CN102102003A - Polyester hot melt adhesive for making films and preparation method thereof - Google Patents
Polyester hot melt adhesive for making films and preparation method thereof Download PDFInfo
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- CN102102003A CN102102003A CN 201010588468 CN201010588468A CN102102003A CN 102102003 A CN102102003 A CN 102102003A CN 201010588468 CN201010588468 CN 201010588468 CN 201010588468 A CN201010588468 A CN 201010588468A CN 102102003 A CN102102003 A CN 102102003A
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Abstract
The invention discloses a method for preparing a polyester hot melt adhesive for making films, which comprises the following steps of: (1) adding terephthalic acid, butanediol and a titanium catalyst into an esterification kettle for primary esterification, wherein the reaction temperature is 170-195DEG C; (2) adding adipic acid, maleic acid, isophthalic acid, propylene glycol, neopentyl glycol and a p-toluenesulfonic acid catalyst into the kettle for secondary esterification, wherein the reaction temperature is 180-205DEG C; and (3) adding a stabilizing agent, and performing polycondensation under reduced pressure to obtain the polyester hot melt adhesive product which is quick in crystallization and easily forms a film.
Description
Technical field
The present invention relates to a kind of preparation method who makes the polyester for film hot melt adhesive, it is fast and be easy to film forming preparation method of polyester hot melt adhesive to relate in particular to a kind of crystallization velocity.
Background technology
Polyester hot-melt adhesive has heat-resistingly, cold-resistant, water-fast to be washed, advantages such as bonding strength is good, good insulation preformance, be mainly used in fabric processing, carpet backing, clothes processing, shoe industry etc., this external packing, heat-sealing, composite membrane, trolley part assembling, strongthener, electrical apparatus industry also are applied.
Polyester is to contain ester group (general name CO-O-) on the main polymer chain, be divided into unsaturated polyester and thermoplastically polyester two big classes, from molecular structure, introduce phenyl in the molecule straight chain of saturated polyester and will improve its fusing point, tensile strength and thermotolerance, introduce alkyl and ehter bond and will improve melt viscosity, flexibility and snappiness, but this molecular structure also has high crystalline, and wetting property and consolidation strength are relatively poor.Therefore adding some acids or alcohols usually when synthetic replaces a part of original monomer, makes it carry out random polymerization, thereby destroys crystallinity, improves wetting property and consolidation strength.At present, polyester hot-melt adhesive is made by polyprotonic acid and polyol reaction usually, is raw material with dimethyl terephthalate (DMT), m-phthalic acid, hexylene glycol and butyleneglycol etc. usually.U.S. Pat 6,255,443 propose to have synthesized a kind of copolyester with low melting point hot melt adhesive with ester-interchange method; Japanese Patent JP2007254702 (A) proposes to have synthesized polyester hot-melt adhesive with terephthalic acid and ethylene glycol etc.; U.S. Pat 20080230749A1 has proposed a kind of preparation method of polyester hot melt adhesive that is exclusively used in electron trade.But aforesaid method synthetic polyester hot-melt adhesive is not that its film forming properties is all not ideal for the system film designs.
Summary of the invention
The present invention is intended to disclose a kind of system polyester for film hot melt adhesive and preparation method thereof, and the molten finger of gained polyester hot-melt adhesive is higher, and crystallization velocity is very fast, and the open hour are short, has overcome the defective that prior art exists.
Design of the present invention is such:
In order to achieve the above object, dibasic alcohol such as diprotic acid and butyleneglycol such as the present invention imagines and uses terephthalic acid, hexanodioic acid, propylene glycol are earlier after twice esterification, polycondensation obtain system polyester for film hot melt adhesive.
Method of the present invention comprises the steps:
(1) terephthalic acid and butyleneglycol and Titanium series catalyst are added in the esterifying kettle by a certain percentage, carry out an esterification, temperature of reaction is 170～195 ℃, discharges the water that reaction generates simultaneously; Described Titanium series catalyst is selected from Ti (OC
2H
5)
4, Ti (OC
3H
7)
4Or Ti (OC
4H
9)
4In a kind of;
After (2) esterifications finish, add hexanodioic acid, maleic acid, m-phthalic acid and propylene glycol, neopentyl glycol and catalyzer tosic acid in the still by a certain percentage again, carry out the secondary esterification, temperature of reaction is 180～205 ℃, discharges the water that reaction generates simultaneously; Add stablizer again, the decompression polycondensation, temperature is 220～245 ℃, and keeps 1.0～2.0 hours, can obtain to make polyester for film hot melt adhesive product;
The ratio of described whole diprotic acid and dibasic alcohol total mole number is 1: 1.1～1.3; Wherein, in whole diprotic acid, the mole fraction of terephthalic acid, hexanodioic acid, maleic acid, m-phthalic acid is respectively 0.45～0.55,0.3～0.45,0.01～0.1,0.01～0.1; In whole dibasic alcohol, the mole fraction of butyleneglycol, propylene glycol, neopentyl glycol is respectively 0.75～0.90,0.05～0.15,0.05～0.15.
