CA1071227A - Propylene oxide reaction products, process for their manufacture and their use - Google Patents
Propylene oxide reaction products, process for their manufacture and their useInfo
- Publication number
- CA1071227A CA1071227A CA249,513A CA249513A CA1071227A CA 1071227 A CA1071227 A CA 1071227A CA 249513 A CA249513 A CA 249513A CA 1071227 A CA1071227 A CA 1071227A
- Authority
- CA
- Canada
- Prior art keywords
- component
- propylene oxide
- moles
- carbon atoms
- reaction product
- 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
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 239000007795 chemical reaction product Substances 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims description 32
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 14
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 13
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract 6
- 125000005263 alkylenediamine group Chemical group 0.000 claims abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 48
- 238000004043 dyeing Methods 0.000 claims description 37
- 239000000047 product Substances 0.000 claims description 33
- 229920001223 polyethylene glycol Polymers 0.000 claims description 30
- 239000002202 Polyethylene glycol Substances 0.000 claims description 29
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 28
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 27
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 22
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 15
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 14
- 235000021355 Stearic acid Nutrition 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 9
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 9
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 9
- 239000008117 stearic acid Substances 0.000 claims description 9
- 235000021314 Palmitic acid Nutrition 0.000 claims description 7
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- 239000002657 fibrous material Substances 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 229940044600 maleic anhydride Drugs 0.000 claims 4
- 229940012831 stearyl alcohol Drugs 0.000 claims 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 229940113165 trimethylolpropane Drugs 0.000 claims 2
- 239000000306 component Substances 0.000 description 79
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 23
- 239000007859 condensation product Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 21
- 229940059574 pentaerithrityl Drugs 0.000 description 20
- 239000000975 dye Substances 0.000 description 19
- 239000004744 fabric Substances 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- 239000000839 emulsion Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 239000001993 wax Substances 0.000 description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 239000001117 sulphuric acid Substances 0.000 description 11
- 235000011149 sulphuric acid Nutrition 0.000 description 11
- 235000011187 glycerol Nutrition 0.000 description 10
- 229960005150 glycerol Drugs 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- -1 aromatic dicarboxylic acids Chemical class 0.000 description 9
- 239000004615 ingredient Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 239000004753 textile Substances 0.000 description 7
- 101001113483 Homo sapiens Poly [ADP-ribose] polymerase 1 Proteins 0.000 description 6
- 102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 description 6
