GB470181A - Manufacture and application of polyglycol ethers - Google Patents
Manufacture and application of polyglycol ethersInfo
- Publication number
- GB470181A GB470181A GB36072/35A GB3607235A GB470181A GB 470181 A GB470181 A GB 470181A GB 36072/35 A GB36072/35 A GB 36072/35A GB 3607235 A GB3607235 A GB 3607235A GB 470181 A GB470181 A GB 470181A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sodium
- soda
- treated
- chloride
- ethylene oxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920000151 polyglycol Polymers 0.000 title abstract 11
- 239000010695 polyglycol Substances 0.000 title abstract 11
- 150000002170 ethers Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000047 product Substances 0.000 abstract 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 13
- -1 hydroxyalkyl ether Chemical compound 0.000 abstract 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 12
- 125000004432 carbon atom Chemical group C* 0.000 abstract 11
- 238000005406 washing Methods 0.000 abstract 11
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 abstract 10
- 239000000203 mixture Substances 0.000 abstract 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 9
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 abstract 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 8
- 150000002576 ketones Chemical class 0.000 abstract 6
- 239000003921 oil Substances 0.000 abstract 6
- 235000019198 oils Nutrition 0.000 abstract 6
- NNAVBEAARXTLEG-UHFFFAOYSA-N 2-(10-methylundecyl)phenol Chemical class CC(C)CCCCCCCCCC1=CC=CC=C1O NNAVBEAARXTLEG-UHFFFAOYSA-N 0.000 abstract 5
- 239000003513 alkali Substances 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 4
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- 150000002430 hydrocarbons Chemical class 0.000 abstract 4
- 150000002440 hydroxy compounds Chemical group 0.000 abstract 4
- 238000006116 polymerization reaction Methods 0.000 abstract 4
- 229960001922 sodium perborate Drugs 0.000 abstract 4
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 abstract 4
- 239000007858 starting material Substances 0.000 abstract 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 3
- 239000002253 acid Chemical group 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- UDHMTPILEWBIQI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 UDHMTPILEWBIQI-UHFFFAOYSA-N 0.000 abstract 3
- 229920002678 cellulose Polymers 0.000 abstract 3
- 239000001913 cellulose Substances 0.000 abstract 3
- 239000007795 chemical reaction product Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000007859 condensation product Substances 0.000 abstract 3
- 239000003292 glue Substances 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000011734 sodium Substances 0.000 abstract 3
- 229910052708 sodium Inorganic materials 0.000 abstract 3
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 abstract 3
- 229940048086 sodium pyrophosphate Drugs 0.000 abstract 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 abstract 3
- 235000019818 tetrasodium diphosphate Nutrition 0.000 abstract 3
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 abstract 3
- 239000004753 textile Substances 0.000 abstract 3
- 210000002268 wool Anatomy 0.000 abstract 3
- IFABLCIRROMTAN-MDZDMXLPSA-N (e)-1-chlorooctadec-9-ene Chemical compound CCCCCCCC\C=C\CCCCCCCCCl IFABLCIRROMTAN-MDZDMXLPSA-N 0.000 abstract 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 abstract 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 abstract 2
- NFIDBGJMFKNGGQ-UHFFFAOYSA-N 2-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 abstract 2
- UZVAZDQMPUOHKP-UHFFFAOYSA-N 2-(7-methyloctyl)phenol Chemical compound CC(C)CCCCCCC1=CC=CC=C1O UZVAZDQMPUOHKP-UHFFFAOYSA-N 0.000 abstract 2
- TUGJCCNDSJKBGN-UHFFFAOYSA-N 2-methyl-3-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC(O)=C1C TUGJCCNDSJKBGN-UHFFFAOYSA-N 0.000 abstract 2
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 abstract 2
- 229910015900 BF3 Inorganic materials 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 2
- 229920000742 Cotton Polymers 0.000 abstract 2
- 108090000790 Enzymes Proteins 0.000 abstract 2
