US1918373A - Wetting agents - Google Patents
Wetting agents Download PDFInfo
- Publication number
- US1918373A US1918373A US382077A US38207729A US1918373A US 1918373 A US1918373 A US 1918373A US 382077 A US382077 A US 382077A US 38207729 A US38207729 A US 38207729A US 1918373 A US1918373 A US 1918373A
- Authority
- US
- United States
- Prior art keywords
- wetting
- products
- agents
- materials
- acid
- 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
- 239000000080 wetting agent Substances 0.000 title description 2
- 239000003795 chemical substances by application Substances 0.000 description 13
- 150000001408 amides Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 238000009736 wetting Methods 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000001117 sulphuric acid Substances 0.000 description 9
- 235000011149 sulphuric acid Nutrition 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- -1 uric acid ester Chemical class 0.000 description 7
- 238000007792 addition Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000005187 foaming Methods 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 150000003931 anilides Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 4
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000010985 leather Substances 0.000 description 4
- 230000000149 penetrating effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- 235000011941 Tilia x europaea Nutrition 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 239000004571 lime Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- MCYTYTUNNNZWOK-LCLOTLQISA-N penetratin Chemical compound C([C@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CCCNC(N)=N)[C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(N)=O)C1=CC=CC=C1 MCYTYTUNNNZWOK-LCLOTLQISA-N 0.000 description 2
- 108010043655 penetratin Proteins 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical class [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- WCZWUYYJZVBKDZ-FGSXEWAUSA-N Vertine Natural products O([C@@H]1C[C@H](N2CCCC[C@@H]2C1)C=1C=C(C(=CC=11)OC)OC)C(=O)C=CC2=CC=C(O)C1=C2 WCZWUYYJZVBKDZ-FGSXEWAUSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 231100001010 corrosive Toxicity 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- PYUYQYBDJFMFTH-WMMMYUQOSA-N naphthol red Chemical compound CCOC1=CC=CC=C1NC(=O)C(C1=O)=CC2=CC=CC=C2\C1=N\NC1=CC=C(C(N)=O)C=C1 PYUYQYBDJFMFTH-WMMMYUQOSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 238000004048 vat dyeing Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/62—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/628—Compounds containing nitrogen
-
- 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
-
- 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
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
Description
i'latented July 18, 1933 UNITED STATES PATENT OFFICE.
HEINRICH BERTSCH, F OHZ'EMNI'IZ, GERMANY, ASSIGNOR '10 H. TE. 36mm AKTIEN- GESELLSCHAIT, OI CEEMNI'EZ, GERMANY, A CORPORATION OF G W e WETTING AGENTS Ito Drawing. Application filed July 29, 1929, Serial 5 leather industries. The forms in which they are most frequently used are their salts, the soaps, and the salts of their sulphuric esters, the Turkey red oils. Both classes of substances, in spite of all other difierences, ex-
" hibit a common defect, namely that they form insoluble salts, the so-called lime soaps, with alkali earth and metal salts contained in water with which they are used. This is to be ascribed to the fact that the soaps and Turkey red oils contain carboxyl groups still capable of reaction. Recently products similar to Turkey red oils but having a high content of organically combined sulphuric acid and thus a relatively high resistance to limehave been produced successfully b using special methods of sulphonation. The formation of lime soaps can be entirely obviated, however, only by com lete elimination of the carboxyl group wh1ch is capable of reaction. This is possible, for instance, by sulphonating the alcohols corresponding to the higher fatty acids instead of the fatty acidsthemselves. By the sulphonation of the former, products are obtained which are extraordinarily insensitive to lime and magnesia salts.
The object of the present invention is to provide a further class of (products or preparations which may be a (led totreatment agents instead of soaps. Turkey red oils or the like. This class comprises the sulphuric esters of the amides, anilides or other amides substituted in the ammonia radicle of fatty or oily acids of high molecular weight.
These products may be obtained in various ways, for example by sulphonating the amides, anilides and so forth of hi her fatty acids, particularly the amides an anilides of unsaturated or hydroxy-fatt acids. Thus for instance, the oleic acid ami e produced in known manner may be treated with the usual sulphonating agents such as concentrated sulphuric acid, fuming sulphuric acid or chloro-sulphonic acid, if occasion demand in the presence of water binding agents such as y for manifold uses in the Ho. 382,077, and in Germany September 5, 1988.
anhydrous organic acids, their anhydrides or chlorides. In this manner the sulphuric esters of the fatty acid amides, anilides and so forth are obtained more or less according to the following scheme:
CH3.(CHs)1.CH=CH.(CHa)7.COOH (oleic acid) CH3.(CH2)1-CH=CH.(CH2)1.CONH: (oleic acid amide) CH3.(CH2)7.CHCH.(CH2)1.CONH2 (sulglpuric ester 0! oleic acid aml c 504K The neutralized sulphonation products,
apart from their powers of resistance which a in this case also are dependent upon the absence of any free carboxyl group, exhibit high Wetting, foaming, emulsifying and cleanlng properties and also the characteristlc of imparting a soft, smooth, but not sticky feel to textile fibres and allied materials. Said products are, therefore, suitable textile and leather industries and also for other purposes,.