The mol ratio of described Titanium series catalyst and tosic acid and terephthalic acid is respectively 0.0001～0.0008: 1.0 and 0.0001～0.0006: 1.0.
Described stablizer is selected from triphenyl phosphite, tributyl phosphate, and its consumption is 0.0002～0.0004 of whole diprotic acid gross weights.
Pressure-controlling is at 100Pa～180Pa during described decompression polycondensation.
Described esterifying kettle has rectifying column and reflux exchanger, and the water that reaction generates is by rectificating method discharge simultaneously; The rectifying column tower top temperature of (1) esterification of step is controlled at 95～103 ℃, and reflux ratio is 2～4; The rectifying column tower top temperature of step (2) secondary esterification is controlled at 96～105 ℃, and reflux ratio is 2～4.
The substantive progressive following aspect that is embodied in of the present invention:
The present invention adopts Titanium series catalyst and Catalyzed by p-Toluenesulfonic Acid agent, make terephthalic acid, diprotic acid such as hexanodioic acid and dibasic alcohol direct esterification under lower temperature generate corresponding ester, have avoided the generation of by-product methyl alcohol, have reduced the cyclisation rate of butyleneglycol simultaneously, not only help environment, and reduced cost, and the molten finger of synthetic polyester hot-melt adhesive is higher, and crystallization velocity is very fast, open hour are short, and film forming properties is good.
Embodiment
Embodiment 1
With terephthalic acid (74.7g) and butyleneglycol (89.1g) and Titanium series catalyst Ti (OC
2H
5)
4(0.031g) add in the 1.0L esterifying kettle, this still has stirring, temp measuring system and rectifying column and reflux exchanger, the control temperature in the kettle is 170～175 ℃ and carries out an esterification under normal pressure, the water that is generated reclaims through distillation system, the rectifying reflux ratio is 3.0, the capital vapor phase temperature is 95～98 ℃, continues reaction when the capital vapor phase temperature obviously descends, and one time esterification finishes.
With hexanodioic acid (62.8g), maleic acid (8.12g), m-phthalic acid (8.30g) and propylene glycol (4.18g), neopentyl glycol (5.72g) and catalyzer tosic acid (0.039g) add in the still, carry out the secondary esterification, temperature of reaction is 180～185 ℃, the reflux ratio and the temperature of distillation system are the same, after treating that the secondary esterification finishes, add stablizer tributyl phosphate (0.046g), the polycondensation of reducing pressure, temperature of reaction is 220 ℃, the still internal pressure progressively is decreased to 130Pa, and kept 2 hours, polycondensation finishes, and feeds nitrogen discharging while hot, and polymkeric substance is poured in the cold water, get bar-shaped adhesive tape, be cut into micelle.
Adopting its molecular-weight average of gel chromatography is 25300, after promoting crystallization under 60 ℃, recording its final temperature of fusion with DSC is 124 ℃, detect according to standard GB/T3682-2000, GB/T2794-1995 respectively, this product records melting index under 160 ℃ be 50.7g/10min.
Embodiment 2
With terephthalic acid (88.0g) and butyleneglycol (90.7g) and Titanium series catalyst Ti (OC
3H
7)
4(0.105g) add in the 1.0L esterifying kettle, this still has stirring, temp measuring system and rectifying column and reflux exchanger, the control temperature in the kettle is 175～180 ℃ and carries out an esterification under normal pressure, the water that is generated reclaims through distillation system, the rectifying reflux ratio is 2.0, the capital vapor phase temperature is 96～99 ℃, continues reaction when the capital vapor phase temperature obviously descends, and one time esterification finishes.
