CA1107053A - Antioxydant pour caoutchouc - Google Patents

Antioxydant pour caoutchouc

Info

Publication number: CA1107053A
Authority: CA; Canada
Prior art keywords: rubber; weight; antioxidant; parts; trimethyl
Prior art date: 1977-07-22
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

Application number

CA307,860A

Other languages

English (en)

Inventor

Tadashi Watanabe

Susumu Sato

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bridgestone Corp

Original Assignee

Bridgestone Corp

Priority date (The priority date 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 date listed.)

1977-07-22

Filing date

1978-07-21

Publication date

1981-08-18

1978-07-21 Application filed by Bridgestone Corp filed Critical Bridgestone Corp

1981-08-18 Application granted granted Critical

1981-08-18 Publication of CA1107053A publication Critical patent/CA1107053A/fr

Status Expired legal-status Critical Current

Links

229920001971 elastomer Polymers 0.000 title claims abstract description 62
239000005060 rubber Substances 0.000 title claims abstract description 62
239000003963 antioxidant agent Substances 0.000 title claims abstract description 38
230000003078 antioxidant effect Effects 0.000 title claims abstract description 35
ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 claims abstract description 25
229920003052 natural elastomer Polymers 0.000 claims abstract description 24
229920001194 natural rubber Polymers 0.000 claims abstract description 24
229920000642 polymer Polymers 0.000 claims abstract description 18
150000001412 amines Chemical class 0.000 claims abstract description 11
239000012535 impurity Substances 0.000 claims abstract description 10
239000000539 dimer Substances 0.000 claims abstract description 8
244000043261 Hevea brasiliensis Species 0.000 claims description 20
239000002174 Styrene-butadiene Substances 0.000 claims description 5
239000013638 trimer Substances 0.000 claims description 4
239000005062 Polybutadiene Substances 0.000 claims description 2
229920002857 polybutadiene Polymers 0.000 claims description 2
229920001195 polyisoprene Polymers 0.000 claims description 2
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims 1
229920003244 diene elastomer Polymers 0.000 claims 1
239000011115 styrene butadiene Substances 0.000 claims 1
230000006866 deterioration Effects 0.000 abstract description 12
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract description 8
230000003064 anti-oxidating effect Effects 0.000 abstract description 5
230000000694 effects Effects 0.000 abstract description 5
238000010186 staining Methods 0.000 abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 4
238000004040 coloring Methods 0.000 abstract description 4
229910052760 oxygen Inorganic materials 0.000 abstract description 4
239000001301 oxygen Substances 0.000 abstract description 4
229920003051 synthetic elastomer Polymers 0.000 abstract description 4
239000005061 synthetic rubber Substances 0.000 abstract description 4
230000003405 preventing effect Effects 0.000 abstract description 2
235000006708 antioxidants Nutrition 0.000 description 29
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
229920003048 styrene butadiene rubber Polymers 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241000894007 species Species 0.000 description 4
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
230000032683 aging Effects 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000006229 carbon black Substances 0.000 description 2
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
238000002156 mixing Methods 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
230000000704 physical effect Effects 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
239000004636 vulcanized rubber Substances 0.000 description 2
239000011787 zinc oxide Substances 0.000 description 2
235000014692 zinc oxide Nutrition 0.000 description 2
IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 1
ZUXNHFFVQWADJL-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(2-methoxyethyl)-n-(4-phenyl-1,3-thiazol-2-yl)benzamide Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1N(CCOC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 ZUXNHFFVQWADJL-UHFFFAOYSA-N 0.000 description 1
BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
239000006237 Intermediate SAF Substances 0.000 description 1
241000063973 Mattia Species 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
238000007664 blowing Methods 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000009826 distribution Methods 0.000 description 1
WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000001879 gelation Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
-1 iodine, hydrogen Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000018984 mastication Effects 0.000 description 1
238000010077 mastication Methods 0.000 description 1
238000000034 method Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
230000002794 monomerizing effect Effects 0.000 description 1
DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
HKQBGDOVZRQTMC-UHFFFAOYSA-N n-phenyl-4-propan-2-ylaniline Chemical compound C1=CC(C(C)C)=CC=C1NC1=CC=CC=C1 HKQBGDOVZRQTMC-UHFFFAOYSA-N 0.000 description 1
LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000004445 quantitative analysis Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
235000013799 ultramarine blue Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
- 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
- C08K5/34—Heterocyclic compounds having nitrogen in the 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
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3437—Six-membered rings condensed with carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Compositions Of Macromolecular Compounds (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

