CN109627414B - High-temperature post-curing polyurethane composite material - Google Patents
High-temperature post-curing polyurethane composite material Download PDFInfo
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- CN109627414B CN109627414B CN201811510390.1A CN201811510390A CN109627414B CN 109627414 B CN109627414 B CN 109627414B CN 201811510390 A CN201811510390 A CN 201811510390A CN 109627414 B CN109627414 B CN 109627414B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
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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
- C08G18/08—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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- 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
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
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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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
- C08K13/06—Pretreated ingredients and ingredients covered by the main groups C08K3/00 - C08K7/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/22—Expanded, porous or hollow particles
- C08K7/24—Expanded, porous or hollow particles inorganic
- C08K7/26—Silicon- containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
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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
- C09J11/04—Non-macromolecular additives inorganic
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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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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention provides a high-temperature post-curing polyurethane composite material, belonging to the technical field of polyurethane materials. The composite material comprises the following components in parts by weight: 40-60 parts of polyurethane prepolymer, 20-30 parts of modified diatomite, 4-8 parts of water-based polyisocyanate and 3-5 parts of auxiliary agent; the polyurethane prepolymer is obtained by reacting polyether polyol, diisocyanate, a chain extender and a catalyst; the modified diatomite is obtained by modifying the surface of diatomite with a mixture of isopropyl bis (acetoacetato) aluminate and gamma-methacryloxypropyltrimethoxysilane. According to the invention, through the matching of the polyurethane prepolymer, the modified diatomite and the water-based polyisocyanate, the surface of the obtained composition is free from bubbles, and the modified diatomite can modify the interface action between substances, so that the bonding performance of the polyurethane material is improved.
Description
Technical Field
The invention belongs to the technical field of polyurethane materials, and particularly relates to a high-temperature post-curing polyurethane composite material.
Background
Polyurethane materials are widely used in the fields of transportation, construction, machinery, electronic equipment, furniture, food processing, clothing, textile, synthetic leather, printing, mining, petrochemical, water conservancy, national defense, sports, leisure and entertainment, medical treatment and the like because of their excellent properties. The use of the most commercially available solvent polyurethanes is limited by the disadvantage of their high content of volatile solvents. The waterborne polyurethane takes nontoxic and pollution-free water as a dispersion medium, has the advantages of low toxicity, difficult combustion, low pollution, energy conservation, safety and the like, and simultaneously combines the characteristics of good mechanical property, strong adhesive force, good wear resistance and the like of the polyurethane coating with the advantage of low volatile solvent of the waterborne coating, thereby arousing the general attention of people.
The existing high-temperature post-curing polyurethane composition has certain influence on the bonding property due to the decomposition of small molecules, and in addition, the phenomenon of surface bubbling and softening after high-temperature curing can be caused due to volatilization of low boiling point and the like.
Disclosure of Invention
The invention aims to solve the problems that the surface of the existing polyurethane composition has bubbles after high-temperature curing and the bonding performance is poor, and provides a high-temperature post-curing polyurethane composition.
The invention provides a high-temperature post-curing polyurethane composite material which comprises the following components in parts by weight:
the polyurethane prepolymer is obtained by reacting polyether polyol, diisocyanate, a chain extender and a catalyst;
the modified diatomite is obtained by modifying the surface of diatomite with a mixture of isopropyl bis (acetoacetato) aluminate and gamma-methacryloxypropyltrimethoxysilane.
Preferably, the mass ratio of the isopropyl di (acetoacetate) aluminate to the gamma-methacryloxypropyltrimethoxysilane is 3: 7.
preferably, the preparation method of the modified diatomite comprises the following steps:
1) mixing isopropyl bis (acetoacetate ethyl) aluminate and gamma-methacryloxypropyl trimethoxysilane to obtain a mixture;
2) mixing diatomite and the above mixture at 60-65 deg.C under stirring for 40-60min to obtain modified diatomite.
Preferably, the mass ratio of the diatomite to the mixture is 15: 1.
preferably, the preparation method of the polyurethane prepolymer comprises the following steps:
the method comprises the following steps: reacting polyether polyol and diisocyanate to obtain a first prepolymer;
step two: reacting the first polymer with a chain extender to obtain a second prepolymer;
step three: and reacting the second prepolymer with a catalyst to obtain the polyurethane prepolymer.
Preferably, the mass ratio of the polyether polyol, the diisocyanate, the chain extender and the catalyst is (30-40): (10-20): (2-5): (1-3).
