CN105837788A - A stable NCO prepolymer, a preparing method thereof and use of the prepolymer - Google Patents
A stable NCO prepolymer, a preparing method thereof and use of the prepolymer Download PDFInfo
- Publication number
- CN105837788A CN105837788A CN201610214092.2A CN201610214092A CN105837788A CN 105837788 A CN105837788 A CN 105837788A CN 201610214092 A CN201610214092 A CN 201610214092A CN 105837788 A CN105837788 A CN 105837788A
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- CN
- China
- Prior art keywords
- prepolymer
- nco prepolymer
- stable
- polyalcohol
- naphthalene diisocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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Classifications
-
- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
-
- 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
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
Landscapes
- 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 relates to a stable NCO prepolymer, a preparing method thereof and use of the prepolymer. The NCO content of the prepolymer is 1.2-30 wt%. Viscosity of the prepolymer at 110 DGE C is less than 4500 mPa.s. The prepolymer comprises a mixture of at least one polyol the molecular weight of which is 400-8000 g/mol and the degree of functionality of which is 1.95-3.15 and wax, and a reaction product of a mixture of 1,5-naphthalene diisocyanate and an end capping agent, wherein the polyol is selected from a group consisting of polyester polyol, poly(epsilon-caprolactone) polyol, polycarbonate polyol, polyether polyol and polytetramethylene ether glycol, and the molar ratio of the 1,5-naphthalene diisocyanate to the end capping agent is 1:0.1-0.4. The prepolymer is stable and uniform, can form a stable and clear melt and has a proper viscosity at a processing temperature.
Description
Technical field
The present invention relates to NCO prepolymer, be specifically related to a kind of stable NCO prepolymer and preparation method thereof
And purposes.
Background technology
Prepolymer is the prepolymer of NCO group end-blocking, and it passes through polyalcohol with based on functional group's molar excess
Isocyanates reacts (under special circumstances can also higher than 100 DEG C) until NCO in room temperature to about 100 DEG C
Value reaches constant and obtains.The important application of the prepolymer of this NCO end-blocking is to be prepared as bullet by casting
Gonosome.When preparing this elastomer, prepolymer carries out chain growth the most immediately (namely with short
Chain polyalcohol (such as propane diols) or with polyamines (as methylene two (o-chloraniline) or water react)), or
In order to follow-up chain increases NCO prepolymer cooled (reaching favourable and feasible degree) to lower temperature
(storage temperature) also stores.Cast elastomers can also be by one not only by prepolymer method in principle
Footwork obtains, and the elastomer prepared by prepolymer method has more preferable molecular weight order, it is thus possible to cast
The more preferable elastomer of performance, another favorable characteristics of prepolymer synthetic route is that partial reaction heat is from advance
Poly-step removes, and the reaction heat therefore produced in actual polymerisation process is less, and this is conducive to having of strand
Sequence growth and raising are poured into a mould the reaction time thus are brought ease of processing.
Polyurethane elastomer has a hardness range width because of it, good mechanical performance, return performance and wear-resisting,
Oil resistant, the performance such as ageing-resistant, the seal being widely used in mechanical-hydraulic power train, pneumatic system with
And vapour seal.And in some special domain, then have a tightened up requirement at some special dimensions:
Such as higher mechanical strength, higher high temperature resistant, oil resistant and anti-wear performance, good dynamic mechanical etc..
1,5-naphthalene diisocyanate (NDI) molecule, can due to the symmetry of molecular structure and extremely strong rigidity
So that polyurethane elastomer reaches extraordinary resistance to elevated temperatures and mechanical strength, its elastomer has excellence
Heat-resisting, oil resistant, hydrolysis, wear-resisting and dynamic mechanical.But owing to NDI activity is big, its pre-polymerization
The preservation of body is extremely difficult, becomes hardly possible, and numerous studies work display, its performed polymer can only be 130
Preserving half an hour in the case of DEG C, in the case of 100 DEG C, the holding time was the most very limited, less than 1 day
Time.
