CN103113560A - Preparation method of dimer acid type polyester polyol - Google Patents
Preparation method of dimer acid type polyester polyol Download PDFInfo
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- CN103113560A CN103113560A CN2013100546800A CN201310054680A CN103113560A CN 103113560 A CN103113560 A CN 103113560A CN 2013100546800 A CN2013100546800 A CN 2013100546800A CN 201310054680 A CN201310054680 A CN 201310054680A CN 103113560 A CN103113560 A CN 103113560A
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Abstract
The invention provides a preparation method of dimer acid type polyester polyol, belonging to the technical field of esterification polymerization in oil chemistry. The method comprises the following steps of: carrying out esterification polymerization reaction in the presence of an organic catalyst under the protection of nitrogen based on long-chain dimer acid of binary acid and dihydric alcohol as main raw materials; and further carrying out vacuum dehydration and demonomerization to obtain dimer acid type polyester polyols of different specifications, wherein the acid value is lower than 1mgKOH/g, and the number-average molecular weight is lower than 1,300-3,000. The preparation method provided by the invention has the characteristics of easy technical operation, high product yield, stable product quality and low operation cost.
Description
Technical field
The present invention relates to a kind of preparation method of dimer acid type polyester polyol.Belong to oil chemical industry and fully utilize the field.
Background technology
The product that normal polyester polyvalent alcohol product is made as poly-hexanodioic acid one butanediol ester, poly-hexanodioic acid monoethylene glycol ester has affected the application in low temperature resistant elastomerics, antifouling paste, marine coating etc. have the particular requirement polyurethane industrial at aspect Shortcomings such as resistant to hydrolysis, anti-oxidant, uvioresistant decomposition.
Summary of the invention
The objective of the invention is to change polyester polyol structure, improve the over-all properties of polyester polyol.For this reason, the invention provides a kind of preparation method of dimer acid type polyester polyol.
The preparation method of dimer acid type polyester polyol provided by the invention, carry out polyreaction for utilizing diprotic acid unit and glycol unit, obtain containing the dimer acid type polyester polyol of diprotic acid copolymerization units and dibasic alcohol copolymerization units, (1) diprotic acid unit comprises:
(a) 10-100 molar part dimeracid, and
(b) 0-90 molar part diprotic acid,
(2) glycol unit is the 105-300 molar part.
Preferably,
(1) the diprotic acid unit comprises:
(a) 25-100 molar part dimeracid, and
(b) 0-75 molar part diprotic acid,
(2) glycol unit is the 115-200 molar part.
Preferably, described dimeracid refers to one or more in appropriate youngster's oil dimeracid, cotton oil dimeracid, soya-bean oil dimeracid, Fructus Maydis oil dimeracid, sunflower seed oil dimeracid and rapeseed oil dimeracid.
Described dimeracid can be general goods dimeracid, high-purity dimeric acid or hydrogenated dimer acids.Be preferably high-purity dimeric acid or hydrogenated dimer acids.
Preferably, described diprotic acid is aliphatic dibasic acid and/or aromatic acid, described aliphatic dibasic acid is one or more in dimeracid, succinic acid, pentanedioic acid, hexanodioic acid, suberic acid, nonane diacid, sebacic acid, dodecanedioic acid and 14 carbon diacid, and described aromatic acid is one or more in phthalic acid, m-phthalic acid and terephthalic acid.
Preferably be respectively terephthalic acid and hexanodioic acid.
Preferably, described dibasic alcohol is neopentyl glycol, ethylene glycol, propylene glycol, ethyl butyl propanediol, 2-methyl isophthalic acid, ammediol, BDO, 1,5-pentanediol, 3-methyl pentanediol, 1, one or more in 6-hexylene glycol, Diethylene Glycol and two polyalcohols.
Be preferably neopentyl glycol or Diethylene Glycol.
Preferably, the total mole number of described diprotic acid copolymerization units is 1:1.15-2 with the ratio of the total mole number of dibasic alcohol copolymerization units.