CA307,860A 1977-07-22 1978-07-21 Antioxydant pour caoutchouc Expired CA1107053A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP87443/77		1977-07-22
JP8744377A JPS5423650A (en)	1977-07-22	1977-07-22	Antiaging agent for rubber

Publications (1)

Publication Number	Publication Date
CA1107053A true CA1107053A (fr)	1981-08-18

Family

ID=13914991

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA307,860A Expired CA1107053A (fr)	1977-07-22	1978-07-21	Antioxydant pour caoutchouc

Country Status (6)

Country	Link
JP (1)	JPS5423650A (fr)
AU (1)	AU519398B2 (fr)
CA (1)	CA1107053A (fr)
DE (1)	DE2832126C3 (fr)
FR (1)	FR2398088A1 (fr)
GB (1)	GB2002783B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103261166A (zh) *	2010-10-18	2013-08-21	住友化学株式会社	含有2，2，4-三甲基-1，2-二氢喹啉聚合物的组合物的制造方法

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5620026A (en) *	1979-07-26	1981-02-25	Sumitomo Chem Co Ltd	Production of 2,2,4-trimethyl-1,2-dihydroquinoline polymer
EP0147378B1 (fr) *	1983-12-23	1987-05-06	Monsanto Company	Agents antioxydants liquides du type hydroquinoléine
EP0497735A1 (fr) *	1991-01-31	1992-08-05	Ciba-Geigy Ag	Composés d'hydroquinoléine
CA2113743C (fr)	1993-02-03	2005-06-28	Naoki Inui	Objet en caoutchouc renforce, sa fabrication, et melange de caoutchouc convenable a cet effet
JP2012197417A (ja) *	2010-10-18	2012-10-18	Sumitomo Chemical Co Ltd	２，２，４−トリメチル−１，２−ジヒドロキノリン重合物含有組成物の製造方法
DE102021213720A1 (de) *	2021-12-02	2023-06-07	Continental Reifen Deutschland Gmbh	Verbindung, Kautschukmischung enthaltend die Verbindung, Fahrzeugreifen, der die Kautschukmischung in wenigstens einem Bauteil aufweist, Verfahren zur Herstellung der Verbindung sowie Verwendung der Verbindung als Alterungsschutzmittel und/oder Antioxidationsmittel

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3244683A (en) *	1963-01-17	1966-04-05	Goodyear Tire & Rubber	Polymerization of 2, 2, 4-trimethyl-1, 2-dihydroquinoline
JPS53145854A (en) *	1977-05-25	1978-12-19	Sumitomo Chem Co Ltd	Deterioration of inhibitor for rubber
JP2954099B2 (ja) *	1997-06-26	1999-09-27	東北日本電気株式会社	溶接痕外観検査方法

1977
- 1977-07-22 JP JP8744377A patent/JPS5423650A/ja active Granted
1978
- 1978-07-17 AU AU38075/78A patent/AU519398B2/en not_active Expired
- 1978-07-20 GB GB7830486A patent/GB2002783B/en not_active Expired
- 1978-07-21 DE DE2832126A patent/DE2832126C3/de not_active Expired
- 1978-07-21 FR FR7821659A patent/FR2398088A1/fr active Granted
- 1978-07-21 CA CA307,860A patent/CA1107053A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103261166A (zh) *	2010-10-18	2013-08-21	住友化学株式会社	含有2，2，4-三甲基-1，2-二氢喹啉聚合物的组合物的制造方法

