CN103183816A - Solvent resistance polyester polyol synthesizing method - Google Patents
Solvent resistance polyester polyol synthesizing method Download PDFInfo
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- CN103183816A CN103183816A CN2013101376775A CN201310137677A CN103183816A CN 103183816 A CN103183816 A CN 103183816A CN 2013101376775 A CN2013101376775 A CN 2013101376775A CN 201310137677 A CN201310137677 A CN 201310137677A CN 103183816 A CN103183816 A CN 103183816A
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- Prior art keywords
- polyester polyol
- temperature
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- synthetic method
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- 229920005906 polyester polyol Polymers 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000002904 solvent Substances 0.000 title abstract description 19
- 230000002194 synthesizing effect Effects 0.000 title 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000002253 acid Substances 0.000 claims abstract description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 24
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 235000011037 adipic acid Nutrition 0.000 claims description 12
- 239000003963 antioxidant agent Substances 0.000 claims description 12
- 230000003078 antioxidant effect Effects 0.000 claims description 12
- 235000006708 antioxidants Nutrition 0.000 claims description 12
- 239000012752 auxiliary agent Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000001384 succinic acid Substances 0.000 claims description 11
- 239000001361 adipic acid Substances 0.000 claims description 9
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 9
- 150000003384 small molecules Chemical class 0.000 claims description 8
- 239000012296 anti-solvent Substances 0.000 claims description 6
- 238000007664 blowing Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 238000001308 synthesis method Methods 0.000 claims description 4
- 238000011017 operating method Methods 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 229940051250 hexylene glycol Drugs 0.000 claims description 2
- 238000004260 weight control Methods 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims 8
- 229920003225 polyurethane elastomer Polymers 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 5
- 150000001298 alcohols Chemical class 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 150000007513 acids Chemical class 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 2
- 235000011044 succinic acid Nutrition 0.000 abstract 1
- 150000003444 succinic acids Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000012952 Resampling Methods 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001279 adipic acids Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical group CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Abstract
The invention belongs to a preparation method of a high molecular material, and particularly relates to a solvent resistance polyester polyol preparation method. The preparation method comprises the following steps of: adding micromolecule acids, micromolecule alcohols and other raw materials in weight ratio to a reaction kettle for heating, feeding nitrogen for protection, adopting the operation process of a step-by-step heating method, when each index reaches the standard, reducing the temperature and emptying, thus obtaining the polyester polyol. Succinic acids are taken as the main acids of the micromolecule acids, and diethylene glycols are taken as the main alcohols of the micromolecule alcohols. The polyester polyol synthesized by the method is clear and transparent and is liquid at normal temperature. A polyurethane elastomer obtained by taking the polyester polyol as the raw material through synthesis has excellent solvent resistance.
Description
Technical field
The invention belongs to a kind of preparation method of macromolecular material, particularly a kind of preparation method of the polyester polyol of anti-the solvent.
Background technology
Urethane is the high molecular synthetic material of a kind of performance between rubber and plastics, is characterized in that the hardness setting range is wide, and the elasticity of existing rubber has the hardness of plastics again, and polyurethane elastomer has good mechanical property, wear resisting property and rebound performance.But, in some special dimension, except having the wear-resisting of itself, outside the resilience, also to have splendid solvent resistance to urethane.
In the composite structure of polyurethane elastomer, the main material of main anti-solvent action is exactly polyester polyol, so, elastomeric anti-solvent quality height, and vital relation is arranged between the polyester polyol, carry out the solvent resistant polyurethane elastomerics, studying the polyester polyol of anti-the solvent is a requisite problem.
Usually the polyester polyol of anti-solvent of usefulness all is synthetic with hexanodioic acid and small molecular alcohol, because of the adipic acid carbochain longer, synthetic polyurethane elastomer urethane manthanoate content is lower, therefore influence solvent resistance, to such an extent as to synthetic polyurethane elastomer has been put in acetone, cyclohexanone, bubble is after 48 hours in the toluene equal solvent, its weight increase is used owing to swelling too much makes performance reduce influence greater than 100%.Therefore need provide a kind of solvent-proof polyester polyol, make its synthetic polyurethane product solvent resistance good.
