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USES OF FORMALDEHYDE 309 Fig, 24a. Urea-formaldehyde resins—plastic switch pkue. Ctiu-rfpej/ BakvHte Corporation. Fig. 24b. Radio with urea resin cabinet.
310 FORMALDEHYDE has played an increasingly important role as a raw material for the production of aikyd resins, particularly the rosm-maleic alkyds. Thermoplastic Synthetic Resins. Thermoplastic resins m&y be synthesized by reaction* analogous to those which take place in the production of thermosetting resins. They are made by reaction of formaldehyde with simple molecules containing two or more hydrogen atoms capable of reacting in such a manner that linear or, in some cases, cyclic condensates are obtained. Compounds of this type are fusible and can be dissolved in some solvent?. The formation of thermoplastic resins is indicated in the following equation in which ('A) Hi represents an organic raw material of the type required. K(A;.H2 -f rcCH20 -+ ... (A)— CHi— (A)— CH2— (A)—CH*... 4- nH30 The hydrogen atoms indicated in (A)H2 may be on-hydroxyl groups, amino groups, amido groups, activated positions of an aromatic nucleus, etc. "When compounds having more than two active hydrogen atoms are employed, the reaction must be controlled to prevent cross-linking, which would result in the formation of an infusible or thermosetting resin. In some cases, this is not possible and raw materials employed for the production of thermosetting resins cannot always be utilized in the preparation of thermoplastics. True thermoplastic resins apparently cannot be prepared by reactions involving urea and formaldehyde. At present the most important resins of this group are the oil-soluble thermoplastics produced from formaldehyde and substituted phenols, such as those containing phenyl, tertiary butyl, and tertiary amyl groups in the para position. These resins find use in varnishes and other coating compounds, where they are characterized by their hardness, elasticity, and resistance to exterior exposure. Thermoplastic resins formed by the acid condensation of formaldehyde and aniline are of importance because of their excellent electric resistance and low power factor. They are reddish-brown in color, have good structural strength, and are not appreciably affected by exposure to weather or ultraviolet light. They are used extensively for insulators and other electric equipment. Structurally they are stated to consist of the cyclic anhydroformaldehyde aniline, (CeH^NrCH^s, and products produced by nuclear linking of two or more molecules of this compound by means of methylene groups. Recent industrial interest in the thermoplastic resins produced from formaldehyde and aromatic hydrocarbons (pages 236-237) points to possible future development of these products, With the comparatively recent development of tough, transparent, thermoplastic synthetic resins, the industrial importance of resins of this type
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Formaldehyde Tank Cars. Courtesy B.
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Copyright, 1944, by REIXHOLD PUBLIS
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iv FORMALDEHYDE of the highest valu
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Introduction Formaldehyde chemistry
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Page o y GENERAL IxrRODrcTiON iii P
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Page CHAPTER IS. HEXAIIETHYLEXEIETR
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Early History of Formaldehyde FORMA
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FORMALDEHYDE Production of Formalde
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6 POEM ALDEHYDE 30-cm hard-glass tu
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_ 3, "Formaldehyde unit developed b
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10 FORMALDEHYDE hyde. A modern plan
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12 FORMALDEHYDE catalysts contain f
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14 FORMALDEHYDE decompose at temper
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18 FORMALDEHYDE comprising aluminum
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Chapter 2 Monomeric Formaldehyde Al
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20 FORMALDEHYDE u-av contain small
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22 FORMALDEHYDE turea from 25 to 12
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24 FORMALDEHYDE formaldehyde in ace
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2G FORMALDEHYDE polymerizes very sl
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Chapter 3 State of Dissolved Formal
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30 ' FORMALDEHYDE ethylene oxide wi
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32 FORMALDEHYDE cal equilibrium bet
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34 FORMALDEHYDE Skrabal and Leutner
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36 FORMALDEHYDE Equilibria of the f
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38 FORMALDEHYDE molecule is saturat
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40 FORMALDEHYDE develop measurable
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42 ' FORMALDEHYDE present in the mo
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44 FORMALDEHYDE formaldehyde (methy
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46 FORMALDEHYDE Toxicity: Physiolog
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Chapter 5 Physical Properties of Pu
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50 :H:O/J00 £. Solution 2.23 4.60
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50 FORMA UihlHYhi: by Natta. and Ba
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.32 FORMALDEHYDE Partial Pressure,
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54 FORMALDEHYDE Lacy 17 * has recen
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50 FORMALDEHYDE At temperatures bel
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Chapter 6 Distillation of Formaldeh
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60 FORMALDEHYDE and that the soluti
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62 FORMALDEHYDE was found to contai
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Chapter 7 Formaldehyde Polymers Pol
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60 FORMALDEHYDE true polyoxymethyle
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6S FORMALDEHYDE sodium sulfate, and
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70 FORMALDEHYDE formaldehyde soluti
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72 FORMALDEHYDE ance of a colorless
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74 FORMALDEHYDE centrationa the rea
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76 FORMALDEHYDE the vacuum concentr
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78 FORMALDEHYDE mately 0.1 to 0.3 p
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80 FORMALDEHYDE dehyde solution was
