CN101649037A - Polybutadiene polyurethane (polyurethane-urea) containing polythiol - Google Patents
Polybutadiene polyurethane (polyurethane-urea) containing polythiol Download PDFInfo
- Publication number
- CN101649037A CN101649037A CN200910183313A CN200910183313A CN101649037A CN 101649037 A CN101649037 A CN 101649037A CN 200910183313 A CN200910183313 A CN 200910183313A CN 200910183313 A CN200910183313 A CN 200910183313A CN 101649037 A CN101649037 A CN 101649037A
- Authority
- CN
- China
- Prior art keywords
- polyurethane
- urea
- polybutadiene
- groups
- polythiol
- 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
Links
- 239000005062 Polybutadiene Substances 0.000 title claims abstract description 29
- 229920002857 polybutadiene Polymers 0.000 title claims abstract description 29
- 229920003226 polyurethane urea Polymers 0.000 title claims abstract description 23
- 229920006295 polythiol Polymers 0.000 title claims abstract description 20
- 229920002635 polyurethane Polymers 0.000 title abstract description 8
- 239000004814 polyurethane Substances 0.000 title abstract description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- -1 chloro- Chemical class 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 239000011248 coating agent Substances 0.000 abstract description 7
- 238000000576 coating method Methods 0.000 abstract description 7
- 239000012948 isocyanate Substances 0.000 abstract description 6
- 150000002513 isocyanates Chemical class 0.000 abstract description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract description 4
- 125000003700 epoxy group Chemical group 0.000 abstract description 3
- 238000004382 potting Methods 0.000 abstract description 3
- 230000007704 transition Effects 0.000 abstract description 3
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 2
- 239000000853 adhesive Substances 0.000 abstract 1
- 239000003292 glue Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 239000004587 polysulfide sealant Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 239000012496 blank sample Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
Abstract
The invention relates to polybutadiene polyurethane (polyurethane-urea) containing mercaptan reaction active groups. Compared with other kinds of polybutadiene polyurethane (polyurethane-urea), the polybutadiene polyurethane (polyurethane-urea) of the invention has the biggest difference that the polybutadiene polyurethane (polyurethane-urea) of the invention contains a small amount of polythiol;and the polythiol is an oligomer which comprises a plurality of sh groups (SH) and oxhydryl groups (OH). By using the characteristic that the reaction activity of the oxhydryl groups in the polythiolwith isocyanate is obviously higher than the reaction activity of the SH groups with the isocyanate, after the oxhydryl groups react with the isocyanate, mercaptan is reserved as an active group and can react with other groups such as epoxy groups, the isocyanate, the SH groups, and the like later. The polybutadiene polyurethane (polyurethane-urea) containing mercaptan reaction active groups can be singly used as a potting polybutadiene polyurethane (polyurethane-urea) coating and adhesive, and can be coated on the surfaces of other polybutadiene products and used as a transition layer so as to effectively improve the bonding property of a finished polybutadiene product.
Description
(1) technical field
A kind of polybutadiene polyurethane (urea) that contains polythiol belongs to seal gum, coating, potting compound field.
(2) background technology
Polybutadiene polyurethane (urea) had both had the good performance of general polyurethane, the characteristic that natural rubber is arranged again, as low temperature kindliness, water tolerance, therefore obtained using widely in fields such as tackiness agent, electronic industry, elastomerics, coating, separation membrane materials.Owing to do not contain polarity utmost point group on the polyhutadiene main chain, and fluid rubber is easy to cast molding, and therefore hermetically sealed cable plug, the common polyethers of electrical device pouring sealant geometric ratio and the PAUR of making has better water tolerance and good electrical property.Polybutadiene polyurethane (urea) also can be widely used in makes the good clad steel of protective system, electrical insulating coating, low thermo-paint and anti-sea-water corrosion performance etc., has good sealing property, is suitable for life-time service under water.