Prior art discloses a kind of polyvalent alcohol of anti-the solvent and has prepared method for preparing polyurethane elastic body, synthesize by different ratios with small molecular alcohols such as Succinic Acid and ethylene glycol and Diethylene Glycols, though the goods solvent resistance of this prescription output is good, but work in-process is because the crystallinity of the polyester polyol of anti-the solvent is stronger, need exhaust a large amount of water when producing polyurethane elastomer,, gas, simultaneously, the performed polymer viscosity that is synthesized can double, and is subjected to great restriction so that process the goods of some softs.
Summary of the invention
The object of the present invention is to provide a kind of anti-solvent synthesis method of polyester polyol.
According to synthesis method of polyester polyol of the present invention, with small molecules acid and small molecular alcohol with acid alcohol by weight, join in the reactor and heat; and logical nitrogen protection; adopt the progressively operating procedure of temperature-raising method, the cooling blowing namely gets described polyester polyol after every index is all up to standard.
According to the present invention, described small molecules acid is main acid with the Succinic Acid, contains or do not contain adipic acid.
According to the present invention, described small molecular alcohol is main alcohol with the Diethylene Glycol, contains or does not contain 1, the 6-hexylene glycol.
Preferably, the weight ratio of described small molecules acid and small molecular alcohol and other raw materials is: Succinic Acid 43-45 part, adipic acid 0-5 part, Diethylene Glycol 51-45 part, 1,6-hexylene glycol 0-5 part, anti-oxidant auxiliary agent 0.2-1 part, catalyzer 0.03-0.08 part.
Further preferred, the weight ratio of described small molecules acid and small molecular alcohol and other raw materials is: Succinic Acid 43-45 part, adipic acid 3-5 part, Diethylene Glycol 51-45 part, 1,6-hexylene glycol 3-5 part, anti-oxidant auxiliary agent 0.2-1 part, catalyzer 0.03-0.08 part.
According to one of embodiment of the present invention, the number-average molecular weight of described Succinic Acid is 118, and outward appearance is white crystal, and content is greater than 99%.
Described adipic acid is that conventional adipic acid gets final product.
The preferred comparatively alcohol of high-quality of described Diethylene Glycol and 1,6-hexylene glycol.
Test shows, adopts Diethylene Glycol and 1,6-hexylene glycol to come the synthetic polyester polyol of component design, can effectively reduce the crystallinity of polyester polyol, and synthetic performed polymer will heat the difficult problem that could fuse in a large number in the downstream to have improved product greatly.
According to one of embodiment of the present invention, described polyester polyol molecular weight control is at 1500-1800, and namely hydroxyl value is controlled to be 75-62(mgKOH/g).
Preferably, the every qualified index of described polyester polyol is: acid number≤0.8(mgKOH/g), hydroxyl value is 75-62(mgKOH/g), water content is: below 0.05%.
According to another embodiment of the present invention, described anti-oxidant auxiliary agent is 1010.
Test shows, adds a small amount of anti-oxidant auxiliary agent in the prescription, does not influence in add-on under the prerequisite of polyester polyol quality, and the situation that can solve the easy xanthochromia of polyester in the building-up process produces, and improves the transparency of downstream product.
Described catalyzer is that the used catalyzer of normal polyester polyvalent alcohol gets final product.
According to an embodiment more of the present invention, described progressively temperature-raising method is: begin water outlet when temperature is raised to the 135-145 degree, the temperature of control reflux tower is the 101-102 degree, then the still temperature slowly is raised to the 155-165 degree, constant temperature 2-3 hour, the mode progressively to heat up afterwards, at 3-4 hour temperature is raised to the 220-230 degree, when water outlet finishes, be incubated 0.8-1.2 hour, beginning progressively vacuumizes.
