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An expert is someone who has made all of the possible mistakes in a very narrow field of study

Explore the history and chemistry behind the creation of nylon, from the announcement of a brand-new chemical textile fiber to its impact during WWII and beyond. Learn about the structures of nylon, polyurethanes, branching, networks, Bakelite, and crosslinking.

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An expert is someone who has made all of the possible mistakes in a very narrow field of study

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  1. An expert is someone who has made all of the possible mistakes in a very narrow field of study 
 – Niels Bohr

  2. H2N - (CH2)6 - NH2 + HO - C - (CH2)4 - C - OH Hexamethylene Diamine Adipic Acid O O O O H2N - (CH2)6 - N - C - (CH2)4 - C - OH + H2O Amide Group H Nylons

  3. Nylon 6,6 O O - N - (CH2)6 - N - C - (CH2)4 - C - n 6 6 H H “I am making the announcement of a brand new chemical textile fiber ---derivable from coal, air and water -- and characterized by extreme toughness and strength --” Charles Stine V.P. for research, Du Pont, 1938

  4. Nylon “I am making the announcement of a brand new chemical textile fiber ---derivable from coal, air and water -- and characterized by extreme toughness and strength --” Charles Stine V.P. for research, Du Pont, 1938

  5. Nylon May 15 1940 - “Nylon Day” Four million pairs go on sale throughout US Supply exhausted in 4 days.

  6. Nylon Parachute WWII

  7. Post WWII stocking sale, San Francisco

  8. O = C = N - (CH2)6 - N = C = O + HO - (CH2)2 - OH O Hexamethylene Diisocyanate Ethylene Glycol O = C = N - (CH2)6 - N - C - O - (CH2)2 - OH Urethane Linkage H Polyurethanes Reaction does not involve splitting out of a small molecule usw.

  9. Branched - short branches Linear & branched polymers ex: polyethylene Linear

  10. CH2 - CH2 ~~~CH2 - CH CH2 H .CH2 Formation of short chain branches in polyethylene CH2 - CH2 ~~~CH2 - CH CH2 . CH2H CH2 = CH2 C4H9 - ~~~CH2 - CH - CH2 - CH2. C4H9 - ~~~CH2 - CH - CH2 - CH2- CH2 - CH2. CH2 = CH2 Linear & branched polymers ex: polyethylene

  11. Low density polyethylene (LDPE) (short branches)

  12. Other types of branching short long star Branching suppresses or prevents chain movement & "crystallization" in polymers

  13. Branching Another way to make chains branch * * Use multifunctional (f>2) monomers * OH + CH O 2 OH OH OH CH CH CH 2 2 2 OH CH CH CH 2 2 2 OH OH OH CH 2 OH

  14. The phenol + formaldehyde rxn

  15. Network formation Further reaction under heat & pressure builds up densely cross-linked network. This is Bakelite, a thermosettingpolymer. Once reaction is complete, material cannot be reheated and/or reformed Bakelite

  16. Bakelite - Material of a Thousand Uses Bakelite telephone Clear Bakelite items Phenolic resin/celluloidclock Bakelite radio Bakelite microphone Bakelite camera

  17. Crosslinking Take linear polymer chains & link using covalent bonds

  18. - CH2 CH2 - CH2 CH2 - CH2 CH2 - - - - - - - C = C C = C C = C - - - - - - CH3 H CH3 H CH3 H Crosslinking Ex: rxn of natural rubber or poly(isoprene) with sulfur - interconnects the chains by reacting with the double bonds (vulcanization)

  19. Crosslinking

  20. Assignment: Review today's classnotes a. nylons b. polyurethanes c. branching d. networks e. Bakelite f. crosslinking g. vulcanization Read: chapter 14

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