Source: http://www.google.com/patents/US20110040125?ie=ISO-8859-1
Timestamp: 2015-05-05 17:45:20
Document Index: 646462216

Matched Legal Cases: ['Application No. 60', 'Application No. 60', 'Application No. 60', 'Application No. 60', 'Application No. 60', 'Application No. 60', 'Application No. 60']

Patent US20110040125 - Nitrogen and hindered phenol containing dual functional macromolecular ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsDisclosed are compounds represented by structural formula (I): methods of producing compounds represented by structural formula (I), and their use in inhibiting oxidation in an oxidizable material....http://www.google.com/patents/US20110040125?utm_source=gb-gplus-sharePatent US20110040125 - Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis, performances and applicationsAdvanced Patent SearchPublication numberUS20110040125 A1Publication typeApplicationApplication numberUS 12/854,347Publication dateFeb 17, 2011Filing dateAug 11, 2010Priority dateFeb 22, 2005Also published asCA2598703A1, EP1861484A2, US7799948, US8080689, US8710266, US20060189824, US20120142968, US20140316163, WO2006091705A2, WO2006091705A3Publication number12854347, 854347, US 2011/0040125 A1, US 2011/040125 A1, US 20110040125 A1, US 20110040125A1, US 2011040125 A1, US 2011040125A1, US-A1-20110040125, US-A1-2011040125, US2011/0040125A1, US2011/040125A1, US20110040125 A1, US20110040125A1, US2011040125 A1, US2011040125A1InventorsRajesh Kumar, Suizhou Yang, Vijayendra Kumar, Ashok L. CholliOriginal AssigneePolnox CorporationExport CitationBiBTeX, EndNote, RefManClassifications (24), Legal Events (2) External Links: USPTO, USPTO Assignment, EspacenetNitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis, performances and applications
US 20110040125 A1Abstract
Rx is �H or an optionally substituted alkyl;
Ry is �H or an optionally substituted alkyl;
each R′ is independently �H or an optionally substituted alkyl;
R″ is �H, an optionally substituted alkyl, an optionally substituted aryl or an optionally substituted aralkyl;
each Ra is independently a C1-C20 alkyl; each Rc is independently a C1-C10 alkyl; and R″ is �H, a C1-C20 alkyl or an optionally substituted aralkyl. 3. The compound of claim 2, wherein the compound is represented by the following structural formula:
m is 1 or 2; and s is 0 or 1. 5. The compound of claim 4, wherein the compound is represented by the following structural formula:
each Ra is independently a C1-C10 alkyl; R″ is �H, a C1-C10 alkyl or a substituted benzyl group; and n is an integer from 1 to 6. 7. The compound of claim 6, wherein the compound is selected from the group consisting of:
The term �alkoxy� as used herein is represented by OR**, wherein R** is an alkyl group as defined above.
Each R1 is independently an optionally substituted alkyl or optionally substituted alkoxycarbonyl. R′ is �H or an optionally substituted alkyl. u is an integer from 1 to 4, Additional values for these variables are as described above. In one embodiment the phenol derivative is selected from:
Each Rc, is independently an optionally substituted alkyl or an optionally substituted alkoxycarbonyl. R′ is �H or an optionally substituted alkyl. R** is an optionally substituted alkyl. o is an integer from 1 to 10. u is an integer from 1 to 4. Additional values for these variables are as described above. In another embodiment the amino-phenol is selected from the group consisting of:
In certain other embodiments of the present invention after combining the amine and phenolic-carbonyl derivative in a suitable solvent the combination is refluxed at a temperature between 50 and 180� C., between 60 and 130� C., between 70 and 110� C. In certain embodiments, the combination is refluxed for between 1 and 48 hours, between 6 and 36 hours, between 12 and 24, hours or between 18 and 20 hours.
2,6-di-tert-butyl-4-(dimethyl-aminomethyl)phenol (26.3 g) and N-Phenyl-1,4-phenylene-diamine (18.4 g) were dissolved in 50 ml toluene. The reaction mixture was refluxed at 100� C. using a Dean Stark apparatus equipped with a condenser. After completion, the solvent was removed by distillation and ice-cold water added and refluxed. The reaction mixture was cooled to room temperature and product was isolated by filtration. The product (A) was characterized using spectroscopic techniques such as high resolution 1H NMR, 13C NMR and FT-IR.
2,6-di-tert-butyl-4-(dimethyl-aminomethyl)phenol (3 g) and N-Phenyl-1,4-phenylene-diamine (2 g) were dissolved in 100 ml toluene. The reaction mixture was refluxed at 100� C. using a Dean's Stark apparatus equipped with a condenser. The reaction was monitored by thin layer chromatography. After completion, the solvent was removed by distillation and the resultant mixture was purified by column chromatography. The purified compound was characterized by spectroscopic techniques.
2,6-di-tert-butyl-4-(dimethyl-aminomethyl)phenol (32 g) and N-Phenyl-1,4-phenylene-diamine (18.4 g) were dissolved in 50 ml toluene. The reaction mixture was refluxed at 100� C. using a Dean's Stark apparatus equipped with a condenser. After completion, the solvent was removed by distillation and ice-cold water added and refluxed. The reaction mixture was cooled to room temperature and product was isolated by filtration. The purified compound was characterized by spectroscopic techniques.
2,6-di-tort-butyl phenol (10.3 g), paraformaldehyde (1.8 g) and N-hexyl-Phenyl-1,4-phenylene-diamine (16.08 g) were dissolved in 75 ml methanol. The reaction mixture was refluxed at 70� C. using a Dean's Stark apparatus equipped with a condenser. After completion, the solvent was removed by distillation and ice-cold water added and refluxed. The reaction mixture was cooled to room temperature and product was isolated by filtration. The purified compound was characterized by spectroscopic techniques.
2-methyl, 6-tert-butyl phenol (16.4 g), paraformaldehyde (3.6 g) and N-Phenyl-1,4-phenylene-diamine (22 g) were dissolved in 50 ml methanol, The reaction mixture was refluxed at 70� C. using a Dean's Stark apparatus equipped with a condenser. After completion, the solvent was removed by distillation and ice-cold water added and refluxed. The reaction mixture was cooled to room temperature and product was isolated by filtration and purified by column chromatography. The purified compound was characterized by spectroscopic techniques.
Macromolecules V and A were tested for their performance in lubricant oils and polymers. The macromolecules were mixed in oil with stirring at 60� C. for 5-15 mins at 200 ppm in petroleum based Group II base stock and polyol based Group V base stock oils. The performance of these antioxidants were evaluated in lubricant base oil stocks including Group II using the DSC technique for determining their oxidation induction times measured in minutes (OTT) at 200� C. The OITs of the antioxidants having structures V and A were compared with commercial antioxidants [L57: Ciba's Irganox L57, 6PPD: N-hexyl phenyl-1,4-phenylene diamine CAS # 793-24-8)]. The results are shown in FIG. 2 which shows the superior performance of V and A.
10 g of the antioxidant V was added to 90 g of Group II lubricant oil base stock in a beaker. The resultant mixture was stirred for 15 mins in a oil bath maintained at 60� C. to give a homogenous solution. This homogenous solution was used for evaluation. This solubility is much higher than the typical industry standards of 1-2%.
Docket No.: 3805.1000-000; Provisional Patent Application No.: 60/632,893, filed Dec. 3, 2004, Title: Process For The Synthesis Of Polyalkylphenol Antioxidants, by Suizhou Yang, et al; Docket No.: 3805.1000-003; patent application Ser. No. 11/292,813 filed Dec. 2, 2005, Title: Process For The Synthesis Of Polyalkylphenol Antioxidants, by Suizhou Yang, et al; Docket No.: 3805.1001-000; Provisional Patent Application No. 60/633,197, filed Dec. 3, 2004, Title: Synthesis Of Sterically Hindered Phenol Based Macromolecular Antioxidants, by Ashish Dhawan, et al.; Docket No.: 3805.1001-003; patent application Ser. No. 11/293,050; filed Dec. 2, 2005, Title: Synthesis Of Sterically Hindered Phenol Based Macromolecular Antioxidants, by Ashish Dhawan, et al.; Docket No.: 3805.1002-000; Provisional Patent Application. No. 60/633,252, filed Dec. 3, 2004, Title: One Pot Process For Making Polymeric Antioxidants, by Vijayendra Kumar, et al.; Docket No.: 3805.1002-003; patent application Ser. No. 11/293,049; filed Dec. 2, 2005, Title: One Pot Process For Making