Adopt the progressively operating procedure of temperature-raising method, the polyester polyol molecular distribution that is synthesized is more even, and the functionality of product has the goods that utilize the downstream to be synthesized to have more solvent resistance very near set(ting)value.
Test shows, be main raw material with Succinic Acid and Diethylene Glycol, add a small amount of anti-oxidant auxiliary agent, the polyester polyol clear that is synthesized, shape at normal temperatures is in a liquid state, the performed polymer viscosity that the performed polymer viscosity ratio conventional polyester that the downstream is synthesized is synthesized is high slightly, but can reach client's processing request fully.
Test shows, adopts the method for the invention, and the synthetic polyester polyol that obtains has splendid solvent resistance.
Embodiment
Describe embodiments of the present invention below in detail, described embodiment is exemplary, only is used for explaining the present invention, and can not be interpreted as limitation of the present invention.
Embodiment 1:
By weight with 43 parts of Succinic Acid; 5 parts of adipic acids; 45 parts of Diethylene Glycols; 5 parts of 1,6-hexylene glycols, 0.2 part of anti-oxidant auxiliary agent; 0.03 part of catalyzer; join in the reactor and heat, and logical nitrogen protection, when temperature is raised to 135 degree beginning water outlets; the temperature of control reflux tower is 101 degree; then the still temperature slowly is raised to 155 degree, constant temperature 2-3 hour, the mode progressively to heat up afterwards; at 3-4 hour temperature is raised to 230 degree; when water outlet finishes, be incubated 1 hour, beginning progressively vacuumizes; beginning sampling detecting acid number and hydroxyl value after 3 hours; when acid number＜1.0(mgKOH/g), hydroxyl value is to 75(mgKOH/g) when (being that molecular weight is 1500), stop to vacuumize; begin cooling; when temperature reaches the mensuration of resampling below 100 degree, begin blowing after every index is all up to standard, namely get polyester polyol.
Embodiment 2:
By weight with 45 parts of Succinic Acid; 51 parts of Diethylene Glycols; 1 part of anti-oxidant auxiliary agent, 0.08 part of catalyzer joins in the reactor and heats; and logical nitrogen protection; when temperature is raised to 140 degree beginning water outlets, the temperature of control reflux tower is 102 degree, then the still temperature slowly is raised to 165 degree; constant temperature 2-3 hour; mode progressively to heat up was raised to 220 degree at 3-4 hour with temperature, when water outlet finishes afterwards; be incubated 0.8 hour; beginning progressively vacuumizes, and beginning sampling detecting acid number and hydroxyl value after 3 hours is when acid number≤0.8(mgKOH/g); hydroxyl value is to 68(mgKOH/g) when (being that molecular weight is 1650); stop to vacuumize, begin cooling, when temperature reaches the mensuration of resampling below 100 degree; begin blowing after every index is all up to standard, namely get polyester polyol.
Embodiment 3:
By weight with 44 parts of Succinic Acid; 3 parts of adipic acids; 48 parts of Diethylene Glycols; 3 parts of 1,6-hexylene glycols, 0.6 part of anti-oxidant auxiliary agent; 0.05 part of catalyzer; join in the reactor and heat, and logical nitrogen protection, when temperature is raised to 145 degree beginning water outlets; the temperature of control reflux tower is 102 degree; then the still temperature slowly is raised to 160 degree, constant temperature 2-3 hour, the mode progressively to heat up afterwards; at 3-4 hour temperature is raised to 230 degree; when water outlet finishes, be incubated 1.2 hours, beginning progressively vacuumizes; beginning sampling detecting acid number and hydroxyl value after 3 hours; when acid number＜0.8(mgKOH/g), hydroxyl value is to 62(mgKOH/g) when (being that molecular weight is 1800), stop to vacuumize; begin cooling; when temperature reaches the mensuration of resampling below 100 degree, begin blowing after every index is all up to standard, namely get polyester polyol.
