CN108562690A - A method of it measuring polyurethane synthesis and uses functionality polyols - Google Patents
A method of it measuring polyurethane synthesis and uses functionality polyols Download PDFInfo
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Abstract
This application involves a kind of measurement polyurethane synthesis methods of functionality polyols, obtain one group of intrinsic viscosity IV and degree of functionality F values including the use of polyurethane synthesis glycol known to degree of functionality and low-molecular-weight alcohol, thus fitting obtains the relational expression of IV and F；Polyalcohol by measuring degree of functionality to be measured is formed by the intrinsic viscosity IV of polymer solution, above-mentioned relation formula is substituted into, to obtain the degree of functionality of the polyalcohol.
Description
Technical field
The present invention relates to polyurethane elastomeric fiber fields, and in particular to functionality polyols are used in a kind of synthesis of measurement polyurethane
Method.
Background technology
" degree of functionality " is one of most important structure index of polyurethane synthesis polyalcohol, it is to selecting synthetic catalyst body
System, formula design, the foaming condition of product and application performance are all meaningful, are more aggravated to the polyalcohol of compound initiator
It wants.
Degree of functionality generally cannot be measured directly, but be calculated by measuring number-average molecular weight and the hydroxyl value of polymer substance
It obtains.The measurement of number-average molecular weight mostly uses gel permeation chromatography (GPC), but the equipment price is expensive, need personal management and
It safeguards, hence it is evident that increase the input of enterprise.The measurement of hydroxyl value mostly uses chemical titration, but titration end-point judgement is inaccurate, test
Unstable result, fluctuation are big.It can be seen that the currently used method for measuring degree of functionality requires further improvement, with convenient
It uses.
Therefore, it is necessary to develop a kind of side for measuring polyurethane synthesis with functionality polyols simple, accurate, investment is small
Method.
Invention content
The application embodiment provides a kind of method that functionality polyols are used in the synthesis of measurement polyurethane, including walks as follows
Suddenly：
(1) the mixture a of polyurethane synthesis glycol and low-molecular-weight alcohol known to degree of functionality is prepared, the mixture
Average functionality is expressed as F, and the molecular weight of low-molecular-weight alcohol can be 50 to 200；
(2) so that mixture a is carried out prepolymerization with diisocyanate, obtain pre-polymer solution b；
(3) pre-polymer solution b is subjected to chain extension, obtains polymer solution c；
(4) the intrinsic viscosity IV of polymer solution c is measured；
(5) step (1) to (4) is repeated, obtains one group of IV and F value, and fitting obtains the relational expression of IV and F accordingly；
(6) polyalcohol of degree of functionality to be measured is first closed with diisocyanate prepolymer, then chain extension is carried out by step (3), obtained
Polymer solution, and the intrinsic viscosity of the polymer solution is measured, thus according to the relational expression of IV and F that step (5) obtains
The degree of functionality of the polyalcohol is calculated.
In one embodiment, the degree of functionality of low-molecular-weight alcohol synthesizes the difference with glycol with polyurethane.Low molecular weight
Alcohol is preferably selected from one or more in n-butanol, n-hexyl alcohol, trimethylolpropane, pentaerythrite etc..
In another embodiment, polyurethane synthesis glycol can be selected from polyetherdiol or polyester-diol, preferably poly- four
Hydrogen furans ether glycol.Relative to polyurethane synthesis glycol, the additive amount of low-molecular-weight alcohol can be ppm grades in step (1).
In another embodiment, the average functionality F of mixture can be between 1.8 to 2.2 described in step (1).
In one embodiment, diisocyanate can be methyl diphenylene diisocyanate in step (2)；Prepolymer
The mass concentration of solution b can be 50% to 70%.
In yet another embodiment, chain extension can be by that will contain the solution of chain extender and end-capping reagent dropwise in step (3)
It is added drop-wise to and is carried out in pre-polymer solution b, and stop being added dropwise to determine by indicator color change.Before dropwise addition, pre-polymerization
The mass concentration of object solution b can be 5 to 40%.In yet another embodiment, chain extender and end-capping reagent are all in step (3)
Primary amine, preferred chain extenders are ethylenediamine, and end-capping reagent is cyclohexylamine.
In yet another embodiment, the fit correlation formula of IV and F can be in step (5)：IV=kF-m, wherein k, m are
Constant, goodness of fit coefficient of determination R2>0.98。
In yet another embodiment, the polyalcohol of degree of functionality to be measured can be glycol, and preferably polypropylene glycol or terminal hydroxy group is poly-
Butadiene.