- 102000004190 Enzymes Human genes 0.000 abstract 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 239000004115 Sodium Silicate Substances 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 150000001491 aromatic compounds Chemical class 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000003518 caustics Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000001896 cresols Chemical class 0.000 abstract 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 238000004043 dyeing Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000005608 naphthenic acid group Chemical group 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003138 primary alcohols Chemical class 0.000 abstract 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000000344 soap Substances 0.000 abstract 2
- 229910052911 sodium silicate Inorganic materials 0.000 abstract 2
- 229940032158 sodium silicate Drugs 0.000 abstract 2
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 2
- 235000011152 sodium sulphate Nutrition 0.000 abstract 2
- AKTHLFYZKHPYBY-UHFFFAOYSA-M sodium;1-chloroethanesulfonate Chemical compound [Na+].CC(Cl)S([O-])(=O)=O AKTHLFYZKHPYBY-UHFFFAOYSA-M 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 239000011592 zinc chloride Substances 0.000 abstract 2
- 235000005074 zinc chloride Nutrition 0.000 abstract 2
- XXZAOMJCZBZKPV-WEDXCCLWSA-N (1r,3s,4r)-3-chloro-4,7,7-trimethylbicyclo[2.2.1]heptane Chemical compound C1C[C@@]2(C)[C@@H](Cl)C[C@@H]1C2(C)C XXZAOMJCZBZKPV-WEDXCCLWSA-N 0.000 abstract 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 abstract 1
- NADYESXYOSLAEQ-UHFFFAOYSA-N 1,6-dimethyl-5-(4-methylpentyl)cyclohexa-2,4-dien-1-ol Chemical class C(CCC(C)C)C=1C(C(C=CC1)(C)O)C NADYESXYOSLAEQ-UHFFFAOYSA-N 0.000 abstract 1
- QJFSPLBJWQWFBC-UHFFFAOYSA-N 1-(10-methylundecyl)cyclohexan-1-ol Chemical class C(CCCCCCCCC(C)C)C1(CCCCC1)O QJFSPLBJWQWFBC-UHFFFAOYSA-N 0.000 abstract 1
- VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical class CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 abstract 1
- CSPXBDVVOXOIHI-UHFFFAOYSA-N 1-chloro-10-methylundecane Chemical compound CC(C)CCCCCCCCCCl CSPXBDVVOXOIHI-UHFFFAOYSA-N 0.000 abstract 1
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 abstract 1
- STMRWVUTGPZZER-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)phenol Chemical class CC(C)CC1=CC=CC(O)=C1CC(C)C STMRWVUTGPZZER-UHFFFAOYSA-N 0.000 abstract 1
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 abstract 1
- LLIGXYDULHXBDJ-UHFFFAOYSA-N 2-(4-methylpentyl)phenol Chemical compound CC(C)CCCC1=CC=CC=C1O LLIGXYDULHXBDJ-UHFFFAOYSA-N 0.000 abstract 1
- QBKQCRBKDPOQEI-UHFFFAOYSA-N 2-(7-methyloctyl)benzene-1,3-diol Chemical class CC(C)CCCCCCC1=C(O)C=CC=C1O QBKQCRBKDPOQEI-UHFFFAOYSA-N 0.000 abstract 1
- ZDSCFBCGDDCJFZ-UHFFFAOYSA-N 2-(methylamino)ethanesulfonic acid;sodium Chemical compound [Na].CNCCS(O)(=O)=O ZDSCFBCGDDCJFZ-UHFFFAOYSA-N 0.000 abstract 1
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 abstract 1
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 abstract 1
- BOOKZSFWBCMEMD-UHFFFAOYSA-N 2-chloro-3-(6-methylheptyl)phenol Chemical class C(CCCCC(C)C)C=1C(=C(C=CC1)O)Cl BOOKZSFWBCMEMD-UHFFFAOYSA-N 0.000 abstract 1
- FDIPWBUDOCPIMH-UHFFFAOYSA-N 2-decylphenol Chemical compound CCCCCCCCCCC1=CC=CC=C1O FDIPWBUDOCPIMH-UHFFFAOYSA-N 0.000 abstract 1
- UUPLEDUDCGCPCY-UHFFFAOYSA-N 2-methyl-3-(2-methylpropyl)phenol Chemical class CC(C)CC1=CC=CC(O)=C1C UUPLEDUDCGCPCY-UHFFFAOYSA-N 0.000 abstract 1
- OYWARRKXAZPRQC-UHFFFAOYSA-N 2-methyl-3-(3-methylbutyl)phenol Chemical class C(CC(C)C)C1=C(C(=CC=C1)O)C OYWARRKXAZPRQC-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- WCRKLZYTQVZTMM-UHFFFAOYSA-N 2-octadecylphenol Chemical class CCCCCCCCCCCCCCCCCCC1=CC=CC=C1O WCRKLZYTQVZTMM-UHFFFAOYSA-N 0.000 abstract 1
- ATYUFZQNJIZDJQ-UHFFFAOYSA-N 3-cyclohexyl-2-methylphenol Chemical class CC1=C(O)C=CC=C1C1CCCCC1 ATYUFZQNJIZDJQ-UHFFFAOYSA-N 0.000 abstract 1
- HVXRCAWUNAOCTA-UHFFFAOYSA-N 4-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=C(O)C=C1 HVXRCAWUNAOCTA-UHFFFAOYSA-N 0.000 abstract 1
- MOMKYJPSVWEWPM-UHFFFAOYSA-N 4-(chloromethyl)-2-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=NC(CCl)=CS1 MOMKYJPSVWEWPM-UHFFFAOYSA-N 0.000 abstract 1
- HJSPWKGEPDZNLK-UHFFFAOYSA-N 4-benzylphenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1 HJSPWKGEPDZNLK-UHFFFAOYSA-N 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 241000283690 Bos taurus Species 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 1
- 108010009736 Protein Hydrolysates Proteins 0.000 abstract 1
