CN109503804A - A kind of room temperature curing high-performance polyurethane elastomer composition - Google Patents
A kind of room temperature curing high-performance polyurethane elastomer composition Download PDFInfo
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- CN109503804A CN109503804A CN201811504593.XA CN201811504593A CN109503804A CN 109503804 A CN109503804 A CN 109503804A CN 201811504593 A CN201811504593 A CN 201811504593A CN 109503804 A CN109503804 A CN 109503804A
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- room temperature
- polyurethane elastomer
- temperature curing
- elastomer composition
- curing agent
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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
- C08G18/65—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
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3863—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms
- C08G18/3865—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms
- C08G18/3868—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms the sulfur atom belonging to a sulfide group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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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 belongs to polyurethane elastomer field more particularly to a kind of room temperature curing high-performance polyurethane elastomer compositions.Toluene di-isocyanate(TDI) and polytetrahydrofuran ethoxylated polyhydric alcohol synthetic prepolymer component, the function additives such as hydroxy-end capped polyurethane prepolymer, amine chain extender, environmental protection catalyst are mixed into curing agent component.The present invention has the characteristics that simple production process, environmentally friendly, room temperature curing, shaping speed is fast, reaction temperature rising is small, shrinking percentage is low, can be widely used for the fields such as common high abrasion goods, cultural stone mould, artistic floors template, circuit encapsulating and rail traffic.
Description
Technical field
The invention belongs to technical field of polyurethane elastomer, and in particular to a kind of room temperature curing high-performance polyurethane elastomer
Composition.
Background technique
Since nineteen thirty-seven Bayer invention polyurethane, polyurethane has evolved into a complete industrial system, kind packet
Include: soft bubble, hard bubble, half hard bubble, coating, binder, sealant, elastomer etc. become the fifth-largest synthetic material.Elastic polyurethane
Body can be divided into mixed milling type, casting type and three kinds of thermoplastic elastomer (TPE) according to processing method.According to solidification temperature height, casting type is poly-
Urethane elastomer can be divided into hot setting, intermediate temperature setting and three kinds of room temperature curing.Curing polyurethane at room temperature elastomer is main at present
For plastic sports ground, water-repellent paint, floor material, circuit encapsulating, cultural stone mould, artistic floors template etc..It is pre- at present
That there is compound viscosities is big for the curing polyurethane at room temperature elastomer of poly- method, and bubble is not easy to exclude, and addition filler number is few, cost phase
To higher defect.Quasi-prepolymer method curing polyurethane at room temperature elastomer, whether there is free again for TDI type or MDI type
Isocyanate-monomer amount is big, pollutes environment, influences the health of operator, exothermic heat of reaction amount is big, shrinking percentage is big, viscosity increases
The defects of long speed is fast, and the operating time is relatively short.Such as: patent disclosed in Shandong Inov Polyurethane Co., Ltd.
" high-speed rail Special high-strength is poly- for patent disclosed in " room temperature solidification polyurethane elastomer combination (CN102558496A) ", Zhu Leilei
A kind of " the environment-protecting polyurethane plastic cement race of patent disclosed in urethane water-repellent paint (CN108300252A) " and South China Science & Engineering University
The formula design of the target products such as the preparation method (CN103627310A) of the spraying surface in road " is identical, and one of component is
By the isocyanate-terminated semi-prepolymer of oligomer polyol and polyisocyanic acid Lipase absobed, another component is that oligomer is polynary
The mixture of alcohol, diamine chain stretching agent, plasticizer, filler, function additive etc.." it is suitable for room temperature to cast disclosed in Azon USA Inc.
Modeling provides the MDI prepolymer of the liquid stabilising of high-performance polyurethane elastomer and the curative systems of liquid stabilising
(CN1441816A) " formula system and the formula system of patent mentioned above are also almost the same.As existing for this kind of system
Drawback, the application in some fields are restricted.Therefore it is necessary to which research and development are environmentally friendly, shrinking percentage is low, operable time
Relatively long, excellent in mechanical performance room temperature curing high-performance polyurethane elastomer.
Summary of the invention
It is an object of the present invention to provide a kind of room temperature curing high-performance polyurethane elastomer compositions.The composition has room temperature
Solidification, the characteristics of environmentally friendly, shrinking percentage is low, reaction temperature rising is small, operable time is long, excellent in mechanical performance.
