CN106519158B - A kind of end group is the preparation method of the hyperbranched poly (urethane-amine) of hydroxyl, interior branch unit with vinyl - Google Patents
A kind of end group is the preparation method of the hyperbranched poly (urethane-amine) of hydroxyl, interior branch unit with vinyl Download PDFInfo
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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
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3848—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing two nitrogen atoms in the 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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
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Abstract
The present invention relates to the preparation methods that a kind of end group is the hyperbranched poly (urethane-amine) of hydroxyl, interior branch unit with vinyl.The present invention synthesizes the novel B containing 3 hydroxyls and 3 vinyl simultaneously first using two degree of functionality vinyloxiranes and three-functionality-degree aminated compounds as raw material, by epoxy-amine ring-opening reaction3B′3Monomer (B represents hydroxyl, B ' represents vinyl)；It then is A with diisocyanate cpd2Monomer and above-mentioned B3B′3Hydroxyl reaction in monomer, composite structure is clear, end group is hydroxyl, interior branch unit hyperbranched poly vinyl-bearing (urethane-amine).Raw material of the present invention is easy to get, step is simple, be prepared a kind of structure-controllable, simultaneously containing hydroxyl and vinyl Liang Zhong functional group, end group and interior branch unit can further functional modification dissaving polymer.
Description
Technical field
It is the hyperbranched poly (urethane-amine) of hydroxyl, interior branch unit with vinyl the present invention relates to a kind of end group
Preparation method, belong to organic polymer field.
Background technique
Hyperbranched polymer molecule in irregular three-dimensional torispherical structure, the molecular weight distribution of dissaving polymer compared with
Width, the degree of branching is between 0 to 1.Although the structure of dissaving polymer is perfect not as good as dendritic, its physical chemistry
Property is very much like with dendritic, and such as good dissolubility, lesser solution and melt viscosity have a large amount of end officials
It can group and molecule internal pore etc..In addition, dissaving polymer the advantages of there are also its own, if synthesis process is simple, can pass through
One-step synthesis method etc..
Wherein, ABn(n >=1) type monomer is the primary raw material of synthesis of super branched polymerization, but commercialized ABnType monomer is deficient
Weary, this hinders the development and industrial application of dissaving polymer significantly.As traditional ABnType polymerization reaction substitute, it is right
Claim monomer to A2And BxThe appearance of (x >=3) polymerization reaction is that the synthesis of dissaving polymer opens a brand-new road.Its
Middle A2With B3Combination be " A2+B3" it is easier to synthesis of super branched polymer.Meanwhile the function of the dissaving polymer prepared at present
Group is substantially distributed in polymer surfaces and structure of functional groups is single, thus to the functional modification of polymer usually on its surface
It carries out, and the work for carrying out functional modification inside it is rarely reported, so preparing a kind of polymer of bi-functional has
Broad application prospect.
Summary of the invention
It is the hyperbranched poly (urethane-amine) of hydroxyl, interior branch unit with vinyl the present invention relates to a kind of end group
Preparation method, can apply in all various aspects, such as in adhesive, polymer blending modification, epoxy curing agent and increasing
The application study in the fields such as tough dose of field, the preparation of hydrogel, the preparation of perforated membrane, photocureable coating and functional coating.
A kind of end group is that hydroxyl, interior branch unit have the hyperbranched poly (urethane-amine) of vinyl, which is characterized in that
Polymer architecture is controllable, contain hydroxyl simultaneously and vinyl Liang Zhong functional group, end group and interior branch unit can further function
Energyization is modified；It is described to utilize allyl glycidyl ether and 1-(2- aminoethyl) piperazine reacts the B prepared3B′3Monomer be raw material and
Hexamethylene diisocyanate passes through A2+B3B′3The structure for reacting the hyperbranched poly (urethane-amine) of preparation is as follows:
The novel B3B′3The preparation method of monomer, the specific steps are as follows: by three-functionality-degree aminated compounds (1 mole),
Two degree of functionality vinyloxiranes (3 moles), methanol or ethyl alcohol (0.1~0.5g/mL) are added at one time reactor,
12-24h is reacted at 60-100 DEG C；Acquired solution is removed into solvent, then vacuum at room temperature by Rotary Evaporators after reaction
Dried overnight, products therefrom is the micro- slime body of pale yellowish oil.