Preferably, the diisocyanate isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, diphenylmethane diisocyanate, 2, 4-toluene diisocyanate or dicyclohexylmethane diisocyanate is used.
Preferably, the chain extender is 2, 2-dimethylolpropionic acid or 2, 2-dimethylolbutyric acid.
Preferably, the water-based polyisocyanate is a commercial product of the type
3100、
XP 2487/1, or
XP 2451。
Preferably, the auxiliary agent comprises a stabilizer, a plasticizer or an antioxidant.
The invention has the advantages of
The invention provides a high-temperature post-curing polyurethane composite material which comprises the following components in parts by weight: 40-60 parts of polyurethane prepolymer, 20-30 parts of modified diatomite, 4-8 parts of water-based polyisocyanate and 3-5 parts of auxiliary agent; the polyurethane prepolymer is obtained by reacting polyether polyol, diisocyanate, a chain extender and a catalyst; the modified diatomite is obtained by modifying the surface of diatomite with a mixture of isopropyl bis (acetoacetato) aluminate and gamma-methacryloxypropyltrimethoxysilane. According to the invention, through the matching of the polyurethane prepolymer, the modified diatomite and the water-based polyisocyanate, the surface of the obtained composition is free from bubbles, and the modified diatomite can modify the interface action between substances, so that the bonding performance of the polyurethane material is improved.
Detailed Description
The invention provides a high-temperature post-curing polyurethane composite material which comprises the following components in parts by weight:
40-60 parts of polyurethane prepolymer, 20-30 parts of modified diatomite, 4-8 parts of water-based polyisocyanate and 3-5 parts of auxiliary agent,
the polyurethane prepolymer is obtained by reacting polyether polyol, diisocyanate, a chain extender and a catalyst;
the modified diatomite is obtained by modifying the surface of diatomite with a mixture of isopropyl bis (acetoacetato) aluminate and gamma-methacryloxypropyltrimethoxysilane.
According to the invention, the preparation method of the modified diatomite comprises the following steps:
1) mixing isopropyl bis (acetoacetate ethyl) aluminate and gamma-methacryloxypropyl trimethoxysilane to obtain a mixture; the mass ratio of the isopropyl di (acetoacetate) aluminate to the gamma-methacryloxypropyltrimethoxysilane is preferably 3: 7.
2) and stirring and mixing the kieselguhr and the mixture at the temperature of between 60 and 65 ℃ for 40 to 60 minutes to obtain modified kieselguhr, wherein the mass ratio of the kieselguhr to the mixture is preferably 15: 1.
according to the present invention, the method for preparing a polyurethane prepolymer comprises:
the method comprises the following steps: reacting polyether polyol and diisocyanate to obtain a first prepolymer;
step two: reacting the first polymer with a chain extender to obtain a second prepolymer;
step three: and reacting the second prepolymer with a catalyst to obtain the polyurethane prepolymer.
According to the invention, under the protection of nitrogen, polyether polyol and diisocyanate are added into a reaction device, the temperature is raised to 90-95 ℃, and after polymerization is carried out for 3-5 hours, a first prepolymer is obtained; the polyether polyol preferably has a number average molecular weight of 5000-.
According to the invention, a chain extender is added into the first prepolymer for reaction, the reaction temperature is preferably 70-90 ℃, and the reaction time is preferably 2-3 hours, so as to obtain a second prepolymer; the chain extender is preferably 2, 2-dimethylolpropionic acid or 2, 2-dimethylolbutyric acid.
According to the invention, a catalyst is added into the second prepolymer for reaction, the reaction temperature is preferably 70-90 ℃, and the reaction time is preferably 2-3 hours, so as to obtain a polyurethane prepolymer; the catalyst is preferably stannous octoate or dibutyltin dilaurate.
According to the invention, the mass ratio of the polyether polyol, the diisocyanate, the chain extender and the catalyst is (30-40): (10-20): (2-5): (1-3), more preferably 35: 15: 3: 2.
according to the invention, the aqueous polyisocyanates are preferably those of the commercial type
3100、
XP 2487/1, or
XP 2451。
According to the invention, the auxiliary agent comprises a stabilizer, a plasticizer or an antioxidant. The stabilizer, plasticizer and antioxidant are conventional auxiliaries well known in the art, without particular limitation,
the stabilizer is preferably UV-320; the stabilizer is preferably an antioxidant 1010; the plasticizer is preferably dodecyl benzene sulfonate.