Summary of the invention
The technical problem to be solved is to overcome the deficiencies in the prior art, it is provided that a kind of stable NCO
Prepolymer, this prepolymer is stable and uniform, it is possible to forming stable and transparent melt, it can be in processing temperature
There is suitable viscosity.
The present invention also provides preparation method and the purposes of a kind of stable NCO prepolymer simultaneously, and the method is easy
In adjusting formula, simple to operate.
For solving above technical problem, a kind of technical scheme that the present invention takes is:
A kind of stable NCO prepolymer, the content of its NCO is 1.2～30wt.%, viscosity when 110 DEG C
Less than 4500mPa.s, including
(1) at least one molecular weight is between 400～8000g/mol, degree of functionality be 1.95～3.15 polynary
Alcohol and the mixture of wax, polyalcohol is selected from PEPA, poly-6-caprolactone polyalcohol, polycarbonate polyol
Alcohol, PPG and PTMG；With
(2) 1,5-naphthalene diisocyanate and the product of end-capping agent mixture, 1,5-naphthalene diisocyanate and envelope
The mol ratio of end agent is 1:0.1～0.4.
Preferably, end-capping reagent is the alcohols containing a hydroxyl.
It is further preferred that end-capping reagent is hexadecanol.
Preferably, wax is Tissuemat E.
The another technical scheme that the present invention takes is:
The preparation method of a kind of stable NCO prepolymer, comprises the steps:
A, by 1,5-naphthalene diisocyanate be heated to 130 DEG C become supernatant liquids, according to formula ratio add end-capping reagent
Block；
B, polyalcohol is heated to 80 DEG C～100 DEG C, adds the wax of formula ratio, stir with homogenizer,
Stir 20～40 minutes；
C, the raw material in above-mentioned steps b is controlled speed by measuring pump so that raw material disposably adds step
In the end-blocking thing that a obtains, then stirring with homogenizer, mixing time is 0～10 minute, and stirring completes
Rear holding mixeding liquid temperature is 90～120 DEG C, mixed liquor pours into container package and preserves, to obtain final product.
Preferably, 1,5-naphthalene diisocyanate is 1:0.1～0.4 with the mol ratio of end-capping reagent.
It is further preferred that the mixing speed in step b is higher than 1000r/min.
Preferably, the mixing speed in step c is higher than 2000r/min.
The purposes of the NCO prepolymer of aforementioned stable, for reacting preparation cast bullet with isocyanate-reactive material
Gonosome or for preparing thermoplastic polyurethane elastic with isocyanate-reactive material by batch (-type) or continous way
Body.
Actual prepare cast elastomers time, in addition it is also necessary to add one or more appropriate chain extenders.Chain extender
Refer to diethanol, diethylene glycol, propane diols, 1,4-butanediol, hexylene glycol, pentanediol, trimethylolethane,
Glycerine, trimethylolpropane, polycaprolactonetriol, 3,3 '-two chloro-4,4 '-diphenylmethanediamiands (MOCA),
3,5-dimethythiotoluene diamine (DMTDA), 3,5-diethyl toluene diamine (DETDA), 4,4 '-methylene
Base double (3-chloro-2,6-diethyl) aniline (MCDEA), ethylenediamine (DA), N, N-dihydroxy (diisopropyl)
Aniline (HPA), quinhydrones-two (beta-hydroxyethyl) ether (HQEE).
Also need in the case of Te Ding add catalyst, stabilizer, emulsifying agent.
Suitably catalyst has dibutyl tin dilaurate, N-alkyl morpholine, lead octoate, diazabicyclooctane
Deng.
Suitably stabilizer can be Bronsted and lewis acid, than example hydrochloric acid, boron chloride, oneself two
Acid, glutaric acid, maleic acid, citric acid etc..
