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Phenolic benzothiazole derivatives and their use as corrosion inhibitors

Assignee: BASF Corp
•
Filing: 1987-08-17
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Granted: 1990-01-16
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Expires: 2007-08-17
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Abstract

Abstract Compounds of the formula I ##STR1## wherein R, R 1 , R 2 , R 3 , R 4 and R 5 have the meaning given in claim 1 are formed by thermal rearrangement of the isomers of formula V ##STR2## especially in the presence of basic catalysts. The compounds are corrosion inhibitors for organic materials, in particular coating materials and lubricants. In these substrates they also act as antioxidants and light-stabilizers and are very stable to heat.

Inventors

  • 👤 Adalbert Braig
  • 👤 Hans-Rudolf Meier
  • 👤 David G. Leppard
  • 👤 Robert C. Wasson
  • 👤 Emyr Phillips

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 15:45
CPC Classifications
C; C07; C07D; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/70; C07D277/72; C08; C08K; C08K5/00; C08K5/36; C08K5/45; C08K5/46; C09; C09D; C09D5/00; C09D5/08; C09D5/082; C09D5/086; C09K; C09K15/00; C09K15/04; C09K15/30; C10; C10M; C10M135/00; C10M135/32; C10M135/36; C10M2207/00; C10M2207/10; C10M2207/16; C10M2219/00; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/045; C10N; C10N2010/00; C10N2010/04; C10N2030/00; C10N2030/12

