GB915638A - Substituted o-aminophenols and their use in rubber technology - Google Patents
Substituted o-aminophenols and their use in rubber technologyInfo
- Publication number
- GB915638A GB915638A GB1339360A GB1339360A GB915638A GB 915638 A GB915638 A GB 915638A GB 1339360 A GB1339360 A GB 1339360A GB 1339360 A GB1339360 A GB 1339360A GB 915638 A GB915638 A GB 915638A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tert
- hydrocarbon group
- butyl
- bis
- methylene
- 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
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 title abstract 9
- 150000002430 hydrocarbons Chemical group 0.000 abstract 12
- -1 2-ethylamino- Chemical class 0.000 abstract 11
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 238000002360 preparation method Methods 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 229920003051 synthetic elastomer Polymers 0.000 abstract 3
- 239000005061 synthetic rubber Substances 0.000 abstract 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 abstract 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 238000005336 cracking Methods 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229920003052 natural elastomer Polymers 0.000 abstract 2
- 229920001194 natural rubber Polymers 0.000 abstract 2
- PCAXITAPTVOLGL-UHFFFAOYSA-N 2,3-diaminophenol Chemical class NC1=CC=CC(O)=C1N PCAXITAPTVOLGL-UHFFFAOYSA-N 0.000 abstract 1
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 abstract 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- CJSBUWDGPXGFGA-UHFFFAOYSA-N dimethyl-butadiene Natural products CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/82—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of another six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
-
- 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
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Natural and synthetic rubbers vulcanizates are rendered less susceptible to cracking by adding to mixture to be vulcanized 0,4 to 6% by weight of a substituted o-aminophenol of the general formula <FORM:0915638/IV(a)/1> wherein R1 is a hydrogen atom or a hydrocarbon group containing up to 16 carbon atoms, R2 is a hydrocarbon group containing up to 16 carbon atoms, and R3 and R4 represent a tertiary C4 to C9 hydrocarbon group, or by adding 0,4 to 6% by weight of a bisaminophenol having the structure obtained by substituting the radical <FORM:0915638/IV(a)/2> (wherein R8 and R6 are tertiary C4 to C9 hydrocarbon groups, and R5, R6 and R7 each represent a hydrogen atom or a hydrocarbon group containing up to 16 carbon atoms) in place of R2 in the first formula. All the examples relate to the resistance to cracking, under stretching, in the presence of ozonized air, of vulcanizates of pale crepe to which had been added specific substituted o-aminophenols or bis-aminophenols and various other additives. The specified aminophenols used in these tests were 2-methylamino-4,6-di-tert.-butyl phenol, and the corresponding 2-ethylamino-, n-propylamino-, 2-sec. butylamino-, 2-n-dodecylamino-, 2-phenylamino-, and 2-cyclohexylamino-compounds, also N-methyl-2-hydroxy-41-methyl-3,5-di -tert.-butyl-diphenylamine, N,N1-methylene-bis-(2-n-propylamino-4,6-di-tert.-butyl phenol) and the corresponding 2-tert.-butylaminocompound, N,N1-C-methyl-methylene-bis-(2-cyclohexylamino-4, 6-di-tert.-butyl phenol), N,N-C-isopropyl - methylene - bis - (2 - methylamino - 4,6-di-tert.