CN111978705B - Mixed antibacterial polyurethane and preparation method thereof - Google Patents
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- CN111978705B CN111978705B CN202010676336.5A CN202010676336A CN111978705B CN 111978705 B CN111978705 B CN 111978705B CN 202010676336 A CN202010676336 A CN 202010676336A CN 111978705 B CN111978705 B CN 111978705B
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
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- C08K3/24—Acids; Salts thereof
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
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- C08G18/40—High-molecular-weight compounds
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- C08G18/40—High-molecular-weight compounds
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- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4816—Two or more polyethers of different physical or chemical nature mixtures of two or more polyetherpolyols having at least three hydroxy groups
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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
- C08G18/4829—Polyethers containing at least three hydroxy groups
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- 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
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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
- C08G18/70—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
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
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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
- C08G18/70—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
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
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- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
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- C08K5/54—Silicon-containing compounds
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Abstract
The invention discloses a mixed antibacterial polyurethane and a preparation method thereof, wherein the mixed antibacterial polyurethane is prepared from the following raw materials in parts by weight: 75-90 parts of polyol, 80-90 parts of diisocyanate, 2-2.5 parts of catalyst, 25-35 parts of physical modifier, 0.5-1.0 part of trimethylolpropane and 4-5.5 parts of methyltriethoxysilane.
Description
Technical Field
The invention relates to the technical field of polyurethane, and particularly belongs to mixed antibacterial polyurethane and a preparation method thereof.
Background
Polyurethane (PU) is a high molecular material containing repeated carbamate (-NHCOO-) chain segments, and is one of the most widely used polymers at present, and the application range of the PU comprises coatings, adhesives, furniture, paints, automobile lubricating oil additives, medical synthetic materials, food packaging, shoes, building materials, gaskets and the like.
Polyurethane materials are easily disturbed by bacteria during use because the polyether or polyester segments of the polyurethane macromolecules can serve as a carbon source for microbial growth. Meanwhile, some additive ingredients such as plasticizers, lignocelluloses, stabilizers, coloring agents and the like in the polyurethane material are also easily attacked by microorganisms, which causes many problems in the use of the polyurethane material. With the enhancement of public health consciousness, the demand for improving the antibacterial performance of polyurethane is increasing while improving the physicochemical performance of polyurethane.
Disclosure of Invention
The invention aims to provide a mixed antibacterial polyurethane and a preparation method thereof, overcomes the defects of the prior art, and improves the antibacterial performance of the polyurethane through physical modification.
In order to solve the problems, the technical scheme adopted by the invention is as follows:
the mixed antibacterial polyurethane is prepared from the following raw materials in parts by weight: 75-90 parts of polyol, 80-90 parts of diisocyanate, 2-2.5 parts of catalyst, 25-35 parts of physical modifier, 0.5-1.0 part of trimethylolpropane and 4-5.5 parts of methyltriethoxysilane.
Preferably, the polyalcohol is formed by mixing polyoxypropylene triol, polyoxypropylene diol, poly (1, 4-succinic acid-hexylene diester diol) and polytetrahydrofuran ether diol in a weight ratio of 20-30:20-25:15-20: 25-30.
Preferably, the molecular weight of the polyoxypropylene triol and the polytetrahydrofuran ether glycol is 1000, and the molecular weight of the polyoxypropylene diol and the molecular weight of the poly-1, 4-succinic acid hexamethylene diester diol are 2000.
Preferably, the physical modifier consists of phenyl salicylate and sodium hexafluoroaluminate in a weight ratio of 15-20: 10-15.
Preferably, the catalyst is dibutyltin dilaurate.
Preferably, the physical modifier consists of phenyl salicylate, zinc stearate and sodium hexafluoroaluminate in a weight ratio of 15-20:3-5: 10-15.
Preferably, the diisocyanate is one of toluene diisocyanate, cyclohexyl diisocyanate and isophorone diisocyanate.
A method of preparing a hybrid antimicrobial polyurethane comprising the steps of:
(1) dehydrating polyol, adding diisocyanate and a catalyst, and reacting at 60-70 ℃ and-0.1 Mpa for 30-40min to obtain a solution A;
(2) adding physical modifier into the solution A, and reacting at 90-95 deg.C under-0.1 Mpa for 3-40 min; obtaining a pre-polymerization solution;
(3) and adding trimethylolpropane and methyltriethoxysilane into the prepolymerization liquid, and then heating to 100-110 ℃ for continuing to react for 40-50min to obtain the mixed antibacterial polyurethane.
Compared with the prior art, the invention has the following implementation effects:
1. according to the invention, the physical modifier is added into the polyurethane prepolymer liquid, so that the modified polyurethane has antibacterial capability, and the polyurethane has good tensile resistance.
