CN105504216A - Preparation method of rosin-based waterborne polyurethane waterproof material - Google Patents
Preparation method of rosin-based waterborne polyurethane waterproof material Download PDFInfo
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- CN105504216A CN105504216A CN201510962955.XA CN201510962955A CN105504216A CN 105504216 A CN105504216 A CN 105504216A CN 201510962955 A CN201510962955 A CN 201510962955A CN 105504216 A CN105504216 A CN 105504216A
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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
- C08G18/68—Unsaturated polyesters
- C08G18/683—Unsaturated polyesters containing cyclic groups
- C08G18/686—Unsaturated polyesters containing cyclic groups containing cycloaliphatic groups
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
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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
- C08G18/4825—Polyethers containing two hydroxy groups
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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
- C08G18/65—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
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
-
- 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
- C08G2150/00—Compositions for coatings
- C08G2150/90—Compositions for anticorrosive coatings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a preparation method of a rosin-based waterborne polyurethane waterproof material. Maleopimaric acid which is a modified product of rosin is adopted as a raw material to synthesize maleic rosin polyester polyol, and then maleic rosin polyester polyol is reacted with organic isocyanate, polyethylene glycol, dimethylolpropionic acid, acetone and triethylamine to obtain polyurethane dispersoid; in the use process, polyurethane dispersoid and tripoly(hexamethylene diisocyanate) are mixed evenly according to a certain proportion. Raw materials are wide in source and easy to obtain, the synthetic process is simple, and the preparation method is especially suitable for industrial production; by introducing rosin-based polyester polyol, the hardness and corrosion resistance of a paint film are improved, and the heat resistance of the paint film is significantly improved.
Description
Technical field
The present invention relates to architectural waterproof material field, be specifically related to a kind of preparation method of rosin based aqueous polyurethanes water-proof material.
Background technology
Polyurethane coating molecular structure contains a large amount of amino-formate bonds, also comprise the structures such as urea key, ester bond and biuret linkage, the paint film that therefore polyurethane coating is formed just shows excellent snappiness, wear resistance, chemical-resistant reagent corrodibility and the performance such as low temperature resistant.Wherein aqueous polyurethane coating take water as main medium, containing less organic solvent or not containing organic solvent, thus reduces organic volatile quantity discharged, becomes the representative of Environmentally friendly coatings development, receive the extensive concern of people.
Polyvalent alcohol is one of very important raw material in synthesis of polyurethane, comprises polyester type and polyether-type two kinds.The raw material of current production polyester polyol based on petrochemicals, and mostly is the poisonous and hazardous chemical such as phthalic anhydride, phthalic acid.Along with manifesting gradually of energy dilemma, the continuous rising of oil price, the price of polyester, polyether glycol also increases fast.Therefore, utilize the urethane intermediates that natural reproducible resource is raw material production, its cost and sustainability advantage start to manifest.
Summary of the invention
The object of this invention is to provide a kind of preparation method of rosin based aqueous polyurethanes water-proof material, by adopting the Abietyl modified product maleopimaric acid of abundance as Material synthesis maleated rosin polyester polyol, further synthesis obtains aqueous polyurethane water-proof material, raw material sources extensively, easily obtain, synthesis technique is simple, is particularly suitable for industrialization and produces.
In order to achieve the above object, the technical scheme that the present invention takes is:
A preparation method for rosin based aqueous polyurethanes water-proof material, comprises the following steps:
(1) 35 ~ 45 parts of maleopimaric acids, 8.0 ~ 10.4 parts of toluene are added in the reactor, be warming up to 180 DEG C and add 8.6 ~ 11 parts of MALEIC ANHYDRIDE, 1.2 ~ 1.7 parts of catalyzer and 9.3 ~ 12 parts of glycol ethers, be warming up to 200 DEG C, reacting by heating becomes clarification to toluene from muddiness, after question response terminates, product is poured into water, cooling, washing, oven dry, obtain maleated rosin polyester polyol;
(2) 13.5 ~ 22 parts of polyoxyethylene glycol are added in the reactor, be warming up to 65 DEG C and add 12 ~ 25.2 parts of maleated rosin polyester polyols, 40 ~ 60 parts of organic isocyanates, be warming up to 80 DEG C of reaction to NCO content and reach terminal, be cooled to 70 DEG C, add 0.6 ~ 2 part of catalyzer, 6 ~ 15 parts of dimethylol propionic acids, 4 ~ 12 parts of acetone reaction 4h, be cooled to 40 DEG C, be uniformly dispersed under adding 6 ~ 15 parts of triethylamines, 12 ~ 20 parts of deionized water high-speed stirring, vacuum removing acetone, obtains polyurethane dispersions;
(3) when using, polyurethane dispersions and trimerization hexamethylene diisocyanate are pressed the weight ratio mixing of 1:1.1 ~ 1.3, add appropriate amount of deionized water and regulate emulsion viscosity, stir.
