CS244913B2 - Thermostabile hydrophilic condensating products of aldehydes and ketones with content of acid groups - Google Patents
Thermostabile hydrophilic condensating products of aldehydes and ketones with content of acid groups Download PDFInfo
- Publication number
- CS244913B2 CS244913B2 CS827650A CS765082A CS244913B2 CS 244913 B2 CS244913 B2 CS 244913B2 CS 827650 A CS827650 A CS 827650A CS 765082 A CS765082 A CS 765082A CS 244913 B2 CS244913 B2 CS 244913B2
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- CS
- Czechoslovakia
- Prior art keywords
- weight
- parts
- acid
- solution
- ketones
- Prior art date
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- 150000002576 ketones Chemical class 0.000 title claims description 46
- 150000001299 aldehydes Chemical class 0.000 title claims description 44
- 239000002253 acid Substances 0.000 title claims description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 81
- 239000007859 condensation product Substances 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 30
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 17
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 11
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 10
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 8
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 8
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 8
- 229960003080 taurine Drugs 0.000 claims description 5
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 claims description 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 4
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 claims description 4
- 229920002866 paraformaldehyde Polymers 0.000 claims description 4
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 4
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 90
- 239000000243 solution Substances 0.000 description 50
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 34
- 239000007787 solid Substances 0.000 description 31
- 239000000047 product Substances 0.000 description 27
- 235000010265 sodium sulphite Nutrition 0.000 description 17
- 239000004568 cement Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- -1 acetalaldehyde Natural products 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- 230000002378 acidificating effect Effects 0.000 description 12
- 239000000654 additive Substances 0.000 description 12
- 239000008098 formaldehyde solution Substances 0.000 description 12
- 239000010440 gypsum Substances 0.000 description 11
- 229910052602 gypsum Inorganic materials 0.000 description 11
- 239000011381 foam concrete Substances 0.000 description 10
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 10
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000004567 concrete Substances 0.000 description 8
- 238000005187 foaming Methods 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 239000004570 mortar (masonry) Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000011398 Portland cement Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229940015043 glyoxal Drugs 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 4
- 239000000920 calcium hydroxide Substances 0.000 description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000006193 liquid solution Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229960002449 glycine Drugs 0.000 description 3
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- VSVCAMGKPRPGQR-UHFFFAOYSA-N propan-2-one;sulfurous acid Chemical compound CC(C)=O.OS(O)=O VSVCAMGKPRPGQR-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 101100334117 Caenorhabditis elegans fah-1 gene Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 description 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- HXFCUMCLVYNZDM-UHFFFAOYSA-N 2-aminoacetic acid;sodium Chemical compound [Na].NCC(O)=O HXFCUMCLVYNZDM-UHFFFAOYSA-N 0.000 description 1