" polymer circular " 2003 the 1st phases of periodical describe performance, constructional feature and main application of polybutadiene polyurethane (urea) in detail, elder generation is by the reaction of hydroxyl on the diisocyanate terminated polyhutadiene, the preparation performed polymer, then use alcohol or amine and performed polymer chain extending reaction, finally obtain polybutadiene polyurethane (urea) elastomerics, wherein soft section (polyhutadiene) content is 50%～85%, and hard section (chainextenders such as isocyanic ester and alcohol) content is 15%～50%.
Because polar functionalities not on the polyhutadiene main chain, when being successfully applied to hermetically sealed cable plug, electrical device pouring sealant, protective system, electrical insulating coating and low thermo-paint, find that polyhutadiene glue is directly exposed in the air, then its anti-ultraviolet, performance such as aging is not enough and can ftracture, but the type glue is low owing to polarity, and is difficult for by other finish paint coating, bonding, the covering of seal gum institute; In other application scenarios, as primary coat, when other continue embedding in the above as glue such as poly-sulphur, epoxies, can occur the phenomenon that the interface breaks away from equally again, cause adhesive effect undesirable as brushing polyhutadiene coating.
Patent (international application no PCT/JP2004/019296, domestic application number 200480038966) has been invented a kind of method that engages (bonding) power that improves polybutadiene molded article and polar resin moulding product, and further improves engaging force by the solvent of selection (combination) these moulding product.The adhering method of polybutadiene molded article, it comprises: (1) thus bonding operation is carried out with polybutadiene molded article and the polar resin moulding product that water contact angle is reduced in polybutadiene molded article carries out that ozonize, electron rays processing, Corona discharge Treatment, plasma discharge are handled, ultraviolet laser is handled or chemical treatment reduces the surperficial water contact angle of these moulding product operation and (2).
(3) summary of the invention
The present invention has prepared a kind of polybutadiene polyurethane (urea) that contains polythiol, compares with other polybutadiene polyurethane (urea), and maximum difference is to contain a certain amount of polythiol in material.The polythiol that the present invention adopts is that Japanese Yuka Shell Epoxy Kabushiki Kaisha company produces trade(brand)name Capcure3-800.This polythiol is a kind of oligopolymer that has a plurality of thiol groups (SH) and hydroxyl (OH) simultaneously, the modification of the industrial low temperature curing agent that often is used to do Resins, epoxy, poly-sulphur glue.The present invention utilizes the reactive behavior of hydroxyl and isocyanic ester in the polythiol resin apparently higher than thiol group and the active characteristics of isocyanate reaction, behind hydroxyl and isocyanate reaction, mercaptan then is retained as active group, can be afterwards and reactions such as other epoxy group(ing), isocyanic ester, thiol group, finally improve the bonding force of polybutadiene polyurethane (urea) and other glue kinds.
This polybutadiene polyurethane (urea) that contains the polythiol reaction active groups of invention, promptly can be separately as polybutadiene polyurethane (urea) seal gum, tackiness agent, potting compound uses, also can brush surface at other polyhutadiene goods, as transition layer, effectively improve the cementability of polyhutadiene goods.
The present invention consists of: isocyanate-terminated polyhutadiene performed polymer 100 weight parts, polythiol 1～20 weight part, organotin promotor 0～0.5 weight part, butyleneglycol 0～5 weight part, 3,6-diformazan sulfenyl-2,5-two carbaryls 4～15 weight parts, 3,6-diethyl-2,5-two carbaryls 0～15 weight part, 3,3 '-two chloro-, 4,4 ' ditan diamines, 0～15 weight part, butanone 0～300 weight part, toluene or dimethylbenzene 0.～300 weight part, tetrahydrofuran (THF) 0～300 weight part.
