CN110698641A - Preparation method of polyurethane acrylate nonlinear optical material - Google Patents
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- CN110698641A CN110698641A CN201911021353.9A CN201911021353A CN110698641A CN 110698641 A CN110698641 A CN 110698641A CN 201911021353 A CN201911021353 A CN 201911021353A CN 110698641 A CN110698641 A CN 110698641A
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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
- C08G18/70—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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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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
- C08G18/4833—Polyethers containing oxyethylene units
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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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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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
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/23—Azo-compounds
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention provides a preparation method of a polyurethane acrylate nonlinear optical material, which comprises the following steps: adding polyether polyol and diisocyanate into a flask, reacting for 10-50min at 18-25 ℃, adding a catalyst for reacting for 20-50min, then adding acrylate containing hydroxyl, azo compound and initiator for continuing to react for 0.5-1h, vacuumizing for 1-3h at 20 ℃, pouring into a mold, and putting the mold into an oven for step temperature programming to obtain the polyurethane acrylate nonlinear optical material. The polyurethane acrylate nonlinear optical material prepared by the invention has high linear light transmittance and use temperature, fast light response and excellent light amplitude limiting performance. It can be applied to optical materials, bulletproof glass, optical switches, laser protection materials and the like.
Description
Technical Field
The invention relates to the field of materials, in particular to a preparation method of a polyurethane acrylate nonlinear optical material.
Background
The azo compound has better optical nonlinearity, but is not easy to be processed into devices, so that the application range is limited, the azo compound is added into thermoplastic polymers such as polymethyl methacrylate or polystyrene, and the like, so that the polymer-based nonlinear optical material can be prepared, but the thermoplastic polymers have poor heat resistance, so that the application of the thermoplastic polymers at high temperature is limited to a certain extent.
The polyurethane acrylate is a polymer with a main chain containing a characteristic unit of carbamate, and the thermosetting polyurethane acrylate with different mechanical properties can be prepared by adjusting the proportion of a hard segment and a soft segment. In view of the advantages of excellent nonlinear performance of azo compounds, easy processability of urethane acrylate and the like, if the azo compounds are introduced into a urethane acrylate system, nonlinear optical elements are fixed in a polyurethane grid, the dissociation and precipitation of the nonlinear elements are limited, a novel thermosetting polyurethane-based nonlinear optical material is obtained, and the application range of the urethane acrylate is further expanded. Meanwhile, the polyurethane acrylate also provides a good dispersed and stable chemical environment and a higher use temperature for the nonlinear element, and a novel polyurethane acrylate nonlinear optical material with potential application value is obtained.
Disclosure of Invention
The invention provides a preparation method of a polyurethane acrylate nonlinear optical material, which is characterized in that an azo compound is introduced into a polyurethane acrylate system, a nonlinear optical element is fixed in a polyurethane grid, the dissociation and precipitation of the nonlinear element are limited, and a novel thermosetting polyurethane-based nonlinear optical material is obtained.
The technical scheme for realizing the invention is as follows:
a preparation method of a polyurethane acrylate nonlinear optical material comprises the following steps:
adding polyether polyol and diisocyanate into a flask, reacting for 10-50min at 18-25 ℃, adding a catalyst for reacting for 20-50min, then adding acrylate containing hydroxyl, azo compound and initiator for continuing to react for 0.5-1h, vacuumizing for 1-3h at 20 ℃, pouring into a mold, and putting the mold into an oven for step temperature programming to obtain the polyurethane acrylate nonlinear optical material.
The polyether polyol is any one of polyethylene glycol, polypropylene glycol and polytetrahydrofuran.
The diisocyanate is isophorone diisocyanate.
The catalyst is any one of dibutyltin dilaurate, stannous octoate and dibutyltin dichloride.
The acrylate containing hydroxyl is beta-hydroxyethyl methacrylate or beta-hydroxypropyl methacrylate.
The azo compound is any one of methyl orange, congo red or 4-amino-4' -p-dimethylamino azobenzene.
The initiator is a peroxide initiator or an azo initiator.