Due to the employing of above technical scheme, the present invention compared with prior art has the advantage that
NDI is first melted by the present invention in advance, be subsequently adding hexadecanol end-blocking reduce its activity, simultaneously we
In polyalcohol, add wax reduce its viscosity and shearing force, under homogenizer, it is quickly mixed, due to
Polyalcohol temperature is relatively low, and after adding polyalcohol, the mixture temperature of NDI and end-capping reagent drastically declines, at height
In the case of speed mixer, ensure that NDI& end-capping reagent is uniform with polyalcohol & wax dispersed with stirring, mixed simultaneously
Liquid is cooled to 90～120 DEG C and ensure that its performance is never degenerated, and has finally prepared NCO prepolymer.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is described in further details.Should be understood that these embodiments are
For the general principle of the present invention, principal character and advantage are described, and the present invention is not by the model of following example
Enclose restriction.The implementation condition used in embodiment can do adjustment further according to specific requirement, not marked
Implementation condition is usually the condition in normal experiment.
Embodiment 1
By the 1 of 332g, 5-naphthalene diisocyanate (NDI) is heated to 130 DEG C and becomes supernatant liquid, is subsequently adding
77g hexadecanol blocks, and stirs 30 minutes；By the poly-6-caprolactone polyalcohol (PCL) of 1000g
It is heated to 80 DEG C～100 DEG C, adds the Tissuemat E of 50g, stir with homogenizer, mixing speed
Higher than 1000r/min, stir 20～40 minutes；Speed is controlled, by polynary for poly-6-caprolactone by measuring pump
The compound of alcohol (PCL) and Tissuemat E disposably adds in the mixture of NDI and hexadecanol, then
Using homogenizer high-speed stirred, mixing speed is higher than 2000r/min, and mixing time is shorter than 10 minutes, stirs
Keeping mixeding liquid temperature after having mixed is 90～120 DEG C, then mixed liquor pours into container package and preserves.
Prepolymer is divided into after many group samples test sample under different storage temperatures, and sample test comprises 110
Viscosity, outward appearance and nco value at DEG C.
The test result of each test sample in table 1 embodiment 1
Embodiment 2
Prepolymer in embodiment 1 is heated to 120 DEG C, and after degassing, the BDO with 75g weight mixes
Chain extension, is then poured in the mould scribbling releasing agent, places into solidification 2 in the convection oven of 130 DEG C little
The demoulding time after, continues to put into baking oven and takes out test performance after 20 hours.
The performance test results of each test sample in table 2 embodiment 2
Embodiment 3
By the 1 of 332g, 5-naphthalene diisocyanate (NDI) is heated to 130 DEG C and becomes supernatant liquid, is subsequently adding
The hexadecanol of 77g blocks, and stirs 30 minutes；By the poly-6-caprolactone polyalcohol (PCL) of 1000g
It is heated to 80 DEG C～100 DEG C, adds the Tissuemat E of Different Weight, stir with homogenizer, stirring
Speed is higher than 1000r/min, stirs 20～40 minutes；Speed is controlled, by poly-6-caprolactone by measuring pump
The compound of polyalcohol (PCL) and Tissuemat E disposably adds in the mixture of NDI and hexadecanol,
Then using homogenizer high-speed stirred, mixing speed is higher than 2000r/min, and mixing time is shorter than 10 minutes,
Having stirred rear mixeding liquid temperature is 90～120 DEG C, then mixed liquor pours into container package and preserves.
Prepolymer is divided into after many group samples test sample at a temperature of same stored, and sample test comprises 110
Viscosity at DEG C, outward appearance.
The test result of each test sample under Different Weight Tissuemat E in table 3 embodiment 3
By above-mentioned table 1 and table 3 result it can be seen that the NCO prepolymer of the present invention can be 90～120 DEG C of guarantors
Demonstrate,prove its performance to never degenerate.
Being described in detail the present invention above, the explanation of embodiment is only intended to help to understand the present invention's
Method and core concept thereof, the present invention's is interior to its object is to allow the personage being familiar with this art will appreciate that
Hold and implement according to this, can not limit the scope of the invention with this.All according to spirit of the invention institute
The equivalence change made or modification, all should contain within protection scope of the present invention.
