CN104845573B - High temperature resistant two-component ester soluble polyurethane adhesive and preparation method thereof - Google Patents
High temperature resistant two-component ester soluble polyurethane adhesive and preparation method thereof Download PDFInfo
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- CN104845573B CN104845573B CN201510215438.6A CN201510215438A CN104845573B CN 104845573 B CN104845573 B CN 104845573B CN 201510215438 A CN201510215438 A CN 201510215438A CN 104845573 B CN104845573 B CN 104845573B
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- polyurethane adhesive
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- 239000000853 adhesive Substances 0.000 title claims abstract description 20
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 20
- 150000002148 esters Chemical class 0.000 title claims abstract description 18
- 239000004814 polyurethane Substances 0.000 title claims abstract description 16
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 150
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 69
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 42
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims abstract description 36
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910000077 silane Inorganic materials 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 235000011037 adipic acid Nutrition 0.000 claims abstract description 9
- 239000001361 adipic acid Substances 0.000 claims abstract description 9
- 239000003822 epoxy resin Substances 0.000 claims abstract description 9
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 9
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims abstract description 8
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 8
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 238000009833 condensation Methods 0.000 claims description 14
- 230000005494 condensation Effects 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 230000032050 esterification Effects 0.000 claims description 10
- 238000005886 esterification reaction Methods 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 239000002351 wastewater Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 claims description 6
- 101710130081 Aspergillopepsin-1 Proteins 0.000 claims description 6
- 102100031007 Cytosolic non-specific dipeptidase Human genes 0.000 claims description 6
- 229920005906 polyester polyol Polymers 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 5
- 239000007822 coupling agent Substances 0.000 claims description 5
- 238000001514 detection method Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000006068 polycondensation reaction Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000007599 discharging Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 238000009413 insulation Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 abstract description 6
- 238000004806 packaging method and process Methods 0.000 abstract description 5
- 239000002131 composite material Substances 0.000 abstract description 4
- 238000010411 cooking Methods 0.000 abstract description 4
- 238000004659 sterilization and disinfection Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 238000003912 environmental pollution Methods 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
A kind of high temperature resistant two-component ester soluble polyurethane adhesive, including host and curing agent, the host are formed by the Raw material processing of following parts by weight：280 290 parts of dimethyl terephthalate (DMT), 105 115 parts of ethylene glycol, 380 400 parts of diethylene glycol (DEG), 230 240 parts of phthalic anhydride, 130 140 parts of adipic acid, 120 160 parts of methyl diphenylene diisocyanate, 400 600 parts of ethyl acetate, 34 parts of silane coupler；The curing agent is formed by the Raw material processing of following weight percents：50 65% epoxy resin, 3 5% silane couplers, 3 5% diethylenetriamines, surplus are ethyl acetate, and host and curing agent are with weight ratio 9 11 during use:12 mixing.A kind of heat resistance of present invention offer is good, can be used in 135 DEG C, 30 minutes cooking disinfection packagings；Chemical resistance；There are higher initial adhesion force and excellent combined strength bination to composite；Preparation technology is simple, and utilization rate of raw materials is high, the small ester soluble polyurethane adhesive of environmental pollution.
Description
Technical field：
The invention belongs to technical field of chemical adhesive, be related to a kind of high temperature resistant two-component ester soluble polyurethane adhesive and
Its preparation method.
Technical background：
Polyurethane adhesive refers to contain carbamate groups in strand（- NHCOO-）Or NCO
（- NCO）Adhesive.Divide from using form, mainly have one pack system and bi-component, one pack system polyurethane adhesive can be direct
Use, two component adhesive is using preceding needing impregnation.Polyurethane adhesive in the market is a lot, but heat resistance is paid no attention to mostly
Think, it is especially compound intolerant to 135 DEG C of boiling packaging.
The content of the invention：
Present invention the defects of existing for prior art, there is provided a kind of high temperature resistant two-component ester soluble polyurethane adhesive and
Its preparation method.Not only heat resistance is good for this method, can be used in 135 DEG C, 30 minutes cooking disinfection packagings, also with resistance to
Chemically, there are higher initial adhesion force and excellent combined strength bination to composite.
Therefore, the present invention adopts the following technical scheme that：
High temperature resistant two-component ester soluble polyurethane adhesive, including host and curing agent, the host is by following parts by weight
Raw material processing form：Dimethyl terephthalate (DMT) 280-290 parts, ethylene glycol 105-115 parts, diethylene glycol (DEG) 380-400 parts, adjacent benzene
Dicarboxylic acid anhydride 230-240 parts, adipic acid 130-140 parts, methyl diphenylene diisocyanate 120-160 parts, ethyl acetate 400-
600 parts, silane coupler 3-4 parts；The curing agent is formed by the Raw material processing of following weight percents：50-65% asphalt mixtures modified by epoxy resin
Fat, 3-5% silane couplers, 3-5% diethylenetriamines, surplus is ethyl acetate.