- 230000000740 bleeding effect Effects 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- YBAGJSUAYPAYFG-MMALYQPHSA-N (3s,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione;ethane-1,2-diol Chemical compound OCCO.C[C@@H]1OC(=O)[C@H](C)OC1=O YBAGJSUAYPAYFG-MMALYQPHSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 239000001166 ammonium sulphate Substances 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 238000009981 jet dyeing Methods 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 229940012017 ethylenediamine Drugs 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000003977 halocarboxylic acids Chemical class 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 229960000443 hydrochloric acid Drugs 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-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
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 125000004079 stearyl 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])C([H])([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 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 description 1
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ATNNLHXCRAAGJS-QZQOTICOSA-N (e)-docos-2-enoic acid Chemical compound CCCCCCCCCCCCCCCCCCC\C=C\C(O)=O ATNNLHXCRAAGJS-QZQOTICOSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- WXBXVVIUZANZAU-UHFFFAOYSA-N 2E-decenoic acid Natural products CCCCCCCC=CC(O)=O WXBXVVIUZANZAU-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000842962 Apoda limacodes Species 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 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 description 1
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000001124 arachidoyl group Chemical group O=C([*])C([H])([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])C([H])([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])C([H])([H])[H] 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical class CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical class [H]C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000913 palmityl 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])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
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UKPBXIFLSVLDPA-UHFFFAOYSA-N propylhydrazine Chemical compound CCCNN UKPBXIFLSVLDPA-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- LIBWRRJGKWQFSD-UHFFFAOYSA-M sodium;2-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC=C1S([O-])(=O)=O LIBWRRJGKWQFSD-UHFFFAOYSA-M 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- WXBXVVIUZANZAU-CMDGGOBGSA-N trans-2-decenoic acid Chemical compound CCCCCCC\C=C\C(O)=O WXBXVVIUZANZAU-CMDGGOBGSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000010518 undesired secondary reaction Methods 0.000 description 1
- 238000009976 warp beam dyeing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2615—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
-
- 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
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
-
- 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
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Textile Engineering (AREA)
- Polyethers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH429375A CH598404B5 (en, 2012) | 1975-04-04 | 1975-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1071227A true CA1071227A (en) | 1980-02-05 |
Family
ID=4273391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA249,513A Expired CA1071227A (en) | 1975-04-04 | 1976-04-02 | Propylene oxide reaction products, process for their manufacture and their use |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US4055393A (en, 2012) |
| JP (2) | JPS51122020A (en, 2012) |
| BE (1) | BE840330A (en, 2012) |
| CA (1) | CA1071227A (en, 2012) |
| CH (2) | CH598404B5 (en, 2012) |
| DE (1) | DE2613755C2 (en, 2012) |
| DK (1) | DK155476A (en, 2012) |
| ES (1) | ES446677A1 (en, 2012) |
| FR (1) | FR2306230A1 (en, 2012) |
| GB (1) | GB1522091A (en, 2012) |
| NL (1) | NL182225C (en, 2012) |
| ZA (1) | ZA762008B (en, 2012) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH598404B5 (en, 2012) * | 1975-04-04 | 1978-04-28 | Ciba Geigy Ag | |
| LU76632A1 (en, 2012) * | 1977-01-24 | 1978-09-13 | ||
