CA1037659A - Fluorination and sulfo-fluorination of synthetic resins and fibers - Google Patents
Fluorination and sulfo-fluorination of synthetic resins and fibersInfo
- Publication number
- CA1037659A CA1037659A CA215,941A CA215941A CA1037659A CA 1037659 A CA1037659 A CA 1037659A CA 215941 A CA215941 A CA 215941A CA 1037659 A CA1037659 A CA 1037659A
- Authority
- CA
- Canada
- Prior art keywords
- fluorine
- fluorination
- oxygen
- fluorinated
- fabric
- 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
- 229920003002 synthetic resin Polymers 0.000 title claims abstract description 20
- 239000000057 synthetic resin Substances 0.000 title claims abstract description 16
- 238000003682 fluorination reaction Methods 0.000 title abstract description 103
- 229920002994 synthetic fiber Polymers 0.000 title abstract description 3
- 239000012209 synthetic fiber Substances 0.000 title abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 139
- 239000011737 fluorine Substances 0.000 claims abstract description 127
- 239000001301 oxygen Substances 0.000 claims abstract description 94
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 94
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 93
- 239000000835 fiber Substances 0.000 claims abstract description 74
- 229920000728 polyester Polymers 0.000 claims abstract description 51
- 238000011282 treatment Methods 0.000 claims abstract description 49
- 239000004952 Polyamide Substances 0.000 claims abstract description 44
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 44
- 229920002647 polyamide Polymers 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 38
- 229920002239 polyacrylonitrile Polymers 0.000 claims abstract description 33
- 229920000098 polyolefin Polymers 0.000 claims abstract description 33
- 229920005989 resin Polymers 0.000 claims abstract description 15
- 239000011347 resin Substances 0.000 claims abstract description 15
- 239000012429 reaction media Substances 0.000 claims abstract description 9
- 235000019000 fluorine Nutrition 0.000 claims description 125
- 229940060037 fluorine Drugs 0.000 claims description 125
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 123
- 239000007789 gas Substances 0.000 claims description 39
- 150000007942 carboxylates Chemical group 0.000 claims description 14
- 239000000463 material Substances 0.000 abstract description 53
- 230000008569 process Effects 0.000 abstract description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 5
- 150000002148 esters Chemical class 0.000 abstract description 5
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 239000004744 fabric Substances 0.000 description 78
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 40
- 239000000203 mixture Substances 0.000 description 33
- -1 sodium carboxylate Chemical class 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000000523 sample Substances 0.000 description 28
- 238000012360 testing method Methods 0.000 description 27
- 229910001868 water Inorganic materials 0.000 description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 230000035484 reaction time Effects 0.000 description 21
- 239000004677 Nylon Substances 0.000 description 17
- 229920001778 nylon Polymers 0.000 description 17
- 239000004743 Polypropylene Substances 0.000 description 16
- 229920001155 polypropylene Polymers 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000010348 incorporation Methods 0.000 description 15
- 239000002689 soil Substances 0.000 description 13
- 238000006473 carboxylation reaction Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 230000021523 carboxylation Effects 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000004698 Polyethylene Substances 0.000 description 9
- 239000012159 carrier gas Substances 0.000 description 9
- 230000007423 decrease Effects 0.000 description 9
- 229920000573 polyethylene Polymers 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 229940091249 fluoride supplement Drugs 0.000 description 8
- 239000008246 gaseous mixture Substances 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 6
- 229920001225 polyester resin Polymers 0.000 description 6
- 230000003068 static effect Effects 0.000 description 6
- 238000009736 wetting Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910000792 Monel Inorganic materials 0.000 description 5
- 239000005935 Sulfuryl fluoride Substances 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 229920006350 polyacrylonitrile resin Polymers 0.000 description 5
- 229920005672 polyolefin resin Polymers 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 5
- 229920004934 Dacron® Polymers 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 230000000670 limiting effect Effects 0.000 description 4
- 229920006122 polyamide resin Polymers 0.000 description 4
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000004900 laundering Methods 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000012495 reaction gas Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920001059 synthetic polymer Polymers 0.000 description 3
