DE1942877C3 - Ozonschutzmittel für Kautschuk - Google Patents
Ozonschutzmittel für KautschukInfo
- Publication number
- DE1942877C3 DE1942877C3 DE1942877A DE1942877A DE1942877C3 DE 1942877 C3 DE1942877 C3 DE 1942877C3 DE 1942877 A DE1942877 A DE 1942877A DE 1942877 A DE1942877 A DE 1942877A DE 1942877 C3 DE1942877 C3 DE 1942877C3
- Authority
- DE
- Germany
- Prior art keywords
- xylylenediamine
- rubber
- ozone
- agents
- radicals
- 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.)
- Expired
Links
- 229920001971 elastomer Polymers 0.000 title description 36
- 239000005060 rubber Substances 0.000 title description 35
- 239000003795 chemical substances by application Substances 0.000 title description 24
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 60
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 24
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 17
- -1 dialkylamino radical Chemical class 0.000 description 16
- 238000002845 discoloration Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- GKXVJHDEWHKBFH-UHFFFAOYSA-N xylylenediamine group Chemical class C=1(C(=CC=CC1)CN)CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 7
- 238000010186 staining Methods 0.000 description 6
- 229920003051 synthetic elastomer Polymers 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920003052 natural elastomer Polymers 0.000 description 4
- 229920001194 natural rubber Polymers 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000005061 synthetic rubber Substances 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- OVRQXQSDQWOJIL-UHFFFAOYSA-N 1,1-dibutylthiourea Chemical compound CCCCN(C(N)=S)CCCC OVRQXQSDQWOJIL-UHFFFAOYSA-N 0.000 description 1
- VETPHHXZEJAYOB-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC=CC2=CC(NC=3C=CC(NC=4C=C5C=CC=CC5=CC=4)=CC=3)=CC=C21 VETPHHXZEJAYOB-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- ZPXTVKRWEFNGQI-UHFFFAOYSA-N C(C)OC(=O)CCNCC1=CC(=CC=C1)CNCCC(=O)OCC Chemical compound C(C)OC(=O)CCNCC1=CC(=CC=C1)CNCCC(=O)OCC ZPXTVKRWEFNGQI-UHFFFAOYSA-N 0.000 description 1
- BBASRBJKLSCBBH-UHFFFAOYSA-N C(C1=CC=CC=C1)NCC1=CC=C(C=C1)CNC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)NCC1=CC=C(C=C1)CNC1=CC=CC=C1 BBASRBJKLSCBBH-UHFFFAOYSA-N 0.000 description 1
- DBYVCWCCPHWYML-UHFFFAOYSA-N CC(C)NCC1=CC=C(CNC(C=C2)=CC=C2OC)C=C1 Chemical compound CC(C)NCC1=CC=C(CNC(C=C2)=CC=C2OC)C=C1 DBYVCWCCPHWYML-UHFFFAOYSA-N 0.000 description 1
- QHOAYUJEQIDKFK-UHFFFAOYSA-N CC(C)NCC1=CC=C(CNCC(C=C2)=CC=C2Cl)C=C1 Chemical compound CC(C)NCC1=CC=C(CNCC(C=C2)=CC=C2Cl)C=C1 QHOAYUJEQIDKFK-UHFFFAOYSA-N 0.000 description 1
- LWBDOKKPAVYSSW-UHFFFAOYSA-N CC1=CC(CN(CC2=CC=CC=C2)CC2=CC=CC=C2)=C(C)C=C1CN(CC1=CC=CC=C1)CC1=CC=CC=C1 Chemical compound CC1=CC(CN(CC2=CC=CC=C2)CC2=CC=CC=C2)=C(C)C=C1CN(CC1=CC=CC=C1)CC1=CC=CC=C1 LWBDOKKPAVYSSW-UHFFFAOYSA-N 0.000 description 1
- ALMKUFWCCFRFGR-UHFFFAOYSA-N CC1=CC(CN(CC2=CC=CC=C2)CC2=CC=CC=C2)=C(C)C=C1CNCC1=CC=CC=C1 Chemical compound CC1=CC(CN(CC2=CC=CC=C2)CC2=CC=CC=C2)=C(C)C=C1CNCC1=CC=CC=C1 ALMKUFWCCFRFGR-UHFFFAOYSA-N 0.000 description 1
- ZZNFWMJSQXQSPW-UHFFFAOYSA-N CNC1=CC=C(CNCC2=CC(CNCC(C=C3)=CC=C3NC)=CC=C2)C=C1 Chemical compound CNC1=CC=C(CNCC2=CC(CNCC(C=C3)=CC=C3NC)=CC=C2)C=C1 ZZNFWMJSQXQSPW-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 244000048879 Funtumia elastica Species 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AEQPJVTXUPTKAL-UHFFFAOYSA-N N-(naphthalen-2-ylmethyl)-1-[4-[(naphthalen-2-ylmethylamino)methyl]phenyl]methanamine Chemical compound C(NCc1ccc2ccccc2c1)c1ccc(CNCc2ccc3ccccc3c2)cc1 AEQPJVTXUPTKAL-UHFFFAOYSA-N 0.000 description 1
