US2051947A - Wetting, cleansing, and emulsifying agents and method of producing the same - Google Patents
Wetting, cleansing, and emulsifying agents and method of producing the same Download PDFInfo
- Publication number
- US2051947A US2051947A US702098A US70209833A US2051947A US 2051947 A US2051947 A US 2051947A US 702098 A US702098 A US 702098A US 70209833 A US70209833 A US 70209833A US 2051947 A US2051947 A US 2051947A
- Authority
- US
- United States
- Prior art keywords
- cleansing
- vegetable
- animal
- wetting
- alkyl
- 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
- 238000000034 method Methods 0.000 title description 8
- 238000009736 wetting Methods 0.000 title description 2
- 239000003599 detergent Substances 0.000 title 1
- 239000003995 emulsifying agent Substances 0.000 title 1
- 239000000080 wetting agent Substances 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 description 11
- 235000013311 vegetables Nutrition 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 229920002994 synthetic fiber Polymers 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 230000002708 enhancing effect Effects 0.000 description 7
- 239000002657 fibrous material Substances 0.000 description 7
- 150000005840 aryl radicals Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 4
- -1 aryl isothiourea series Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000002541 isothioureas Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- FPVQTRAZCRXBRH-UHFFFAOYSA-N dodecyl carbamimidothioate;hydrochloride Chemical group Cl.CCCCCCCCCCCCSC(N)=N FPVQTRAZCRXBRH-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OFYJUQNXYAHUOG-UHFFFAOYSA-N [ClH]1(C=CC=C1)=O Chemical compound [ClH]1(C=CC=C1)=O OFYJUQNXYAHUOG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- KIRRTPIRNCBRPG-UHFFFAOYSA-N dodecyl carbamimidothioate Chemical compound CCCCCCCCCCCCSC(N)=N KIRRTPIRNCBRPG-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- GKPIXYIFLKNNKB-UHFFFAOYSA-N hexadecyl carbamimidothioate Chemical compound CCCCCCCCCCCCCCCCSC(N)=N GKPIXYIFLKNNKB-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 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
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/50—Derivatives of urea, thiourea, cyanamide, guanidine or urethanes
-
- 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
- Y10S516/06—Protein or carboxylic compound containing
Definitions
- isothiourea salts the constituent of the molecule which is characteristic for the 45 capillary active action appears in aqueous solution in the form of a positive ion, emulsions can be made herewith in which the particles of the emulsion possess a positive electric charge.
- Isothiourea salts are particularly well suited for add- 50 ing to dye baths of basic dye-stuffs, since, in contradistinction to most commercial products, they do not fiocculate basic dyestuffs and they ensure a satisfactory and uniform thorough dyeing.
- a process for enhancing the efilciency of treating liquids for animal. vegetable or artificial fibers comprising the addition to known treating agents for fibrous materials of a compound of the general formula [NHz.C(SR) :NHlAc, wherein "R” means a radical selected from the group consisting of the alkyl and aryl radicals, and Ac" means an acid radical.
- a process for enhancing the 'eiilciency of 39 treating liquids for animal, vegetable or artificial fibers comprising the addition to known treating agents for fibrous materials of a compound of the general formula [NH:.C(SR) :NHlAc, wherein R" means a radical selected from the group consisting of the alkyl and aryl radicals wherein a hydrogen atom is substituted by an alkoxy group.
- a process for enhancing the efilciency-of treating liquids for animal, vegetable or artificial fibers comprising the addition to known treating agents for fibrous materials of a compound of the general formula [NI-Iz.C(SR) :NHlAc, wherein "R means a radical selected from a group consisting of the alkyl and aryl radicals, wherein a. hydrogen atom is substituted by an alkylimine group.
- a process for enhancing the emciency of treating liquids for animal, vegetable or artificial fibers comprising the addition to known treating agents for fibrous materials of a compound of the general formula' [NHz.C(SR) :NHlAc, wherein "it” means a radical selected from a group consisting of the alkyl and aryl radicals, wherein a hydrogen atom is substituted by an alkoxy group.
- a process for enhancing the efliciency of treating liquids for animal. vegetable or artificial fibers comprising the addition to known treating agents for fibrous materials of a compound of 5 the general formula [NHa.C(SR)-:NH]Ac',wherein R" means an alkyl radical with from 12 to 16 2 carbon atoms.