As specializing, described organic isocyanate is the one in isoflurane chalcone diisocyanate, tolylene diisocyanate, diphenylmethanediisocyanate.
As specializing, described maleated rosin polyester polyol consumption is 40 ~ 60% of polyoxyethylene glycol and maleated rosin polyester polyol total amount.
Compared with prior art, the benefit that has of the present invention:
The present invention adopts the modified product maleopimaric acid of rosin as Material synthesis maleated rosin polyester polyol, and synthesis obtains aqueous polyurethane water-proof material further; Raw material sources of the present invention extensively, easily obtain, and synthesis technique is simple, are particularly suitable for industrialization and produce; The introducing of rosinyl polyester polyol improves hardness and the erosion resistance of paint film, is a significant increase the thermotolerance of paint film.
Embodiment
Below in conjunction with specific embodiment, the present invention is further described.
Embodiment 1
(1) synthesis of maleated rosin polyester polyol: add 40g maleopimaric acid in the there-necked flask that mechanical stirring, water trap and spherical condensation tube are housed, 9.2g toluene, at N
2180 DEG C are slowly warming up under protection, treat that maleopimaric acid all dissolves and add 9.8g MALEIC ANHYDRIDE, 1.5g aluminum chloride and 10.6g glycol ether, be warming up to 200 DEG C, in reacting by heating to water trap, toluene becomes clarification from muddiness, after question response terminates, product is poured into water, cooling, by the abundant washing and drying of water, obtains white powder and maleated rosin polyester polyol;
(2) add 16.8g cetomacrogol 1000 in the reactor, be warming up to 65 DEG C and add 25.2g maleated rosin polyester polyol, 50g isoflurane chalcone diisocyanate after cetomacrogol 1000 melts, be warming up to 80 DEG C at N
2lower reaction to the NCO content of protection reaches terminal, be cooled to 70 DEG C, add 1g dibutyl tin laurate, 12g dimethylol propionic acid, 6g acetone reaction 4h, is then cooled to 40 DEG C, is uniformly dispersed under adding 10g triethylamine, 15g deionized water high-speed stirring, vacuum removing acetone, obtains polyurethane dispersions;
(3) when using, polyurethane dispersions and trimerization hexamethylene diisocyanate are pressed the weight ratio mixing of 1:1.2, add appropriate amount of deionized water and regulate emulsion viscosity, stir.
Embodiment 2
(1) synthesis of maleated rosin polyester polyol: add 35g maleopimaric acid in the there-necked flask that mechanical stirring, water trap and spherical condensation tube are housed, 8.0g toluene, at N
2180 DEG C are slowly warming up under protection, treat that maleopimaric acid all dissolves and add 8.6g MALEIC ANHYDRIDE, 1.2g aluminum chloride and 9.3g glycol ether, be warming up to 200 DEG C, in reacting by heating to water trap, toluene becomes clarification from muddiness, after question response terminates, product is poured into water, cooling, by the abundant washing and drying of water, obtains white powder and maleated rosin polyester polyol;
(2) add 22g cetomacrogol 1000 in the reactor, be warming up to 65 DEG C and add 18g maleated rosin polyester polyol, 40g diphenylmethanediisocyanate after cetomacrogol 1000 melts, be warming up to 80 DEG C at N
2lower reaction to the NCO content of protection reaches terminal, be cooled to 70 DEG C, add 0.6g dibutyl tin laurate, 6g dimethylol propionic acid, 4g acetone reaction 4h, is then cooled to 40 DEG C, is uniformly dispersed under adding 6g triethylamine, 12g deionized water high-speed stirring, vacuum removing acetone, obtains polyurethane dispersions;
(3) when using, polyurethane dispersions and trimerization hexamethylene diisocyanate are pressed the weight ratio mixing of 1:1.3, add appropriate amount of deionized water and regulate emulsion viscosity, stir.
