CA1102344A - Modification de fibres aux fluorocarbones - Google Patents

Modification de fibres aux fluorocarbones

Info

Publication number: CA1102344A
Authority: CA; Canada
Prior art keywords: group; carbon atoms; choh; additive; integer
Prior art date: 1975-06-30
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

Application number

CA256,055A

Other languages

English (en)

Inventor

Frank Mares

Bryce C. Oxenrider

Cyril Woolf

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Honeywell International Inc

Original Assignee

Allied Chemical Corp

Priority date (The priority date 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 date listed.)

1975-06-30

Filing date

1976-06-30

Publication date

1981-06-02

1976-06-30 Application filed by Allied Chemical Corp filed Critical Allied Chemical Corp

1981-06-02 Application granted granted Critical

1981-06-02 Publication of CA1102344A publication Critical patent/CA1102344A/fr

Status Expired legal-status Critical Current

Links

239000000835 fiber Substances 0.000 title claims abstract description 144
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 title abstract description 16
230000004048 modification Effects 0.000 title description 2
238000012986 modification Methods 0.000 title description 2
239000000654 additive Substances 0.000 claims abstract description 353
230000000996 additive effect Effects 0.000 claims abstract description 240
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 89
239000007788 liquid Substances 0.000 claims abstract description 48
239000000203 mixture Substances 0.000 claims description 108
125000004432 carbon atom Chemical group C* 0.000 claims description 77
-1 polypropylene Polymers 0.000 claims description 70
229910052739 hydrogen Inorganic materials 0.000 claims description 59
238000000034 method Methods 0.000 claims description 55
125000000217 alkyl group Chemical group 0.000 claims description 41
229910052731 fluorine Inorganic materials 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 36
150000001875 compounds Chemical class 0.000 claims description 29
239000000460 chlorine Substances 0.000 claims description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
125000002947 alkylene group Chemical group 0.000 claims description 24
239000000376 reactant Substances 0.000 claims description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
229920005989 resin Polymers 0.000 claims description 23
239000011347 resin Substances 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
230000008569 process Effects 0.000 claims description 21
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
239000001301 oxygen Substances 0.000 claims description 18
229910052760 oxygen Inorganic materials 0.000 claims description 18
239000011737 fluorine Substances 0.000 claims description 17
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 14
239000012948 isocyanate Substances 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 11
150000003254 radicals Chemical class 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
150000002513 isocyanates Chemical class 0.000 claims description 9
239000004698 Polyethylene Substances 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
229910052740 iodine Inorganic materials 0.000 claims description 7
229920000573 polyethylene Polymers 0.000 claims description 7
150000003512 tertiary amines Chemical class 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
239000004952 Polyamide Substances 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 5
239000011630 iodine Substances 0.000 claims description 5
229920002647 polyamide Polymers 0.000 claims description 5
239000004743 Polypropylene Substances 0.000 claims description 3
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
229920001748 polybutylene Polymers 0.000 claims description 3
229920000728 polyester Polymers 0.000 claims description 3
230000002940 repellent Effects 0.000 claims description 3
239000005871 repellent Substances 0.000 claims description 3
229920005992 thermoplastic resin Polymers 0.000 claims description 3
150000001413 amino acids Chemical class 0.000 claims description 2
229920002239 polyacrylonitrile Polymers 0.000 claims description 2
229920001155 polypropylene Polymers 0.000 claims description 2
229910020587 CmF2m+1 Inorganic materials 0.000 claims 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
229910052717 sulfur Inorganic materials 0.000 claims 4
239000011593 sulfur Substances 0.000 claims 4
125000003700 epoxy group Chemical group 0.000 claims 1
238000000137 annealing Methods 0.000 abstract description 19
238000001125 extrusion Methods 0.000 abstract description 15
238000005299 abrasion Methods 0.000 abstract description 12
238000004900 laundering Methods 0.000 abstract description 9
238000010348 incorporation Methods 0.000 abstract description 3
239000000155 melt Substances 0.000 abstract description 2
239000004744 fabric Substances 0.000 description 87
239000003921 oil Substances 0.000 description 85
235000019198 oils Nutrition 0.000 description 85
239000000243 solution Substances 0.000 description 83
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
150000002148 esters Chemical class 0.000 description 54
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 51
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 50
238000006243 chemical reaction Methods 0.000 description 48
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
239000000047 product Substances 0.000 description 44
239000002904 solvent Substances 0.000 description 42
239000000543 intermediate Substances 0.000 description 40
239000000523 sample Substances 0.000 description 38
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
238000012360 testing method Methods 0.000 description 35
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 33
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 30
239000005020 polyethylene terephthalate Substances 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
239000000975 dye Substances 0.000 description 27
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 27
229910052799 carbon Inorganic materials 0.000 description 25
239000002609 medium Substances 0.000 description 25
239000003054 catalyst Substances 0.000 description 23
238000002360 preparation method Methods 0.000 description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
239000010755 BS 2869 Class G Substances 0.000 description 20
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
239000006185 dispersion Substances 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
150000002989 phenols Chemical class 0.000 description 18
238000010438 heat treatment Methods 0.000 description 17
150000002924 oxiranes Chemical class 0.000 description 17
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 17
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
150000001298 alcohols Chemical class 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000001704 evaporation Methods 0.000 description 15
229920000139 polyethylene terephthalate Polymers 0.000 description 15
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 14