Preferably, described polyreaction is used organic catalyst, and described organic catalyst is one or more in tin protochloride, tetrabutyl titanate, titanium isopropylate and dibutyl tin laurate, and the organic catalyst consumption is 15-500PPm.
Be preferably 50-350PPm, more preferably 100-150PPm.
preferably, the method comprises the following steps, add reaction mass, open and stir and heat temperature raising, nitrogen protection, when temperature of charge is raised to 135-145 ℃, the beginning water outlet, control heat-up rate this moment, temperature rise rate 20-25 ℃/h, the water of generation is steamed gradually, when temperature of charge is raised to 160～170 ℃, insulation reaction 1.5-2.5h, continue slowly to be warming up to 195-205 ℃ of reaction, then, close nitrogen, open vacuum pump, decompression vacuum pumping, control vacuum tightness 680-760mmHg, slowly be warming up to 220-230 ℃, keep reaction 2.5-3.5h left and right, the sampling and measuring acid value is less than below 1mgKOH/g, reaction finishes, slowly cool to 140-160 ℃, the vacuum breaker discharging.
Preferably, described vacuum degree control is preferably 730---740mmHg at 700-750mmHg.Described acid value is preferably 0.4---0.9mgKOH/g, is preferably 0.5---0.7mgKOH/g.
The invention still further relates to the application of the dimer acid type polyester polyol of described method preparation, this is applied as described polyvalent alcohol as the raw materials of coating, tackiness agent, elastomerics or porous plastics.
Dimeracid is the polymerisate of natural fats and oils unsaturated fatty acids, has that toxicity is low, wide material sources and characteristics such as renewable.Because dimeracid contains two carboxyls and two larger nonpolar alkyl, the long carbochain of the branched structure of its height and 36 carbon atom formations makes it have amorphism, the flexibility of height and superpower hydrophobic nature.Can give their special character with its high-polymer molecular structure that induces one, thereby become the desirable feedstock of synthetic macromolecule.The dimer acid type polyester polyol has extraordinary hydrolytic resistance, good anti-extension strength, snappiness, good initial stage bonding strength, good resistance to thermooxidation, color developing, particularly have extraordinary bonding strength and sticking power to the ground of low surface tension preferably.Dimer acid polyester polyhydric alcohols and dimer acid modified polyester polyol have extraordinary performance, can be widely used in coating, tackiness agent, leather finish, fabric coating, timber, elastomerics, a plurality of industries such as porous plastics.
The present invention have technological operation easily, high, the constant product quality of product yield, characteristics that process cost is low.
Embodiment
example one, with thermometer, mechanical stirrer, add high-purity dimeric acid 496g in the four-hole boiling flask of condenser and nitrogen access tube, hexanodioic acid 496g, neopentyl glycol 567g, add catalyzer dibutyl tin laurate 0.2g, open and stir and heat temperature raising, slowly heat up, stirring velocity is controlled 300n/min, system's nitrogen protection pressure-fired is at 1050Pa, when temperature of charge is raised to 140 ℃, the beginning water outlet, control heat-up rate this moment, temperature rise rate 20---25 ℃/h, the water of generation is steamed gradually, when temperature of charge is raised to 160～170 ℃, insulation reaction 2h left and right, continue slowly to be warming up to 200 ℃ of reactions, then, close nitrogen, open vacuum pump, decompression vacuum pumping, control vacuum tightness 740mmHg, slowly be warming up to 225 ℃, keep reaction 3h left and right, the sampling and measuring acid value is less than below 1mgKOH/g, reaction finishes, slowly cool to 150 ℃, the vacuum breaker discharging.Obtain acid value 0.73mgKOH/g, hydroxyl valency 57mgKOH/g, faint yellow transparent, the dimer acid type polyester polyol of number-average molecular weight 2000.