The invention relates to a preparation method of a high-temperature post-curing polyurethane composite material, which comprises the following steps:
and (2) in a reaction vessel, firstly adding a polyurethane prepolymer, heating to 70-85 ℃, degassing for 5-10 minutes, then adding modified diatomite, stirring and mixing for 10-15 minutes in vacuum, then adding water-based polyisocyanate and an auxiliary agent, and mixing for 20-30 minutes in vacuum to obtain the high-temperature post-curing polyurethane composite material.
The present invention is further illustrated by reference to the following specific examples, in which the starting materials are all commercially available.
Example 1 preparation of polyurethane prepolymer
Under the protection of nitrogen, adding 35g of polytetrahydrofuran diol (with the number average molecular weight of 5000 daltons) and 15g of 2, 4-toluene diisocyanate into a reaction device, heating to 92 ℃, and polymerizing for 4 hours to obtain a first prepolymer;
adding 2, 2-dimethylolpropionic acid 3g into the first prepolymer, and reacting at 90 ℃ for 2.5 hours to obtain a second prepolymer;
2g of stannous octoate was added to the second prepolymer and reacted at 80 ℃ for 2.5 hours to obtain a polyurethane prepolymer.
Example 2 preparation of modified diatomaceous Earth
Mixing 0.3g of isopropyl bis (acetoacetoxyethyl) aluminate and 0.7g of gamma-methacryloxypropyltrimethoxysilane to obtain a mixture; 15g of diatomaceous earth and the above mixture were stirred and mixed at 65 ℃ for 50min to obtain modified diatomaceous earth.
Comparative example 1
15g of diatomaceous earth and 1g of isopropyl bis (acetoacetato) aluminate were stirred and mixed at 65 ℃ for 50 minutes to obtain modified diatomaceous earth.
Comparative example 2
15g of diatomaceous earth and 1g of gamma-methacryloxypropyltrimethoxysilane were stirred and mixed at 65 ℃ for 50 minutes to obtain modified diatomaceous earth.
Example 3 preparation of polyurethane composite
50g of the polyurethane prepolymer prepared in example 1 were initially charged in a reaction vessel, heated to 80 ℃ and degassed for 8 minutes, 25g of the modified kieselguhr prepared in example 2 were added and mixed under vacuum for 12 minutes, and 6g of the aqueous polyisocyanate were added
3100. And (3) mixing 1g of UV-320, 1g of antioxidant 1010 and 2g of phenyl dodecyl sulfonate in vacuum for 25 minutes to obtain the high-temperature post-curing polyurethane composite material.
Example 4 preparation of polyurethane composite
40g of the polyurethane prepolymer prepared in example 1 were initially charged in a reaction vessel, heated to 70 ℃ and degassed for 10 minutes, 20g of the modified kieselguhr prepared in example 2 were added and mixed under vacuum for 10 minutes, and 4g of the aqueous polyisocyanate were added
3100. And (3) mixing 1g of UV-320, 1g of antioxidant 1010 and 1g of phenyl dodecyl sulfonate in vacuum for 20 minutes to obtain the high-temperature post-curing polyurethane composite material.
Example 5 preparation of polyurethane composite
60g of the polyurethane prepolymer prepared in example 1 were initially charged in a reaction vessel, heated to 85 ℃ and degassed for 5 minutes, 30g of the modified kieselguhr prepared in example 2 were added and mixed under vacuum for 15 minutes, and 8g of the aqueous polyisocyanate were added
3100. And (3) mixing 1g of UV-320, 1g of antioxidant 1010 and 3g of phenyl dodecyl sulfonate in vacuum for 30 minutes to obtain the high-temperature post-curing polyurethane composite material.
Comparative example 3
50g of the polyurethane prepolymer prepared in example 1 were initially charged in a reaction vessel, heated to 80 ℃ and degassed for 8 minutes, 25g of diatomaceous earth were then added and mixed under vacuum for 12 minutes, and the mixture was stirred and mixed again6g of aqueous polyisocyanate were added
3100. And (3) mixing 1g of UV-320, 1g of antioxidant 1010 and 2g of phenyl dodecyl sulfonate in vacuum for 25 minutes to obtain the high-temperature post-curing polyurethane composite material.
Comparative example 4
50g of the polyurethane prepolymer prepared in example 1 were initially charged in a reaction vessel, heated to 80 ℃ and degassed for 8 minutes, 25g of the modified diatomaceous earth prepared in comparative example 1 were added and mixed under vacuum for 12 minutes, and 6g of the aqueous polyisocyanate were added
3100. And (3) mixing 1g of UV-320, 1g of antioxidant 1010 and 2g of phenyl dodecyl sulfonate in vacuum for 25 minutes to obtain the high-temperature post-curing polyurethane composite material.