2. According to the invention, phenyl salicylate and sodium hexafluoroaluminate are compounded, the sodium hexafluoroaluminate has moisture absorption capacity, so that the water content of the sodium hexafluoroaluminate is increased, bacteria are gathered, sodium ions of the sodium hexafluoroaluminate can penetrate through cell walls of the bacteria, the phenyl salicylate is driven to move towards the cell walls of the bacteria, the cell walls of the bacteria are surrounded by phenyl salicylate molecules under the combination of ester groups and the cell walls, the bacteria are prevented from growing and exchanging substances, the bacteria are killed, the sterilization effect is generated, and the antibacterial property of polyurethane is further generated.
3. The invention also uses zinc stearate as physical modifier, zinc stearate is common plasticizer, which can obviously improve the plasticizing performance of plastic products, and after the zinc stearate is added into the polyurethane, the tensile resistance of the polyurethane is only slightly reduced, but the antibacterial ability reaches more than 99.5%.
4. The zinc stearate of the invention generates electron transfer function with dibutyltin dilaurate which is an active catalyst in a polyurethane system, so that electrons in transition metal zinc are transferred between zinc ions and tin ions, redox function is generated in the electron transfer process, when bacteria are contacted with polyurethane, the transferred partial electrons take bacteria as a medium, the bacteria are accelerated to age, so that the bacteria die, the added zinc stearate generates antibacterial capability in the polyurethane containing dibutyltin dilaurate, and the antibacterial capability of the polyurethane is more than 99.5 percent after the zinc stearate is superposed with the antibacterial function of phenyl salicylate and sodium hexafluoroaluminate.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A preparation method of mixed antibacterial polyurethane comprises the following steps:
(1) 24g of polyoxypropylene triol with the molecular weight of 1000, 24g of polyoxypropylene diol with the molecular weight of 2000, 18.5g of poly-1, 4-succinic acid hexamethylene diester diol with the molecular weight of 2000 and 25g of polytetrahydrofuran ether diol with the molecular weight of 1000 are stirred and mixed uniformly, and then heated to 80 ℃ under-0.1 Mpa for vacuum dehydration for 40 min.
(2) Cooling the solution in the step (1) to 70 ℃, adding 83.6g of toluene diisocyanate and 2.3g of dibutyltin dilaurate, uniformly stirring, and reacting for 30min under-0.1 Mpa;
(3) adding 18.6g of phenyl salicylate and 11.6g of sodium hexafluoroaluminate into the mixed solution after the reaction in the step (2), and reacting for 40min at 90 ℃ under-0.1 Mpa; obtaining a pre-polymerization solution;
(4) then, 0.9g of trimethylolpropane and 4.3g of methyltriethoxysilane were added to the prepolymerization solution, and the reaction was continued at 110 ℃ for 40min to obtain a mixed antibacterial polyurethane.
Example 2
A preparation method of mixed antibacterial polyurethane comprises the following steps:
(1) 27g of polyoxypropylene triol with the molecular weight of 1000, 22g of polyoxypropylene diol with the molecular weight of 2000, 16g of poly (1, 4-hexanediol succinate) with the molecular weight of 2000 and 28g of polytetrahydrofuran ether diol with the molecular weight of 1000 are stirred and mixed uniformly, and then heated to 85 ℃ under-0.1 Mpa for vacuum dehydration for 50 min.
(2) Cooling the solution in the step (1) to 65 ℃, adding 86g of cyclohexyl diisocyanate and 2.7g of dibutyltin dilaurate, uniformly stirring, and reacting for 40min under-0.1 Mpa;
(3) adding 16g of phenyl salicylate and 14g of sodium hexafluoroaluminate into the mixed solution after the reaction in the step (2), and reacting for 35min at 95 ℃ under-0.1 Mpa; obtaining a pre-polymerization solution;
(4) then, 0.7g of trimethylolpropane and 5.5g of methyltriethoxysilane were added to the prepolymerization solution, and the reaction was continued at 105 ℃ for 45min to obtain a mixed antibacterial polyurethane.
Example 3
A preparation method of mixed antibacterial polyurethane comprises the following steps:
(1) 28g of polyoxypropylene triol with the molecular weight of 1000, 25g of polyoxypropylene diol with the molecular weight of 2000, 15g of poly (1, 4-hexanediol succinate) with the molecular weight of 2000 and 26g of polytetrahydrofuran ether diol with the molecular weight of 1000 are stirred and mixed uniformly, and then heated to 70 ℃ under-0.1 Mpa for vacuum dehydration for 45 min.