- CVEJCABOBJVKHR-UHFFFAOYSA-N N-[(4-chlorophenyl)methyl]-1-[4-[[(4-chlorophenyl)methylamino]methyl]phenyl]methanamine Chemical compound ClC1=CC=C(CNCC2=CC=C(C=C2)CNCC2=CC=C(C=C2)Cl)C=C1 CVEJCABOBJVKHR-UHFFFAOYSA-N 0.000 description 1
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical class NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000005647 hydrohalogenation reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000012936 vulcanization activator Substances 0.000 description 1
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
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/925—Natural rubber compositions having nonreactive materials, i.e. NRM, other than: carbon, silicon dioxide, glass titanium dioxide, water, hydrocarbon or halohydrocarbon
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5992568 | 1968-08-23 | ||
| JP262269 | 1969-01-16 | ||
| JP572869 | 1969-01-28 | ||
| JP5376369 | 1969-07-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1942877A1 DE1942877A1 (de) | 1970-04-16 |
| DE1942877B2 DE1942877B2 (de) | 1974-07-04 |
| DE1942877C3 true DE1942877C3 (de) | 1975-03-13 |
Family
ID=27453680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1942877A Expired DE1942877C3 (de) | 1968-08-23 | 1969-08-22 | Ozonschutzmittel für Kautschuk |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3634316A (cg-RX-API-DMAC7.html) |
| DE (1) | DE1942877C3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2016302A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1268419A (cg-RX-API-DMAC7.html) |
| NL (1) | NL137481C (cg-RX-API-DMAC7.html) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1021819C (zh) * | 1988-01-20 | 1993-08-18 | 山之内制药株式会社 | 作为药物有用的双脲衍生物的制备方法 |
| HUP0400494A3 (en) * | 2000-03-24 | 2004-08-30 | Mediquest Therapeutics Inc Sea | Polyamine analogues as cytotoxic agents and pharmaceutical compositions containing them |
| KR100863667B1 (ko) * | 2002-09-11 | 2008-10-15 | 가부시끼가이샤 구레하 | 아민 화합물 및 그 용도 |
| KR101149124B1 (ko) * | 2004-03-10 | 2012-05-25 | 가부시끼가이샤 구레하 | 아민계 염기성 화합물과 그의 용도 |
| EP2546230A1 (de) * | 2011-07-15 | 2013-01-16 | Sika Technology AG | Emissionsarmer Härter für Epoxidharze |
| US8729213B2 (en) | 2011-09-23 | 2014-05-20 | Air Products And Chemicals, Inc. | Benzylated polyamine curing agents |
| GB201208775D0 (en) * | 2012-05-18 | 2012-07-04 | Uni I Oslo | Chemical compounds |
| JP7582553B2 (ja) * | 2022-09-20 | 2024-11-13 | 三菱瓦斯化学株式会社 | アミノ組成物及びその製造方法、エポキシ樹脂硬化剤、エポキシ樹脂組成物並びにその硬化物 |
| CN117567301B (zh) * | 2023-10-07 | 2026-08-04 | 中山大学 | 一种阳离子类脂分子及其用于脂质纳米粒体系的制备 |
-
1969
- 1969-08-18 US US851093A patent/US3634316A/en not_active Expired - Lifetime
- 1969-08-22 DE DE1942877A patent/DE1942877C3/de not_active Expired
- 1969-08-22 FR FR6928927A patent/FR2016302A1/fr not_active Withdrawn
- 1969-08-22 GB GB42048/69A patent/GB1268419A/en not_active Expired
- 1969-08-22 NL NL6912838A patent/NL137481C/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1268419A (en) | 1972-03-29 |
| DE1942877B2 (de) | 1974-07-04 |
| DE1942877A1 (de) | 1970-04-16 |
| NL6912838A (cg-RX-API-DMAC7.html) | 1970-02-25 |
| NL137481C (cg-RX-API-DMAC7.html) | 1973-05-15 |
| US3634316A (en) | 1972-01-11 |
| FR2016302A1 (cg-RX-API-DMAC7.html) | 1970-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |