CN109517160A - A kind of preparation method of secondary amine type polyetheramine - Google Patents
A kind of preparation method of secondary amine type polyetheramine Download PDFInfo
- Publication number
- CN109517160A CN109517160A CN201811438910.2A CN201811438910A CN109517160A CN 109517160 A CN109517160 A CN 109517160A CN 201811438910 A CN201811438910 A CN 201811438910A CN 109517160 A CN109517160 A CN 109517160A
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- China
- Prior art keywords
- polyetheramine
- secondary amine
- parts
- amine type
- reaction
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
Abstract
The present invention relates to a kind of preparation methods of secondary amine type polyetheramine, characterized by the following steps, proportion as described below is mass fraction: 100 parts of polyetheramine and 52~86 parts of n-butyl glycidyl ether are added in the reaction kettle equipped with thermometer, condensing reflux and blender, and the acetic acid of 3~5 parts of addition, it is warming up to 65~75 DEG C, after 4~6h of insulation reaction, cooling discharge obtains secondary amine type polyetheramine.This kind of method can reduce the reaction rate with isocyanates, can improve conversion ratio and yield convenient for reaction process control.
Description
Technical field
The present invention relates to fine chemistry industry synthesis field more particularly to a kind of preparation methods of secondary amine type polyetheramine.
Background technique
Polyetheramine is that a kind of main chain is polyether structure, and terminal reactive group is the polymer of amido.Polyetheramine is helped in weaving
Agent field is commonly used to be used as the raw material for preparing hydrophilic silicone oil, and the activity of the amido in polyetheramine is stronger, is easy and epoxy group etc.
Group reacts.It begins one's study now with some scholars hydrophilic to prepare as the chain extender of synthesis of polyurethane using polyetheramine
The polyurethane of type, principle are to be reacted using the polyetheramine containing primary amine with isocyanates, but the activity of primary amine is high, at room temperature
It can be reacted with isocyanates, and reaction speed is fast, be easy to happen cross-linking reaction, generate urea, reaction is not easy to control；Conversion
Rate and yield be not high.
Summary of the invention
The technical problem to be solved by the present invention is to for the prior art status provide it is a kind of can reduce and isocyanates
Reaction rate, the preparation method of the secondary amine type polyetheramine of conversion ratio and yield can be improved convenient for reaction process control.
The technical scheme of the invention to solve the technical problem is: a kind of preparation method of secondary amine type polyetheramine,
Include the following steps, proportion as described below is mass fraction: 100 parts of polyetheramine and 52~86 parts of normal-butyl being shunk sweet
Oily ether is added in the reaction kettle equipped with thermometer, condensing reflux and blender, and 3~5 parts of acetic acid is added, it is warming up to 65~
75 DEG C, after 4~6h of insulation reaction, cooling discharge obtains secondary amine type polyetheramine,
Specific reaction equation is as follows:
Wherein x, y are integer, and 1≤x≤3,3≤y≤8.
Preferably, the number-average molecular weight of the polyetheramine is 300~500.
Compared with the prior art, the advantages of the present invention are as follows:
1, the present invention in by polyethex amine modification at secondary amine type polyetheramine, reduce the reactivity of polyetheramine, can be used as
The hydrophilic chain extender of polyurethane.Compared with polyetheramine, the reaction speed of secondary amine type polyetheramine and isocyanates is slow, in reaction process
It is not susceptible to cross-linking reaction, reacts more preferable control；To improve conversion ratio and yield.
2, present invention process is fairly simple, and reaction process is suitble to industrialized production convenient for control.
Specific embodiment
Below with reference to embodiment, specific embodiments of the present invention will be described in further detail.
The reaction equation of generation secondary amine type polyetheramine is in following embodiments
Wherein x, y are integer, and 1≤x≤3,3≤y≤8.
Embodiment 1
100 parts of polyetheramine and 52 parts of n-butyl glycidyl ether are added to equipped with thermometer, be condensed back and stirred
It mixes in the reaction kettle of device, and 3 parts of acetic acid is added, be warming up to 65 DEG C, after insulation reaction 6h, it is poly- to obtain secondary amine type for cooling discharge
Ether amines.The number-average molecular weight of polyetheramine described in the present embodiment can be preferably 300~500.
Embodiment 2
100 parts of polyetheramine and 62 parts of n-butyl glycidyl ether are added to equipped with thermometer, be condensed back and stirred
It mixes in the reaction kettle of device, and 3 parts of acetic acid is added, be warming up to 70 DEG C, after insulation reaction 6h, it is poly- to obtain secondary amine type for cooling discharge
Ether amines.The number-average molecular weight of polyetheramine described in the present embodiment can be preferably 300~500.
Embodiment 3
100 parts of polyetheramine and 76 parts of n-butyl glycidyl ether are added to equipped with thermometer, be condensed back and stirred
It mixes in the reaction kettle of device, and 4 parts of acetic acid is added, be warming up to 70 DEG C, after insulation reaction 5h, it is poly- to obtain secondary amine type for cooling discharge
Ether amines.The number-average molecular weight of polyetheramine described in the present embodiment can be preferably 300~500.
Embodiment 4
100 parts of polyetheramine and 86 parts of n-butyl glycidyl ether are added to equipped with thermometer, be condensed back and stirred
It mixes in the reaction kettle of device, and 5 parts of acetic acid is added, be warming up to 75 DEG C, after insulation reaction 4h, cooling discharge is obtained
Secondary amine type polyetheramine.The number-average molecular weight of polyetheramine described in the present embodiment can be preferably 300~500.