- OXGJKCALURPRCN-UHFFFAOYSA-N 3-methoxypropanal Chemical compound COCCC=O OXGJKCALURPRCN-UHFFFAOYSA-N 0.000 description 1
- ACPXHHDRVABPNY-UHFFFAOYSA-N 4-acetylbenzenesulfonic acid Chemical compound CC(=O)C1=CC=C(S(O)(=O)=O)C=C1 ACPXHHDRVABPNY-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZKUKKYGSCMCFBF-UHFFFAOYSA-N [Ca].S(N)(O)(=O)=O Chemical compound [Ca].S(N)(O)(=O)=O ZKUKKYGSCMCFBF-UHFFFAOYSA-N 0.000 description 1
- 150000003998 acyclic ketones Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000011083 cement mortar Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- YIBPLYRWHCQZEB-UHFFFAOYSA-N formaldehyde;propan-2-one Chemical compound O=C.CC(C)=O YIBPLYRWHCQZEB-UHFFFAOYSA-N 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- PUWCULQGLSPCMQ-UHFFFAOYSA-M sodium;4-acetylbenzenesulfonate Chemical compound [Na+].CC(=O)C1=CC=C(S([O-])(=O)=O)C=C1 PUWCULQGLSPCMQ-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/42—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/28—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C04B24/30—Condensation polymers of aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G6/00—Condensation polymers of aldehydes or ketones only
- C08G6/02—Condensation polymers of aldehydes or ketones only of aldehydes with ketones
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S507/00—Earth boring, well treating, and oil field chemistry
- Y10S507/935—Enhanced oil recovery
- Y10S507/936—Flooding the formation
- Y10S507/937—Flooding the formation with emulsion
- Y10S507/938—Flooding the formation with emulsion with microemulsion
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ceramic Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Structural Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Porous Artificial Stone Or Porous Ceramic Products (AREA)
- Chemical Treatment Of Metals (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Lubricants (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Cleaning Or Drying Semiconductors (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19813144673 DE3144673A1 (de) | 1981-11-10 | 1981-11-10 | Saeuregruppen enthaltende thermostabile, hydrophile kondensationsprodukte von aldehyden und ketonen |
Publications (2)
Publication Number | Publication Date |
---|---|
CS765082A2 CS765082A2 (en) | 1985-09-17 |
CS244913B2 true CS244913B2 (en) | 1986-08-14 |
Family
ID=6146063
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS827650A CS244913B2 (en) | 1981-11-10 | 1982-10-27 | Thermostabile hydrophilic condensating products of aldehydes and ketones with content of acid groups |
Country Status (26)
Country | Link |
---|---|
US (1) | US4657593A (ro) |
EP (1) | EP0078938B1 (ro) |
JP (1) | JPS5887111A (ro) |
KR (1) | KR890003001B1 (ro) |
AT (1) | ATE31323T1 (ro) |
AU (1) | AU543955B2 (ro) |
BR (1) | BR8206501A (ro) |
CA (1) | CA1188032A (ro) |
CS (1) | CS244913B2 (ro) |
DD (2) | DD211354A5 (ro) |
DE (2) | DE3144673A1 (ro) |
DK (1) | DK168541B1 (ro) |
DZ (1) | DZ474A1 (ro) |
EG (1) | EG15854A (ro) |
ES (1) | ES8307850A1 (ro) |
FI (1) | FI70585C (ro) |
GR (1) | GR76717B (ro) |
HU (1) | HU191364B (ro) |
NO (1) | NO158544C (ro) |
NZ (1) | NZ202287A (ro) |
PL (1) | PL137954B1 (ro) |
PT (1) | PT75711B (ro) |
RO (1) | RO85635B (ro) |
SG (1) | SG8088G (ro) |
YU (1) | YU42814B (ro) |
ZA (1) | ZA828041B (ro) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3344291A1 (de) * | 1983-12-07 | 1985-06-13 | Skw Trostberg Ag, 8223 Trostberg | Dispergiermittel fuer salzhaltige systeme |
DE3410820A1 (de) * | 1984-03-23 | 1985-10-03 | Skw Trostberg Ag, 8223 Trostberg | Zusatzmittel fuer beton und zementmoertel mit verlaengerter wirkungsdauer |