Preferably, the host is formed by the Raw material processing of following parts by weight：285 parts of dimethyl terephthalate (DMT), second two
110 parts of alcohol, 400 parts of diethylene glycol (DEG), 240 parts of phthalic anhydride, 130 parts of adipic acid, 150 parts of methyl diphenylene diisocyanate,
550 parts of ethyl acetate, 4 parts of silane coupler；The curing agent is formed by the Raw material processing of following weight percents：60% epoxy
Resin, 5% silane coupler, 3% diethylenetriamine, surplus is ethyl acetate.
A kind of preparation method of high temperature resistant two-component ester soluble polyurethane adhesive, the preparation method are real according to the following steps
It is existing：
（1）Dimethyl terephthalate (DMT), ethylene glycol, diethylene glycol (DEG) are added in pet reaction kettle, keep system temperature 160-
200 DEG C, carry out ester exchange reaction 3-5 hours, condensation process removing by-product carbinol；
（2）After methanol removal, phthalic anhydride, adipic acid are added, keeps 160-230 DEG C of system temperature, esterification
6-8 hours, condensation process removing esterification waste water；
（3）200-240 DEG C of system temperature is kept after dehydration, polycondensation reaction is carried out, the useless alcohol of condensation process removing, detects polyester
Polyalcohol stops reaction when reaching molecular weight 1800-2200, is cooled to 140-160 DEG C；
（4）Step（3）Less than 120 DEG C are continued cool to through heat exchanger after middle PEPA cooling, it is anti-into synthesis
Kettle is answered, continues cool to less than 80 DEG C, methyl diphenylene diisocyanate is added, the ethyl acetate of the total dosages of 70-80%, stirs,
Kept for 75-100 DEG C of reaction 4-5 hour of system temperature, test and analyze material viscosity in synthesis reaction vessel and reach 1000-2000 mPa
After s, the ethyl acetate and the silane coupler diluted material mass fraction that continue to add surplus are 50% ± 2%, are divided after being cooled to normal temperature
Material is taken on, obtains host modified poly ester polyol blends；
（5）Epoxy resin is added in heating response kettle, adds coupling agent, ethyl acetate is mixed and heated to 30 DEG C, guarantor
Warm 15-30min, then add the well mixed acquisition curing agent of diethylenetriamine.
（6）Host and curing agent are with mass ratio 9-11:1-2 is used in mixed way.
Beneficial effects of the present invention：
1 heat resistance is good, can be used in 135 DEG C, 30 minutes cooking disinfection packagings；
2 chemical resistances；
3 pairs of composites have higher initial adhesion force and excellent combined strength bination；
4 preparation technologies are simple, and utilization rate of raw materials is high, and environmental pollution is small.
Embodiment：
With reference to embodiment, the present invention will be further described.
Embodiment 1
A kind of preparation method of high temperature resistant two-component ester soluble polyurethane adhesive, is realized by following steps：
（1）280 parts of dimethyl terephthalate (DMT), 105 parts of ethylene glycol, 380 parts of diethylene glycol (DEG) are added in pet reaction kettle, are kept
160-200 DEG C of system temperature, carries out ester exchange reaction 3 hours, condensation process removing by-product carbinol；
（2）After methanol removal, 230 parts of phthalic anhydride, adipic acid 130 are added, part, keeps system temperature 160-230
DEG C, esterification 6 hours, condensation process removing esterification waste water；
（3）200-240 DEG C of system temperature is kept after dehydration, carries out polycondensation reaction, the useless alcohol of condensation process removing；Detect polyester
Polyalcohol stops reaction after reaching molecular weight 1800-2200, is cooled to 150 DEG C；
（4）Step（3）Less than 120 DEG C are cooled to through heat exchanger after middle PEPA condensation process, it is anti-into synthesis
Kettle is answered, continues cool to less than 80 DEG C, 120 parts of methyl diphenylene diisocyanate is added, 400 parts of ethyl acetate, stirs, keep
75-100 DEG C of system temperature reacts 4 hours, after material viscosity reaches 1000-2000mPas in detection and analysis synthesis reaction vessel, after
Continuous plus ethyl acetate and 3 parts of silane coupler diluted material mass fractions are 50% ± 2%, dispense discharging after being cooled to normal temperature, obtain
Obtain host modified poly ester polyol blends；
（5）50 parts of epoxy resin are added in heating response kettle, add 3 parts of coupling agents, 44 parts of ethyl acetate mixing add
Heat is incubated 15-30min to 30 DEG C, then adds the well mixed acquisition curing agent of 3 parts of diethylenetriamines；
（6）In use, host and curing agent are with weight ratio 20:3 ratios mix.
Wherein, toluene di-isocyanate(TDI) is drawn into metering device by the way of pipe suction and measured；Step（2）In waste water
In include ethylene glycol and diethylene glycol (DEG), step（3）Useless alcohol includes ethylene glycol, diethylene glycol (DEG) and a small amount of moisture, recycles.
Embodiment 2
A kind of preparation method of high temperature resistant two-component ester soluble polyurethane adhesive, is realized by following steps：
（1）290 parts of dimethyl terephthalate (DMT), 115 parts of ethylene glycol, 400 parts of diethylene glycol (DEG) are added in pet reaction kettle, are kept
160-200 DEG C of system temperature, carries out ester exchange reaction 5 hours, condensation process removing by-product carbinol；
（2）After methanol removal, 240 parts of phthalic anhydride, 140 parts of adipic acid are added, keeps system temperature 160-230
DEG C, esterification 8 hours, condensation process removing esterification waste water；
（3）200-240 DEG C of system temperature is kept after dehydration, carries out polycondensation reaction, the useless alcohol of condensation process removing；Detect polyester
Polyalcohol stops reaction after reaching molecular weight 1800-2200, is cooled to 140 DEG C；
（4）Step（3）Less than 120 DEG C are cooled to through heat exchanger after middle PEPA condensation process, it is anti-into synthesis
Kettle is answered, continues cool to less than 80 DEG C, 160 parts of methyl diphenylene diisocyanate is added, 500 parts of ethyl acetate, stirs, keep
75-100 DEG C of system temperature reacts 5 hours, after material viscosity reaches 1000-2000mPas in detection and analysis synthesis reaction vessel, after
Continuous plus ethyl acetate and 4 parts of silane coupler diluted material mass fractions are 50% ± 2%, dispense discharging after being cooled to normal temperature, obtain
Obtain host modified poly ester polyol blends；
（5）65 parts of epoxy resin are added in heating response kettle, add 5 parts of coupling agents, 25 parts of ethyl acetate mixing add
Heat is incubated 15-30min to 30 DEG C, then adds the well mixed acquisition curing agent of 5 parts of diethylenetriamines；
（6）In use, host and curing agent are with weight ratio 9:1 mixing.
Wherein, toluene di-isocyanate(TDI) is drawn into metering device by the way of pipe suction and measured；Step（2）In waste water
In include ethylene glycol and diethylene glycol (DEG), step（3）Useless alcohol includes ethylene glycol, diethylene glycol (DEG) and a small amount of moisture, recycles.
Embodiment 3
A kind of high temperature resistant two-component ester soluble polyurethane adhesive and preparation method thereof, is realized by following steps：
（1）285 parts of dimethyl terephthalate (DMT), 110 parts of ethylene glycol, 390 parts of diethylene glycol (DEG) are added in pet reaction kettle, are kept
160-200 DEG C of system temperature, carries out ester exchange reaction 4 hours, removes by-product carbinol；
（2）After methanol removal, 235 parts of phthalic anhydride, 135 parts of adipic acid are added, keeps system temperature 160-230
DEG C, esterification 7 hours, remove esterification waste water；
（3）200-240 DEG C of system temperature is kept after dehydration, carries out polycondensation reaction, removes useless alcohol；Detection PEPA reaches
Stop reaction after to molecular weight 1800-2200, be cooled to 160 DEG C；
（4）Step（3）Less than 120 DEG C are cooled to through heat exchanger after middle PEPA condensation process, it is anti-into synthesis
Kettle is answered, continues cool to less than 80 DEG C, 140 parts of methyl diphenylene diisocyanate is added, 450 parts of ethyl acetate, stirs, keep
75-100 DEG C of system temperature reacts 4.5 hours, after material viscosity reaches 1000-2000mPas in detection and analysis synthesis reaction vessel,
Continue to add ethyl acetate and 3.4 parts of silane coupler diluted material mass fractions to be 50% ± 2%, dispensed out after being cooled to normal temperature
Material, obtain host modified poly ester polyol blends；
（5）60 parts of epoxy resin are added in heating response kettle, add 5 parts of coupling agents, 32 parts of ethyl acetate mixing add
Heat is incubated 15-30min to 30 DEG C, then adds the well mixed acquisition curing agent of 3 parts of diethylenetriamines；
（6）In use, host and curing agent component are with weight ratio 22:4 mixing.