Testing performance index
Epoxy ring-opening rate: epoxide number in product is carried out with reference to GB/T1677-2008 " measurement of plasticizer epoxide number "
Test, from the conversion ratio of side reflection reaction process.
Secondary amine value yield: total amine value measurement: product is titrated using 0.5mol/L hydrochloric acid solution, by consuming hydrochloric acid
Volume can calculate total amine value of product；Secondary amine value measurement: by product with etc. quality salicylide be mixed 2h, use
0.5mol/L hydrochloric acid solution titrates product, and the volume by consuming hydrochloric acid can calculate the secondary amine value of product；Secondary amine
Yield=secondary amine value of value/total amine value × 100%.
Secondary amine type polyetheramine molecular weight: the molecular mass for obtaining product is surveyed using gas-liquid phase mass spectrometer
It is fixed.
Epoxy ring-opening rate, secondary amine value yield and molecular weight product test result such as 1 institute of table in reaction process of the present invention
Show:
Epoxy ring-opening rate, secondary amine value yield and molecular weight product test result in 1 reaction process of table
| Epoxy ring-opening rate/% | Secondary amine value yield/% | Secondary amine type polyetheramine molecular weight | |
| Embodiment 1 | 92.41 | 91.36 | 742 |
| Embodiment 2 | 92.88 | 92.19 | 691 |
| Embodiment 3 | 94.76 | 94.67 | 627 |
| Embodiment 4 | 93.55 | 92.58 | 562 |
Claims (2)
1. a kind of preparation method of secondary amine type polyetheramine, it is characterised in that include the following steps, proportion as described below is quality
Number: 100 parts of polyetheramine and 52~86 parts of n-butyl glycidyl ether are added to equipped with thermometer, be condensed back and stirred
It mixes in the reaction kettle of device, and 3~5 parts of acetic acid is added, be warming up to 65~75 DEG C, after 4~6h of insulation reaction, cooling discharge is obtained
To secondary amine type polyetheramine,
Specific reaction equation is as follows:
Wherein x, y are integer, and 1≤x≤3,3≤y≤8.
2. the preparation method of secondary amine type polyetheramine according to claim 1, it is characterised in that: the number of the polyetheramine is divided equally
Son amount is 300~500.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811438910.2A CN109517160A (en) | 2018-11-28 | 2018-11-28 | A kind of preparation method of secondary amine type polyetheramine |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811438910.2A CN109517160A (en) | 2018-11-28 | 2018-11-28 | A kind of preparation method of secondary amine type polyetheramine |
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| CN109517160A true CN109517160A (en) | 2019-03-26 |
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| CN201811438910.2A Pending CN109517160A (en) | 2018-11-28 | 2018-11-28 | A kind of preparation method of secondary amine type polyetheramine |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112375528A (en) * | 2020-11-11 | 2021-02-19 | 广州聚合新材料科技股份有限公司 | Reactive polyurethane hot melt adhesive, preparation method and application |
| CN113336953A (en) * | 2021-06-21 | 2021-09-03 | 宁波润禾高新材料科技股份有限公司 | Modified polyether amine, and preparation method and application thereof |
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| JPS6467378A (en) * | 1987-09-09 | 1989-03-14 | Mitsui Toatsu Chemicals | Desensitizing ink |
| CN104812794A (en) * | 2012-09-28 | 2015-07-29 | 陶氏环球技术有限责任公司 | Adduct compositions |
| CN106188502A (en) * | 2016-07-20 | 2016-12-07 | 江苏丰彩新型建材有限公司 | A kind of self-emulsifying type epoxy hardener, reinforcing varnish and preparation method thereof |
| CN107868241A (en) * | 2017-11-24 | 2018-04-03 | 威海翔泽新材料科技有限公司 | A kind of fatty alcohol block polyether class tar ammonia demulsifier and preparation method thereof |
| CN108285533A (en) * | 2017-01-09 | 2018-07-17 | 合记化学股份有限公司 | A kind of polyamine organic polymer type dispersant |
-
2018
- 2018-11-28 CN CN201811438910.2A patent/CN109517160A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6467378A (en) * | 1987-09-09 | 1989-03-14 | Mitsui Toatsu Chemicals | Desensitizing ink |
| CN104812794A (en) * | 2012-09-28 | 2015-07-29 | 陶氏环球技术有限责任公司 | Adduct compositions |
| CN106188502A (en) * | 2016-07-20 | 2016-12-07 | 江苏丰彩新型建材有限公司 | A kind of self-emulsifying type epoxy hardener, reinforcing varnish and preparation method thereof |
| CN108285533A (en) * | 2017-01-09 | 2018-07-17 | 合记化学股份有限公司 | A kind of polyamine organic polymer type dispersant |
| CN107868241A (en) * | 2017-11-24 | 2018-04-03 | 威海翔泽新材料科技有限公司 | A kind of fatty alcohol block polyether class tar ammonia demulsifier and preparation method thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112375528A (en) * | 2020-11-11 | 2021-02-19 | 广州聚合新材料科技股份有限公司 | Reactive polyurethane hot melt adhesive, preparation method and application |
| CN113336953A (en) * | 2021-06-21 | 2021-09-03 | 宁波润禾高新材料科技股份有限公司 | Modified polyether amine, and preparation method and application thereof |
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Application publication date: 20190326 |