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S2 FORMALDEHYDE ingers studies of t
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Table .17, Proportion at "VidyaxymQ
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SB FORMALDEHYDE soluble solid diace
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ss FORMALDEHYDE gradually increases
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go FORMALDEHYDE sulfuric acid were
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92 FORMALDEHYDE molecules. This con
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94 FORMALDEHYDE temperature. Since
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96 FORMALDEHYDE are forming or evap
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9S FORMALDEHYDE of formaldehyde to
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100 FORMALDEHYDE sublimate in the f
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Chapter 8 ; Chemical Properties of
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104 FORMALDEHYDE modif}- the decomp
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106 FORMALDEHYDE Reactions of Forma
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IMS FORMALDEHYDE i-.n^ ;t!i a-i^-at
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Ha FORI! ALDEHYDE arid 'ii:„-":.;
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FORMALDEHYDE \V;:h a-motiii;, :orn^
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m FORMALDEHYDE Under anhydrous cond
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116 FORMALDEHYDE 34,1. G. Farbenind
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118 FORMALDEHYDE The effect of alka
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120 FORMALDEHYDE precipitates. Coll
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122 FORMALDEHYDE On heating solutio
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124 FORMALDEHYDE prepared it by gra
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126 FORMALDEHYDE By reaction of 960
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X2S FORMALDEHYDE On reaction of two
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130 FORMALDEHYDE methylene glycol d
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132 FORMALDEHYDE Although this acid
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134 FORMALDEHYDE evolved and carbon
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m FORMALDEHYDE References I. Anders
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Chapter 10 Reactions of Formaldehyd
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ttJSAUTiuivs WITH HYDROXY COMPOUNDS
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142 FORMALDEHYDE alcohol with forma
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144 FORMALDEHYDE that no stable con
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146 FORMALDEHYDE hydrogen halide, a
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148 FORMALDEHYDE Z, Backer, H. :..
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152 FORMALBEH YDE Pentaerythritol i
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] 54 FORMA LDEHYDB Pentaglyeerol ap
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lot; CH2OH),C-CHOH,Cf;CEtOH)8 FORMA
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15S FORM A L DEH YDE In the ease ox
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1,30 FORMALDEHYDE with cold concent
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104 FORMALDEHYDE indicated. rhi> re
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166 FORMALDEHYDE substituted phenol
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H3S FORMALDEHYDE The preparation an
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170 FORMALDEHYDE are slow to react
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172 FORMALDEHYDE produce methylene
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174 FORMALDEHYDE The ether, dimethy
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i7G FORMALDEHYDE ratios, as would b
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ITS FORMALDEHYDE ami it- polviiueU-
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ISO FORMALDEHYDE HO^ /> - CH-OCaq)
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1S2 FORMALDEHYDE On oxidation and h
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154 FORMALDEHYDE ghieinol itseli ar
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l&e H 0 T FORMALDEHYDE O il a c / ^
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1SS FORMALDEHYDE Phenols having thr
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190 FORMALDEHYDE 27. Eanus, F., J.
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192 FORMALDEHYDE Acids containing a
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194 FORMALDEHYDE reaction which tak
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190 FORMALDEHYDE era! hiji;rs. When
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19S FORMALDEHYDE By oxidation with
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200 FORMALDEHYDE cold reaction mixt
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202 FORMALDEHYDE In the case of eth
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204 FORMALDEHYDE *m \it.^:U:Z hi mt
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200 FORMALDEHYDE In av^îu:, -econd
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2QS FORMALDEHYDE Mixed methylene de
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•210 FORMALDEHYDE According to Ka
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12 FORMALDEHYDE Tho t>*.:y:;.*:'k-
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214 FORMALDEHYDE hy employing an ac
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2IM FORMA LDEH YDE In the presence
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21S FORMALDEHYDE On exposure TO dil
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220 FORMALDEHYDE •with 4 or more
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222 FORMALDEHYDE anism by which the
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224 FORMALDEHYDE H'iris \.\\i. :\j:
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220 FORMALDEHYDE 97. SeieiEer, E, T
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22S FORMALDEHYDE Since strongly aci
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230 FOEMALDBBYDE feolsble derivativ
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232 HOCHjCi - j V / u H H CH2C! FOR
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234 CHj CHa / \ FORMALDEHYDE CHs /
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2m FORMALDEHYDE extremely stringent
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23S FORMALDEHYDE silver aeervHde an
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24.0 FORMALDEHYDE alcohol*. Moureu
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242 FORMALDEHYDE Farbenindusnie pat
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Chapter 16 Detection and Estimation
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24ti FORMALDEHYDE iiiriue :'-r vrr.