Embodiment 3
(1) synthesis of maleated rosin polyester polyol: add 45g maleopimaric acid in the there-necked flask that mechanical stirring, water trap and spherical condensation tube are housed, 10.4g toluene, at N
2180 DEG C are slowly warming up under protection, treat that maleopimaric acid all dissolves and add 11g MALEIC ANHYDRIDE, 1.7g aluminum chloride and 12g glycol ether, be warming up to 200 DEG C, in reacting by heating to water trap, toluene becomes clarification from muddiness, after question response terminates, product is poured into water, cooling, by the abundant washing and drying of water, obtains white powder and maleated rosin polyester polyol;
(2) add 15g cetomacrogol 1000 in the reactor, be warming up to 65 DEG C and add 15g maleated rosin polyester polyol, 45g tolylene diisocyanate after cetomacrogol 1000 melts, be warming up to 80 DEG C at N
2lower reaction to the NCO content of protection reaches terminal, be cooled to 70 DEG C, add 0.8g dibutyl tin laurate, 8g dimethylol propionic acid, 5g acetone reaction 4h, is then cooled to 40 DEG C, is uniformly dispersed under adding 8g triethylamine, 14g deionized water high-speed stirring, vacuum removing acetone, obtains polyurethane dispersions;
(3) when using, polyurethane dispersions and trimerization hexamethylene diisocyanate are pressed the weight ratio mixing of 1:1.25, add appropriate amount of deionized water and regulate emulsion viscosity, stir.
Embodiment 4
(1) synthesis of maleated rosin polyester polyol: add 38g maleopimaric acid in the there-necked flask that mechanical stirring, water trap and spherical condensation tube are housed, 8.7g toluene, at N
2180 DEG C are slowly warming up under protection, treat that maleopimaric acid all dissolves and add 11g MALEIC ANHYDRIDE, 1.4g aluminum chloride and 10g glycol ether, be warming up to 200 DEG C, in reacting by heating to water trap, toluene becomes clarification from muddiness, after question response terminates, product is poured into water, cooling, by the abundant washing and drying of water, obtains white powder and maleated rosin polyester polyol;
(2) add 13.5g cetomacrogol 1000 in the reactor, be warming up to 65 DEG C and add 16.5g maleated rosin polyester polyol, 54g diphenylmethanediisocyanate after cetomacrogol 1000 melts, be warming up to 80 DEG C at N
2lower reaction to the NCO content of protection reaches terminal, be cooled to 70 DEG C, add 1.5g dibutyl tin laurate, 14g dimethylol propionic acid, 9g acetone reaction 4h, is then cooled to 40 DEG C, is uniformly dispersed under adding 12g triethylamine, 16g deionized water high-speed stirring, vacuum removing acetone, obtains polyurethane dispersions;
(3) when using, polyurethane dispersions and trimerization hexamethylene diisocyanate are pressed the weight ratio mixing of 1:1.1, add appropriate amount of deionized water and regulate emulsion viscosity, stir.
Embodiment 5
(1) synthesis of maleated rosin polyester polyol: add 42g maleopimaric acid in the there-necked flask that mechanical stirring, water trap and spherical condensation tube are housed, 9.7g toluene, at N
2180 DEG C are slowly warming up under protection, treat that maleopimaric acid all dissolves and add 10.3g MALEIC ANHYDRIDE, 1.6g aluminum chloride and 11.1g glycol ether, be warming up to 200 DEG C, in reacting by heating to water trap, toluene becomes clarification from muddiness, after question response terminates, product is poured into water, cooling, by the abundant washing and drying of water, obtains white powder and maleated rosin polyester polyol;
(2) add 18g cetomacrogol 1000 in the reactor, be warming up to 65 DEG C and add 12g maleated rosin polyester polyol, 60g isoflurane chalcone diisocyanate after cetomacrogol 1000 melts, be warming up to 80 DEG C at N
2lower reaction to the NCO content of protection reaches terminal, be cooled to 70 DEG C, add 2g dibutyl tin laurate, 15g dimethylol propionic acid, 12g acetone reaction 4h, is then cooled to 40 DEG C, is uniformly dispersed under adding 15g triethylamine, 20g deionized water high-speed stirring, vacuum removing acetone, obtains polyurethane dispersions;
(3) when using, polyurethane dispersions and trimerization hexamethylene diisocyanate are pressed the weight ratio mixing of 1:1.15, add appropriate amount of deionized water and regulate emulsion viscosity, stir.
