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CN114015405B - High-performance polyurethane pressure-sensitive adhesive and preparation method and application thereof - Google Patents

High-performance polyurethane pressure-sensitive adhesive and preparation method and application thereof Download PDF

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Publication number
CN114015405B
CN114015405B CN202111483032.8A CN202111483032A CN114015405B CN 114015405 B CN114015405 B CN 114015405B CN 202111483032 A CN202111483032 A CN 202111483032A CN 114015405 B CN114015405 B CN 114015405B
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parts
sensitive adhesive
polyurethane pressure
diisocyanate
performance polyurethane
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CN114015405A (en
Inventor
李俊彬
李莹
武鹏
刘鎏
李二威
尹鹏
罗国旗
程晨
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Hubei Aerospace Chemical New Materials Technology Co ltd
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Xiangyang Sunvaior Aerospace Films Co ltd
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Publication of CN114015405A publication Critical patent/CN114015405A/en
Priority to PCT/CN2022/116014 priority patent/WO2023103480A1/en
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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
    • 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
    • C08G18/3228—Polyamines acyclic
    • 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
    • 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
    • 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
    • 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
    • C09J11/08—Macromolecular additives
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • 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
    • C09J2467/00—Presence of polyester
    • C09J2467/006—Presence of polyester in the substrate
    • 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
    • C09J2475/00—Presence of polyurethane

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

The invention provides a high-performance polyurethane pressure-sensitive adhesive, which comprises the following components in parts by weight: 30-50 parts of polyether polyol, 4-10 parts of isocyanate, 0.05-0.2 part of catalyst, 0.4-2 parts of chain extender, 100-150 parts of solvent, 0.5-3 parts of antioxidant, 5-12 parts of organosilicon heat-resistant monomer, 1-3 parts of plasticizer and 0.5-2 parts of curing agent. The polyurethane pressure-sensitive adhesive disclosed by the invention has good wettability on an adhered object, the stripping force is still stable and does not increase even under high-temperature and/or high-humidity conditions, the pollution resistance is strong, and the use requirement in a high-temperature scene can be met.

Description

High-performance polyurethane pressure-sensitive adhesive and preparation method and application thereof
Technical Field
The invention relates to the technical field of pressure-sensitive adhesives, in particular to a high-performance polyurethane pressure-sensitive adhesive and a preparation method and application thereof.
Background
The pressure-sensitive adhesive is widely used for summarizing the preparation and manufacturing processes of office, packaging, electric appliances, automobiles, liquid crystal panels and mobile phone components. In the use scenes of electronics, automobiles and the like, the pressure-sensitive adhesive must have excellent cohesive force and adhesive force, and not only needs to ensure that no adhesive residue and no pollution exist when the protected surface is peeled off, but also needs to ensure easy peeling. Especially under high temperature use scenes such as die cutting, the performance requirement on the protective film is higher.
At present, the pressure-sensitive adhesive mainly takes a solvent type acrylate pressure-sensitive adhesive as a main material, has poor wetting effect on an adhered object, is unstable in stripping force under a high-temperature or high-humidity condition, is easy to remain adhesive, and cannot adapt to a high-temperature and high-humidity environment, so that the high-performance polyurethane pressure-sensitive adhesive which has a good wetting effect and can adapt to the high-temperature and high-humidity environment needs to be developed.
Disclosure of Invention
In view of the above, the invention provides a high-performance polyurethane pressure-sensitive adhesive which has a good wetting effect, is easy to peel, has no residual adhesive pollution, and can adapt to a high-temperature and high-humidity environment, and a preparation method thereof.
The technical scheme of the invention is realized as follows: on one hand, the invention provides a high-performance polyurethane pressure-sensitive adhesive, which is characterized in that: the composition comprises the following components in parts by weight: 30-50 parts of polyether polyol, 4-10 parts of isocyanate, 0.05-0.2 part of catalyst, 0.4-2 parts of chain extender, 100-150 parts of solvent, 0.5-3 parts of antioxidant, 5-12 parts of organosilicon heat-resistant monomer, 1-3 parts of plasticizer and 0.5-2 parts of curing agent; the plasticizer is one or a combination of more of castor oil and derivatives thereof.
On the basis of the above technical scheme, preferably, the plasticizer is one or a combination of more of dehydrated castor oil, hydrogenated castor oil, castor oil fatty acid and castor oil fatty acid ester.
