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US3928344A Expired / Lapsed US ⏱️ 0.0 years remaining

Phenylenediamine-s-triazines

Assignee: Evonik Operations GmbH
•
Filing: 1974-05-24
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Granted: 1975-12-23
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Expires: 1994-05-24
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Abstract

Abstract There are prepared 1,3,5-triazines of the formula: WHERE X and Y are SR1 where R1 is alkyl of 1 to 12 carbon atoms or aryl, CN, OR2 where R2 is hydrogen, alkyl of 1 to 12 carbon atoms, aryl, allyl or methallyl, phenyl p-phenylenediamino, where R3 and R4 are hydrogen, alkyl of 1 to 18 carbon atoms, alkyl of 1 to 18 carbon atoms substituted with -OH, -CN or OR5 where R5 is alkyl of 1 to 18 carbon atoms, allyl, methallyl, cycloalkyl of 5 to 8 carbon atoms, aryl or benzyl, one of R3 and R4 is alpha or beta naphthyl and the other is hydrogen, R3 and R4 together with the nitrogen atom form a 5 to 8 membered ring which has from 4 to 7 -CH2- groups of which 0 or 1 hydrogen atom is or of which 2 hydrogen atoms attached to different carbon atoms are substituted by lower alkyl, R3 and R4 together with the nitrogen atom form a 5 to 8 membered ring which has from 3 to 6 -CH2groups of which 0 or 1 hydrogen atom is or of which 2 hydrogen atoms attached to different carbon atoms are substituted by lower alkyl and said ring has one hetero oxygen or sulfur atom or NR6 where R6 is hydrogen or lower alkyl, or X is chlorine, Z is hydrogen, alkyl of 1 to 8 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, phenyl, benzyl, acyl of the formula where R7 is alkyl of 1 to 18 carbon atoms, benzyl or phenyl or the group The compounds are useful to stabilize vulcanized and vulcanizable natural and synthetic rubber compositions.

Inventors

  • 👤 Hermann Westlinning
  • 👤 Werner Schwarze
  • 👤 Horst Fleischhauer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 17:29
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3477; C08K5/3492; C08K5/36

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 7 words
A 1, 3, 5-TRIAZINE OF THE FORMULA:
Claim 2
Dependent Claim 7 words
A 1, 3, 5-TRIAZINE OF THE FORMULA:
Claim 3
Dependent Claim 45 words
A compound according to claim 1 wherein R1 is alkyl of 1 to 12 carbon atoms, phenyl, cresyl, CN, OR2 where R2 is alkyl of 1 to 12 carbon atoms, phenyl, alkylphenyl having 1 to 5 carbon atoms in the alkyl group, allyl or methallyl,
Claim 4
Dependent Claim 9 words
A compound according to claim 1 where Z is:
Claim 5
Dependent Claim 9 words
A compound according to claim 3 where Y is
Claim 6
Dependent Claim 18 words
A compound according to claim 1 where Z is phenyl or alkyl of 1 to 8 carbon atoms.
Claim 7
Dependent Claim 13 words
A compound according to claim 5 where Z is phenyl and Y is
Claim 8
Dependent Claim 12 words
A compound according to claim 6 where R4 is hydrogen or allyl.
Claim 9
Dependent Claim 7 words
A 1, 3, 5-triazine of the formula:
Claim 10
Dependent Claim 7 words
A 1, 3, 5-triazine of the formula:
Claim 11
Dependent Claim 5 words
A 1,3,5-triazine of the formula:
Claim 12
Dependent Claim 5 words
A 1,3,5-triazine of the formula:
Claim 13
Dependent Claim 7 words
A 1, 3, 5-triazine of the formula:
Claim 14
Dependent Claim 7 words
A 1, 3, 5-triazine of the formula:
Claim 15
Dependent Claim 41 words
A compound according to claim 10 wherein any aryl group present as R1 is phenyl or cresyl, as R2 is phenyl or alkylphenyl with 1 to 5 carbon atoms, as R3is phenyl, methylphenyl or naphthyl and R4 is other than aryl.
Claim 16
Dependent Claim 16 words
A compound according to claim 10 wherein X is chlorine, lower alkoxy, allylOxy, or alkylmercapto or
Claim 17
Dependent Claim 10 words
A compound according to claim 12 wherein X is chlorine.
Claim 18
Dependent Claim 10 words
A compound according to claim 10 where X is allyloxy.
Claim 19
Dependent Claim 12 words
A compound according to claim 10 wherein X is allyloxy or methallyloxy.
Claim 20
Dependent Claim 9 words
A compound according to claim 10 wherein X is
Claim 21
Dependent Claim 14 words
A compound according to claim 16 wherein R3 is allyl and R4 is hydrogen.
Claim 22
Dependent Claim 9 words
A compound according to claim 10 wherein Y is
Claim 23
Dependent Claim 10 words
A compound according to claim 18 where R4 is hydrogen.
Claim 24
Dependent Claim 13 words
A compound according to claim 18 wherein R3 and R4 are both allyl.
Claim 25
Dependent Claim 14 words
A compound according to claim 18 wherein R3 is allyl and R4 is hydrogen.
Claim 26
Dependent Claim 7 words
A 1, 3, 5-triazine of the formula:
Claim 27
Dependent Claim 7 words
A 1, 3, 5-triazine of the formula:

References Cited (Backward Citations)

US2524727A Cited
US3149100A Cited
US3240749A Cited
US3309345A Cited
US3291796A Cited
US3658783A Cited
US3755322A Cited
US3758469A Cited
US3767656A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-12-22 1979-06-23 1979-12-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-12-22 1983-06-23 1983-12-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-12-22 1987-06-23 1987-12-23 $7700.00 Window Closed / Lapsed

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