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This page explains what structural isomerism is, and looks at some of the various ways that structural isomers can arise.
Whatare isomers? Isomers are molecules that have the same molecular formula, but have a different arrangement of the atoms in space. That excludes any different arrangements which are simply due to the molecule rotating as a whole, or rotating about particular bonds. For example, both of the following are the same molecule. They are not isomers. Both are butane.
There are also endless other possible ways that this molecule could twist itself. There is completely free rotation around all the carbon-carbon single bonds.
Note: Isomerism is much easier to understand if you have actually got some models to play with. If your school or college hasn't given you the opportunity to play around with molecular models in the early stages of your organic chemistry course, you might consider getting hold of a cheap set. The models made by molymod are both cheap and easy to use. An introductory organic set is more than adequate. Find them at www.molymod.com. Alternatively , get hold of some coloured Plasticene and some used matches and make your own.
If you had a model of a molecule in front of you, you would have to take it to pieces and rebuild it if you wanted to make an isomer of that molecule. If you can make an apparently different molecule just by rotating single bonds, it's not different - it's still the same molecule.
This is easier to see with specific examples. Typesof structuralisomerism Chainisomerism These isomers arise because of the possibility of branching in carbon chains. In one of them. the atoms are arranged in a completely different order. in reality it's anything but straight. Use the BACK button on your browser to return to this page. C 4H10. The names of the various forms of structural isomerism probably don't matter all that much. . For example. If you aren't happy about the ways of drawing organic molecules. follow this link. If you aren't sure. What follows looks at some of the ways that structural isomers can arise. then you must get hold of (or make) some models. Whatare structuralisomers? In structural isomerism. Be careful not to draw "false" isomers which are just twisted versions of the original molecule. this structure is just the straight chain version of butane rotated about the central carbon-carbon bond. the carbon atoms lie in a "straight chain" whereas in the other the chain is branched. there are two isomers of butane. For example. Note: Although the chain is drawn as straight. but you must be aware of the different possibilities when you come to draw isomers.Note: It's really important that you understand this. You could easily see this with a model. This is the example we've already used at the top of this page.
In one of them the bromine atom is on the end of the chain. you would have to move a hydrogen from the middle to the end. but important groups are moved around on that skeleton.Pentane. there are two structural isomers with the molecular formula C 3H7Br. At the same time. Positionisomerism In position isomerism. has three chain isomers. For example. the basic carbon skeleton remains unchanged. If you think you can find any others. If in doubt make some models. whereas in the other it's attached in the middle. You would have to break the bromine off the end and reattach it in the middle. there is no way that you could twist one molecule to turn it into the other one. If you made a model. C5H12. they are simply twisted versions of the ones below. Another similar example occurs in alcohols such as C4H9OH .
but there is no reason why you should do that.that is. the isomers contain different functional groups . You can also get position isomers on benzene rings.you aren't restricted to one or the other. . In one case it is attached to the side-group carbon atom. Functionalgroupisomerism In this variety of structural isomerism. and then there are three other possible positions it could have around the ring . There are four different isomers you could make depending on the position of the chlorine atom. Consider the molecular formula C7H8Cl. next-but-one to the CH3 group. So two other isomers of butanol are: Note: It's essential if you are asked to draw isomers in an exam not to restrict yourself to chain isomers or position isomers. they belong to different families of compounds (different homologous series). You must be aware of all the possibilities. a molecular formula C3H6O could be either propanal (an aldehyde) or propanone (a ketone). For example.These are the only two possibilities provided you keep to a four carbon chain. You can easily have a mixture of chain isomerism and position isomerism .next to the CH3 group. or opposite the CH3 group.