example two, with thermometer, mechanical stirrer, add high-purity dimeric acid 496g in the four-hole boiling flask of condenser and nitrogen access tube, hexanodioic acid 496g, Diethylene Glycol 578g, add catalyzer metatitanic acid four butyl ester 0.1g, open and stir and heat temperature raising, slowly heat up, stirring velocity is controlled 300n/min, system's nitrogen protection pressure-fired is at 1050Pa, when temperature of charge is raised to 140 ℃, the beginning water outlet, control heat-up rate this moment, temperature rise rate 20---25 ℃/h, the water of generation is steamed gradually, when temperature of charge is raised to 160～170 ℃, insulation reaction 2h left and right, continue slowly to be warming up to 200 ℃ of reactions, then, close nitrogen, open vacuum pump, decompression vacuum pumping, control vacuum tightness 740mmHg, slowly be warming up to 225 ℃, keep reaction 3h left and right, the sampling and measuring acid value is less than below 1mgKOH/g, reaction finishes, slowly cool to 150 ℃, the vacuum breaker discharging.Obtain acid value 0.68mgKOH/g, hydroxyl valency 57mgKOH/g, faint yellow transparent, the dimer acid type polyester polyol of number-average molecular weight 2000.
example three, with thermometer, mechanical stirrer, add high-purity dimeric acid 560g in the four-hole boiling flask of condenser and nitrogen access tube, two polyalcohols 1070g, add catalyzer metatitanic acid four butyl ester 0.1g, open and stir and heat temperature raising, slowly heat up, stirring velocity is controlled 300n/min, system's nitrogen protection pressure-fired is at 1050Pa, when temperature of charge is raised to 140 ℃, the beginning water outlet, control heat-up rate this moment, temperature rise rate 20---25 ℃/h, the water of generation is steamed gradually, when temperature of charge is raised to 160～170 ℃, insulation reaction 2h left and right, continue slowly to be warming up to 200 ℃ of reactions, then, close nitrogen, open vacuum pump, decompression vacuum pumping, control vacuum tightness 740mmHg, slowly be warming up to 225 ℃, keep reaction 3h left and right, the sampling and measuring acid value is less than below 1mgKOH/g, reaction finishes, slowly cool to 150 ℃, the vacuum breaker discharging.Obtain acid value 0.98mgKOH/g, hydroxyl valency 71mgKOH/g, faint yellow transparent, the dimer acid type polyester polyol of number-average molecular weight 1700.
example four, with thermometer, mechanical stirrer, add high-purity dimeric acid 840g in the four-hole boiling flask of condenser and nitrogen access tube, neopentyl glycol 208g, add catalyzer dibutyl tin laurate 0.2g, open and stir and heat temperature raising, slowly heat up, stirring velocity is controlled 300n/min, system's nitrogen protection pressure-fired is at 1050Pa, when temperature of charge is raised to 140 ℃, the beginning water outlet, control heat-up rate this moment, temperature rise rate 20---25 ℃/h, the water of generation is steamed gradually, when temperature of charge is raised to 160～170 ℃, insulation reaction 2h left and right, continue slowly to be warming up to 200 ℃ of reactions, then, close nitrogen, open vacuum pump, decompression vacuum pumping, control vacuum tightness 740mmHg, slowly be warming up to 225 ℃, keep reaction 3h left and right, the sampling and measuring acid value is less than below 1mgKOH/g, reaction finishes, slowly cool to 150 ℃, the vacuum breaker discharging.Obtain acid value 0.95mgKOH/g, hydroxyl valency 56mgKOH/g, faint yellow transparent, the dimer acid type polyester polyol of number-average molecular weight 2000.
example five, with thermometer, mechanical stirrer, add dimeracid 1120g in the four-hole boiling flask of condenser and nitrogen access tube, Diethylene Glycol 318g, add catalyzer metatitanic acid four butyl ester 0.1g, open and stir and heat temperature raising, slowly heat up, stirring velocity is controlled 300n/min, system's nitrogen protection pressure-fired is at 1050Pa, when temperature of charge is raised to 140 ℃, the beginning water outlet, control heat-up rate this moment, temperature rise rate 20---25 ℃/h, the water of generation is steamed gradually, when temperature of charge is raised to 160～170 ℃, insulation reaction 2h left and right, continue slowly to be warming up to 200 ℃ of reactions, then, close nitrogen, open vacuum pump, decompression vacuum pumping, control vacuum tightness 740mmHg, slowly be warming up to 225 ℃, keep reaction 3h left and right, the sampling and measuring acid value is less than below 1mgKOH/g, reaction finishes, slowly cool to 150 ℃, the vacuum breaker discharging.Obtain acid value 0.85mgKOH/g, hydroxyl valency 85mgKOH/g, yellow transparent, the dimer acid type polyester polyol of number-average molecular weight 1300.
