US3255078A - Process for the treatment of fiber articles of synthetic polyamides and composition produced - Google Patents
Process for the treatment of fiber articles of synthetic polyamides and composition produced Download PDFInfo
- Publication number
- US3255078A US3255078A US123623A US12362361A US3255078A US 3255078 A US3255078 A US 3255078A US 123623 A US123623 A US 123623A US 12362361 A US12362361 A US 12362361A US 3255078 A US3255078 A US 3255078A
- Authority
- US
- United States
- Prior art keywords
- fiber articles
- synthetic polyamides
- treatment
- composition produced
- articles
- 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 - Lifetime
Links
- 239000004952 Polyamide Substances 0.000 title claims description 14
- 229920002647 polyamide Polymers 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 5
- 239000000835 fiber Substances 0.000 title description 12
- 229920000642 polymer Polymers 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 230000000845 anti-microbial effect Effects 0.000 claims description 2
- 150000001408 amides Chemical group 0.000 claims 1
- -1 arylene imidazolium compounds Chemical class 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 230000003377 anti-microbal effect Effects 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- BQQBGUBOAYGXED-UHFFFAOYSA-M [Br-].C[N+]1=C(N(C2=C1C=CC=C2)CCCCCCCCCCCC)C2=CC=CC=C2 Chemical compound [Br-].C[N+]1=C(N(C2=C1C=CC=C2)CCCCCCCCCCCC)C2=CC=CC=C2 BQQBGUBOAYGXED-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VJAUEAIDROUYNR-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanediol Chemical compound C=1C=CC(Cl)=C(Cl)C=1C(O)(O)C1=CC=CC=C1 VJAUEAIDROUYNR-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- 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
- Y10S8/21—Nylon
Definitions
- the present invention relates to the treatment of fiber articles of synthetic polyamides; more particularly it concerns a process for the treament of fiber articles of synthetic polyamides which consists in treating the fiber articles with antimicrobic arylene imidazolium compounds.
- Suitable antimicrobic arylene imidazolium compounds have been described, for example, in French patent specification No. 1,248,412; they correspond to the general formula
- X represents an acid radical, for example the radical of hydrochloric acid, sulfuric acid or methylsulfuric acid or a radical of a phosphoric acid or a low molecular weight aliphatic carboxylic acid
- Y stands for an aryl radical, for instance for a phenyl or naphthyl radical which may be substituted, for example by halogen and/or hydroxyl groups, or for a heterocyclic radical, for example the furyl, pyrryl, thienyl, pyridyl, indolyl 0r quinolyl radical; one of the .substituents R and R is an alkyl radical or an esterified or amidated acid group which contains 1-4 carbon atoms and
- the textile material thus treated has an antimicrobic finish.
- the outstanding fastness to washing of this finish can be seen in the following table in which the width of'the inhibition zones which result around samples of the finished textile material placed on agar-agar plates inoculated with the various microbes given in the table before washing and after Washing several times with a commercial detergent, is indicated in millimeters.
- Example 3 Socks produced from filaments of polymeric e-caprolactam are agitated for 60 minutes in an aqueous bath having a goods-to-liquor ratio of 1:40 and containing, per liter, 50 g. of l-methyl-2-phenyl-3-dodecyl-benzimidazo1- ium bromide, the initial temperature of-40 C. being slowly raised to 98 C. The socks are finally dried. Their antimicrobic finish was also found to be very fast to washing.
- antimicrobic arylene imidazolium compounds to be used according to the invention is surprising since other known, highly active antimocrobic agents, such as quaternary ammonium compounds of the dimethyl-dodecyl-benzyl-ammonium chloride type, or halogenated dihydroxy-diphenyl compounds of the dichloro-dihydroxy-diphenyl methane type, do not yield satisfactory results in the treatment of fiber articles of synthetic polyamides.
- highly active antimocrobic agents such as quaternary ammonium compounds of the dimethyl-dodecyl-benzyl-ammonium chloride type, or halogenated dihydroxy-diphenyl compounds of the dichloro-dihydroxy-diphenyl methane type
- synthetic polyamides herein used denotes long-chain synthetic polyamides which have recurring amide groups as an integral part of the main polymer chain and which are capable of being formed into filaments; such' synthetic polyamides may be derived from hexamethylene diamine and adipic acid, from s-aminocaproic acid or from e-caprolactam (cf. Kirk-Othmer: Encyclopedia of Chemical Technology, vol. 10, New York, 1953, pages 916-917).
- Process for imparting antimicrobic properties to fiber articles of long-chain synthetic polyamides having recurring amide groups as an integralpart of the main polymer chain comprising contacting-the articles in an aqueous medium with an active amount of 1-methyl-2- phenyl-3-dodecyl-benzimidazolium bromide.
