CN1138841C - Process for preparing polyester thermosol with high smelting point - Google Patents
Process for preparing polyester thermosol with high smelting point Download PDFInfo
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- CN1138841C CN1138841C CNB001197843A CN00119784A CN1138841C CN 1138841 C CN1138841 C CN 1138841C CN B001197843 A CNB001197843 A CN B001197843A CN 00119784 A CN00119784 A CN 00119784A CN 1138841 C CN1138841 C CN 1138841C
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- CN
- China
- Prior art keywords
- acid
- ester
- manufacture method
- smelting point
- high smelting
- Prior art date
- 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.)
- Expired - Lifetime
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- 229920000728 polyester Polymers 0.000 title claims abstract description 24
- 238000003723 Smelting Methods 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 21
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 16
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 238000005886 esterification reaction Methods 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000006837 decompression Effects 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 239000003381 stabilizer Substances 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 230000032050 esterification Effects 0.000 claims description 11
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 10
- -1 isophthalic acid ester Chemical class 0.000 claims description 9
- 238000005809 transesterification reaction Methods 0.000 claims description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 6
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- 150000007520 diprotic acids Chemical class 0.000 claims description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- 229940051250 hexylene glycol Drugs 0.000 claims description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 238000013019 agitation Methods 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229940067597 azelate Drugs 0.000 claims description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical group 0.000 claims description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 2
- 238000003756 stirring Methods 0.000 abstract description 7
- 238000002425 crystallisation Methods 0.000 abstract description 4
- 230000008025 crystallization Effects 0.000 abstract description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 12
- 238000006068 polycondensation reaction Methods 0.000 description 9
- 239000004831 Hot glue Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000693 micelle Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 4
- 239000002390 adhesive tape Substances 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Abstract
The present invention relates to a method for preparing polyester thermosol with a high smelting point. The present invention comprises follow processing steps that dibasic acid ester and dihydric alcohol are heated and stirred to carry out ester interchange under action of a catalyst; then, other dicarboxylic acids, catalysts and stabilizing agents are added to further carry out esterification reaction; finally, copolycondensation is carry out under conditions of decompression, heating and stirring to obtain product. Compared with the prior art, the present invention has the advantages of reasonable process, high crystallization velocity, short curing time, etc., and the obtained product can be applied under a high temperature condition.
Description
The present invention relates to the manufacture method of tackiness agent, relate in particular to a kind of manufacture method of the polyester thermosol with high smelting point based on the organic polymer composition
At present, the unit that be engaged in the polyester thermosol with high smelting point development, develops is less relatively.From prior art, the fusing point of the polyester hot-melt adhesive of developing all lower (being no more than 130 ℃), thereby can not under hot environment, use.In addition, the crystallization rate and the curing speed of the polyester hot-melt adhesive that prior art is made are slower, are unfavorable for finishing fast on the bonding production line at needs using.
Purpose of the present invention be exactly provide a kind of adaptation under hot conditions, to use in order to overcome the defective that above-mentioned prior art exists, the manufacture method of crystallization velocity is fast, lack set time polyester thermosol with high smelting point.
Technical solution of the present invention is: the manufacture method of polyester thermosol with high smelting point comprises following processing step: earlier with diester and dibasic alcohol under catalyst action, heated and stirred is carried out transesterify, the pure still temperature that goes out of this transesterification reaction is 145～200 ℃; And then the di-carboxylic acid, catalyzer and the stablizer that add other carry out further esterification, and it is 180～210 ℃ that this esterification distillates water still temperature; At last, carry out copolycondensation under decompression, heating, agitation condition, the high temperature section of this copolycondensation is 240～255 ℃, and the overbottom pressure in the system is for being lower than 133Pa, thereby makes polyester thermosol with high smelting point.
Described diester has: terephthalate, isophthalic acid ester, phthalic ester, adipic acid ester, azelate, sebate.
Described dibasic alcohol has: ethylene glycol, propylene glycol, butyleneglycol, hexylene glycol, glycol ether, Triethylene glycol.
