per second that rate of addition is that 1-2 drips, after being added dropwise to complete, controlling temperature of reaction is 130 ± 5 DEG C, continues reaction 2h, after having reacted, obtain Reactive hot melt adhesive prepolymer;
The mol ratio of described polyester glycol, polyether glycol and polycaprolactone glycol is 8:1:1.
2. the synthetic method of a kind of reaction type polyurethane hot-melt adhesive prepolymer according to claim 1, is characterized in that, step 2) MDI-100 and MDI-50 mixture, MDI-50 weight ratio accounts for the 20-30% of gross weight.
3. the synthetic method of a kind of reaction type polyurethane hot-melt adhesive prepolymer according to claim 1, is characterized in that, step 1) diol mixture will and step 2) part by weight of MDI mixture is 5-6:1.
4. the synthetic method of a kind of reaction type polyurethane hot-melt adhesive prepolymer according to claim 1, is characterized in that, the dripping quantity of the two Zhong Ding aminodiphenylmethane of step 3) 4,4-is step 2) 1-2% of amount of the mixture.
5. the synthetic method of a kind of reaction type polyurethane hot-melt adhesive prepolymer according to claim 1, it is characterized in that, comprise: weigh 280 grams of POL-T3500, 20 grams of PolyTHF-2000 put into there-necked flask, setting Heating temperature is 128 DEG C, heating and melting under nitrogen atmosphere, after material melting, add load weighted 20 grams of 220NPI, after being warming up to 128 DEG C, start timing and vacuumize dehydration 3h, 80 DEG C are cooled to after the time, under nitrogen atmosphere, gradation adds the MDI-100 52.6 grams measured, MDI-50 13.2 grams, after adding, control temperature of reaction 128 DEG C, clock reaction 3h, 80 DEG C are cooled to after the time, start to drip the WANALINK6200 4.0 grams that ready molecular sieve removed water, rate of addition be 2 per second, after being added dropwise to complete, controlling temperature of reaction is 130 DEG C, continues reaction 2 hours, after the time, be cooled to 100 DEG C of dischargings, obtain Reactive hot melt adhesive prepolymer, NCO content is 3.7%.
6. the synthetic method of a kind of reaction type polyurethane hot-melt adhesive prepolymer according to claim 1, it is characterized in that, comprise: weigh 280 grams of POL-T3500, 20 grams of PolyTHF-2000 put into there-necked flask, set Heating temperature as at 128 DEG C, heating and melting under nitrogen atmosphere, after material melting, add load weighted 20 grams of 220NPI, after being warming up to 128 DEG C, start timing and vacuumize dehydration 3h, 80 DEG C are cooled to after the time, under nitrogen atmosphere, gradation adds the MDI-100 49.3 grams measured, MDI-50 16.5 grams, after adding, control temperature of reaction 128 DEG C, clock reaction 3h, 80 DEG C are cooled to after the time, start to drip the WANALINK6200 6.0 grams that ready molecular sieve removed water, rate of addition be 2 per second, after being added dropwise to complete, controlling temperature of reaction is 128 DEG C, continues reaction 2 hours, after the time, be cooled to 100 DEG C of dischargings, obtain Reactive hot melt adhesive prepolymer, NCO content is 3.1%.
7. the synthetic method of a kind of reaction type polyurethane hot-melt adhesive prepolymer according to claim 1, it is characterized in that, comprise: weigh 280 grams of POL-T3500, 20 grams of PolyTHF-2000 put into there-necked flask, set Heating temperature as at 128 DEG C, heating and melting under nitrogen atmosphere, after material melting, add load weighted 20 grams of 220NPI, after being warming up to 128 DEG C, start timing and vacuumize dehydration 3h, 80 DEG C are cooled to after the time, under nitrogen atmosphere, gradation adds the MDI-100 38.4 grams measured, MDI-50 16.4 grams, after adding, control temperature of reaction 130 DEG C, clock reaction 3h, 80 DEG C are cooled to after the time, start to drip the WANALINK6200 7.5 grams that ready molecular sieve removed water, rate of addition be 2 per second, after being added dropwise to complete, controlling temperature of reaction is 125 DEG C, continues reaction 2 hours, after the time, be cooled to 100 DEG C of dischargings, obtain Reactive hot melt adhesive prepolymer, NCO content is 2.3%.
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Cited By (5)
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| CN111704708A (en) * | 2020-06-08 | 2020-09-25 | 广州市乐基智能科技有限公司 | Preparation method of cross-linked polyurethane binder and application of cross-linked polyurethane binder in field of lithium batteries |
| CN111820513A (en) * | 2020-07-29 | 2020-10-27 | 韩韶利 | Pressure reducing shoulder belt |
| CN112375528A (en) * | 2020-11-11 | 2021-02-19 | 广州聚合新材料科技股份有限公司 | Reactive polyurethane hot melt adhesive, preparation method and application |
| CN115386326A (en) * | 2022-10-28 | 2022-11-25 | 广州鹿山新材料股份有限公司 | Single-component self-catalytic polyurethane hot melt adhesive and preparation method thereof |
| CN115572570A (en) * | 2021-12-23 | 2023-01-06 | 山西天启通液压有限公司 | Rubber protective coating film and preparation method thereof |
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| CN104610902A (en) * | 2015-02-12 | 2015-05-13 | 厦门誉匠复合材料有限公司 | Rapidly post-cured polyurethane hot melt adhesive and preparation method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111704708A (en) * | 2020-06-08 | 2020-09-25 | 广州市乐基智能科技有限公司 | Preparation method of cross-linked polyurethane binder and application of cross-linked polyurethane binder in field of lithium batteries |
| CN111820513A (en) * | 2020-07-29 | 2020-10-27 | 韩韶利 | Pressure reducing shoulder belt |
| CN112375528A (en) * | 2020-11-11 | 2021-02-19 | 广州聚合新材料科技股份有限公司 | Reactive polyurethane hot melt adhesive, preparation method and application |
| CN115572570A (en) * | 2021-12-23 | 2023-01-06 | 山西天启通液压有限公司 | Rubber protective coating film and preparation method thereof |
| CN115572570B (en) * | 2021-12-23 | 2024-02-20 | 山西天启通液压有限公司 | Rubber protection coating film and preparation method thereof |
| CN115386326A (en) * | 2022-10-28 | 2022-11-25 | 广州鹿山新材料股份有限公司 | Single-component self-catalytic polyurethane hot melt adhesive and preparation method thereof |
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Application publication date: 20151104 |