The present invention adopts the following technical scheme:
A kind of room temperature curing high-performance polyurethane elastomer composition, including pre-polymer component and curing agent component；
Wherein, the preparation method of pre-polymer component includes the following steps:
1) by degree of functionality 2~3, the polyether polyol in 1000~2000 range of number-average molecular weight is less than 5mmHg vacuum in overbottom pressure
Under, in the lower dehydration of 100~120 DEG C of stirrings to moisture content less than 0.05%；
2) 35~45 DEG C are cooled to, is added dropwise to MDI-50 or TDI while stirring, the reaction system is warming up to 80 after being added dropwise to complete
~85 DEG C, the reaction was continued 2~3 hours；
3) when sampling analysis-NCO base content is close to Theoretical Design value, deaeration cooling packing is stand-by；
Wherein, the preparation method of curing agent component includes the following steps:
Hydroxyl-terminated polyurethane prepolymer, diamine chain stretching agent, plasticizer and function additive are stirred in 100~120 DEG C of reaction kettles
Mix dehydration to moisture content less than 0.05% when, cooling packing is stand-by；
Above-mentioned pre-polymer component and curing agent component are uniformly mixed according to the proper ratio of the mass ratio of 100:12~50, deaeration
After be poured into sample mould, room temperature curing 1~8 hour, obtain the polyurethane elastomer of hardness Shao A55~90.
Preferably, the oligomer polyether polyol is that hydroxy-end capped polyurethane prepolymer, polypropylene oxide ether are polynary
One or more of alcohol, polytetrahydrofuran ethoxylated polyhydric alcohol, polytetrahydrofuran propylene oxide ethoxylated polyhydric alcohol.
Preferably, the chain extender is 3,3 '-two chloro- 4,4 '-diaminodiphenylmethane, 3,5- dimethyl sulphur-based toluene two
One or more of amine, 3,5- dimethyl sulphur-based chlorobenzene diethylenetriamine.
Preferably, the excellent one or more for organo-bismuth, organic zinc, zinc bismuth catalyst of the catalyst.
Preferably, the isocyanates is 2,4- toluene di-isocyanate(TDI), 2,4- toluene di-isocyanate(TDI) and 2,6- toluene
The mixture of diisocyanate, the mixture of 2,4 toluene diisocyanate and 2,6- toluene di-isocyanate(TDI), 4,4 '-diphenyl
Methane diisocyanate, 4,4 '-methyl diphenylene diisocyanates and 2,4 '-methyl diphenylene diisocyanates mixture or
One or more of modified liquefaction methyl diphenylene diisocyanate.
Wherein, after theory setting value refers to that hydroxyl reacts completely with isocyanate group, isocyanate group excessive ideal hundred
Divide specific mass content, can be learnt by calculating, therefore claim theory setting value, passes through design hydroxyl and isocyanates under normal circumstances
The molar ratio of base can calculate theoretical isocyanate percentage composition after molar ratio setting, be the known of those skilled in the art
Technology.
The beneficial effects of the present invention are: by selecting hydroxy-end capped polyurethane prepolymer, prepolymer group in curing agent
Point and curing agent component mixing after it is natural temperature rise reduces immediately, sizing material shrinking percentage is small, operable time extension, mechanical property is excellent
It is different.
Specific embodiment
Invention is further described in detail With reference to embodiment, it should be appreciated that these embodiments are only used for
Illustrate the present invention rather than limits application range of the invention.
The percentage of embodiment is mass percent.Main raw material(s) used in embodiment is as follows:
PTG1000 number-average molecular weight 1000, polytetrahydrofuran polyol
HTPP hydroxyl value is the hydroxyl-terminated polyurethane prepolymer of 136.3~100.1mgKOH/g, is thick liquid under room temperature
TDI-100 2,4 toluene diisocyanate
The chloro- 4,4 '-diaminodiphenylmethane of MOCA 3,3 '-two
DMTDA 3,5- dimethythiotoluene diamine
TX-2 3,5- dimethyl sulphur-based chlorobenzene diethylenetriamine
Bismuth zinc composite catalyst
Embodiment 1:
Pre-polymer component: degree of functionality 2, the polytetrahydrofuran ether glycol (PTG1000) and toluene diisocyanate that molecular weight is 1000
The polyurethane prepolymer that acid esters (TDI-100) is 6.0% by previous process synthesizing isocyanate base content.
Curing agent component: hydroxyl value is the hydroxy-end capped polyurethane prepolymer (HTPP) 29.06%, 3 of 135.2mgKOH/g,
Curing agent group is prepared by previous process in 5- dimethythiotoluene diamine (DMTDA) 70.3%, bismuth zinc composite catalyst 0.64%
Point.
Pre-polymer component and curing agent component are uniformly mixed by 100:18.7 mass ratio, are poured into sample mould after deaeration
In, operable time 28min room temperature curing 168 hours, obtains hardness Shao 89(A) polyurethane elastomer.
