CN103483547A - Moisture-curing temperature-sensitive waterproof and moisture-permeable polyurethane and preparation method thereof - Google Patents
Moisture-curing temperature-sensitive waterproof and moisture-permeable polyurethane and preparation method thereof Download PDFInfo
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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
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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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
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4808—Mixtures of two or more polyetherdiols
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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
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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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
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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Abstract
The invention relates to moisture-curing temperature-sensitive waterproof and moisture-permeable polyurethane and a preparation method thereof. The preparation method comprises the following steps: vacuumizing 150 to 200 parts by weight of polyether glycol and 10 to 50 parts by weight of polyester glycol at 90 to 100 DEG C, and removing water from a system; cooling the mixture to 50 DEG C, introducing nitrogen to relieve vacuum, adding 30 to 50 parts by weight of diisocyanate, 1 to 5 parts by weight of an antioxidant and 0.1 to 0.5 parts by weight of a catalyst, and reacting for 20 to 40 minutes; and adding 0.5 to 1 part by weight of a viscosity stabilizer, heating the mixture to 80 to 90 DEG C, reacting for 2 to 3 hours, measuring the NCO percentage content of a reaction product, and heating and discharging the materials after the NCO value is constant. The prepared polyurethane has large moisture-permeable amount after cured, and has high bonding strength, good mechanical strength and flexibility, high responsiveness on environment temperature and remarkable temperature sensitivity, and the moisture-permeable switch temperature ranges from 35 DEG C and 55 DEG C.
Description
Technical field
The present invention relates to a kind of moisture curing temperature sensitive type waterproof moisture-penetrating urethane and preparation method thereof, particularly relate to functional type urethane and the preparation method of a kind of solvent-free damp solidifying, temperature sensitive and waterproofing and moisture-penetration performances excellence, belong to technical field of polymer materials.
Background technology
The temperature sensitive type waterproof moisture-penetrating urethane is a kind of novel intelligent macromolecular material, the intelligent material of predetermined response to is made in the stimulation of temperature to external world, it is before and after switch temperature (soft section phase transition temperature), obvious phase-state change can occur, cause the microtextures such as free volume bore hole size, fractional free volume of film inside that corresponding the change occurs, thereby make the macro property such as water vapor permeability, water-intake rate, mechanical property of film that correspondingly hop variation also occur, show significant temperature-sensing property.Such urethane can be widely used in the aspects such as textile materials, packaging material for food, medical material and separatory membrane.
The more temperature sensitive type waterproof moisture-penetrating urethane of research is mainly solvent borne polyurethane and aqueous polyurethane at present.Patent CN1016393759A has reported a kind of urethane resin and preparation method for the synthetic leather surface daub on a wall with intelligent moisture-permeable function, and this urethane has temperature-sensing property, belongs to solvent borne polyurethane; CN1648145A provides a kind of water base block polyurethane with temperature-sensing property and preparation method thereof; Patent CN101709197A discloses hydrophilic cross-linking crystal type polyurethane coating-forming agent of a kind of temperature sensitive type and preparation method thereof and application, this polyurethane coating agent is to utilize prepolymer method with 4,4 '-diphenylmethanediisocyanate (pure MDI) is hard section, take polyester or polyether glycol polyester as soft section, and add the small molecules diol chain extender, obtain through self-emulsifying, belong to aqueous polyurethane.Owing to having used a large amount of solvents, the solvent borne polyurethane preparation cost is higher, and is unfavorable for environmental protection; The aqueous polyurethane production technique is comparatively complicated, and the shortcoming that aqueous polyurethane exists that mechanical property is poor, water-repellancy and water vapour permeability can not be taken into account.
Summary of the invention
The purpose of this invention is to provide a kind of moisture curing temperature sensitive type waterproof moisture-penetrating urethane and preparation method thereof, after this urethane cures, vapor transfer rate is large, has high cohesive strength, good physical strength and snappiness, high to the responsiveness of envrionment temperature.
The technical scheme that the present invention takes is:
A kind of preparation method of moisture curing temperature sensitive type waterproof moisture-penetrating urethane comprises that step is as follows:
(1) by weight polyether Glycols 150-200 part and polyester diol 10-50 part are vacuumized at temperature 90-100 ℃, remove water in system;
(2) cool the temperature to 50 ℃, be filled with nitrogen and remove vacuum, add 20-50 part vulcabond, 1-5 part oxidation inhibitor, 0.1-0.5 part catalyzer, reaction 20-40 minute;
(3) add 0.3-1 part viscosity stabilizer, be warming up to 80~90 ℃, react 2~3 hours, the percentage composition of the NCO of measured reaction product, after nco value is constant, the intensification discharging.