US4557763A (en) * | 1984-05-30 | 1985-12-10 | Halliburton Company | Dispersant and fluid loss additives for oil field cements |
DE3429068A1 (de) * | 1984-08-07 | 1986-02-20 | Skw Trostberg Ag, 8223 Trostberg | Metallverbindungen von saeuregruppen enthaltenden kondensationsprodukten oder co-kondensationsprodukten von ketonen und aldehyden |
ATE47707T1 (de) * | 1986-04-02 | 1989-11-15 | Sicotan Gmbh & Co Kg | Verfahren zum verfestigen von betonbauwerken und zum herstellen von moerteln, betonen oder hieraus bestehende produkte und ein hierfuer ausgebildeter zementleim. |
DE3825530A1 (de) * | 1987-08-07 | 1989-02-16 | Sueddeutsche Kalkstickstoff | Retentionsmittel fuer waessrige systeme |
US5089056A (en) * | 1989-04-21 | 1992-02-18 | Thiele Kaolin Company | Opacifying kaolin pigments and process for making same by reacting with sodium hydroxide in water |
US5203629A (en) | 1990-08-07 | 1993-04-20 | W.R. Grace & Co.-Conn. | Method for modifying concrete properties |
US5224774A (en) * | 1990-08-07 | 1993-07-06 | W. R. Grace & Co.-Conn. | Concrete additive product and method of use |
US5320851A (en) * | 1992-01-31 | 1994-06-14 | W. R. Grace & Co.-Conn. | Packaging and dispensing system for fluid and semi-fluid cement admixtures |
DE4217181A1 (de) * | 1992-05-23 | 1993-11-25 | Chemie Linz Deutschland | Verwendung von Kondensationsprodukten aus Melamin und Glyoxylsäure als Zusatzmittel für hydraulische Bindemittel und Baustoff |
DE4227417C1 (de) * | 1992-08-19 | 1993-12-09 | Holderchem Betec Gmbh | Hydraulisch abbindendes Injektionsmaterial für ringförmige Spalträume großer Länge |
US5290357A (en) * | 1992-12-22 | 1994-03-01 | Halliburton Company | Acetone/formaldehyde/cyanide resins |
US5346012A (en) * | 1993-02-01 | 1994-09-13 | Halliburton Company | Fine particle size cement compositions and methods |
US5358043A (en) * | 1993-03-22 | 1994-10-25 | Phillips Petroleum Company | Gelling compositions useful for oil field applications |
US5355955A (en) * | 1993-07-02 | 1994-10-18 | Halliburton Company | Cement set retarding additives, compositions and methods |
DE4325090C1 (de) * | 1993-07-27 | 1994-05-26 | Holderchem Betec Gmbh | Hydraulisch abbindendes Injektionsmaterial für ringförmige Spalträume großer Längen |
DE4421715A1 (de) | 1994-06-21 | 1996-01-04 | Sueddeutsche Kalkstickstoff | Verwendung von Pfropfpolymeren auf Basis von Keton-Aldehyd-Kondensations- bzw. Co-Kondensationsprodukten |
DE4434010C2 (de) * | 1994-09-23 | 2001-09-27 | Sueddeutsche Kalkstickstoff | Redispergierbare Polymerisatpulver, Verfahren zu deren Herstellung und Verwendung |
US5697458A (en) * | 1996-05-02 | 1997-12-16 | Carney; Leroy Lloyd | Drilling fluid process |
US5873936A (en) * | 1997-11-17 | 1999-02-23 | Maxxon Corp. | Cement composition self-leveling floor coating formulations and their method of use |
WO2013143705A1 (en) | 2012-03-30 | 2013-10-03 | Technische Universität München | Concrete admixtures |
EP2679613A1 (de) | 2012-06-26 | 2014-01-01 | Construction Research & Technology GmbH | Tonverträgliches Additiv für bauchemische Produkte |
EP2848597A1 (en) | 2013-09-17 | 2015-03-18 | Basf Se | Light-weight gypsum board with improved strength and method for making same |
US9359254B2 (en) | 2013-11-12 | 2016-06-07 | Baker Hughes Incorporated | Wellbore cement compositions and wellbore cementing methods |
DE102014203231A1 (de) * | 2014-02-24 | 2015-08-27 | Evonik Degussa Gmbh | Dispergierharze für Pigmentpräparationen mit geringem flüchtigem organischem Anteil |
US10221275B2 (en) | 2014-08-29 | 2019-03-05 | Sekisui Chemical Co., Ltd. | Furan resin, method for producing same, thermosetting furan resin composition, cured product, and furan resin composite |
JP6429181B2 (ja) * | 2014-09-11 | 2018-11-28 | 花王株式会社 | 縮合物の製造方法 |
WO2018091659A1 (en) | 2016-11-21 | 2018-05-24 | Basf Se | Composition for inorganic binders |
CA3117346A1 (en) | 2018-10-31 | 2020-05-07 | Basf Se | Enhanced dewatering of mining tailings employing chemical pre-treatment |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US841999A (en) * | 1906-03-20 | 1907-01-22 | Hoechst Ag | Process of making formaldehyde sulfoxylates. |
US2174127A (en) * | 1937-12-13 | 1939-09-26 | Du Pont | Sulphated acyloins and process of producing them |
US2432850A (en) * | 1941-05-02 | 1947-12-16 | Chem Ind Basel | Water-soluble condensation products and process of making same |
US2641591A (en) * | 1949-05-12 | 1953-06-09 | Dan River Mills Inc | Method of manufacturing acetoneformaldehyde condensation products |
CH303271A (de) * | 1949-10-14 | 1954-11-30 | Forestal Land Timber & Railway | Verfahren zur Herstellung harzartiger, wasserlöslicher Kondensationsprodukte aus Formaldehyd und Aceton. |
US2857433A (en) * | 1956-06-20 | 1958-10-21 | Olin Mathieson | Aromatic ketones and process of their production |
US3149152A (en) * | 1961-01-03 | 1964-09-15 | Ethicon Inc | Mono-alkali metal bisulfites of dialdehydes |
DE1720729A1 (de) * | 1967-10-17 | 1971-07-08 | Bayer Ag | Kondensationsprodukte |
FR1568994A (ro) * | 1968-03-19 | 1969-05-30 | ||
US3956140A (en) * | 1970-08-03 | 1976-05-11 | Dresser Industries, Inc. | Drilling fluids |
JPS5610327B2 (ro) * | 1973-06-04 | 1981-03-07 | ||
DE2542090C2 (de) * | 1975-09-20 | 1983-08-25 | Bayer Ag, 5090 Leverkusen | Kondensationsprodukte aus Cycloalkanonen, Formaldehyd und Alkalibisulfit |
FR2415084A1 (fr) * | 1978-01-20 | 1979-08-17 | Protex Manuf Prod Chimiq | Compositions additives pour melanges a base de ciments hydrauliques |
DE2831613C2 (de) * | 1978-07-19 | 1982-03-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Polykondensationsprodukten |
-
1981
- 1981-11-10 DE DE19813144673 patent/DE3144673A1/de not_active Ceased
-
1982
- 1982-10-07 DZ DZ826704A patent/DZ474A1/fr active
- 1982-10-14 GR GR69543A patent/GR76717B/el unknown
- 1982-10-15 AT AT82109565T patent/ATE31323T1/de not_active IP Right Cessation
- 1982-10-15 DE DE8282109565T patent/DE3277820D1/de not_active Expired
- 1982-10-15 EP EP82109565A patent/EP0078938B1/de not_active Expired
- 1982-10-21 PT PT75711A patent/PT75711B/pt not_active IP Right Cessation
- 1982-10-26 NZ NZ202287A patent/NZ202287A/en unknown
- 1982-10-27 CS CS827650A patent/CS244913B2/cs unknown
- 1982-10-28 CA CA000414356A patent/CA1188032A/en not_active Expired
- 1982-11-01 EG EG650/82A patent/EG15854A/xx active
- 1982-11-03 ZA ZA828041A patent/ZA828041B/xx unknown
- 1982-11-08 RO RO108993A patent/RO85635B/ro unknown
- 1982-11-08 YU YU2500/82A patent/YU42814B/xx unknown
- 1982-11-09 HU HU823599A patent/HU191364B/hu not_active IP Right Cessation
- 1982-11-09 NO NO823733A patent/NO158544C/no not_active IP Right Cessation
- 1982-11-09 KR KR8205062A patent/KR890003001B1/ko active
- 1982-11-09 BR BR8206501A patent/BR8206501A/pt unknown
- 1982-11-09 DD DD82255303A patent/DD211354A5/de not_active IP Right Cessation
- 1982-11-09 FI FI823840A patent/FI70585C/fi not_active IP Right Cessation
- 1982-11-09 DK DK499182A patent/DK168541B1/da not_active IP Right Cessation
- 1982-11-09 PL PL1982238945A patent/PL137954B1/pl unknown
- 1982-11-09 AU AU90271/82A patent/AU543955B2/en not_active Expired
- 1982-11-09 DD DD82244692A patent/DD208362A5/de not_active IP Right Cessation
- 1982-11-10 JP JP57196163A patent/JPS5887111A/ja active Granted
- 1982-11-10 ES ES517264A patent/ES8307850A1/es not_active Expired
-
1985
- 1985-07-15 US US06/755,224 patent/US4657593A/en not_active Expired - Lifetime
-
1988
- 1988-02-02 SG SG80/88A patent/SG8088G/en unknown
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