On the basis of the technical scheme, preferably, the polyether polyol is one or a combination of more of polytetrahydrofuran ether glycol, polypropylene glycol, polyoxypropylene triol, glycerol polyether and ethylenediamine polyether tetrol; the isocyanate is one or more of toluene diisocyanate, diphenylmethane-4, 4' -diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, hexamethylene diisocyanate, lysine diisocyanate, isophorone diisocyanate and methyl cyclohexane diisocyanate.
Based on the above technical solution, preferably, the catalyst is a tin-based catalyst, and is selected from one or more of dioctyl tin oxide, dibutyl tin dichloride, dibutyl tin dibromide, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin sulfide, tributyl tin trichloroacetate, tributyl tin sulfide and dibutyl tin dimaleate.
On the basis of the technical scheme, preferably, the chain extender is a diamine chain extender and is selected from one or more of ethylenediamine, 1, 2-propylenediamine, 1, 6-hexamethylenediamine, isophorone diamine, 1, 4-cyclohexanediamine, N-hydroxymethyl aminoethylamine and N-ethylaminoethylamine.
On the basis of the technical scheme, preferably, the antioxidant is an antioxidant 1076; the solvent is one or a combination of more of toluene, butyl acetate, acetone, cyclohexanone, propylene glycol monoethyl ether and ethylene glycol mono-n-propyl ether.
On the basis of the above technical solutions, preferably, the silicone heat-resistant monomer is one or a combination of more of polydimethylsiloxane, cyclomethicone, aminosiloxane, polymethylphenylsiloxane and polyether polysiloxane copolymer.
Based on the above technical solution, preferably, the curing agent is one or more of toluene diisocyanate-trimethylolpropane adduct, chlorobenzene diisocyanate-trimethylolpropane adduct, hexamethylene diisocyanate-trimethylolpropane adduct, isophorone diisocyanate-trimethylolpropane adduct, isocyanurate, and biuret.
On the other hand, the invention provides a preparation method of high-performance polyurethane pressure-sensitive adhesive, which is characterized by comprising the following steps: the method comprises the following steps:
s1, sequentially adding 70-80% of polyether polyol, isocyanate and solvent in parts by weight into a reaction kettle, uniformly stirring, and adding N 2 Heating to 35-55 ℃ under protection, then slowly dripping a catalyst into the reaction solution, heating to 70-90 ℃ while stirring, and keeping the temperature of 70-90 ℃ for reaction for 3-6h after dripping is finished to obtain a mixed solution A;
s2, reducing the temperature of the mixed solution A to 40-60 ℃, then sequentially adding 20-30% of the chain extender, the plasticizer and the solvent in parts by weight, and carrying out heat preservation reaction at 40-60 ℃ for 1-3h to obtain a mixed solution B;
and S3, under the condition of continuously stirring at 40-60 ℃, sequentially dropwise adding the heat-resistant monomer, the antioxidant and the curing agent into the mixed solution B, stirring for 10-30min after dropwise adding is finished, and then cooling the reaction liquid to 20-30 ℃ to obtain the polyurethane pressure-sensitive adhesive.
Finally, the invention also provides an application of the high-performance polyurethane pressure-sensitive adhesive in the PET protective film, and the specific method comprises the following steps: uniformly coating polyurethane pressure-sensitive adhesive on a corona surface of a PET base film with the thickness of 50-60 mu m, placing the PET base film in an oven with the temperature of 80-100 ℃ for drying for 5-10min until the adhesive surface is dried, controlling the thickness of the dried adhesive to be 10 +/-1 mu m, then coating a release film with the thickness of 50 mu m on the adhesive surface, and placing the adhesive surface in the oven with the temperature of 40-50 ℃ for curing for 5d for later use.
Compared with the prior art, the high-performance polyurethane pressure-sensitive adhesive and the preparation method and application thereof have the following beneficial effects:
(1) According to the invention, a special plasticizer is introduced in the preparation process of the polyurethane pressure-sensitive adhesive, so that the polyurethane pressure-sensitive adhesive has excellent wettability (lower than 10 s) and stain resistance under the synergistic effect of the organic silicon heat-resistant monomer, the heat-resistant antioxidant and the plasticizer, and meanwhile, the prepared pressure-sensitive adhesive has stable peeling force and excellent heat resistance (the glass plate is free of pollution at 180 ℃ for 2 h), and can be stably and widely applied to high-end fields such as mobile phones, automobiles, panel manufacturing and the like.
