CN110184016B - Flame-retardant bi-component adhesive and preparation method thereof - Google Patents
Flame-retardant bi-component adhesive and preparation method thereof Download PDFInfo
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- CN110184016B CN110184016B CN201910530130.9A CN201910530130A CN110184016B CN 110184016 B CN110184016 B CN 110184016B CN 201910530130 A CN201910530130 A CN 201910530130A CN 110184016 B CN110184016 B CN 110184016B
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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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3882—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
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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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3882—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/3885—Phosphate compounds
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3889—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having nitrogen in addition to phosphorus
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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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2227—Oxides; Hydroxides of metals of aluminium
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
Abstract
The invention discloses a flame-retardant bi-component adhesive, which comprises a component A and a component B, wherein the component A and the component B are respectively composed of the following substances in percentage by weight: 55-85% of modified isocyanate prepolymer, 6-20% of flame retardant a, 8-22% of filler a and 1-3% of stabilizer; and B component: 30-75% of polyol, 3-10% of amine, 2-5% of coupling agent, 10-30% of flame retardant b and 10-25% of filler b; the weight ratio of the component A to the component B is 1: 1. The polyurethane prepolymer with flame retardant property is prepared by modifying the polyurethane prepolymer with the hydroxyl-terminated phosphorus copolymer, has flame retardant property when used as an adhesive, and simultaneously maintains the strength and the heat conducting property of the traditional two-component polyurethane adhesive. The flame-retardant bi-component adhesive disclosed by the invention has good application in the aspects of bonding new energy battery structures and the like, and has very high bonding strength for plastics and metals.
Description
Technical Field
The invention relates to the field of adhesives, in particular to a flame-retardant bi-component adhesive and a preparation method thereof.
Background
The flame-retardant bi-component polyurethane adhesive for the new energy battery is required to have the characteristics of high strength, excellent thermal conductivity, good flame retardance, suitability for bonding of different materials, solvent corrosion resistance, high temperature resistance and the like. Compared with the traditional adhesive, the bi-component adhesive has high temperature resistance and good heat conductivity, and can be applied to new energy batteries to solve some limitations faced by the traditional curing adhesive. However, in some special scenarios, in addition to the requirements for high strength and thermal conductivity, flame retardant adhesives are required to improve the safety and reliability of the battery.
Disclosure of Invention
The invention provides a flame-retardant bi-component adhesive and a preparation method thereof, aiming at the problem that the existing bi-component adhesive for batteries does not have flame retardance.
The technical scheme for solving the technical problems is as follows: the flame-retardant bi-component adhesive comprises a component A and a component B, and is characterized in that the component A and the component B are respectively composed of the following substances in percentage by weight: 55-85% of modified isocyanate prepolymer, 6-20% of flame retardant a, 8-22% of filler a and 1-3% of stabilizer; and B component: 30-75% of polyol, 3-10% of amine, 2-5% of coupling agent, 10-30% of flame retardant b and 10-25% of filler b; the weight ratio of the component A to the component B is 1: 1.
The modified isocyanate prepolymer is prepared from the following substances in parts by weight: 120-180 parts of isocyanate, 30-70 parts of dihydric alcohol, 60-100 parts of phosphorus flame retardant containing hydroxyl, 0.05-1 part of dibutyltin dilaurate and 0.05-5 parts of polymerization inhibitor; the isocyanate is one of dimer or trimer of IPDI, MDI, HMDI, HDI and TDI, the dihydric alcohol is one of PPG200, PPG400, PEG400, PTMEG1000 or PCDL500, the hydroxyl-containing phosphorus flame retardant is one of tris (2-carbonyl ethyl) phosphate, diethyl N, N-bis (2-hydroxyethyl) aminomethylphosphonate or tris (2-chloropropyl) phosphate, and the polymerization inhibitor is one of hydroquinone, tert-butyl catechol or phosphoric acid.
Further, the flame retardant a and the flame retardant b are independently selected from one of cresyldiphenyl phosphate, isopropylated triphenyl phosphate, trixylenyl phosphate or tricresyl phosphate.
Further, the filler a and the filler b are independently selected from one of alumina, aluminum hydroxide or graphene.
Further, the stabilizer is hydroquinone or naphthoquinone.
Further, the polyhydric alcohol is propylene glycol or glycerol.