Description of the drawings
Fig. 1 is 1 acquisition IV according to embodiments of the present invention and the substance dosage in a series of experiments of F fit correlation formulas.
Fig. 2 is the fit correlation of the according to embodiments of the present invention 1 several IV and degree of functionality F drawn to IV and F values obtained
Curve.
Abbreviation explanation in attached drawing：
PTG:Polytetramethylene ether diol；UB：N-butanol；TMP:Trimethylolpropane；
MDI：4,4 '-methyl diphenylene diisocyanates；DMAC:Dimethylacetylamide；
EDA：Ethylenediamine；CHA:Cyclohexylamine；IV：Intrinsic viscosity.
Specific implementation mode
In the synthesis of polyurethane elastomeric fiber, high molecular weight polyols are often first directly synthesized, then the latter is used for chain extension
Polymerization.Therefore, it is necessary to the degrees of functionality of measured in advance high molecular weight polyols, just can determine formula design, catalyst system and catalyzing etc..Tradition
Method is generally using chemistry titration in such a way that GPC is combined, but the result that this mode measures is inaccurate, and reproducibility
Difference.
The present invention provides a kind of measurement polyurethane synthesis methods of functionality polyols, i.e., first with known function
The composite result of the polyalcohol of degree obtains the standard curve of intrinsic viscosity IV and degree of functionality F, is then calculated according to the standard curve
The degree of functionality of polyalcohol to be measured.
Specifically, the method for the present invention includes following steps：
(1) the mixture a of polyurethane synthesis glycol and low-molecular-weight alcohol known to degree of functionality is prepared, the mixture
Average functionality is expressed as F, and the molecular weight of low-molecular-weight alcohol can be 50 to 200；
(2) so that mixture a is carried out prepolymerization with diisocyanate, obtain pre-polymer solution b；
(3) pre-polymer solution b is subjected to chain extension, obtains polymer solution c；
(4) the intrinsic viscosity IV of polymer solution c is measured；
(5) step (1) to (4) is repeated, obtains one group of IV and F value, and fitting obtains the relational expression of IV and F accordingly；
(6) polyalcohol of degree of functionality to be measured is first closed with diisocyanate prepolymer, then chain extension is carried out by step (3), obtained
Polymer solution, and the intrinsic viscosity of the polymer solution is measured, thus according to the relational expression of IV and F that step (5) obtains
The degree of functionality of the polyalcohol is calculated.
" polyurethane synthesis glycol " refers to the high molecular weight dihydric alcohol known in the art suitable for synthesis of polyurethane herein,
The number-average molecular weight of the dihydric alcohol is generally 800 to 2100.Specifically, polyurethane synthesis glycol can be selected from polyetherdiol,
Polyester-diol, polyesteramide glycol, polyacrylic acid glycol or combinations thereof.For example, the preferred polyalkylene ether glycols of polyetherdiol, example
Such as polyethylene oxide glycol, polypropylene oxide glycol, polytetramethylene ether diol (PTG or PTMG), polyoxygenated pentamethylene two
The copolymerization polyalkylene ether glycols of the different alkylene ethers composition of alcohol, carbon number 2~10 or their mixture etc..
Herein, the degree of functionality of " low-molecular-weight alcohol " synthesizes the difference with glycol with polyurethane, molecular weight preferably 50 to
200.Those skilled in the art are easily determined suitable specific alcohol according to introduction herein.As an example, low-molecular-weight alcohol can
It is one or more in n-butanol (UB), n-hexyl alcohol, trimethylolpropane (TMP), pentaerythrite etc. to be selected from.
In step (1), the low-molecular-weight alcohol of monohydric alcohol, trihydroxylic alcohol, tetrahydroxylic alcohol or combinations thereof known to degree of functionality is added
It is added in the polyurethane synthesis glycol of bifunctionality so that the degree of functionality of glycol is reduced or increased.It is closed relative to polyurethane
At being ppm grades with the additive amount of glycol, low-molecular-weight alcohol, main function is the degree of functionality for finely tuning polyurethane synthesis glycol.
Since polyurethane synthesis glycol and the respective degree of functionality of low-molecular-weight alcohol and dosage all determine the two it is known that therefore can calculate
It is formed by the average functionality F of mixture a.In one embodiment, the average functionality F of mixture a can 1.8 to
Between 2.2.
" diisocyanate " can be commonly used in the art in those of synthesis of polyurethane, such as aliphatic, alicyclic ring herein
Race, aromatic diisocyanate.4,4 '-methyl diphenylene diisocyanates, 2,4 '-diphenyl methane, two isocyanide can be enumerated
Acid esters, 2,4 toluene diisocyanate and 2,6- toluene di-isocyanate(TDI)s, m xylene diisocyanate and paraxylene two are different
Cyanate, α, α, α ', α '-tetramethyls-xylene diisocyanate, 4,4 '-diphenyl ether diisocyanates, 4,4 '-two hexamethylenes
Group diisocyanate, 1,3- cyclohexylene diisocyanates and 1,4 cyclohexalene diisocyanate, 3- (α-isocyanato- second
Base) phenyl isocyanate, 1,6- hexamethylene diisocyanates, trimethylene diisocyanate, tetramethylene diisocyanate,
Isophorone diisocyanate either their mixture or their copolymer etc..It is preferred that 4,4 '-diphenyl methanes two are different
Cyanate (MDI).
In step (2), mixture a and diisocyanate are subjected to prepolymerization, obtain pre-polymer solution b.Specifically
For, first mixture a is dissolved in amides polar solvent, diisocyanate is added and carries out prepolymerization, obtain matter
Measure the pre-polymer solution b that concentration can be 50%~70%.Diisocyanate synthesized with polyurethane with the amount of the substance of glycol it
Than that can be 1.3 to 2.2, reaction temperature can be 40 to 70 DEG C, and the reaction time can be 30 to 60 minutes.These reaction items
Part is all known in conventional polyurethanes chemical industry skill.
As amides polar solvent, dimethylformamide, dimethylacetylamide etc. can be used.It is preferable to use dimethyl
Acetamide (DMAC).They are all the common solvents of polyurethane-reinforcement reaction.
In step (3), pre-polymer solution b is subjected to chain extension, obtains polymer solution c.Specifically, by chain extender and envelope
End agent is dissolved in and is configured to the solution that mass concentration can be 3 to 10% in amides polar solvent, then the solution is dripped dropwise
It is added in pre-polymer solution b, and determines whether to stop to be added dropwise by indicator color change.Before dropwise addition, prepolymer is molten
The mass concentration of liquid b is preferably controlled in 5 to 40% ranges, this can be realized by adding a certain amount of DMAC.
Herein, chain extender is that polyurethane-reinforcement reacts common amine chain extender, including ethylenediamine, 1,2- propane diamine, 1,
3- propane diamine, 2- methyl-1s, it is 5- pentanediamines, triethylenediamine, xylyene diamine, piperazine, o- phenylenediamine, m-
Phenylenediamine and p-phenylene diamines, 1,3- diaminocyclohexanes, 1,4- diaminocyclohexanes, 1,6- hexamethylene diamines
Deng.They can be used alone or as a mixture.It is preferable to use primary amine chain extenders, such as ethylenediamine (EDA) etc..
Equally, end-capping reagent is also that polyurethane-reinforcement reacts common end-capping reagent, can enumerate isopropylamine, n-butylamine, uncle
Butylamine, 2- ethylhexylamine, cyclohexylamine (CHA) etc..When using primary amine chain extender, preferably end-capping reagent is also primary amine, in this way
The two reactivity is approximate, will not cause test characteristic viscosity number IV values impacted because of reactivity problem.
The mole ratio of the sum of hydroxyl and amido and isocyano can be 1.01 in the entire reaction solution of step (3):1 to
1.10:1, obtain the polymer solution c that mass concentration is 5% to 30%, and the ratio of the amount of the substance of chain extender and end-capping reagent
Example relationship can be 10：1 to 15： 1.
Indicator can use malachite green, when solution is become colorless by blue-green, you can stop that amine aqueous solution is added dropwise.
In step (4), using the intrinsic viscosity IV of determination of ubbelohde viscometer polymer solution c.Intrinsic viscosity is high score
Sub- substance corresponding viscosity in extremely dilute solution.In the present invention, can to use DMAC that polymer solution c is diluted to quality dense
Degree is 0.1 to 5%, then measures intrinsic viscosity.
In step (5), step (1) to (4) is repeated, obtains one group of IV and F value, and fitting obtains the pass of IV and F accordingly
It is formula.Fitting can be completed in common Excel or Origin function plottings application software.The specific group number of IV and F values does not have
It is restricted, but be subject to fit correlation formula and meet basic matched curve precision.In general, fitting be according to curve shape come
Select function model.On experiment basis contemplated herein, a series of pairs of IV and F values are obtained；These data are plotted in
Using degree of functionality F as abscissa, using intrinsic viscosity IV as in the coordinate system of ordinate, shape is formed by according to these points
Determine suitable function model.It is easily accomplished this fitting according to function plotting application software contemplated herein, current.One
In a embodiment, it is constant, goodness of fit coefficient of determination R that the fit correlation formula of IV and F, which are IV=kF-m, wherein k and m,2>
0.98 (namely linear fit).
