CN110240686A - A kind of high-performance high-hard, transparent polyurethane elastomer and preparation method thereof - Google Patents
A kind of high-performance high-hard, transparent polyurethane elastomer and preparation method thereof Download PDFInfo
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- CN110240686A CN110240686A CN201910352335.2A CN201910352335A CN110240686A CN 110240686 A CN110240686 A CN 110240686A CN 201910352335 A CN201910352335 A CN 201910352335A CN 110240686 A CN110240686 A CN 110240686A
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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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
- C08G18/3814—Polyamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—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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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
Abstract
The invention discloses a kind of high-performance high-hard, transparent polyurethane elastomers, including pre-polymer component and curing agent component；The pre-polymer component includes polytetrahydrofuran polyol, antioxidant, ultraviolet absorbing agent and hexamethylene diisocyanate trimer；The curing agent component includes decoloration MOCA.Preparation method includes the following steps: (1) the prepolymer component being heated to 80 DEG C, then prepolymer component and curing agent component 100:45 in mass ratio are added in the decoloration curing agent of melting, be uniformly mixed；(2) vacuum defoamation is poured into and has been warmed up into 110 DEG C or so of mold, and 30min can mould unloading；(3) the after cure 3-5h in 110 DEG C of baking oven again.Present invention process is simple, short molding cycle, is provided simultaneously with heat-resisting 120 DEG C or more, hardness >=Shao D75 and excellent shock resistance.
Description
Technical field
The invention belongs to technical field of chemical synthesis, more particularly, to a kind of high-performance high-hard, transparent polyurethane elastomer
And preparation method thereof.
Background technique
Middle durometer elastomer and transparent adhesive field are concentrated mainly on to the research of transparent polyurethane material both at home and abroad,
And it is less to the research of high-hard, transparent polyurethane elastomer, meanwhile, the high-hard, transparent polyurethane material of prior art preparation
Mainly have the disadvantage that
1, poor heat resistance: generally it is no more than 80 DEG C using temperature, short-period used temperature is no more than 120 DEG C, 100 DEG C or more, material
It can softening transform；
2, poor toughness: high-hard, transparent polyurethane material impact strength of the hardness greater than Shao D75 will be greatly reduced.
Polyurethane elastomer is a kind of high score as made of oligomer polyol, polyisocyanates and chain extender addition polymerization
Sub- material has many advantages, such as good mechanical property, abrasion performance, resistant to chemical etching.Transparent polyurethane had both had conventional urethane excellent
Mechanical property, and have preferable optical property, be the research direction that new development in recent years is got up, encapsulate in photovoltaic cell,
The fields such as high-intensity protective, high-performance optical instrument and aeronautical material have wide application prospect.But traditional high rigidity is saturating
The heat resistance and shock resistance of bright polyurethane material can not fully meet the requirement of existing application field.
Prior art:
Patent disclosed in Shandong Inov Polyurethane Co., Ltd. " high-hard, transparent polyurethane elastomer and preparation method
(CN104448791A) " one of component is by groups such as compounding polyether polyol, antioxidant, ultraviolet absorbing agent, catalyst
At mixture, another component be by polyether polyol, isocyanates and plasticizer reaction generate prepolymer, the bullet of preparation
Property physical efficiency reach the hardness and transparency of epoxy resin, and the yellowing resistance and toughness incomparable with epoxy.
" the transparent poly- ammonia with high glass transition temperature Tg of patent disclosed in Carcoustics Techconsult GmbH
Ester (CN104861153A) ", which be made of polyisocyanate component and polyol component, wherein polyisocyanates group
Divide average NCO functionality >=3 of per molecule, average OH functionality >=3 of polyol component per molecule, the transparent polyurethane of preparation
Glass transition temperature Tg >=80 DEG C of material.
At 100 DEG C or more, hardness will be greatly reduced the high-hard, transparent polyurethane material of prior art index, material meeting
Softening transform seriously restricts the extensive use of this kind of material.Meanwhile when material hardness is more than Shao D75, although toughness is than common
Epoxy resin is high, but in some special applications, still it is unable to reach requirement.