| LU76633A1 (en, 2012) * | 1977-01-24 | 1978-09-13 | ||
| GB1594596A (en) * | 1977-02-04 | 1981-07-30 | Prod Sandoz Sa | Textile teatment process and composition for use therein |
| DE2821494C2 (de) * | 1978-05-17 | 1983-04-28 | Bayer Ag, 5090 Leverkusen | Verfahren und Hilfsmittel zum Färben von Polyesterfasern oder diese enthaltenden Fasergemischen |
| EP0007737A1 (en) * | 1978-07-31 | 1980-02-06 | Atlas Chemical Industries (U.K.) Ltd | An aqueous solution containing a surfactant and its uses in emulsification |
| DE2839463A1 (de) * | 1978-09-11 | 1980-03-27 | Basf Ag | 1,3-bisarylglycerinaether und deren verwendung |
| CH624256GA3 (en, 2012) * | 1979-01-10 | 1981-07-31 | ||
| CH624257GA3 (en, 2012) * | 1979-01-10 | 1981-07-31 | ||
| FR2446350B1 (fr) * | 1979-01-11 | 1984-08-24 | Ciba Geigy Ag | Procede pour teindre des matieres cellulosiques textiles n'ayant pas ete nettoyees au prealable, preparation et produits utilises a cet effet, et matieres cellulosiques teintes par ce procede |
| DE2912497C3 (de) * | 1979-03-29 | 1982-04-15 | Hoechst Ag, 6000 Frankfurt | Verfahren und Mittel zum Colorieren von Textilien aus Polyesterfasern |
| DE3174788D1 (en) * | 1980-12-30 | 1986-07-10 | Ciba Geigy Ag | Process for dyeing or printing cellulosic materials and mixed cellulose/polyester fabrics |
| US4441885A (en) * | 1981-04-29 | 1984-04-10 | Ciba-Geigy Corporation | Anticrease finishing composition and use thereof in the dyeing or whitening of textile material which contains polyester fibres |
| USRE33291E (en) * | 1982-04-01 | 1990-08-07 | Basf Corporation | Process for the preparation of white graft polymer dispersions and flame-retardant polyurethane foams |
| US4550194A (en) * | 1982-04-01 | 1985-10-29 | Basf Wyandotte Corporation | Process for the preparation of polyether-ester polyols |
| US4494956A (en) * | 1982-12-14 | 1985-01-22 | Ciba-Geigy Corporation | Process for pad dyeing cellulosic textile materials |
| JPS59124922A (ja) * | 1982-12-31 | 1984-07-19 | Nippon Paint Co Ltd | 顔料分散用樹脂 |
| JPS61108781A (ja) * | 1984-10-31 | 1986-05-27 | 三洋化成工業株式会社 | ポリエステル系繊維用染色助剤 |
| MX2781A (es) * | 1985-06-27 | 1993-09-01 | Ciba Geigy Ag | Inhibidor de espuma para sistemas acuosos |
| US4705526A (en) * | 1985-07-18 | 1987-11-10 | Ciba-Geigy Corporation | Water-soluble or water-dispersible graft polymers and the preparation and use thereof |
| US5068395A (en) * | 1990-04-25 | 1991-11-26 | Amoco Corporation | Process for producing polymeric plasticizers from polyethylene terephthalate |
| US5583167A (en) * | 1993-06-30 | 1996-12-10 | Henkel Corporation | Curing agents for aqueous epoxy resins |
| US5565505A (en) * | 1993-06-30 | 1996-10-15 | Henkel Corporation | Self-dispersing curable epoxy resins, dispersions made therewith, and coating compositions made therefrom |
| US5604269A (en) * | 1993-12-27 | 1997-02-18 | Henkel Corporation | Self-dispersing curable epoxy resins, dispersions made therewith, and coating compositions made therefrom |
| JPH09507873A (ja) | 1993-12-27 | 1997-08-12 | ヘンケル コーポレーション | 自己分散型硬化性エポキシ樹脂と、それを伴って製造される分散液、およびそれから製造される塗料 |
| US5565506A (en) * | 1994-03-01 | 1996-10-15 | Henkel Corporation | Self-dispersing curable epoxy resins, dispersions made therewith, and coating compositions made therefrom |
| WO1996003452A1 (en) * | 1994-07-25 | 1996-02-08 | Henkel Corporation | Curing agents for aqueous epoxy resins |
| US5508373A (en) * | 1994-08-04 | 1996-04-16 | Henkel Corporation | Curing agents for epoxy resins based on 1,2-diaminocyclohexane |
| US5750595A (en) * | 1994-12-29 | 1998-05-12 | Henkel Corporation | Self-dispersing curable epoxy resin dispersions and coating compositions made therefrom |
| US5643976A (en) * | 1994-12-29 | 1997-07-01 | Henkel Corporation | Self-dispersing curable epoxy resin dispersions and coating compositions made therefrom |
