CA1056082A - Traitement d'un tissu pour survetement - Google Patents

Traitement d'un tissu pour survetement

Info

Publication number: CA1056082A
Authority: CA; Canada
Prior art keywords: groups; carbodiimide; fluoroaliphatic; terminal; unsubstituted
Prior art date: 1973-11-05
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

CA185,022A

Other languages

English (en)

Other versions

CA185022S (en

Inventor

Dennis P. Landucci

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.)

3M Co

Original Assignee

Minnesota Mining and Manufacturing Co

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.)

1973-11-05

Filing date

1973-11-05

Publication date

1979-06-05

1973-11-05 Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co

1973-11-05 Priority to CA185,022A priority Critical patent/CA1056082A/fr

1979-04-19 Priority to CA325,840A priority patent/CA1071225A/fr

1979-06-05 Application granted granted Critical

1979-06-05 Publication of CA1056082A publication Critical patent/CA1056082A/fr

Status Expired legal-status Critical Current

Links

239000004744 fabric Substances 0.000 title claims abstract description 47
238000011282 treatment Methods 0.000 title description 13
125000006162 fluoroaliphatic group Chemical group 0.000 claims abstract description 38
150000001718 carbodiimides Chemical class 0.000 claims abstract description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
239000000203 mixture Substances 0.000 claims abstract description 30
229920002554 vinyl polymer Polymers 0.000 claims abstract description 16
229920002994 synthetic fiber Polymers 0.000 claims abstract description 15
239000012209 synthetic fiber Substances 0.000 claims abstract description 14
230000002209 hydrophobic effect Effects 0.000 claims abstract description 8
VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims description 41
238000000034 method Methods 0.000 claims description 21
239000011737 fluorine Substances 0.000 claims description 20
229910052731 fluorine Inorganic materials 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 15
229920001228 polyisocyanate Polymers 0.000 claims description 15
239000005056 polyisocyanate Substances 0.000 claims description 15
125000000962 organic group Chemical group 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 9
239000011248 coating agent Substances 0.000 claims description 8
238000000576 coating method Methods 0.000 claims description 8
125000005442 diisocyanate group Chemical group 0.000 claims description 8
230000002940 repellent Effects 0.000 claims description 8
239000005871 repellent Substances 0.000 claims description 8
239000012736 aqueous medium Substances 0.000 claims description 6
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
125000005647 linker group Chemical group 0.000 claims description 5
NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
239000002609 medium Substances 0.000 claims description 3
230000008016 vaporization Effects 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
229920000642 polymer Polymers 0.000 description 33
239000000243 solution Substances 0.000 description 29
239000003921 oil Substances 0.000 description 20
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 15
239000000463 material Substances 0.000 description 13
238000005108 dry cleaning Methods 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
229920000728 polyester Polymers 0.000 description 8
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
-1 Perfluoroalkyl Acrylate Chemical compound 0.000 description 7
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 7
150000001252 acrylic acid derivatives Chemical class 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
239000004677 Nylon Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000000835 fiber Substances 0.000 description 5
238000004900 laundering Methods 0.000 description 5
229920001778 nylon Polymers 0.000 description 5
239000007921 spray Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
239000012948 isocyanate Substances 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000004952 Polyamide Substances 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000004140 cleaning Methods 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229920002647 polyamide Polymers 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
238000005299 abrasion Methods 0.000 description 2
229920003180 amino resin Polymers 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
230000000149 penetrating effect Effects 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000004753 textile Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
HAAITRDZHUANGT-UHFFFAOYSA-N 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid Chemical compound O[N+]([O-])=O.ClC1=CC(Cl)=CC=C1C(OCC=1C2=CC=CC(Cl)=C2SC=1)CN1C=NC=C1 HAAITRDZHUANGT-UHFFFAOYSA-N 0.000 description 1
MLCHGAGOYTZQHT-UHFFFAOYSA-N 2,2,3,3,4-pentamethyl-1-phenyl-1$l^{5}-phosphetane 1-oxide Chemical compound CC1C(C)(C)C(C)(C)P1(=O)C1=CC=CC=C1 MLCHGAGOYTZQHT-UHFFFAOYSA-N 0.000 description 1
RDEGKASNQOKKBC-UHFFFAOYSA-N 2,2,3,4,4-pentamethyl-1-phenylphosphetane Chemical compound CC1(C)C(C)C(C)(C)P1C1=CC=CC=C1 RDEGKASNQOKKBC-UHFFFAOYSA-N 0.000 description 1
DBZGWWBWDYGSRA-UHFFFAOYSA-N 3-methyl-1-phenyl-2,5-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound C1C(C)=CCP1(=O)C1=CC=CC=C1 DBZGWWBWDYGSRA-UHFFFAOYSA-N 0.000 description 1
CWKYHZMWPLSOFA-UHFFFAOYSA-N 3-methyl-1-phenyl-2,5-dihydrophosphole Chemical compound C1C(C)=CCP1C1=CC=CC=C1 CWKYHZMWPLSOFA-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Polymers [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
101100231512 Caenorhabditis elegans ceh-9 gene Proteins 0.000 description 1
101100028482 Caenorhabditis elegans pal-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
101100536883 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) thi5 gene Proteins 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical compound O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 description 1
229920001774 Perfluoroether Polymers 0.000 description 1
229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
101100240664 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nmt1 gene Proteins 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000000732 arylene group Chemical group 0.000 description 1
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
238000005187 foaming Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
KCAMXZBMXVIIQN-UHFFFAOYSA-N octan-3-yl 2-methylprop-2-enoate Chemical compound CCCCCC(CC)OC(=O)C(C)=C KCAMXZBMXVIIQN-UHFFFAOYSA-N 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
229920001289 polyvinyl ether Polymers 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
125000001453 quaternary ammonium group Polymers 0.000 description 1
229920005604 random copolymer Polymers 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000004758 synthetic textile Substances 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
125000005628 tolylene group Chemical group 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1

