CN113444286A - Addition type liquid fluorosilicone rubber inhibitor and preparation method thereof - Google Patents
Addition type liquid fluorosilicone rubber inhibitor and preparation method thereof Download PDFInfo
- Publication number
- CN113444286A CN113444286A CN202110928159.XA CN202110928159A CN113444286A CN 113444286 A CN113444286 A CN 113444286A CN 202110928159 A CN202110928159 A CN 202110928159A CN 113444286 A CN113444286 A CN 113444286A
- Authority
- CN
- China
- Prior art keywords
- fluorosilicone rubber
- type liquid
- addition type
- reaction
- liquid fluorosilicone
- 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.)
- Granted
Links
- 229920005560 fluorosilicone rubber Polymers 0.000 title claims abstract description 79
- 239000003112 inhibitor Substances 0.000 title claims abstract description 66
- 239000007788 liquid Substances 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 238000003756 stirring Methods 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 20
- 239000000706 filtrate Substances 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 claims description 16
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 claims description 15
- 238000001816 cooling Methods 0.000 claims description 15
- 230000003472 neutralizing effect Effects 0.000 claims description 13
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 10
- 229960001545 hydrotalcite Drugs 0.000 claims description 10
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- URZHQOCYXDNFGN-UHFFFAOYSA-N 2,4,6-trimethyl-2,4,6-tris(3,3,3-trifluoropropyl)-1,3,5,2,4,6-trioxatrisilinane Chemical compound FC(F)(F)CC[Si]1(C)O[Si](C)(CCC(F)(F)F)O[Si](C)(CCC(F)(F)F)O1 URZHQOCYXDNFGN-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 238000006386 neutralization reaction Methods 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 8
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 7
- 230000001681 protective effect Effects 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 239000011968 lewis acid catalyst Substances 0.000 claims description 5
- 150000007517 lewis acids Chemical class 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 16
- 230000000694 effects Effects 0.000 abstract description 13
- 238000003860 storage Methods 0.000 abstract description 6
- 230000005764 inhibitory process Effects 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 3
- 239000000654 additive Substances 0.000 abstract 3
- 230000000996 additive effect Effects 0.000 abstract 3
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 13
- 229920001971 elastomer Polymers 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- JQZGUQIEPRIDMR-UHFFFAOYSA-N 3-methylbut-1-yn-1-ol Chemical compound CC(C)C#CO JQZGUQIEPRIDMR-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 6
- 230000001105 regulatory effect Effects 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- 230000009471 action Effects 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- -1 polyfluorosiloxane Polymers 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- 229910020038 Mg6Al2 Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000004754 hydrosilicons Chemical class 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002683 reaction inhibitor Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
Images
Classifications
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
Description
Vinyl fluorosilicone oil (viscosity 30000cp, vinyl mass fraction 0.20%) | 100 portions of |
Hydrophobic fumed silica (220 +/-25 m)2/g) | 25 portions of |
Hydrogen-containing fluorosilicone oil (viscosity 80cp, hydrogen mass fraction 0.48%) | 2.2 parts of |
Platinum catalyst (platinum content 3000ppm) | 0.5 portion |
Viscosity of the solution | Example 1 | Example 3 | Methyl butynol | Ethynyl cyclohexanol |
initial/Pa.s | 780 | 775 | 778 | 783 |
4h/Pa.s | 788 | 779 | 1670 | 989 |
8h/Pa.s | 795 | 784 | Gelation | 1356 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110928159.XA CN113444286B (en) | 2021-08-13 | 2021-08-13 | Addition type liquid fluorosilicone rubber inhibitor and preparation method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110928159.XA CN113444286B (en) | 2021-08-13 | 2021-08-13 | Addition type liquid fluorosilicone rubber inhibitor and preparation method thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113444286A true CN113444286A (en) | 2021-09-28 |
CN113444286B CN113444286B (en) | 2022-05-27 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN202110928159.XA Active CN113444286B (en) | 2021-08-13 | 2021-08-13 | Addition type liquid fluorosilicone rubber inhibitor and preparation method thereof |
Country Status (1)
Country | Link |
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CN (1) | CN113444286B (en) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0523305B2 (en) * | 1987-08-21 | 1993-04-02 | Shinetsu Chem Ind Co | |
CN105418669A (en) * | 2015-12-07 | 2016-03-23 | 武汉大学 | Alkoxy silane acetylenic silicon hydrogen addition inhibitor and preparation method thereof |
CN110256853A (en) * | 2019-05-10 | 2019-09-20 | 肇庆皓明有机硅材料有限公司 | A kind of in-place molding foamed silastic sealing ring composition and preparation method thereof |
CN111925526A (en) * | 2020-08-31 | 2020-11-13 | 威海新元新材料有限公司 | High-activity hydrogen-containing fluorosilicone oil cross-linking agent and preparation method thereof |
US20210300003A1 (en) * | 2018-07-25 | 2021-09-30 | Dow Toray Co., Ltd. | Production method for laminate of fluorosilicone rubber and silicone rubber |
-
2021
- 2021-08-13 CN CN202110928159.XA patent/CN113444286B/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0523305B2 (en) * | 1987-08-21 | 1993-04-02 | Shinetsu Chem Ind Co | |
CN105418669A (en) * | 2015-12-07 | 2016-03-23 | 武汉大学 | Alkoxy silane acetylenic silicon hydrogen addition inhibitor and preparation method thereof |
US20210300003A1 (en) * | 2018-07-25 | 2021-09-30 | Dow Toray Co., Ltd. | Production method for laminate of fluorosilicone rubber and silicone rubber |
CN110256853A (en) * | 2019-05-10 | 2019-09-20 | 肇庆皓明有机硅材料有限公司 | A kind of in-place molding foamed silastic sealing ring composition and preparation method thereof |
CN111925526A (en) * | 2020-08-31 | 2020-11-13 | 威海新元新材料有限公司 | High-activity hydrogen-containing fluorosilicone oil cross-linking agent and preparation method thereof |
Also Published As
Publication number | Publication date |
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CN113444286B (en) | 2022-05-27 |
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Address after: 264204 no.985 Fenghuangshan Road, Yangting industrial new area, Huancui District, Weihai City, Shandong Province Applicant after: Xinyuan chemical (Shandong) Co.,Ltd. Applicant after: Weihai Xinyuan New Material Co.,Ltd. Address before: 264204 no.985 Fenghuangshan Road, Yangting industrial new area, Huancui District, Weihai City, Shandong Province Applicant before: WEIHAI NEWERA CHEMICAL Co.,Ltd. Applicant before: Weihai Xinyuan New Material Co.,Ltd. |
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Denomination of invention: A kind of addition type liquid fluorosilicone rubber inhibitor and preparation method thereof Effective date of registration: 20220921 Granted publication date: 20220527 Pledgee: Weihai City Commercial Bank Limited by Share Ltd. high tech branch Pledgor: Xinyuan chemical (Shandong) Co.,Ltd.|Weihai Xinyuan New Material Co.,Ltd. Registration number: Y2022980015764 |
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