CN108384022B - Preparation of hyperbranched resin for improving high-temperature resistance of non-cured rubber asphalt - Google Patents
Preparation of hyperbranched resin for improving high-temperature resistance of non-cured rubber asphalt Download PDFInfo
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- CN108384022B CN108384022B CN201810222771.3A CN201810222771A CN108384022B CN 108384022 B CN108384022 B CN 108384022B CN 201810222771 A CN201810222771 A CN 201810222771A CN 108384022 B CN108384022 B CN 108384022B
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- rubber asphalt
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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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
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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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
- C08G83/006—After treatment of hyperbranched macromolecules
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D195/00—Coating compositions based on bituminous materials, e.g. asphalt, tar, pitch
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/18—Fireproof paints including high temperature resistant paints
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
Abstract
The invention relates to the field of non-cured rubber asphalt waterproof coatings, in particular to a preparation method of hyperbranched resin for improving high-temperature resistance of a non-cured rubber asphalt waterproof coating. Firstly, an isocyanate-terminated hyperbranched polymer is synthesized, and then amino is introduced into the tail end of the hyperbranched resin through amino silicone oil modification, so that an amino-terminated hyperbranched resin is synthesized. The amino-terminated hyperbranched resin is applied to the field of non-cured rubber asphalt waterproof paint, can well improve the high-temperature resistance of the non-cured rubber asphalt waterproof paint, has simple and convenient synthesis process, is easy to industrialize, and is a non-cured rubber asphalt waterproof paint modifier with excellent performance.
Description
Technical Field
The invention relates to the technical field of non-cured rubber asphalt waterproof coatings, in particular to hyperbranched resin for improving the high-temperature resistance of a non-cured rubber asphalt waterproof coating, and a preparation method thereof.
Background
The non-cured rubber asphalt waterproof paint is a polymer modified asphalt waterproof paint with high solid content. The adhesive has the characteristics of long-term non-curing, strong self-healing capability, difficult peeling, good low-temperature bonding performance and the like. The problems of cracking of the waterproof layer and the like caused by stress change of the base layer can be solved. Meanwhile, the waterproof coating can be used as a bottom layer adhesive coating to be matched with waterproof coiled materials to form a composite waterproof layer, and the waterproof layer can solve the problem of water leakage which is difficult to solve by using the waterproof coiled materials alone.
The main components of the traditional non-curing rubber asphalt waterproof coating are prepared from asphalt, rubber, a softener, a tackifier, a stabilizer, a filler and the like. In order to facilitate construction, the traditional non-cured rubber asphalt waterproof coating is generally designed to have larger flowability at high temperature, which easily causes the problems of poor heat resistance of the product, easy sliding and flowing at high temperature and the like.
The invention aims to introduce hyperbranched resin containing a large amount of amino-terminated siloxane, so that the non-cured rubber asphalt waterproof coating and the hyperbranched resin are subjected to chemical crosslinking, and the high temperature resistance of the non-cured rubber asphalt waterproof coating is improved.
The hyperbranched polymer has a three-dimensional network structure, a plurality of active sites, low viscosity, good fusion with a matrix and wide application prospect, and shows great application value in the fields of photoelectric materials, coatings, adhesives, nanotechnology, drug delivery and the like.
Disclosure of Invention
In order to solve the problems of poor heat resistance, easy sliding and flowing at high temperature and the like of the non-cured rubber asphalt waterproof coating, the invention provides the amino-terminated hyperbranched resin for improving the heat resistance of the non-cured rubber asphalt waterproof coating.
The invention also provides a preparation method of the amino-terminated hyperbranched resin.
The invention is realized by the following measures:
the application of the amino-terminated hyperbranched resin in improving the heat resistance of the non-cured rubber asphalt waterproof coating is characterized in that the amino-terminated hyperbranched resin is obtained through the following steps:
uniformly mixing polyol and 2, 2-dimethylolpropionic acid with the mole number of 3-4.5 times of that of the polyol, heating to 140-170 ℃ under the protection of nitrogen, and reacting for 1.5-2h at normal pressure; then adding isocyanate and triethanolamine, heating to 60-70 ℃ under the protection of nitrogen, and reacting for 4 hours; then the terminal amino silicone oil was added and stirred at room temperature for 3 h.
The polyalcohol is trihydric alcohol or tetrahydric alcohol.
