DE1162552B - Verfahren zur Vulkanisation von Natur- und Synthesekautschuk - Google Patents
Verfahren zur Vulkanisation von Natur- und SynthesekautschukInfo
- Publication number
- DE1162552B DE1162552B DEC17435A DEC0017435A DE1162552B DE 1162552 B DE1162552 B DE 1162552B DE C17435 A DEC17435 A DE C17435A DE C0017435 A DEC0017435 A DE C0017435A DE 1162552 B DE1162552 B DE 1162552B
- Authority
- DE
- Germany
- Prior art keywords
- resin
- vulcanization
- alkylphenol
- mixture
- metal
- 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
- 238000004073 vulcanization Methods 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 7
- 229920003052 natural elastomer Polymers 0.000 title claims description 6
- 229920001194 natural rubber Polymers 0.000 title claims description 6
- 229920003051 synthetic elastomer Polymers 0.000 title claims description 5
- 239000005061 synthetic rubber Substances 0.000 title claims description 5
- 239000011347 resin Substances 0.000 claims description 49
- 229920005989 resin Polymers 0.000 claims description 49
- 229910001507 metal halide Inorganic materials 0.000 claims description 12
- 150000005309 metal halides Chemical class 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 41
- 229920001971 elastomer Polymers 0.000 description 14
- 239000006229 carbon black Substances 0.000 description 12
- 229920005549 butyl rubber Polymers 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 235000021355 Stearic acid Nutrition 0.000 description 9
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 9
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 9
- 239000005060 rubber Substances 0.000 description 9
- 239000008117 stearic acid Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229910001510 metal chloride Inorganic materials 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LZDOYVMSNJBLIM-UHFFFAOYSA-N 4-tert-butylphenol;formaldehyde Chemical compound O=C.CC(C)(C)C1=CC=C(O)C=C1 LZDOYVMSNJBLIM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
- SIBBGGADHQDMHI-UHFFFAOYSA-N 4-tert-butyl-2,6-bis(hydroxymethyl)phenol Chemical compound CC(C)(C)C1=CC(CO)=C(O)C(CO)=C1 SIBBGGADHQDMHI-UHFFFAOYSA-N 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229920001079 Thiokol (polymer) Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- -1 benzene hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
- 229910001509 metal bromide Inorganic materials 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical group O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL239977D NL239977A (en(2012)) | 1958-09-03 | ||
| DEC17435A DE1162552B (de) | 1958-09-03 | 1958-09-03 | Verfahren zur Vulkanisation von Natur- und Synthesekautschuk |
| FR802994A FR1238482A (fr) | 1958-09-03 | 1959-08-18 | Procédé de vulcanisation de caoutchouc naturel ou artificiel au moyen de résines alkylphénols renforcées |
| BE581803A BE581803A (fr) | 1958-09-03 | 1959-08-19 | Procédé pour la vulcanisation du caoutchouc naturel et synthétique par des résines alcoylphénolées "renforcées". |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC17435A DE1162552B (de) | 1958-09-03 | 1958-09-03 | Verfahren zur Vulkanisation von Natur- und Synthesekautschuk |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1162552B true DE1162552B (de) | 1964-02-06 |
Family
ID=7016249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC17435A Pending DE1162552B (de) | 1958-09-03 | 1958-09-03 | Verfahren zur Vulkanisation von Natur- und Synthesekautschuk |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE581803A (en(2012)) |
| DE (1) | DE1162552B (en(2012)) |
| FR (1) | FR1238482A (en(2012)) |
| NL (1) | NL239977A (en(2012)) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE935283C (de) * | 1952-02-07 | 1955-11-17 | Us Rubber Co | Verfahren zum Vulkanisieren von Butylkautschuk |
| US2726224A (en) * | 1953-01-02 | 1955-12-06 | Us Rubber Co | Acceleration of the reaction between butyl rubber and dimethylol phenols by means of heavy metal halides, and product obtained thereby |
| US2794009A (en) * | 1953-10-12 | 1957-05-28 | Us Rubber Co | Use of organic sulfonic acids to accelerate the vulcanization of butyl rubber with dimethylol phenols |
| US2825720A (en) * | 1955-09-27 | 1958-03-04 | Us Rubber Co | Vulcanization of butyl rubber by 2, 6-di(acyloxymethyl)-4-hydrocarbylphenyl acylates |
| US2829123A (en) * | 1955-09-27 | 1958-04-01 | Us Rubber Co | Vulcanization of butyl rubber by 2, 6-di-(alkoxymethyl)-4-hydrocarbyl phenols |
| US2829132A (en) * | 1955-09-27 | 1958-04-01 | Us Rubber Co | Vulcanization of butyl rubber by 2, 4, 6-tris(acyloxymethyl) phenyl alkanoate |
| US2830970A (en) * | 1955-09-27 | 1958-04-15 | Us Rubber Co | Vulcanization of butyl rubber by 2,6-di(acyloxymethyl)-4-hydrocarbyl phenols |
-
0
- NL NL239977D patent/NL239977A/xx unknown
-
1958
- 1958-09-03 DE DEC17435A patent/DE1162552B/de active Pending
-
1959
- 1959-08-18 FR FR802994A patent/FR1238482A/fr not_active Expired
- 1959-08-19 BE BE581803A patent/BE581803A/fr unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE935283C (de) * | 1952-02-07 | 1955-11-17 | Us Rubber Co | Verfahren zum Vulkanisieren von Butylkautschuk |
| US2726224A (en) * | 1953-01-02 | 1955-12-06 | Us Rubber Co | Acceleration of the reaction between butyl rubber and dimethylol phenols by means of heavy metal halides, and product obtained thereby |
| US2794009A (en) * | 1953-10-12 | 1957-05-28 | Us Rubber Co | Use of organic sulfonic acids to accelerate the vulcanization of butyl rubber with dimethylol phenols |
| US2825720A (en) * | 1955-09-27 | 1958-03-04 | Us Rubber Co | Vulcanization of butyl rubber by 2, 6-di(acyloxymethyl)-4-hydrocarbylphenyl acylates |
| US2829123A (en) * | 1955-09-27 | 1958-04-01 | Us Rubber Co | Vulcanization of butyl rubber by 2, 6-di-(alkoxymethyl)-4-hydrocarbyl phenols |
| US2829132A (en) * | 1955-09-27 | 1958-04-01 | Us Rubber Co | Vulcanization of butyl rubber by 2, 4, 6-tris(acyloxymethyl) phenyl alkanoate |
| US2830970A (en) * | 1955-09-27 | 1958-04-15 | Us Rubber Co | Vulcanization of butyl rubber by 2,6-di(acyloxymethyl)-4-hydrocarbyl phenols |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1238482A (fr) | 1960-08-12 |
| NL239977A (en(2012)) | |
| BE581803A (fr) | 1960-12-16 |
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