The end group is the preparation method of the hyperbranched poly (urethane-amine) of hydroxyl, interior branch unit with vinyl, tool
Steps are as follows for body: by anhydrous B obtained3B′3Monomer, dibutyl tin dilaurate (0.1%~1%) and anhydrous N, N '-dimethyl methyl
Amide or dry toluene (0.1~0.5g/mL) are added at one time in reactor, after completely dissolution to it, are warming up to 60~100
DEG C, by diisocyanate cpd A2Monomer (B3B′3With A2Molar ratio be 0.5:1~1:1) be added dropwise in mixture,
React 24~48h；Products therefrom is precipitated 3 times in petroleum ether after reaction, obtains final product.
The novel B3B′3The preparation method of monomer, it is characterised in that the two degree of functionality vinyloxiranes choosing
From allyl glycidyl ether, 3,4- epoxy-1-butylenes, one of 1,2- epoxy group -5- hexene.
The novel B3B′3The preparation method of monomer, it is characterised in that the three-functionality-degree aminated compounds is selected from 1-
(2- aminoethyl) piperazine, 4- amino piperidine, 2- aminomethylpiperidine, one of 4- aminomethylpiperidine.
The end group is the preparation method of the hyperbranched poly (urethane-amine) of hydroxyl, interior branch unit with vinyl,
It is characterized in that the diisocyanate cpd A2Monomer is selected from Isosorbide-5-Nitrae-diisocyanate root butane, hexa-methylene diisocyanate
Ester, 1,8-, bis- isocyano group octane, toluene di-isocyanate(TDI), 2,6- toluene-2,4-diisocyanates, 2,5- toluene-2,4-diisocyanates, different Buddhist
That ketone diisocyanate, 4,4 '-di-2-ethylhexylphosphine oxides (phenyl isocyanate), one of 4,4 '-hexylmethanes.
Advantages of the present invention:
1. the present invention passes through A2+B3B′3System preparation has bi-functional dissaving polymer, and synthesis material is easy to get, and synthesizes
Method is simple and yield is high；And the generation of gel phenomenon can be effectively prevented from the case where selecting suitable feed ratio.
2. the present invention is from branched monomer MOLECULE DESIGN, there are two types of the monomer B of functional group for synthesis tool first3B′3, then select
With different A2Monomer utilizes " A2+B3" polymerization, a kind of structure-controllable has been prepared, has contained hydroxyl and ethylene simultaneously
Ji Liangzhong functional group, end group and interior branch unit can further functional modification dissaving polymer.
Detailed description of the invention:
Fig. 1 is novel B3B′3The nucleus magnetic hydrogen spectrum spectrogram of monomer.
Fig. 2 is the nucleus magnetic hydrogen spectrum spectrum that end group is the hyperbranched poly (urethane-amine) of hydroxyl, interior branch unit with vinyl
Figure.
Specific implementation method:
Below in conjunction with specific implementation case, the invention will be further elaborated.It should be understood that the present invention is not limited to following realities
Case is applied, the method is accordingly to be regarded as conventional method unless otherwise instructed.The material unless otherwise instructed can be from open business
Approach obtains.Case 1-14 is the hyperbranched poly (urethane-amine) that a kind of end group is hydroxyl, interior branch unit has vinyl
Prepare case.
Case study on implementation 1
By N- aminoethyl piperazine (2.96g, 22.9mmol), anhydrous methanol (11mL) is added in reactor, stirs and lead to
N220-30min removes oxygen, sufficiently dissolves to it again in strict accordance with N- aminoethyl piperazine and allyl glycidyl ether mole
Ratio than 1:3 allyl glycidyl ether (7.83g, 68.6mmol) is added in mixture, in N2The lower 60 DEG C of oil baths of environment
10h is reacted, is finally colourless transparent liquid.30 DEG C of revolvings of acquired solution are removed into solvent anhydrous methanol, then room temperature in vacuo drying
2h, products therefrom are the micro- slime body of pale yellowish oil.
Case study on implementation 2
By 2- aminomethylpiperidine (2.62g, 22.9mmol), dehydrated alcohol (10mL) is added in reactor, stirs and lead to
N220-30min removes oxygen, sufficiently dissolves to it again in strict accordance with N- aminoethyl piperazine and allyl glycidyl ether mole
Ratio than 1:3 allyl glycidyl ether (7.83g, 68.6mmol) is added in mixture, in N2The lower 60 DEG C of oil baths of environment
10h is reacted, 30 DEG C of revolvings of acquired solution are finally removed into solvent anhydrous methanol, then room temperature in vacuo drying for colourless transparent liquid
2h, products therefrom are the micro- slime body of pale yellowish oil.