Summary of the invention
In view of the above technical problems, the present invention draws up for heat-resisting 120 DEG C a kind of or more, hardness >=Shao D75, while having excellent
The transparent polyurethane material of different shock resistance.
The technical solution adopted by the invention is as follows:
A kind of high-performance high-hard, transparent polyurethane elastomer, including pre-polymer component and curing agent component；
The pre-polymer component the preparation method comprises the following steps:
(1) polytetrahydrofuran polyol, antioxidant 1010 and purple by degree of functionality 2, in 250~1000 range of number-average molecular weight
Ultraviolet absorbers UV-328 is added in reaction unit after metering respectively, is heated to 100~120 DEG C while stirring,
Under 0.10MPa negative pressure, vacuum dehydration 2h；
(2) 50 DEG C are cooled to, the hexamethylene diisocyanate trimer of metering is added, warming while stirring to 80-85 DEG C, after
Continuous reaction 2-3h；
(3) when sampling analysis-NCO base content is close to Theoretical Design value, deaeration cooling packing is stand-by；
The curing agent component the preparation method comprises the following steps:
(1) with dimethylbenzene in mass ratio it is that 1:20 is mixed by the powdered activated carbon that diameter is 150 microns, is dispersed with high speed dispersion instrument
Uniformly；
(2) 3, the 3 '-two chloro- 4 of addition decompression melting, 4 '-diaminodiphenylmethane, and being stirred keeps active carbon abundant with it
Contact obtains decoloration MOCA by filtering and being evaporated under reduced pressure.
Further, the hexamethylene diisocyanate trimer and polytetrahydrofuran polyol, antioxidant 1010,
The mass ratio of ultraviolet absorbing agent UV-328 is 100:14~30:0.5~0.7:0.5~0.7.
Further, the active carbon and 3,3 '-two chloro- 4, the mass ratio of 4 '-diaminodiphenylmethane is 1:10.
A kind of high-performance high-hard, transparent method for preparing polyurethane elastic body, comprising the following steps:
(1) the prepolymer component is heated to 80 DEG C, is in mass ratio then 100 by prepolymer component and curing agent component:
45 are added in the decoloration curing agent of melting, quickly stir 1-2min to be uniformly mixed；
(2) vacuum defoamation is poured into and has been warmed up into 110 DEG C or so of mold, and 30min can mould unloading；
(3) high-performance high-hard, transparent polyurethane material is made in the after cure 3-5h in 110 DEG C of baking oven again.
Beneficial effects of the present invention: present invention process is simple, short molding cycle, the high-performance high-hard, transparent being prepared
Polyurethane material is provided simultaneously with heat-resisting 120 DEG C or more, hardness >=Shao D75, while having excellent shock resistance.
Specific embodiment
The contents of the present invention are further elaborated below with reference to specific embodiment, but embodiment is only of the invention
Preferred embodiment, therefore all equivalence changes done according to feature described in present patent application range and principle are included in this
Within the scope of application for a patent for invention.
The percentage of embodiment is mass percent.Main raw material(s) used in embodiment is as follows:
PTMG650 degree of functionality is 2, number-average molecular weight 650, polytetrahydrofuran polyol
PTMG250 degree of functionality is 2, number-average molecular weight 250, polytetrahydrofuran polyol
PTMG1000 degree of functionality is 2, number-average molecular weight 1000, polytetrahydrofuran polyol
N307 degree of functionality is 3, number-average molecular weight 700, polypropylene oxide polyether polyol
N204 degree of functionality is 2, number-average molecular weight 400, polypropylene oxide polyether polyol
N403 degree of functionality is 4, number-average molecular weight 300, polypropylene oxide polyether polyol
N3300 hexamethylene diisocyanate trimer
The MDI of liquefied mdi Carbodiimide-Modified
TDI toluene di-isocyanate(TDI)
MOCA 3,3 '-two chloro- 4,4 '-diaminodiphenylmethane
CHDM 1,4-CHDM
TMP trimethylolpropane
DMEP dimethoxyethyl phthalate
Embodiment 1
Pre-polymer component: degree of functionality 2, the polytetrahydrofuran ether glycol (PTMG250) 12.46% that molecular weight is 250, antioxidant
1010 0.50%, ultraviolet absorbing agent UV328 0.50% and hexamethylene diisocyanate trimer (N3300) 86.54% are pressed
The polyurethane prepolymer that previous process synthesizing isocyanate base content is 15.00%.