Described di-carboxylic acid has: terephthalic acid, m-phthalic acid, phthalic acid, hexanodioic acid, nonane diacid, sebacic acid.
Described diprotic acid (ester) is preferable to mix use aromatic series and aliphatic diprotic acid (ester).
Used catalyzer is a titanate ester in described transesterify, esterification, the copolycondensation, as: the positive ethyl ester of metatitanic acid, isopropyl titanate, tetrabutyl titanate.
Used stablizer is a phosphoric acid ester in described esterification, the copolycondensation, as trimethyl phosphite 99, triphenyl phosphite.
Used dibasic alcohol, diprotic acid (ester) ratio are that the weight ratio of alcohol and acid (ester) is 40-60: 60-40.
In the used mixed dibasic acid (ester), the weight ratio of aromatic series and aliphatic dibasic acid (ester) is 80-99: 20-1.
Described catalyzer, stabilizing agent dosage be starting monomer weight 0.025% to 0.075% between.
Compared with prior art, the present invention has following positively effect:
1. the polyester hot-melt adhesive of the used technology manufacturing of the present invention has the high-melting-point more than 160 ℃, with this type of gluing bond that connects, the test of the environment that stands up to high temperatures, is the present less hot melt adhesive kind that can at high temperature use.
2. the polyester hot-melt adhesive crystallization velocity of the used technology manufacturing of the present invention is fast, help further being processed into sizing material with different geometries, and because its short (promptly curable in the several seconds usually), use so be particularly suitable for finishing fast on the bonding production line at needs set time.
Below in conjunction with embodiment, the invention will be further described.
Embodiment 1
Transesterification reaction:
In there-necked flask, add dimethyl terephthalate (DMT) 198g, 1,4-butyleneglycol 162g, the positive ethyl ester 0.23g of glycol ether 64g and catalyzer metatitanic acid, heating, material begins fusing when 100 ℃ of bottle Nei Wenduda, begins then to stir; When being warmed up to 145 ℃ of left and right sides, begin to occur drop, distillate methyl alcohol, till temperature reaches about 200 ℃ in continuing to be warming up to.When methyl alcohol to be distillated reached theoretical amount, transesterification reaction was finished, and stopped heating, cooling.
Esterification and polycondensation:
When below the temperature drop to 100 in the above-mentioned there-necked flask ℃, promptly add m-phthalic acid 20g, hexanodioic acid 9.2g, and add stablizer triphenyl phosphite 0.2g stirs then and heats up, and when about interior temperature rise to 180 ℃, has water to distillate.Continue to be warmed up to 210 ℃, after the water quantity of distillate reaches theoretical value, continue progressively to steam unreacted pure and mild oligopolymer, when the speed of distillating is slack-off,, to impel polycondensation to carry out interior temperature rise to 250 ℃ with the decompression of decompression water pump.When distillate seldom the time, system is connected high vacuum, overbottom pressure is kept less than 133Pa (1mmHg), and continue reaction about 2 hours down at 250～255 ℃, promptly finish polycondensation.Logical nitrogen is removed vacuum, while hot molten polymer is poured in the cold water, obtains white adhesive tape, is cut into micelle, and the fusing point of this micelle is 160～170 ℃, and specific viscosity is 0.38～0.43.
Embodiment 2
Transesterification reaction:
In there-necked flask, add dimethyl terephthalate (DMT) 139.7g, 1,4-butyleneglycol 180g, and the positive butyl ester 0.20g of catalyzer metatitanic acid, heating, when 100 ℃ of bottle Nei Wenda, material begins fusing, promptly begins to stir, when being warmed up to 150 ℃ of left and right sides, begin to occur drop, distillate methyl alcohol, till continuation heats up about Nei Wenda is 200 ℃.When methyl alcohol to be distillated reached theoretical amount, transesterification reaction was finished, and stopped heating, cooling.