(2) Cooling the solution in the step (1) to 70 ℃, adding 84.8g of isophorone diisocyanate and 2.2g of dibutyltin dilaurate, uniformly stirring, and reacting for 35min under-0.1 MPa;
(3) adding 17g of phenyl salicylate, 3.6g of zinc stearate and 11g of sodium hexafluoroaluminate into the mixed solution after the reaction in the step (2), and reacting for 40min at 95 ℃ under-0.1 Mpa; obtaining a pre-polymerization solution;
(4) then, 0.8g of trimethylolpropane and 5g of methyltriethoxysilane were added to the prepolymerization solution, and the reaction was continued at 110 ℃ for 50min to obtain a mixed antibacterial polyurethane.
Comparative example 1
The difference from example 1 is that phenyl salicylate was added in an amount of 0.
Comparative example 2
The difference from example 1 is that sodium hexafluoroaluminate is added in an amount of 0.
Comparative example 3
The difference from example 3 is that phenyl salicylate and sodium hexafluoroaluminate were added in an amount of 0.
The mixed antibacterial polyurethane in the examples 1-3 and the comparative examples 1-2 has the following antibacterial performance according to GB/T31402-2015 test and tensile strength results according to GB/T1040.1-2018 test:
the above table shows that the antibacterial performance of the polyurethane is remarkably improved by compounding phenyl salicylate and sodium hexafluoroaluminate as a physical additive of the polyurethane, the antibacterial performance of the polyurethane reaches over 99.5% by further using a plasticizer zinc stearate as an additive, and the tensile strength of the polyurethane is only slightly reduced.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (6)
1. The mixed antibacterial polyurethane is characterized by being prepared from the following raw materials in parts by weight: 75-90 parts of polyol, 80-90 parts of diisocyanate, 2-2.5 parts of catalyst, 25-35 parts of physical modifier, 0.5-1.0 part of trimethylolpropane and 4-5.5 parts of methyltriethoxysilane;
the physical modifier consists of phenyl salicylate and sodium hexafluoroaluminate in a weight ratio of 15-20: 10-15;
the catalyst is dibutyltin dilaurate.
2. The mixed antibacterial polyurethane as claimed in claim 1, wherein the polyol is prepared by mixing polyoxypropylene triol, polyoxypropylene diol, poly-1, 4-succinic acid hexanediol and polytetrahydrofuran ether glycol in a weight ratio of 20-30:20-25:15-20: 25-30.
3. The mixed antibacterial polyurethane of claim 2, wherein the molecular weight of the polyoxypropylene triol and the polytetrahydrofuran ether glycol is 1000, and the molecular weight of the polyoxypropylene diol and the molecular weight of the poly-1, 4-hexanediol succinate are 2000.
4. The mixed antibacterial polyurethane of claim 1, wherein the physical modifier further comprises zinc stearate, and the weight ratio of the zinc stearate to the phenyl salicylate and the sodium hexafluoroaluminate is 3-5:15-20: 10-15.
5. The mixed antibacterial polyurethane of claim 1, wherein the diisocyanate is one of toluene diisocyanate, cyclohexyl diisocyanate, and isophorone diisocyanate.
6. A process for preparing a hybrid antibacterial polyurethane according to any one of claims 1 to 5, comprising the steps of:
(1) dehydrating polyalcohol, adding diisocyanate and dibutyltin dilaurate, and reacting at 60-70 deg.C under-0.1 Mpa for 30-40min to obtain solution A;
(2) adding physical modifier into the solution A, and reacting at 90-95 deg.C under-0.1 Mpa for 3-40 min; obtaining a pre-polymerization solution;
(3) and adding trimethylolpropane and methyltriethoxysilane into the prepolymerization liquid, and then heating to 100-110 ℃ for continuing to react for 40-50min to obtain the mixed antibacterial polyurethane.
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| GB1369942A (en) * | 1971-11-03 | 1974-10-09 | Colgate Palmolive Co | Antibacterial biguanide salts |
| JP2001213930A (en) * | 2000-01-31 | 2001-08-07 | Nippon Polyurethane Ind Co Ltd | Antifungal polyurethane resin composition and manufacturing method |
| CN104193950B (en) * | 2014-07-30 | 2016-06-29 | 东莞市吉鑫高分子科技有限公司 | A kind of nano-antibacterial urethane composition and preparation method thereof |
| CN105601511A (en) * | 2015-12-22 | 2016-05-25 | 成都东电艾尔科技有限公司 | Synthetic method for antibacterial disinfection liquid medicine-phenyl salicylate |
| CN106010191A (en) * | 2016-06-30 | 2016-10-12 | 刘世超 | Flame-retardant antibacterial polyurethane coating and preparation method thereof |
| CN106189790A (en) * | 2016-08-08 | 2016-12-07 | 李爱冰 | A kind of waterproof antistatic aqueous polyurethane coating and preparation method thereof |
| CN107501503B (en) * | 2017-08-28 | 2020-11-24 | 南京邦鼎生物科技有限公司 | Composition for preparing antibacterial polyurethane, antibacterial polyurethane and preparation method thereof |
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