| US5648409A (en) * | 1994-12-29 | 1997-07-15 | Henkel Corporation | Aqueous self-dispersible epoxy resin based on epoxy-amine adducts containing aromatic polyepoxide |
| WO1996020970A1 (en) * | 1994-12-29 | 1996-07-11 | Henkel Corporation | Aqueous self-dispersible epoxy resin based on epoxy-amine adducts |
| US5698476A (en) * | 1995-03-01 | 1997-12-16 | The Clorox Company | Laundry article for preventing dye carry-over and indicator therefor |
| US5719210A (en) * | 1996-11-26 | 1998-02-17 | Henkel Corporation | Self-dispersing curable epoxy resins, dispersions made therewith, and coating compositions made therefrom |
| US5961669A (en) * | 1998-03-12 | 1999-10-05 | Sybron Chemicals, Inc. | Acid donor process for dyeing polyamide fibers and textiles |
| KR20040011449A (ko) * | 2001-06-20 | 2004-02-05 | 마쓰모토유시세이야쿠 가부시키가이샤 | 폴리에스텔섬유의 올리고머 방지제 |
| US20120214892A1 (en) * | 2011-02-17 | 2012-08-23 | Basf Se | Process for producing polyesteretherols |
| CN104264481B (zh) * | 2014-09-23 | 2016-05-25 | 浙江皇马科技股份有限公司 | 一种高温耐碱渗透剂及其制备方法 |
| JP6566643B2 (ja) * | 2015-01-19 | 2019-08-28 | 株式会社Adeka | 容器および包装材 |
| CN107109072A (zh) * | 2015-01-19 | 2017-08-29 | 株式会社Adeka | 抗静电性树脂组合物以及使用了其的容器和包装材料 |
| JP6566647B2 (ja) * | 2015-01-26 | 2019-08-28 | 株式会社Adeka | 帯電防止性樹脂組成物ならびにこれを用いた容器および包装材 |
| DE102017213048A1 (de) | 2017-07-28 | 2019-01-31 | Gühring KG | Zerspanungswerkzeug |
| CN113038974B (zh) * | 2018-09-10 | 2022-11-08 | 阿克伦大学 | 用于3d印刷应用的星形聚(富马酸丙二醇酯)共聚物 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124602A (en) * | 1964-03-10 | Aliphatic esters of unsaturated | ||
| US1922459A (en) * | 1933-08-15 | Their production | ||
| US1970578A (en) | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
| US2002613A (en) | 1932-02-29 | 1935-05-28 | Gen Aniline Works Inc | Reaction product of an organic acid amide and an alkylene oxide |
| US2089569A (en) * | 1932-03-02 | 1937-08-10 | Gen Aniline Works Inc | Addition products of glycide to organic compounds |
| US2174760A (en) | 1934-04-19 | 1939-10-03 | Ig Farbenindustrie Ag | Condensation products derived from carboxylic acids and method of producing them |
| US2183853A (en) | 1934-12-22 | 1939-12-19 | Ig Farbenindustrie Ag | Polyoxyalkylene ether acid compounds containing a higher aliphatic group |
| US2427255A (en) | 1942-07-28 | 1947-09-09 | Hayden Chemical Corp | Artificial waxes comprising reaction products of maleic anhydride and partial esters of stearic acid and polyhydric alcohols of the pentaerythritol series, methods for preparing, and compositions containing the same |
| US2450079A (en) * | 1943-04-23 | 1948-09-28 | Atlas Powder Co | Waxy polyol ether-esters |
| US2491478A (en) | 1947-05-12 | 1949-12-20 | Arkansas Company Inc | Polyalcohol-fatty acid-aliphatic amine combinations useful as textile assistants andprocess of producing the same |
| US2480185A (en) | 1947-07-25 | 1949-08-30 | Carbide & Carbon Chem Corp | Esters of mixtures of polyoxyalkylene monohydroxy compounds |
| US2705724A (en) * | 1951-05-24 | 1955-04-05 | Exxon Research Engineering Co | Reduction of acidity in synthetic ester lubes with olefin oxides |
| US2800500A (en) * | 1953-10-30 | 1957-07-23 | Exxon Research Engineering Co | Manufacture of synthetic lubricants in the presence of phenothiazine |
| US2911434A (en) * | 1956-04-24 | 1959-11-03 | Visco Products Co | Surface active dicarboxylic acid esters of polyalkylene oxides |
| US3098827A (en) | 1958-03-31 | 1963-07-23 | Nalco Chemical Co | Demulsification of petroleum oil emulsions |
| US3113932A (en) | 1959-02-09 | 1963-12-10 | Johnson & Son Inc S C | Drying compositions comprising polyepoxide polyesters of tetrahydrophthalic acid and aliphatic glycols modified with unsaturated monocarboxylic acid |
| US3331802A (en) | 1964-07-24 | 1967-07-18 | Emery Industries Inc | Polyesters from dibasic acids, monobasic acids, glycols, and trihydric alcohols as plasticizers for vinyl resins |