In step (6), the polyalcohol of degree of functionality to be measured is first closed with diisocyanate prepolymer, then is carried out by step (3)
Chain extension obtains polymer solution, and measures the intrinsic viscosity of the polymer solution, thus according to the fit correlation formula of IV and F
The degree of functionality of the polyalcohol is calculated.The polyalcohol preferred diol of degree of functionality to be measured, more preferable polypropylene glycol or terminal hydroxy group
Polybutadiene.
It is described in more detail the present invention by the following examples, but these embodiments never constitute the limit bright to we
System.
Embodiment one
Obtain the fit correlation formula of IV and F.
According to the dosage in Fig. 1, the mixture a of PTMG and n-butanol UB and/or trimethylolpropane TMP are prepared, is calculated
The average functionality (i.e. theoretical functionality) for obtaining the mixture is F；So that mixture a and MDI is carried out prepolymerization, obtains pre-
Copolymer solution b；Pre-polymer solution b is subjected to chain extension using the DMAC solution of ethylenediamine and cyclohexylamine, obtains polymer solution c；
Measure the intrinsic viscosity IV of polymer solution c.
As an example, the concrete operation step of lot number D20U5 experiments is as follows：
(1) 50g PTMG and 0.025g UB are added in reaction kettle, are subsequently added into 40.81g DMAC dissolvings, calculate
The theoretical functionality for obtaining mixture a is 1.986747.
(2) 11.07g MDI are added into mixture a makes them react 40min at 45 DEG C, and obtaining mass concentration is about
60% pre-polymer solution b.
(3) 48.2g DMAC, 3.115g EDA, 0.514g CHA are weighed and prepares amine aqueous solution；Above-mentioned pre-polymer solution b is molten
Solution is rear in 180.2998g DMAC to be added 2-3 drop malachite green indicator, and above-mentioned amine aqueous solution is added dropwise dropwise, waits for pre-polymer solution
Stop being added dropwise when being become colorless by blue-green, obtains final polymer solution c.
(4) Ubbelohde viscometer is used to measure the IV values of polymer solution c as 0.98316.
The concrete operation step of lot number D20T1 experiments is as follows：
(1) 50g PTMG and 0.005g TMP are added in reaction kettle, are subsequently added into 40.768g DMAC dissolvings, meter
It is 2.001482 to calculate and obtain the theoretical functionality of mixture a.
(2) 11.02g MDI are added into mixture a makes them react 40min at 45 DEG C, and obtaining mass concentration is about
60% pre-polymer solution b.
(3) 48.2g DMAC, 3.115g EDA, 0.514g CHA are weighed and prepares amine aqueous solution；Above-mentioned pre-polymer solution b is molten
Solution is rear in 180.4211g DMAC to be added 2-3 drop malachite green indicator, and above-mentioned amine aqueous solution is added dropwise dropwise, waits for pre-polymer solution
Stop being added dropwise when being become colorless by blue-green, obtains final polymer solution c.
(4) Ubbelohde viscometer is used to measure the IV values of polymer solution c as 0.988.
Equally, with above-mentioned same procedure carry out table in listed other lot numbers experiment, to obtain 19 groups of degree of functionality F and
Corresponding intrinsic viscosity IV values；Will this 19 logarithm input Origin function plotting application software in, fitting obtain IV with
The relation curve of F, as shown in Fig. 2；It can be seen that IV=kF-m, wherein k=1.1218, m=1.2448, coefficient of determination R2
=0.9867.
Embodiment two
The degree of functionality of end hydroxy butadiene HTPB is measured using the fit correlation formula of IV and F.
End hydroxy butadiene be purchased from dawn research institute, number-average molecular weight is about 2000, degree of functionality substantially 2.1-2.2 it
Between.
50g HTPB are added in reaction kettle, 40.67g DMAC is subsequently added into and is dissolved, it is anti-that 11g MDI are then added
It answers, obtains the pre-polymer solution b of mass concentration about 60%.48.2g DMAC, 3.115g EDA, 0.514g CHA is weighed to prepare
Amine aqueous solution；It is added into pre-polymer solution b after 180.4g DMAC carry out dissolved dilution and 2-3 drop malachite green indicator is added,
Above-mentioned amine aqueous solution is added dropwise dropwise, stops being added dropwise when pre-polymer solution is become colorless by blue-green, it is molten to obtain final polymer
Liquid c.