(2) The proper chain extender is introduced in the preparation process of the polyurethane pressure-sensitive adhesive, so that the relative molecular mass of the polyurethane glue can be effectively improved, the cohesion and initial adhesion of the pressure-sensitive adhesive are improved, the occurrence of residual adhesive is effectively prevented, and the pollution resistance of the pressure-sensitive adhesive is improved.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments of the present invention, belong to the protection scope of the present invention.
Example 1
A high-performance polyurethane pressure-sensitive adhesive comprises the following components in parts by weight: polyether polyol: 10 parts of polytetrahydrofuran ether glycol and 20 parts of polypropylene glycol; isocyanate: 1 part of toluene diisocyanate and 3 parts of diphenylmethane-4, 4' -diisocyanate; catalyst: 0.02 part of dioctyltin oxide and 0.03 part of dibutyltin dichloride; chain extender: 0.2 part of ethylenediamine and 0.2 part of 1, 2-propanediamine; solvent: 40 parts of toluene and 60 parts of butyl acetate; antioxidant: 10760.5 parts of an antioxidant; organosilicon heat-resistant monomer: 2 parts of polydimethylsiloxane and 3 parts of cyclomethicone; plasticizer: 0.5 part of dehydrated castor oil and 0.5 part of hydrogenated castor oil; curing agent: 0.2 part of toluene diisocyanate-trimethylolpropane adduct and 0.3 part of chlorobenzene diisocyanate-trimethylolpropane adduct.
A preparation method of high-performance polyurethane pressure-sensitive adhesive comprises the following steps:
s1, sequentially adding 70 weight parts of polyether polyol, isocyanate and solvent into a reaction kettle, uniformly stirring, and adding N 2 Heating to 35 ℃ under protection, then slowly dropwise adding a catalyst into the reaction solution, heating to 70 ℃ while stirring, and after dropwise adding, keeping the temperature of 70 ℃ for reaction for 3 hours to obtain a mixed solution A;
s2, reducing the temperature of the mixed solution A to 40 ℃, then sequentially adding 30 weight parts of a chain extender, a plasticizer and a solvent, and carrying out heat preservation reaction for 1h at 40 ℃ to obtain a mixed solution B;
and S3, under the condition of continuously stirring at 40 ℃, sequentially dropwise adding the heat-resistant monomer, the antioxidant and the curing agent into the mixed solution B, stirring for 10min after dropwise adding is finished, and then cooling the reaction liquid to 20 ℃ to obtain the polyurethane pressure-sensitive adhesive.
The application of the high-performance polyurethane pressure-sensitive adhesive in the PET protective film comprises the steps of uniformly coating the polyurethane pressure-sensitive adhesive on a corona surface of a PET base film with the thickness of 50 microns, placing the PET base film in an oven with the temperature of 80 ℃ for drying for 5min until the adhesive surface is dried, controlling the thickness of the dry adhesive to be 9 microns, then coating a release film with the thickness of 50 microns on the adhesive surface, and placing the adhesive surface in the oven with the temperature of 40 ℃ for curing for 5d for later use.
Example 2
A high-performance polyurethane pressure-sensitive adhesive comprises the following components in parts by weight: 30 parts of polyoxypropylene triol and 20 parts of glycerol polyether; isocyanate: 2 parts of xylylene diisocyanate, 3 parts of tetramethyl xylylene diisocyanate and 5 parts of hexamethylene diisocyanate; catalyst: 0.5 part of dibutyl tin dibromide, 0.6 part of dibutyl tin dilaurate and 0.9 part of dibutyl tin diacetate; chain extender: 1 part of 1, 6-hexamethylene diamine and 1 part of isophorone diamine; solvent: 70 parts of acetone and 80 parts of cyclohexanone; antioxidant: 10763 parts of an antioxidant; organosilicon heat-resistant monomer: 5 parts of aminosiloxane and 7 parts of polymethylphenylsiloxane; plasticizer: 1 part of castor oil fatty acid and 2 parts of castor oil fatty acid ester; curing agent: 1 part of hexamethylene diisocyanate-trimethylolpropane adduct and 1 part of isophorone diisocyanate-trimethylolpropane adduct.