Curing agent component: the decoloration 3 prepared by previous process, 3 '-two chloro- 4,4 '-diaminodiphenylmethane (MOCA)
100.00%。
By the control of pre-polymer component temperature at 80 DEG C, the control of curing agent temperature is at 110 DEG C, pre-polymer component and curing agent group
Divide and be uniformly mixed, be poured into 110 DEG C of molds after deaeration, 30min mould unloading, 110 DEG C of baking oven after cure 3h by 100:45 mass ratio,
Obtain the transparent polyurethane material of shore 85D.
Embodiment 2
Pre-polymer component: degree of functionality 2, the polytetrahydrofuran ether glycol (PTMG650) 19.00% that molecular weight is 650, antioxidant
Before 1010 0.50%, ultraviolet absorbing agent UV328 0.50% and hexamethylene diisocyanate trimer (N3300) 80.00% are pressed
State the polyurethane prepolymer that technique synthesizing isocyanate base content is 15.00%.
Curing agent component: the decoloration 3 prepared by previous process, 3 '-two chloro- 4,4 '-diaminodiphenylmethane (MOCA)
100%。
By the control of pre-polymer component temperature at 80 DEG C, the control of curing agent temperature is at 110 DEG C, pre-polymer component and curing agent group
Divide and be uniformly mixed, be poured into 110 DEG C of molds after deaeration, 30min mould unloading, 110 DEG C of baking oven after cure 3h by 100:45 mass ratio,
Obtain the transparent polyurethane material of shore 82D.
Embodiment 3
Pre-polymer component: degree of functionality 2, the polytetrahydrofuran ether glycol (PTMG1000) 22.08% that molecular weight is 1000, antioxygen
Agent 1,010 0.50%, ultraviolet absorbing agent UV328 0.50% and hexamethylene diisocyanate trimer (N3300) 76.92% are pressed
The polyurethane prepolymer that previous process synthesizing isocyanate base content is 15.00%.
Curing agent component: the decoloration 3 prepared by previous process, 3 '-two chloro- 4,4 '-diaminodiphenylmethane (MOCA)
100%。
By the control of pre-polymer component temperature at 80 DEG C, the control of curing agent temperature is at 110 DEG C, pre-polymer component and curing agent group
Divide and is uniformly mixed, is poured into 110 DEG C of molds after deaeration, 30min mould unloading, 110 DEG C of baking oven after cure by 100:45 mass ratio
3h is to get the transparent polyurethane material for arriving shore 80D.
Comparative example 1
Pre-polymer component: degree of functionality 2, the polytetrahydrofuran ether glycol (PTMG250) 12.46% that molecular weight is 250, antioxidant
Before 1010 0.50%, ultraviolet absorbing agent UV328 0.50% and hexamethylene diisocyanate trimer (N3300) 86.54% are pressed
State the polyurethane prepolymer that technique synthesizing isocyanate base content is 15.00%.
Curing agent component: 1,4-CHDM CHDM 81.82%, trimethylolpropane TMP 18.12%, tin class are urged
Agent 0.06%.
By the control of pre-polymer component temperature at 80 DEG C, the control of curing agent temperature is at 110 DEG C, pre-polymer component and curing agent group
Divide and is uniformly mixed, is poured into 110 DEG C of molds after deaeration, 30min mould unloading, 110 DEG C of baking oven after cure by 100:22 mass ratio
3h is to get the transparent polyurethane material for arriving shore 82D.