Thus in all forms of treatment of textiles with neutral, acid or alkali treatment liquids, said products enhance the action by the materially increased wetting and impregnation achieved and by the conversion of fats, impurities and the like into a ueous dispersions.
In vat dyeing the addition of such products enables the reduction to be performed in the presence of little, or weak, alkali, which is important in the dyeing of vat dyestufi's on animal fibres. In naphthol red dyeing it is in this manner possible to dye even on animal fibres if desired. Addition of the substances above referred to also facilitates the moistening or wetting of pulverulent dyestufi's and other powdersfor their conversion into aqueous liquids for the production of pastes and so forth. For spinning purposes, their aqueous dispersions with or without further additions have proved to be valuable moistening a nts. Similarly the action of treatment liqu1ds in the manufacture and handling of leather is accelerated, strengthened and advantageously modified b the addition of the sulp onated fatty aci amidea' Said compounds are also capable of being used with advantage in the paper manufacturing and treating industry, in the manufacture of pigment colors, in the dyeing of furs, wherever it is a question of the wetting efl'ect, dispersion, penetration and conveyances of effective substances or components. The properties of said products also allow of their use in pharmacy as emulsifers, in the pharmaceutical industry as foaming agents and skin-protective media and also as constituents of selves and creams, as a substitute for vasenols and the like.
It is a characteristic feature of said products that they render textile fibres and other materials treated therewith soft and pliable without givin the same a sticky feel so that they are suita le for the softening or revivin of such materials. I
heir efiicacy as agents in the extermination of pests depends upon the same powers of active wetting and enetration. he products are also valuab e as additions to corrosives and as boring oils in the metal industry. Furthermore they may be employed asdisersives of the nature of protective colloids, or instance, in the manufacture of ink and in fat cleavage. Their penetratin powers are of advantage when they are use as additions to ceramic masses and their rapidly effective wetting'powers make them useful as dust-binding agents; i
In the appended claims, the ex ression increasing the penetrating power is employed to describe that power of reagents to come easily or quickly into contact with the material "being treated, whether it be in a wettin dispersing, impregnating, foaming, emulsi ying, cleanmg or a like process. Further, the term fatty acid in the absence of limiting modifiers is employed in its broad sense and also refers to, in addition to the acids of the fatty acid series, other oily acids, including the unsaturated and the hydroxy acids. Y
I claim v 1. A reagent for increasing the penetrating power of treating agents com rising, a sulphuric acid ester-of an amide o ahig'her fatty acid.
2. A. reagent adapted for increasing the penetrating power of treating agents used in thetextile, leather, paper and fat-com.
vertin industries and the like, comprising a sul uric acid ester of an anilide having substituted for hydrogen'in its nitrogen nucleus an acyl radical derived from a higher fatty acid. a
3. A composition of matter for treating fibrous pulverulent and water-re llent materials, and materials not rea ly soluble compr sing a sulphuric acid ester of an amide of a higher fatt acid in combination with aknownagent a apted for altering the properties of such materials, said composition having increased efiiciency including penetratin power over the known agent when used a one.
4. Inthe rocess of producing a wetting, foaming or ispersion agent adapted for the treatment of fibrous, pulverulent, water-repellent materials, and difiicultlysoluble materials, the step comprisin incorporating in said agent su huric aci esters of amides of the higher atty acids.
5. A composition of matter com rising a treating agent dependent in part or its effectiveness ufion its penetrating power into such materia as fibrous, pulverulent, waterrepellant materials and diflicultly soluble materials, incombination with a substance adapted to enhance the netrating power of said agent consisting m a sulphuric acid ester of an amide of an acid of the higher fatty acid series.
6. A reagent for enhancing the wetting, impre ating, foaming, emuls1fying,dispersing, 0 eaning and like properties of treating agents comprising a sulphuric acid ester of an amide of a higher saturated fatty acid.
7. A reagent for enhancing the wetting, impre ating, foaming, emulsifying, dispersing, c eaning and like properties of treating agents comprising a sulphuric acid ester of an amide of a higher unsaturated fatty acid.
8, A reagent for enhancing the wetting, impre ating, foaming, emulsifying, dispersing, 0 eaning and like properties of treating agents comprising a sulphuric acid ester of an amide of a higher hydroxy fatty acid.
HEINRICH BERTSCH.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1918373X | 1928-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1918373A true US1918373A (en) | 1933-07-18 |
Family
ID=7749276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US382077A Expired - Lifetime US1918373A (en) | 1928-09-05 | 1929-07-29 | Wetting agents |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1918373A (en) |
-
1929
- 1929-07-29 US US382077A patent/US1918373A/en not_active Expired - Lifetime
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