The IV values that Ubbelohde viscometer measures solution c are 1.1805.Formula IV=kF-m (the wherein k obtained according to embodiment 1
=1.1218, m=1.2448), it is 2.1594 to measure degree of functionality F.
Embodiment three
The degree of functionality of polypropylene glycol PPG is measured using the fit correlation formula of IV and F
Polypropylene glycol is purchased from Shandong Nowe new material company, and number-average molecular weight is about 2000, and degree of functionality is about 1.95.
50g PPG are added in reaction kettle, 40.67g DMAC is subsequently added into and is dissolved, it is anti-that 11g MDI are then added
It answers, obtains the pre-polymer solution b of mass concentration about 60%.48.2g DMAC, 3.115g EDA, 0.514g CHA is weighed to prepare
Amine aqueous solution；It is added into pre-polymer solution b after 180.4g DMAC carry out dissolved dilution and 2-3 drop malachite green indicator is added,
Above-mentioned amine aqueous solution is added dropwise dropwise, stops being added dropwise when pre-polymer solution is become colorless by blue-green, it is molten to obtain final polymer
Liquid c.
The IV values that Ubbelohde viscometer measures solution c are 0.9350.Formula IV=kF-m (the wherein k obtained according to embodiment 1
=1.1218, m=1.2448), it is 1.9439 to measure degree of functionality F.
Claims (10)
1. a kind of measuring the polyurethane synthesis method of functionality polyols, include the following steps：
(1) the mixture a of polyurethane synthesis glycol and low-molecular-weight alcohol known to degree of functionality is prepared, the mixture is averaged
Degree of functionality is expressed as F, and the molecular weight of low-molecular-weight alcohol is 50 to 200；
(2) so that mixture a is carried out prepolymerization with diisocyanate, obtain pre-polymer solution b；
(3) pre-polymer solution b is subjected to chain extension, obtains polymer solution c；
(4) the intrinsic viscosity IV of polymer solution c is measured；
(5) step (1) to (4) is repeated, obtains one group of IV and F value, and fitting obtains the relational expression of IV and F accordingly；
(6) polyalcohol of degree of functionality to be measured is first closed with diisocyanate prepolymer, then chain extension is carried out by step (3), polymerize
Object solution, and the intrinsic viscosity of the polymer solution is measured, thus according to the relational expression calculating of IV and F that step (5) obtains
Obtain the degree of functionality of the polyalcohol.
2. according to the method described in claim 1, it is characterized in that the degree of functionality and polyurethane of the low-molecular-weight alcohol in step (1)
The difference of synthesis glycol, the low-molecular-weight alcohol are preferably selected from n-butanol, n-hexyl alcohol, trimethylolpropane, pentaerythrite
It is one or more.
3. method according to claim 1 or 2, it is characterised in that the average functionality F of mixture a described in step (1)
Between 1.8 to 2.2.
4. according to the method in any one of claims 1 to 3, it is characterised in that polyurethane synthesis glycol in step (1)
Selected from polyetherdiol or polyester-diol；It is preferred that polytetrahydrofuran ether glycol.
5. method according to claim 1 to 4, it is characterised in that diisocyanate is hexichol in step (2)
Dicyclohexylmethane diisocyanate.
6. the method according to any one of claims 1 to 5, it is characterized in that in step (2) pre-polymer solution b quality
A concentration of 50% to 70%.
7. method according to any one of claim 1 to 6, it is characterised in that chain extension is by that will contain expansion in step (3)
The solution of chain agent and end-capping reagent is added drop-wise to dropwise to carry out in pre-polymer solution b, and is determined by indicator color change
Stop being added dropwise；It is preferred that the mass concentration of pre-polymer solution b is 5 to 40% before dropwise addition.
8. method according to any one of claim 1 to 7, it is characterised in that chain extender and end-capping reagent be all in step (3)
It is primary amine, preferred chain extenders are ethylenediamine, and end-capping reagent is cyclohexylamine.
9. method according to any one of claim 1 to 8, it is characterised in that the fit correlation formula of IV and F in step (5)
For：IV=kF-m, wherein k and m are constant, goodness of fit coefficient of determination R2>0.98。
10. method according to any one of claim 1 to 9, it is characterised in that the polyalcohol of degree of functionality to be measured is glycol,
It is preferred that polypropylene glycol or end hydroxy butadiene.
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|---|---|---|---|---|
| US6962965B2 (en) * | 2004-02-20 | 2005-11-08 | General Electric Company | Functionalized poly(arylene ether) composition and process |
| CN106680275A (en) * | 2016-12-26 | 2017-05-17 | 上海微谱化工技术服务有限公司 | Method for analyzing polyurethane in polyvinyl chloride system |
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