Another common example is illustrated by the molecular formula C 3H6O2.There are other possibilities as well for this same molecular formula . Note: To repeat the warning given earlier: If you are asked to draw the structural isomers from a given molecular formula. Source :30/07/09 from http://www. Amongst the several structural isomers of this are propanoic acid (a carboxylic acid) and methyl ethanoate (an ester).for example. even if it is a valid isomer. don't forget to think about all the possibilities.chemguide.co. you could have a carbon-carbon double bond (an alkene) and an -OH group (an alcohol) in the same molecule.uk/basicorg/isomerism/structural.html © Jim Clark 2000 . you aren't going to get a lot of credit for drawing propanoic acid. Can you branch the carbon chain? Can you move a group around on that chain? Is it possible to make more than one type of compound? Be careful though! If you are asked to draw the structures of esters with the molecular formula C3H6O2.
Current commercial systems are subject to variation both with respect to durability and stop motion.Description TECHNICAL FIELD This invention concerns the lubrication of magnetic recording media such as tapes and flexible or rigid disks. In the case of video tape. In addition. and the demands placed on the lubricant are considerable. as used here. the tape experiences both relative speeds of a few centimeters per second in tape transport and relative speeds of several hundred centimeters per second in video headvelocity. palmitic acid and stearic acid and fatty acid esters. However. tape motion is stopped. In helical scan video recorders. Still-framing in video recorders adds the problem of frictional heat which can damage the binder. the durability of the medium improves. Known lubricants include silicones. BACKGROUND Magnetic recording media are basically heterogeneous structures comprised of both organic (polymeric) and metallic or ceramic materials. Under use. home. temperature variations of 40° C.g.) where some prior art lubricants lose their effectiveness. and humidity variations of 90% are not uncommon. media may face temperature extremes beyond the limits of old lubricant specifications. With increasing amounts of fatty acid and liquid paraffin lubricants. A stop motion test is used in the evaluation of video tapes. There is a recognized need for a better lubricant system for helical scan video tapes. and other less protected and unconventional environments. The temperature generated in the contact area between the rapidly moving head and the tape can be in the order of several hundred degrees centigrade. yet the tape must be protected against wear at both speeds. and this may cause clogging of the recording or playback heads. Lubricants are included in or coated on the magnetizable layer of the recording medium to protect against wear. and the rotating heads scan a particular portion of the recorded material which isdisplayed on a television screen. means oxide or binder build-up on magnetic heads and tape guides. Because disc drives are now being placed in factory. straight chain fattyacids such as myristic acid. New lubricants are desired which areeffective at low temperatures (e. yet themedia must perform well regardless of the environment. a decrease in signal-to-noise output (S/N)at low humidities is a continuing problem and must be improved. reducing its durability. about 5° C. DISCLOSURE OF INVENTION . Debris. and this may cause undue tape wear or the collection of debris on thehead. amounts of lubricant which are too great can softenthe coating. liquid paraffins.
and the viscosity of iso-stearyl alcohol is about 58 cps. and a lubricant comprising an organic compound selected fromthe group consisting of isomers of carboxylic acids and isomers of alcohols said isomers having about 12 to 30 carbon atoms per molecule. viscosity. thus. whereas.. However. Twoparticularly useful lubricants are iso-stearic acid and iso-stearyl alcohol. This helps ensure common physical and chemical properties of the mixture of fatty acid ester and the isomeric acid or alcohol (i. both normal stearic acid and normal stearyl alcoholare solids at that temperature. The recording media having improved lubricant systems described above possess a number of advantages over media lubricated by systems in the prior art.g. They are soluble in common solvents.This invention provides a magnetic recording material comprising: a backing (which may be flexible or rigid). They can withstand stop motion in a helical scan recorder for more than one hour. higher molecular weight species of the isomeric alcohols and acids are preferred. For example. at 80% relative humidity (RH)). Generally. The isomers used in this invention having from 12 to about 24 carbon atoms per molecule are liquids at room temperature. In general.electromagnetic output is improved. (isopropyl alcohol and heptane). S/N loss at dry conditions (10% RH) has been reduced over tapes lubricated with