- a process for enhancing the eiilciency of treating liquids for animal, vegetable or artificial 10 fibers comprising the additionto mown treating agents for fibrous materials ofa compound of the general formula [NHz.C(SR) :NHlAc, wherein "R” means the n-dode'cyl radical. 7;
- a product for treating liquids for animal, vegetable, and artificial fibers comprising a known agent ior improving the properties of said 10 fibers in combination with S-dodecyl isothiourea havantide.
- a product for treating liquids for animal, vegetable, and artificial flbe comprising a known agent for improving the properties of said 15 fibers in combination with S-dodecyl-isothiourea chloride.
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Coloring (AREA)
Description
Patented Aug. '25, 1-936 YUN-ITEDTSTATES PATENT OFFICE.
. v 2,051,941 a, CLEANSING, sun EMULSIFYING.
WETTIN AGENTS AND BIE'I'HOD OF PRODUCING Heinz Hnnsdiecker and Egon Vogt,
No Application December 12, 1933,
Serial No. 702,098. In Germany December '10 claims. (Cl. 252-1) 'wherein hlg" denotes halogen and R" a substituted or non-substituted alkyl or aryl radical or a salt thereof. The products are readily soluble in 5 water. The halogen contained in them can be replaced by other acid ions.
It has been found that the aqueous solutions of the S-alkyl and S-aryl isothiourea salts possess a very high capillary activity, particularly when the alkyl or aryl residue added on possesses a molecular weight which is not too low. Thus, for exam ple, solutions of S-dodecylisothiourea chloride form a very stable froth even at high dilution and possess considerable wetting "powers with respect to animal, vegetable and artificial fibres. Exactly the same holds for the corresponding decyl, tetradecyl and hexadecyl derivatives. The choice. of the anion is of secondary importance since all the essential properties, that is to say, the capillary depression froth formation, etc., are for the most part independent of the nature of the anion. In the case of members-of the alkyl or aryl isothiourea series of higher molecular weight, (tetradecyl and S-hexadecylisothiourea) a very satis- 35 factory dispersing and cleansing property is obtained in addition to the properties already mentioned. These products are superior to normal soaps inasmuch as their soap-like character is maintained even when acids are added, and consequently the acid-washing process, which is of importance in the washing of wool, can be carried out herewith without difiiculty.
'Since in the isothiourea salts the constituent of the molecule which is characteristic for the 45 capillary active action appears in aqueous solution in the form of a positive ion, emulsions can be made herewith in which the particles of the emulsion possess a positive electric charge. Isothiourea salts are particularly well suited for add- 50 ing to dye baths of basic dye-stuffs, since, in contradistinction to most commercial products, they do not fiocculate basic dyestuffs and they ensure a satisfactory and uniform thorough dyeing.
Since the properties of the isothiourea deriva- 55 tives depend to only a subsidiary extent on the special nature of the added alkyl or aryl residue, isothiourea salts with other non-substituted or substituted hydrocarbon residues can be used with similar success. The,fo1lowing compounds amongst others come into question:-- 5
NH2.C.(S.C5H3. ortho N'Hs.
para NHCOGsHn) :NHlAc wherein Ac" indicates an acid residue, such as chlorlon. K
Finally reference must be made to the possibility of making S-alkyl and S-aryl iso-thiourea salts in which the amide or imide hydrogen atoms are replaced by any desired organic residues and which, as regards their behaviour, follow the aforementioned products.
What we claim is:-
1. A process for enhancing the efilciency of treating liquids for animal. vegetable or artificial fibers, comprising the addition to known treating agents for fibrous materials of a compound of the general formula [NHz.C(SR) :NHlAc, wherein "R" means a radical selected from the group consisting of the alkyl and aryl radicals, and Ac" means an acid radical.
2. A process for enhancing the 'eiilciency of 39 treating liquids for animal, vegetable or artificial fibers, comprising the addition to known treating agents for fibrous materials of a compound of the general formula [NH:.C(SR) :NHlAc, wherein R" means a radical selected from the group consisting of the alkyl and aryl radicals wherein a hydrogen atom is substituted by an alkoxy group.