229910002092 carbon dioxide Inorganic materials 0.000 description 14
230000008020 evaporation Effects 0.000 description 14
238000010992 reflux Methods 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
239000002689 soil Substances 0.000 description 14
238000004458 analytical method Methods 0.000 description 13
238000003756 stirring Methods 0.000 description 13
238000009835 boiling Methods 0.000 description 12
239000000839 emulsion Substances 0.000 description 12
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 11
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 11
229920002292 Nylon 6 Polymers 0.000 description 11
238000004043 dyeing Methods 0.000 description 11
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
229910000041 hydrogen chloride Inorganic materials 0.000 description 11
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
229920004934 Dacron® Polymers 0.000 description 10
240000008415 Lactuca sativa Species 0.000 description 10
239000002253 acid Substances 0.000 description 10
239000013078 crystal Substances 0.000 description 10
238000004821 distillation Methods 0.000 description 10
239000012442 inert solvent Substances 0.000 description 10
239000010410 layer Substances 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000012045 salad Nutrition 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
238000005108 dry cleaning Methods 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 8
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000000463 material Substances 0.000 description 8
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 8
238000011282 treatment Methods 0.000 description 8
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
239000012043 crude product Substances 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 7
150000003335 secondary amines Chemical class 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
235000017550 sodium carbonate Nutrition 0.000 description 7
230000003068 static effect Effects 0.000 description 7
238000005406 washing Methods 0.000 description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000008188 pellet Substances 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000004448 titration Methods 0.000 description 6
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
239000012736 aqueous medium Substances 0.000 description 5
150000001555 benzenes Chemical class 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
229960001701 chloroform Drugs 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000010705 motor oil Substances 0.000 description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000010186 staining Methods 0.000 description 5
238000010561 standard procedure Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000004753 textile Substances 0.000 description 5
238000002411 thermogravimetry Methods 0.000 description 5
229940086542 triethylamine Drugs 0.000 description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
239000002285 corn oil Substances 0.000 description 4
238000006731 degradation reaction Methods 0.000 description 4
238000003618 dip coating Methods 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000011521 glass Substances 0.000 description 4
DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
150000004694 iodide salts Chemical class 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229960001047 methyl salicylate Drugs 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000002243 precursor Substances 0.000 description 4
150000003138 primary alcohols Chemical group 0.000 description 4
238000012545 processing Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
230000008961 swelling Effects 0.000 description 4
239000011701 zinc Substances 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
239000004342 Benzoyl peroxide Substances 0.000 description 3
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
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ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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230000015572 biosynthetic process Effects 0.000 description 3
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical class Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 3
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 3
238000004140 cleaning Methods 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
230000002860 competitive effect Effects 0.000 description 3
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238000002788 crimping Methods 0.000 description 3
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MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
229920006240 drawn fiber Polymers 0.000 description 3
235000019256 formaldehyde Nutrition 0.000 description 3
ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
125000004356 hydroxy functional group Chemical group O* 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
229920001778 nylon Polymers 0.000 description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
239000006259 organic additive Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000002356 single layer Substances 0.000 description 3
238000009987 spinning Methods 0.000 description 3
239000007921 spray Substances 0.000 description 3
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239000002184 metal Substances 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
BHGADZKHWXCHKX-UHFFFAOYSA-N methane;potassium Chemical compound C.[K] BHGADZKHWXCHKX-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
CVXXHXPNTZBZEL-UHFFFAOYSA-N methyl 4-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=O)C=C1 CVXXHXPNTZBZEL-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
229940099990 ogen Drugs 0.000 description 1
239000011368 organic material Substances 0.000 description 1
235000010292 orthophenyl phenol Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000010525 oxidative degradation reaction Methods 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
125000005359 phenoxyalkyl group Chemical group 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
125000003884 phenylalkyl group Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
150000003022 phthalic acids Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920006122 polyamide resin Polymers 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
238000010944 pre-mature reactiony Methods 0.000 description 1
230000000063 preceeding effect Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical group [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
238000007342 radical addition reaction Methods 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
239000005060 rubber Substances 0.000 description 1
238000009991 scouring Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
150000003334 secondary amides Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000271 synthetic detergent Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
238000010998 test method Methods 0.000 description 1
TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/408—Acylated amines containing fluorine atoms; Amides of perfluoro carboxylic acids
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols

Landscapes

Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Polyamides (AREA)

CA256,055A 1975-06-30 1976-06-30 Modification de fibres aux fluorocarbones Expired CA1102344A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US59192975A	1975-06-30	1975-06-30
US591,929		1975-06-30
US67735776A	1976-04-15	1976-04-15
US677,357		1976-04-15

Publications (1)

Publication Number	Publication Date
CA1102344A true CA1102344A (fr)	1981-06-02

Family

ID=27081299

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA256,055A Expired CA1102344A (fr)	1975-06-30	1976-06-30	Modification de fibres aux fluorocarbones

Country Status (4)

Country	Link
JP (1)	JPS525400A (fr)
CA (1)	CA1102344A (fr)
DE (2)	DE2628047A1 (fr)
GB (1)	GB1543081A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4460785A (en) *	1982-09-30	1984-07-17	Allied Corporation	Acid chloride of pyromellitic anhydride
US4939289A (en) *	1985-08-15	1990-07-03	Allied-Signal Inc.	Fiber surface modifiers

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2821495C2 (de) *	1978-05-17	1984-06-28	Battelle-Institut E.V., 6000 Frankfurt	Mittel zur Antischmutzausrüstung von Lacken
US4192754A (en) *	1978-12-28	1980-03-11	Allied Chemical Corporation	Soil resistant yarn finish composition for synthetic organic polymer yarn
US4264484A (en) *	1979-01-24	1981-04-28	Minnesota Mining And Manufacturing Company	Carpet treatment
US4321403A (en)	1979-06-04	1982-03-23	Allied Corporation	N-Methylpyrrolidone solvent in esterification of carboxybenzenes
US4252982A (en) *	1979-10-29	1981-02-24	Allied Chemical Corporation	Aliphatic ester solvent in esterification of carboxybenzenes
US4340749A (en)	1979-12-21	1982-07-20	Minnesota Mining And Manufacturing Company	Carpet treatment
JPS57171762A (en) *	1981-04-13	1982-10-22	Teijin Ltd	Anti-stain finish treating agent for synthetic fiber
DK162979C (da) *	1981-06-26	1992-06-01	Du Pont	Polyfluoralkylestere, deres fremstilling og anvendelse
JPS5818474A (ja) *	1981-07-27	1983-02-03	帝人株式会社	熱可塑性合成繊維の耐汚染仕上げ処理剤
JPS5818475A (ja) *	1981-07-27	1983-02-03	帝人株式会社	合成繊維の耐汚染仕上げ処理剤
DE3233830A1 (de) *	1982-09-11	1984-03-15	Hoechst Ag, 6230 Frankfurt	Perfluoralkyl-malein- und -fumarsaeureamide, verfahren zu deren herstellung und ihre verwendung als schmutzabweisendes mittel
JPS6145126U (ja) *	1984-08-29	1986-03-25	三菱油化株式会社	流体供給用軟質積層ホース
CN101460495B (zh)	2006-03-31	2013-08-14	财团法人乙卯研究所	具有杂环的化合物
EP2669283A1 (fr)	2007-10-02	2013-12-04	Shionogi&Co., Ltd.	Dérivé dýoxazolidinone doté dýune bague hétéro composée de 7 éléments
JP6663320B2 (ja) *	2016-07-25	2020-03-11	信越化学工業株式会社	テトラカルボン酸ジエステル化合物、ポリイミド前駆体の重合体及びその製造方法、ネガ型感光性樹脂組成物、パターン形成方法、及び硬化被膜形成方法
TW202424310A (zh) *	2022-09-14	2024-06-16	日商大金工業股份有限公司	撥液性纖維的製造方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3547861A (en) *	1968-04-12	1970-12-15	Allied Chem	Novel fluorinated acrylates and polyacrylates
US3657320A (en) *	1968-11-08	1972-04-18	Allied Chem	Perfluoroalkoxyalkyl-substituted carbamates
CH511971A (de) *	1969-07-07	1971-01-29	Ciba Geigy Ag	Verwendung von Perfluoralkylmonocarbonsäureestern zum Veredeln von Textilmaterial
US3786093A (en) *	1969-10-17	1974-01-15	Allied Chem	Novel bisamides containing fluorine

