CN103725244B - Method for preparing modified terephthalic acid neopentyl glycol copolyester hot melt adhesive for making membranes - Google Patents
Method for preparing modified terephthalic acid neopentyl glycol copolyester hot melt adhesive for making membranes Download PDFInfo
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- CN103725244B CN103725244B CN201210393518.7A CN201210393518A CN103725244B CN 103725244 B CN103725244 B CN 103725244B CN 201210393518 A CN201210393518 A CN 201210393518A CN 103725244 B CN103725244 B CN 103725244B
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- China
- Prior art keywords
- terephthalic acid
- neopentyl glycol
- melt adhesive
- glycol
- hot melt
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000004831 Hot glue Substances 0.000 title claims abstract description 22
- 229920001634 Copolyester Polymers 0.000 title claims abstract description 17
- IMJICWAXKLDGAL-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;terephthalic acid Chemical class OCC(C)(C)CO.OC(=O)C1=CC=C(C(O)=O)C=C1 IMJICWAXKLDGAL-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims abstract description 7
- 239000012528 membrane Substances 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 36
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 239000002131 composite material Substances 0.000 claims abstract description 12
- 230000032050 esterification Effects 0.000 claims abstract description 12
- 238000005886 esterification reaction Methods 0.000 claims abstract description 12
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000006837 decompression Effects 0.000 claims abstract description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 238000003756 stirring Methods 0.000 claims description 12
- 238000010792 warming Methods 0.000 claims description 12
- -1 poly(oxyethylene glycol) Polymers 0.000 claims description 11
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 claims description 7
- 230000009849 deactivation Effects 0.000 claims description 7
- 239000004200 microcrystalline wax Substances 0.000 claims description 7
- 235000019808 microcrystalline wax Nutrition 0.000 claims description 7
- 230000004048 modification Effects 0.000 claims description 7
- 238000012986 modification Methods 0.000 claims description 7
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 6
- 230000000873 masking effect Effects 0.000 claims description 5
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 230000008018 melting Effects 0.000 abstract description 6
- 238000002844 melting Methods 0.000 abstract description 6
- 238000003860 storage Methods 0.000 abstract description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000007710 freezing Methods 0.000 description 5
- 230000008014 freezing Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000005453 pelletization Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000010298 pulverizing process Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The invention discloses a method for preparing a modified terephthalic acid neopentyl glycol copolyester hot melt adhesive for making membranes. The method mainly comprises the following steps: (1) esterifying terephthalic, m-phthalic acid, neopentyl glycol, ethylene glycol and polyethylene glycol 400 under the action of a TiO2/SiO2 composite catalyst; (2) after esterification is completed, conducting decompression polycondensation to obtain a copolymer; (3) adding an addition agent into the product of the step (2), and softening the copolymer. The obtained modified terephthalic acid neopentyl glycol copolyester hot melt adhesive has the characteristic of a high initial melting point and resists high temperature and does not deposit knots during transportation and storage.
Description
Technical field
The present invention relates to a kind of masking modification terephthalic acid neopentyl glycol copolyester hot melt adhesive and preparation method thereof, particularly a kind of just fusing point modification terephthalic acid neopentyl glycol copolyester hot melt adhesive that is high, not easily long-pending knot in transport in summer and when storing.
Background technology
At present, polyester hot-melt adhesive is rapidly developed, and much character is all improved, but the unit of the first fusing point polyester hot-melt adhesive of special Study and Development height is relatively less.From the prior art, the first fusing point of the polyester hot-melt adhesive developed is general lower, and when finally causing in summer high temperature transport and store, hot-melt adhesive powder or film easily amass knot and stick into block.
Summary of the invention
Object of the present invention be exactly according to exist in existing hot melt adhesive just fusing point low, cannot when summer temperature high the defect such as easier shipping storage and provide a kind of adaptation to transport under the high temperature conditions, the manufacture method of first fusing point (45-50 DEG C) the modification terephthalic acid neopentyl glycol copolyester hot melt adhesive of the height that stores, meet the needs of association area.
Method of the present invention comprises the steps:
(1) terephthalic acid, m-phthalic acid and neopentyl glycol, ethylene glycol, poly(oxyethylene glycol) 400 are at TiO
2/ SiO
2under composite catalyst effect, carry out esterification, temperature of reaction is 175 ~ 200 DEG C, and when the quantity of distillate of the water that esterification generates is 90 ~ 95% of theoretical amount, esterification terminates;
(2) continue to be warming up to 230 ~ 250 DEG C and carry out decompression polycondensation, reaction pressure is 50 ~ 300 Pa, and the time is 1.0 ~ 1.5 hours, obtains multipolymer;
(3) deactivation system vacuum state, under 220 ~ 245 DEG C and normal pressure, adds the product of step (2) by auxiliary agent, constant temperature stirs 0.25 ~ 0.5 hour, obtains masking modification terephthalic acid neopentyl glycol copolyester hot melt adhesive;
Described terephthalic acid, m-phthalic acid, ethylene glycol, mol ratio between neopentyl glycol and poly(oxyethylene glycol) 400 are respectively:
Terephthalic acid: m-phthalic acid=1.5: 0.5 ~ 1.5;
Terephthalic acid: neopentyl glycol=1.0: 0.5 ~ 1.5;
Neopentyl glycol: ethylene glycol: poly(oxyethylene glycol) 400=1.0: 0.5 ~ 1.0: 0.15 ~ 0.05.
The TiO of described catalyzer to be titanium silicon mol ratio be 9:1 ~ 2
2/ SiO
2composite catalyst, and the mass ratio of catalyzer and terephthalic acid is:
TiO
2/ SiO
2composite catalyst: terephthalic acid=0.025 ~ 0.050: 100.
Described auxiliary agent is selected from the one in paraffin and Microcrystalline Wax, and its quality added is 1.5% ~ 3.0% of terephthalic acid quality.
Compared with prior art, innovative point of the present invention is: the copolyester hot melt adhesive of the present invention's technology used manufacture has higher first fusing point, this type of copolyester hot melt adhesive withstands the test of hot environment, and in transport in summer and storage process, not easily long-pending knot sticks into block.
Embodiment
Embodiment 1
In the polymerization reaction kettle of 2.5L with water distilling apparatus, add terephthalic acid (199.32g), m-phthalic acid (66.44g), neopentyl glycol (156.23g), ethylene glycol (89.28g) and poly(oxyethylene glycol) 400 (24.0g), titanium silicon composite catalyst (0.137g), heating, stir, when interior temperature reaches 137 DEG C, material starts fusing;
When interior temperature reaches about 177 DEG C, start have water to distillate, continue to be warming up to 200 DEG C, when in receiving bottle to distillate the water yield be 53.6g time, esterification terminates.Continue to be warming up to 235 DEG C, steam unreacted alcohol and a small amount of water, carry out decompression polycondensation subsequently, system pressure remains on 300Pa, and in 1.5 hours reaction times, polycondensation terminates.Deactivation system vacuum state, under 230 DEG C and normal pressure, Microcrystalline Wax (5.48g) is added the product of step (2), constant temperature stirs 0.5 hour, obtains copolyester hot melt adhesive.Finally by reactant extruding pelletization, for use after freezing and pulverizing.Detect according to standard GB/T/T4608-84 and GB/T3682-2000 respectively, the first fusing point of this product is 48 DEG C, melting means is 21.6g/min.
Embodiment 2
In the polymerization reaction kettle of 2.5L with water distilling apparatus, add terephthalic acid (182.74g), m-phthalic acid (83.06g), neopentyl glycol (187.47g), ethylene glycol (70.76g) and poly(oxyethylene glycol) 400 (24.0g), titanium silicon composite catalyst (0.067g), heating, stir, when interior temperature reaches 136 DEG C, material starts fusing;
When interior temperature reaches about 181 DEG C, start have water to distillate, continue to be warming up to 198 DEG C, when in receiving bottle to distillate the water yield be 52.7g time, esterification terminates.Continue to be warming up to 239 DEG C, steam unreacted alcohol and a small amount of water, carry out decompression polycondensation subsequently, system pressure remains on 220Pa, and in 1.5 hours reaction times, polycondensation terminates.Deactivation system vacuum state, under 234 DEG C and normal pressure, by Microcrystalline Wax, (6.0 g) add the product of step (2), and constant temperature stirs 0.5 hour, obtains copolyester hot melt adhesive.Finally by reactant extruding pelletization, for use after freezing and pulverizing.
Detect according to standard GB/T/T4608-84 and GB/T3682-2000 respectively, the first fusing point of this product is 47 DEG C, melting means is 29.7g/min.
Embodiment 3
In the polymerization reaction kettle of 2.5L with water distilling apparatus, add terephthalic acid (199.32g), m-phthalic acid (66.44g), neopentyl glycol (187.47g), ethylene glycol (70.76g) and poly(oxyethylene glycol) 400 (24.0g), titanium silicon composite catalyst (0.164g), heating, stir, when interior temperature reaches 141 DEG C, material starts fusing;
When interior temperature reaches about 178 DEG C, start have water to distillate, continue to be warming up to 199 DEG C, when in receiving bottle to distillate the water yield be 54.6g time, esterification terminates.Continue to be warming up to 237 DEG C, steam unreacted alcohol and a small amount of water, carry out decompression polycondensation subsequently, system pressure remains on 130Pa, and in 1.2 hours reaction times, polycondensation terminates.Deactivation system vacuum state, under 232 DEG C and normal pressure, by Microcrystalline Wax, (2.98 g) add the product of step (2), and constant temperature stirs 0.25 hour, obtains copolyester hot melt adhesive.Finally by reactant extruding pelletization, for use after freezing and pulverizing.
Detect according to standard GB/T/T4608-84 and GB/T3682-2000 respectively, the first fusing point of this product is 50 DEG C, melting means is 20.7g/min
Embodiment 4
In the polymerization reaction kettle of 2.5L with water distilling apparatus, add terephthalic acid (199.32g), m-phthalic acid (66.44g), neopentyl glycol (171.85g), ethylene glycol (80.07g) and poly(oxyethylene glycol) 400 (24.0g), titanium silicon composite catalyst (0.135g), heating, stir, when interior temperature reaches 143 DEG C, material starts fusing;
When interior temperature reaches about 179 DEG C, start have water to distillate, continue to be warming up to 195 DEG C, when in receiving bottle to distillate the water yield be 54.2g time, esterification terminates.Continue to be warming up to 247 DEG C, steam unreacted alcohol and a small amount of water, carry out decompression polycondensation subsequently, system pressure remains on 80Pa, and in 1.5 hours reaction times, polycondensation terminates.Deactivation system vacuum state, under 236 DEG C and normal pressure, by Microcrystalline Wax, (3.32 g) add the product of step (2), and constant temperature stirs 0.35 hour, obtains copolyester hot melt adhesive.Finally by reactant extruding pelletization, for use after freezing and pulverizing.
Detect according to standard GB/T/T4608-84 and GB/T3682-2000 respectively, the first fusing point of this product is 46 DEG C, melting means is 28.4g/min
Embodiment 5
In the polymerization reaction kettle of 2.5L with water distilling apparatus, add terephthalic acid (182.74g), m-phthalic acid (83.05g), neopentyl glycol (171.85g), ethylene glycol (80.07g) and poly(oxyethylene glycol) 400 (24.0g), titanium silicon composite catalyst (0.163g), heating, stir, when interior temperature reaches 138 DEG C, material starts fusing;
When interior temperature reaches about 176 DEG C, start have water to distillate, continue to be warming up to 195 DEG C, when in receiving bottle to distillate the water yield be 53.8g time, esterification terminates.Continue to be warming up to 247 DEG C, steam unreacted
Alcohol and a small amount of water, carry out decompression polycondensation subsequently, system pressure remains on 50Pa, in 1.2 hours reaction times, polycondensation terminates.Introduce nitrogen deactivation system vacuum, under 245 DEG C and normal pressure, by Microcrystalline Wax, (6.20 g) add the product of step (2), and constant temperature stirs 0.5 hour, obtains copolyester hot melt adhesive.Finally by reactant extruding pelletization, for use after freezing and pulverizing.
Detect according to standard GB/T/T4608-84 and GB/T3682-2000 respectively, the first fusing point of this product is 49 DEG C, melting means is 30.2g/10min.
Claims (2)
1. a masking preparation method for modification terephthalic acid neopentyl glycol copolyester hot melt adhesive, is characterized in that comprising the steps:
(1) terephthalic acid, m-phthalic acid and neopentyl glycol, ethylene glycol, poly(oxyethylene glycol) 400 are at TiO
2/ SiO
2under composite catalyst effect, carry out esterification, temperature of reaction is 175 ~ 200 DEG C, and when the quantity of distillate of the water that esterification generates is 90 ~ 95% of theoretical amount, esterification terminates;
(2) continue to be warming up to 230 ~ 250 DEG C and carry out decompression polycondensation, reaction pressure is 50 ~ 300 Pa, and the time is 1.0 ~ 1.5 hours, obtains multipolymer;
(3) deactivation system vacuum state, under 220 ~ 245 DEG C and normal pressure, adds the product of step (2) by auxiliary agent, constant temperature stirs 0.25 ~ 0.5 hour, obtains masking modification terephthalic acid neopentyl glycol copolyester hot melt adhesive;
Described terephthalic acid, m-phthalic acid, ethylene glycol, mol ratio between neopentyl glycol and poly(oxyethylene glycol) 400 are respectively:
Terephthalic acid: m-phthalic acid=1.5: 0.5 ~ 1.5;
Terephthalic acid: neopentyl glycol=1.0: 0.5 ~ 1.5;
Neopentyl glycol: ethylene glycol: poly(oxyethylene glycol) 400=1.0: 0.5 ~ 1.0: 0.15 ~ 0.05;
The TiO of described catalyzer to be titanium silicon mol ratio be 9:1 ~ 2
2/ SiO
2composite catalyst, and the mass ratio of catalyzer and terephthalic acid is:
TiO
2/ SiO
2composite catalyst: terephthalic acid=0.025 ~ 0.050: 100.
