Unlock instant, AI-driven research and patent intelligence for your innovation.

Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including such compounds

A technology of anti-degradants, compounds used in lubricating compositions, organic chemistry, transportation and packaging to address issues such as detrimental tire performance, appearance and life expectancy

Active Publication Date: 2020-01-14
EASTMAN CHEM CO
View PDF11 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As discussed in U.S. Patent No. 2,905,654, oxygen degradation affects rubber production differently than ozone degradation does; however, both effects can be detrimental to tire performance, appearance, and life expectancy

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including such compounds
  • Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including such compounds
  • Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including such compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0129] Example 1: Precursor (N,N',N,N')-N,N'-(2,2,4,4-tetramethylcyclobutane-1,3-diylidene)bis(N - Preparation of phenylbenzene-1,4-diamine)

[0130]

Embodiment 2

[0132] Example 2: Preparation of N,N'-(2,2,4,4-tetramethylcyclobutane-1,3-diyl)bis(N-phenylbenzene-1,4-diamine)

[0133]

[0134] LiAlH in a 1L round bottom flask 4 (8.45 g, 223 mmol) was carefully added to THF (223 mL). Diimine (26.3 g, 55.7 mmol) was carefully added to the solution. After the addition was complete, the reaction was refluxed for 4 hours. After this time, the mixture was cooled using a cold water bath, and then carefully quenched by the dropwise addition of water (10 mL) followed by 15% NaOH (20 mL). The mixture was stirred overnight. After filtration, the brown liquid was concentrated under reduced pressure using a rotary evaporator. The product (shown as 2 in the above scheme) was isolated as a tan solid (24.6 g, 93% yield) ( 1 H NMR showed a mixture of cis and trans isomers) T m = 179.5°C. 1 H NMR (300 MHz, CDCl 3 ) δ 8.56 (m, 4H), 8.37 (m, 4H), 8.23-8.13 (m, 6H), 8.02-7.94 (m, 4H). 6.76 (bs, 2H), 5.28-5.13 (m, 2H) , [4.77(bs), 4.71 (bs) 2H tot...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

Antidegradant compounds are disclosed, and methods of making them, that are represented by the formula (I), wherein each X is independently selected from the group consisting of ethyl, methyl, or hydrogen. Also disclosed are diimine intermediates corresponding to formula (III), wherein each X is independently selected from the group consisting of ethyl, methyl, or hydrogen. These intermediates themselves exhibit antidegradant activity.

Description

technical field [0001] The present invention relates generally to compounds and methods for their preparation which have anti-degradant and anti-fatigue benefits and are useful as vulcanized rubber articles, vulcanizable elastomer formulations, lubricants, fuels, fuel additives and other applications requiring such benefits Additives to the composition or may be used in the composition itself may be used as a composition to impart such benefits. Background technique [0002] Many materials such as plastics, elastomers, lubricants, cosmetics, and petroleum products (such as hydraulic fluids, oils, fuels, and oil / fuel additives used in automotive and Easily degraded by mechanical action etc. Accordingly, compounds and compositions that exhibit efficacy of antidegradants are well known in the art. For example, US Patent No. 8,987,515 discloses aromatic polyamines useful for inhibiting oxidative degradation, especially in lubricant compositions. US Patent Application Publicat...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54C07C251/20C08K5/18B60C1/00C10L1/223C10L10/08C10M133/22C10M133/12
CPCB60C1/00C07C211/54C07C251/20C08K5/18C10L1/223C10L10/08C10M133/12C10M133/22C10M2215/067C10L2230/081C07C2601/04C10N2030/10C10N2030/08C08L21/00
Inventor M.A.布恩D.L.小菲尔兹F.伊纳茨-胡佛
Owner EASTMAN CHEM CO