With hexanodioic acid (43.8g), maleic acid (11.6g), m-phthalic acid (11.6g) and propylene glycol (7.30g), neopentyl glycol (9.98g) and catalyzer tosic acid (0.010g) add in the still, carry out the secondary esterification, temperature of reaction is 185～190 ℃, the reflux ratio and the temperature of distillation system are the same, after treating that the secondary esterification finishes, add stablizer triphenyl phosphite (0.031g), the polycondensation of reducing pressure, temperature of reaction is 230 ℃, the still internal pressure progressively is decreased to 150Pa, and kept 1 hour, polycondensation finishes, and feeds nitrogen discharging while hot, and polymkeric substance is poured in the cold water, get bar-shaped adhesive tape, be cut into micelle.
Adopting its molecular-weight average of gel chromatography is 23800, after promoting crystallization under 60 ℃, recording its final temperature of fusion with DSC is 121 ℃, detect according to standard GB/T3682-2000, GB/T2794-1995 respectively, this product records melting index under 160 ℃ be 55.8g/10min.
Embodiment 3
With terephthalic acid (91.3g) and butyleneglycol (84.2g) and Titanium series catalyst Ti (OC
3H
7)
4(0.125g) add in the 1.0L esterifying kettle, this still has stirring, temp measuring system and rectifying column and reflux exchanger, the control temperature in the kettle is 180～185 ℃ and carries out an esterification under normal pressure, the water that is generated reclaims through distillation system, the rectifying reflux ratio is 4.0, the capital vapor phase temperature is 98～101 ℃, continues reaction when the capital vapor phase temperature obviously descends, and one time esterification finishes.
With hexanodioic acid (58.4g), maleic acid (4.64g), m-phthalic acid (1.66g) and propylene glycol (13.7g), neopentyl glycol (8.74g) and catalyzer tosic acid (0.019g) add in the still, carry out the secondary esterification, temperature of reaction is 190～195 ℃, the reflux ratio and the temperature of distillation system are the same, after treating that the secondary esterification finishes, add stablizer tributyl phosphate (0.047g), the polycondensation of reducing pressure, temperature of reaction is 235 ℃, the still internal pressure progressively is decreased to 100Pa, and keep about 1 hour, polycondensation finishes, and feeds nitrogen discharging while hot, and polymkeric substance is poured in the cold water, get bar-shaped adhesive tape, be cut into micelle.
Adopting its molecular-weight average of gel chromatography is 28400, after promoting crystallization under 60 ℃, recording its final temperature of fusion with DSC is 128 ℃, detect according to standard GB/T3682-2000, GB/T2794-1995 respectively, this product records melting index under 160 ℃ be 41.8g/10min.
Embodiment 4
With terephthalic acid (79.7g) and butyleneglycol (81.0g) and Titanium series catalyst Ti (OC
4H
9)
4(0.016g) add in the 1.0L esterifying kettle, this still has stirring, temp measuring system and rectifying column and reflux exchanger, the control temperature in the kettle is 185～190 ℃ and carries out an esterification under normal pressure, the water that is generated reclaims through distillation system, the rectifying reflux ratio is 2.8, the capital vapor phase temperature is 101～103 ℃, continues reaction when the capital vapor phase temperature obviously descends, and one time esterification finishes.
With hexanodioic acid (52.6g), maleic acid (4.64g), m-phthalic acid (16.6g) and propylene glycol (11.9g), neopentyl glycol (15.0g) and catalyzer tosic acid (0.066) add in the still, carry out the secondary esterification, temperature of reaction is 195～200 ℃, the reflux ratio and the temperature of distillation system are the same, after treating that the secondary esterification finishes, add stablizer triphenyl phosphite (0.046g), the polycondensation of reducing pressure, temperature of reaction is 240 ℃, the still internal pressure progressively is decreased to 180Pa, and kept 1.5 hours, polycondensation finishes, and feeds nitrogen discharging while hot, and polymkeric substance is poured in the cold water, get bar-shaped adhesive tape, be cut into micelle.
Adopting its molecular-weight average of gel chromatography is 21400, after promoting crystallization under 60 ℃, recording its final temperature of fusion with DSC is 117 ℃, detect according to standard GB/T3682-2000, GB/T2794-1995 respectively, this product records melting index under 160 ℃ be 61.2g/10min.