- 108010077895 Sarcosine Proteins 0.000 abstract 1
- 239000004902 Softening Agent Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 241000779819 Syncarpia glomulifera Species 0.000 abstract 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 238000007792 addition Methods 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001398 aluminium Chemical class 0.000 abstract 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000007844 bleaching agent Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 abstract 1
- 229930006739 camphene Natural products 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000012084 conversion product Substances 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 abstract 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 abstract 1
- 235000011180 diphosphates Nutrition 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 229930004069 diterpene Natural products 0.000 abstract 1
- 125000000567 diterpene group Chemical group 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical class CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 150000002191 fatty alcohols Chemical class 0.000 abstract 1
- 238000005187 foaming Methods 0.000 abstract 1
- 239000004088 foaming agent Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003077 lignite Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 abstract 1
- 235000019341 magnesium sulphate Nutrition 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 229940055577 oleyl alcohol Drugs 0.000 abstract 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000004006 olive oil Substances 0.000 abstract 1
- 235000008390 olive oil Nutrition 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 150000007530 organic bases Chemical group 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 210000000496 pancreas Anatomy 0.000 abstract 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000001739 pinus spp. Substances 0.000 abstract 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 abstract 1
- 235000019353 potassium silicate Nutrition 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 238000007670 refining Methods 0.000 abstract 1
- 229960004889 salicylic acid Drugs 0.000 abstract 1
- 229940043230 sarcosine Drugs 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 235000017550 sodium carbonate Nutrition 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 1
- 235000019983 sodium metaphosphate Nutrition 0.000 abstract 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000011269 tar Substances 0.000 abstract 1
- 229940095068 tetradecene Drugs 0.000 abstract 1
- 229940036248 turpentine Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 abstract 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
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
- D06L1/12—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using aqueous solvents
Abstract
An aromatic hydroxy compound substituted in the nucleus by at least one hydrocarbon or acyl radicle of at least four carbon atoms, or a hydroaromatic hydroxy compound substituted in the nucleus by at least one hydrocarbon radicle (other than an aliphatic radicle) of at least four carbon atoms, is treated with one or more mols. of an a , b -alkylene oxide or a corresponding halogenhydrin, the term "a , b -alkylene oxide" meaning alkylene oxides in which the oxide oxygen atom is linked to adjacent carbon atoms of an alkylene residue but not necessarily to the ultimate and penultimate carbon atoms. Alternatively, an aromatic or hydroaromatic hydroxy compound substituted as above, or a hydroaromatic hydroxy compound substituted in the nucleus with at least one aliphatic hydrocarbon radicle of at least four carbon atoms, is treated in the form of its alkali compound with an a , b -halogen hydrin, the resulting hydroxyalkyl ether is converted into a halogenalkyl ether, e.g. by treatment with thionyl chloride, and the halogenalkyl ether is treated with a poly-a , b -glycol in the presence of caustic alkali. The aromatic hydroxy compounds used as starting materials are obtainable (a) by reaction of aromatic hydroxy compounds with olefines containing at least four carbon atoms, e.g. with isobutylene, diisobutylene, n-dodecylene, cyclohexene or comphene, or with olefine mixtures obtainable by dehydrating mixtures of primary alcohols containing 4--8 carbon atoms, produced