Case study on implementation 3
By 4- amino piperidine (2.29g, 22.9mmol), anhydrous methanol (11mL) is added in reactor, stirs and lead to
N220-30min removes oxygen, sufficiently dissolves to it again in strict accordance with 4- amino piperidine and allyl glycidyl ether molar ratio 1:
3 ratio allyl glycidyl ether (7.83g, 68.6mmol) is added in mixture, in N2The lower 60 DEG C of oil baths reaction of environment
30 DEG C of revolvings of acquired solution are finally removed solvent anhydrous methanol, then the dry 2h of room temperature in vacuo, institute for colourless transparent liquid by 10h
Obtaining product is the micro- slime body of pale yellowish oil.
Case study on implementation 4
By N- aminoethyl piperazine (2.96g, 22.9mmol), anhydrous methanol (11mL) is added in reactor, stirs and lead to
N220-30min removes oxygen, sufficiently dissolves to it again in strict accordance with N- aminoethyl piperazine and 3,4- epoxy-1-butylene molar ratio
The ratio of 1:3 3,4- epoxy-1-butylene (4.81g, 68.6mmol) is added in mixture, in N2The lower 60 DEG C of oil baths of environment are anti-
10h is answered, 30 DEG C of revolvings of acquired solution are finally removed into solvent anhydrous methanol, then the dry 2h of room temperature in vacuo for colourless transparent liquid,
Products therefrom is the micro- slime body of pale yellowish oil.
Case study on implementation 5
By B obtained3B′3Monomer (5g, 0.01mol), dibutyl tin dilaurate (0.039g) and toluene 33mL are added to
In reactor, after completely dissolution to it, hexamethylene diisocyanate (Isosorbide-5-Nitrae 7g, 8.25mmol) is dripped by constant pressure at 60 DEG C
Liquid funnel, which is added dropwise in mixture, to react for 24 hours.It is precipitated 3 times in petroleum ether after products therefrom is concentrated after reaction,
It is dried in vacuo a night at room temperature, obtains light yellow clear liquid.
Case study on implementation 6
By B obtained3B′3Monomer (5g, 0.01mol), 0.039g dibutyl tin dilaurate (0.039g) and N, N '-two
Methylformamide (33mL) is added in reactor, after completely dissolution to it, at 80 DEG C by hexamethylene diisocyanate
(1.47g, 8.25mmol) is added dropwise in mixture by constant pressure funnel to react for 24 hours.Gained is produced after reaction
It is precipitated 3 times in petroleum ether after object concentration, is dried in vacuo a night at room temperature, obtains light yellow clear liquid.
Case study on implementation 7
By B obtained3B′3Monomer (5g, 0.01mol), 0.039g dibutyl tin dilaurate (0.039g) and N, N '-two
Methylformamide (33mL) is added in reactor, after completely dissolution to it, at 80 DEG C by Isosorbide-5-Nitrae-diisocyanate root butane
(1.16g, 8.25mmol) is added dropwise in mixture by constant pressure funnel to react for 24 hours.Gained is produced after reaction
It is precipitated 3 times in petroleum ether after object concentration, is dried in vacuo a night at room temperature, obtains light yellow clear liquid.
Case study on implementation 8
By obtained B3B′3Monomer (5g, 0.01mol), 0.039g dibutyl tin dilaurate (0.039g) and toluene (33mL)
It is added in reactor, after completely dissolution to it, 1,8-, bis- isocyano group octane (1.62g, 8.25mmol) is passed through into perseverance at 60 DEG C
Pressure dropping funel, which is added dropwise in mixture, to react for 24 hours.3 are precipitated after products therefrom is concentrated after reaction in petroleum ether
It is secondary, it is dried in vacuo a night at room temperature, obtains light yellow clear liquid.