Polymeric Antioxidants, by Vijayendra Kumar, et al.; Docket No.: 3805.1003-000; Provisional Patent Application No. 60/633,196, filed Dec. 3, 2004, Title: Synthesis Of Aniline And Phenol-Based Macromonomers And Corresponding Polymers, by Rajesh Kumar, et al.; Docket No.: 3805.1003-003; patent application Ser. No. 11/293,844; filed Dec. 2, 2005, Title: Synthesis Of Aniline And Phenol-Based Macromonomers And Corresponding Polymers, by Rajesh Kumar, et al.; Docket No.: 3805.1004-002; patent application Ser. No. 11/184,724, filed Jul. 19, 2005, Title: Anti-Oxidant Macromonomers And Polymers And Methods Of Making And Using The Same, by Ashok L. Cholli; Docket No.: 3805.1004-005; patent application Ser. No. 11/184,716, filed Jul. 19, 2005, Title: Anti-Oxidant Macromonomers And Polymers And Methods Of Making And Using The Same, by Ashok L. Cholli; Docket No.: 3805.1005-000; Provisional Patent Application No. 60/655,169, filed Feb. 22, 2005, Title: Nitrogen And Hindered Phenol Containing Dual Functional Macromolecules: Synthesis And Their Antioxidant Performances In Organic Materials, by Rajesh Kumar, et al. Docket No.: 3805.1006-000; Provisional Patent Application No. 60/655,169, filed Mar. 25, 2005, Title: Alkylated Macromolecular Antioxidants And Methods Of Making, And Using The Same, by Rajesh Kumar, et al. Docket No.: 3805.1007-000; Provisional Patent Application No. 60/731,125, filed Oct. 27, 2005, Title: Macromolecular Antioxidants And Polymeric Macromolecular Antioxidants, by Ashok L. Cholli, et al. Docket No.: 3805.1008-000; Provisional Patent Application No. 60/731,021, filed Oct. 27, 2005, Title: Macromolecular Antioxidants Based On Sterically Hindered Phenols And Phosphites, by Ashok L. Cholli, et al. Docket No.: 3805.1009-000; Provisional Patent Application No. ______, filed Dec. 2, 2005, Title: Lubricant Composition, by Kumar, Rajesh, et al. Docket No.: 3805.1010-000; Provisional Patent Application No. 60/731,325, filed Oct. 27, 2005, Title: Stabilized Polyolefin Composition, by Kumar, Rajesh, et al. Docket No.: 0813.2006-003; patent application Ser. No. 11/040,193, filed Jan. 21, 2005, Title: Post-Coupling Synthetic Approach For Polymeric Antioxidants, by Ashok L. Choll, et al.; Docket No.: 0813.2006-002; Patent Application No.: PCT/US200S/001948, filed Jan. 21, 2005, Title: Post-Coupling Synthetic Approach For Polymeric Antioxidants, by Ashok L. Cholli et al.; Docket No.: 0813.2002-008; Patent Application No.: PCT/US2005/001946, filed Jan. 21, 2005, Title: Polymeric Antioxidants, by Ashok L. Choll, et al.; Docket No.: 0813.2002-006; Patent Application No.: PCT/US03/10782, filed Apr. 4, 2003, Title: Polymeric Antioxidants, by Ashok L. Choll, et al.; Docket No.: 0813.2002-004; patent application Ser. No. 10/761,933, filed Jan. 21, 2004, Title: Polymeric Antioxidants, by Ashish Dhawan, et al.; Docket No.: 0813.2002-001; patent application Ser. No. 10/408,679, filed Apr. 4, 2003, Title: Polymeric Antioxidants, by Ashok L. Choll, et al.; US patent No.: U.S. Pat. No. 6,770,785 B1 US patent No.: U.S. Pat. No. 5,834,544 Neftekhimiya (1981), 21(2): 287-298. While this invention has been particularly shown and described with references to preferred embodiments thereof, it will be understood by those skilled in the art that various changes in faun and details may be made therein without departing from the scope of the invention.
Classifications U.S. Classification564/390, 564/389International ClassificationC07C215/74Cooperative ClassificationC10M2207/026, C07C215/50, C07C213/02, C07C229/38, C10M159/12, C10N2230/10, C10M2215/04, C10M2215/066, C10M2207/08, C10M133/14, C10M177/00, C08K5/005, C10M2215/06, C10N2270/00, C10M149/22European ClassificationC07C229/38, C07C215/50, C10M149/22, C10M177/00, C10M159/12, C10M133/14Legal EventsDateCodeEventDescriptionDec 20, 2014FPAYFee paymentYear of fee payment: 4Dec 6, 2010ASAssignmentOwner name: POLNOX CORPORATION, MASSACHUSETTSFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KUMAR, RAJESH;YANG, SUIZHOU;KUMAR, VIJAYENDRA;AND OTHERS;REEL/FRAME:025455/0798Effective date: 20060330RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services