Comparative example 5
50g of the polyurethane prepolymer prepared in example 1 were initially charged in a reaction vessel, heated to 80 ℃ and degassed for 8 minutes, 25g of the modified diatomaceous earth prepared in comparative example 2 were added and mixed under vacuum for 12 minutes, and 6g of the aqueous polyisocyanate were added
3100. And (3) mixing 1g of UV-320, 1g of antioxidant 1010 and 2g of phenyl dodecyl sulfonate in vacuum for 25 minutes to obtain the high-temperature post-curing polyurethane composite material.
The polyurethane composite materials obtained in examples 3-5 and comparative examples 3-5 were uniformly coated on a polytetrafluoroethylene plate, the thickness was 150-200 um, after drying at 70 ℃ for 5 hours, and after completely drying in a vacuum oven at 50 ℃ for 8 hours, the mechanical properties of the obtained coating films were tested, and the results are shown in table 1.
The polyurethane compositions obtained in examples 3 to 5 and comparative examples 3 to 5 were coated on flexible and rigid adhesive test pieces, respectively, and then dried in an oven at 80 ℃ to conduct adhesion property tests. The test results are shown in Table 1.
TABLE 1
| Item | Example 3 | Example 4 | Example 5 | Comparative example 3 | Comparative example 4 | Comparative example 5 |
| Hardness (Shao A) | 82 | 75 | 70 | 68 | 60 | 62 |
| Tensile strength (Mpa) | 14.5 | 12.7 | 13.2 | 7.5 | 8.3 | 8.6 |
| Elongation% | 380 | 320 | 340 | 210 | 228 | 242 |
| Whether or not there is air bubble after high temperature | Is free of | Is free of | Is free of | Many bubbles | Small amount of bubbles | Small amount of bubbles |
| Adhesive Strength/N | 25 | 23 | 22 | 8 | 10 | 9 |
As can be seen from the properties of Table 1, the polyurethane composite material of the present invention has good mechanical properties, no bubbles after high temperature, and improved adhesion properties.
Claims (6)
1. The high-temperature post-curing polyurethane composite material is characterized by comprising the following components in parts by weight:
40-60 parts of polyurethane prepolymer
20-30 parts of modified diatomite
4-8 parts of water-based polyisocyanate
3-5 parts of auxiliary agent
The polyurethane prepolymer is obtained by reacting polyether polyol, diisocyanate, a chain extender and a catalyst; the mass ratio of the polyether polyol to the diisocyanate to the chain extender to the catalyst is (30-40): (10-20): (2-5): (1-3);
the modified diatomite is obtained by modifying the surface of diatomite with a mixture of isopropyl bis (acetoacetato) aluminate and gamma-methacryloxypropyltrimethoxysilane;
the preparation method of the modified diatomite comprises the following steps:
1) mixing isopropyl bis (acetoacetate ethyl) aluminate and gamma-methacryloxypropyl trimethoxysilane to obtain a mixture;
2) stirring and mixing diatomite and the mixture at 60-65 ℃ for 40-60min to obtain modified diatomite;
the mass ratio of the isopropyl di (acetoacetate ethyl) aluminate to the gamma-methacryloxypropyltrimethoxysilane is 3: 7;
the mass ratio of the diatomite to the mixture is 15: 1.
2. the high temperature post-curing polyurethane composition as claimed in claim 1, wherein the preparation method of the polyurethane prepolymer comprises:
the method comprises the following steps: reacting polyether polyol and diisocyanate to obtain a first prepolymer;
step two: reacting the first prepolymer with a chain extender to obtain a second prepolymer;
step three: and reacting the second prepolymer with a catalyst to obtain the polyurethane prepolymer.
3. The high temperature post-cure polyurethane composition according to claim 2, wherein the diisocyanate is isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, diphenylmethane diisocyanate, 2, 4-toluene diisocyanate, or dicyclohexylmethane diisocyanate.
4. The high temperature post-curing polyurethane composition as claimed in claim 2, wherein the chain extender is 2, 2-dimethylolpropionic acid or 2, 2-dimethylolbutyric acid.
5. The high temperature post cure polyurethane composition as claimed in claim 1, wherein the waterborne polyisocyanate is commercial type Bayhydur 3100, Bayhydur XP 2487/1 or Bayhydur XP 2451.
6. The high temperature post-curing polyurethane composition as claimed in claim 1, wherein the auxiliary agent comprises a stabilizer, a plasticizer or an antioxidant.
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