-butyl phenol) and N,N1-methylene-bis[2-ethylamino - 4,6 - di - (alpha - methylcyclohexyl)-phenol]. Examples of synthetic rubbers which may be stabilized against the action of ozone by these compounds are polymers obtained from butadiene, dimethyl butadiene, and isoprene, and copolymers of such conjugated diolefines with styrene, alpha-methylstyrene, acrylonitrile, methacrylonitrile, acrylates or methacrylates, copolymers of isobutylene with small quantities of conjugated diolefines.ALSO:Substituted o-aminophenols of the general formula <FORM:0915638/IV (b)/1> wherein R1 is a hydrogen atom or a hydrocarbon group containing up to 16 carbon atoms, R2 is a hydrocarbon group containing up to 16 carbon atoms, and R3 and R4 each represent a tertiary C4 to C9 hydrocarbon group, are produced by reacting a 1,2-dihydroxybenzene, substituted in the 4-, 6-positions by the appropriate tertiary hydrocarbon groups, with a primary amine in the presence of oxygen, followed if necessary (i.e. when R1 is to be a hydrocarbon group) by alkylation. Bisaminophenols having the structure obtained by substituting the radical <FORM:0915638/IV (b)/2> (wherein R8 and R9 are tertiary C4 to C9 hydrocarbon groups, and R5, R6 and R7 each represent a hydrogen atom or a hydrocarbon group) in place of R2 in the first formula (R1 = H), are prepared by reacting the appropriate o-aminophenol (prepared as above) with an aliphatic aldehyde. In Example 1, isobutylamine is added to a suspension of 4,6-di-tert.-butylpyrocatechol in light benzene, and the mixture is then stirred for 7 hours in an open vessel. After drying with sodium sulphate, and removing the solvent in vacuo, there is obtained 2-sec.-butylamino-4,6-di-tert.-butylphenol, which may be converted into its hydrochloride. Example 3 describes the preparation of the corresponding (a) ethylamino- (b) n-propylamino- and (c) cyclohexylamino-compounds; and Example 4 describes the preparation of the corresponding dodecylamino-and phenylamino-compounds. When the reaction is effected with a primary arylamine, it is advantageous to work in the presence of a secondary or tertiary amine or an alkali metal hydroxide. Example 4 also describes the preparation of N-methyl-2-hydroxy-41-methyl-3,5-di-tert.-butyl diphenylamine by the action of dimethyl sulphate on 4,6-di-tert.-butyl-2-(N-p-tolyl)-aminophenol. Example 5 describes the preparation of N,N1-methylene-bis-(2-tert.-butylamino-4,6 - di-tert.-butyl-2-(N-tert.-butyl)-aminophenol with formaldehyde. It is stated that N,N1 - C - methyl-methylene-bis-(2-cyclohexylamino-4,6-di-tert.-butyl phenol) may be prepared, in an analogous manner, using acetaldehyde. These substituted o-aminophenols have use as anti-ozonants for natural and synthetic rubber (Group IV(a)). A list of suitable compounds is given; this list includes 2-(p-methoxyphenylamino)-4,6-di-tert.-butyl phenol and the corresponding ethoxyphenylamino-, phenoxy-phenylamino-, chlorophenylamino-, gamma-dimethyl-alpha-amino-, propylamino-, beta-hydroxyethylamino-, pyrenylamino-, and naphthylamino-compounds.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28212A DE1104522B (en) | 1959-04-15 | 1959-04-15 | Process for the preparation of o-aminophenols |
| DEF29491A DE1119297B (en) | 1959-09-29 | 1959-09-29 | Process for the preparation of o-aminophenols |
| DEF29896A DE1133883B (en) | 1959-11-21 | 1959-11-21 | Non-discoloring anti-ozone agents for rubber goods |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB915638A true GB915638A (en) | 1963-01-16 |
Family
ID=27210105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1339360A Expired GB915638A (en) | 1959-04-15 | 1960-04-14 | Substituted o-aminophenols and their use in rubber technology |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1254322A (en) |
| GB (1) | GB915638A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5889125A (en) * | 1996-08-14 | 1999-03-30 | Vianova Resins Gmbh | Curing component for epoxy resins and the use thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2998196A1 (en) | 2012-11-22 | 2014-05-23 | Valeo Sys Controle Moteur Sas | METHOD FOR REGENERATING ZEOLITE |
-
1960
- 1960-04-14 GB GB1339360A patent/GB915638A/en not_active Expired
- 1960-04-15 FR FR824552A patent/FR1254322A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5889125A (en) * | 1996-08-14 | 1999-03-30 | Vianova Resins Gmbh | Curing component for epoxy resins and the use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1254322A (en) | 1961-02-17 |
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