Case study on implementation 9
By B obtained3B′3Monomer (5g, 0.01mol), dibutyl tin dilaurate (0.039g) and toluene (33mL) are added
Into reactor, after completely dissolution to it, toluene di-isocyanate(TDI) (1.44g, 8.25mmol) is passed through into constant pressure addition at 80 DEG C
Funnel, which is added dropwise in mixture, to react for 24 hours.It is precipitated 3 times in petroleum ether after products therefrom is concentrated after reaction, room
Temperature is lower to be dried in vacuo a night, obtains light yellow clear liquid.
Case study on implementation 10
By B obtained3B′3Monomer (5g, 0.01mol), dibutyl tin dilaurate 0.039g and toluene (33mL) are added to
In reactor, after completely dissolution to it, 2,6- toluene-2,4-diisocyanate (1.44g, 8.25mmol) is dripped by constant pressure at 100 DEG C
Liquid funnel, which is added dropwise in mixture, to react for 24 hours.It is precipitated 3 times in petroleum ether after products therefrom is concentrated after reaction,
It is dried in vacuo a night at room temperature, obtains light yellow clear liquid.
Case study on implementation 11
By B obtained3B′3Monomer (5g, 0.01mol), dibutyl tin dilaurate (0.039g) and toluene (36mL) are added
Into reactor, after completely dissolution to it, 2,5- toluene-2,4-diisocyanate (1.44g, 8.25mmol) is passed through into constant pressure at 80 DEG C
Dropping funel, which is added dropwise in mixture, to react for 24 hours.3 are precipitated after products therefrom is concentrated after reaction in petroleum ether
It is secondary, it is dried in vacuo a night at room temperature, obtains light yellow clear liquid.
Case study on implementation 12
By B obtained3B′3Monomer (5g, 0.01mol), 0.039g dibutyl tin dilaurate (0.039g) and toluene
(33mL) is added in reactor, after completely dissolution to it, 60 DEG C by isophorone diisocyanate (1.83g,
It 8.25mmol) is added dropwise in mixture and is reacted for 24 hours by constant pressure funnel.After products therefrom is concentrated after reaction
It is precipitated 3 times in petroleum ether, is dried in vacuo a night at room temperature, obtain light yellow clear liquid.
Case study on implementation 13
By B obtained3B′3Monomer (5g, 0.01mol), 0.039g dibutyl tin dilaurate (0.039g) and toluene
(33mL) is added in reactor, after completely dissolution to it, at 60 DEG C by 4,4 '-hexylmethanes
(1.97g, 7.5mmol) is added dropwise in mixture by constant pressure funnel to react for 24 hours.After reaction by products therefrom
It is precipitated 3 times in petroleum ether after concentration, is dried in vacuo a night at room temperature, obtain light yellow clear liquid.
Case study on implementation 14
By B obtained3B′3Monomer (5g, 0.01mol), dibutyl tin dilaurate (0.039g) and toluene (33mL) are added
Into reactor, after completely dissolution to it, Isosorbide-5-Nitrae-diisocyanate root butane (1.05g, 7.5mmol) is dripped by constant pressure at 80 DEG C
Liquid funnel, which is added dropwise in mixture, to react for 24 hours.It is precipitated 3 times in petroleum ether after products therefrom is concentrated after reaction,
It is dried in vacuo a night at room temperature, obtains light yellow clear liquid.
Claims (7)
1. a kind of end group is the preparation method of the super branched polyurethane amine of hydroxyl, interior branch unit with vinyl, two are utilized
Degree of functionality vinyloxirane and three-functionality-degree aminated compounds are raw material, simultaneously by the synthesis of epoxy-amine ring-opening reaction
B containing 3 hydroxyls and 3 vinyl3B′3Monomer；It then is A with diisocyanate cpd2Monomer and B3B′3In monomer
Hydroxyl reaction, composite structure is clear, end group is hydroxyl, interior branch unit super branched polyurethane amine vinyl-bearing；It is hyperbranched
Polyurethane amine is characterized in that, reacts the B of preparation with 1- (2- aminoethyl) piperazine using allyl glycidyl ether3B′3Monomer is
Raw material and hexamethylene diisocyanate pass through A2+B3B′3The structural schematic diagram for reacting the super branched polyurethane amine of preparation is as follows:
。
2. a kind of end group according to claim 1 is the super branched polyurethane of hydroxyl, interior branch unit with vinyl
The preparation method of amine, it is characterised in that B3B′3Specific step is as follows for the preparation method of monomer: by 1 mole of three-functionality-degree amine
It closes object, 3 mole of two degree of functionality vinyloxirane, 0.1~0.5g/mL methanol or ethyl alcohol and is added at one time reactor,
12-24h is reacted at 60-100 DEG C；Acquired solution is removed into solvent by Rotary Evaporators after reaction, at room temperature vacuum
Dried overnight, products therefrom is the micro- slime body of pale yellowish oil.