Esterification and polycondensation:
Below temperature drop to 100 in the above-mentioned there-necked flask ℃, promptly add m-phthalic acid 26g, hexanodioic acid 26.3g, and add stablizer triphenyl phosphite 0.2g, stir then and heat up.When about interior temperature rise to 180 ℃, there is water to distillate, continue to be warmed up to about 210 ℃, after the water quantity of distillate reaches theoretical value, continue progressively with interior temperature rise to 240 ℃, to steam unreacted pure and mild oligopolymer.When the speed of distillating is slack-off,, impel polycondensation to carry out with the decompression of decompression water pump, when distillate seldom the time, system is connected high vacuum, keep overbottom pressure less than 133Pa (1mmHg), and under 240～250 ℃, continue reaction about 2 hours, finish polycondensation, logical nitrogen, remove vacuum, while hot molten polymer is poured in the cold water, obtained white adhesive tape, be cut into micelle, this micelle fusing point is 180～190 ℃, and specific viscosity is 0.37～0.42.
Embodiment 3
Transesterification reaction:
In there-necked flask, add dimethyl terephthalate (DMT) 175g, 1,4-butyleneglycol 144g, 1, the positive butyl ester 0.20g of 6-hexylene glycol 47g and catalyzer metatitanic acid, heating, when 100 ℃ of bottle Nei Wenda, material begins fusing, promptly begins to stir, when being warmed up to 150 ℃ of left and right sides, begin to occur drop, distillate methyl alcohol, till continuing to heat up about Nei Wenda is 200 ℃, when methyl alcohol to be distillated reached theoretical amount, transesterification reaction finished, cooling.
Esterification and polycondensation:
Below temperature drop to 100 within the above-mentioned there-necked flask ℃, promptly add m-phthalic acid 8.5g, sebacic acid 5.0g, and add stablizer triphenyl phosphite 0.2g stirs then and heats up, and when about interior temperature rise to 180 ℃, has water to distillate.Continue to be warming up to about 210 ℃, after the water quantity of distillate reaches theoretical value, continue progressively with interior temperature rise to 250 ℃, to steam unreacted pure and mild oligopolymer, when the speed of distillating is slack-off, with the decompression of decompression water pump, impel polycondensation to carry out,, system is connected high vacuum when distillate seldom the time, make overbottom pressure keep continuing reaction about 2 hours down, finish polycondensation less than 133Pa (1mmHg) and at 250-255 ℃.Logical nitrogen is removed vacuum, while hot molten polymer is poured in the cold water, obtains white adhesive tape, is cut into micelle, and this micelle fusing point is 192～197 ℃, and specific viscosity is 0.36～0.46.
The various polyester thermosol with high smelting point that makes according to the foregoing description, can extrude by screw rod and be processed into strip or film like hot melt adhesive product with degree of precision external diameter or thickness, and can be used as the temperature tolerance hot melt adhesive, finish fast on the bonding various production lines at needs and use.
Claims (10)
1. the manufacture method of polyester thermosol with high smelting point is characterized in that, comprises following processing step: earlier with diester and dibasic alcohol under catalyst action, heated and stirred is carried out transesterify, the pure still temperature that goes out of this transesterification reaction is 145～200 ℃; And then add di-carboxylic acid, catalyzer and stablizer and carry out further esterification, it is 180～210 ℃ that this esterification distillates water still temperature; At last, carry out copolycondensation under decompression, heating, agitation condition, the high temperature section of this copolycondensation is 240～255 ℃, and the overbottom pressure in the system is for being lower than 133Pa, thereby makes polyester thermosol with high smelting point.
2. the manufacture method of polyester thermosol with high smelting point according to claim 1 is characterized in that, described diester has: terephthalate, isophthalic acid ester, phthalic ester, adipic acid ester, azelate, sebate.
3. the manufacture method of polyester thermosol with high smelting point according to claim 1 is characterized in that, described dibasic alcohol has: ethylene glycol, propylene glycol, butyleneglycol, hexylene glycol, glycol ether, Triethylene glycol.
4. the manufacture method of polyester thermosol with high smelting point according to claim 1 is characterized in that, described di-carboxylic acid has: terephthalic acid, m-phthalic acid, phthalic acid, hexanodioic acid, nonane diacid, sebacic acid.