from carbon monoxide and hydrogen, or with olefine mixtures obtainable by polymerization of lower olefines such as ethylene, propylene, isobutylene, or the olefines obtainable from the alcohols specified above, or (b) by condensing aromatic hydroxy compounds with halogenated compounds containing at least four carbon atoms, such as pinene hydrochloride, isobutyl chloride, halogenated natural or synthetic hydrocarbon oils, or halogenated fractions of brown-coal tar, the condensation being effected in the presence of any of the usual catalysts, e.g. aluminium chloride, zinc chloride, ferric chloride, activated aluminium, or zinc dust, or (c) by condensing aromatic hydroxy compounds in known manner with alcohols containing at least four carbon atoms, e.g. tertiary butyl alcohol, cyclohexanol, methylcyclohexanols, or primary alcohols of 4--8 carbon atoms produced from carbon monoxide and hydrogen; alkyl-substituted aromatic starting materials are also obtainable from the acyl-substituted aromatic hydroxy compounds by reduction of the carbonyl group, and the acyl-substituted aromatic compounds are themselves obtainable by esterifying aromatic hydroxy compounds with appropriate carboxylic acids and treating the esters with aluminium chloride, whereby molecular rearrangement to the corresponding ketones is effected; the hydroaromatic compounds used as starting materials are obtainable by catalytic reduction of the corresponding aromatic compounds. Specified starting materials are n-butylphenols, isobutyl - o - cresols, diisobutyl-phenols, isoamylcresols, isohexylxylenols, isooctylphenols, isooctyl-o-chlorophenols, isooctyl-b -naphthols, isononylresorcinols, n- and isododecylphenols, isododecylcyclohexanols, n-octadecylphenols, n - undecyl - p - oxyphenyl ketone, n-heptdecyl-p-oxyphenyl ketone, o- and p - benzylphenol, cyclohexyl - o - cresols, p-oxydiphenyl, p-oxyphenylcamphanes, and the condensation products of phenol or cresols with diterpenes. Specified alkylene oxides are ethylene oxide, 1 : 2-propylene oxide, 1 : 2- or 2 : 3-butylene oxide, butadiene dioxide, cyclohexene oxide, glycide and epichlorhydrin. The reaction of the alkylene oxides with the aromatic or hydroaromatic hydroxy compounds may be effected at 50--250 DEG C. in the presence of a catalyst consisting of a caustic alkali, an alkali alcoholate, a tertiary organic base, or an acid substance such as potassium bisulphate. The products may be after-treated with organic reagents capable of reacting with hydroxy groups, and particularly with polybasic organic acids or with halogenated carboxylic or sulphonic acids. The ethers or their conversion products, obtained as described above, are useful, particularly in the textile industry, as wetting, washing, dispersing, foaming and softening agents, and also in the dyeing industry as through-dyeing or levelling agents. The products may be used alone or with appropriate additions, particularly (a) aliphatic, hydroaromatic or aromatic sulphonic acids (particularly in the form of their water-soluble salts) such as sulphonation products of heavy benzene, solar oil, solvent naphtha or naphthalene, or condensation products of such sulphonation products containing methylene groups, alkyl groups or benzyl groups, or the sulphonation products of Edeleanu extract, naphthenes, or naphthenic acids, or the sulphonation products obtained in refining petroleum or benzine with sulphuric acid, or sulphonation products of the turkey red oil type, including sulphonates of fatty alcohols and the condensation products of fatty acids of high molecular weight with aliphatic or aromatic hydroxy- or aminosulphonic acids, (b) salts of fatty, resinic or naphthenic acids or of benzoic or phthalic acid, (c) reaction products of fatty acid chlorides with sarcosine, albumen hydrolysis products, aromatic aminocarboxylic acids, or tartaric or salicylic acid, (d) inorganic salts such as alkali meta- or pyrophosphates, sodium carbonate, waterglass, or sodium sulphate or chloride, and (e) bleaching agents. The following examples are given: (1) (a) an excess of ethylene oxide (6 mols. or more) is caused to act on p-isooctylphenol (from phenol and diisobutylene), or on a mixture of alkylphenols obtained from phenol and an isobutylene polymerization product containing di- and tri-isobutylene and other