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000305 Nylon 6,10 Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002334 Spandex Polymers 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940110728 nitrogen / oxygen Drugs 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000004759 spandex Substances 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- 101150034533 ATIC gene Proteins 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010009866 Cold sweat Diseases 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920006370 Kynar Polymers 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 101100194706 Mus musculus Arhgap32 gene Proteins 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 208000009989 Posterior Leukoencephalopathy Syndrome Diseases 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 229910018503 SF6 Inorganic materials 0.000 description 1
- 229910006095 SO2F Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 101100194707 Xenopus laevis arhgap32 gene Proteins 0.000 description 1
- WCQRWCFGZARAMR-UHFFFAOYSA-N [F].[F] Chemical compound [F].[F] WCQRWCFGZARAMR-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001265 acyl fluorides Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 229940075397 calomel Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012668 chain scission Methods 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical group 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920006262 high density polyethylene film Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N n-hendecanoic acid Natural products CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 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
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000004383 yellowing 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
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/11—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
- C08J7/126—Halogenation
-
- 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
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/09—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with free halogens or interhalogen compounds
-
- 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
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/34—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxygen, ozone or ozonides
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Polyamides (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43428474A | 1974-01-17 | 1974-01-17 | |
| US05/434,285 US3988491A (en) | 1974-01-17 | 1974-01-17 | Fluorination of polyesters and polyamide fibers |
| US05/443,460 US3940520A (en) | 1974-02-19 | 1974-02-19 | Sulfo-fluorination of synthetic resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1037659A true CA1037659A (en) | 1978-09-05 |
Family
ID=27411846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA215,941A Expired CA1037659A (en) | 1974-01-17 | 1974-12-13 | Fluorination and sulfo-fluorination of synthetic resins and fibers |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS595601B2 (en, 2012) |
| CA (1) | CA1037659A (en, 2012) |
| DE (1) | DE2500598C3 (en, 2012) |
| FR (1) | FR2258412B1 (en, 2012) |
| GB (2) | GB1488932A (en, 2012) |
| IT (1) | IT1028428B (en, 2012) |
| NL (1) | NL7500505A (en, 2012) |
| SE (1) | SE7415733L (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4857404A (en) * | 1988-08-24 | 1989-08-15 | The Dow Chemical Company | Fluorinated carbonaceous fibers |
| JP2855668B2 (ja) * | 1989-07-05 | 1999-02-10 | 三菱化学株式会社 | ポリイミド分離膜 |
| JPH02276154A (ja) * | 1989-08-25 | 1990-11-13 | Sanyo Electric Co Ltd | 電池用セパレータの製造方法 |
| DE4320388A1 (de) * | 1993-06-19 | 1994-12-22 | Ahlbrandt System Gmbh | Verfahren zur Vorbehandlung von zu lackierenden Oberflächen von Kunststoffteilen |
| DE19931348C1 (de) * | 1999-07-07 | 2001-01-18 | Freudenberg Carl Fa | Verfahren zur Oberflächenbehandlung eines faserförmigen Polyphenylsulfids oder Polysulfons |
| EP1565515A1 (en) * | 2002-10-25 | 2005-08-24 | South African Nuclear Energy Corporation Limited | Oxyfluorination |
| CN100430435C (zh) | 2002-10-25 | 2008-11-05 | 南非核能股份有限公司 | 氧氟化 |
-
1974
- 1974-12-13 CA CA215,941A patent/CA1037659A/en not_active Expired
- 1974-12-16 SE SE7415733A patent/SE7415733L/xx unknown
-
1975
- 1975-01-07 FR FR7500316A patent/FR2258412B1/fr not_active Expired
- 1975-01-09 DE DE2500598A patent/DE2500598C3/de not_active Expired
- 1975-01-13 JP JP50005644A patent/JPS595601B2/ja not_active Expired
- 1975-01-16 NL NL7500505A patent/NL7500505A/xx not_active Application Discontinuation
- 1975-01-16 GB GB49512/76A patent/GB1488932A/en not_active Expired
- 1975-01-16 GB GB1910/75A patent/GB1488931A/en not_active Expired
- 1975-01-17 IT IT19353/75A patent/IT1028428B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1488931A (en) | 1977-10-19 |
| JPS595601B2 (ja) | 1984-02-06 |
| NL7500505A (nl) | 1975-07-21 |
| GB1488932A (en) | 1977-10-19 |
| FR2258412B1 (en, 2012) | 1982-03-19 |
| IT1028428B (it) | 1979-01-30 |
| DE2500598C3 (de) | 1979-10-25 |
| DE2500598B2 (en, 2012) | 1979-03-01 |
| FR2258412A1 (en, 2012) | 1975-08-18 |
| SE7415733L (en, 2012) | 1975-07-18 |
| DE2500598A1 (de) | 1975-07-24 |
| JPS50107088A (en, 2012) | 1975-08-23 |
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