3. a kind of end group is the super branched polyurethane amine of hydroxyl, interior branch unit with vinyl according to claim 1
Preparation method, the specific steps are as follows: by anhydrous B obtained3B′3Monomer, 0.1%~1% dibutyl tin dilaurate and 0.1
The anhydrous n,N-Dimethylformamide of~0.5g/mL or dry toluene are added at one time in reactor, after completely dissolution to it, heating
To 60~100 DEG C, by diisocyanate cpd A2Monomer is with B3B′3With A2Molar ratio 0.5:1~1:1 be added dropwise to it is mixed
It closes in object, reacts 24~48h；Products therefrom is precipitated 3 times in petroleum ether after reaction, obtains final product.
4. a kind of end group is the super branched polyurethane amine of hydroxyl, interior branch unit with vinyl according to claim 1
Preparation method, it is characterised in that the two degree of functionality vinyloxiranes be selected from 3,4- epoxy-1-butylene, 1,2- ring
One of oxygroup -5- hexene.
5. a kind of end group is the super branched polyurethane amine of hydroxyl, interior branch unit with vinyl according to claim 1
Preparation method, it is characterised in that the three-functionality-degree aminated compounds be selected from 4- amino piperidine, 2- aminomethylpiperidine, 4- ammonia
One of methyl piperidine.
6. a kind of end group according to claim 3 is the super branched polyurethane of hydroxyl, interior branch unit with vinyl
The preparation method of amine, it is characterised in that diisocyanate cpd A2It is different that monomer is selected from 1,4- diisocyanate root butane, 1,8- bis-
Cyanooctane, toluene di-isocyanate(TDI), isophorone diisocyanate, 4,4 '-di-2-ethylhexylphosphine oxides (phenyl isocyanate), 4,4 '-two
One of isocyanates dicyclohexyl methyl hydride.
7. a kind of end group according to claim 6 is the super branched polyurethane of hydroxyl, interior branch unit with vinyl
The preparation method of amine, it is characterised in that toluene di-isocyanate(TDI) includes 2,6- toluene-2,4-diisocyanate, 2,5- toluene di-isocyanate (TD.I)s
Ester.
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| CN107652443B (en) * | 2017-10-31 | 2021-01-15 | 江南大学 | Hyperbranched poly (ester-amine) with functional groups on surface and inside and preparation method thereof |
| CN111909356A (en) * | 2020-08-24 | 2020-11-10 | 温州大学新材料与产业技术研究院 | Medical polyurethane material and preparation method thereof |
| CN112745768A (en) * | 2020-12-16 | 2021-05-04 | 泗县钧科新材料科技有限公司 | Chromium-free fingerprint-resistant environment-friendly coating and preparation method thereof |
| CN113416290A (en) * | 2021-05-24 | 2021-09-21 | 洛阳理工学院 | Hyperbranched polyurethane capable of being modified in multiple functionalization manner and preparation method thereof |
| CN113773740A (en) * | 2021-07-28 | 2021-12-10 | 泗县钧科新材料科技有限公司 | Environment-friendly conductive coating and preparation method thereof |
| CN115232318B (en) * | 2022-08-24 | 2023-12-26 | 宁波锋成先进能源材料研究院有限公司 | Nonionic polymer surfactant and preparation method and application thereof |
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| CN105085866A (en) * | 2015-09-02 | 2015-11-25 | 西安交通大学 | Hyperbranched polyurethane containing epoxy groups as well as preparation method and application thereof |
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| US6534600B2 (en) * | 2001-03-26 | 2003-03-18 | Michigan Molecular Institute | Hyperbranched polyureas, polyurethanes, polyamidoamines, polyamides and polyesters |
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| CN101074278A (en) * | 2006-05-09 | 2007-11-21 | 德古萨有限责任公司 | Super branched polyurethane, its preparation method and application |
| CN105085866A (en) * | 2015-09-02 | 2015-11-25 | 西安交通大学 | Hyperbranched polyurethane containing epoxy groups as well as preparation method and application thereof |
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