Further, the amine is one of 4, 4' -bis-sec-butylaminodiphenylmethane, MOCA, D5000 or D2000.
Further, the coupling agent is one of gamma-aminopropyltriethoxysilane, gamma- (2, 3-glycidoxy) propyltrimethoxysilane, gamma- (methacryloyloxy) propyltrimethoxysilane, vinyltris (beta-methoxyethoxy) silane, vinyltrimethoxysilane or vinyltriethoxysilane.
The invention also relates to a preparation method of the flame-retardant bi-component adhesive, which comprises the following steps:
1) preparing a modified isocyanate prepolymer: weighing isocyanate, dihydric alcohol, a phosphorus flame retardant containing hydroxyl, dibutyltin dilaurate and a polymerization inhibitor according to the weight parts, uniformly mixing the isocyanate and the dihydric alcohol, adding dibutyltin dilaurate, heating for 2-6h at 60-90 ℃ under the protection of nitrogen to prepare isocyanate resin, vacuumizing for 1-2h at 110-130 ℃, cooling to 15-40 ℃, adding the isocyanate resin, reacting for 2-5h at 70-115 ℃, adding the polymerization inhibitor, and preserving heat for 0.5-2h to prepare a modified isocyanate prepolymer;
2) preparing a flame-retardant bi-component adhesive: weighing the components A and B according to the weight percentage, respectively and uniformly mixing under the vacuum-pumping state, and then independently storing.
The invention has the beneficial effects that: the polyurethane prepolymer with flame retardant property is prepared by modifying the polyurethane prepolymer with the hydroxyl-terminated phosphorus copolymer, has flame retardant property when used as an adhesive, and simultaneously maintains the strength and the heat conducting property of the traditional two-component polyurethane adhesive. The flame-retardant bi-component adhesive disclosed by the invention has good application in the aspects of bonding new energy battery structures and the like, and has very high bonding strength for plastics and metals.
Detailed Description
The present invention is described below with reference to examples, which are provided for illustration only and are not intended to limit the scope of the present invention.
Example 1
A flame-retardant bi-component adhesive comprises a component A and a component B, wherein the component A and the component B respectively consist of the following substances in percentage by weight,
the component A comprises: 85% of modified isocyanate prepolymer, 6% of diphenyl cresyl phosphate, 8% of alumina and 1% of hydroquinone; and B component: 75% of propylene glycol, 3% of 4, 4' -bis-sec-butylaminodiphenylmethane, 2% of gamma-aminopropyltriethoxysilane, 10% of diphenyl cresylphosphate and 10% of aluminum hydroxide; the weight ratio of the component A to the component B is 1: 1.
The modified isocyanate prepolymer is prepared from the following substances in parts by weight: 120 parts of IPDI dimer, 20070 parts of PPG, 60 parts of tris (2-carbonyl ethyl) phosphate hydrochloride, 1 part of dibutyltin dilaurate and 0.05 part of hydroquinone.
The preparation method of the flame-retardant bi-component adhesive comprises the following steps:
1) preparing a modified isocyanate prepolymer: weighing IPDI dimer, PPG200, tris (2-carbonyl ethyl) phosphate, dibutyltin dilaurate and hydroquinone according to weight parts, uniformly mixing the IPDI dimer and the PPG200, adding dibutyltin dilaurate, heating for 6h at 60 ℃ under the protection of nitrogen to prepare isocyanate resin, vacuumizing tris (2-carbonyl ethyl) phosphate for 1h at 130 ℃, cooling to 15 ℃, adding the isocyanate resin, reacting for 2h at 115 ℃, adding the hydroquinone, and preserving heat for 2h to prepare a modified isocyanate prepolymer;
2) preparing a flame-retardant bi-component adhesive: weighing the components A and B according to the weight percentage, respectively and uniformly mixing under the vacuum-pumping state, and then independently storing.
Example 2
A flame-retardant bi-component adhesive comprises a component A and a component B, wherein the component A and the component B respectively consist of the following substances in percentage by weight,
the component A comprises: 70% of modified isocyanate prepolymer, 13% of tri (xylene) phosphate, 15% of aluminum hydroxide and 2% of naphthoquinone; and B component: 50% of glycerol, 6% of MOCA, 4% of gamma- (2, 3-epoxypropoxy) propyl trimethoxy silane, 20% of isopropylated triphenyl phosphate and 20% of graphene; the weight ratio of the component A to the component B is 1: 1.