Embodiment 4:
By weight with 45 parts of Succinic Acid; 2 parts of adipic acids; 50 parts of Diethylene Glycols; 2 parts of 1,6-hexylene glycols, 0.8 part of anti-oxidant auxiliary agent; 0.06 part of catalyzer; join in the reactor and heat, and logical nitrogen protection, when temperature is raised to 140 degree beginning water outlets; the temperature of control reflux tower is 102 degree; then the still temperature slowly is raised to 160 degree, constant temperature 2-3 hour, the mode progressively to heat up afterwards; at 3-4 hour temperature is raised to 225 degree; when water outlet finishes, be incubated 1 hour, beginning progressively vacuumizes; beginning sampling detecting acid number and hydroxyl value after 3 hours; when acid number≤0.8(mgKOH/g), hydroxyl value is to 62(mgKOH/g) when (being that molecular weight is 1800), stop to vacuumize; begin cooling; when temperature reaches the mensuration of resampling below 100 degree, begin blowing after every index is all up to standard, namely get polyester polyol.
Embodiment 5
For better assessment is that raw material further synthesizes the solvent resistance of the polyurethane elastomer that obtains and the solvent resistance that the conventional polyester polyvalent alcohol synthesizes polyurethane elastomer with the synthetic polyester polyol that obtains of the inventive method, the spy proves from following example:
Adopt the synthesis mode of pre-polymerization method: by weight percentage, with polyester polyol 80-87%, vulcabond 13-20%, through 75-80 degree isothermal reaction 2 hours, obtain the performed polymer that performed polymer content is 3-5%, make the solvent resistant polyurethane elastomerics at 80 degree with the solidifying agent reaction then, described solidifying agent is TriMethylolPropane(TMP) or does not block, described vulcabond refers to tolylene diisocyanate (TDI), diphenylmethanediisocyanate (MDI) and isomer thereof, preferred T-100, the weight proportion of performed polymer and solidifying agent is 100:7-15.
In the above formulation examples, polyester polyol is made comparisons with polyester polyol and the conventional polyester polyvalent alcohol of embodiments of the invention 1-4 gained respectively.
Polyurethane elastomer product properties such as following table:
Draw by above form: the synthetic polyester polyol that obtains of the inventive method has splendid solvent resistance really.
Claims (9)
1. anti-solvent synthesis method of polyester polyol; it is characterized in that; with small molecules acid and small molecular alcohol and other raw materials by weight; join in the reactor and heat; and logical nitrogen protection; adopt the progressively operating procedure of temperature-raising method, the cooling blowing namely gets described polyester polyol after every index is all up to standard.
2. according to the described synthetic method of claim 1, it is characterized in that described small molecules acid is main acid with the Succinic Acid, adds or do not add adipic acid.
3. according to the described synthetic method of claim 1, it is characterized in that described small molecular alcohol is main alcohol with the Diethylene Glycol, add or do not add 1, the 6-hexylene glycol.
4. according to each described synthetic method of claim 1-3, it is characterized in that, the weight ratio of described small molecules acid and small molecular alcohol and other raw materials is: Succinic Acid 43-45 part, adipic acid 0-5 part, Diethylene Glycol 51-45 part, 1,6-hexylene glycol 0-5 part, anti-oxidant auxiliary agent 0.2-1 part, catalyzer 0.03-0.08 part.
5. according to the described synthetic method of claim 4, it is characterized in that, the weight ratio of described small molecules acid and small molecular alcohol and other raw materials is: Succinic Acid 43-45 part, adipic acid 3-5 part, Diethylene Glycol 51-45 part, 1,6-hexylene glycol 3-5 part, anti-oxidant auxiliary agent 0.2-1 part, catalyzer 0.03-0.08 part.
6. according to the described synthetic method of claim 4, it is characterized in that described polyester polyol molecular weight control is at 1500-1800.
7. according to the described synthetic method of claim 4, it is characterized in that the every qualified index of described polyester polyol is: acid number≤0.8mgKOH/g, hydroxyl value is 75-62mgKOH/g, water content is: below 0.05%.
8. according to the described synthetic method of claim 6, it is characterized in that described anti-oxidant auxiliary agent is 1010.