Vulcabond described in above-mentioned preparation method is selected from 4, a kind of in 4 '-diphenylmethanediisocyanate (MDI), hydrogenation methylenebis phenyl isocyanate (HMDI).
Described polyether Glycols is selected from one or more in PTMG, polyoxyethylene glycol, polypropylene glycol, oxyethane and propylene oxide copolymerization glycol; Preferentially be selected from PTMG PTMEG, the polyoxyethylene glycol PEG of molecular weight 600~2000, the polypropylene glycol PPG of molecular weight 1000~2000, the oxyethane of molecular weight 2000~3000 and one or more in propylene oxide copolymerization glycol of molecular weight 1000~6000; One or both in the PTMG PTMEG of further preferred molecular weight 2000~4000, the polypropylene glycol PPG of molecular weight 1000~2000.
Described polyester diol is selected from one or more in polycaprolactone glycol, poly adipate succinic acid ester, poly-hexanodioic acid hexylene glycol ester, polyethylene glycol adipate; Preferentially be selected from one or more in the polyethylene glycol adipate PEA of poly-hexanodioic acid hexylene glycol ester PHA, molecular weight 2000~4000 of poly adipate succinic acid ester PBA, the molecular weight 2000~4000 of polycaprolactone glycol PCL, the molecular weight 600~4000 of molecular weight 2000~4000; One or both in the poly-hexanodioic acid hexylene glycol ester PHA of further preferred molecular weight 2000~4000, the poly adipate succinic acid ester PBA of preferred molecular weight 2000~4000.
Described catalyzer is selected from a kind of in dibutyl tin laurate, triethylene diamine, dual-morpholinyl diethyl ether, preferably dual-morpholinyl diethyl ether.
Described oxidation inhibitor is selected from commercially available AT-168 and the mixture of AT-225.
Described viscosity stabilizer to Benzoyl chloride, phosphoric acid, organic acid, organic acid anhydride one or more.
A kind of moisture curing temperature sensitive type waterproof moisture-penetrating urethane, the raw material be comprised of following weight part ratio is made, wherein vulcabond forms hard section, polyether Glycols and polyester diol form soft section, first polyether Glycols is mixed with polyester diol, remove moisture in system under vacuum, then be filled with nitrogen and add 5~50 ℃ of reaction 20-40 minute of vulcabond, oxidation inhibitor, catalyzer, add again viscosity stabilizer to be warming up to 80~90 ℃, react and make in 2~3 hours;
The weight part ratio of described raw material forms preferably:
Described moisture curing temperature sensitive type waterproof moisture-penetrating urethane, its soft or hard section weight ratio between 16-25:3-5, preferred 7-23:2-3.
Described moisture curing temperature sensitive type waterproof moisture-penetrating urethane heats up 120 ℃ the time: 1000~8000mPaS.
Soft section phase transition temperature of described moisture curing temperature sensitive type waterproof moisture-penetrating urethane is between 35~55 ℃.
Described vulcabond, polyether Glycols, polyester diol, catalyzer, antioxidant, viscosity stabilizer select kind as described in above-mentioned preparation method.
The present invention selects 4, and 4 '-diphenylmethanediisocyanate and hydrogenation methylenebis phenyl isocyanate can increase water-fast, the solvent resistance of urethane; Select crystallinity polyethers, polyester mixing dibasic alcohol as soft section, high to the responsiveness of envrionment temperature, the mechanical property that in the water vapour permeability that increases urethane and absorptive while, can improve urethane.Regulate and control the thoroughly wet switch temperature of urethane by the consumption of adjusting soft section (molecular weight, the ratio that comprise polyethers, polyester diol) and vulcabond.
The invention has the beneficial effects as follows:
(1) this urethane is the solvent-free single-component moisture cure urethanes, and in its production and use procedure, without any organic solvent, environmental protection is pollution-free;
(2) this urethane is solidificated between 18~48 hours fully, and after solidifying fully, vapor transfer rate is large, has high cohesive strength, good physical strength and snappiness.
(3) this urethane is high to the responsiveness of envrionment temperature, and wet switch temperature (soft section phase transition temperature) is between 30~55 ℃ thoroughly for they, and before and after this temperature, vapor transfer rate occurs significantly to change, and has obvious temperature-sensing property.
