US3615738A - Water repellent - Google Patents
Water repellent Download PDFInfo
- Publication number
- US3615738A US3615738A US734568A US3615738DA US3615738A US 3615738 A US3615738 A US 3615738A US 734568 A US734568 A US 734568A US 3615738D A US3615738D A US 3615738DA US 3615738 A US3615738 A US 3615738A
- Authority
- US
- United States
- Prior art keywords
- water repellent
- fiber
- water
- carbon atoms
- meta
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 230000002940 repellent Effects 0.000 title claims abstract description 33
- 239000005871 repellent Substances 0.000 title claims abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- 235000015278 beef Nutrition 0.000 claims description 3
- 239000003760 tallow Substances 0.000 claims description 3
- 239000000835 fiber Substances 0.000 abstract description 20
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 238000000034 method Methods 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 5
- 238000001035 drying Methods 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 4
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000001846 repelling effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- GKXVJHDEWHKBFH-UHFFFAOYSA-N xylylenediamine group Chemical group C=1(C(=CC=CC1)CN)CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical class [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- -1 wool Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
Definitions
- An object of this invention therefore is to provide a novel water repellent which is inexpensive and which has superior washing-durability.
- Another object of this invention is to provide an efficient method for imparting waterI-I-repellency whereby the heattreatment temperature required is comparatively lowered.
- R and R are each alkyl or alkenyl groups having from seven to 21 carbon numbers, inclusive, and wherein one substituent is in either the meta or the paraposition to the other.
- a process for treating a fiber with the water repellent comprising applying the water repellent material to the fiber, drying the treated fiber and heat treating the fiber.
- the heat treating temperature generally is from about 130 C. to about 200 C., with the preferred temperature range being from about 130 C. to about 150 C. Generally from about 3-4 minutes will be a sufficient heat treatment time at the above temperatures.
- the compound described in this invention can be obtained in accordance with conventional processes. For example, by the reaction of at least one aromatic diamine selected from meta-xylylene diamine and para-xylylene diamine, with a higher fatty acid chloride, a free higher fatty acid or an ester of a higher fatty acid. From the viewpoint of simplicity and economy of materials, it is advantageous to produce the water repellent compound of this invention from xylylene diamines and free fatty acids.
- the fatty acids to be used include either saturated or unsaturated fatty acids having from eight to 22 carbon atoms. These fatty acids are usually obtained by the hydrolysis of mixtures of natural fats and oils and such mixtures may be directly used as the material for the synthesis. It is preferred, however, to use the fatty acid, when it contains a large proportion of unsaturated bonds, after it has been partially or completely hydrogenated, in order to obtain improved stability and water repellent properties for the above-mentioned compound.
- the application of the compound of the present invention to fiber products may be effected by the use of a solution, but it is usually applied in the form of a suspension, in which the compound is dispersed in the amounts of from 0.l-3% by weight, preferably 0.5-2% by weight, in a suitable dispersion medium.
- the resultant suspension is then applied to the fiber products to be finished in a conventional manner, such as by dipping, brushing, spraying, and the like, to give water repellent fiber products.
- the proportion of the water repellent compound to the dispersion medium may be greater than 3% by weight, but further increases in the proportion will not generally impart significantly. greater improvements in the water repelling properties.
- the use of less than 0.1% by weight of the compound will generally give insufficient water repelling action.
- Excellent washing-durability for the water repelling finish can be attained by a procedure which comprises dipping the fiber products in said suspension, drying by means of hot air or the like, and heat-treating at -150 C. for 3-4 minutes. Although appreciable water repellency is obtainable by this treatment at temperatures below 130 C., it is preferred to conduct the heat-treatment at a temperature of about 130 C. to impart greater water repellency and washing durability.
- the heat-treatment may be also carried out at temperatures above C., to as high as 200 C., so long as the fiber products to be finished can endure the higher temperatures.
- the period of the heat-treatment may be shorter than 3 minutes to obtain the desired effect, but it is generally preferred to perform the treatment for 3-4 minutes. Heattreatment may also be carried out for a period over 4 minutes, but this is generally unnecessary, since satisfactory results are obtainable within a period of 3-4 minutes.
- the water repellent compounds to be used in this invention are only slightly soluble in almost all solvents at normal temperatures, so that purification is difficult.
- the waterrepellent compounds of this invention can be used in their raw reaction form without any particular purification to impart general water repellent properties.
- purification can be effected by a procedure which comprises dissolving the compound in a suitable solvent such as alcohol at high temperatures; discoloring, if necessary, with a suitable discolorant; and then cooling the solution so as to crystallize out pure material.
- a suitable solvent such as alcohol
- Suitable dispersion media which may be used in the practice of this invention include organic solvents having a boiling point below 150 C.
- organic solvents having a boiling point below 150 C.
- a lower alcohol with less than five carbon atoms an acetic acid ester, benzene, toluene, cyclohexane and similar hydrocarbons, acetone, methyl ethyl ketone and similar ketones, dioxane and the like.