olefines, or on an isooctyl-o-cresol; (b) cotton goods are washed in a bath containing isooctyl-o-cresol polyglycol ether, sodium pyrophosphate, and sodium metaphosphate; (c) three washing baths for cotton containing, respectively, isooctylphenol polyglycol ether, a reaction product of oleyl chloride and an albumen hydrolysate, and both these substances together, are compared; (d) comparison is made also of three washing baths containing (a ) isooctylphenol polyglycol ether and soda, (b ) partly degraded glue and soda, and (g ) the components of both the other baths; (e) a washing agent for textiles contains isooctylphenol polyglycol ether, soda, and a product obtained by treating sodium cellulose with ethylene oxide and sodium chlorethanesulphonate; the washing effect is compared with that of a bath containing soap and soda; (f) solid washing compositions containing liquid isooctylphenol polyglycol ether are obtained by mixing the latter with soda and a product obtained from sodium cellulose, ethylene oxide and sodium chlorethanesulphonate; glue or degraded glue may be used in place of the cellulose derivative, and the soda may be replaced or supplemented by sodium perborate, sodium bicarbonate or a mixture of sodium peroxide and a bicarbonate (g) comparison is made of four washing baths containing (a ) soap, soda, sodium perborate, sodium pyrophosphate, and sodium silicate, (b ) isooctylphenol polyglycol ether, sodium butylnaphthalenesulphonate, soda, sodium pyrophosphate, sodium silicate, sodium perborate, magnesium sulphate, and sodium sulphate, (g ) as under (b ), but containing a reaction product of oleyl chloride with sodium oxyethanesulphonate or with sodium methyltaurine in place of sodium butylnaphthalene-sulphonate, (d ) as under (b ), but containing the sodium salt of oleyl alcohol sulphuric ester in place of sodium butylnaphthalenesulphonate; (h) a washing composition contains isooctylphenol polyglycol ether, cattle pancreas and soda; other enzymes may replace the pancreatic enzymes; (i) washing compositions for textiles soiled with oil contain isooctylphenol polyglycol ether, a solvent such as turpentine, butanol or amyl alcohol, and water. (2) (a) Isododecylphenol is treated with an excess of ethylene oxide; the isododecylphenol may be obtained by condensing phenol with a propylene polymerization product consisting mainly of hydrocarbons of twelve carbon atoms, or by treating phenol with isododecyl chloride (prepared by chlorinating a light oil fraction containing dodecanes) in the presence of aluminium chloride; (b) ethylene oxide is caused to act on an alkylated cresol mixture obtained by treating crude cresol, in the presence of zinc chloride or aluminium chloride, with a monochlorinated middle oil fraction boiling at 160--220 DEG C.; (c) laundry goods are soaked in a bath containing soda and an isododecylphenol polyglycol ether; they are then rinsed, and boiled in a bath containing soda, sodium perborate, and isododecylphenol polyglycol ether. (3) Isohexylphenol is treated with ethylene oxide; a bath containing the product and soda is used for washing wool greased with olive oil. (4) Heptadecenyl-p-oxyphenyl ketone or undecyl-p-oxyphenyl ketone is treated with ethylene oxide; a bath containing soda and the product from undecyl-p-oxyphenyl ketone is used for washing wool. (5) Isobutylphenol is treated with ethylene oxide; a mixture of the product with xylenol is added as a wetting agent to a mercerizing lye. (6) Decylphenol (from crude decyl chloride and phenol) is treated with ethylene oxide. (7) Isononylphenol is treated with ethylene oxide; a dispersion of the product may be used for greasing wool; the isononylphenol is obtained by condensing phenol with a propylene polymerization product consisting of isononylenes. (8) Tetradecylphenol is treated with ethylene oxide, and the product is optionally treated with a halogenated carboxylic acid; the tetradecylphenol is obtained by treating phenol with tetradecene in the presence of boron fluoride. (9) Phenol is treated, in the presence of boron fluoride,
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB36072/35A GB470181A (en) | 1935-12-31 | 1935-12-31 | Manufacture and application of polyglycol ethers |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB36072/35A GB470181A (en) | 1935-12-31 | 1935-12-31 | Manufacture and application of polyglycol ethers |