Comparative example 2
Pre-polymer component: liquefied mdi 100.00%
Curing agent component: degree of functionality 3, number-average molecular weight 700, polypropylene oxide polyether polyol (N307) 59%, degree of functionality
It is 2, number-average molecular weight 400 (N204) 35%, degree of functionality 4, number-average molecular weight 300, polypropylene oxide polyether polyol
(N403) 4.95%, antioxidant 1010 0.50%, 0.50% tin catalyst 0.05% of ultraviolet absorbing agent UV328.
By pre-polymer component and the control of curing agent temperature at 25 ± 2 DEG C, pre-polymer component and curing agent component press 100:135
Mass ratio is uniformly mixed, is poured into room temperature mold after deaeration, 30min mould unloading, and 50 DEG C of baking oven after cure 16h are to get arriving shore
The transparent polyurethane material of 82D.
Comparative example 3
Pre-polymer component: degree of functionality 2, the polytetrahydrofuran ether glycol (PTMG650) 38.18% that molecular weight is 650, three hydroxyl first
Base propane TMP 4.24%, dimethoxyethyl phthalate DMEP 13.29%, antioxidant 1010 0.50%, ultraviolet light are inhaled
It is 12.00% that agent UV328 0.50% and toluene di-isocyanate(TDI) TDI 43.29%, which is received, by previous process synthesizing isocyanate base content
Polyurethane prepolymer.
Curing agent component: the decoloration 3 prepared by previous process, 3 '-two chloro- 4,4 '-diaminodiphenylmethane (MOCA)
100%。
By the control of pre-polymer component temperature at 80 DEG C, the control of curing agent temperature is at 110 DEG C, pre-polymer component and curing agent group
Divide and is uniformly mixed, is poured into 110 DEG C of molds after deaeration, 30min mould unloading, 110 DEG C of baking oven after cure by 100:45 mass ratio
3h is to get the transparent polyurethane material for arriving shore 82D.
The testing performance index result of high-hard, transparent polyurethane material made from Examples 1 to 3 and comparative example 1~3 is such as
Shown in the following table 1.
Table 1
As it can be seen from table 1 the high-performance being prepared using inventive formulation and technique is high compared to other formulas and method
Hardness transparent polyurethane material is provided simultaneously with high transparency, heat-resisting 120 DEG C or more, hardness >=Shao D75, and has excellent anti-impact
Hit performance.
Finally, it should be noted that the foregoing is only a preferred embodiment of the present invention, it is not intended to restrict the invention,
Although the present invention is described in detail referring to the foregoing embodiments, for those skilled in the art, still may be used
To modify the technical solutions described in the foregoing embodiments or equivalent replacement of some of the technical features.
All within the spirits and principles of the present invention, any modification, equivalent replacement, improvement and so on should be included in of the invention
Within protection scope.
Claims (4)
1. a kind of high-performance high-hard, transparent polyurethane elastomer, which is characterized in that including pre-polymer component and curing agent component；
The pre-polymer component the preparation method comprises the following steps:
(1) polytetrahydrofuran polyol, antioxidant 1010 and purple by degree of functionality 2, in 250~1000 range of number-average molecular weight
Ultraviolet absorbers UV-328 is added in reaction unit after metering respectively, is heated to 100~120 DEG C while stirring,
Under 0.10MPa negative pressure, vacuum dehydration 2h；
(2) 50 DEG C are cooled to, the hexamethylene diisocyanate trimer of metering is added, warming while stirring to 80-85 DEG C, after
Continuous reaction 2-3h；
(3) when sampling analysis-NCO base content is close to Theoretical Design value, deaeration cooling packing is stand-by；
The curing agent component the preparation method comprises the following steps:
(1) with dimethylbenzene in mass ratio it is that 1:20 is mixed by the powdered activated carbon that diameter is 150 microns, is dispersed with high speed dispersion instrument
Uniformly；
(2) 3, the 3 '-two chloro- 4 of addition decompression melting, 4 '-diaminodiphenylmethane, and being stirred keeps active carbon abundant with it
Contact obtains decoloration MOCA by filtering and being evaporated under reduced pressure.