Claims (10)
1. a stable NCO prepolymer, it is characterised in that: the content of its NCO is 1.2 ~ 30wt.%, and viscosity when 110 DEG C is less than 4500mPa.s, including
(1) at least one molecular weight is between 400 ~ 8000g/mol, degree of functionality is polyalcohol and the mixture of wax of 1.95 ~ 3.15, and described polyalcohol is selected from PEPA, poly-6-caprolactone polyalcohol, polycarbonate polyol, PPG and PTMG；With
(2) 1,5-naphthalene diisocyanate and the product of end-capping agent mixture, described 1,5-naphthalene diisocyanate is 1:0.1 ~ 0.4 with the mol ratio of described end-capping reagent.
Stable NCO prepolymer the most according to claim 1, it is characterised in that: described end-capping reagent is the alcohols containing a hydroxyl.
Stable NCO prepolymer the most according to claim 2, it is characterised in that: described end-capping reagent is hexadecanol.
Stable NCO prepolymer the most according to claim 1, it is characterised in that: described wax is Tissuemat E.
5. the preparation method of the stable NCO prepolymer described in claim any one of a claim 1 ~ 4, it is characterised in that: comprise the steps:
A, by 1,5-naphthalene diisocyanate be heated to 130 DEG C become supernatant liquids, according to formula ratio add end-capping reagent block；
B, polyalcohol is heated to 80 DEG C ~ 100 DEG C, adds the wax of formula ratio, stir with homogenizer, stir 20 ~ 40 minutes；
C, the raw material in above-mentioned steps b is controlled speed by measuring pump, raw material is made disposably to add in the end-blocking thing that step a obtains, then stir with homogenizer, mixing time is 0 ~ 10 minute, keeping mixeding liquid temperature after having stirred is 90 ~ 120 DEG C, mixed liquor pours into container package preserve, to obtain final product.
The preparation method of stable NCO prepolymer the most according to claim 5, it is characterised in that: described 1,5-naphthalene diisocyanate is 1:0.1 ~ 0.4 with the mol ratio of described end-capping reagent.
The preparation method of stable NCO prepolymer the most according to claim 5, it is characterised in that: the mixing speed in described step b is higher than 1000r/min.
The preparation method of stable NCO prepolymer the most according to claim 5, it is characterised in that: the mixing speed in described step c is higher than 2000r/min.
9. according to the purposes of the stable NCO prepolymer described in claim any one of claim 1 ~ 4, it is characterised in that: cast elastomers is prepared in described NCO prepolymer and isocyanate-reactive material reaction.
10. according to the purposes of the stable NCO prepolymer described in claim any one of claim 1 ~ 4, it is characterised in that: described NCO prepolymer and isocyanate-reactive material prepare TPUE by batch (-type) or continous way.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610214092.2A CN105837788A (en) | 2016-04-07 | 2016-04-07 | A stable NCO prepolymer, a preparing method thereof and use of the prepolymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610214092.2A CN105837788A (en) | 2016-04-07 | 2016-04-07 | A stable NCO prepolymer, a preparing method thereof and use of the prepolymer |
Publications (1)
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| CN105837788A true CN105837788A (en) | 2016-08-10 |
Family
ID=56597896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610214092.2A Pending CN105837788A (en) | 2016-04-07 | 2016-04-07 | A stable NCO prepolymer, a preparing method thereof and use of the prepolymer |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438670A (en) * | 2018-11-13 | 2019-03-08 | 佛山市华博润材料科技有限公司 | Soft thermoplastic polyurethane elastomers of high transparency and its preparation method and application |
| CN110437422A (en) * | 2019-06-25 | 2019-11-12 | 广东元星工业新材料有限公司 | A kind of preparation method and application of stable NDI performed polymer |
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| CN1229825A (en) * | 1993-07-28 | 1999-09-29 | 北美埃尔夫爱托化学股份有限公司 | Product produced by composition containing blocked isocyanates |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438670A (en) * | 2018-11-13 | 2019-03-08 | 佛山市华博润材料科技有限公司 | Soft thermoplastic polyurethane elastomers of high transparency and its preparation method and application |
| CN110437422A (en) * | 2019-06-25 | 2019-11-12 | 广东元星工业新材料有限公司 | A kind of preparation method and application of stable NDI performed polymer |
| CN110437422B (en) * | 2019-06-25 | 2022-07-08 | 广东元星工业新材料有限公司 | Preparation method and application of stable NDI prepolymer |
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