The trihydric alcohol is one or more than two of trimethylolpropane, glycerol, butanetriol and triethanolamine.
The tetrahydric alcohol is pentaerythritol.
The isocyanate is one or more than two of 2, 4-toluene diisocyanate, 4-diphenylmethane diisocyanate and isophorone diisocyanate.
The hyperbranched resin of isocyanate with different generations comprises the following components, wherein the charging molar ratio of the first generation polyol, the second generation polyol, the third generation polyol and the fourth generation polyol to the isocyanate is 1: 6-8, 1: 18-24, 1: 42-56 and 1: 90-120.
The hyperbranched resin containing isocyanate at different generations comprises the following components, wherein the feeding molar ratio of the first generation polyol, the second generation polyol, the third generation polyol and the fourth generation polyol to triethanolamine is 1:0, 1: 6-8, 1: 18-24 and 1: 42-56.
The hyperbranched resin of the terminal isocyanate with different generations comprises the polyols of the first generation, the second generation, the third generation and the fourth generation and the terminal isocyanate with the molar ratio of 1: 6-8, 1: 12-16, 1: 24-32 and 1: 48-64.
The hyperbranched resin of different generation numbers of terminal isocyanate, as exemplified by the second generation, may be, but is not limited to, represented by the following formula:
the weight average molecular weight of the amino-terminated silicone oil is 300-1000, and the amino-terminated silicone oil contains 0.1-2 w% of amino.
The mol ratio of the amino-terminated silicone oil to the terminal isocyanate is 1: 1.
The amino-terminated silicone oil is one or more than two of Dow Corning CM-226, Dow Corning OFX-8040A and Dow Corning OFX-8803.
Compared with the prior art, the amino-terminated hyperbranched resin for improving the high-temperature resistance of the non-cured rubber asphalt prepared by the method has the following advantages:
firstly, polyol and 2, 2-dimethylolpropionic acid are reacted to prepare a hydroxyl-terminated central core, then isocyanate is introduced to react with hydroxyl, and triethanolamine is introduced to increase branched chains to form a hyperbranched polymer of polyisocyanate, so that a large number of active groups are provided for the access of amino silicone oil.
Meanwhile, the introduction of siloxane is also beneficial to improving the heat resistance and flexibility of the resin; a large amount of amino in the amino-terminated hyperbranched resin can be crosslinked with ester groups and other groups in the asphalt to form a net structure so as to improve the high-temperature resistance of the non-cured rubber asphalt waterproof coating.
The invention has the beneficial effects that:
the resin prepared by the invention adopts a hyperbranched structure, the preparation method is simple, the raw materials are easy to obtain, and the tail end contains a large amount of active functional groups, so that the material feeding amount can be reduced, and the cost is reduced; meanwhile, the high temperature resistance of the non-cured rubber asphalt waterproof coating is greatly improved, and the non-cured rubber asphalt waterproof coating is blended and stirred uniformly without adding extra process flow, so that the cost is favorably controlled.
Detailed Description
The following is a more detailed description of the embodiments of the present invention, which is intended to illustrate the concepts and features of the invention, and not to limit the scope of the invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Implementation method one
(1) Weighing 13.60g (0.1 mol) of pentaerythritol and 53.65g (0.4 mol) of 2, 2-dimethylolpropionic acid, firstly adding the pentaerythritol and the 2, 2-dimethylolpropionic acid into a four-neck flask with a magnetic stirrer, then adding a proper amount of N, N-dimethylformamide for dissolving, then adding 0.80g of p-toluenesulfonic acid, heating to 140 ℃, and reacting for 1.5h under normal pressure; cooling to 65 ℃, then adding 139.20g (0.8 mol) of 2, 4-toluene diisocyanate, and reacting for 4h under the catalysis of dibutyltin dilaurate and the protection of nitrogen; and (3) slowly adding 240.00g of amino silicone oil at room temperature, and reacting for 3h to obtain the amino-terminated hyperbranched resin.
(2) Adding a certain amount of non-cured rubber asphalt waterproof paint into a crucible, heating and melting, adding the amino-terminated hyperbranched resin obtained in the first step with the mass fraction accounting for 5% of the non-cured rubber asphalt waterproof paint into the crucible, then uniformly stirring at the temperature of 150 ℃, then coating the amino-terminated hyperbranched resin on an aluminum plate with the length, width and thickness of 100mm x 50mm x 2mm, cooling for 24h, then treating for 2h +/-15 min in a baking oven forming an angle of 45 degrees with the horizontal plane, and recording the temperature of firstly occurring sliding, flowing and dripping.