A preparation method of high-performance polyurethane pressure-sensitive adhesive comprises the following steps:
s1, sequentially adding 80 weight parts of polyether polyol, isocyanate and solvent into a reaction kettle, uniformly stirring, and adding N 2 Heating to 55 ℃ under protection, then slowly dropwise adding a catalyst into the reaction solution, heating to 90 ℃ while stirring, and after dropwise adding, keeping the temperature of 90 ℃ for reaction for 6 hours to obtain a mixed solution A;
s2, reducing the temperature of the mixed solution A to 60 ℃, then sequentially adding 20 weight parts of a chain extender, a plasticizer and a solvent, and carrying out heat preservation reaction for 3 hours at 60 ℃ to obtain a mixed solution B;
and S3, under the condition of continuously stirring at 60 ℃, dropwise adding the heat-resistant monomer, the antioxidant and the curing agent into the mixed solution B in sequence, stirring for 30min after dropwise adding, and then cooling the reaction solution to 30 ℃ to obtain the polyurethane pressure-sensitive adhesive.
The application of the high-performance polyurethane pressure-sensitive adhesive in the PET protective film comprises the steps of uniformly coating the polyurethane pressure-sensitive adhesive on a corona surface of a 60-micron-thick PET base film, placing the PET base film in a 100-DEG C drying oven for drying for 10min until the adhesive surface is dried, controlling the thickness of the dried adhesive to be 11 microns, then coating a release film with the thickness of 50 microns on the adhesive surface, and placing the adhesive surface in a 50-DEG C drying oven for curing for 5d for later use.
Example 3
A high-performance polyurethane pressure-sensitive adhesive comprises the following components in parts by weight: polyether polyol: 10 parts of glycerol polyether and 25 parts of ethylenediamine polyether tetrol; isocyanate: 1 part of lysine diisocyanate, 2 parts of isophorone diisocyanate and 2 parts of methylcyclohexane diisocyanate; catalyst: 0.3 part of dibutyl tin sulfide, 0.3 part of tributyl tin trichloroacetate and 0.3 part of tributyl tin sulfide; chain extender: 0.2 part of 1, 4-cyclohexanediamine, 0.3 part of N-hydroxymethyl aminoethylamine and 0.2 part of N-ethyl aminoethylamine; solvent: 60 parts of propylene glycol monoethyl ether and 50 parts of ethylene glycol mono-n-propyl ether; antioxidant: 10761 parts of an antioxidant; organosilicon heat-resistant monomer: 3 parts of polymethylphenylsiloxane and 4 parts of polyether polysiloxane copolymer; plasticizer: 1 part of dehydrated castor oil and 1 part of castor oil fatty acid ester; curing agent: isocyanurate 0.5 part and biuret 0.3 part;
a preparation method of high-performance polyurethane pressure-sensitive adhesive comprises the following steps:
s1, adding 72 weight parts of polyether polyol, isocyanate and solvent into a reaction kettle in sequence, stirring uniformly, and adding N 2 Heating to 38 ℃ under protection, then slowly dropwise adding a catalyst into the reaction solution, heating to 75 ℃ while stirring, and after dropwise adding, keeping the temperature at 75 ℃ for reaction for 4 hours to obtain a mixed solution A;
s2, cooling the temperature of the mixed solution A to 45 ℃, then sequentially adding a chain extender, a plasticizer and 28 weight parts of a solvent, and carrying out heat preservation reaction at 45 ℃ for 1.5 hours to obtain a mixed solution B;
and S3, under the condition of continuously stirring at 45 ℃, dropwise adding the heat-resistant monomer, the antioxidant and the curing agent into the mixed solution B in sequence, stirring for 15min after dropwise adding, and then cooling the reaction solution to 25 ℃ to obtain the polyurethane pressure-sensitive adhesive.
The application of the high-performance polyurethane pressure-sensitive adhesive in the PET protective film comprises the steps of uniformly coating the polyurethane pressure-sensitive adhesive on a corona surface of a PET base film with the thickness of 55 microns, placing the PET base film in an oven with the temperature of 85 ℃ for drying for 6min until the adhesive surface is dried, controlling the thickness of the dry adhesive to be 10 microns, then coating a release film with the thickness of 50 microns on the adhesive surface, and placing the adhesive surface in the oven with the temperature of 45 ℃ for curing for 5d for later use.