2. a kind of high-performance high-hard, transparent polyurethane elastomer according to claim 1, which is characterized in that described six is sub-
The quality of methyl diisocyanate tripolymer and polytetrahydrofuran polyol, antioxidant 1010, ultraviolet absorbing agent UV-328
Than for 100:14~30:0.5~0.7:0.5~0.7.
3. a kind of high-performance high-hard, transparent polyurethane elastomer according to claim 1, which is characterized in that the activity
Charcoal and 3,3 '-two chloro- 4, the mass ratio of 4 '-diaminodiphenylmethane is 1:10.
4. according to claim 1 to any one high-performance high-hard, transparent method for preparing polyurethane elastic body described in 3,
It is characterized in that, comprising the following steps:
(1) the prepolymer component is heated to 80 DEG C, is in mass ratio then 100 by prepolymer component and curing agent component:
45 are added in the decoloration curing agent of melting, quickly stir 1-2min to be uniformly mixed；
(2) vacuum defoamation is poured into and has been warmed up into 110 DEG C or so of mold, and 30min can mould unloading；
(3) high-performance high-hard, transparent polyurethane material is made in the after cure 3-5h in 110 DEG C of baking oven again.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111072901A (en) * | 2019-12-26 | 2020-04-28 | 上海鹤城高分子科技有限公司 | Ultrahigh-hardness high-temperature-resistant casting polyurethane elastomer and preparation method thereof |
| CN112225860A (en) * | 2020-10-12 | 2021-01-15 | 美瑞新材料股份有限公司 | High-hardness thermoplastic polyurethane resin capable of being softened for multiple times at low temperature and application thereof in profile molding |
| CN113929861A (en) * | 2021-10-29 | 2022-01-14 | 山东一诺威聚氨酯股份有限公司 | Heat-insulating transparent low-hardness polyurethane elastomer composition and preparation method thereof |
| CN115059722A (en) * | 2022-05-31 | 2022-09-16 | 江苏省纺织研究所股份有限公司 | Impact-resistant self-repairing multilayer composite material and preparation method thereof |
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| CN111072901A (en) * | 2019-12-26 | 2020-04-28 | 上海鹤城高分子科技有限公司 | Ultrahigh-hardness high-temperature-resistant casting polyurethane elastomer and preparation method thereof |
| CN112225860A (en) * | 2020-10-12 | 2021-01-15 | 美瑞新材料股份有限公司 | High-hardness thermoplastic polyurethane resin capable of being softened for multiple times at low temperature and application thereof in profile molding |
| CN112225860B (en) * | 2020-10-12 | 2022-05-27 | 美瑞新材料股份有限公司 | High-hardness thermoplastic polyurethane resin capable of being softened for multiple times at low temperature and application thereof in profile molding |
| CN113929861A (en) * | 2021-10-29 | 2022-01-14 | 山东一诺威聚氨酯股份有限公司 | Heat-insulating transparent low-hardness polyurethane elastomer composition and preparation method thereof |
| CN113929861B (en) * | 2021-10-29 | 2023-05-05 | 山东一诺威聚氨酯股份有限公司 | Heat-insulating transparent low-hardness polyurethane elastomer composition and preparation method thereof |
| CN115059722A (en) * | 2022-05-31 | 2022-09-16 | 江苏省纺织研究所股份有限公司 | Impact-resistant self-repairing multilayer composite material and preparation method thereof |
| CN115059722B (en) * | 2022-05-31 | 2023-09-29 | 江苏省纺织研究所股份有限公司 | Impact-resistant self-repairing multilayer composite material and preparation method thereof |
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Application publication date: 20190917 |