(4) specific embodiments of the invention
In the present embodiment, isocyanate-terminated polyhutadiene performed polymer 100 weight parts, 3,6-diformazan sulfenyl-2,5-two carbaryls 10 weight parts, organotin promotor 0.01 weight part, butyleneglycol 0.05 weight part, 3,6-diethyl-2,5-two carbaryls 1 weight part, 3,3 '-two chloro-4,4 ' ditan diamines, 1 weight part, butanone 40 weight parts, toluene 30 weight parts, tetrahydrofuran (THF) 1 weight part, and polythiol content is respectively 0,1,3,5,7 weight parts, respectively as blank sample, embodiment 1, embodiment 2, embodiment 3 and embodiment 4.Each sample body intensity of measuring, elongation at break reach and the bonding shearing resistance of polysulfide sealant sees Table 1.
Table 1 contains the polybutadiene polyurethane (urea) of polythiol
Table 1 result shows: the adding polythiol is little to the bulk properties influence of polybutadiene polyurethane (urea), and polysulfide sealant and blank sample, embodiment 1, embodiment 2, embodiment 3 and embodiment 4 bonding after, the bonding shearing resistance that contains embodiment 1, embodiment 2, embodiment 3 and the embodiment 4 and the polysulfide sealant of polythiol obviously improves, also from polybutadiene polyurethane (urea) and polysulfide sealant interfacial failure, transition is the polysulfide sealant cohesive failure to the destruction situation.
Claims (2)
1. polybutadiene polyurethane (urea) that contains polythiol, it is characterized in that, consist of: isocyanate-terminated polyhutadiene performed polymer 100 weight parts, polythiol 1～20 weight part, organotin promotor 0～0.5 weight part, butyleneglycol 0～5 weight part, 3,6-diformazan sulfenyl-2,5-two carbaryls 4～15 weight parts, 3,6-diethyl-2,5-two carbaryls 0～15 weight part, 3,3 '-two chloro-, 4,4 ' ditan diamines, 0～15 weight part, butanone 0～300 weight part, toluene or dimethylbenzene 0.～300 weight part, tetrahydrofuran (THF) 0～300 weight part.
2. the polybutadiene polyurethane (urea) that contains polythiol according to claim 1 is characterized in that polythiol is trade(brand)name Capcure3-800.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910183313A CN101649037A (en) | 2009-09-17 | 2009-09-17 | Polybutadiene polyurethane (polyurethane-urea) containing polythiol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910183313A CN101649037A (en) | 2009-09-17 | 2009-09-17 | Polybutadiene polyurethane (polyurethane-urea) containing polythiol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101649037A true CN101649037A (en) | 2010-02-17 |
Family
ID=41671379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200910183313A Pending CN101649037A (en) | 2009-09-17 | 2009-09-17 | Polybutadiene polyurethane (polyurethane-urea) containing polythiol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101649037A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110256992A (en) * | 2019-07-15 | 2019-09-20 | 江苏方成生物科技有限公司 | A kind of high-performance electronic glue |
| CN110885420A (en) * | 2019-12-03 | 2020-03-17 | 固诺（天津）实业有限公司 | Foam filling agent capable of being rapidly cured in low-temperature environment |
| CN112094572A (en) * | 2020-09-18 | 2020-12-18 | 重庆艾普防腐技术有限公司 | Novel water-based epoxy coating for ship engine shell and preparation method thereof |
-
2009
- 2009-09-17 CN CN200910183313A patent/CN101649037A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110256992A (en) * | 2019-07-15 | 2019-09-20 | 江苏方成生物科技有限公司 | A kind of high-performance electronic glue |
| CN110885420A (en) * | 2019-12-03 | 2020-03-17 | 固诺（天津）实业有限公司 | Foam filling agent capable of being rapidly cured in low-temperature environment |
| CN112094572A (en) * | 2020-09-18 | 2020-12-18 | 重庆艾普防腐技术有限公司 | Novel water-based epoxy coating for ship engine shell and preparation method thereof |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20100217 |