Embodiment 2:
Pre-polymer component: same with embodiment 1.
Curing agent component: hydroxyl value be 135.2mgKOH/g hydroxy-end capped polyurethane prepolymer (HTPP) 27.2%, 3,5-
Curing agent component is prepared by previous process in dimethyl sulphur-based chlorobenzene diethylenetriamine (TX-2) 72.2%, bismuth zinc composite catalyst 0.6%.
Pre-polymer component and curing agent component are uniformly mixed by 100:20.0 mass ratio, are poured into sample mould after deaeration
In, operable time 30min room temperature curing 168 hours, obtains hardness Shao 85(A) polyurethane elastomer.
Embodiment 3:
Pre-polymer component is same as Example 1.
Curing agent component: hydroxyl value is the hydroxy-end capped polyurethane prepolymer (HTPP) 39.7%, 3 of 128.5mgKOH/g,
3 '-two chloro- 4,4 '-diaminodiphenylmethane (MOCA) 59.55%, bismuth zinc composite catalyst 0.75% is prepared by previous process
To curing agent component.
Pre-polymer component and curing agent component are uniformly mixed by 100:25.2 mass ratio, are poured into sample mould after deaeration
In, operable time 25min obtains the polyurethane elastomer of 90 Shao A of hardness in room temperature curing 168 hours.
Comparative example 1:
Pre-polymer component: degree of functionality 2, the polytetrahydrofuran ether glycol (PTG1000) 67.57% that molecular weight is 1000, toluene two
Isocyanates (TDI100) 32.43%, the polyurethane prepolymer for being (10.0 ± 0.2) % by previous process synthesizing isocyanate base content
Object.
Curing agent component: degree of functionality 2, the polytetrahydrofuran ether glycol (PTG1000) 67.2%, 3 that molecular weight is 1000,
Curing agent group is prepared by previous process in 5- dimethythiotoluene diamine (DMTDA) 32.6%, bismuth zinc composite catalyst 0.2%
Point.
Pre-polymer component and curing agent component are uniformly mixed by 100:51.8 mass ratio, sample mould is poured into after deaeration
In, operable time 18min room temperature curing 168 hours, obtains hardness Shao 90(A) polyurethane elastomer.
Comparative example 2:
Pre-polymer component: identical as comparative example 1.
Curing agent component: degree of functionality 2, the polytetrahydrofuran diol (PTG1000) 65.1% that molecular weight is 1000,3,5-
Dimethyl sulphur-based chlorobenzene diethylenetriamine (TX-2) 34.7%, bismuth zinc composite catalyst 0.2%, is prepared curing agent component by previous process.
Pre-polymer component and curing agent component are uniformly mixed by 100:53 mass ratio, sample mould is poured into after deaeration
In, operable time 20min room temperature curing 168 hours, obtains hardness Shao 88(A) polyurethane elastomer.
Comparative example 3:
Pre-polymer component: identical as comparative example 1.
Curing agent component: degree of functionality 2, the polytetrahydrofuran diol (PTG1000) 56.0% that molecular weight is 1000,3,3 '-
Two chloro- 4, solidification is prepared by previous process in 4 '-diaminodiphenylmethane (MOCA) 43.7%, bismuth zinc composite catalyst 0.3%
Agent component.
Pre-polymer component and curing agent component are uniformly mixed by 100:50 mass ratio, sample mould is poured into after deaeration
In, operable time 15min room temperature curing 168 hours, obtains the polyurethane elastomer of hardness 92A.
Comparative example 4:
Pre-polymer component is same as Example 1
Curing agent component: hydroxyl value be 106.2mgKOH/g hydroxy-end capped polyurethane prepolymer (HTPP) 31.47%, 3,5- bis-
(methylthiomethyl) diamines (DMTDA) 67.89%, bismuth zinc composite catalyst 0.64%, is prepared curing agent component by previous process.
Pre-polymer component and curing agent component are uniformly mixed by 100:19.6 mass ratio, are poured into sample mould after deaeration
In, operable time 28min room temperature curing 168 hours, obtains hardness Shao 87(A) polyurethane elastomer.
Polyurethane elastomer after synthesizing to above-described embodiment carries out mechanical property parameters test, and test method is as follows:
Shao's A hardness is measured by GB/T531-99, and tensile strength and elongation at break are measured by GB/T528-1992；Other indexs are pressed
GB/T14833-93 measurement.
Wherein, operable time is that viscosity reaches the time of 100000mPas to measure after mixing by material.