| US3398201A (en) * | 1965-05-07 | 1968-08-20 | Gaf Corp | Reaction products from 2-alkoxybutanols and 3, 5,x - polyalkoxyalkanols with alkylene oxides |
| US3442835A (en) | 1965-08-19 | 1969-05-06 | Ashland Oil Inc | Water-dispersible polyalkylene glycol modified drying oil alkyd |
| US3457206A (en) | 1966-05-16 | 1969-07-22 | Staley Mfg Co A E | Water dispersible alkyd resins comprising esterified units of an alkoxypolyoxyethylene glycol |
| GB1217005A (en) * | 1967-02-28 | 1970-12-23 | Witco Chemical Corp | Preparation of polyols containing esters groups from polyethers, cyclic anhydrides, and 1,2-epoxides |
| US3585185A (en) * | 1968-05-13 | 1971-06-15 | Wyandotte Chemicals Corp | Ester-containing polyols |
| ES367288A1 (es) * | 1968-05-17 | 1971-04-01 | Sandoz Ag | Procedimiento para tenir lana con colorantes reactivos. |
| US3859318A (en) * | 1969-05-19 | 1975-01-07 | Lubrizol Corp | Products produced by post-treating oil-soluble esters of mono- or polycarboxylic acids and polyhydric alcohols with epoxides |
| US3957855A (en) * | 1971-06-11 | 1976-05-18 | The Lubrizol Corporation | Ester-containing compositions |
| DE2316293A1 (de) * | 1973-03-31 | 1974-10-10 | Basf Ag | Verfahren zur herstellung von polyesterolen |
| DE2348518B2 (de) * | 1973-09-27 | 1978-06-29 | Basf Ag, 6700 Ludwigshafen | Pulverförmige, hochkonzentrierte und dispersionsstabile Farbstoffzubereitungen und Verfahren zu deren Herstellung |
| CH598404B5 (en, 2012) * | 1975-04-04 | 1978-04-28 | Ciba Geigy Ag | |
| LU76633A1 (en, 2012) * | 1977-01-24 | 1978-09-13 | ||
| DE2943902A1 (de) * | 1979-10-31 | 1981-05-14 | Hoechst Ag, 6000 Frankfurt | Verwendung von veresterten oxalkylaten als praeparationsmittel fuer farbstoffe und entsprechende farbstoffzubereitungen |
-
1975
- 1975-04-04 CH CH429375A patent/CH598404B5/xx not_active IP Right Cessation
- 1975-04-04 CH CH429375D patent/CH429375A4/xx unknown
-
1976
- 1976-03-29 US US05/671,874 patent/US4055393A/en not_active Expired - Lifetime
- 1976-03-31 DK DK155476A patent/DK155476A/da not_active IP Right Cessation
- 1976-03-31 FR FR7609306A patent/FR2306230A1/fr active Granted
- 1976-03-31 DE DE2613755A patent/DE2613755C2/de not_active Expired
- 1976-04-01 GB GB13268/76A patent/GB1522091A/en not_active Expired
- 1976-04-02 CA CA249,513A patent/CA1071227A/en not_active Expired
- 1976-04-02 BE BE165800A patent/BE840330A/xx not_active IP Right Cessation
- 1976-04-02 NL NLAANVRAGE7603484,A patent/NL182225C/xx not_active IP Right Cessation
- 1976-04-02 ZA ZA762008A patent/ZA762008B/xx unknown
- 1976-04-03 ES ES446677A patent/ES446677A1/es not_active Expired
- 1976-04-03 JP JP51036725A patent/JPS51122020A/ja active Granted
-
1980
- 1980-04-02 US US06/136,614 patent/US4268686A/en not_active Expired - Lifetime
- 1980-12-22 US US06/219,164 patent/US4389214A/en not_active Expired - Fee Related
-
1981
- 1981-03-19 US US06/245,420 patent/US4430261A/en not_active Expired - Fee Related
-
1986
- 1986-02-26 JP JP61039337A patent/JPS61179384A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61179384A (ja) | 1986-08-12 |
| FR2306230A1 (fr) | 1976-10-29 |
| CH429375A4 (en, 2012) | 1977-06-15 |
| NL182225C (nl) | 1988-02-01 |
| NL7603484A (nl) | 1976-10-06 |
| US4055393A (en) | 1977-10-25 |
| ZA762008B (en) | 1977-04-27 |
| US4268686A (en) | 1981-05-19 |
| BE840330A (fr) | 1976-10-04 |
| NL182225B (nl) | 1987-09-01 |
| FR2306230B1 (en, 2012) | 1978-11-17 |
| JPS51122020A (en) | 1976-10-25 |
| US4430261A (en) | 1984-02-07 |
| JPS6135170B2 (en, 2012) | 1986-08-12 |
| DE2613755C2 (de) | 1982-04-01 |
| GB1522091A (en) | 1978-08-23 |
| ES446677A1 (es) | 1977-06-01 |
| CH598404B5 (en, 2012) | 1978-04-28 |
| DK155476A (da) | 1976-10-05 |
| US4389214A (en) | 1983-06-21 |
| DE2613755A1 (de) | 1976-10-14 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |