NO119111B - - Google Patents
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- Publication number
- NO119111B NO119111B NO69068A NO69068A NO119111B NO 119111 B NO119111 B NO 119111B NO 69068 A NO69068 A NO 69068A NO 69068 A NO69068 A NO 69068A NO 119111 B NO119111 B NO 119111B
- Authority
- NO
- Norway
- Prior art keywords
- oxy
- dimethylbenzene
- phenol
- mixture
- xylenol
- Prior art date
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- 150000003739 xylenols Chemical class 0.000 claims description 33
- 229920005989 resin Polymers 0.000 claims description 26
- 239000011347 resin Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
- 230000001588 bifunctional effect Effects 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 6
- -1 1-oxy-2 Chemical class 0.000 claims description 5
- 150000003945 chlorohydrins Chemical class 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical class [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 4
- 238000000576 coating method Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000945 filler Substances 0.000 description 8
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 6
- 229930003836 cresol Natural products 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- XEPXTKKIWBPAEG-UHFFFAOYSA-N 1,1-dichloropropan-1-ol Chemical compound CCC(O)(Cl)Cl XEPXTKKIWBPAEG-UHFFFAOYSA-N 0.000 description 2
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- IFDLXKQSUOWIBO-UHFFFAOYSA-N 1,3-dichloropropan-1-ol Chemical compound OC(Cl)CCCl IFDLXKQSUOWIBO-UHFFFAOYSA-N 0.000 description 1
- RZWHKKIXMPLQEM-UHFFFAOYSA-N 1-chloropropan-1-ol Chemical compound CCC(O)Cl RZWHKKIXMPLQEM-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 101100219710 Mus musculus Cbarp gene Proteins 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910021383 artificial graphite Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- QZJVWTNHFOMVHX-UHFFFAOYSA-N methanol;methyl acetate Chemical compound OC.COC(C)=O QZJVWTNHFOMVHX-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910021382 natural graphite Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04B—GENERAL BUILDING CONSTRUCTIONS; WALLS, e.g. PARTITIONS; ROOFS; FLOORS; CEILINGS; INSULATION OR OTHER PROTECTION OF BUILDINGS
- E04B9/00—Ceilings; Construction of ceilings, e.g. false ceilings; Ceiling construction with regard to insulation
- E04B9/22—Connection of slabs, panels, sheets or the like to the supporting construction
- E04B9/24—Connection of slabs, panels, sheets or the like to the supporting construction with the slabs, panels, sheets or the like positioned on the upperside of, or held against the underside of the horizontal flanges of the supporting construction or accessory means connected thereto
- E04B9/247—Connection of slabs, panels, sheets or the like to the supporting construction with the slabs, panels, sheets or the like positioned on the upperside of, or held against the underside of the horizontal flanges of the supporting construction or accessory means connected thereto by means of sliding or pivoting locking elements, held against the underside of the supporting construction
Landscapes
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Connection Of Plates (AREA)
- Finishing Walls (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
Fremgangsmåte til fremstilling av herdbare kondensasjonsprodukter. Process for the production of curable condensation products.
Por fremstilling av fenoplast anvendes Por production of phenoplast is used
som råstoffer for det meste fenol og kresol, mens xylenol anvendes lite. Grunnen as raw materials mostly phenol and cresol, while xylenol is used little. Reason
til dette er at det xylenol som fåes teknisk to this is that it is xylenol that is obtained technically
er en blanding- av oksvdimetylbenzoler oe is a mixture of oxvdimethylbenzenes etc
en rekke andre fenolhomoloeer slik som a number of other phenol homologues such as
fenol, kresol, metvletvlfenol. etylfenol. r>ro-pvlfenol, isonronvifenol osv. hvis total-mengde i alminneliehet lierffer under 1 °f„. phenol, cresol, metvletvlphenol. ethyl phenol. r>ro-pvlphenol, isonronviphenol, etc. whose total amount in the general unit lies below 1 °f„.
Smrn<p->ns<p>tnineren av ri<p>nne blandine varie-rer alltid i ri ot, frvrVioM^t mpd oms<p>tningen Smrn<p->ns<p>tniner of ri<p>nne blandine always varies in ri ot, frvrVioM^t mpd turnover
med formaMebvri ikke er re<p>roduserbar.with formaMebvri is not reducible.
