DE2540432C2 - Schwefelhaltige Alkyliden-bisphenole, deren Herstellung und Verwendung als Stabilisatoren - Google Patents

Schwefelhaltige Alkyliden-bisphenole, deren Herstellung und Verwendung als Stabilisatoren

Info

Publication number: DE2540432C2
Authority: DE; Germany
Prior art keywords: compounds; formula; bis; butane; stabilizers
Prior art date: 1974-09-16
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

DE2540432A

Other languages

German (de)

English (en)

Other versions

DE2540432A1 (de

Inventor

Siegfried Dipl.-Chem. Riehen Rosenberger

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.)

Novartis AG

Original Assignee

Ciba Geigy AG

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.)

1974-09-16

Filing date

1975-09-11

Publication date

1986-07-03

1975-09-11 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1976-04-01 Publication of DE2540432A1 publication Critical patent/DE2540432A1/de

1986-07-03 Application granted granted Critical

1986-07-03 Publication of DE2540432C2 publication Critical patent/DE2540432C2/de

Status Expired legal-status Critical Current

Links

239000003381 stabilizer Substances 0.000 title description 15
-1 alkylidene bisphenols Chemical class 0.000 title description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 2
229910052717 sulfur Inorganic materials 0.000 title description 2
239000011593 sulfur Substances 0.000 title description 2
229930185605 Bisphenol Natural products 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 7
238000000034 method Methods 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
229920001971 elastomer Polymers 0.000 description 8
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000000806 elastomer Substances 0.000 description 5
229920002857 polybutadiene Polymers 0.000 description 5
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
LXFQGMRHWHCOKG-UHFFFAOYSA-N 2-[3-dodecylsulfanyl-1-(2-hydroxy-3,5-dimethylphenyl)butyl]-4,6-dimethylphenol Chemical compound C=1C(C)=CC(C)=C(O)C=1C(CC(C)SCCCCCCCCCCCC)C1=CC(C)=CC(C)=C1O LXFQGMRHWHCOKG-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000005062 Polybutadiene Substances 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000005060 rubber Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 2
MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
229920013623 Solprene Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
ZYPDAQYUHJXYKX-UHFFFAOYSA-N 4-tert-butyl-2-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=CC=C1O ZYPDAQYUHJXYKX-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
241001441571 Hiodontidae Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000007863 gel particle Substances 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004898 kneading Methods 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000000725 suspension Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic 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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DE2540432A 1974-09-16 1975-09-11 Schwefelhaltige Alkyliden-bisphenole, deren Herstellung und Verwendung als Stabilisatoren Expired DE2540432C2 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1257374		1974-09-16

Publications (2)

Publication Number	Publication Date
DE2540432A1 DE2540432A1 (de)	1976-04-01
DE2540432C2 true DE2540432C2 (de)	1986-07-03

Family

ID=4384289

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE2540432A Expired DE2540432C2 (de)	1974-09-16	1975-09-11	Schwefelhaltige Alkyliden-bisphenole, deren Herstellung und Verwendung als Stabilisatoren

Country Status (10)

Country	Link
JP (2)	JPS5946262B2 (fr)
AU (1)	AU8479575A (fr)
BE (1)	BE833406A (fr)
BR (1)	BR7505912A (fr)
CA (1)	CA1072122A (fr)
DE (1)	DE2540432C2 (fr)
ES (1)	ES440962A1 (fr)
FR (1)	FR2284593A1 (fr)
GB (1)	GB1457089A (fr)
NL (1)	NL7510346A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4721814A (en) *	1986-01-23	1988-01-26	Ciba-Geigy Corporation	Mercaptan-containing polyphenols
JPH0434316A (ja) *	1990-05-30	1992-02-05	Osaka Gas Co Ltd	流量計
EP3533786A1 (fr)	2018-03-02	2019-09-04	Givaudan SA	Précurseurs thioéther de cétones et d'aldéhydes parfumants
GB201803410D0 (en) *	2018-03-02	2018-04-18	Givaudan Sa	Improvements in or relating to organic compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3699152A (en) *	1969-12-10	1972-10-17	Carlisle Chemical Works	Sulfur containing esters of substituted hydroxyphenyl-alkanoic acids

