CN106478925A - A kind of preparation technology of super branched polyurethane - Google Patents
A kind of preparation technology of super branched polyurethane Download PDFInfo
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- CN106478925A CN106478925A CN201610906494.9A CN201610906494A CN106478925A CN 106478925 A CN106478925 A CN 106478925A CN 201610906494 A CN201610906494 A CN 201610906494A CN 106478925 A CN106478925 A CN 106478925A
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- mixed liquor
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- branched polyurethane
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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
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
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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
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3275—Hydroxyamines containing two hydroxy groups
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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
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
- C08G18/3814—Polyamines
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a kind of preparation technology of super branched polyurethane, its step：The diethanolamine of 12g 13g and the N of 36g 40g, N dimethyl acetylamide mixed liquor is added in the three-necked bottle equipped with magnetic stirring apparatuss and thermometer；Toluene 2,4 diisocyanate of Deca 17g 18g under condition of ice bath, the N of the dibutyl tin dilaurate of 0.1g 0.2g and 50g 60g, N dimethyl acetylamide mixed liquor, mixed liquor adds cross-linking agent and catalyst；After completion of dropping, rise high-temperature and react to 55 60 DEG C, with the change of NCO group in di-n-butylamine method monitoring system；When NCO group disappears, stopped reaction, it is cooled to room temperature；Pale yellow transparent mixed liquor toluene will be obtained settle 35 times, obtain faint yellow viscous shape fluid, reuse N, N dimethylacetamide amine solvent will preserve, the present invention will adopt one-step synthesis method super branched polyurethane, raw material will be simple and easy to get；Polymer architecture can be controlled by monomer；The selectivity of monomer is most important to reaction.
Description
Technical field
The present invention relates to polyurethane preparing technical field is and in particular to a kind of preparation technology of super branched polyurethane.
Background technology
Dissaving polymer is a field newly emerging and quickly growing in polymer science.Hyperbranched concept by
Flor), propose in nineteen fifty-two, he proposes first in theory by ABnType monomer (n >=2, A, B are reactive group) is intermolecular
Polycondensation, prepares the possibility of highly-branched polymers, has also made some predictions with regard to its characteristic simultaneously.But this do not crystallize, do not tangle
Hyper-branched polymer do not causing extensive attention at that time.Until the nineties in last century, Kim and Wrebster of E.I.Du Pont Company
Prepare the first highly branched polymer Hyperbranched polyphenylene Deng with bromophenylboronic acid as monomer, its low viscous spy
Property is so that people create more keen interest to hyper-branched polymer, and has started substantial amounts of research work, starts from this
One studies dissaving polymer upsurge..
Distinguished according to architectural feature, highly branched polymer can be divided into dendritic (DendriIller) and
Dissaving polymer (HyperbranchedPolymer).They all can be by ABnMonomer synthesizes, and the two both had points of resemblance,
Have any different.Dendritic polymer molecule has regular and controllable branched structure, zero defect in molecule, and rounded, it is high
The whole molecular structure of metric, can supply theoretical research as Model Molecule.Generally they have to pass through the continuous synthesis of multistep to prepare,
Will be through the operation such as separating, purifying after every one-step synthesis, process is very loaded down with trivial details, is unfavorable for commercial production.And hyperbranched polymerization
Thing often can pass through ABnDirect polymerization one step of monomer is obtained, need not careful separating-purifying, simple and easy to get, but hyperbranched polymerization
The branchign of molecule structure of thing not exclusively, often occurs defect, and is difficult to control to because it is branched at random.But hyperbranched poly
Compound has many chemical physical properties and dendritic very close.Therefore dissaving polymer also can rise in a lot of occasions
The effect that can play to dendritic, its being easily-synthesized property industrially is so as to more likely realize extensive in addition
Produce, with more application potential.Dissaving polymer is increasingly paid close attention to by people in recent years, and its research is achieved with breakthrough
Progress.Go deep into exploitation with to dissaving polymer understanding, dissaving polymer must be more widely used.