De seks isom<p>re oksvriirnptviben7nlpr The six isom<p>re oxvriirnptviben7nlpr
av hvilke fem inneholdes i teknisk vvlpnol of which five are contained in technical vvlpnol
i stirre mengder, mens l-oksv-5<>>.if-dimetvl-benzol barp er tilstede i underordnede in staring amounts, while l-oxv-5<>>.if-dimethyl-benzene barp is present in subordinate
meneder tilleirer, alt etter konstitusionen, perjury lurks, according to the constitution,
1.2. eller 3 mol formairiehvd pr. mol oksv-dimetvlbenzol i alkalisk miliri. Kondensa-sinnen av de enkelte xvlenolmolekvler fo-re<g>år ved sammenknvtnine av metvlolfor-bind<p>l^ene. Monofunksionelle forbindelser 1.2. or 3 mol formaiirehvd per moles of oxv-dimethylbenzene in alkaline miliri. Condensation of the individual xvlenol molecules is formed by the combination of the methylolfor bond<p>l^s. Monofunctional compounds
som bare tili<p>irer ett formaldehvdmnl<p>kvl which only requires one formal dehvdmnl<p>kvl
avhr^t<p>r harniksmolekvlenes vekst,, bifunk-sionelle b<p>fnrdrer veksten og trifunksio-nell<p> b<p>virker nettdannelse av de enkelte depends on the growth of the food molecules, bifunctional b<p>fnrders the growth and trifunctional<p> b<p>causes network formation of the individual
harniksmol<p>kvl<p>r. Monofnnksionell er 1-oksv-5.4-riimetvib<p>n7ol. trifunksjonell 1-oksy-3. 5-di-metvlbenzol.harniksmol<p>kvl<p>r. Monofunctional is 1-oxv-5.4-riimetvib<p>n7ol. trifunctional 1-oxy-3. 5-di-methylbenzene.
Dpt, ble nu funnet at man får flvtende Dpt, it was now found that one gets flvtende
h<p>rriba.re harDikser med særlig sode esen-skaner når man tu kondensasionen anvender en fenolblandine som inneholder bi-funkcinnelle enkiern<p>de. enverdifre fenoler h<p>rriba.re has Dikser with particularly sod esene scans when you use a phenol mixture containing bi-functional enkiern<p>de for the condensation. monovalent phenols
fortrinsvis av bifunksionelt xvlenol, og preferably of bifunctional xvlenol, and
dessuten 3n % til PO <fn l-oksv-3. 5-dimetvl-benzol og 5 til 25 % monofunksjonelt xyle- moreover 3n % to PO <fn l-oxv-3. 5-dimethyl-benzene and 5 to 25% monofunctional xyl-
nol, dvs. l-oksy-2, 4-dimetylbenzol og/eller l-oksy-2, 6-dimetylbenzol. Som bifunksjonelt fenol kan det foruten bifunksjonelt xylenol også være tilstede bifunksjonelt kresol, som er o- og/eller p-kresol. Et slikt innhold av bifunksjonelt kresol er av og til hensiktsmessig. Slik som det fremgår nol, i.e. 1-oxy-2,4-dimethylbenzene and/or 1-oxy-2,6-dimethylbenzene. As bifunctional phenol, in addition to bifunctional xylenol, bifunctional cresol, which is o- and/or p-cresol, can also be present. Such a content of bifunctional cresol is sometimes appropriate. As it appears
av det ovenstående utgjør mengden av of the above constitutes the quantity of
bifunksjonelt fenol i fenolblandinger som skal anvendes ifølge oppfinnelsen, mellom 5 og 65 %. Herved er de mindre i alminne-lighet under ialt 1 % liggende mengder av de ovenfor nevnte fenoler som inneholdes i teknisk xylenol inklusivt. En tilsetning av mindre mengder fenol (CbHo-OH) f. eks. bifunctional phenol in phenol mixtures to be used according to the invention, between 5 and 65%. Hereby, the amounts of the above-mentioned phenols that are contained in technical xylenol inclusive are generally below 1% in total. An addition of smaller amounts of phenol (CbHo-OH) e.g.
1—10 % er nok mulig, men bevirker i al-minnelighet ingen forbedring av egenska-pene. 1-10% is probably possible, but generally causes no improvement in the properties.
De xylenolblandinger som ifølge oppfinnelsen anvendes som utgangsstoff, lar seg kondensere på kjent måte med aldehyder, fortrinsvis formaldehyd. Hensiktsmessig anvender man herved et formaldehyd-fenol-forhold på 0,7 til 1,5, fortrinsvis fra 0,9 til 1,3. Det kan imidlertid også anvendes større eller mindre mengder formaldehyd. The xylenol mixtures which according to the invention are used as starting material can be condensed in a known manner with aldehydes, preferably formaldehyde. Appropriately, a formaldehyde-phenol ratio of 0.7 to 1.5, preferably from 0.9 to 1.3, is used here. However, larger or smaller amounts of formaldehyde can also be used.
I stedet for formaldehyd kan det også anvendes andre aldehyder slik som acetal-dehyd. De produkter som kan fåes av de harpikser som er fremstilt ifølge oppfinnelsen har en vesentlig større motstandsevne Instead of formaldehyde, other aldehydes such as acetal-dehyde can also be used. The products that can be obtained from the resins produced according to the invention have a significantly greater resistance
mot kjemiske innvirkninger enn produkter against chemical influences than products
som er fremstilt av monofunksjonelt xylenol, bifunksjonelt kresol og trifunksjonelt fenol (GoHdOH). De lar seg støpe i former og presse til formlegemer slik som beskre- which is made from monofunctional xylenol, bifunctional cresol and trifunctional phenol (GoHdOH). They can be molded into shapes and pressed into shaped bodies as described
vet for xylenolharpikser i fransk patent nr. 1 062 192. know for xylenol resins in French Patent No. 1,062,192.
Sammensetningen av en xylenol-blanding lar seg bestemme ved kombinasjon av en destillasjon og opptak av ultrarøde spektere av destillatet og resten. Ved ana-lytisk destillasjon skilles fenol og kreso-lene, idet en mindre del l-oksy-2, 4- og 1-oksy-2, 5-dimetylbenzol går med over. I resten befinner seg ved siden av l-oksy-2, 6-dimetylbenzol hovedmengden av 1-oksy-2, 4-dimetylbenzol og hele l-oksy-3, 5-dimetylbenzol, som ved hjelp av ultrarødt spekters kopi lar seg bestemme ved siden av hverandre. Vil man gi avkall på en slik adskillelse vil en bestemmelse av symmetrisk xylenol være umulig, da beliggenhe-ten av båndene fra fenol og m-kresol gjør en kvantitativ bestemmelse av det symme-triske metaxylenol umulig. Ved kvantitativ bestemmelse av begge xylenoler — nøyak-tigheten av de kjente metoder utgjør ± 2 % — er xylenolblandingen entydig karakterisert da de kjedeavbrytende og nett-dannende komponenter er bestemt. Innholdet av for nettdannelsen av harpiksmo-lekylene dvs. for en forbindelse av de enkelte kjeder med hverandre til forføyning-stående l-oksy-3, 5-dimetylbenzol, fåes fra differansen mellom den funne mengde av dette xylenol og innholdet av l-oksy-2, 6-dimetylbenzol og l-oksy-2, 4-dimetylbenzol. The composition of a xylenol mixture can be determined by combining a distillation and recording ultra-red spectra of the distillate and the residue. During analytical distillation, phenol and the cresols are separated, with a smaller portion of 1-oxy-2,4- and 1-oxy-2,5-dimethylbenzene passing through. In the remainder, next to l-oxy-2, 6-dimethylbenzene, the main amount of 1-oxy-2, 4-dimethylbenzene and all of l-oxy-3, 5-dimethylbenzene are found, which can be determined with the aid of an ultra-red spectrum copy by side of each other. If one waives such a separation, a determination of symmetrical xylenol will be impossible, as the location of the bands from phenol and m-cresol makes a quantitative determination of the symmetrical metaxylenol impossible. By quantitative determination of both xylenols — the accuracy of the known methods amounts to ± 2% — the xylenol mixture is unambiguously characterized as the chain-breaking and net-forming components are determined. The content of the network formation of the resin molecules, i.e. of a connection of the individual chains with each other to form l-oxy-3, 5-dimethylbenzene, is obtained from the difference between the amount of this xylenol found and the content of l-oxy- 2, 6-dimethylbenzene and l-oxy-2, 4-dimethylbenzene.