The mass ratio of the polyether glycol, the diisocyanate and the hydroxyl-containing acrylate is 1:2:2, the amount of the initiator is 1-3% of the total mass of the polyether glycol, the diisocyanate and the hydroxyl-containing acrylate, the amount of the catalyst is 0.1-0.3% of the total mass of the polyether glycol, the diisocyanate and the hydroxyl-containing acrylate, and the amount of the azo compound is 0.01-5% of the total mass of the polyether glycol, the diisocyanate and the hydroxyl-containing acrylate.
The step temperature programming in the step (2) comprises the steps of keeping the temperature at 30 ℃ for 1-2h, keeping the temperature at 40 ℃ for 1-2h, keeping the temperature at 50 ℃ for 1-2h, keeping the temperature at 60 ℃ for 1-2h and keeping the temperature at 70 ℃ for 24-48 h.
The invention has the beneficial effects that: the polyurethane acrylate is a thermosetting polymer material with good processability and high transparency, is insoluble and infusible, can adjust the size of a polyurethane grid by changing the molecular weight of polyether polyol, is more beneficial to fixing azo compounds with different molecular sizes, is beneficial to uniformly dispersing the azo compounds in a polymer, and limits the dissociation and precipitation of the azo compounds. The polyurethane acrylate nonlinear optical material prepared by the invention has high linear light transmittance and use temperature, fast light response and excellent light amplitude limiting performance. It can be applied to optical materials, bulletproof glass, optical switches, laser protection materials and the like.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a plot of the nonlinear absorption measured by picosecond z-scan for the urethane acrylate nonlinear optical material of example 1;
FIG. 2 is a plot of the nonlinear absorption measured by picosecond z-scan for the urethane acrylate nonlinear optical material of example 2;
FIG. 3 is a plot of the nonlinear absorption measured by picosecond z-scan for the urethane acrylate nonlinear optical material of example 3.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without inventive effort based on the embodiments of the present invention, are within the scope of the present invention.
Example 1
A preparation method of a polyurethane acrylate nonlinear optical material comprises the following steps:
adding 18g of polyethylene glycol 600 and 13.34g of isophorone diisocyanate into a flask, reacting for 10min at 20 ℃, adding 37uL of dibutyltin dilaurate, reacting for 30min, adding 35.2mg of methyl orange, 0.1174g of azobisisobutyronitrile and 7.81g of beta-hydroxyethyl methacrylate, continuing to react for 40min, vacuumizing for 2h at 20 ℃, pouring into a mold, putting the mold into an oven, and carrying out temperature rise sequentially, wherein the temperature rise is constant at 30 ℃ for 1h, the temperature rise is constant at 40 ℃ for 1h, the temperature rise at 50 ℃ for 1h, the temperature rise at 60 ℃ for 1h, and the temperature rise at 70 ℃ for 24h to obtain the polyurethane acrylate nonlinear optical material.
Example 2
A preparation method of a polyurethane acrylate nonlinear optical material comprises the following steps:
adding 12g of polyethylene glycol 400 and 13.34g of isophorone diisocyanate into a flask, reacting for 15min at 22 ℃, adding 37uL of dibutyltin dilaurate, reacting for 30min, adding 29.8mg of congo red, 0.1174g of azobisisobutyronitrile and 7.81g of beta-hydroxyethyl methacrylate, continuing to react for 50min, vacuumizing for 3h at 20 ℃, pouring into a mold, putting the mold into an oven, and carrying out temperature rise sequentially, wherein the temperature rise is constant at 30 ℃ for 1.5h, the temperature rise is constant at 40 ℃ for 1.5h, the temperature rise is constant at 50 ℃ for 1.5h, the temperature rise is constant at 60 ℃ for 1.5h, and the temperature rise is constant at 70 ℃ for 24h to obtain the polyurethane acrylate nonlinear optical material.