Landscapes

Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

CA185,022A 1973-11-05 1973-11-05 Traitement d'un tissu pour survetement Expired CA1056082A (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CA185,022A CA1056082A (fr)	1973-11-05	1973-11-05	Traitement d'un tissu pour survetement
CA325,840A CA1071225A (fr)	1973-11-05	1979-04-19	Traitement antitaches pour survetements

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA185,022A CA1056082A (fr)	1973-11-05	1973-11-05	Traitement d'un tissu pour survetement

Publications (1)

Publication Number	Publication Date
CA1056082A true CA1056082A (fr)	1979-06-05

Family

ID=4098297

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA185,022A Expired CA1056082A (fr)	1973-11-05	1973-11-05	Traitement d'un tissu pour survetement

Country Status (1)

Country	Link
CA (1)	CA1056082A (fr)

1973
- 1973-11-05 CA CA185,022A patent/CA1056082A/fr not_active Expired

Publication	Publication Date	Title
US3896251A (en)	1975-07-22	Outerwear fabric treatment
US4215205A (en)	1980-07-29	Fluoroaliphatic radical and carbodiimide containing compositions for fabric treatment
US4024178A (en)	1977-05-17	Fluoroaliphatic radical containing carbodiimides
US4540765A (en)	1985-09-10	Polyurethanes containing perfluoroalkyl groups and a process for their production
CA1099444A (fr)	1981-04-14	Polymere fluore a bloc urethanne-uree-oxyde d'ethylene, servant a nettoyer les textiles
US6479605B1 (en)	2002-11-12	High-durability, low-yellowing repellent for textiles
US4958039A (en)	1990-09-18	Modified fluorocarbonylimino biurets
CA1152260A (fr)	1983-08-23	Traitement pour tapis
US4043964A (en)	1977-08-23	Carpet treating and treated carpet
DE69927679T2 (de)	2006-04-27	Blockierte olimogere isocyanate, deren herstellung und verwendung
US4834764A (en)	1989-05-30	Process for obtaining wash-and cleaning resistant textile finishes with reactive perfluoroalkyl-containing (co) polymers and/or precondensates and a blocked isocyanate compound
US6451717B1 (en)	2002-09-17	Highly durable oil/water repellents for textiles
US5509939A (en)	1996-04-23	Soil-release process
US5164252A (en)	1992-11-17	Hydrophobizing and oleophobizing compositions
EP0862668A1 (fr)	1998-09-09	Compositions fluorochimiques ayant un effet repulsif durable
KR20010070118A (ko)	2001-07-25	섬유 재료의 발유 및 발수 가공용 조성물
US5372731A (en)	1994-12-13	Composition and process for the finishing of textiles
DE60217412T2 (de)	2007-10-18	Behandelte teppiche aus poly(trimethylenterephthalat)
AU2007269865A1 (en)	2008-01-10	Method of providing repellency
KR20100090693A (ko)	2010-08-16	친수성 플루오르화된 방오성 공중합체
CA1056082A (fr)	1979-06-05	Traitement d'un tissu pour survetement
CA1071225A (fr)	1980-02-05	Traitement antitaches pour survetements
JP3276958B2 (ja)	2002-04-22	フルオロカーバメート防汚剤
US5481027A (en)	1996-01-02	Fluorocarbamate soil-release agents
Bovenkamp et al.	1981	Fluoroalkyl-substituted siloxanes as liquid repellent fabric finishes