Harpiksen som er fremstilt ifølge oppfinnelsen kan herdes på kjent måte f. eks. ved varmeinnvirkning eller ved innvirk-ning av sure, nøytrale eller basiske herdemidler. The resin produced according to the invention can be cured in a known manner, e.g. by the influence of heat or by the influence of acidic, neutral or basic curing agents.
Harpiksen som er fremstilt ifølge oppfinnelsen lar seg herde til produkter med overordentlig gode egenskaper. Som ut-gangsprodukt for koldtherdnende harpikser anvendes ved arbeide ifølge oppfinnelsen, særlig fordelaktig xylenolblandinger med mer enn 50 % l-oksy-3, 5-dimetylbenzol og 5—25 % l-oksy-2, 4-dimetylbenzol og/eller l-oksy-2, 6-dimetylbenzol. Denne xylenol-blanding kan man få fra teknisk xylenol hvis innhold av l-oksy-3, 5-dimetylbenzol og l-oksy-2, 4-dimetylbenzol ble bestemt som beskrevet, og som ble tilsatt videre 3, 5-xylenol for innstilling av den ønskede mengde av dette stoff. Disse har-uikser anvendes med fordel overalt hvor man slik som ved syrebygning, trenger produkter som i forbindelse med egnede fyllmidler ved hjelp av kaldherdning oppnår en meget høy bestandighet mot alkaliske, sure og oksyderende påkjenninger. The resin produced according to the invention can be cured into products with extremely good properties. When working according to the invention, xylenol mixtures with more than 50% l-oxy-3,5-dimethylbenzene and 5-25% l-oxy-2,4-dimethylbenzene and/or l-oxy -2, 6-Dimethylbenzene. This xylenol mixture can be obtained from technical xylenol whose content of l-oxy-3,5-dimethylbenzene and l-oxy-2,4-dimethylbenzene was determined as described, and to which 3,5-xylenol was further added to set the desired amount of this substance. These har-uiks are advantageously used wherever, as with acid building, products are needed which, in conjunction with suitable fillers, achieve a very high resistance to alkaline, acidic and oxidizing stresses by means of cold curing.
Trenger man harpikser som skal tiene som bindemiddel f. eks. ved fremstilling Do you need resins that are to be used as a binder, e.g. during manufacture
av bygningselementer ifølge den normale press- eller strengpressfremgangsmåten, viser det seg som meget fordelaktig når man anvender xylenoler som råstoffer som innenfor det ovenfor nevnte området, opp-viser et lavest mulig innhold av l-oksy-3, 5-dimetylbenzol som er nettopp tilstrekkelig for nettdannelse. Herved nedsettes herd-ningshastigheten og forarbeidbarheten set-tes opp uten at den kjemiske bestandighet blir mindre. F. eks. anvender man for kondensasjon av slike produkter xylenolblandinger som inneholder under 50 % 1-oksy-3, 5-dimetylbenzol og 5—25 % l-oksy-2, 4-dimetylbenzol og/eller l-oksy-2, 6-dimetylbenzol. of building elements according to the normal pressing or string pressing method, it proves to be very advantageous when using xylenols as raw materials which, within the above-mentioned range, have the lowest possible content of l-oxy-3, 5-dimethylbenzene which is just sufficient for network formation. In this way, the curing speed is reduced and the processability is increased without reducing the chemical resistance. For example for the condensation of such products, xylenol mixtures containing less than 50% 1-oxy-3,5-dimethylbenzene and 5-25% l-oxy-2,4-dimethylbenzene and/or l-oxy-2,6-dimethylbenzene are used.
Det var meget overraskende at de teknisk sett meget brukbare xylenol-formaldehyd-kondensasjonsprodukter lar seg fremstille av xylenoler med et slikt høyt innhold av monofunksjonelt xylenol, idet det som nevnt ved innstilling av mengde-forholdene av de ovenfor beskrevne xylenoler, lar seg fremstille ved reproduserbare kondensater med forskjellig forhold. Selv-følgelig lar også (som det fremgår av eksempel 1 og 2) forkondensatet seg fremstille som i en videre reaksjon kan etter-kondenseres. It was very surprising that the technically very useful xylenol-formaldehyde condensation products can be produced from xylenols with such a high content of monofunctional xylenol, since, as mentioned, by setting the quantity ratios of the xylenols described above, it can be produced by reproducible condensates with different ratios. Of course (as can be seen from examples 1 and 2) the pre-condensate can also be produced which can be post-condensed in a further reaction.