Example 4
A high-performance polyurethane pressure-sensitive adhesive comprises the following components in parts by weight: polyether polyol: 15 parts of polytetrahydrofuran ether glycol, 15 parts of glycerol polyether and 15 parts of ethylenediamine polyether tetrol; isocyanate: 2 parts of diphenylmethane-4, 4' -diisocyanate, 2 parts of tetramethylxylylene diisocyanate and 2 parts of lysine diisocyanate; catalyst: 0.04 part of dioctyl tin oxide, 0.04 part of tributyl tin trichloroacetate and 0.04 part of dibutyl tin dimaleate; chain extender: 0.3 part of 1, 6-hexamethylene diamine, 0.3 part of isophorone diamine and 0.4 part of N-ethylaminoethylamine; solvent: 50 parts of toluene and 70 parts of acetone; antioxidant: 10761.5 parts of an antioxidant; organosilicon heat-resistant monomer: 2 parts of polydimethylsiloxane, 3 parts of aminosiloxane and 3 parts of polymethylphenylsiloxane; plasticizer: 0.7 part of dehydrated castor oil and 0.8 part of castor oil fatty acid ester; curing agent: 0.5 part of toluene diisocyanate-trimethylolpropane adduct and 0.5 part of isophorone diisocyanate-trimethylolpropane adduct.
A preparation method of high-performance polyurethane pressure-sensitive adhesive comprises the following steps:
s1, adding 75 weight parts of polyether polyol, isocyanate and solvent into a reaction kettle in sequence, uniformly stirring, and adding N 2 Heating to 45 ℃ under protection, then slowly dropwise adding a catalyst into the reaction solution, heating to 80 ℃ while stirring, and after dropwise adding, keeping the temperature of 80 ℃ for reaction for 4 hours to obtain a mixed solution A;
s2, cooling the temperature of the mixed solution A to 45 ℃, then sequentially adding 25% of the chain extender, the plasticizer and the solvent in parts by weight, and carrying out heat preservation reaction for 1.5 hours at 45 ℃ to obtain a mixed solution B;
and S3, under the condition of continuously stirring at 45 ℃, dropwise adding the heat-resistant monomer, the antioxidant and the curing agent into the mixed solution B in sequence, stirring for 25min after dropwise adding, and then cooling the reaction solution to 25 ℃ to obtain the polyurethane pressure-sensitive adhesive.
The application of the high-performance polyurethane pressure-sensitive adhesive in the PET protective film comprises the steps of uniformly coating the polyurethane pressure-sensitive adhesive on a corona surface of a PET base film with the thickness of 50 microns, placing the PET base film in a 95 ℃ oven to be dried for 8min until the adhesive surface is dried, controlling the thickness of the dry adhesive to be 10 microns, then coating a release film with the thickness of 50 microns on the adhesive surface, and placing the adhesive surface in a 45 ℃ oven to be cured for 5d for later use.
Example 5
A high-performance polyurethane pressure-sensitive adhesive comprises the following components in parts by weight: polyether polyol: 10 parts of polytetrahydrofuran ether glycol, 10 parts of polypropylene glycol and 20 parts of ethylenediamine polyether tetrol; isocyanate: 2 parts of diphenylmethane-4, 4' -diisocyanate, 2 parts of isophorone diisocyanate and 3 parts of methylcyclohexane diisocyanate; catalyst: 0.05 part of dibutyl tin dibromide, 0.05 part of dibutyl tin sulfide and 0.05 part of tributyl tin trichloroacetate; chain extender: 0.5 part of isophorone diamine, 0.5 part of 1, 4-cyclohexane diamine and 0.5 part of N-ethylaminoethylamine; solvent: 60 parts of butyl acetate and 70 parts of cyclohexanone; antioxidant: 10762 parts of an antioxidant; organosilicon heat-resistant monomer: 3 parts of cyclomethicone, 3 parts of polymethylphenylsiloxane and 3 parts of polyether polysiloxane copolymer; plasticizer: 1 part of hydrogenated castor oil and 1.5 parts of castor oil fatty acid ester; curing agent: 0.5 part of toluene diisocyanate-trimethylolpropane adduct, 0.5 part of isophorone diisocyanate-trimethylolpropane adduct and 0.5 part of biuret.
A preparation method of high-performance polyurethane pressure-sensitive adhesive comprises the following steps:
s1, adding 74 weight parts of polyether polyol, isocyanate and solvent into a reaction kettle in sequence, stirring uniformly, and adding N 2 Heating to 40 ℃ under protection, then slowly dropwise adding a catalyst into the reaction solution, heating to 80 ℃ while stirring, and after dropwise adding, keeping the temperature of 80 ℃ for reaction for 5 hours to obtain a mixed solution A;
s2, reducing the temperature of the mixed solution A to 55 ℃, then sequentially adding 26 weight parts of a chain extender, a plasticizer and a solvent, and carrying out heat preservation reaction for 2.5 hours at 55 ℃ to obtain a mixed solution B;
and S3, under the condition of continuously stirring at 60 ℃, dropwise adding the heat-resistant monomer, the antioxidant and the curing agent into the mixed solution B in sequence, stirring for 20min after dropwise adding, and then cooling the reaction solution to 25 ℃ to obtain the polyurethane pressure-sensitive adhesive.
The application of the high-performance polyurethane pressure-sensitive adhesive in the PET protective film comprises the steps of uniformly coating the polyurethane pressure-sensitive adhesive on a corona surface of a 60-micron-thick PET base film, placing the PET base film in a 100-DEG C drying oven for drying for 5min until the adhesive surface is dried, controlling the thickness of the dried adhesive to be 11 microns, then coating a release film with the thickness of 50 microns on the adhesive surface, and placing the adhesive surface in a 50-DEG C drying oven for curing for 5d for later use.
Example 6
A high-performance polyurethane pressure-sensitive adhesive comprises the following components in parts by weight: polyether polyol: 10 parts of polytetrahydrofuran ether glycol, 14 parts of polyoxypropylene triol and 14 parts of ethylenediamine polyether tetrol; isocyanate: 2 parts of toluene diisocyanate, 2 parts of xylylene diisocyanate, 2 parts of hexamethylene diisocyanate and 3 parts of lysine diisocyanate; catalyst: 0.03 part of dioctyl tin oxide, 0.04 part of tributyl tin trichloroacetate, 0.05 part of tributyl tin sulfide and 0.06 part of dibutyl tin dimaleate; chain extender: 0.6 part of 1, 2-propane diamine, 0.3 part of isophorone diamine, 0.5 part of 1, 4-cyclohexane diamine and 0.4 part of N-hydroxymethyl aminoethylamine; solvent: 60 parts of butyl acetate, 50 parts of acetone and 30 parts of propylene glycol monoethyl ether; antioxidant: 10762.5 parts of an antioxidant; organosilicon heat-resistant monomer: 2 parts of aminosiloxane, 3 parts of polymethylphenylsiloxane and 5 parts of polyether polysiloxane copolymer; plasticizer: 1 part of dehydrated castor oil, 1.4 parts of hydrogenated castor oil and 0.4 part of castor oil fatty acid; curing agent: 0.7 part of tolylene diisocyanate-trimethylolpropane adduct, 0.7 part of chlorobenzene diisocyanate-trimethylolpropane adduct, 0.7 part of isophorone diisocyanate-trimethylolpropane adduct and 0.7 part of isocyanurate.
A preparation method of high-performance polyurethane pressure-sensitive adhesive comprises the following steps:
s1, adding 73 weight parts of polyether polyol, isocyanate and solvent into a reaction kettle in sequence, uniformly stirring, and adding N 2 Heating to 50 ℃ under protection, then slowly dropwise adding a catalyst into the reaction solution, heating to 85 ℃ while stirring, and after dropwise adding, keeping the temperature of 85 ℃ for reaction for 5 hours to obtain a mixed solution A;
s2, reducing the temperature of the mixed solution A to 45 ℃, then sequentially adding 27 weight parts of a chain extender, a plasticizer and a solvent, and carrying out heat preservation reaction for 1.5h at 45 ℃ to obtain a mixed solution B;
and S3, under the condition of continuously stirring at 55 ℃, dropwise adding the heat-resistant monomer, the antioxidant and the curing agent into the mixed solution B in sequence, stirring for 25min after dropwise adding, and then cooling the reaction solution to 25 ℃ to obtain the polyurethane pressure-sensitive adhesive.