Wherein, cure shrinkage is that internal diameter is poured into after mixing material is 20mm, highly to see in the glass tube of 800mm
Contraction height after examining material room temperature curing.
The testing performance index result of polyurethane elastomer made from Examples 1 to 3 and comparative example 1~4 such as the following table 1 institute
Show.
Table 1
As can be seen from Table 1, in the embodiment of the present invention Shao A hardness, tensile strength, elongation at break and 300% stress at definite elongation all with
The polyurethane elastomer difference that the prior art is synthetically prepared is little, and tearing strength, there are also being promoted by a small margin, cure shrinkage is bright
It is aobvious to reduce.
The above description is only a preferred embodiment of the present invention, thus it is all according to the configuration described in the scope of the patent application of the present invention,
The equivalent change or modification that feature and principle are done, is included in the scope of the patent application of the present invention.
Claims (5)
1. a kind of room temperature curing high-performance polyurethane elastomer composition, which is characterized in that including pre-polymer component and curing agent
Component；
Wherein, the preparation method of pre-polymer component includes the following steps:
1) by degree of functionality 2~3, the polyether polyol in 1000~2000 range of number-average molecular weight is less than 5mmHg vacuum in overbottom pressure
Under, in the lower dehydration of 100~120 DEG C of stirrings to moisture content less than 0.05%；
2) 35~45 DEG C are cooled to, is added dropwise to MDI-50 or TDI while stirring, the reaction system is warming up to 80 after being added dropwise to complete
~85 DEG C, the reaction was continued 2~3 hours；
3) when sampling analysis-NCO base content is close to Theoretical Design value, deaeration cooling packing is stand-by；
Wherein, the preparation method of curing agent component includes the following steps:
Hydroxyl-terminated polyurethane prepolymer, diamine chain stretching agent, plasticizer and function additive are stirred in 100~120 DEG C of reaction kettles
Mix dehydration to moisture content less than 0.05% when, cooling packing is stand-by；
Above-mentioned pre-polymer component and curing agent component are uniformly mixed according to the proper ratio of the mass ratio of 100:12~50, deaeration
After be poured into sample mould, room temperature curing 1~8 hour, obtain the polyurethane elastomer of hardness Shao A55~90.
2. a kind of room temperature curing high-performance polyurethane elastomer composition according to claim 1, which is characterized in that described
Oligomer polyether polyol is that hydroxy-end capped polyurethane prepolymer, polypropylene oxide ethoxylated polyhydric alcohol, polytetrahydrofuran ether are polynary
One or more of alcohol, polytetrahydrofuran propylene oxide ethoxylated polyhydric alcohol.
3. a kind of room temperature curing high-performance polyurethane elastomer composition according to claim 1, which is characterized in that described
Chain extender is 3,3 '-two chloro- 4,4 '-diaminodiphenylmethane, 3,5- dimethythiotoluene diamine, 3,5- dimethyl sulphur-based chlorobenzene two
One or more of amine.
4. a kind of room temperature curing high-performance polyurethane elastomer composition according to claim 1, which is characterized in that described
Catalyst be organo-bismuth, organic zinc, zinc bismuth catalyst one or more.
5. a kind of room temperature curing high-performance polyurethane elastomer composition according to claim 1, which is characterized in that described
Isocyanates be 2,4 toluene diisocyanate, 2,4 toluene diisocyanate and 2,6- toluene di-isocyanate(TDI) mixture,
The mixture of 2,4 toluene diisocyanate and 2,6- toluene di-isocyanate(TDI), 4,4 '-methyl diphenylene diisocyanates, 4,
The liquefaction diphenyl of the mixture or modification of 4 '-methyl diphenylene diisocyanates and 2,4 '-methyl diphenylene diisocyanates
One or more of methane diisocyanate.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112538149A (en) * | 2019-09-23 | 2021-03-23 | 万华化学集团股份有限公司 | Preparation process of casting polyurethane elastomer |
| CN114316183A (en) * | 2021-12-31 | 2022-04-12 | 重庆渝启欣科技发展有限公司 | Polyurethane composite material for aviation drawing die and manufacturing method |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112538149A (en) * | 2019-09-23 | 2021-03-23 | 万华化学集团股份有限公司 | Preparation process of casting polyurethane elastomer |
| CN112538149B (en) * | 2019-09-23 | 2022-07-12 | 万华化学集团股份有限公司 | Preparation process of casting polyurethane elastomer |
| CN114316183A (en) * | 2021-12-31 | 2022-04-12 | 重庆渝启欣科技发展有限公司 | Polyurethane composite material for aviation drawing die and manufacturing method |
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