5. according to the manufacture method of claim 2 or 4 described polyester thermosol with high smelting point, it is characterized in that described diprotic acid (ester) is preferable to mix use aromatic series and aliphatic diprotic acid (ester).
6. the manufacture method of polyester thermosol with high smelting point according to claim 1 is characterized in that, used catalyzer is a titanate ester in described transesterify, esterification, the copolycondensation, comprises the positive ethyl ester of metatitanic acid, isopropyl titanate, tetrabutyl titanate.
7. the manufacture method of polyester thermosol with high smelting point according to claim 1 is characterized in that, used stablizer is a phosphoric acid ester in described esterification, the copolycondensation, comprises trimethyl phosphite 99, triphenyl phosphite.
8. the manufacture method of polyester thermosol with high smelting point according to claim 1 is characterized in that, used dibasic alcohol, diprotic acid (ester) ratio are that the weight ratio of alcohol and acid (ester) is 40-60: 60-40.
9. the manufacture method of polyester thermosol with high smelting point according to claim 5 is characterized in that, in the used mixed dibasic acid (ester), the weight ratio of aromatic series and aliphatic dibasic acid (ester) is 80-99: 20-1.
10. the manufacture method of polyester thermosol with high smelting point according to claim 1 is characterized in that, described catalyzer, stabilizing agent dosage be starting monomer weight 0.025% to 0.075% between.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB001197843A CN1138841C (en) | 2000-08-29 | 2000-08-29 | Process for preparing polyester thermosol with high smelting point |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB001197843A CN1138841C (en) | 2000-08-29 | 2000-08-29 | Process for preparing polyester thermosol with high smelting point |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1340585A CN1340585A (en) | 2002-03-20 |
| CN1138841C true CN1138841C (en) | 2004-02-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB001197843A Expired - Lifetime CN1138841C (en) | 2000-08-29 | 2000-08-29 | Process for preparing polyester thermosol with high smelting point |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1138841C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110041514A (en) * | 2019-05-13 | 2019-07-23 | 无锡风鹏新材料科技有限公司 | A kind of lower glass transition temperatures, dystectic tough polyesters plastics and preparation method thereof |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308410C (en) * | 2005-11-14 | 2007-04-04 | 上海轻工业研究所有限公司 | Composition of polyester hot-melt adhesive in low melting viscosity |
| CN1990809B (en) * | 2005-12-28 | 2011-05-04 | 上海轻工业研究所有限公司 | Polyester thermosol and preparation method thereof |
| CN101126006B (en) * | 2007-06-29 | 2010-05-19 | 上海天洋热熔胶有限公司 | Method for preparing polyester thermosol |
| CN100439466C (en) * | 2007-06-29 | 2008-12-03 | 上海天洋热熔胶有限公司 | Polyester thermosol and preparation method thereof |
| CN103013415B (en) | 2012-12-28 | 2013-12-04 | 昆山天洋热熔胶有限公司 | Semi-interpenetrating-network-structure polyester/polyvinyl aldehyde hot-melt adhesive and preparation technique thereof |
| CN105348497B (en) | 2015-12-07 | 2018-01-02 | 上海天洋热熔粘接材料股份有限公司 | A kind of novel copolymerized ester PUR and preparation method thereof |
| CN108997570B (en) * | 2018-07-28 | 2020-09-15 | 广东舜天新材料有限公司 | Dimer acid modified copolyester hot melt adhesive and preparation method thereof |
-
2000
- 2000-08-29 CN CNB001197843A patent/CN1138841C/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110041514A (en) * | 2019-05-13 | 2019-07-23 | 无锡风鹏新材料科技有限公司 | A kind of lower glass transition temperatures, dystectic tough polyesters plastics and preparation method thereof |
| CN110041514B (en) * | 2019-05-13 | 2021-05-25 | 无锡风鹏新材料科技有限公司 | Tough polyester plastic with low glass transition temperature and high melting point and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1340585A (en) | 2002-03-20 |
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