CN109053995B - Preparation method of flame-retardant polyurethane pressure-sensitive adhesive - Google Patents
Preparation method of flame-retardant polyurethane pressure-sensitive adhesive Download PDFInfo
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- CN109053995B CN109053995B CN201810596920.2A CN201810596920A CN109053995B CN 109053995 B CN109053995 B CN 109053995B CN 201810596920 A CN201810596920 A CN 201810596920A CN 109053995 B CN109053995 B CN 109053995B
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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
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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- C08G18/3206—Polyhydroxy compounds aliphatic
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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
- C08G18/30—Low-molecular-weight compounds
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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
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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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
- C08G18/28—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
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
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- 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
- C08K13/02—Organic and inorganic ingredients
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- 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
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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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34928—Salts
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- 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
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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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
- 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
- C08K2003/2217—Oxides; Hydroxides of metals of magnesium
- C08K2003/2224—Magnesium hydroxide
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Abstract
The invention belongs to the technical field of pressure-sensitive adhesives, and particularly relates to a preparation method of a flame-retardant polyurethane pressure-sensitive adhesive, which comprises the following steps: step 1, mixing potassium hydrogen tartrate, tris (2-chloroethyl) phosphate, melamine hypophosphite, magnesium hydroxide and dicyclohexyl methane diisocyanate under the heating condition to prepare flame-retardant modified dicyclohexyl methane diisocyanate; step 2, uniformly mixing the flame-retardant modified dicyclohexylmethane diisocyanate prepared in the step 1 with tetrahydrofuran-propylene oxide copolymerized glycol, adding diethylene glycol, and mixing for 1-2 hours under a heating condition; step 3, adding 1,2, 4-butanetriol-2-sodium sulfonate into the system prepared in the step 2, and mixing for 0.5 to 1 hour under the heating condition; step 4, adding water with equal mass into the mixture prepared in the step 3, and quickly stirring for 3-4 hours to prepare the flame-retardant polyurethane pressure-sensitive adhesive emulsion; the prepared polyurethane pressure-sensitive adhesive has excellent flame retardant property.
Description
Technical Field
The invention belongs to the technical field of pressure-sensitive adhesives, and particularly relates to a preparation method of a flame-retardant polyurethane pressure-sensitive adhesive.
Background
Pressure-sensitive adhesives are short for pressure-sensitive adhesives. Is a type of adhesive that is sensitive to pressure. Pressure-sensitive adhesives can be classified into rubber type and resin type according to the main resin component. The rubber type can be divided into natural rubber and synthetic rubber; the resin type also includes mainly acrylic type, silicone type and polyurethane type. The polyurethane pressure-sensitive adhesive is non-toxic, does not pollute the environment and saves energy.
The polyurethane pressure-sensitive adhesive is widely applied to the technical fields of packaging, automobiles, electronics and electricians and the like, so that the polyurethane pressure-sensitive adhesive has high requirements on the flame retardant property; the prior polyurethane pressure-sensitive adhesive has low flame retardant property, limits the application thereof,
disclosure of Invention
The invention solves the technical problems in the prior art and provides a preparation method of flame-retardant polyurethane pressure-sensitive adhesive.
In order to solve the problems, the technical scheme of the invention is as follows:
a preparation method of flame-retardant polyurethane pressure-sensitive adhesive comprises the following steps:
step 1, mixing potassium hydrogen tartrate, tris (2-chloroethyl) phosphate, melamine hypophosphite, magnesium hydroxide and dicyclohexylmethane diisocyanate according to a mass ratio of 3.6:1:5.6:2:52-68, and mixing under a heating condition to prepare flame-retardant modified dicyclohexylmethane diisocyanate;
step 2, uniformly mixing the flame-retardant modified dicyclohexylmethane diisocyanate prepared in the step 1 and tetrahydrofuran-propylene oxide copolymerized glycol according to the mass ratio of 3.7-4.0:7.4, adding diethylene glycol to ensure that the mass fraction of the added diethylene glycol is 2-4%, and mixing for 1-2 hours under a heating condition;
step 3, adding 1,2, 4-butanetriol-2-sodium sulfonate into the system prepared in the step 2 to ensure that the mass fraction of the 1,2, 4-butanetriol-2-sodium sulfonate is 1-3 percent after the 1,2, 4-butanetriol-2-sodium sulfonate is added, and mixing for 0.5-1 hour under a heating condition;
and 4, adding water with the same mass into the mixture prepared in the step 3, and quickly stirring for 3-4 hours to prepare the flame-retardant polyurethane pressure-sensitive adhesive emulsion.