The modified isocyanate prepolymer is prepared from the following substances in parts by weight: 150 parts of MDI tripolymer, 50 parts of PEG400, 80 parts of diethyl N, N-bis (2-hydroxyethyl) aminomethylphosphonate, 0.5 part of dibutyltin dilaurate and 2.5 parts of tert-butyl catechol.
The preparation method of the flame-retardant bi-component adhesive comprises the following steps:
1) preparing a modified isocyanate prepolymer: weighing MDI tripolymer, PEG400, N-bis (2-hydroxyethyl) diethyl aminomethylphosphonate, dibutyltin dilaurate and tert-butyl catechol according to the weight parts, uniformly mixing the MDI tripolymer and the PEG400, adding dibutyltin dilaurate, heating for 4h at 75 ℃ under the protection of nitrogen to prepare isocyanate resin, vacuumizing for 1.5h at 120 ℃ for N, N-bis (2-hydroxyethyl) diethyl aminomethylphosphonate, cooling to 25 ℃, adding the isocyanate resin, reacting for 3.5h at 90 ℃, adding the tert-butyl catechol, and preserving heat for 1h to prepare a modified isocyanate prepolymer;
2) preparing a flame-retardant bi-component adhesive: weighing the components A and B according to the weight percentage, respectively and uniformly mixing under the vacuum-pumping state, and then independently storing.
Example 3
A flame-retardant bi-component adhesive comprises a component A and a component B, wherein the component A and the component B respectively consist of the following substances in percentage by weight,
the component A comprises: 55% of modified isocyanate prepolymer, 20% of tricresyl phosphate, 22% of graphene and 3% of naphthoquinone; and B component: 30% of propylene glycol, 200010% of D, 5% of vinyl triethoxysilane, 30% of tricresyl phosphate and 25% of alumina; the weight ratio of the component A to the component B is 1: 1.
The modified isocyanate prepolymer is prepared from the following substances in parts by weight: 180 parts of TDI dimer, 50030 parts of PCDL, 100 parts of tris (2-chloropropyl) phosphate, 0.05 part of dibutyltin dilaurate and 5 parts of phosphoric acid.
The preparation method of the flame-retardant bi-component adhesive comprises the following steps:
1) preparing a modified isocyanate prepolymer: weighing TDI dimer, PCDL500, tris (2-chloropropyl) phosphate, dibutyltin dilaurate and phosphoric acid in parts by weight, uniformly mixing the TDI dimer and the PCDL500, adding dibutyltin dilaurate, heating for 2h at 90 ℃ under the protection of nitrogen to prepare isocyanate resin, vacuumizing for 2h at 110 ℃, cooling to 40 ℃, adding the isocyanate resin, reacting for 5h at 70 ℃, adding the phosphoric acid, and preserving heat for 0.5h to prepare a modified isocyanate prepolymer;
2) preparing a flame-retardant bi-component adhesive: weighing the components A and B according to the weight percentage, respectively and uniformly mixing under the vacuum-pumping state, and then independently storing.
The flame-retardant bi-component adhesive obtained in examples 1 to 3 was subjected to relevant performance tests, and the results are shown in table 1.
TABLE 1 EXAMPLES 1-3 Performance test of flame retardant bicomponent adhesive
| Examples | Example 1 | Example 2 | Example 3 |
| Operating time (min) | 15 | 18 | 13 |
| Complete curing time (h) | 24 | 24 | 24 |
| Hardness (shoreD) | 50 | 46 | 55 |
| Shear strength (MPa) | 12 | 10 | 14 |
| Temperature resistance (. degree. C.) | 120 | 150 | 120 |
| Flame retardancy limit oxygen index | Self-extinguishing when away from fire | Self-extinguishing when away from fire | Self-extinguishing when away from fire |
| Thermal conductivity (w/m.k) | 1.0 | 1.5 | 1.2 |
As can be seen from the data in the table, the flame-retardant bi-component adhesives obtained in the examples 1 to 3 have better strength, temperature resistance, flame retardance and thermal conductivity.