Example 3
A preparation method of a polyurethane acrylate nonlinear optical material comprises the following steps:
adding 36g of polyethylene glycol 600 and 26.68g of isophorone diisocyanate into a flask, reacting for 20min at 22 ℃, adding 74uL (0.1 mg) of dibutyltin dichloride, then reacting for 40min, adding 70.5mg of 4-amino-4' -p-dimethylaminoazobenzene, 0.2348g of dibenzoyl peroxide and 15.62g of beta-hydroxyethyl methacrylate, continuing to react for 50min, vacuumizing for 1.5h at 20 ℃, pouring into a mold, putting the mold into an oven, and sequentially heating, wherein the temperature is kept at 30 ℃ for 2h, the temperature is kept at 40 ℃ for 2h, the temperature is kept at 50 ℃ for 2h, the temperature is kept at 60 ℃ for 2h, and the temperature is kept at 70 ℃ for 48h to obtain the polyurethane acrylate nonlinear optical material.
Example 4
A preparation method of a polyurethane acrylate nonlinear optical material comprises the following steps:
0.01mol of polyethylene glycol 600 and 0.02mol of isophorone diisocyanate were added to the flask, reacting at 18 ℃ for 10min, adding dibutyltin dichloride, then reacting for 20min, and adding 4-amino-4 '-p-dimethylaminoazobenzene, dibenzoyl peroxide and beta-hydroxypropyl methacrylate, wherein the amount of the dibenzoyl peroxide is 1 percent of the total mass of the polyethylene glycol 600, the isophorone diisocyanate and the beta-hydroxypropyl methacrylate, the amount of the dibutyltin dichloride is 0.1 percent of the total mass of the polyethylene glycol 600, the isophorone diisocyanate and the beta-hydroxypropyl methacrylate, and the amount of the 4-amino-4' -p-dimethylaminoazobenzene is 0.01 percent of the total mass of the polyethylene glycol 600, the isophorone diisocyanate and the beta-hydroxypropyl methacrylate. And continuously reacting for 60min, vacuumizing for 3h at 20 ℃, pouring into a mold, putting the mold into an oven, and carrying out temperature rise sequentially for 2h at the constant temperature of 30 ℃, 2h at the constant temperature of 40 ℃, 2h at the constant temperature of 50 ℃, 2h at the constant temperature of 60 ℃ and 48h at the constant temperature of 70 ℃ to obtain the polyurethane acrylate nonlinear optical material.
Example 5
A preparation method of a polyurethane acrylate nonlinear optical material comprises the following steps:
0.01mol of polypropylene glycol 400 and 0.02mol of isophorone diisocyanate are added into a flask, the mixture is reacted for 50min at 25 ℃, stannous octoate is added, the reaction is carried out for 50min, 4-amino-4 '-p-dimethylamino azobenzene, dibenzoyl peroxide and beta-hydroxypropyl methacrylate are added, the amount of dibenzoyl peroxide is 3 percent of the total mass of the polypropylene glycol 400, the isophorone diisocyanate and the stannous octoate, the amount of dibutyl tin dichloride is 0.3 percent of the total mass of the polypropylene glycol 400, the isophorone diisocyanate and the stannous octoate, and the amount of 4-amino-4' -p-dimethylamino azobenzene is 5 percent of the total mass of the polypropylene glycol 400, the isophorone diisocyanate and the stannous octoate. And continuously reacting for 30min, vacuumizing for 1h at the temperature of 20 ℃, pouring into a mold, putting the mold into an oven, and carrying out temperature rise sequentially for 2h at the constant temperature of 30 ℃, 2h at the constant temperature of 40 ℃, 2h at the constant temperature of 50 ℃, 2h at the constant temperature of 60 ℃ and 48h at the constant temperature of 70 ℃ to obtain the polyurethane acrylate nonlinear optical material.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (9)
1. A preparation method of a polyurethane acrylate nonlinear optical material is characterized by comprising the following steps:
adding polyether polyol and diisocyanate into a flask, reacting for 10-50min at 18-25 ℃, adding a catalyst for reacting for 20-50min, then adding acrylate containing hydroxyl, azo compound and initiator for continuing to react for 0.5-1h, vacuumizing for 1-3h at 20 ℃, pouring into a mold, and putting the mold into an oven for step temperature programming to obtain the polyurethane acrylate nonlinear optical material.
2. The method for preparing the urethane acrylate nonlinear optical material according to claim 1, characterized in that: the polyether polyol is any one of polyethylene glycol, polypropylene glycol and polytetrahydrofuran.
3. The method for preparing the urethane acrylate nonlinear optical material according to claim 1, characterized in that: the diisocyanate is isophorone diisocyanate.