Preferably, the heating condition of the step 1 is 80-90 ℃.
Preferably, the heating condition of the step 2 is 70-80 ℃.
Preferably, the heating condition of the step 3 is 75-85 ℃.
Preferably, the stirring speed of step 4 is 150-180 rpm.
Preferably, the temperature condition of the step 4 is 35-40 ℃.
Compared with the prior art, the invention has the advantages that,
the raw materials adopted by the preparation method are environment-friendly and nontoxic, the preparation method is simple, and the method can be widely used for industrial production; the prepared polyurethane pressure-sensitive adhesive has excellent flame retardant property and can be widely applied to the fields of packaging, automobiles, electronics and electrics and the like.
Detailed Description
Example 1:
a preparation method of flame-retardant polyurethane pressure-sensitive adhesive comprises the following steps: step 1, mixing potassium hydrogen tartrate, tris (2-chloroethyl) phosphate, melamine hypophosphite, magnesium hydroxide and dicyclohexylmethane diisocyanate according to a mass ratio of 3.6:1:5.6:2:52, and mixing under a heating condition of 80 ℃ to prepare flame-retardant modified dicyclohexylmethane diisocyanate;
step 2, uniformly mixing the flame-retardant modified dicyclohexylmethane diisocyanate prepared in the step 1 and tetrahydrofuran-propylene oxide copolymerized glycol according to the mass ratio of 3.7:7.4, adding diethylene glycol to ensure that the mass fraction of the added diethylene glycol is 2%, and mixing for 1 hour under the heating condition of 70 ℃;
step 3, adding 1,2, 4-butanetriol-2-sodium sulfonate into the system prepared in the step 2 to ensure that the mass fraction of the 1,2, 4-butanetriol-2-sodium sulfonate is 1 percent after the 1,2, 4-butanetriol-2-sodium sulfonate is added, and mixing for 0.5 hour under the heating condition of 75 ℃;
and 4, adding water with the same mass into the mixture prepared in the step 3, and stirring for 3 hours at 35 ℃ and 150rpm to prepare the flame-retardant polyurethane pressure-sensitive adhesive emulsion.
Example 2:
a preparation method of flame-retardant polyurethane pressure-sensitive adhesive comprises the following steps: step 1, mixing potassium hydrogen tartrate, tris (2-chloroethyl) phosphate, melamine hypophosphite, magnesium hydroxide and dicyclohexylmethane diisocyanate according to a mass ratio of 3.6:1:5.6:2:60, and mixing under a heating condition of 85 ℃ to prepare flame-retardant modified dicyclohexylmethane diisocyanate;
step 2, uniformly mixing the flame-retardant modified dicyclohexylmethane diisocyanate prepared in the step 1 and tetrahydrofuran-propylene oxide copolymerized glycol according to the mass ratio of 3.9:7.4, adding diethylene glycol to ensure that the mass fraction of the added diethylene glycol is 3%, and mixing for 1.5 hours under the heating condition of 75 ℃;
step 3, adding 1,2, 4-butanetriol-2-sodium sulfonate into the system prepared in the step 2 to ensure that the mass fraction of the 1,2, 4-butanetriol-2-sodium sulfonate is 2 percent after the 1,2, 4-butanetriol-2-sodium sulfonate is added, and mixing for 1 hour under the heating condition of 80 ℃;
and 4, adding water with the same mass into the mixture prepared in the step 3, and stirring for 3.5 hours at 35 ℃ and 170rpm to prepare the flame-retardant polyurethane pressure-sensitive adhesive emulsion.