1976
- 1976-06-23 DE DE19762628047 patent/DE2628047A1/de active Granted
- 1976-06-26 DE DE19762628776 patent/DE2628776A1/de not_active Ceased
- 1976-06-29 JP JP51076130A patent/JPS525400A/ja active Granted
- 1976-06-29 GB GB2710376A patent/GB1543081A/en not_active Expired
- 1976-06-30 CA CA256,055A patent/CA1102344A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4460785A (en) *	1982-09-30	1984-07-17	Allied Corporation	Acid chloride of pyromellitic anhydride
US4939289A (en) *	1985-08-15	1990-07-03	Allied-Signal Inc.	Fiber surface modifiers

Also Published As

Publication number	Publication date
JPS525400A (en)	1977-01-17
GB1543081A (en)	1979-03-28
DE2628047A1 (de)	1977-01-27
JPS6223030B2 (fr)	1987-05-21
DE2628776A1 (de)	1977-01-27
DE2628047C2 (fr)	1987-08-27

Legal Events

Date	Code	Title	Description
1998-06-02	MKEX	Expiry

Publication	Publication Date	Title
DE69216707T2 (de)	1997-07-10	Perfluoralkylhalogenide und Derivate
US4219625A (en)	1980-08-26	Fluorinated polyol esters
KR100889714B1 (ko)	2009-03-23	발수발유제 조성물
US4024178A (en)	1977-05-17	Fluoroaliphatic radical containing carbodiimides
US4215205A (en)	1980-07-29	Fluoroaliphatic radical and carbodiimide containing compositions for fabric treatment
US3171861A (en)	1965-03-02	Fluorinated aliphatic alcohols
JPS6223030B2 (fr)	1987-05-21
EP0073364B1 (fr)	1985-11-21	Procédé pour la préparation de produits de condensation contenant des substituants perfluoroalcoyles, les produits de condensation ainsi préparés et leur utilisation
JPH0429781B2 (fr)	1992-05-19
JPS6124557A (ja)	1986-02-03	フルオロケミカルアロフアネート
US3754026A (en)	1973-08-21	Fluorocarbon amides
EP3638654B1 (fr)	2021-01-27	Composés d'additifs fondus, leurs procédés d'utilisation, articles et compositions les comprenant
US3636085A (en)	1972-01-18	Perfluoroalkylsulfonamido - alkyl esters of fumaric acid and other ethylenically unsaturated polybasic acids and polymers thereof
US4065630A (en)	1977-12-27	Polyoxyalkylene fluoroalkyltrimellitates
JPH02760A (ja)	1990-01-05	脂肪族弗化アルコール、イソシアネートおよび置換芳香族化合物より成るウレタン、その製造方法およびその用途
US4195105A (en)	1980-03-25	Fluorinated polyalkylene polyamides as stain repellents
DE1468850C3 (de)	1975-01-16	Verfahren zur Herstellung von Fluor enthaltenden Polymerisaten
DE2135139A1 (de)	1972-01-27	Neue Styrylverbindungen, Verfahren zu deren Herstellung und deren Verwendung
US3576017A (en)	1971-04-20	Haloalkanoyl derivatives of fluorinated amides
CH182470A (de)	1936-02-15	Sägeblatt.
US4099910A (en)	1978-07-11	Surface modification of polymeric substrates via interaction with azido formyl or azido sulfonyl compounds
US4020087A (en)	1977-04-26	N-imidazolidinone perfluoroalkylcarboxylic acid ester
US4278773A (en)	1981-07-14	Dispersible compositions of fluorocarbon resins
EP0368338B1 (fr)	1995-02-22	Composition repoussant l'eau et l'huile
US4052485A (en)	1977-10-04	Perfluoro compounds containing phosphorus

CA1102344A - Modification de fibres aux fluorocarbones - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (4)

Publications (1)

Family

ID=27081299

Family Applications (1)

Country Status (4)

Cited By (2)

Families Citing this family (16)

Family Cites Families (4)

Cited By (2)

Also Published As

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