(4) preparation of this urethane adopts the single stage method melt polymerization, technique, simple to operate, and to equipment, without particular requirement, cost is low.
Embodiment
Below in conjunction with preferred embodiment, further illustrate.
Embodiment 1
The PBA of the PPG of the PTMEG of 30g molecular weight 2000,5g molecular weight 2000 and 10g molecular weight 4000 is joined in the 250mL four-hole boiling flask, vacuumize 2 hours under 100 ℃, remove moisture in system.Cool the temperature to 50 ℃, be filled with nitrogen and remove vacuum, add 9g MDI, 1g oxidation inhibitor (AT-168 and AT-225 equal amount of mixture), 0.1g dual-morpholinyl diethyl ether, react half an hour; Add 0.2g viscosity stabilizer (organic acid anhydride), be warming up to 85 ℃ of reactions 2 hours, the percentage composition of the NCO of measured reaction product, after nco value is constant, rise to 120 ℃ by temperature, viscosimetric 3340mPaS, and discharging, film forming, solidify 24 hours.Thoroughly wet switch temperature is 50 ℃, by differential scanning calorimeter (DSC), is recorded; The film vapor transfer rate is according to GB/T12704-91-B(moisture vapor transmission cup method) test.
The relation of vapor transfer rate and temperature after table 1 film-forming
Embodiment 2
The PHA of the PTMEG of 30g molecular weight 2000,5g molecular weight 2000 is joined in the 250mL four-hole boiling flask, vacuumize 2 hours under 100 ℃, remove moisture in system.Cool the temperature to 50 ℃, be filled with nitrogen and remove vacuum, add 6g MDI, 0.6g oxidation inhibitor (AT-168 and AT-225 equal amount of mixture), 0.06g dual-morpholinyl diethyl ether, react half an hour; Add 0.1g viscosity stabilizer (organic acid anhydride), be warming up to 85 ℃ of reactions 2 hours, the percentage composition of the NCO of measured reaction product, after nco value is constant, rise to 120 ℃ by temperature, viscosimetric 4408mPaS, and discharging, film forming, solidify 24 hours.Thoroughly wet switch temperature is 45 ℃, by differential scanning calorimeter (DSC), is recorded; The film vapor transfer rate is according to GB/T12704-91-B(moisture vapor transmission cup method) test.
The relation of vapor transfer rate and temperature after table 2 film-forming
Embodiment 3
The PBA of the PPG of the PTMEG of 30g molecular weight 2000,3g molecular weight 2000 and 5g molecular weight 2000 is joined in the 250mL four-hole boiling flask, vacuumize 2 hours under 100 ℃, remove moisture in system.Cool the temperature to 50 ℃, be filled with nitrogen and remove vacuum, add 6.6g MDI, 0.7g oxidation inhibitor (AT-168 and AT-225 equal amount of mixture), 0.07g dual-morpholinyl diethyl ether, react half an hour; Add 0.1g viscosity stabilizer (organic acid anhydride), be warming up to 85 ℃ of reactions 2 hours, the percentage composition of the NCO of measured reaction product, after nco value is constant, rise to 120 ℃ by temperature, viscosimetric 3820mPaS, and discharging, film forming, solidify 24 hours.Thoroughly wet switch temperature is 48 ℃, by differential scanning calorimeter (DSC), is recorded; The film vapor transfer rate is according to GB/T12704-91-B(moisture vapor transmission cup method) test.
The relation of vapor transfer rate and temperature after table 3 film-forming
Claims (7)
1. the preparation method of a moisture curing temperature sensitive type waterproof moisture-penetrating urethane, is characterized in that, comprises that step is as follows:
(1) by weight polyether Glycols 150-200 part and polyester diol 10-50 part are vacuumized at temperature 90-100 ℃, remove water in system;
(2) cool the temperature to 50 ℃, be filled with nitrogen and remove vacuum, add 20-50 part vulcabond, 1-5 part oxidation inhibitor, 0.1-0.5 part catalyzer, reaction 20-40 minute;
(3) add 0.3-1 part viscosity stabilizer, be warming up to 80~90 ℃, react 2~3 hours, the percentage composition of the NCO of measured reaction product, after nco value is constant, the intensification discharging.
2. the preparation method of a kind of moisture curing temperature sensitive type waterproof moisture-penetrating urethane according to claim 1 is characterized in that:
Described vulcabond is selected from 4, a kind of in 4 '-diphenylmethanediisocyanate, hydrogenation methylenebis phenyl isocyanate;
Polyether Glycols is selected from PTMG PTMEG, the polyoxyethylene glycol PEG of molecular weight 600~2000, the polypropylene glycol PPG of molecular weight 1000~2000, the oxyethane of molecular weight 2000~3000 and one or more in propylene oxide copolymerization glycol of molecular weight 1000~6000;
Polyester diol is selected from one or more in the polyethylene glycol adipate PEA of poly-hexanodioic acid hexylene glycol ester PHA, molecular weight 2000~4000 of poly adipate succinic acid ester PBA, the molecular weight 2000~4000 of polycaprolactone glycol PCL, the molecular weight 600~4000 of molecular weight 2000~4000;
Catalyzer is selected from a kind of in dibutyl tin laurate, triethylene diamine, dual-morpholinyl diethyl ether;
Viscosity stabilizer from organic acid, organic acid anhydride one or more.
3. a moisture curing temperature sensitive type waterproof moisture-penetrating urethane, it is characterized in that, the raw material be comprised of following weight part ratio is made, wherein vulcabond forms hard section, and polyether Glycols and polyester diol form soft section, first polyether Glycols are mixed with polyester diol, remove moisture in system under vacuum, be filled with again nitrogen and add vulcabond, oxidation inhibitor, 5~50 ℃ of reaction 20-40 minute of catalyzer, then add viscosity stabilizer to be warming up to 80~90 ℃, react and make in 2~3 hours;
5. a kind of moisture curing temperature sensitive type waterproof moisture-penetrating urethane according to claim 3, is characterized in that, its soft or hard section weight ratio is between 16-25:3-5.
6. a kind of moisture curing temperature sensitive type waterproof moisture-penetrating urethane according to claim 3, is characterized in that, described moisture curing temperature sensitive type waterproof moisture-penetrating urethane range of viscosities: the 1000~8000mPaS 120 ℃ time that heats up.
7. a kind of moisture curing temperature sensitive type waterproof moisture-penetrating urethane according to claim 3, is characterized in that, soft section phase transition temperature of described moisture curing temperature sensitive type waterproof moisture-penetrating urethane is between 35~55 ℃.
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105061721A (en) * | 2015-07-22 | 2015-11-18 | 东莞市吉鑫高分子科技有限公司 | Temperature-sensitive intelligent thermoplastic polyurethane elastomer and preparation method thereof |
CN104140518B (en) * | 2014-07-23 | 2018-01-16 | 青岛润国生态科技发展有限公司 | A kind of hydrophily one-component water cure polyurethane and preparation method thereof |
CN111286062A (en) * | 2020-03-16 | 2020-06-16 | 四川天星智能包装股份有限公司 | Composite material for fruit and vegetable packaging bags |
CN113150239A (en) * | 2021-04-09 | 2021-07-23 | 华南理工大学 | Preparation method of medical polyurethane adhesive with controllable curing time |
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CN1341133A (en) * | 1999-01-20 | 2002-03-20 | H.B.富勒许可和金融公司 | High moisture vapor transmission hot mele moisture cure polyurethane adhesive with exellent hydrolysis resistance |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104140518B (en) * | 2014-07-23 | 2018-01-16 | 青岛润国生态科技发展有限公司 | A kind of hydrophily one-component water cure polyurethane and preparation method thereof |
CN105061721A (en) * | 2015-07-22 | 2015-11-18 | 东莞市吉鑫高分子科技有限公司 | Temperature-sensitive intelligent thermoplastic polyurethane elastomer and preparation method thereof |
CN105061721B (en) * | 2015-07-22 | 2018-06-19 | 东莞市吉鑫高分子科技有限公司 | A kind of temperature sensitive intelligent thermoplastic polyurethane elastomer and preparation method thereof |
CN111286062A (en) * | 2020-03-16 | 2020-06-16 | 四川天星智能包装股份有限公司 | Composite material for fruit and vegetable packaging bags |
CN111286062B (en) * | 2020-03-16 | 2022-09-20 | 四川天星智能包装股份有限公司 | Composite material for fruit and vegetable packaging bags |
CN113150239A (en) * | 2021-04-09 | 2021-07-23 | 华南理工大学 | Preparation method of medical polyurethane adhesive with controllable curing time |
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