Embodiment 5
With terephthalic acid (83.0g) and butyleneglycol (91.3g) and Titanium series catalyst Ti (OC
2H
5)
4(0.046g) add in the 1.0L esterifying kettle, this still has stirring, temp measuring system and rectifying column and reflux exchanger, the control temperature in the kettle is 190～195 ℃ and carries out an esterification under normal pressure, the water that is generated reclaims through distillation system, the rectifying reflux ratio is 3.2, the capital vapor phase temperature is 102～105 ℃, continues reaction when the capital vapor phase temperature obviously descends, and one time esterification finishes.
With hexanodioic acid (65.7g), maleic acid (1.16g), m-phthalic acid (6.64g) and propylene glycol (6.92g), neopentyl glycol (20.3g) and catalyzer tosic acid (0.034g) add in the still, carry out the secondary esterification, temperature of reaction is 200～205 ℃, the reflux ratio and the temperature of distillation system are the same, after treating that the secondary esterification finishes, add stablizer tributyl phosphate (0.063g), the polycondensation of reducing pressure, temperature of reaction is 245 ℃, the still internal pressure progressively is decreased to 120Pa, and kept 2 hours, polycondensation finishes, and feeds nitrogen discharging while hot, and polymkeric substance is poured in the cold water, get bar-shaped adhesive tape, be cut into micelle.
Adopting its molecular-weight average of gel chromatography is 27100, after promoting crystallization under 60 ℃, recording its final temperature of fusion with DSC is 126 ℃, detect according to standard GB/T3682-2000, GB/T2794-1995 respectively, this product records melting index under 160 ℃ be 46.5g/10min.
Claims (4)
1. system polyester for film hot melt adhesive and preparation method thereof is characterized in that, comprises the steps:
(1) terephthalic acid and butyleneglycol and Titanium series catalyst are added in the esterifying kettle by a certain percentage, carry out an esterification, temperature of reaction is 170～195 ℃, discharges the water that reaction generates simultaneously; Described Titanium series catalyst is selected from Ti (OC
2H
5)
4, Ti (OC
3H
7)
4Or Ti (OC
4H
9)
4In a kind of;
After (2) esterifications finish, add hexanodioic acid, maleic acid, m-phthalic acid and propylene glycol, neopentyl glycol and catalyzer tosic acid in the still by a certain percentage again, carry out the secondary esterification, temperature of reaction is 180～205 ℃, discharges the water that reaction generates simultaneously; Add stablizer again, the decompression polycondensation, temperature is 220～245 ℃, and keeps 1.0～2.0 hours, can obtain to make polyester for film hot melt adhesive product;
The ratio of described whole diprotic acid and dibasic alcohol total mole number is 1: 1.1～1.3; Wherein, in whole diprotic acid, the mole fraction of terephthalic acid, hexanodioic acid, maleic acid, m-phthalic acid is respectively 0.45～0.55,0.3～0.45,0.01～0.1,0.01～0.1; In whole dibasic alcohol, the mole fraction of butyleneglycol, propylene glycol, neopentyl glycol is respectively 0.75～0.90,0.05～0.15,0.05～0.15.
2. method according to claim 1 is characterized in that, the mol ratio of Titanium series catalyst and tosic acid and terephthalic acid is respectively 0.0001～0.0008: 1.0 and 0.0001～0.0006: 1.0.
3. method according to claim 1 is characterized in that said stablizer is selected from triphenyl phosphite, tributyl phosphate, and its consumption is 0.0002～0.0004 of whole diprotic acid gross weights.