9. according to the described synthetic method of claim 1, it is characterized in that, described progressively temperature-raising method is: begin water outlet when temperature is raised to the 135-145 degree, the temperature of control reflux tower is the 101-102 degree, then the still temperature slowly is raised to the 155-165 degree, constant temperature 2-3 hour, mode progressively to heat up was raised to the 220-230 degree at 3-4 hour with temperature, when water outlet finishes afterwards, be incubated 0.8-1.2 hour, beginning progressively vacuumizes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013101376775A CN103183816A (en) | 2013-04-20 | 2013-04-20 | Solvent resistance polyester polyol synthesizing method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013101376775A CN103183816A (en) | 2013-04-20 | 2013-04-20 | Solvent resistance polyester polyol synthesizing method |
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| CN103183816A true CN103183816A (en) | 2013-07-03 |
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| CN2013101376775A Pending CN103183816A (en) | 2013-04-20 | 2013-04-20 | Solvent resistance polyester polyol synthesizing method |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103642010A (en) * | 2013-10-23 | 2014-03-19 | 江苏盈天化学有限公司 | Method for preparing adipic acid polyester polyol by utilizing recycled alcohol |
| CN104387568A (en) * | 2014-12-16 | 2015-03-04 | 山东一诺威聚氨酯股份有限公司 | Synthesis method of biological-based polyester polyol |
| CN107254161A (en) * | 2017-06-22 | 2017-10-17 | 广东元星工业新材料有限公司 | Low temperature-resistanpolyurethane polyurethane elastomer and preparation method thereof |
| CN108912300A (en) * | 2018-08-03 | 2018-11-30 | 山东诺威聚氨酯股份有限公司 | Solvent-proof polyurethane elastomer and preparation method thereof |
| CN113549199A (en) * | 2021-07-23 | 2021-10-26 | 华大化学集团有限公司 | Bio-based solvent-resistant polyester polyol, polyurethane resin and preparation process thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101130597A (en) * | 2007-09-29 | 2008-02-27 | 山东东大一诺威聚氨酯有限公司 | Synthesis method of solvent resistant solvent type urethane elastomer |
-
2013
- 2013-04-20 CN CN2013101376775A patent/CN103183816A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101130597A (en) * | 2007-09-29 | 2008-02-27 | 山东东大一诺威聚氨酯有限公司 | Synthesis method of solvent resistant solvent type urethane elastomer |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103642010A (en) * | 2013-10-23 | 2014-03-19 | 江苏盈天化学有限公司 | Method for preparing adipic acid polyester polyol by utilizing recycled alcohol |
| CN103642010B (en) * | 2013-10-23 | 2015-09-30 | 江苏盈天化学有限公司 | A kind of method utilizing recovery alcohol to prepare hexanodioic acid kind polyester polyvalent alcohol |
| CN104387568A (en) * | 2014-12-16 | 2015-03-04 | 山东一诺威聚氨酯股份有限公司 | Synthesis method of biological-based polyester polyol |
| CN107254161A (en) * | 2017-06-22 | 2017-10-17 | 广东元星工业新材料有限公司 | Low temperature-resistanpolyurethane polyurethane elastomer and preparation method thereof |
| CN108912300A (en) * | 2018-08-03 | 2018-11-30 | 山东诺威聚氨酯股份有限公司 | Solvent-proof polyurethane elastomer and preparation method thereof |
| WO2020024539A1 (en) * | 2018-08-03 | 2020-02-06 | 山东一诺威聚氨酯股份有限公司 | Solvent resistent polyurethane elastomer and preparation method thereof |
| CN113549199A (en) * | 2021-07-23 | 2021-10-26 | 华大化学集团有限公司 | Bio-based solvent-resistant polyester polyol, polyurethane resin and preparation process thereof |
| CN113549199B (en) * | 2021-07-23 | 2024-01-30 | 华大化学集团有限公司 | Bio-based solvent-resistant polyester polyol, polyurethane resin and preparation process thereof |
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Application publication date: 20130703 |