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 (7)
1. The flame-retardant bi-component adhesive comprises a component A and a component B and is characterized in that the component A and the component B respectively consist of the following substances in percentage by weight,
the component A comprises: 55-85% of modified isocyanate prepolymer, 6-20% of flame retardant a, 8-22% of filler a and 1-3% of stabilizer; and B component: 30-75% of polyol, 3-10% of amine, 2-5% of coupling agent, 10-30% of flame retardant b and 10-25% of filler b; the weight ratio of the component A to the component B is 1: 1;
the modified isocyanate prepolymer is prepared from the following substances in parts by weight: 120-180 parts of isocyanate, 30-70 parts of dihydric alcohol, 60-100 parts of phosphorus flame retardant, 0.05-1 part of dibutyltin dilaurate and 0.05-5 parts of polymerization inhibitor;
the phosphorus flame retardant is one of tris (2-carbonylethyl) phosphate, diethyl N, N-bis (2-hydroxyethyl) aminomethylphosphonate or tris (2-chloropropyl) phosphate, and the polymerization inhibitor is one of hydroquinone, tert-butyl catechol or phosphoric acid;
the flame retardant a and the flame retardant b are independently selected from one of cresyldiphenyl phosphate, isopropylated triphenyl phosphate, trixylenyl phosphate or tricresyl phosphate;
the filler a and the filler b are independently selected from one of alumina, aluminum hydroxide or graphene;
the preparation method of the modified isocyanate prepolymer comprises the following steps: weighing isocyanate, dihydric alcohol, a phosphorus flame retardant, dibutyltin dilaurate and a polymerization inhibitor according to the weight parts, uniformly mixing the isocyanate and the dihydric alcohol, adding dibutyltin dilaurate, heating for 2-6h at 60-90 ℃ under the protection of nitrogen to prepare isocyanate resin, vacuumizing for 1-2h at 110-130 ℃, cooling to 15-40 ℃, adding the isocyanate resin, reacting for 2-5h at 70-115 ℃, adding the polymerization inhibitor, and preserving heat for 0.5-2h to prepare the modified isocyanate prepolymer.
2. The flame retardant two-component adhesive of claim 1, wherein the isocyanate is one of IPDI, MDI, HMDI, HDI, dimer or trimer of TDI, and the diol is one of PPG200, PPG400, PEG400, PTMEG1000 or PCDL 500.
3. The flame retardant two-component adhesive according to claim 1 or 2, wherein the stabilizer is hydroquinone or naphthoquinone.
4. The flame retardant two-component adhesive according to claim 1 or 2, wherein the polyol is propylene glycol or glycerol.
5. The flame retardant bicomponent adhesive according to claim 1 or 2, wherein the amine is one of 4, 4' -bis-sec-butylaminodiphenylmethane, MOCA, D5000 or D2000.
6. The flame retardant two-component adhesive according to claim 1 or 2, wherein the coupling agent is one of gamma-aminopropyltriethoxysilane, gamma- (2, 3-glycidoxy) propyltrimethoxysilane, gamma- (methacryloyloxy) propyltrimethoxysilane, vinyltris (beta-methoxyethoxy) silane, vinyltrimethoxysilane, or vinyltriethoxysilane.
7. The preparation method of the flame-retardant two-component adhesive according to any one of claims 1 to 6, characterized by comprising the following steps:
1) preparing a modified isocyanate prepolymer: weighing isocyanate, dihydric alcohol, a phosphorus flame retardant, dibutyltin dilaurate and a polymerization inhibitor according to the weight parts, uniformly mixing the isocyanate and the dihydric alcohol, adding dibutyltin dilaurate, heating for 2-6h at 60-90 ℃ under the protection of nitrogen to prepare isocyanate resin, vacuumizing the phosphorus flame retardant for 1-2h at 110-130 ℃, cooling to 15-40 ℃, adding the isocyanate resin, reacting for 2-5h at 70-115 ℃, adding the polymerization inhibitor, and preserving heat for 0.5-2h to prepare a modified isocyanate prepolymer;
2) preparing a flame-retardant bi-component adhesive: weighing the components A and B according to the weight percentage, respectively and uniformly mixing under the vacuum-pumping state, and then independently storing.
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| CN112175566B (en) * | 2020-09-28 | 2022-11-25 | 杭州应星新材料有限公司 | Room-temperature curing bi-component polyurethane heat-conducting composition and preparation method thereof |
| CN113969130A (en) * | 2021-10-10 | 2022-01-25 | 郑州大学 | Graphene oxide in-situ polymerization modified bi-component polyurethane adhesive and preparation method thereof |
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