Table Of Content1 Introduction of Macromolecular
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In Introduction of Macromolecular Science/Polymeric Materials into the Foundational Course in Organic Chemistry; Howell, B.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2013.
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In Introduction of Macromolecular Science/Polymeric Materials into the Foundational Course in Organic Chemistry; Howell, B.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2013.
1151
ACS SYMPOSIUM SERIES
Introduction of Macromolecular
Science/Polymeric Materials
into the Foundational Course in
Organic Chemistry
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1 Bob A. Howell, Editor
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AmericanChemicalSociety,Washington,DC
DistributedinprintbyOxfordUniversityPress
In Introduction of Macromolecular Science/Polymeric Materials into the Foundational Course in Organic Chemistry; Howell, B.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2013.
LibraryofCongressCataloging-in-PublicationData
1 Introductionofmacromolecularscience/polymericmaterialsintothefoundationalcourse
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0 inorganicchemistry/BobA.Howell,editor,CentralMichiganUniversity,Mt.Pleasant,
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1.f Michigan;sponsoredbytheACSDivisionofChemicalEducation.
15 pagescm.-- (ACSsymposiumseries;1151)
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3- Includesbibliographicalreferencesandindex.
01 ISBN978-0-8412-2878-8(alk.paper)
2
k- 1. Macromolecules--Congresses.2. Polymers--Congresses.3. Chemistry,Organic--
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1/ Congresses. I.Howell,B.A.(BobbyAvery),1942-editorofcompilation.II.American
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0 ChemicalSociety.DivisionofChemicalEducation,sponsoringbody.
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In Introduction of Macromolecular Science/Polymeric Materials into the Foundational Course in Organic Chemistry; Howell, B.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2013.
Foreword
The ACS Symposium Series was first published in 1974 to provide a
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sponsoredsymposiabasedoncurrentscientificresearch. Occasionally,booksare
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In Introduction of Macromolecular Science/Polymeric Materials into the Foundational Course in Organic Chemistry; Howell, B.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2013.
ix
interiorofthehouse(Figure1).
several polymers are utilized just for wall construction to say nothing of the
with an acrylate polymer applied as a latex containing a suitable pigment. Thus
polymer. The surface of the dry wall facing the interior of the house is coated
containing gypsum as a main component held in place by sheets of a cellulosic
and is constructed from dry wall (sheet rock). Dry wall is a layered structure
insulation, an inorganic polymer. The next layer forms the interior of the wall
with a phenol-formaldehyde adhesive. Beneath the sheeting is spun fiberglass
Thesheetingisplywoodwhichiscomprisedofthinwoodlaminatesheldtogether
insulation,coveringthesheetingisusuallyabarrierlayerofTyvec,apoly(amide).
insulation. This insulation is made from foamed poly(styrene). Beneath the
01 require maintenance. Beneath the vinyl siding is 2 or 4 inches of styrofoam
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pr color, is durable (lasts longer than other components of the house) and does not
1.
15 siding, i.e., poly(vinyl chloride) [PVC]. It can be pigmented in any attractive
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3- isstronglydependentonthesematerials. Theexteriorofthehomeisoftenvinyl
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20 in several simple illustrations. For example, the construction of a modern home
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b The importance of polymeric materials in modern society may be reflected
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02 well-beingofsociety.
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0. the central role that these materials occupy in their daily lives and the overall
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oi: to stimulate student interest and enthusiasm for the course and to emphasize
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3 | oforganicchemistry. Inclusionofsometreatmentofpolymericmaterialsserves
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2, formed by simple, easily-understood organic reactions. The preparation of
2
er commonly used by the consuming public are organic in composition and are
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No beapartofallfoundationalcoursesinchemistry. Thisis, perhaps, mostreadily
b): guidelines contain the expectation that a treatment of polymeric materials will
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ate ( will work in a polymer or a polymer-related area. This situation has been
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ati materials are largely responsible by the quality of life that everyone enjoys and
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in Foundational Chemistry Courses
TheNeedToProvideSomeIntroductiontoPolymericMaterials
Preface
In Introduction of Macromolecular Science/Polymeric Materials into the Foundational Course in Organic Chemistry; Howell, B.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2013.
x
of polymeric materials. In the interior, the dash is from PVC. Seat covers may
components. In fact, its construction is strongly dependent on the availability
The automobile sitting in the driveway also contains many polymeric
items,medicines,andthelikethatmaybepresentinthehome.
reflect polymeric components of food packaging, the food itself, personal care
poly(tetrafluorethylene) [Teflon]. And this is but a partial listing and does not
or poly(propylene). The non-stick surface on baking and fry pans is made from
Simplekitchenutensils(bowls,pitchers,etc.) maybemadefrompoly(ethylene)
and coated with a poly(siloxane) or fluorocarbon polymer to resist staining.
original shape. Covers for couches are woven from nylon fiber (very durable)
backedintoarefrigeratorthehousingdoesnotdentorbreakbutreboundstoits
from ABS. These housings are lightweight, resilient and durable. If a chair is
appliances(washer/drierunits,dishwashers,refrigerators,freezers,etc)aremade
1 is much durable and resisitant to damage than is wood. Housings for common
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pr0 materialcanbegiventheappearanceofanycommonwoodgrainbut,ofcourse,
51. furniture may be from an acrylonitrile-butadiene-styrene (ABS) polymer. This
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21/ Plumbing pipe for the house is constructed from PVC, as is the tile in the
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3 | d Figure1. PolymericComponentsofaTypicalHomeWall
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In Introduction of Macromolecular Science/Polymeric Materials into the Foundational Course in Organic Chemistry; Howell, B.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2013.