3. A process for enhancing the efilciency-of treating liquids for animal, vegetable or artificial fibers, comprising the addition to known treating agents for fibrous materials of a compound of the general formula [NI-Iz.C(SR) :NHlAc, wherein "R means a radical selected from a group consisting of the alkyl and aryl radicals, wherein a. hydrogen atom is substituted by an alkylimine group.
4. A process for enhancing the emciency of treating liquids for animal, vegetable or artificial fibers, comprising the addition to known treating agents for fibrous materials of a compound of the general formula' [NHz.C(SR) :NHlAc, wherein "it" means a radical selected from a group consisting of the alkyl and aryl radicals, wherein a hydrogen atom is substituted by an alkoxy group.
2 spams-r 5. A process for enhancing the efliciency of treating liquids for animal. vegetable or artificial fibers, comprising the addition to known treating agents for fibrous materials of a compound of 5 the general formula [NHa.C(SR)-:NH]Ac',wherein R" means an alkyl radical with from 12 to 16 2 carbon atoms.
.6. A process for enhancing the eiilciency of treating liquids for animal, vegetable or artificial 10 fibers comprising the additionto mown treating agents for fibrous materials ofa compound of the general formula [NHz.C(SR) :NHlAc, wherein "R" means the n-dode'cyl radical. 7; A process for enhancing the eillciency of 15 treating liquids for animal, vegetable ,or artificial fibers, comprising the addition to known treating agents for fibrous materials of a compound oi the general formula [NH2.C(SR) :NHJAc, wherein "R" means the n-hexadecyl radical. 20 8. A product for treating liquids for animal,
vegetable and artificial fibers, comi a known agent for improving the properties of said fibers, in combination with a compound of the general formula [NH2.C(SR) :NHlAc, wheiein "3 means a radical selected from the group 0011- 5 sisting oi the alhl and aryl radicals and Ac means an acid radical. V j
9. A product for treating liquids for animal, vegetable, and artificial fibers. comprising a known agent ior improving the properties of said 10 fibers in combination with S-dodecyl isothiourea halosenide. v p
10. A product for treating liquids for animal, vegetable, and artificial flbe comprising a known agent for improving the properties of said 15 fibers in combination with S-dodecyl-isothiourea chloride.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE425188X | 1932-12-14 | ||
| DEH134464D DE705355C (en) | 1932-12-14 | 1932-12-15 | Wetting, dispersing and foaming agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2051947A true US2051947A (en) | 1936-08-25 |
Family
ID=60387689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US702098A Expired - Lifetime US2051947A (en) | 1932-12-14 | 1933-12-12 | Wetting, cleansing, and emulsifying agents and method of producing the same |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2051947A (en) |
| DE (1) | DE705355C (en) |
| FR (1) | FR765475A (en) |
| GB (1) | GB425188A (en) |
| NL (1) | NL37681C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3720624A (en) * | 1969-07-18 | 1973-03-13 | Kurita Water Ind Ltd | Cationic surface active substance, method for manufacturing same |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1056602B (en) * | 1951-12-12 | 1959-05-06 | Unilever Nv | Process for the preparation of mercaptoalkane sulfonates |
| DE1031303B (en) * | 1953-07-13 | 1958-06-04 | Boehme Fettchemie Gmbh | Process for the preparation of thiourea derivatives containing sulfonic acid groups |
-
1932
- 1932-12-15 DE DEH134464D patent/DE705355C/en not_active Expired
-
1933
- 1933-12-12 US US702098A patent/US2051947A/en not_active Expired - Lifetime
- 1933-12-12 NL NL67741A patent/NL37681C/en active
- 1933-12-14 FR FR765475D patent/FR765475A/en not_active Expired
- 1933-12-14 GB GB35259/33A patent/GB425188A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3720624A (en) * | 1969-07-18 | 1973-03-13 | Kurita Water Ind Ltd | Cationic surface active substance, method for manufacturing same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR765475A (en) | 1934-06-11 |
| DE705355C (en) | 1941-04-25 |
| GB425188A (en) | 1935-03-08 |
| NL37681C (en) | 1936-03-16 |
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