example six, with thermometer, mechanical stirrer, add high-purity dimeric acid 1120g in the four-hole boiling flask of condenser and nitrogen access tube, neopentyl glycol 365g, add catalyzer dibutyl tin laurate 0.2g, open and stir and heat temperature raising, slowly heat up, stirring velocity is controlled 300n/min, system's nitrogen protection pressure-fired is at 1050Pa, when temperature of charge is raised to 140 ℃, the beginning water outlet, control heat-up rate this moment, temperature rise rate 20---25 ℃/h, the water of generation is steamed gradually, when temperature of charge is raised to 160～170 ℃, insulation reaction 2h left and right, continue slowly to be warming up to 200 ℃ of reactions, then, close nitrogen, open vacuum pump, decompression vacuum pumping, control vacuum tightness 740mmHg, slowly be warming up to 225 ℃, keep reaction 3h left and right, the sampling and measuring acid value is less than below 1mgKOH/g, reaction finishes, slowly cool to 150 ℃, the vacuum breaker discharging.Obtain acid value 0.92mgKOH/g, hydroxyl valency 38mgKOH/g, faint yellow transparent, the dimer acid type polyester polyol of number-average molecular weight 3000.
Claims (10)
1. the preparation method of a dimer acid type polyester polyol, the method obtains containing the dimer acid type polyester polyol of diprotic acid copolymerization units and dibasic alcohol copolymerization units for utilizing diprotic acid unit and glycol unit to carry out polyreaction, it is characterized in that,
(1) the diprotic acid unit comprises:
(a) 10-100 molar part dimeracid, and
(b) 0-90 molar part diprotic acid,
(2) glycol unit is the 105-300 molar part.
2. dimer acid type polyester polyol as claimed in claim 1, is characterized in that
(1) the diprotic acid unit comprises:
(a) 25-100 molar part dimeracid, and
(b) 0-75 molar part diprotic acid,
(2) glycol unit is the 115-200 molar part.
3. preparation method as claimed in claim 1, is characterized in that, described dimeracid refers to one or more in appropriate youngster's oil dimeracid, cotton oil dimeracid, soya-bean oil dimeracid, Fructus Maydis oil dimeracid, sunflower seed oil dimeracid and rapeseed oil dimeracid.
4. preparation method as claimed in claim 1, it is characterized in that, described diprotic acid is aliphatic dibasic acid and/or aromatic acid, described aliphatic dibasic acid is one or more in dimeracid, succinic acid, pentanedioic acid, hexanodioic acid, suberic acid, nonane diacid, sebacic acid, dodecanedioic acid and 14 carbon diacid, and described aromatic acid is one or more in phthalic acid, m-phthalic acid and terephthalic acid.
5. preparation method as claimed in claim 1, it is characterized in that, described dibasic alcohol is neopentyl glycol, ethylene glycol, propylene glycol, ethyl butyl propanediol, 2-methyl isophthalic acid, ammediol, 1,4-butyleneglycol, 1,5-pentanediol, 3-methyl pentanediol, 1, one or more in 6-hexylene glycol, Diethylene Glycol and two polyalcohols.
6. preparation method as claimed in claim 1, is characterized in that, the total mole number of described diprotic acid copolymerization units is 1:1.15-2 with the ratio of the total mole number of dibasic alcohol copolymerization units.
7. preparation method as claimed in claim 1, it is characterized in that, described polyreaction is used organic catalyst, and described organic catalyst is one or more in tin protochloride, tetrabutyl titanate, titanium isopropylate and dibutyl tin laurate, and the organic catalyst consumption is 15-500PPm.