1975
- 1975-09-02 NL NL7510346A patent/NL7510346A/xx not_active Application Discontinuation
- 1975-09-11 DE DE2540432A patent/DE2540432C2/de not_active Expired
- 1975-09-12 AU AU84795/75A patent/AU8479575A/en not_active Expired
- 1975-09-12 CA CA235,337A patent/CA1072122A/fr not_active Expired
- 1975-09-15 ES ES75440962A patent/ES440962A1/es not_active Expired
- 1975-09-15 GB GB3777475A patent/GB1457089A/en not_active Expired
- 1975-09-15 BR BR7505912*A patent/BR7505912A/pt unknown
- 1975-09-15 BE BE160031A patent/BE833406A/fr not_active IP Right Cessation
- 1975-09-15 FR FR7528185A patent/FR2284593A1/fr active Granted
- 1975-09-16 JP JP50112032A patent/JPS5946262B2/ja not_active Expired
1984
- 1984-02-18 JP JP59029453A patent/JPS6011027B2/ja not_active Expired

Also Published As

Publication number	Publication date
GB1457089A (en)	1976-12-01
FR2284593A1 (fr)	1976-04-09
AU8479575A (en)	1977-03-17
ES440962A1 (es)	1977-03-16
JPS6011027B2 (ja)	1985-03-22
CA1072122A (fr)	1980-02-19
FR2284593B1 (fr)	1978-04-07
DE2540432A1 (de)	1976-04-01
NL7510346A (nl)	1976-03-18
JPS5946262B2 (ja)	1984-11-12
JPS59172462A (ja)	1984-09-29
BR7505912A (pt)	1976-08-03
JPS5155345A (fr)	1976-05-15
BE833406A (fr)	1976-03-15

Legal Events

Date	Code	Title	Description
1982-11-18	8110	Request for examination paragraph 44
1985-05-30	8128	New person/name/address of the agent	Representative=s name: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR
1986-07-03	D2	Grant after examination
1987-01-08	8364	No opposition during term of opposition
1988-09-15	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
EP0275832B1 (fr)	1991-10-16	Procédé de préparation de mercaptométhylphénols
DE2414417A1 (de)	1974-10-31	N-(3-hydroxyaryl-propyl)-imide
DE1569041A1 (de)	1969-05-08	Tris-(hydroxyphenyl)-butan
DE69616615T2 (de)	2002-08-01	Cyclische Phenolsulfide und Verfahren zu ihrer Herstellung
DE2929993A1 (de)	1980-02-07	Neue stabilisatoren
DE2540432C2 (de)	1986-07-03	Schwefelhaltige Alkyliden-bisphenole, deren Herstellung und Verwendung als Stabilisatoren
US4254020A (en)	1981-03-03	Synergistic antioxidant mixtures
JPH03177442A (ja)	1991-08-01	エラストマーのための安定剤混合物
DE2211722A1 (de)	1972-09-14	Ester von 4 Alkyl 2,6 dimethyl 3 hydroxy benzylalkohol
DE1811322A1 (de)	1970-06-25	Stabilisatoren
EP0214935B1 (fr)	1993-03-31	Stabiliseurs d'ester de silicium stériquement encombrés
DE2017044C3 (de)	1978-11-02	Nickel-Amid-Komplexe von 2,2'Thiobis-(p-t-octylphenol) und ein Verfahren zu ihrer Herstellung
EP0113318B1 (fr)	1987-09-16	(4-Hydroxyphénylthio)-imides utilisés comme stabilisants
DE2346458C2 (de)	1986-07-31	Thiaalkylphenole, deren Herstellung und das mit ihrer Hilfe stabilisierte organische Material
US4362887A (en)	1982-12-07	Synergistic antioxidant mixtures
DE2902298A1 (de)	1979-08-02	Organische verbindungen
US4370434A (en)	1983-01-25	Mercapto acid ester antioxidants for polymers
DE2231672A1 (de)	1973-01-18	3,5-dialkyl-4-hydroxyphenylalkansaeureester von hydroxyalkylhydroxyalkanoaten
EP0007533B1 (fr)	1982-09-22	Dérivés de la pipéridine, leur procédé de préparation et leur utilisation comme stabilisants de polymères synthétiques
DE2618685A1 (de)	1976-11-11	Neue harnstoff-urethan-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als oxydationsstabilisatoren
EP0137309B1 (fr)	1988-06-29	Esters pluricycliques et copolymères obtenus à partir de ces esters pluricycliques et de carbonates monocycliques.
DE4305422A1 (fr)	1993-08-26
DE2347997A1 (de)	1974-04-04	Bicyclische phosphorverbindungen
EP0116517B1 (fr)	1986-06-18	Ester ou anhydride de l'acide 4-(hydroxy-phényl-thio)-succinique substitué
DE3217665C2 (fr)	1992-01-09