CN105061712A - High-strength PU (polyurethane) sealant and preparation method thereof - Google Patents
High-strength PU (polyurethane) sealant 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
- C08G18/28—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
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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
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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
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
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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
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Sealing Material Composition (AREA)
Abstract
The invention relates to the field of polymer chemistry, particularly to a high-strength PU (polyurethane) sealant and a preparation method thereof. The preparation method of the high-strength PU sealant comprises steps as follows: (1) after a lignin raw material is dissolved in an organic solvent, solid sodium hydroxide is added, then epoxy propane is added, a polyol is added and continuously stirred, and the solvent is evaporated, so that a lignin polyol is obtained; (2) the lignin polyol, a polyether polyol, a plasticizer, an antioxidant, an amine catalyst and a tin catalyst are mixed evenly, and a combined polyether is obtained; after the combined polyether, waste rubber powder and filler are mixed, isocyanate is added to the mixture, and the high-strength PU sealant is prepared. According to the method, the modified lignin is added to a formula, the strength of PU is enhanced, the solubility of the lignin in a reaction system is improved, the anti-ageing performance of the PU sealant is improved, and the service life is greatly prolonged.
Description
(1) technical field
The present invention relates to chemical field, particularly a kind of high-strength polyurethane seal gum and preparation method thereof.
(2) background technology
Due to the situation that the facing mankind energy and ecocrisis are more nervous, natural polymer comes into one's own day by day.Xylogen is a kind of natural high polymer be extensively present in plant materials, is a kind of very abundant renewable resources.There is aromatic base, phenolic hydroxyl group, alcoholic extract hydroxyl group, carbon back conjugated double bond isoreactivity group in the molecular structure of xylogen, therefore can carry out a lot of chemical reaction, thus be applied in the middle of follow-up Chemicals.
The seal gum that polyurethane sealant is is main component with urethanes and base polyurethane prepolymer for use as.Polyurethane sealant has good tensile strength, excellent cementability, elasticity, wear resistance, oil-proofness, winter hardiness and weathering resistance, be widely used in buildings, square, highway as inlay sealing material, and the sealing of automobile making, glass installation, electronic filling, submarine and rocket etc.But polyurethane sealant also exists some shortcomings, as can not be heat-resisting for a long time; Light color formula is easily by ultraviolet light and aging; Water tolerance is poor, and particularly alkaline-resisting water-based is not good enough.
Xylogen is that occurring in nature content is only second to cellulosic natural macromolecular material, regenerates every year with the speed of 5 × 1010t, is a kind of organic raw material being rich in industrial value.In Mierocrystalline cellulose related industries (as plant hydrolyzed and pulp and paper industry), xylogen a large amount of output as a by-product usually.But; effective utilization of xylogen is unsatisfactory; up to the present; xylogen more than 95% still directly enters rivers with the form of " black liquor " or is burnt; not only cause environmental pollution, be also the great wasting of resources, therefore simultaneously; xylogen is effectively utilized, is had positive effect to environment protection and Economic development.
(3) summary of the invention
The present invention, in order to make up the deficiencies in the prior art, provides a kind of high-strength polyurethane seal gum and preparation method thereof.
The present invention is achieved through the following technical solutions:
A kind of preparation method of high-strength polyurethane seal gum, it is characterized in that: comprise the following steps: the preparation of (1) modified lignin resin: after xylogen raw material 100-200 mass parts organic solvent dissolution, add 0.5-3 mass parts solid sodium hydroxide, add the propylene oxide of 10-30 mass parts again, add 100-200 mass parts polyvalent alcohol Keep agitation again and be heated to 100-150 DEG C under deoxygenation and air-tight state, and react 1-2h at this temperature; Then room temperature is cooled to, solvent evaporated thus obtain xylogen polyvalent alcohol;
(2) preparation of combined polyether: by above-mentioned xylogen polyvalent alcohol 100-150 mass parts, polyether glycol 50-100 mass parts, softening agent 80-120 mass parts, 1-3 mass parts amines catalyst, 0.05-0.2 mass parts tin class catalyzer, antioxidant 1-3 mass parts mixing and stirring, obtains combined polyether;
(3) preparation of urethane: by aforesaid combination polyethers 100 mass parts, waste Crumb rubber 10-20 mass parts, filler 60-100 mass parts, add in reactor, under 80-100 DEG C of temperature and vacuum tightness are 0.09 ± 0.005MPa condition, stir 1-2h, then add isocyanic ester 60-150 mass parts wherein, continue reaction 1-2h, then in reactor, be filled with nitrogen to normal pressure, treat that cold the going of material, to room temperature discharging, obtains high-strength polyurethane seal gum.