Harpikser som er fremstilt ifølge oppfinnelsen kan forarbeides med kjente til-setningsstoffer til masser som er meget motstandsdyktige mot kjemiske innvirkninger. F. eks. kan man tilsette kjente sure, nøytrale eller basiske herdemidler slik som 1, 5-naftalin-disulfonsyre, p-toluol-sulfonsyre, p-toluolsulfoklorid, maleinsyre-anhydrid, klorvannstoff, fosforsyre, svovel-syre, benzotriklorid, blyoksyd osv. i kjente mengder, hensiktsmessig mellom 0,5 og 5 % beregnet på fenolaldehydharpiksen. Videre kan man tilsette disse harpikser stoffer som forbedrer den kjemiske motstandsevne. Som slike kommer de kjente forbindelser på tale, slike som klorerte surstoff-holdige organiske forbindelser slike som klorhydriner eller klorerte aldehyder f. eks. 1, 2- eller 1, 3-diklorpropanol, monoklor-propanol, glykolklorhydrin, epiklorhydrin, diklor-tert.-isobutanol, klorhydrat, |3-di-klorpropionaldehydhydrat eller klorbenzal-dehyd. Det kan også eventuelt anvendes klorholdige fenoksyforbindelser, slik som de fåes på kjent måte ved opphetning av enverdige fenoler slik som fenol (Cp,HsOH), kresol, naftol eller xylenol med klorhydriner slik som diklorpropanol eller de andre nevnte korhydriner i alkalisk medium. Det kan videre også anvendes fosforsyreestere med inntil 6 C-atomer slik som trimetyl-fosfat og trietylfosfat samt vilkårlige blandinger av de nevnte stoffer som forbedrer den kjemiske motstandsevne. Mengden av alle disse stoffer kan utgjøre mellom 1 og 20 %, fortrinsvis mellom 3 og 15 % beregnet på formaldehydharpiksen, men kan og-så være større eller mindre f. eks. 30 %. Det er videre særlig fordelaktig å tilsette furfurol i mengder på mellom 1 og 30 % beregnet på fenol-aldehydharpiks. Særlig fordelaktige er blandinger av furfurol med klorhydriner og/eller klorerte alifatiske aldehyder og/eller eventuelt klorholdige, fenoksyforbindelser. Anvender man imidlertid slike blandinger, anbefales det ikke å anvende over 40 % beregnet på vekten av fenol-aldehydharpikser. Resins produced according to the invention can be processed with known additives into masses which are highly resistant to chemical influences. For example known acidic, neutral or basic hardeners such as 1, 5-naphthalene disulfonic acid, p-toluene sulfonic acid, p-toluene sulfochloride, maleic anhydride, hydrogen chloride, phosphoric acid, sulfuric acid, benzotrichloride, lead oxide etc. can be added in known amounts , suitably between 0.5 and 5% calculated on the phenolaldehyde resin. Furthermore, substances can be added to these resins which improve the chemical resistance. As such, the known compounds come into question, such as chlorinated oxygen-containing organic compounds such as chlorohydrins or chlorinated aldehydes, e.g. 1, 2- or 1, 3-dichloropropanol, monochloropropanol, glycol chlorohydrin, epichlorohydrin, dichloro-tert-isobutanol, chloral hydrate, |3-di-chloropropionaldehyde hydrate or chlorobenzaldehyde. Chlorine-containing phenoxy compounds can also optionally be used, as they are obtained in a known manner by heating monovalent phenols such as phenol (Cp,HsOH), cresol, naphthol or xylenol with chlorohydrins such as dichloropropanol or the other chlorhydrins mentioned in an alkaline medium. It is also possible to use phosphoric acid esters with up to 6 C atoms such as trimethyl phosphate and triethyl phosphate as well as arbitrary mixtures of the aforementioned substances which improve the chemical resistance. The amount of all these substances can amount to between 1 and 20%, preferably between 3 and 15% calculated on the formaldehyde resin, but can also be greater or less, e.g. 30%. It is furthermore particularly advantageous to add furfurol in amounts of between 1 and 30% calculated on phenol-aldehyde resin. Mixtures of furfurol with chlorohydrins and/or chlorinated aliphatic aldehydes and/or optionally chlorine-containing phenoxy compounds are particularly advantageous. However, if such mixtures are used, it is not recommended to use more than 40% calculated on the weight of phenol-aldehyde resins.