- aqueous media containing a hydrophilic organic solvent or a surface active agent may be used.
- the liquid suspension of the present invention be first prepared as a highly concentrated liquid, for example, from about 30-50% by weight. Diluted to the desired concentration may be accomplished immediately before use.
- the water repellent of the present invention may be used as a mixture, in any desired proportion, of meta-substituted and/or parasubstituted compounds.
- the fiber products to be treated with the water repellent of this invention include a variety of synthetic and natural fibers. Superior effects are obtained when it is applied to synthetic fibers such as polyesters, Nylon, polyacrylonitrile, polyvinyl alcohol and the like.
- Excellent water repellency can also be imparted when the water repellent of this invention is applied to cotton, wool, rayon and acetate fibers.
- the water repellent compound of this invention can also give improved softness, as well as water repellency.
- EXAMPLE 1 A reactor fitted with a stirrer was charged with 284 parts of purified stearic acid and 68 parts of meta-xylylene diamine was added thereto. After the addition was completed, the reaction temperature was raised to C., and the reaction was carried out for 3 hours while removing water formed by condensation. The reaction was continued for another hour after raising the temperature to 200 C.
- the compound so obtained namely, meta-xylylene diamine disteramide, was then suspended in 99 parts by weight of isopropyl alcohol using a homogenizer.
- Cut pieces of cloth, 20 cm. square, made of various fiber products, were immersed for several minutes in the above suspension, then squeezed with a mangle, dried by the use of a hot-air dryer at 100 C. and finally individual groups were heat-treated at 130 C. and 150 C. for 4 minutes each. The cloths so treated were then used as test samples.
- the water repellency test was conducted according to standard spray testing techniques. The results are shown below.
- the same procedure used in example 1 was carried out with the exception that para-xylylene diamine was substituted for meta-xylylene diamine.
- the para-xylylene diamine distearamide so obtained was suspended in benzene at concentrations of 1% and 2% by the use of a homogenizer to form two suspensions.
- Polyester fiber cloth was immersed in the resultant suspension for 1 minute, dried by means of hot-air and then heattreated at 150 C. for 3 minutes. The results are shown below.
- R, and R are each selected from the group consisting of an alkyl radical, said alkyl radical having from seven to 21 carbon atoms, and an alkenyl radical, having from seven to 21 carbon atoms and being selected from the group consisting of an alkenyl radical containing one internally-positioned double bond and an alkenyl radical containing two internally-positioned double bonds, said substituents containing R, and R on said benzene ring being in a meta or pararelationship.
- R, and R are each a linear alkyl radical containing 17 carbon atoms.
- R, and R are each a linear alkyl radical containing 15 carbon atoms.
- R, and R each contain from 13 to 17 carbon atoms and wherein each is derived from beef tallow fatty acids.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3543667 | 1967-06-05 | ||
| JP1105668A JPS4832918B1 (enrdf_load_stackoverflow) | 1968-02-23 | 1968-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3615738A true US3615738A (en) | 1971-10-26 |
Family
ID=26346427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US734568A Expired - Lifetime US3615738A (en) | 1967-06-05 | 1968-06-05 | Water repellent |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3615738A (enrdf_load_stackoverflow) |
| FR (1) | FR1580392A (enrdf_load_stackoverflow) |
| GB (1) | GB1198154A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3879300A (en) * | 1972-10-25 | 1975-04-22 | Colgate Palmolive Co | Diamine containing softener compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5702806A (en) * | 1991-07-18 | 1997-12-30 | O'dell; Robin D. | Decorative laminate surface layer |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2103872A (en) * | 1933-12-12 | 1937-12-28 | Ig Farbenindustrie Ag | Higr molecular nitrogenous organic compounds containing carboxylic groups |
| US2106447A (en) * | 1936-06-05 | 1938-01-25 | C J Osborne Co | Pigmented composition |
| US2149273A (en) * | 1937-01-13 | 1939-03-07 | Du Pont | Polyamides |
-
1968
- 1968-06-05 US US734568A patent/US3615738A/en not_active Expired - Lifetime
- 1968-06-05 GB GB26739/68A patent/GB1198154A/en not_active Expired
- 1968-07-03 FR FR1580392D patent/FR1580392A/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2103872A (en) * | 1933-12-12 | 1937-12-28 | Ig Farbenindustrie Ag | Higr molecular nitrogenous organic compounds containing carboxylic groups |
| US2106447A (en) * | 1936-06-05 | 1938-01-25 | C J Osborne Co | Pigmented composition |
| US2149273A (en) * | 1937-01-13 | 1939-03-07 | Du Pont | Polyamides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3879300A (en) * | 1972-10-25 | 1975-04-22 | Colgate Palmolive Co | Diamine containing softener compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1769523A1 (de) | 1971-03-04 |
| DE1769523B2 (enrdf_load_stackoverflow) | 1975-06-12 |
| GB1198154A (en) | 1970-07-08 |
| FR1580392A (enrdf_load_stackoverflow) | 1969-09-05 |
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