8. preparation method as claimed in claim 1, it is characterized in that, the method comprises the following steps, add reaction mass, open and stir and heat temperature raising, nitrogen protection, when temperature of charge is raised to 135-145 ℃, the beginning water outlet, control heat-up rate this moment, temperature rise rate 20-25 ℃/h, the water of generation is steamed gradually, when temperature of charge is raised to 160～170 ℃, insulation reaction 1.5-2.5h, continue slowly to be warming up to 195-205 ℃ of reaction, then, close nitrogen, open vacuum pump, decompression vacuum pumping, control vacuum tightness 680-760mmHg, slowly be warming up to 220-230 ℃, keep reaction 2.5-3.5h left and right, the sampling and measuring acid value is less than below 1mgKOH/g, reaction finishes, slowly cool to 140-160 ℃, the vacuum breaker discharging.
9. preparation method as claimed in claim 1, is characterized in that, described vacuum degree control is at 700---750mmHg, and described acid value is 0.4---0.9mgKOH/g.
10. the application of the dimer acid type polyester polyol of the described method preparation of claim 1 to 9 any one, this is applied as described polyvalent alcohol as the raw materials of coating, tackiness agent, elastomerics or porous plastics.
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| CN105199085A (en) * | 2015-09-16 | 2015-12-30 | 常州大学 | Dimer acid modified poly (butylene succinate) copolyester and preparation method thereof |
| CN106459341A (en) * | 2014-05-05 | 2017-02-22 | 树脂酸盐材料集团有限公司 | Polyester polyols from thermoplastic polyesters and dimer fatty acids |
| CN107266655A (en) * | 2017-08-02 | 2017-10-20 | 浙江枧洋高分子科技有限公司 | A kind of phosphorus nitrogen synergistic intumescent self-extinguishing waterborn polyurethane and preparation method thereof |
| CN107922598A (en) * | 2015-09-04 | 2018-04-17 | Dic株式会社 | Polyester resin, the manufacture method of polyester resin, resin combination, the cloth and silk of resin and resin cloth and silk manufacture method |
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| US10611879B2 (en) | 2014-05-05 | 2020-04-07 | Resinate Materials Group, Inc. | Polyester polyols from thermoplastic polyesters and dimer fatty acids |
| CN106459341A (en) * | 2014-05-05 | 2017-02-22 | 树脂酸盐材料集团有限公司 | Polyester polyols from thermoplastic polyesters and dimer fatty acids |
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| US10465335B2 (en) | 2015-09-04 | 2019-11-05 | Dic Corporation | Polyester resin, method for producing polyester resin, resin composition, resin-clad fabric, and method for producing resin-clad fabric |
| CN105199085A (en) * | 2015-09-16 | 2015-12-30 | 常州大学 | Dimer acid modified poly (butylene succinate) copolyester and preparation method thereof |
| CN108203575A (en) * | 2016-12-20 | 2018-06-26 | 苏州宇熠新材料科技有限公司 | A kind of two-component nylon and the film adhered glue of transparent TPU and preparation method |
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| CN107266655B (en) * | 2017-08-02 | 2020-01-17 | 浙江枧洋高分子科技有限公司 | Phosphorus-nitrogen synergistic intumescent self-flame-retardant waterborne polyurethane and preparation method thereof |
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| CN109439382A (en) * | 2018-11-09 | 2019-03-08 | 深圳春雨润滑科技有限公司 | A kind of polymerization ester oil and preparation method thereof |
| CN113039230A (en) * | 2018-11-21 | 2021-06-25 | 3M创新有限公司 | Polyester polyols and polyurethane polymers made therefrom |
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| US11845863B2 (en) | 2020-05-04 | 2023-12-19 | Carlisle Construction Materials, LLC | Polyurethane dispersions and their use to produce coatings and adhesives |
| CN112457476A (en) * | 2020-12-09 | 2021-03-09 | 福建汇得新材料有限公司 | Polyester polyol with good polyether intermiscibility and preparation method thereof |
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