Harpiksen ifølge oppfinnelsen kan videre tilsettes kjente fyllstoffer. Herved kan fyllstoffer av enhver art f. eks. inerte fyllmidler og særlig også slike med stor var-meledningsevne benyttes, slik som silicium, siliciumkarbid og de forskjellige grafit-arter slik som naturlig grafit eller fint pulverisert koks eller andre arter av kun-stig grafit. Som videre inerte fyllmidler kommer f. eks. også siliciumdioksyd som kvarts, titandioksyd, bariumsulfat osv. på tale. Det lar seg imidlertid også anvende andre fyllmidler slik som allerede herdede f enolaldehydkondensasj onsharpikser, polyvinylklorid, polytetrafluoretylen, polytri-fluorkloretylen eller delvis acetalisert polyvinylalkohol, dvs. slike acetaliserte forbindelser av polyvinylalkohol hvor 55—75 % av hydroksylgruppene er acetalisert. De maksimale mengder av fyllmidler som kan tilsettes massene som fåes ifølge oppfinnelsen, kan lett bestemmes av fagmannen. The resin according to the invention can further be added to known fillers. Hereby, fillers of any kind, e.g. inert fillers and especially also those with high thermal conductivity are used, such as silicon, silicon carbide and the various types of graphite such as natural graphite or finely powdered coke or other types of artificial graphite. As further inert fillers, e.g. also silicon dioxide such as quartz, titanium dioxide, barium sulphate etc. in speech. However, it is also possible to use other fillers such as already hardened phenolaldehyde condensation resins, polyvinyl chloride, polytetrafluoroethylene, polytrifluorochloroethylene or partially acetalized polyvinyl alcohol, i.e. such acetalized compounds of polyvinyl alcohol where 55-75% of the hydroxyl groups are acetalized. The maximum amounts of fillers that can be added to the masses obtained according to the invention can be easily determined by the person skilled in the art.
Man kan også forarbeide harpiksene som fåes ifølge oppfinnelsen, til emulsjo-ner. F. eks. kan man tilsette dem små mengder oppløsningsmidler og tilsetnings-stoffer slik som diklorpropanol og innføre dem i en vandig oppløsning av f. eks. polyvinylalkohol under god blanding. The resins obtained according to the invention can also be processed into emulsions. For example small amounts of solvents and additives such as dichloropropanol can be added to them and introduced into an aqueous solution of e.g. polyvinyl alcohol under good mixing.
Til slutt skal det henvises til at det i det amerikanske patent nr. 2 375 964 og det engelske patent nr. 467 234 er beskrevet fremstillingen av harpikser som på grunn av sin oljeoppløselighet skal finne anven-delse i malingssektoren fra blandinger av xylenoler av forskjellig reaktivitet. Kon-densasjonsføringen ved fremstillingen av harpikser som inneholder såvel mono-, bi- og tri-funksjonelle xylenoler er imidlertid i sammenligning med fremgangsmåten ifølge oppfinnelsen forskjellig, fordi ved fremgangsmåten ifølge de nevnte pa-tenter må kondensasjonen føres således at først de mindre reaksjonsdyktige xylenoler bringes til omsetning og først til slutt tilsettes de hurtigere og lettere reagerende xylenoler. Det dannes følgelig helt forskjellige produkter. Finally, it should be noted that in the American patent no. 2 375 964 and the English patent no. 467 234 the production of resins which, due to their oil solubility, will find use in the paint sector from mixtures of xylenols of different reactivity are described . The condensation process in the production of resins containing both mono-, bi- and tri-functional xylenols is, however, different in comparison with the method according to the invention, because in the method according to the mentioned patents, the condensation must be carried out in such a way that the less reactive xylenols are brought first to turnover and only finally are the faster and easier reacting xylenols added. Consequently, completely different products are formed.
Eksempel 1: Example 1:
800 vektsdeler xylenol med et innhold av 55 % trifunksjonell xylenol og 20 % l-oksy-2, 4-dimetylbenzol, 880 vektsdeler formaldehyd (30 %ig) og 190 vektsdeler natronlut (33 %ig) omrøres 24 timer ved 30°, deretter innstilles med saltsyre under omrøring til en pH-verdi på ca. 3,5 og temperaturen holdes under 40°. Etter 30 minutters syrebehandling befris harpiksen fra syren, vaskes ut og vannet skilles fra. 800 parts by weight of xylenol with a content of 55% trifunctional xylenol and 20% l-oxy-2, 4-dimethylbenzene, 880 parts by weight of formaldehyde (30%) and 190 parts by weight of caustic soda (33%) are stirred for 24 hours at 30°, then set with hydrochloric acid while stirring to a pH value of approx. 3.5 and the temperature is kept below 40°. After 30 minutes of acid treatment, the resin is freed from the acid, washed out and the water separated.
Eksempel 2: Example 2:
800 vektsdeler teknisk xylenol med et innhold av 40 % symmetrisk xylenol og 23 % l-oksy-2, 4-dimetylbenzol, 800 vektsdeler formaldehyd (30 %ig) og 190 vektsdeler natronlut (33 %ig) kondenseres som angitt i eksempel 1, og harpiksen isoleres. 800 parts by weight of technical xylenol with a content of 40% symmetrical xylenol and 23% l-oxy-2,4-dimethylbenzene, 800 parts by weight of formaldehyde (30%) and 190 parts by weight of caustic soda (33%) are condensed as indicated in Example 1, and the resin is isolated.
Noen muligheter til videre forarbei-delse angis i følgende eksempler: Some possibilities for further processing are indicated in the following examples:
Eksempel 3: Example 3:
90 vektsdeler av den ifølge eksempel 1 erholdte harpiks blandes med 10 vektsdeler klorbenzol. og 210 vektsdteler etylenklor-hydrin og røres ut med et fyllstoff som består av kvartsmel som er tilblandet 20 % polyvinylklorid f. eks. p-toluolsulfosyre eller andre liknende virkende kjente stoffer som herdemiddel til en masse av mør-telliknende konsistens. Disse prøvelegemer viser etter fullstendig gjennomherdning meget god bestandighet mot alkalier, syrer og oksydasjonsmidler slik som salpetersyre eller blekelut. Ved 8 timers koking med 15 %'s natronlut, 15 %ig salpetersyre eller en blanding av etylalkohol + aceton = 1:1, ligger vektstapene under 5 %. 90 parts by weight of the resin obtained according to example 1 are mixed with 10 parts by weight of chlorobenzene. and 210 parts by weight of ethylene chlorohydrin and stirred in with a filler consisting of quartz flour mixed with 20% polyvinyl chloride, e.g. p-toluenesulfonic acid or other substances known to act similarly as a hardener to a mass of mortar-like consistency. After complete curing, these specimens show very good resistance to alkalis, acids and oxidizing agents such as nitric acid or bleach. When boiled for 8 hours with 15% caustic soda, 15% nitric acid or a mixture of ethyl alcohol + acetone = 1:1, the weight loss is below 5%.
Anvender man for prøvelegemene en harpiks til hvis fremstilling det ble anvendt en xylenol med 20 % symmetrisk m-xylenol, 30 % l-oksy-2, 4-dimetylbenzol og 50 % bifunksjonelt xylenol er vektstapene ved kokning med de angitte midler delvis vesentlig høyere. Ved etylalkohol + aceton f. eks. ligger tapet ved 15—20 % av prøve-legemenes vekt. If a resin with 20% symmetrical m-xylenol, 30% l-oxy-2, 4-dimethylbenzene and 50% bifunctional xylenol is used for the preparation of which a xylenol was used, the weight losses during boiling with the specified agents are partly significantly higher. With ethyl alcohol + acetone, e.g. the loss is 15-20% of the test bodies' weight.
Eksempel 4: Example 4:
170 vektsdeler av den ifølge eksempel 1 erholdte harpiks, 14 vektsdeler metanol-metylacetatblanding (66/34), 7 vektsdeler epiklorhydrin og 82 vektsdeler 5 prosents 170 parts by weight of the resin obtained according to example 1, 14 parts by weight methanol-methyl acetate mixture (66/34), 7 parts by weight epichlorohydrin and 82 parts by weight 5 percent
polyvinylalkohol-oppløsning behandles med polyvinyl alcohol solution is treated with
en hurtigrører idet man tilsetter polyvinylalkohol-oppløsningen først. Den således a high-speed mixer, adding the polyvinyl alcohol solution first. The thus
erholdte emulsjon tilsettes ca. 10 % av en obtained emulsion is added approx. 10% of one
18—20 % saltsyre og strekkes ut på glass-plater. Emulsjonen viser etter 24—48 timers tørkning i luft uømfindtlighet mot 18-20% hydrochloric acid and spread out on glass plates. After 24-48 hours of drying in air, the emulsion shows insensitivity to
vann samt organiske oppløsningsmidler, water and organic solvents,
slik som metanol. such as methanol.
Eksempel 5: Example 5:
Man blander den i eksempel 2 erholdte harpiks med grafit omtrent i forholdet 1 : 2. Denne blanding lar seg utmerket godt The resin obtained in example 2 is mixed with graphite in a ratio of approximately 1:2. This mixture can be used very well
presse eller forarbeide i strengpresse. Det press or process in a string press. The
lille innhold av symmetrisk m-xylenol bevirker en lang forarbeidningsvarighet uten small content of symmetrical m-xylenol causes a long processing time without
at det derved ville forårsakes en dårligere that it would thereby cause a worse
kjemisk bestandighet etter utherdningen. chemical resistance after curing.
Anvender man for det her angitte formål Used for the purpose stated here
en harpiks ifølge eksempel 1, er forarbeids-tiden vesentlig kortere uten at det ville a resin according to example 1, the preparation time is significantly shorter without it wanting
oppnås en høyere kjemisk bestandighet. a higher chemical resistance is achieved.
Claims (6)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1071067A GB1158608A (en) | 1967-03-07 | 1967-03-07 | Improvements in Clips for Fixing Wall or Ceiling Panels in Position |
Publications (1)
Publication Number | Publication Date |
---|---|
NO119111B true NO119111B (en) | 1970-03-23 |
Family
ID=9972853
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO69068A NO119111B (en) | 1967-03-07 | 1968-02-26 |
Country Status (9)
Country | Link |
---|---|
BE (1) | BE711768A (en) |
CH (1) | CH470595A (en) |
DE (1) | DE1683654C3 (en) |
DK (1) | DK127737B (en) |
FR (1) | FR1554537A (en) |
GB (1) | GB1158608A (en) |
NL (1) | NL6802921A (en) |
NO (1) | NO119111B (en) |
SE (1) | SE319599B (en) |
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EP2453075B1 (en) * | 2010-11-12 | 2014-10-29 | Cuhadaroglu Metal Sanayi Ve Pazarlama Anonim Sirketi | Single module detachable, sliding assembly, aluminium sub-construction system for cladding materials such as glass, ceramic, etc. |
CN115992623B (en) * | 2023-03-22 | 2023-05-30 | 保定市建筑设计院有限公司 | Building sound insulation building board and installation method thereof |
-
1967
- 1967-03-07 GB GB1071067A patent/GB1158608A/en not_active Expired
-
1968
- 1968-02-26 NO NO69068A patent/NO119111B/no unknown
- 1968-02-28 DE DE19681683654 patent/DE1683654C3/en not_active Expired
- 1968-03-01 NL NL6802921A patent/NL6802921A/xx unknown
- 1968-03-04 FR FR1554537D patent/FR1554537A/fr not_active Expired
- 1968-03-05 CH CH323668A patent/CH470595A/en not_active IP Right Cessation
- 1968-03-06 DK DK91768A patent/DK127737B/en unknown
- 1968-03-06 BE BE711768D patent/BE711768A/xx unknown
- 1968-03-07 SE SE3010/68A patent/SE319599B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DE1683654B2 (en) | 1973-04-26 |
DK127737B (en) | 1973-12-24 |
GB1158608A (en) | 1969-07-16 |
SE319599B (en) | 1970-01-19 |
NL6802921A (en) | 1968-09-09 |
FR1554537A (en) | 1969-01-17 |
DE1683654C3 (en) | 1973-11-15 |
DE1683654A1 (en) | 1971-08-19 |
CH470595A (en) | 1969-03-31 |
BE711768A (en) | 1968-09-06 |
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