4. The method for preparing the urethane acrylate nonlinear optical material according to claim 1, characterized in that: the catalyst is any one of dibutyltin dilaurate, stannous octoate and dibutyltin dichloride.
5. The method for preparing the urethane acrylate nonlinear optical material according to claim 1, characterized in that: the acrylate containing hydroxyl is beta-hydroxyethyl methacrylate or beta-hydroxypropyl methacrylate.
6. The method for preparing the urethane acrylate nonlinear optical material according to claim 1, characterized in that: the azo compound is any one of methyl orange, congo red or 4-amino-4' -p-dimethylamino azobenzene.
7. The method for preparing the urethane acrylate nonlinear optical material according to claim 1, characterized in that: the initiator is a peroxide initiator or an azo initiator.
8. The method for preparing a urethane acrylate nonlinear optical material according to any one of claims 1 to 7, characterized in that: the mass ratio of the polyether glycol, the diisocyanate and the hydroxyl-containing acrylate is 1:2:2, the amount of the initiator is 1-3% of the total mass of the polyether glycol, the diisocyanate and the hydroxyl-containing acrylate, the amount of the catalyst is 0.1-0.3% of the total mass of the polyether glycol, the diisocyanate and the hydroxyl-containing acrylate, and the amount of the azo compound is 0.01-5% of the total mass of the polyether glycol, the diisocyanate and the hydroxyl-containing acrylate.
9. The method for preparing the nonlinear optical urethane acrylate material according to claim 8, wherein the method comprises the following steps: the step temperature programming step comprises the steps of keeping the temperature of 30 ℃ for 1-2h, keeping the temperature of 40 ℃ for 1-2h, keeping the temperature of 50 ℃ for 1-2h, keeping the temperature of 60 ℃ for 1-2h, and keeping the temperature of 70 ℃ for 24-48 h.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111875765A (en) * | 2020-07-16 | 2020-11-03 | 复旦大学 | Linear azobenzene polymer containing hydrogen bond and preparation method and application thereof |
| CN113388086A (en) * | 2021-06-30 | 2021-09-14 | 郑州轻工业大学 | Bonding type polyurethane nonlinear optical material and preparation method and application thereof |
| CN114316203A (en) * | 2021-12-21 | 2022-04-12 | 郑州轻工业大学 | Polyurethane acrylate photocuring resin material, preparation method thereof and preparation method of polyurethane acrylate prepolymer |
| CN114560987A (en) * | 2022-03-14 | 2022-05-31 | 郑州轻工业大学 | Bonding type nonlinear polyurethane acrylate photocuring material and preparation method and application thereof |
| CN114634704A (en) * | 2022-03-14 | 2022-06-17 | 郑州轻工业大学 | Doped non-linear polyurethane acrylate photocuring material and preparation method and application thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111875765A (en) * | 2020-07-16 | 2020-11-03 | 复旦大学 | Linear azobenzene polymer containing hydrogen bond and preparation method and application thereof |
| CN113388086A (en) * | 2021-06-30 | 2021-09-14 | 郑州轻工业大学 | Bonding type polyurethane nonlinear optical material and preparation method and application thereof |
| CN113388086B (en) * | 2021-06-30 | 2022-06-03 | 郑州轻工业大学 | Bonding type polyurethane nonlinear optical material and preparation method and application thereof |
| CN114316203A (en) * | 2021-12-21 | 2022-04-12 | 郑州轻工业大学 | Polyurethane acrylate photocuring resin material, preparation method thereof and preparation method of polyurethane acrylate prepolymer |
| CN114560987A (en) * | 2022-03-14 | 2022-05-31 | 郑州轻工业大学 | Bonding type nonlinear polyurethane acrylate photocuring material and preparation method and application thereof |
| CN114634704A (en) * | 2022-03-14 | 2022-06-17 | 郑州轻工业大学 | Doped non-linear polyurethane acrylate photocuring material and preparation method and application thereof |
| CN114634704B (en) * | 2022-03-14 | 2023-12-19 | 郑州轻工业大学 | Doped nonlinear polyurethane acrylate photo-curing material, and preparation method and application thereof |
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