Also Published As

Publication number	Publication date
JPS5512455B2 (fr)	1980-04-02
AU3807578A (en)	1980-01-17
DE2832126C3 (de)	1982-05-13
DE2832126B2 (de)	1981-08-13
AU519398B2 (en)	1981-12-03
GB2002783A (en)	1979-02-28
DE2832126A1 (de)	1979-02-08
GB2002783B (en)	1982-02-24
FR2398088B1 (fr)	1984-11-02
JPS5423650A (en)	1979-02-22
FR2398088A1 (fr)	1979-02-16

Legal Events

Date	Code	Title	Description
1998-08-18	MKEX	Expiry

Publication	Publication Date	Title
JP7334276B2 (ja)	2023-08-28	低汚染の劣化防止剤化合物、劣化防止剤組成物およびそれを含むタイヤ用ゴム組成物
CA2350216C (fr)	2008-09-02	Resines thermoplastiques stabilisees par des melanges de phenols, d'amines secondaires et de thioethers steriquement entraves
DE2164800C3 (de)	1978-06-22	p-Aminophenylamino-s-triazin-Verbindungen und deren Verwendung
CA1107053A (fr)	1981-08-18	Antioxydant pour caoutchouc
DE3888760T2 (de)	1994-07-28	Arylendiaminosubstituiertes Triazin.
CA2113743C (fr)	2005-06-28	Objet en caoutchouc renforce, sa fabrication, et melange de caoutchouc convenable a cet effet
EP0309283B1 (fr)	1994-01-26	Polyéthylène stabilisé à l'aide d'un mélange d'un phénol encombré et d'un antioxydant aminé
US5120779A (en)	1992-06-09	Tire sidewall
US3000852A (en)	1961-09-19	N-(alkyl)-n'-(p-alkyl phenyl)-p-phenylenediamines as stabilizers for rubbers
US5047530A (en)	1991-09-10	Arylenediamine substituted triazines
US5118807A (en)	1992-06-02	N-alkyl-p-quinonediimino triazine compounds
US5208280A (en)	1993-05-04	Elastomers and tire with N-alkyl-p-quinonediimino triazine stabilizers
CA1069635A (fr)	1980-01-08	Enamines anti-ozonation, ne tachant pas
US4301296A (en)	1981-11-17	Antioxidant combination of esters and amines
KR20020042232A (ko)	2002-06-05	인너라이너 고무조성물
US2203899A (en)	1940-06-11	Rubber composition and method of preserving rubber
US4241217A (en)	1980-12-23	Antioxidant combination of esters and amines
JP3275419B2 (ja)	2002-04-15	ゴム組成物およびそれを用いるスチールコードとの接着方法
US3274250A (en)	1966-09-20	N-phenyl-n'-(1, 2-dimethylpropyl)-p-phenylenediamines
CA1140552A (fr)	1983-02-01	Poly(6-oxy-2,2,4-trialkyl-1,2-dihydroquinoline) alkylenes utilises comme agents antidegradants pour le caoutchouc
DE4033902A1 (de)	1992-04-30	Verwendung von n-trichlormethylsulfenylbenzolsulfanilid zur verminderung der nitrosaminbildung bei der schwefelvulkanisation
US3978021A (en)	1976-08-31	Inhibiting ozone deterioration of rubbers
US3644284A (en)	1972-02-22	Elastomeric composition containing polyester stabilizers
US3562210A (en)	1971-02-09	Elastomeric composition containing phosphite ester and polyester stabilizers
US2729614A (en)	1956-01-03	Stabilization of oxygen-sensitive materials with substituted guanylguanidines

CA1107053A - Antioxydant pour caoutchouc - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=13914991

Family Applications (1)

Country Status (6)

Cited By (1)

Families Citing this family (6)

Family Cites Families (3)

Cited By (1)

Also Published As

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Legal Events