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*>JS FOIOIALBEHYD, t-,TîKêd «JJ
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250 FORMALDEHYDE Beta-Naphthoi. Bet
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252 FORMALDEHYDE bridle compounds o
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254 FORMALDEHYDE 14. Dtoigts, G., C
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250 FORMALDEHYDE Formaldehyde may a
Page 271 and 272: 23S FORMALDEHYDE analyzed, but shou
Page 273 and 274: 2u0 FORMALDEHYDE by Roniijn :: . Th
Page 275 and 276: 262 FORMALDEHYDE The following modi
Page 277 and 278: 2-', I FORMALDEHYDE lleilione Is ^
Page 279 and 280: 26G FORMALDEHYDE should be neutral
Page 281 and 282: 2i kS FORMALDEHYDE previously m^-ur
Page 283 and 284: 270 FORMALDEHYDE tioii of ike metha
Page 285 and 286: 272 FORMALDEHYDE insoluble material
Page 287 and 288: 274 FORMALDEHYDE hyde liberated by
Page 289 and 290: Chapter 18 Hexamethylenetetramine H
Page 291 and 292: 27S FORMALDEHYDE show monobasic cha
Page 293 and 294: 2S0 FORMALDEH YDE Reactions I and I
Page 295 and 296: 2S2 FORMALDEHYDE 275"F 135 ; C/. By
Page 297 and 298: 2S4 FORMALDEHYDE On ignition, it bu
Page 299 and 300: 2S6 FORMALDEHYDE Physiological Prop
Page 301 and 302: 2SS FORMA LDEH YDE base or ?JV :he
Page 303 and 304: 290 FORMALDEHYDE Reaction* with Sul
Page 305 and 306: 292 FORMA LDEH1 'BE erately concent
Page 307 and 308: 294 FORMALDEHYDE acetone in boiling
Page 309 and 310: 296 FORMALDEHYDE for 15 minute* wit
Page 311 and 312: 298 FORMALDEHYDE approximately 0/2
Page 313 and 314: 300 FORMALDEHYDE 35. D^v-jkv. -T. V
Page 315 and 316: Chapter 19 Uses of Formaldehyde, Fo
Page 317 and 318: 304 ' FORMA LDEH YJj£ of both plan
Page 319 and 320: 306 FORMALDEHYDE ent, resistant to
Page 321: 305 FORMALDEHYDE Resins, joining wo
Page 325 and 326: 312 FORMA LB Ell 3 V D£ resin-like
Page 327 and 328: 314 FORMALDEHYDE For example, it is
Page 329 and 330: 316 FORMALDEHYDE ically involved in
Page 331 and 332: Chapter 20 Uses of Formaldehyde, Fo
Page 333 and 334: 320 FORMALDEHYDE 12-24 hours-. Some
Page 335 and 336: 322 FORMALDEHYDE has been utilized
Page 337 and 338: 324 FORMALDEHYDE References 1. Baue
Page 339 and 340: 326 FORMALDEHYDE soaking for four t
Page 341 and 342: 32S FORMALDEHYDE colors is among th
Page 343 and 344: 330 FORMALDEHYDE 7. Jones, H. I., !
Page 345 and 346: 332 FORMALDEHYDE Tetranifcthylenedi
Page 347 and 348: 334 FORMALDEHYDE 0. Rinser, F., :o
Page 349 and 350: 33(3 FORMA LDEHYDE low dishes or on
Page 351 and 352: 338 FORMALDEHYDE sistance and other
Page 353 and 354: 340 FORMALDEHYDE complUhed by deriv
Page 355 and 356: M2 FORMALDEHYDE is reported thai t'
Page 357 and 358: 344 FORMALDEHYDE References 1. Bore
Page 359 and 360: 341) FORMALDEHYDE distilled water a
Page 361 and 362: 34S FORMALDEHYDE high wet-strength
Page 363 and 364: 350 FORMALDEHYDE a roll, after whic
Page 365 and 366: 35*2 FORMA LDEH \ 'DK chloride "lit
Page 367 and 368: 354 FORMALDEHYDE forming developers
Page 369 and 370: 356 FORMALDEHYDE In addition, it is
Page 371 and 372: 35S FORMALDEHYDE An entirely differ
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360 FORMALDEHYDE According to Seymo
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362 FORMALDEHYDE improved by an aci
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364 FORMALDEHYDE type because the p
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366* FORMALDEHYDE spiration can be
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36S FORMALDEHYDE itatrng bath which
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370 FORMALDEHYDE 39. Lantz, L. A.,
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Abel, JM 1S1 Acres, S. F., 125 Adam
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Lacy, B. S.t 54 Ladisck, C, 215 Lae
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IB, 1, Itotaf,!,! Ifflt,0,S i,! ife
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Ammonia, reaction, of formaldehyde
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Cyclic polymers, 65; 94-100 Tetraox
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Hydrocarbon gases, production from,
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Polyeondensation of simple, 112 Rea
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Lower polyoxymethylene glycols, 67-
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Aromatic hydrocarbons, 231-237 Dlar
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Latex, 355-356 Synthetic, 358 Salic
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,- T7 Dyes, 327-329 Embalming, 329-
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No. 35. Noxious Gases. By Yandell H
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