Example 3:
a preparation method of flame-retardant polyurethane pressure-sensitive adhesive comprises the following steps: step 1, mixing potassium hydrogen tartrate, tris (2-chloroethyl) phosphate, melamine hypophosphite, magnesium hydroxide and dicyclohexylmethane diisocyanate according to a mass ratio of 3.6:1:5.6:2:68, and mixing under a heating condition of 90 ℃ to prepare flame-retardant modified dicyclohexylmethane diisocyanate;
step 2, uniformly mixing the flame-retardant modified dicyclohexylmethane diisocyanate prepared in the step 1 and tetrahydrofuran-propylene oxide copolymerized glycol according to the mass ratio of 4.0:7.4, adding diethylene glycol so that the mass fraction of the added diethylene glycol is 4%, and mixing for 2 hours under the heating condition of 80 ℃;
step 3, adding 1,2, 4-butanetriol-2-sodium sulfonate into the system prepared in the step 2 to ensure that the mass fraction of the 1,2, 4-butanetriol-2-sodium sulfonate is 3 percent after the 1,2, 4-butanetriol-2-sodium sulfonate is added, and mixing for 1 hour under the heating condition of 85 ℃;
and 4, adding water with the same mass into the mixture prepared in the step 3, and stirring for 4 hours at 40 ℃ and 180rpm to prepare the flame-retardant polyurethane pressure-sensitive adhesive emulsion.
Comparative example 1:
a preparation method of flame-retardant polyurethane pressure-sensitive adhesive comprises the following steps: step 1, mixing tris (2-chloroethyl) phosphate, melamine hypophosphite, magnesium hydroxide and dicyclohexylmethane diisocyanate according to the mass ratio of 1:5.6:2:52, and mixing under the heating condition of 80 ℃ to prepare the flame-retardant modified dicyclohexylmethane diisocyanate;
step 2, uniformly mixing the flame-retardant modified dicyclohexylmethane diisocyanate prepared in the step 1 and tetrahydrofuran-propylene oxide copolymerized glycol according to the mass ratio of 3.7:7.4, adding diethylene glycol to ensure that the mass fraction of the added diethylene glycol is 2%, and mixing for 1 hour under the heating condition of 70 ℃;
step 3, adding 1,2, 4-butanetriol-2-sodium sulfonate into the system prepared in the step 2 to ensure that the mass fraction of the 1,2, 4-butanetriol-2-sodium sulfonate is 1 percent after the 1,2, 4-butanetriol-2-sodium sulfonate is added, and mixing for 0.5 hour under the heating condition of 75 ℃;
and 4, adding water with the same mass into the mixture prepared in the step 3, and stirring for 3 hours at 35 ℃ and 150rpm to prepare the flame-retardant polyurethane pressure-sensitive adhesive emulsion.
Example 4:
the flame retardant polyurethane pressure-sensitive adhesives prepared in examples 1-3 and comparative example 1 were subjected to a flame retardant performance test (according to the UL94 standard), and the flame retardancy of the flame retardant polyurethane pressure-sensitive adhesives of examples 1-3 reached V-0 grade, and the flame retardancy of comparative example 1 was V-2 grade.
It should be noted that the above-mentioned embodiments are only preferred embodiments of the present invention, and are not intended to limit the scope of the present invention, and all equivalent substitutions or substitutions made on the above-mentioned embodiments are included in the scope of the present invention.