Wherein, toluene di-isocyanate(TDI) is drawn into metering device by the way of pipe suction and measured；Step（2）In waste water
In include ethylene glycol and diethylene glycol (DEG), step（3）Useless alcohol includes ethylene glycol, diethylene glycol (DEG) and a small amount of moisture, recycles.
Two-component ester soluble polyurethane adhesive heat resistance is good made from embodiment 1-3, can be used in 135 DEG C, and 30
Minute cooking disinfection packaging；Chemical resistance, there are higher initial adhesion force and excellent combined strength bination to composite, prepare work in addition
Skill is also simple, and utilization rate of raw materials is high, and environmental pollution is small.
Listed above is only the specific embodiment of the present invention.It is clear that the invention is not restricted to above example, can also have
Many deformations.All deformations that one of ordinary skill in the art directly can export or associate from present disclosure,
It is considered as protection scope of the present invention.
Claims (1)
1. high temperature resistant two-component ester dissolubility polyurethane adhesive, including host and curing agent, it is characterised in that the host is under
The Raw material processing of row parts by weight forms：285 parts of dimethyl terephthalate (DMT), 110 parts of ethylene glycol, 400 parts of diethylene glycol (DEG), O-phthalic
240 parts of acid anhydrides, 130 parts of adipic acid, 150 parts of methyl diphenylene diisocyanate, 550 parts of ethyl acetate, 4 parts of silane coupler；
The curing agent is formed by the Raw material processing of following weight percents：60% epoxy resin, 5% silane coupler, 3% Sanya second
Base triamine, surplus are ethyl acetate, and the preparation method of the adhesive is realized according to the following steps：(1) dimethyl terephthalate (DMT),
Ethylene glycol, diethylene glycol (DEG) are added in pet reaction kettle, keep 160-200 DEG C of system temperature, are carried out ester exchange reaction 3-5 hours, cold
Solidifying processing removing by-product carbinol；
(2) after methanol removal, phthalic anhydride, adipic acid are added, keeps 160-230 DEG C of system temperature, esterification 6-8 is small
When, condensation process removing esterification waste water；
(3) 200-240 DEG C of system temperature is kept after being dehydrated, polycondensation reaction is carried out, the useless alcohol of condensation process removing, detects polyester polyols
Alcohol stops reaction when reaching molecular weight 1800-2200, is cooled to 140-160 DEG C；
(4) through heat exchanger less than 120 DEG C are continued cool to after PEPA cooling in step (3), into synthesis reaction vessel,
Less than 80 DEG C are continued cool to, methyl diphenylene diisocyanate is added, the ethyl acetate of the total dosages of 70-80%, stirs, keep
75-100 DEG C of system temperature reacts 4-5 hours, after material viscosity reaches 1000-2000mPas in detection and analysis synthesis reaction vessel,
Ethyl acetate and the silane coupler diluted material mass fraction for continuing to add surplus are 50% ± 2%, are dispensed after being cooled to normal temperature
Discharging, obtain host modified poly ester polyol blends；
(5) epoxy resin is added in heating response kettle, adds coupling agent, ethyl acetate is mixed and heated to 30 DEG C, insulation 15-
30min, then add the well mixed acquisition curing agent of diethylenetriamine；
(6) host and curing agent are used in mixed way with mass ratio 9-11: 1-2.
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| CN201510215438.6A CN104845573B (en) | 2015-04-30 | 2015-04-30 | High temperature resistant two-component ester soluble polyurethane adhesive and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510215438.6A CN104845573B (en) | 2015-04-30 | 2015-04-30 | High temperature resistant two-component ester soluble polyurethane adhesive and preparation method thereof |
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| CN114015407A (en) * | 2021-11-12 | 2022-02-08 | 广东泰强化工实业有限公司 | Pollution-free solvent-free two-component polyurethane adhesive and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013016130A2 (en) * | 2011-07-22 | 2013-01-31 | H.B. Fuller Company | A reactive hot-melt adhesive for use on electronics |
| CN104449531A (en) * | 2013-09-22 | 2015-03-25 | 湖北航天化学技术研究所 | Two-component polyurethane resin for metal packaging tanks, and preparation method thereof |
-
2015
- 2015-04-30 CN CN201510215438.6A patent/CN104845573B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013016130A2 (en) * | 2011-07-22 | 2013-01-31 | H.B. Fuller Company | A reactive hot-melt adhesive for use on electronics |
| CN104449531A (en) * | 2013-09-22 | 2015-03-25 | 湖北航天化学技术研究所 | Two-component polyurethane resin for metal packaging tanks, and preparation method thereof |
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