xi
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We chemistry. Therearemanywaysthatpolymericmaterialsmaybeincludedinthe
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materials in supporting the modern lifestyle should be apparent from this brief
food or several others. However the pervasiveness, and utility of polymeric
Similarexamplescouldbedrawnfromtheareasofmedicine,personalcare,
mentionseveralelastomerscontainedinthetires.
siloxanepolymers,protectivecoatingsfrompoly(urethane),andonandon,notto
covers from poly(propylene), gaskets from neoprene [poly(chloroprene)] or
fromnylon,fueltanksfrompoly(ethylene),wiringinsulationfromPVC,battery
poly(styrene), bumpersfrompoly(carbonate), exhaustmanifoldsandbrakelines
from ABS, fenders and valve covers from poly(propylene), light covers from
[Delrin]. Polymers are prominent in other areas as well. Side panels are made
Gears in dashboard instruments are made from nylon or poly(oxymethylene)
befromthesamematerial. Theseatsthemselvesaremadefrompoly(urethane).
In Introduction of Macromolecular Science/Polymeric Materials into the Foundational Course in Organic Chemistry; Howell, B.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2013.
©2013AmericanChemicalSociety
connectionbetweenteachingmaterialandtherealworld.
Society programs to utilize polymers to enhance this natural
andtheefforttoassistteachersandvariousAmericanChemical
presented material describing PolyEd and its many programs
in the curriculum materials called organic chemistry. Here is
that science is important and pervasive. It is clearly apparent
between material presented to students at all levels and reality
worldofpractice. Itservesasaclearandpersuasiveconnection
1 Polymersareanaturalbridgebetweenteachingmaterialandthe
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51. in science, medicine, environment, communications, and
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3-1 also do polymers. Polymers are a bridge to many topic areas
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3 | d BocaRaton,Florida33431
01 4DepartmentofChemistryandBiochemistry,FloridaAtlanticUniversity,
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2, Wisconsin54481
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er 3Department of Chemistry, University of Wisconsin,-Stevens Point,
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Nov 2DepartmentofChemistry,PortlandStateUniversity,Portland,
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We 1DepartmentofChemistry,CentralMichiganUniversity,Mt. Pleasant,
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Chemistry Content and the Polymer Education
Topics Within the Foundational Organic
Integration of Macromolecular/Polymeric
Chapter 1
In Introduction of Macromolecular Science/Polymeric Materials into the Foundational Course in Organic Chemistry; Howell, B.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2013.
2
formationandnaturalamideformationreactionsresultinginproteinformation.
ofmonoamideformationandalsoallowsthecomparisonbetweensyntheticamide
Equation2describesthesynthesisofnylon66. Thisissimplytheextension
of"greenchemistry"incommercialproductionofitemstheyarefamiliarwith.
thesynthesisofethyleneglycolfromnatural"green"materialsallowsdiscussion
Mechanisticdiscussionsarealsoappropriatetointroduceatthisjuncture. Further,
canberemindedofthewideusesofethyleneglycolincludinguseinantifreeze.
The formation of PET employs ethylene glycol as the diol and again, students
the importance of ester synthesis in the world that students are familiar with.
composes most of the soda and water bottles produced today. This illustrates
tradenames including Dacron and Kodel. It is also employed as a plastic that
processes. PET is the most widely synthesized fiber sold under a variety of
PETorPETE,istheextensionofmonomericestersynthesis. Bothareequilibrium
1 poly(ethyleneterephthalate),esters. Thesynthesisofpoly(ethyleneterephthalate),
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h reactions. Equation 1 describes the synthesis of monomeric and polymeric,
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51. Equations 1 and 2 outline the synthesis of two important condensation
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3-1 citedinTable1andthatshouldbeconsideredinfoundationalorganiccontent.
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21/ examplesofthedivergenceofpolymericmaterials. Ourfocushereisonorganic
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3 | d macromolecules used to describe biological materials (4, 5). Here, we will use
1 with the term polymers employed to describe synthetic materials while the term
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2, Attimestherearethosethatdividethetermsmacromoleculesandpolymers
2
er GoodandEdwinVandenberg.
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We Pauling and Alan McDiarmid; American Chemical Society Presidents including
e ( PolyEd has had association with Nobel Prize winners Paul Flory, Linus
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of polymers also encourages the application and importance of materials and
polymers allows much of the basic science knowledge to be presented. The use
Polymersareanaturalbridgebetween“therealworld”andscience. Using
oflife,ofcommerce,ofhealth,ofcommunication,etc.
theyarethesinglemostimportantclassofmaterials. Polymersarethematerials
importancebetweentherealworldandthedevelopingworldofscience. Further,
ofstudents(1–3). Useofpolymersisalsoimportantinconveyingtosocietythe
theteachingofbasicconceptsthroughouttheacademicandpost-academiccareer
toanobservedneedthatpolymersandpolymer-relatedexamplescancontributeto
ThePolymerEducationCommittee,PolyEd,wasformedin1974inresponse
Introduction
In Introduction of Macromolecular Science/Polymeric Materials into the Foundational Course in Organic Chemistry; Howell, B.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2013.