Wherein, described in step (1), polyvalent alcohol comprises the combination of one or more in ethylene glycol, glycerol, BDO.
Wherein, described in step (1), organic solvent comprises acetone, DMF, the organic solvent of acetone and DMF 1:1 mixing by volume.
Wherein, xylogen described in step (1) is the combination of one or more in high-boiling alcohol lignin, enzymolysis xylogen, thermo-cracking xylogen, acetic acid lignin, Peracetic Acid xylogen or peroxy acid xylogen.
Wherein, amines catalyst described in step (2) is one or more in triethylene diamine, triethylamine, tetramethyl-diethylene diamine, dimethylcyclohexylamine, diethanolamine, trolamine, divinyl ethylene glycol amine and α-amino isopropyl alcohol; Described organic tin catalyzer is one or more in stannous octoate, dibutyl tin dilaurate, two (dodecyl sulphur) dibutyl tin, Mono-n-butyltin and Dibutyltin oxide.Softening agent comprises dibutyl phthalate, dioctyl phthalate (DOP), Dinonylphthalate or Di Iso Decyl Phthalate.
Wherein, described in step (3), waste Crumb rubber is 800-1000 order.
Wherein, isocyanic ester described in step (3) is one or more in tolylene diisocyanate, '-diphenylmethane diisocyanate, hexamethylene diisocyanate and isophorone diisocyanate.
Wherein, described in step (3), filler comprises Shawinigan black, titanium dioxide, calcium carbonate, talcum powder, organobentonite.
The present invention is by the wooden intensity usually increasing polyurethane sealant, and xylogen has cancellated, containing firm groups such as phenyl ring macromolecular compound, can increase the intensity of polyurethane sealant in hard polyurethane foam.Methoxyl group in lignin molecule on Syringa oblata Lindl. base phenyl ring forms sterically hindered structure to hydroxyl, can catch the free radical and terminating chain reaction that generate in thermo-oxidative ageing process, thus improve the thermo-oxidative stability of material; Meanwhile, this sterically hindered phenol structure also becomes photostabilizer to free radical capture, and strongthener is to the tolerance of ultraviolet irradiation.The present invention makes xylogen be scattered in reaction system effectively, avoids the detrimentally affect of small molecule solvent in polymerization foam process simultaneously.
The invention has the beneficial effects as follows: by adding modified lignin resin in formula, adding the intensity of urethane, improve the solvability of xylogen in reaction system, improve the ageing resistance of polyurethane sealant, work-ing life extends greatly.Relative to the polyurethane sealant prepared by traditional method, the lignin-base polyurethane sealant that the present invention obtains has more excellent ultimate compression strength, tensile strength and shock strength.
(4) embodiment
Embodiment 1:
Comprise the following steps:
(1) preparation of modified lignin resin: after xylogen raw material 100 mass parts acetone solution, add 0.5 mass parts solid sodium hydroxide, add the propylene oxide of 10 mass parts again, add 100 mass parts glycerol Keep agitation again and be heated to 100-150 DEG C under deoxygenation and air-tight state, and react 1-2h at this temperature; Then room temperature is cooled to, solvent evaporated thus obtain xylogen polyvalent alcohol;
(2) preparation of combined polyether: by above-mentioned xylogen polyvalent alcohol 100 mass parts, polyether glycol 50 mass parts, dibutyl phthalate 80 mass parts, 1 mass parts dimethylcyclohexylamine, 0.05 mass parts dibutyl tin dilaurate, antioxidant 1 mass parts mixing and stirring, obtains combined polyether;
(3) preparation of urethane: by aforesaid combination polyethers 100 mass parts, waste Crumb rubber 10 mass parts, titanium dioxide 60 mass parts, add in reactor, under 80-100 DEG C of temperature and vacuum tightness are 0.09 ± 0.005MPa condition, stir 1-2h, then add tolylene diisocyanate 60 mass parts wherein, continue reaction 1-2h, then in reactor, be filled with nitrogen to normal pressure, treat that cold the going of material, to room temperature discharging, obtains high-strength polyurethane seal gum.
By the high-strength polyurethane seal gum that above-mentioned composition and engineering is obtained, its performance physical and chemical index is as follows: the not sticky time (min): 50; Curing speed (mm/d): 4.02; Hardness (shore A °): 58; Tensile bond intensity (MPa): 14.5; Elongation (%): 458; Shearing resistance (MPa): 6.1; Tear strength (N/mm): 22.1.
Embodiment 2:
Comprise the following steps:
(1) preparation of modified lignin resin: after xylogen raw material 200 mass parts acetone and the DMF organic solvent dissolution that 1:1 mixes by volume, add 3 mass parts solid sodium hydroxides, add the propylene oxide of 30 mass parts again, add 200 mass parts polyvalent alcohol Keep agitation again and be heated to 100-150 DEG C under deoxygenation and air-tight state, and react 1-2h at this temperature; Then room temperature is cooled to, solvent evaporated thus obtain xylogen polyvalent alcohol;
(2) preparation of combined polyether: by above-mentioned xylogen polyvalent alcohol 150 mass parts, polyether glycol 100 mass parts, Dinonylphthalate 120 mass parts, 3 mass parts diethanolamine, 0.2 mass parts dibutyl tin dilaurate, antioxidant 3 mass parts mixing and stirring, obtains combined polyether;
(3) preparation of urethane: by aforesaid combination polyethers 100 mass parts, waste Crumb rubber 20 mass parts, organobentonite 100 mass parts, add in reactor, under 80-100 DEG C of temperature and vacuum tightness are 0.09 ± 0.005MPa condition, stir 1-2h, then add '-diphenylmethane diisocyanate 150 mass parts wherein, continue reaction 1-2h, then in reactor, be filled with nitrogen to normal pressure, treat that cold the going of material, to room temperature discharging, obtains high-strength polyurethane seal gum.
By the high-strength polyurethane seal gum that above-mentioned composition and engineering is obtained, its performance physical and chemical index is as follows: the not sticky time (min): 45; Curing speed (mm/d): 4.32; Hardness (shore A °): 55; Tensile bond intensity (MPa): 13.7; Elongation (%): 438; Shearing resistance (MPa): 5.9; Tear strength (N/mm): 21.8.
Embodiment 3:
Comprise the following steps:
(1) preparation of modified lignin resin: after xylogen raw material 150 mass parts acetone solution, add 2.8 mass parts solid sodium hydroxides, add the propylene oxide of 23 mass parts again, add 100 mass parts glycerol Keep agitation again and be heated to 100-150 DEG C under deoxygenation and air-tight state, and react 1-2h at this temperature; Then room temperature is cooled to, solvent evaporated thus obtain xylogen polyvalent alcohol;
(2) preparation of combined polyether: by above-mentioned xylogen polyvalent alcohol 120 mass parts, polyether glycol 75 mass parts, dibutyl phthalate 90 mass parts, 1 mass parts dimethylcyclohexylamine, 0.1 mass parts dibutyl tin dilaurate, antioxidant 2 mass parts mixing and stirring, obtains combined polyether;
(3) preparation of urethane: by aforesaid combination polyethers 100 mass parts, waste Crumb rubber 13 mass parts, titanium dioxide 80 mass parts, add in reactor, under 80-100 DEG C of temperature and vacuum tightness are 0.09 ± 0.005MPa condition, stir 1-2h, then add tolylene diisocyanate 120 mass parts wherein, continue reaction 1-2h, then in reactor, be filled with nitrogen to normal pressure, treat that cold the going of material, to room temperature discharging, obtains high-strength polyurethane seal gum.
By the high-strength polyurethane seal gum that above-mentioned composition and engineering is obtained, its performance physical and chemical index is as follows: the not sticky time (min): 48; Curing speed (mm/d): 4.22; Hardness (shore A °): 58; Tensile bond intensity (MPa): 14.2; Elongation (%): 462; Shearing resistance (MPa): 6.1; Tear strength (N/mm): 21.0.
Claims (8)
1. the preparation method of a high-strength polyurethane seal gum, it is characterized in that: comprise the following steps: the preparation of (1) modified lignin resin: after xylogen raw material 100-200 mass parts organic solvent dissolution, add 0.5-3 mass parts solid sodium hydroxide, add the propylene oxide of 10-30 mass parts again, add 100-200 mass parts polyvalent alcohol Keep agitation again and be heated to 100-150 DEG C under deoxygenation and air-tight state, and react 1-2h at this temperature; Then room temperature is cooled to, solvent evaporated thus obtain xylogen polyvalent alcohol;
(2) preparation of combined polyether: by above-mentioned xylogen polyvalent alcohol 100-150 mass parts, polyether glycol 50-100 mass parts, softening agent 80-120 mass parts, 1-3 mass parts amines catalyst, 0.05-0.2 mass parts tin class catalyzer, antioxidant 1-3 mass parts mixing and stirring, obtains combined polyether;
(3) preparation of urethane: by aforesaid combination polyethers 100 mass parts, waste Crumb rubber 10-20 mass parts, filler 60-100 mass parts, add in reactor, under 80-100 DEG C of temperature and vacuum tightness are 0.09 ± 0.005MPa condition, stir 1-2h, then add isocyanic ester 60-150 mass parts wherein, continue reaction 1-2h, then in reactor, be filled with nitrogen to normal pressure, treat that cold the going of material, to room temperature discharging, obtains high-strength polyurethane seal gum.
2. the preparation method of high-strength polyurethane seal gum according to claim 1, is characterized in that: described in step (1), polyvalent alcohol comprises the combination of one or more in ethylene glycol, glycerol, BDO.
3. the preparation method of high-strength polyurethane seal gum according to claim 1, is characterized in that: described in step (1), organic solvent comprises acetone, DMF, the organic solvent of acetone and DMF 1:1 mixing by volume.
4. the preparation method of high-strength polyurethane seal gum according to claim 1, is characterized in that: xylogen described in step (1) is the combination of one or more in high-boiling alcohol lignin, enzymolysis xylogen, thermo-cracking xylogen, acetic acid lignin, Peracetic Acid xylogen or peroxy acid xylogen.
5. the preparation method of high-strength polyurethane seal gum according to claim 1, is characterized in that: amines catalyst described in step (2) is one or more in triethylene diamine, triethylamine, tetramethyl-diethylene diamine, dimethylcyclohexylamine, diethanolamine, trolamine, divinyl ethylene glycol amine and α-amino isopropyl alcohol; Described organic tin catalyzer is one or more in stannous octoate, dibutyl tin dilaurate, two (dodecyl sulphur) dibutyl tin, Mono-n-butyltin and Dibutyltin oxide.
6. the preparation method of high-strength polyurethane seal gum according to claim 1, is characterized in that: described in step (3), waste Crumb rubber is 800-1000 order.
7. the preparation method of high-strength polyurethane seal gum according to claim 1, is characterized in that: isocyanic ester described in step (3) is one or more in tolylene diisocyanate, '-diphenylmethane diisocyanate, hexamethylene diisocyanate and isophorone diisocyanate.
8. the preparation method of high-strength polyurethane seal gum according to claim 1, is characterized in that: described in step (3), filler comprises Shawinigan black, titanium dioxide, calcium carbonate, talcum powder, organobentonite.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510421134.5A CN105061712A (en) | 2015-07-17 | 2015-07-17 | High-strength PU (polyurethane) sealant and preparation method thereof |
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| CN201510421134.5A CN105061712A (en) | 2015-07-17 | 2015-07-17 | High-strength PU (polyurethane) sealant and preparation method thereof |
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Cited By (7)
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| CN105331325A (en) * | 2015-11-25 | 2016-02-17 | 华南理工大学 | Lignin/polyurethane/polyethyleneimine wood adhesive and preparation method thereof |
| CN106543949A (en) * | 2016-10-28 | 2017-03-29 | 天长市永泰密封材料有限公司 | A kind of high-strength impact-resistant polyurethane building sealant and preparation method thereof |
| CN108559046A (en) * | 2018-01-09 | 2018-09-21 | 长春工业大学 | A kind of ozonisation modified lignin resin polyurethane and preparation method thereof |
| CN109337589A (en) * | 2018-07-11 | 2019-02-15 | 合肥同佑电子科技有限公司 | A kind of use for electronic products high-intensity sealing glue and preparation method thereof |
| CN110172327A (en) * | 2019-05-31 | 2019-08-27 | 黄敏 | Photocuring composite adhesive and its production technology |
| CN110343496A (en) * | 2019-07-19 | 2019-10-18 | 大连工业大学 | A kind of lignin-base adhesive for polyurethane of epoxidation modification |
| CN113142184A (en) * | 2021-04-08 | 2021-07-23 | 浙江海洋大学 | Method for manufacturing marine organism specimen for teaching |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106543949A (en) * | 2016-10-28 | 2017-03-29 | 天长市永泰密封材料有限公司 | A kind of high-strength impact-resistant polyurethane building sealant and preparation method thereof |
| CN108559046A (en) * | 2018-01-09 | 2018-09-21 | 长春工业大学 | A kind of ozonisation modified lignin resin polyurethane and preparation method thereof |
| CN109337589A (en) * | 2018-07-11 | 2019-02-15 | 合肥同佑电子科技有限公司 | A kind of use for electronic products high-intensity sealing glue and preparation method thereof |
| CN110172327A (en) * | 2019-05-31 | 2019-08-27 | 黄敏 | Photocuring composite adhesive and its production technology |
| CN110343496A (en) * | 2019-07-19 | 2019-10-18 | 大连工业大学 | A kind of lignin-base adhesive for polyurethane of epoxidation modification |
| CN113142184A (en) * | 2021-04-08 | 2021-07-23 | 浙江海洋大学 | Method for manufacturing marine organism specimen for teaching |
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