Claims (6)
1. The preparation method of the flame-retardant polyurethane pressure-sensitive adhesive is characterized by comprising the following steps of:
step 1, mixing potassium hydrogen tartrate, tris (2-chloroethyl) phosphate, melamine hypophosphite, magnesium hydroxide and dicyclohexylmethane diisocyanate according to a mass ratio of 3.6:1:5.6:2:52-68, and mixing under a heating condition to prepare flame-retardant modified dicyclohexylmethane diisocyanate;
step 2, uniformly mixing the flame-retardant modified dicyclohexylmethane diisocyanate prepared in the step 1 and tetrahydrofuran-propylene oxide copolymerized glycol according to the mass ratio of 3.7-4.0:7.4, adding diethylene glycol to ensure that the mass fraction of the added diethylene glycol is 2-4%, and mixing for 1-2 hours under a heating condition;
step 3, adding 1,2, 4-butanetriol-2-sodium sulfonate into the system prepared in the step 2 to ensure that the mass fraction of the 1,2, 4-butanetriol-2-sodium sulfonate is 1-3 percent after the 1,2, 4-butanetriol-2-sodium sulfonate is added, and mixing for 0.5-1 hour under a heating condition;
and 4, adding water with the same mass into the mixture prepared in the step 3, and quickly stirring for 3-4 hours to prepare the flame-retardant polyurethane pressure-sensitive adhesive emulsion.
2. The method for preparing the flame-retardant polyurethane pressure-sensitive adhesive according to claim 1, wherein the heating condition of step 1 is 80-90 ℃.
3. The method for preparing the flame-retardant polyurethane pressure-sensitive adhesive according to claim 1, wherein the heating condition of the step 2 is 70-80 ℃.
4. The method for preparing the flame-retardant polyurethane pressure-sensitive adhesive according to claim 1, wherein the heating condition of the step 3 is 75-85 ℃.
5. The method for preparing the flame-retardant polyurethane pressure-sensitive adhesive as claimed in claim 1, wherein the stirring speed in step 4 is 150-180 rpm.
6. The method for preparing the flame-retardant polyurethane pressure-sensitive adhesive according to claim 1, wherein the temperature condition of the step 4 is 35 to 40 ℃.
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| CN114989105B (en) * | 2022-07-15 | 2024-01-12 | 什邡市太丰新型阻燃剂有限责任公司 | Pollution-free method for synthesizing superfine melamine hypophosphite and flame-retardant method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999038900A1 (en) * | 1998-01-28 | 1999-08-05 | Bristol-Myers Squibb Company | Methods of preparing polyurethane adhesives, adhesives produced thereby and medical devices employing the same |
| WO2003052021A1 (en) * | 2001-12-18 | 2003-06-26 | 3M Innovative Properties Company | Silicone priming compositions, articles and methods_____________ |
| CN103820070A (en) * | 2014-03-07 | 2014-05-28 | 广州北峻工业材料有限公司 | Water-based polyurethane pressure-sensitive adhesive and preparation method thereof |
| CN105164141A (en) * | 2013-04-17 | 2015-12-16 | 佳能株式会社 | Novel compound and resin composition containing the same |
| CN105229082A (en) * | 2013-05-17 | 2016-01-06 | 佳能株式会社 | Flame-retardant composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7012110B2 (en) * | 2001-12-18 | 2006-03-14 | 3M Innovative Properties Company | Silicone pressure sensitive adhesives prepared using processing aids, articles, and methods |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999038900A1 (en) * | 1998-01-28 | 1999-08-05 | Bristol-Myers Squibb Company | Methods of preparing polyurethane adhesives, adhesives produced thereby and medical devices employing the same |
| WO2003052021A1 (en) * | 2001-12-18 | 2003-06-26 | 3M Innovative Properties Company | Silicone priming compositions, articles and methods_____________ |
| CN105164141A (en) * | 2013-04-17 | 2015-12-16 | 佳能株式会社 | Novel compound and resin composition containing the same |
| CN105229082A (en) * | 2013-05-17 | 2016-01-06 | 佳能株式会社 | Flame-retardant composition |
| CN103820070A (en) * | 2014-03-07 | 2014-05-28 | 广州北峻工业材料有限公司 | Water-based polyurethane pressure-sensitive adhesive and preparation method thereof |
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