The application of the high-performance polyurethane pressure-sensitive adhesive in the PET protective film comprises the steps of uniformly coating the polyurethane pressure-sensitive adhesive on a corona surface of a PET base film with the thickness of 50 microns, placing the PET base film in an oven with the temperature of 85 ℃ for drying for 5min until the adhesive surface is dried, controlling the thickness of the dry adhesive to be 10 microns, then coating a release film with the thickness of 50 microns on the adhesive surface, and placing the release film in the oven with the temperature of 40 ℃ for curing for 5d for later use.
Comparative example 1
Example 1 lacking the plasticizer is comparative example 1, and the rest of the components are the same as example 1, and the preparation method and the application are also the same.
Comparative example 2
Example 1 lacking the silicone heat-resistant monomer is taken as comparative example 2, and the rest of the components are the same as example 1, and the preparation method and the application are also the same.
Comparative example 3
Example 1 lacking the chain extender is taken as comparative example 3, and the rest of the components are the same as example 1, and the preparation method and the application are also the same.
Comparative example 4
Example 1 lacking the plasticizer, the silicone heat-resistant monomer and the chain extender is taken as comparative example 4, and the rest of the components are the same as in example 1, and the preparation method and the application are also the same.
And (3) testing the performance of the polyurethane pressure-sensitive adhesive:
and (3) testing the peeling force: according to the test method of GB 2792-1998 standard, the protective film with the adhesive surface is pasted on an SU304 stainless steel plate and soaked for 30min under the test conditions of 23 +/-2 ℃ and 65 +/-5% of humidity, and the peeling force of the stainless steel plate in the direction of 180 ℃ is measured, wherein the unit is gf/25mm.
Peel force increase test: the peel force after cooling the oven to room temperature at 120 ℃ for 1h was also tested.
And (3) testing heat resistance: and respectively attaching the cut PET protective films with the width of 25mm to the steel plate and the glass, placing the steel plate and the glass in an oven for baking at 180 ℃ for 2 hours, cooling to room temperature, tearing off the steel plate and the glass plate, and then observing whether residual glue exists on the glass plate and the steel plate.
Wet heat resistance test on glass: attaching the prepared PET protective films to two surfaces of a clean glass cover plate, placing the glass cover plate in an environment with the temperature of 85 ℃ and the humidity of 85% for 15d, and observing whether the surface of the glass has pollution (mottled shadow, residual glue and the like) when the PET protective films are torn off.
Wettability test on glass: cutting a 100mm multiplied by 100mm PET protective film, attaching the PET protective film on a glass cover plate, and recording the time for the protective film to completely wet and attach the glass cover plate until no bubbles exist. Evaluation criteria: excellent (< 10 s); good (10-20 s); poor (> 20 s).
Table 1 statistics of performance test results
Figure BDA0003396162890000121
As can be analyzed from the experimental data in Table 1, compared with the comparative example, the polyurethane pressure-sensitive adhesive of the invention has the advantages of good wettability, small increase of high-temperature peeling force, moisture and heat resistance, no residual adhesive and no mottle at 180 ℃ for 2 h. This indicates that: the special plasticizer, the organic silicon heat-resistant monomer and the heat-resistant antioxidant are introduced in the preparation process of the polyurethane pressure-sensitive adhesive, so that the polyurethane pressure-sensitive adhesive has excellent wettability and stain resistance, and the prepared pressure-sensitive adhesive has stable stripping force and excellent heat resistance; the proper chain extender is introduced, so that the relative molecular mass of polyurethane glue can be effectively improved, the cohesion and initial adhesion of the pressure-sensitive adhesive are improved, the occurrence of residual glue is effectively prevented, the pollution resistance of the pressure-sensitive adhesive is improved, and the polyurethane pressure-sensitive adhesive can be stably and widely applied to high-end fields such as mobile phone, automobile and panel manufacturing.