- a method for imparting antimicrobial properties to fiber articles of long-chain synthetic polyamides having recurring amide groups as an integral part of the main polymer chain comprising contacting the fiber articles with an active amount of a compound having the formula arylene :0 Y X wherein X is an acid anion; Y is phenyl; R is an alkyl of 1-4 carbon atoms; and R is an alkyl which contains about 10-12 carbon atoms, and arylene is phenyl.
- a fibrous article consisting essentially of a longchain synthetic polyamide having recurring amide groups as an integral part of the main polymer chain, said polyamide having incorporated thereon an active amount of a compound having the formula wherein X is an acid anion; Y is phenyl; R is an alkyl of 1-4 carbon atoms; and R is an alkyl which contains about 10-12 carbon atoms, and arylene is phenyl.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Polyamides (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0031754 | 1960-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3255078A true US3255078A (en) | 1966-06-07 |
Family
ID=7094342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US123623A Expired - Lifetime US3255078A (en) | 1960-07-23 | 1961-07-13 | Process for the treatment of fiber articles of synthetic polyamides and composition produced |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3255078A (en:Method) |
| BE (1) | BE606383A (en:Method) |
| GB (1) | GB911238A (en:Method) |
| NL (1) | NL267363A (en:Method) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4101654A (en) * | 1973-07-19 | 1978-07-18 | Petrolite Corporation | Microbiocidal process employing full quaternary nitrogen-heterocyclic phosphonates |
| US5869027A (en) * | 1996-04-22 | 1999-02-09 | Wood; Louis L. | Method for odor reduction |
| WO2017117678A1 (en) * | 2016-01-08 | 2017-07-13 | Simon Fraser University | Poly(phenylene) and m-terphenyl as protecting groups for benzimidazolium hydroxides |
| US11230626B2 (en) | 2016-08-04 | 2022-01-25 | Simon Fraser University | Crosslinking of hydroxide stable, polybenzimidazoliums and polyimidazoliums membranes and ionomers |
| US11299464B2 (en) | 2016-07-29 | 2022-04-12 | Simon Fraser University | Stable poly(imidazolium) hydroxides |
| US11802187B2 (en) | 2017-04-10 | 2023-10-31 | Simon Fraser University | Polyphenylenes, methods, and uses thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1248412A (fr) * | 1956-12-01 | 1960-11-07 | Bayer Ag | Composés d'arylidène-imidazolium |
-
0
- NL NL267363D patent/NL267363A/xx unknown
-
1961
- 1961-07-12 GB GB25308/61A patent/GB911238A/en not_active Expired
- 1961-07-13 US US123623A patent/US3255078A/en not_active Expired - Lifetime
- 1961-07-20 BE BE606383A patent/BE606383A/fr unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1248412A (fr) * | 1956-12-01 | 1960-11-07 | Bayer Ag | Composés d'arylidène-imidazolium |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4101654A (en) * | 1973-07-19 | 1978-07-18 | Petrolite Corporation | Microbiocidal process employing full quaternary nitrogen-heterocyclic phosphonates |
| US5869027A (en) * | 1996-04-22 | 1999-02-09 | Wood; Louis L. | Method for odor reduction |
| WO2017117678A1 (en) * | 2016-01-08 | 2017-07-13 | Simon Fraser University | Poly(phenylene) and m-terphenyl as protecting groups for benzimidazolium hydroxides |
| CN108473441A (zh) * | 2016-01-08 | 2018-08-31 | 西蒙弗雷泽大学 | 作为苯并咪唑鎓氢氧化物的保护基团的聚(亚苯基)和间三联苯 |
| US10800874B2 (en) | 2016-01-08 | 2020-10-13 | Simon Fraser University | Poly(phenylene) and m-Terphenyl as protecting groups for benzimidazolium hydroxides |
| CN108473441B (zh) * | 2016-01-08 | 2021-12-21 | 西蒙弗雷泽大学 | 作为苯并咪唑鎓氢氧化物的保护基团的聚(亚苯基)和间三联苯 |
| US11299464B2 (en) | 2016-07-29 | 2022-04-12 | Simon Fraser University | Stable poly(imidazolium) hydroxides |
| US11230626B2 (en) | 2016-08-04 | 2022-01-25 | Simon Fraser University | Crosslinking of hydroxide stable, polybenzimidazoliums and polyimidazoliums membranes and ionomers |
| US11802187B2 (en) | 2017-04-10 | 2023-10-31 | Simon Fraser University | Polyphenylenes, methods, and uses thereof |
| US11970590B2 (en) | 2017-04-10 | 2024-04-30 | Simon Fraser University | Polyphenylenes, methods, and uses thereof |
| US12084554B2 (en) | 2017-04-10 | 2024-09-10 | Simon Fraser University | Polyphenylenes, methods, and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| BE606383A (fr) | 1961-11-16 |
| GB911238A (en) | 1962-11-21 |
| NL267363A (en:Method) |
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