normal myristic acid. As a result. They have greater durability at normal room conditions and in extreme environments (e. a magnetizable layer containing a magnetizable material on said backing. lauric acid and butyl myristate. . the very high molecular weight species (e. The isomers of this invention which are liquids possess distinct handling advantages over the known fatty acid solid lubricants. The liquid nature of these materials results from their molecular configuration which consists of a complex mixture ofisomers having primarily methyl branching. the radio frequency (Rf) decay is less with the new lubricant system. they do not require extra carriersolvent for use. These molecules are mutually soluble in one another and virtually inseparable. The variability of durability in stop motion parameters is reduced from lot to lot of the tapes produced with the improvedlubricant system. In general. the major carbon chain (usually the one derived from a fatty acid) is chosen to have about the same number ofcarbon atoms as the isomeric acid or alcohol.g. Also. Each isomer has a subordinate chain of one or more carbon atoms attached to a carbon atom of the main straight chain. 40 or more carbon atoms per molecule) may suffer from incompatibility with the binder. specific gravity and other physical properties are different from the correspondingsaturated straight chain acid and alcohol. melting point. The prefix "iso" as used in naming organic compounds herein denotes an isomer or mixture of isomers of the named compound.e. the viscosity of iso-stearic acid is about 50 centipoise at 25° C.40° C. similar boiling point range and compatible molecular packing geometries). Preferably the lubricant also comprises a fatty acid ester usually having about 12 to 40 carbon atoms in its molecule. Also. used either alone or in conjunction with a fatty acid ester..
9 for oleic acid) meaning that they have low unsaturation and thus are not subject to auto-oxidation(rancidity) or polymerization. The term magnetizable layer refers to the layer of a recording medium which contains the magnetizable material(e. Although described herein with regard to pigment/binder type media. The dispersion is then applied in a coating process. The lubricant may be either added to a pigment dispersion as an "internal lubricant" or applied as a coating solution in a solvent such as heptane or isopropanol over the magnetizable layer. The term "magnetizable material" is used in this description to refer to the component of the total recording medium (tape or disc) which is the carrier of magnetic signals. The magnetite or gamma ferric oxide may be cobalt doped or cobalt-adsorbed. Polymerization would cause formation of medium molecular weight oligomers which are semi-solid and tacky. and gamma ferric oxide.2-2 weight percent of the magnetizable material (e..g.g. 89.alleviating the problem of dispersion "thin down shock". the dispersion is made by milling the ingredientsof the magnetizable layer (e.g. DETAILED DESCRIPTION The concentration of isomeric alcohol or isomeric acid in the magnetic recording medium is preferably about 0.e. the inventive lubricant system can also benefit other types. No. After coating. the iron oxide. Another advantage of the isomeric acids and alcohols of this invention is that they have low iodine numbers (3. gamma ferric oxide pigment.865. such as gravure or knifecoating.S. Pat. 3. tape or disk) which comprises the magnetizable layer on a backing.0 for iso-stearic acid vs. solvent and lubricant) for a sufficient time to obtain a uniform dispersion.g. pigment/binder layer or thin metal film). Being liquids. the coated material undergoes orientation in a magnetic field to align the pigment particles.g. and about 5 or less weight percent of themagnetizable material for disks. In the case of pigment dispersion type media. . the isomeric analogs have a reduced tendency to plasticize or soften the binder. adding the new lubricant or substituting it for the one formerly used. chromium dioxide. This has been a continuing.. wetting agent. The inventive magnetic recording media can be made by conventional techniques.g. polyester film). These materials are incompatible with the binder matrix used in magnetic media and in time would exude from thecoating possibly causing head clogging. polyurethane binder. Compared to their straight chain precursors. the recording medium is dried. the possibility of bloom or"white-rub off" is eliminated. Typical pigment ormagnetizable materials useful in this system are: magnetite. pigment particles) for tape. chromium dioxide..627) particles in a pigment/binder system or the metal or metal alloy of a thin metal film medium (e. or fine metal (see U.. i. The terms magnetic recording medium and recording medium are defined as the article (e. long-standing problem in the industry.. to a flexible backing (e. such as thin metal film and metal particle media.. After that step. evaporated metal coating).