Implementation method two
(1) Weighing 13.60g (0.1 mol) of pentaerythritol and 53.65g (0.4 mol) of 2, 2-dimethylolpropionic acid, firstly adding the pentaerythritol and the 2, 2-dimethylolpropionic acid into a four-neck flask with a magnetic stirrer, then adding a proper amount of N, N-dimethylformamide for dissolving, then adding 0.80g of p-toluenesulfonic acid, heating to 140 ℃, and reacting for 1.5h under normal pressure; cooling to 65 ℃, then adding 139.20g (0.8 mol) of 2, 4-toluene diisocyanate, and reacting for 4h under the catalysis of dibutyltin dilaurate and the protection of nitrogen; 119.20g (0.8 mol) of triethanolamine is added for reaction for 4 hours, 278.40g (1.6 mol) of 2, 4-toluene diisocyanate is added for reaction for 4 hours; and (3) slowly adding 480.00g of amino silicone oil at room temperature, and reacting for 3 hours to obtain the amino-terminated hyperbranched resin.
(2) Adding a certain amount of non-cured rubber asphalt waterproof paint into a crucible, heating and melting, adding the amino-terminated hyperbranched resin obtained in the first step with the mass fraction accounting for 5% of the non-cured rubber asphalt waterproof paint into the crucible, then uniformly stirring at the temperature of 150 ℃, then coating the amino-terminated hyperbranched resin on an aluminum plate with the length, width and thickness of 100mm x 50mm x 2mm, cooling for 24h, then treating for 2h +/-15 min in a baking oven forming an angle of 45 degrees with the horizontal plane, and recording the temperature of firstly occurring sliding, flowing and dripping.
Implementation method three
(1) Weighing 13.60g (0.1 mol) of pentaerythritol and 53.65g (0.4 mol) of 2, 2-dimethylolpropionic acid, firstly adding the pentaerythritol and the 2, 2-dimethylolpropionic acid into a four-neck flask with a magnetic stirrer, then adding a proper amount of N, N-dimethylformamide for dissolving, then adding 0.80g of p-toluenesulfonic acid, heating to 140 ℃, and reacting for 1.5h under normal pressure; cooling to 65 ℃, then adding 139.20g (0.8 mol) of 2, 4-toluene diisocyanate, and reacting for 4h under the catalysis of dibutyltin dilaurate and the protection of nitrogen; 119.20g (0.8 mol) of triethanolamine is added for reaction for 4 hours, 278.40g (1.6 mol) of 2, 4-toluene diisocyanate is added for reaction for 4 hours; and (3) slowly adding 480.00g of amino silicone oil at room temperature, and reacting for 3 hours to obtain the amino-terminated hyperbranched resin.
(2) Adding a certain amount of non-cured rubber asphalt waterproof paint into a crucible, heating and melting, adding the amino-terminated hyperbranched resin obtained in the first step with the mass fraction accounting for 10% of the non-cured rubber asphalt waterproof paint into the crucible, then uniformly stirring at the temperature of 150 ℃, then coating the amino-terminated hyperbranched resin on an aluminum plate with the length, width and thickness of 100mm x 50mm x 2mm, cooling for 24h, then treating for 2h +/-15 min in a baking oven forming an angle of 45 degrees with the horizontal plane, and recording the temperature of firstly occurring sliding, flowing and dripping.
Implementation method four
(1) Weighing 13.60g (0.1 mol) of pentaerythritol and 53.65g (0.4 mol) of 2, 2-dimethylolpropionic acid, firstly adding the pentaerythritol and the 2, 2-dimethylolpropionic acid into a four-neck flask with a magnetic stirrer, then adding a proper amount of N, N-dimethylformamide for dissolving, then adding 0.80g of p-toluenesulfonic acid, heating to 140 ℃, and reacting for 1.5h under normal pressure; cooling to 65 ℃, then adding 139.20g (0.8 mol) of 2, 4-toluene diisocyanate, and reacting for 4h under the catalysis of dibutyltin dilaurate and the protection of nitrogen; 119.20g (0.8 mol) of triethanolamine is added for reaction for 4 hours, 278.40g (1.6 mol) of 2, 4-toluene diisocyanate is added for reaction for 4 hours; and (3) slowly adding 480.00g of amino silicone oil at room temperature, and reacting for 3 hours to obtain the amino-terminated hyperbranched resin.
(2) Adding a certain amount of non-cured rubber asphalt waterproof paint into a crucible, heating and melting, adding the amino-terminated hyperbranched resin obtained in the first step with the mass fraction accounting for 15% of the non-cured rubber asphalt waterproof paint into the crucible, then uniformly stirring at the temperature of 150 ℃, then coating the amino-terminated hyperbranched resin on an aluminum plate with the length, width and thickness of 100mm x 50mm x 2mm, cooling for 24h, then treating for 2h +/-15 min in a baking oven forming an angle of 45 degrees with the horizontal plane, and recording the temperature of firstly occurring sliding, flowing and dripping.
Comparative example
Adding a certain amount of non-solidified rubber asphalt waterproof coating into a crucible, heating and melting, then coating the non-solidified rubber asphalt waterproof coating on an aluminum plate with the length, width and thickness of 100mm x 50mm x 2mm, cooling for 24h, then treating for 2h +/-15 min in a baking oven forming an angle of 45 degrees with the horizontal plane, and recording the temperature of the most existing sliding, flowing and dripping.
Performance testing
In order to illustrate the practical effects of the present invention, the hyperbranched resin obtained by the method of the present invention is added to the non-cured rubber asphalt waterproof coating for high temperature resistance test.
The test properties are given in table 1 below.
TABLE 1 dripping temperature of non-curing rubber asphalt waterproof coating
| Hyperbranched resin | Flow temperature/. degree.C |
| Comparative example | 71 |
| Implementation method one (5%) | 83 |
| EXAMPLE No. two (5%) | 85 |
| EXAMPLE III (10%) | 100 |
| EXAMPLE IV (15%) | 117 |
As can be seen from Table 1, the non-cured rubber asphalt waterproof coating prepared by adding the amino-terminated hyperbranched resin prepared by the invention has obviously improved high temperature resistance compared with that without adding the hyperbranched resin. Wherein when the addition amount is 5%, the second generation hyperbranched resin is slightly better than the first generation hyperbranched resin; along with the increase of the addition amount of the second generation hyperbranched resin, the high temperature resistance of the non-cured rubber asphalt waterproof coating is greatly improved.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the embodiments, and any other changes, modifications, combinations, substitutions and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents and are included in the scope of the present invention.
Claims (3)
1. The preparation method of the hyperbranched resin for improving the high-temperature resistance of the non-cured rubber asphalt is characterized in that the hyperbranched resin is obtained by the following steps:
uniformly mixing polyol and 2, 2-dimethylolpropionic acid with the mole number of 3-4.5 times of that of the polyol, heating to 140-170 ℃ under the protection of nitrogen, reacting for 1.5-2h under normal pressure, adding isocyanate and triethanolamine, heating to 60-70 ℃ under the protection of nitrogen, and reacting for 4 h; then the terminal amino silicone oil was added and stirred at room temperature for 3 h.
2. The method according to claim 1, wherein the polyhydric alcohol is one or more of trimethylolpropane, glycerol, butanetriol, triethanolamine, and pentaerythritol.
3. The method according to claim 1, wherein the isocyanate is one or more selected from the group consisting of 2, 4-tolylene diisocyanate, 4-diphenylmethane diisocyanate, and isophorone diisocyanate.
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| CN109161009B (en) * | 2018-09-04 | 2020-12-11 | 济南大学 | Preparation and application of hyperbranched organic silicon polymer |
| CN109824909B (en) * | 2019-02-27 | 2020-10-27 | 济南大学 | Preparation and application of organic silicon modified hyperbranched polyester-amide resin |
| CN111548734A (en) * | 2020-05-27 | 2020-08-18 | 潍坊石花化工建材有限公司 | Normal-temperature construction type non-cured rubber asphalt waterproof coating and preparation method thereof |
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Effective date of registration: 20210114 Address after: 014300 south of Weiliu Road and east of Donghan cashmere industry park, sanlongliang Industrial Park, Dalate Economic Development Zone, Ordos City, Inner Mongolia Autonomous Region Patentee after: Inner Mongolia ante Weidun Waterproof Technology Co.,Ltd. Address before: 250022 No. 336, South Xin Zhuang West Road, Shizhong District, Ji'nan, Shandong Patentee before: University of Jinan |
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