Content of the invention
For problem above, the invention provides a kind of preparation technology of super branched polyurethane, surpassed using one-step synthesis method
Branched polyurethanes, raw material is simple and easy to get；Polymer architecture can be controlled by monomer；The selectivity of monomer is to reaction
Most important；Molecular weight of product is high, narrow molecular weight distribution：Reaction is difficult gel；Product dissolubility is good, can be with effectively solving background
Problem in technology.
To achieve these goals, the technical solution used in the present invention is as follows：A kind of preparation technology of super branched polyurethane,
Comprise the steps：
（1）The diethanolamine of 12g-13g and the N of 36g-40g, N- is added in the three-necked bottle equipped with magnetic stirring apparatuss and thermometer
Dimethyl acetylamide mixed liquor；
（2）The Toluene-2,4-diisocyanate of Deca 17g-18g under condition of ice bath, 4- diisocyanate, the dibutyl tin cinnamic acid of 0.1g-0.2g
The N,N-dimethylacetamide mixed liquor of stannum and 50g-60g, controls rate of addition so that temperature in bottle is suddenly raised；
（3）Cross-linking agent and catalyst is added in mixed liquor；
（4）After completion of dropping, rise high-temperature and react to 55-60 DEG C, with the change of NCO group in di-n-butylamine method monitoring system；
（5）When NCO group disappears, stopped reaction, it is cooled to room temperature, obtain pale yellow transparent mixed liquor；
（6）Pale yellow transparent mixed liquor toluene will be obtained settle 3-5 time, and obtain faint yellow viscous shape fluid, reuse N, N- diformazan
Yl acetamide dissolving preserves；
According to technique scheme, described diethanolamine, dibutyl tin dilaurate are that chemistry is pure.
According to technique scheme, described N,N-dimethylacetamide is that analysis is pure.
According to technique scheme, described step（2）In rate of addition be 1-3 drop/sec.
According to technique scheme, described step（2）The temperature of middle heating in water bath is 45-50 DEG C.
According to technique scheme, described cross-linking agent adopts amine chain extender MOCA.
According to technique scheme, described catalyst adopts tertiary amine catalyst, from triethylenediamine.
According to technique scheme, described cross-linking agent usage amount is 0.6-0.8g；The usage amount of described catalyst is 0.1-
0.3g.
Beneficial effects of the present invention：
The present invention adopts one-step synthesis method super branched polyurethane, and raw material is simple and easy to get；Polymer architecture can be controlled by monomer
System；The selectivity of monomer is most important to reaction；Molecular weight of product is high, narrow molecular weight distribution：Reaction is difficult gel；Produce
Thing dissolubility is good.
Specific embodiment
In order that the objects, technical solutions and advantages of the present invention become more apparent, with reference to embodiments, to the present invention
It is further elaborated.It should be appreciated that specific embodiment described herein, only in order to explain the present invention, is not used to
Limit the present invention.
Embodiment 1：
A kind of preparation technology of super branched polyurethane, comprises the steps：
（1）The diethanolamine of 12g-13g and the N of 36g, N- diformazan is added in the three-necked bottle equipped with magnetic stirring apparatuss and thermometer
Yl acetamide mixed liquor；
（2）The Toluene-2,4-diisocyanate of Deca 17g under condition of ice bath, 4- diisocyanate, the dibutyl tin dilaurate of 0.1g and 50g's
N,N-dimethylacetamide mixed liquor, controls rate of addition so that temperature in bottle is suddenly raised；
（3）Cross-linking agent and catalyst is added in mixed liquor；
（4）After completion of dropping, rise high-temperature and react to 55 DEG C, with the change of NCO group in di-n-butylamine method monitoring system；
（5）When NCO group disappears, stopped reaction, it is cooled to room temperature, obtain pale yellow transparent mixed liquor；
（6）Pale yellow transparent mixed liquor toluene will be obtained settle 3 times, and obtain faint yellow viscous shape fluid, reuse N, N- dimethyl
Acetyl amine solvent preserves；
According to technique scheme, described diethanolamine, dibutyl tin dilaurate are that chemistry is pure.
According to technique scheme, described N,N-dimethylacetamide is that analysis is pure.
According to technique scheme, described step（2）In rate of addition be 1 drop/sec.
According to technique scheme, described step（2）The temperature of middle heating in water bath is 45 DEG C.
According to technique scheme, described cross-linking agent adopts amine chain extender MOCA.
According to technique scheme, described catalyst adopts tertiary amine catalyst, from triethylenediamine.
According to technique scheme, described cross-linking agent usage amount is 0.6-g；The usage amount of described catalyst is 0.1g.
Embodiment 2：
A kind of preparation technology of super branched polyurethane, comprises the steps：
（1）The diethanolamine of 12.5g and the N of 38g, N- dimethyl is added in the three-necked bottle equipped with magnetic stirring apparatuss and thermometer
Acetamide mixed liquor；
（2）The Toluene-2,4-diisocyanate of Deca 17g-18g under condition of ice bath, 4- diisocyanate, the dibutyl tin dilaurate of 0.15g and
The N,N-dimethylacetamide mixed liquor of 55g, controls rate of addition so that temperature in bottle is suddenly raised；
（3）Cross-linking agent and catalyst is added in mixed liquor；
（4）After completion of dropping, rise high-temperature and react to 57 DEG C, with the change of NCO group in di-n-butylamine method monitoring system；
（5）When NCO group disappears, stopped reaction, it is cooled to room temperature, obtain pale yellow transparent mixed liquor；
（6）Pale yellow transparent mixed liquor toluene will be obtained settle 4 times, and obtain faint yellow viscous shape fluid, reuse N, N- dimethyl
Acetyl amine solvent preserves；
According to technique scheme, described diethanolamine, dibutyl tin dilaurate are that chemistry is pure.
According to technique scheme, described N,N-dimethylacetamide is that analysis is pure.
According to technique scheme, described step（2）In rate of addition be 2 drops/sec.
According to technique scheme, described step（2）The temperature of middle heating in water bath is 47 DEG C.
According to technique scheme, described cross-linking agent adopts amine chain extender MOCA.
According to technique scheme, described catalyst adopts tertiary amine catalyst, from triethylenediamine.
According to technique scheme, described cross-linking agent usage amount is 0.7g；The usage amount of described catalyst is 0.2g.
Embodiment 3：
A kind of preparation technology of super branched polyurethane, comprises the steps：
（1）The diethanolamine of 12g-13g and the N of 40g, N- diformazan is added in the three-necked bottle equipped with magnetic stirring apparatuss and thermometer
Yl acetamide mixed liquor；
（2）The Toluene-2,4-diisocyanate of Deca 18g under condition of ice bath, 4- diisocyanate, the dibutyl tin dilaurate of 0.1g-0.2g and
The N,N-dimethylacetamide mixed liquor of 60g, controls rate of addition so that temperature in bottle is suddenly raised；
（3）Cross-linking agent and catalyst is added in mixed liquor；
（4）After completion of dropping, rise high-temperature and react to 60 DEG C, with the change of NCO group in di-n-butylamine method monitoring system；
（5）When NCO group disappears, stopped reaction, it is cooled to room temperature, obtain pale yellow transparent mixed liquor；
（6）Pale yellow transparent mixed liquor toluene will be obtained settle 3-5 time, and obtain faint yellow viscous shape fluid, reuse N, N- diformazan
Yl acetamide dissolving preserves；
According to technique scheme, described diethanolamine, dibutyl tin dilaurate are that chemistry is pure.
According to technique scheme, described N,N-dimethylacetamide is that analysis is pure.
According to technique scheme, described step（2）In rate of addition be 3 drops/sec.
According to technique scheme, described step（2）The temperature of middle heating in water bath is 50 DEG C.
According to technique scheme, described cross-linking agent adopts amine chain extender MOCA.
According to technique scheme, described catalyst adopts tertiary amine catalyst, from triethylenediamine.
According to technique scheme, described cross-linking agent usage amount is 0.8g；The usage amount of described catalyst is 0.3g.
Based on above-mentioned, it is an advantage of the current invention that the present invention adopts one-step synthesis method super branched polyurethane, raw material is simply easy
?；Polymer architecture can be controlled by monomer；The selectivity of monomer is most important to reaction；Molecular weight of product
Height, narrow molecular weight distribution：Reaction is difficult gel；Product dissolubility is good.
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all essences in the present invention
Any modification, equivalent and improvement made within god and principle etc., should be included within the scope of the present invention.
Claims (8)
1. a kind of preparation technology of super branched polyurethane is it is characterised in that comprise the steps：
（1）The diethanolamine of 12g-13g and the N of 36g-40g, N- is added in the three-necked bottle equipped with magnetic stirring apparatuss and thermometer
Dimethyl acetylamide mixed liquor；
（2）The Toluene-2,4-diisocyanate of Deca 17g-18g under condition of ice bath, 4- diisocyanate, the dibutyl tin cinnamic acid of 0.1g-0.2g
The N,N-dimethylacetamide mixed liquor of stannum and 50g-60g, controls rate of addition so that temperature in bottle is suddenly raised；
（3）Cross-linking agent and catalyst is added in mixed liquor；
（4）After completion of dropping, rise high-temperature and react to 55-60 DEG C, with the change of NCO group in di-n-butylamine method monitoring system；
（5）When NCO group disappears, stopped reaction, it is cooled to room temperature, obtain pale yellow transparent mixed liquor；
（6）Pale yellow transparent mixed liquor toluene will be obtained settle 3-5 time, and obtain faint yellow viscous shape fluid, reuse N, N- diformazan
Yl acetamide dissolving preserves.
2. a kind of super branched polyurethane according to claim 1 preparation technology it is characterised in that described diethanolamine,
Dibutyl tin dilaurate is that chemistry is pure.
3. a kind of preparation technology of super branched polyurethane according to claim 1 is it is characterised in that described N, N- dimethyl
Acetamide is that analysis is pure.
4. a kind of preparation technology of super branched polyurethane according to claim 1 is it is characterised in that described step（2）In
Rate of addition be 1-3 drop/sec.
5. a kind of preparation technology of super branched polyurethane according to claim 2 is it is characterised in that described step（2）In
The temperature of heating in water bath is 45-50 DEG C.
6. a kind of preparation technology of super branched polyurethane according to claim 1 is it is characterised in that described cross-linking agent adopts
Amine chain extender MOCA.
7. a kind of preparation technology of super branched polyurethane according to claim 1 is it is characterised in that described catalyst adopts
Tertiary amine catalyst, from triethylenediamine.
8. a kind of preparation technology of super branched polyurethane according to claim 1 is it is characterised in that described cross-linking agent uses
Measure as 0.6-0.8g；The usage amount of described catalyst is 0.1-0.3g.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2016104103805 | 2016-06-13 | ||
| CN201610410380 | 2016-06-13 |
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| CN106478925A true CN106478925A (en) | 2017-03-08 |
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| WO (1) | WO2017214745A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108864407A (en) * | 2018-08-02 | 2018-11-23 | 北京中纺化工股份有限公司 | A kind of wash resistant water repellent synergist and the preparation method and application thereof |
| CN109646793A (en) * | 2019-02-02 | 2019-04-19 | 江苏长寿棒科技有限公司 | Per urethra prostate dilator and its expansion cracking method |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111138974B (en) * | 2020-01-06 | 2021-10-01 | 浙江大学衢州研究院 | Hyperbranched silane modified polyurethane composite polysiloxane antifouling paint and preparation method thereof |
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| CN108864407A (en) * | 2018-08-02 | 2018-11-23 | 北京中纺化工股份有限公司 | A kind of wash resistant water repellent synergist and the preparation method and application thereof |
| CN109646793A (en) * | 2019-02-02 | 2019-04-19 | 江苏长寿棒科技有限公司 | Per urethra prostate dilator and its expansion cracking method |
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| WO2017214745A1 (en) | 2017-12-21 |
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Application publication date: 20170308 |