4. method according to claim 1 is characterized in that, pressure-controlling is at 100Pa～180Pa during the decompression polycondensation.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105884689A CN102102003B (en) | 2010-12-14 | 2010-12-14 | Polyester hot melt adhesive for making films and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105884689A CN102102003B (en) | 2010-12-14 | 2010-12-14 | Polyester hot melt adhesive for making films and preparation method thereof |
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| Publication Number | Publication Date |
|---|---|
| CN102102003A true CN102102003A (en) | 2011-06-22 |
| CN102102003B CN102102003B (en) | 2012-08-15 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103421460A (en) * | 2013-07-03 | 2013-12-04 | 上海天洋热熔胶有限公司 | Preparation method of crystalloid and transparent copolyester hot melt adhesive with high melting point |
| CN104479118A (en) * | 2014-12-23 | 2015-04-01 | 安徽助成信息科技有限公司 | Method for preparing PNT (para nitro toluene) copolyester hot melt adhesive used for film manufacturing |
| CN105348497A (en) * | 2015-12-07 | 2016-02-24 | 上海天洋热熔粘接材料股份有限公司 | Novel copolyster hot melt adhesive and preparation method thereof |
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| CN101126006A (en) * | 2007-06-29 | 2008-02-20 | 上海天洋热熔胶有限公司 | Method for preparing polyester thermosol |
| CN101353562A (en) * | 2007-07-25 | 2009-01-28 | 比亚迪股份有限公司 | Preparation of polyester hot-melt adhesive |
| CN101705070A (en) * | 2009-11-13 | 2010-05-12 | 上海天洋热熔胶有限公司 | Method for preparing quickly-crystallized polyester hot melt adhesive |
| CN101724369A (en) * | 2009-11-13 | 2010-06-09 | 上海天洋热熔胶有限公司 | Preparation method of high-performance polyester hot melt adhesive |
-
2010
- 2010-12-14 CN CN2010105884689A patent/CN102102003B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101126006A (en) * | 2007-06-29 | 2008-02-20 | 上海天洋热熔胶有限公司 | Method for preparing polyester thermosol |
| CN101353562A (en) * | 2007-07-25 | 2009-01-28 | 比亚迪股份有限公司 | Preparation of polyester hot-melt adhesive |
| CN101705070A (en) * | 2009-11-13 | 2010-05-12 | 上海天洋热熔胶有限公司 | Method for preparing quickly-crystallized polyester hot melt adhesive |
| CN101724369A (en) * | 2009-11-13 | 2010-06-09 | 上海天洋热熔胶有限公司 | Preparation method of high-performance polyester hot melt adhesive |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103421460A (en) * | 2013-07-03 | 2013-12-04 | 上海天洋热熔胶有限公司 | Preparation method of crystalloid and transparent copolyester hot melt adhesive with high melting point |
| CN104479118A (en) * | 2014-12-23 | 2015-04-01 | 安徽助成信息科技有限公司 | Method for preparing PNT (para nitro toluene) copolyester hot melt adhesive used for film manufacturing |
| CN105348497A (en) * | 2015-12-07 | 2016-02-24 | 上海天洋热熔粘接材料股份有限公司 | Novel copolyster hot melt adhesive and preparation method thereof |
| WO2017097157A1 (en) * | 2015-12-07 | 2017-06-15 | 上海天洋热熔粘接材料股份有限公司 | Novel copolyester hot-melt adhesive and preparation method therefor |
| US10501666B2 (en) | 2015-12-07 | 2019-12-10 | Shanghai Tianyang Hot Melt Adhesive Co., Ltd | Copolyester hot-melt adhesive and preparation method therefor |
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Owner name: SHANGHAI TIANYANG HEAT FUSION BONDING MATERIAL CO. Free format text: FORMER NAME: SHANGHAI TIANYANG HOTMELT ADHESIVES CO., LTD. |
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Address after: 201802 Shanghai City, Jiading District Hui Ping Lu Nanxiang Town, No. 505 Patentee after: Shanghai Tianyang hot melt adhesive materials Limited by Share Ltd. Patentee after: EAST CHINA University OF SCIENCE AND TECHNOLOGY Address before: 201802 Shanghai City, Jiading District Hui Ping Lu Nanxiang Town, No. 505 Patentee before: Shanghai Tianyang Hotmelt Adhesives Co.,Ltd. Patentee before: East China University of Science and Technology |
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Address after: 201802 Shanghai City, Jiading District Hui Ping Lu Nanxiang Town, No. 505 Patentee after: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Patentee after: EAST CHINA University OF SCIENCE AND TECHNOLOGY Address before: 201802 Shanghai City, Jiading District Hui Ping Lu Nanxiang Town, No. 505 Patentee before: Shanghai Tianyang hot melt adhesive materials Limited by Share Ltd. Patentee before: East China University of Science and Technology |
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Address after: 201802 Shanghai City, Jiading District Hui Ping Lu Nanxiang Town, No. 505 Patentee after: Tianyang New Material (Shanghai) Technology Co.,Ltd. Patentee after: EAST CHINA University OF SCIENCE AND TECHNOLOGY Address before: 201802 Shanghai City, Jiading District Hui Ping Lu Nanxiang Town, No. 505 Patentee before: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Patentee before: EAST CHINA University OF SCIENCE AND TECHNOLOGY |