This invention will be further clarified by a consideration of the following examples. Huguenot.2 percent. The uniform dispersion of Charges 1 and 2 was stirred in a blade mixer. This mixture was milled in the sand mill until a uniform dispersion was obtained containing no visible particleaggregates or agglomerates. and the homogeneous Charge 3 was slowly added. the recording medium was calendered to provide a very smooth magnetizable layer surface. Unless otherwise stated. .2 micrometer.. The Fe3 O4 particles comprised about 72. After heating to drive off the volatile materials.. which are intended to be purely exemplary. vinyl 5 acetate andvinyl alcohol (obtained as VAGH from Union Carbide Corporation) Acicular cobalt encapsulated Fe3 O4 100 particles. designed for helical scan videorecording.3 weight percent of the magnetizable layer.015 mm thick.0 0. The fatty acid ester is normally present in an amount of less than or equal to five weight percent of the magnetizable material and should be present in an amount ranging between about 0. Samples were removed about every two hours and spread manually on a substrate to test uniformity.1 micrometers. the recording media tapes used for the examples were made as follows: Three charges were made: ______________________________________ Components Parts By Weight ______________________________________ Charge 1 Toluene 18 Methyl ethyl Ketone 18 Cyclohexanone 48 Dispersing Agents 6 Copolymer of vinyl chloride. aspect ratio of about 6 to 1. as Wickenol 127). was about 5. The thickness of the finished magnetizable layer.5 ethylene glycol monobutyl ether acetate (obtained as Cellosolve acetate from Union Carbide Corporation) Lubricant(s) 1-2 ______________________________________ Charges 1 and 2 were consecutively stirred in a blade mixer until homogeneous after which they were placed into a sand mill.2 and 2 weightpercent of the magnetizable material for video applications. N. The resulting dispersion (about 42% solids) was immediately rotogravure coated onto biaxially oriented polyester film about0.same as 10 Charge 1 Head cleaning agent (Al2 O3particles. butyl stearate.(high molecular 5 weightpolyesterpolyurethane polymer synthesized from neopentyl glycol and poly-epsilon-caprolactone diol) Charge 2 Toluene 18 Methyl ethyl Ketone 52 Cyclohexanone 18 Organic binder material .The fatty acid ester used in conjunction with the iso-stearyl alcohol or iso-stearic acid may be selected from isopropyl palmitate. Organic binder material . Inc.5 trimethylol propane (obtained as Mondur CB-60 from Mobay Chemical Company) Carrier solvent for the diisocyanate. and the Al2 O3 particles comprised about 2. butoxy ethyl stearate.3 micrometers average particle size) Charge 3 Methyl ethyl Ketone 12 Toluene diisocyanate based adduct of 7. average length about 0. 3. iso-stearyl iso-stearate and isopropyl stearate (available from WickenProducts.Y.
Runnability is a pass/fail test on a commercially available video tape recorder in which two minutes of recorded information is replayed 200 times at controlled temperatureand humidity conditions.5 weight percent iso-stearic acid and 1.g. the medium must lose less than 6 decibels of itsrecorded radio frequency signal. . Thecontrol. EXAMPLE I Representative media were made.0 weight percent isopropyl palmitate (obtained from Wicken Products. weight percents given in the examples are expressed as percent by weight of the magnetizable material (e.. the inventive lubricant Sample A being made of a dispersion containing 0. In order to pass the test. N. 80% relative humidity The same tests were run again on a more extensive sampling than was used for Table 1 and basically confirmed the results shown. Radio frequency (Rf) decay is the measured loss of amplitude in decibels (dB) during the runnability test. the medium must lose no more than 6 decibels of its output signal amplitude.7% butoxyethylstearate (available from Stepan Chemical Company. Inc.7 dB all passed 4 dB Reference A all passed 2. The data from the above described tests.Several tests were used to judge the performance of the lubricated tape.. Stop motion isanother pass/fail test in which a sample of the recording medium is subjected to 60 minutes in the stop-motion or freeze frame mode of a helical scan video player. Generally. The media was slit to 1/2 inch width and loaded into video cassettes of the VHS format. are indicated in Table 1below. used a standard lubricant of butyl myristate and myristic and lauric acids. TABLE 1 ______________________________________ Sample Runnability* Rf Decay Stop Motion S/N Loss ______________________________________ A all passed 2. Signal-to-noise (S/N) loss is the measured loss in signal-to-noise ratio between standard roomconditions (21° C. a difference of greater than 1/2 (dB) is considered significant. ferric oxide particles) in the recording medium. In order to pass the stop motion test.). A significantimprovement in signal-to-noise ratio loss was observed with the new lubrication system.35% iso-stearic acid and 0.Maywood. with only about half the control samples able to pass the runnability and stop motion tests. EXAMPLE II Tapes were also made in the Betamax format and were tested as described above. The results of testing these media are indicated in Table 2 below. Signal-tonoise ratio (S/N) of a test tape is video S/N when playing back a 4 to 5 megaHertz signal recorded on the tape. and test data represents the average of results for testingtwo video tape cassettes. as Wickenol 111).2 dB all passed 8 dB ______________________________________ *at 40° C.J. Reference A. and 50% relative humidity) and 10% relative humidity. in the S/N loss and Rf decay tests. For the Betamax tests. Unless otherwise specified. the experimental dispersion (Sample B) contained 0.
TABLE 2 ______________________________________ Sample Runnability** Stop Motion S/N* ______________________________________ B all passed all passed 3.) where others are not effective. Therefore. the magnetic recording media of this invention are well lubricated and can withstand the frictional heat of video tape player stop motion for long periods of time.e. lubricant wiped or sprayed onto spinning disk) with a three percent solution of lubricant. As shown above. and the physical properties of the new lubricants make these media effective at low temperatures (e.0 ______________________________________ **at21° C. factories)without the sophisticated temperature and humidity controls required for many present day electronic equipment installations. and 50% relative humidity *S/N of Reference B subtracted from S/N value for sake of comparison. and a minimum of three samples of each lubricant were being tested at the same time. EXAMPLE III Wear tests have also been made for diskettes which were aged 90 days before testing. a binder of phenoxy and polyurethane polymers. it can be seen that the use of iso-stearic acid results in an improvement in the electromagnetic output of a video tape. The examples show that the inventive media have good signal tonoise ratios. Ten different drives were used. and the samples were moved so thateach diskette was run on each drive. For each lubricant. the new media may be used with confidence in environments (e. For the samples which were aged 90 days before being tested.. Other embodiments of this invention will be apparent to those skilled in the art from a consideration of this specification or practice of the invention disclosed herein. A dropout or failure was indicated when output level fell below 50% of initial output for that disk.2 Reference B most passed most passed 0. and eachdiskette was spun lubricated (i. conductive carbon and wetting agents. Various omissions. Each had a magnetizable layer comprising gamma Fe2 O3. ten diskettes were wear tested by rotating each one in its jacket with a magnetic recording head riding ona prerecorded test track near the periphery of the disk for a maximum of 48 hours. modifications and changes to the principles describedherein may be made by one skilled in the art without departing from the true scope and spirit of the invention which is indicated by the following claims. the results were: ______________________________________ Percent of Discs Lubricant Passing Wear Test ______________________________________ iso-stearic acid 90% oleic acid 60% isopropyl palmitate 30% ______________________________________ Those which were treated with a coating of iso-stearic acid exhibited a 50% greater success rate in wear testing than diskettes lubricated with oleic acid. Other References .g. 5° C. From the two tables above.g.
Polymer Science and Technology.. 1970 • Tabor. vol. 571. F. 5A.• van Oss. III p. vol. "Chemical Technology: An Encyclopedic Treatment". J. 1974 . D. "Friction. Dr. Adhesion and Boundary Lubrication of Polymers" in Advances in Polymer Friction and Wear..
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