The performance such as shock strength, tensile stress, elongation at break, sticking power of bi-component water-proof material obtained for embodiment 1,2,3,4,5 tested, result is as shown in table 1 below.
Table 1
The above, it is only present pre-ferred embodiments, not technical scope of the present invention is imposed any restrictions, thus every above embodiment is done according to technical spirit of the present invention any trickle amendment, equivalent variations and modification, all still belong in the scope of technical solution of the present invention.
Claims (3)
1. a preparation method for rosin based aqueous polyurethanes water-proof material, is characterized in that comprising the following steps:
(1) 35 ~ 45 parts of maleopimaric acids, 8.0 ~ 10.4 parts of toluene are added in the reactor, be warming up to 180 DEG C and add 8.6 ~ 11 parts of MALEIC ANHYDRIDE, 1.2 ~ 1.7 parts of catalyzer and 9.3 ~ 12 parts of glycol ethers, be warming up to 200 DEG C, reacting by heating becomes clarification to toluene from muddiness, after question response terminates, product is poured into water, cooling, washing, oven dry, obtain maleated rosin polyester polyol;
(2) 13.5 ~ 22 parts of polyoxyethylene glycol are added in the reactor, be warming up to 65 DEG C and add 12 ~ 25.2 parts of maleated rosin polyester polyols, 40 ~ 60 parts of organic isocyanates, be warming up to 80 DEG C of reaction to NCO content and reach terminal, be cooled to 70 DEG C, add 0.6 ~ 2 part of catalyzer, 6 ~ 15 parts of dimethylol propionic acids, 4 ~ 12 parts of acetone reaction 4h, be cooled to 40 DEG C, be uniformly dispersed under adding 6 ~ 15 parts of triethylamines, 12 ~ 20 parts of deionized water high-speed stirring, vacuum removing acetone, obtains polyurethane dispersions;
(3) when using, polyurethane dispersions and trimerization hexamethylene diisocyanate are pressed the weight ratio mixing of 1:1.1 ~ 1.3, add appropriate amount of deionized water and regulate emulsion viscosity, stir.
2. the preparation method of rosin based aqueous polyurethanes water-proof material according to claim 1, is characterized in that: described organic isocyanate is the one in isoflurane chalcone diisocyanate, tolylene diisocyanate, diphenylmethanediisocyanate.
3. the preparation method of rosin based aqueous polyurethanes water-proof material according to claim 1, is characterized in that: described maleated rosin polyester polyol consumption is 40 ~ 60% of polyoxyethylene glycol and maleated rosin polyester polyol total amount.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107099015A (en) * | 2017-03-24 | 2017-08-29 | 广东科茂林产化工股份有限公司 | A kind of modified aqueous polyurethane dispersoid and preparation method thereof |
| CN113956463A (en) * | 2021-10-22 | 2022-01-21 | 中国林业科学研究院林产化学工业研究所 | Application of photoresponse end-group rosinyl azobenzene polymer |
| CN114874659A (en) * | 2022-05-27 | 2022-08-09 | 华工丽颜(广东)新材料科技有限公司 | Preparation method of degradable waterborne polyurethane ink and product thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107099015A (en) * | 2017-03-24 | 2017-08-29 | 广东科茂林产化工股份有限公司 | A kind of modified aqueous polyurethane dispersoid and preparation method thereof |
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| CN113956463A (en) * | 2021-10-22 | 2022-01-21 | 中国林业科学研究院林产化学工业研究所 | Application of photoresponse end-group rosinyl azobenzene polymer |
| CN113956463B (en) * | 2021-10-22 | 2024-04-05 | 中国林业科学研究院林产化学工业研究所 | Application of photoresponsive end-group rosin-based azobenzene polymer |
| CN114874659A (en) * | 2022-05-27 | 2022-08-09 | 华工丽颜(广东)新材料科技有限公司 | Preparation method of degradable waterborne polyurethane ink and product thereof |
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