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 413 words
A composition composed of a coating material and containing 0.1 to 20% by weight, based on the solids content of the coating material, of at least one compound of the formula I ##STR21## in which each R independently of one another is hydrogen, C 1 -C 12 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylthio, phenylthio, benzylthio, C 1 -C 12 -alkylsulfonyl, phenyl, C 7 -C 15 -alkylphenyl, C 7 -C 10 -phenylalkyl, C 5 -C 8 -cycloalkyl, halogen, --NO 2 , --CN, --COOH, --COO--(C 1 -C 4 -alkyl), --OH, --NH 2 , --NHR 6 , --N(R 6 ) 2 , --CONH 2 , --CONHR 6 or --CON(R 6 ) 2 , R 1 is hydrogen, C 1 -C 12 -alkyl, phenyl, phenyl which is substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or --NO 2 , pyridyl, thienyl, or furyl, R 2 is hydrogen or C 1 -C 4 -alkyl, R 3 and R 4 independently of one another are hydrogen, halogen, C 1 -C 4 -alkoxy, cyano, nitro, C 1 -C 20 -alkyl, --(CH 2 ) m --COOR 7 , --(CH 2 ) m --CONHR 6 , --(CH 2 ) m --CON(R 6 ) 2 , C 3 -C 20 -alkenyl, C 7 -C 10 -phenylalkyl, phenyl, cyclohexyl, cyclopentyl or a group of the formula II ##STR22## R 5 is hydrogen, C 1 -C 20 -alkyl, C 3 -C 20 -alkenyl or hydroxy, or R 3 and R 5 together or R 4 and R 5 together form a ring fused to the phenolic moiety which ring may be a carbocyclic or heterocyclic ring containing oxygen, nitrogen or sulfur as heteroatoms, each ring being optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, R 6 is C 1 -C 12 -alkyl, C 3 -C 12 -alkyl which is interrupted by one or more O atoms, C 5 -C 8 -cycloalkyl, benzyl, phenyl, or phenyl which is substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or nitro, or --N(R 6 ) 2 is a pyrrolidino, piperidino or morpholino group, R 7 is hydrogen or C 1 -C 20 -alkyl, which may be substituted by halogen or hydroxyl or R 7 is C 3 -C 20 -alkyl which is interrupted by one or more oxygen atoms and may be substituted by hydroxyl and m is 0, 1 or 2.
Claim 2
Dependent Claim 413 words
A composition composed of a coating material and containing 0.1 to 20% by weight, based on the solids content of the coating material, of at least one compound of the formula I ##STR21## in which each R independently of one another is hydrogen, C 1 -C 12 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylthio, phenylthio, benzylthio, C 1 -C 12 -alkylsulfonyl, phenyl, C 7 -C 15 -alkylphenyl, C 7 -C 10 -phenylalkyl, C 5 -C 8 -cycloalkyl, halogen, --NO 2 , --CN, --COOH, --COO--(C 1 -C 4 -alkyl), --OH, --NH 2 , --NHR 6 , --N(R 6 ) 2 , --CONH 2 , --CONHR 6 or --CON(R 6 ) 2 , R 1 is hydrogen, C 1 -C 12 -alkyl, phenyl, phenyl which is substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or --NO 2 , pyridyl, thienyl, or furyl, R 2 is hydrogen or C 1 -C 4 -alkyl, R 3 and R 4 independently of one another are hydrogen, halogen, C 1 -C 4 -alkoxy, cyano, nitro, C 1 -C 20 -alkyl, --(CH 2 ) m --COOR 7 , --(CH 2 ) m --CONHR 6 , --(CH 2 ) m --CON(R 6 ) 2 , C 3 -C 20 -alkenyl, C 7 -C 10 -phenylalkyl, phenyl, cyclohexyl, cyclopentyl or a group of the formula II ##STR22## R 5 is hydrogen, C 1 -C 20 -alkyl, C 3 -C 20 -alkenyl or hydroxy, or R 3 and R 5 together or R 4 and R 5 together form a ring fused to the phenolic moiety which ring may be a carbocyclic or heterocyclic ring containing oxygen, nitrogen or sulfur as heteroatoms, each ring being optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, R 6 is C 1 -C 12 -alkyl, C 3 -C 12 -alkyl which is interrupted by one or more O atoms, C 5 -C 8 -cycloalkyl, benzyl, phenyl, or phenyl which is substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or nitro, or --N(R 6 ) 2 is a pyrrolidino, piperidino or morpholino group, R 7 is hydrogen or C 1 -C 20 -alkyl, which may be substituted by halogen or hydroxyl or R 7 is C 3 -C 20 -alkyl which is interrupted by one or more oxygen atoms and may be substituted by hydroxyl and m is 0, 1 or 2.
Claim 3
Dependent Claim 37 words
A composition according to claim 1, wherein, in formula I and II, one R is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen, trifluoromethyl or nitro and the other three R's are hydrogen.
Claim 4
Dependent Claim 27 words
A composition according to claim 1, wherein in formula I, R 1 is hydrogen, C 1 -C 8 -alkyl, phenyl or furyl and R 2 is hydrogen.
Claim 5
Dependent Claim 17 words
A composition according to claim 1, wherein R 1 and R 2 in formula I are hydrogen.
Claim 6
Dependent Claim 90 words
A composition according to claim 1, wherein, in formula I, R 3 and R 4 independently of one another are hydrogen, C 1 -C 8 -alkyl, allyl, C 7 -C 10 -phenylalkyl, C 1 -C 4 -alkoxy, halogen, phenyl, cyclohexyl, or a group --CH 2 CH 2 COOR 7 , R 5 is hydrogen, C 1 -C 18 -alkyl, C 3 -C 18 -alkenyl or OH and R 7 is C 1 -C 18 -alkyl or C 3 -C 20 -alkyl which is interrupted by one or more oxygen atoms.
Claim 7
Dependent Claim 66 words
A composition according to claim 1, containing a compound of the formula III ##STR23## wherein R is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, chlorine, trifluoromethyl or nitro, R 3 and R 4 independently of another are hydrogen, C 1 -C 8 -alkyl, allyl, chlorine, methoxy, C 7 -C 10 -phenylalkyl, phenyl or cyclohexyl and R 5 is hydrogen, methyl or OH.
Claim 8
Dependent Claim 95 words
A composition according to claim 1, containing a compound of the formula IV ##STR24## in which R is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, chlorine, trifluoromethyl or nitro, R 3 and R 4 independently are hydrogen, C 1 -C 8 -alkyl, C 7 -C 10 -phenylalkyl, phenyl cyclohexyl or a group of the formula IIa ##STR25## and R 5 is hydrogen, C 1 -C 18 -alkyl, C 3 -C 18 -alkenyl or R 3 and R 5 together form a benzene, pyridine or benzofuran ring fused to the phenolic ring.
Claim 9
Dependent Claim 13 words
A composition according to claim 1 which is a primer for metallic substrates.
Claim 10
Dependent Claim 17 words
A composition according to claim 8 which is a primer on iron, steel, copper, zinc or aluminium.
Claim 11
Dependent Claim 12 words
A composition according to claim 1 which is an aqueous coating material.
Claim 12
Dependent Claim 13 words
A composition according to claim 10 which is a cathodic deposible coating material.
Claim 13
Dependent Claim 36 words
A coating material composition according to claim 1 containing 0.5 to 5 percent by weight, based on the solids content of the composition, of at least one compound of formula I as defined in claim 1.
Claim 14
Dependent Claim 30 words
A composition according to claim 1 containing a coating material selected from the group consisting of an epoxide, polyurethane, aminoplast, acrylic, alkyd or polyester resin a mixture of such resins.
Claim 15
Dependent Claim 29 words
A composition according to claim 1 containing a coating material on the basis of a vinyl resin, cellulose ester, chlorinated rubber, phenolic resin, styrene-butadiene copolymer and a drying oil.
Claim 16
Dependent Claim 10 words
A composition according to claim 1 containing the compound 3-(3,5-di-tert.butyl-4-hydroxybenzyl)-benzothiazole-2-thione.
Claim 17
Dependent Claim 10 words
A composition according to claim 1 containing the compound 3-(4-pentadecyl-2-hydroxybenzyl)-benzothiazole-2-thione.
Claim 18
Dependent Claim 10 words
A composition according to claim 1 containing the compound 3-(4-hydroxybenzyl)-benzothiazole-2-thione.
Claim 19
Dependent Claim 10 words
A composition according to claim 1 containing the compound 3-(2,3,5-trimethyl-4-hydroxybenzyl)-benzothiazole-2-thione.
Claim 20
Dependent Claim 10 words
A composition according to claim 1 containing the compound 2,4-di(benzothiazol-2-thion-3-ylmethyl)-6-methylphenyl.

References Cited (Backward Citations)

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US3219701A Cited
EP0003817A1 Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-01-15 1993-07-17 1994-01-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-01-15 1997-07-17 1998-01-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-01-15 2001-07-17 2002-01-16 $7700.00 Window Closed / Lapsed

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