Publications (1)
Publication Number | Publication Date |
---|---|
GB470181A true GB470181A (en) | 1937-08-03 |
Family
ID=10384630
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB36072/35A Expired GB470181A (en) | 1935-12-31 | 1935-12-31 | Manufacture and application of polyglycol ethers |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB470181A (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2428235A (en) * | 1942-10-19 | 1947-09-30 | Shell Dev | Production of aromatic hydroxy ethers |
US2493486A (en) * | 1946-04-10 | 1950-01-03 | Devoe & Raynolds Co | Tall oil esters |
US2504518A (en) * | 1946-05-02 | 1950-04-18 | Devoe & Raynolds Co | Synthetic drying compositions |
US2576913A (en) * | 1945-12-05 | 1951-12-04 | Ici Ltd | Detergent compositions |
US2653972A (en) * | 1950-06-09 | 1953-09-29 | Wyandotte Chemicals Corp | Process of producing lower alkyl-, carboxymethyl-, diethers of polyoxyalkylene glycols |
US2696498A (en) * | 1951-02-07 | 1954-12-07 | Gen Aniline & Film Corp | Process of preparing (beta halo alkoxy) benzoic acid |
US2740814A (en) * | 1952-01-17 | 1956-04-03 | Gen Aniline & Film Corp | Long chain alkyl-benzenesulfonamido-alkanol ethers |
US2745857A (en) * | 1952-02-23 | 1956-05-15 | Dow Chemical Co | Glycolic acid ethers of polyoxypropylene compounds and method of preparation |
US2768141A (en) * | 1952-10-24 | 1956-10-23 | Union Carbide & Carbon Corp | Noninflammable hydraulic fluids |
US2791567A (en) * | 1952-04-25 | 1957-05-07 | Shell Dev | Rubber latex compositions and the manufacture of articles therefrom |
US2801972A (en) * | 1952-12-01 | 1957-08-06 | Exxon Research Engineering Co | Manufacture of lubricating greases by alkali fusion of ether alcohols |
US2809122A (en) * | 1954-06-24 | 1957-10-08 | Sherwin Williams Co | Dual purpose tinting base |
US2839568A (en) * | 1954-06-29 | 1958-06-17 | Universal Oil Prod Co | Surface active polyethylene and polypropylene imine nu-aryl carbamates |
US2902385A (en) * | 1955-08-23 | 1959-09-01 | Bayer Ag | Process for the manufacture of finely dispersed water-insoluble dyestuff pastes |
US3006872A (en) * | 1957-10-28 | 1961-10-31 | Union Carbide Corp | Coagulation of dispersed polymeric organic material with poly(ethylene oxide), and product thereof |
-
1935
- 1935-12-31 GB GB36072/35A patent/GB470181A/en not_active Expired
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2428235A (en) * | 1942-10-19 | 1947-09-30 | Shell Dev | Production of aromatic hydroxy ethers |
US2576913A (en) * | 1945-12-05 | 1951-12-04 | Ici Ltd | Detergent compositions |
US2493486A (en) * | 1946-04-10 | 1950-01-03 | Devoe & Raynolds Co | Tall oil esters |
US2504518A (en) * | 1946-05-02 | 1950-04-18 | Devoe & Raynolds Co | Synthetic drying compositions |
US2653972A (en) * | 1950-06-09 | 1953-09-29 | Wyandotte Chemicals Corp | Process of producing lower alkyl-, carboxymethyl-, diethers of polyoxyalkylene glycols |
US2696498A (en) * | 1951-02-07 | 1954-12-07 | Gen Aniline & Film Corp | Process of preparing (beta halo alkoxy) benzoic acid |
US2740814A (en) * | 1952-01-17 | 1956-04-03 | Gen Aniline & Film Corp | Long chain alkyl-benzenesulfonamido-alkanol ethers |
US2745857A (en) * | 1952-02-23 | 1956-05-15 | Dow Chemical Co | Glycolic acid ethers of polyoxypropylene compounds and method of preparation |
US2791567A (en) * | 1952-04-25 | 1957-05-07 | Shell Dev | Rubber latex compositions and the manufacture of articles therefrom |
US2768141A (en) * | 1952-10-24 | 1956-10-23 | Union Carbide & Carbon Corp | Noninflammable hydraulic fluids |
US2801972A (en) * | 1952-12-01 | 1957-08-06 | Exxon Research Engineering Co | Manufacture of lubricating greases by alkali fusion of ether alcohols |
US2809122A (en) * | 1954-06-24 | 1957-10-08 | Sherwin Williams Co | Dual purpose tinting base |
US2839568A (en) * | 1954-06-29 | 1958-06-17 | Universal Oil Prod Co | Surface active polyethylene and polypropylene imine nu-aryl carbamates |
US2902385A (en) * | 1955-08-23 | 1959-09-01 | Bayer Ag | Process for the manufacture of finely dispersed water-insoluble dyestuff pastes |
US3006872A (en) * | 1957-10-28 | 1961-10-31 | Union Carbide Corp | Coagulation of dispersed polymeric organic material with poly(ethylene oxide), and product thereof |
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