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 (9)

1. A high-performance polyurethane pressure-sensitive adhesive is characterized in that: the composition comprises the following components in parts by weight: 30-50 parts of polyether polyol, 4-10 parts of isocyanate, 0.05-0.2 part of catalyst, 0.4-2 parts of chain extender, 100-150 parts of solvent, 0.5-3 parts of antioxidant, 5-12 parts of organic silicon heat-resistant monomer, 1-3 parts of plasticizer and 0.5-2 parts of curing agent; the plasticizer is one or a combination of more of castor oil and derivatives thereof; the organic silicon heat-resistant monomer is one or a combination of polydimethylsiloxane, cyclomethicone, polymethylphenylsiloxane and polyether polysiloxane copolymer.
2. The high performance polyurethane pressure sensitive adhesive of claim 1, wherein: the plasticizer is one or more of dehydrated castor oil, hydrogenated castor oil, castor oil fatty acid and castor oil fatty acid ester.
3. The high-performance polyurethane pressure-sensitive adhesive according to claim 1, wherein: the polyether polyol is one or a combination of more of polytetrahydrofuran ether glycol, polypropylene glycol, polyoxypropylene triol, glycerol polyether and ethylenediamine polyether tetrol; the isocyanate is one or more of toluene diisocyanate, diphenylmethane-4, 4' -diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, hexamethylene diisocyanate, lysine diisocyanate, isophorone diisocyanate and methyl cyclohexane diisocyanate.
4. The high performance polyurethane pressure sensitive adhesive of claim 1, wherein: the catalyst is a tin catalyst, and is selected from one or more of dioctyl tin oxide, dibutyl tin dichloride, dibutyl tin dibromide, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin sulfide, tributyl tin trichloroacetate, tributyl tin sulfide and dibutyl tin dimaleate.
5. The high-performance polyurethane pressure-sensitive adhesive according to claim 1, wherein: the chain extender is a diamine chain extender and is selected from one or more of ethylenediamine, 1, 2-propanediamine, 1, 6-hexamethylenediamine, isophorone diamine, 1, 4-cyclohexanediamine, N-hydroxymethyl aminoethyl amine and N-ethyl aminoethyl amine.
6. The high performance polyurethane pressure sensitive adhesive of claim 1, wherein: the antioxidant is an antioxidant 1076; the solvent is one or a combination of more of toluene, butyl acetate, acetone, cyclohexanone, propylene glycol monoethyl ether and ethylene glycol mono-n-propyl ether.
7. The high performance polyurethane pressure sensitive adhesive of claim 1, wherein: the curing agent is one or more of toluene diisocyanate-trimethylolpropane adduct, chlorobenzene diisocyanate-trimethylolpropane adduct, hexamethylene diisocyanate-trimethylolpropane adduct, isophorone diisocyanate-trimethylolpropane adduct, isocyanurate and biuret.
8. A method for preparing a high-performance polyurethane pressure-sensitive adhesive as defined in any one of claims 1 to 7, wherein: the method comprises the following steps:
s1, sequentially adding 70-80% of polyether polyol, isocyanate and solvent in parts by weight into a reaction kettle, uniformly stirring, and adding N 2 Under protection, heating the reaction solution to 35-55 ℃, then slowly dripping a catalyst into the reaction solution, heating to 70-90 ℃ while stirring, and after dripping is finished, keeping the temperature of 70-90 ℃ for reaction for 3-6 hours to obtain a mixed solution A;
s2, reducing the temperature of the mixed solution A to 40-60 ℃, then sequentially adding 20-30% of the chain extender, the plasticizer and the solvent in parts by weight, and carrying out heat preservation reaction at 40-60 ℃ for 1-3h to obtain a mixed solution B;
and S3, under the condition of continuously stirring at 40-60 ℃, sequentially dropwise adding the heat-resistant monomer, the antioxidant and the curing agent into the mixed solution B, stirring for 10-30min after dropwise adding is finished, and then cooling the reaction liquid to 20-30 ℃ to obtain the polyurethane pressure-sensitive adhesive.
9. Use of a high performance polyurethane pressure sensitive adhesive according to any one of claims 1 to 7 in a PET protective film, wherein: uniformly coating polyurethane pressure-sensitive adhesive on a corona surface of a PET base film with the thickness of 50-60 mu m, placing the PET base film in an oven with the temperature of 80-100 ℃ for drying for 5-10min until the adhesive surface is dried, controlling the thickness of the dried adhesive to be 10 +/-1 mu m, then coating a release film with the thickness of 50 mu m on the adhesive surface, and placing the adhesive surface in the oven with the temperature of 40-50 ℃ for curing for 5d for later use.
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