2. method according to claim 1, is characterized in that, described auxiliary agent is selected from the one in paraffin and Microcrystalline Wax, and its quality added is 1.5% ~ 3.0% of terephthalic acid quality.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210393518.7A CN103725244B (en) | 2012-10-16 | 2012-10-16 | Method for preparing modified terephthalic acid neopentyl glycol copolyester hot melt adhesive for making membranes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210393518.7A CN103725244B (en) | 2012-10-16 | 2012-10-16 | Method for preparing modified terephthalic acid neopentyl glycol copolyester hot melt adhesive for making membranes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103725244A CN103725244A (en) | 2014-04-16 |
| CN103725244B true CN103725244B (en) | 2015-02-04 |
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|---|---|---|---|
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105077898B (en) * | 2015-08-19 | 2017-11-03 | 树业环保科技股份有限公司 | A kind of PET non-woven fabric shopping bags and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097548A (en) * | 1977-06-23 | 1978-06-27 | The Goodyear Tire & Rubber Company | Polyester-containing hot melt adhesive composition |
| CN102504746A (en) * | 2011-11-30 | 2012-06-20 | 上海天洋热熔胶有限公司 | Method for preparing PET (polyethylene terephthalate) copolyester hot melt adhesive for film preparation |
-
2012
- 2012-10-16 CN CN201210393518.7A patent/CN103725244B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097548A (en) * | 1977-06-23 | 1978-06-27 | The Goodyear Tire & Rubber Company | Polyester-containing hot melt adhesive composition |
| CN102504746A (en) * | 2011-11-30 | 2012-06-20 | 上海天洋热熔胶有限公司 | Method for preparing PET (polyethylene terephthalate) copolyester hot melt adhesive for film preparation |
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|---|---|
| CN103725244A (en) | 2014-04-16 |
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Address after: 201802 Shanghai City, Jiading District Hui Ping Road No. 505 Applicant after: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Applicant after: EAST CHINA University OF SCIENCE AND TECHNOLOGY Applicant after: KUNSHAN TIANYANG HOT MELT ADHESIVE Co.,Ltd. Address before: 201802 Shanghai City, Jiading District Hui Ping Road No. 505 Applicant before: Shanghai Tianyang Hotmelt Adhesives Co.,Ltd. Applicant before: EAST CHINA University OF SCIENCE AND TECHNOLOGY Applicant before: KUNSHAN TIANYANG HOT MELT ADHESIVE Co.,Ltd. |
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| COR | Change of bibliographic data |
Free format text: CORRECT: APPLICANT; FROM: SHANGHAI TIANYANG HOTMELT ADHESIVES CO., LTD. TO: SHANGHAI TIANYANG HOLT MELT ADHESIVE MATERIALS CO., LTD. |
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Address after: 201802 No. 505, Huiping Road, Jiading District, Shanghai Patentee after: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Patentee after: EAST CHINA University OF SCIENCE AND TECHNOLOGY Patentee after: Kunshan Tianyang New Material Co.,Ltd. Address before: 201802 No. 505, Huiping Road, Jiading District, Shanghai Patentee before: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Patentee before: EAST CHINA University OF SCIENCE AND TECHNOLOGY Patentee before: KUNSHAN TIANYANG HOT MELT ADHESIVE Co.,Ltd. |
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| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 201802 No. 505, Huiping Road, Jiading District, Shanghai Patentee after: Tianyang New Material (Shanghai) Technology Co.,Ltd. Patentee after: EAST CHINA University OF SCIENCE AND TECHNOLOGY Patentee after: Kunshan Tianyang New Material Co.,Ltd. Address before: 201802 No. 505, Huiping Road, Jiading District, Shanghai Patentee before: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Patentee before: EAST CHINA University OF SCIENCE AND TECHNOLOGY Patentee before: Kunshan Tianyang New Material Co.,Ltd. |