US1897120A - hbtot - Google Patents
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- Publication number
- US1897120A US1897120A US1897120DA US1897120A US 1897120 A US1897120 A US 1897120A US 1897120D A US1897120D A US 1897120DA US 1897120 A US1897120 A US 1897120A
- Authority
- US
- United States
- Prior art keywords
- treating
- abietene
- fibrous material
- aqueous
- parts
- 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
- 239000002657 fibrous material Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 11
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 8
- 238000006277 sulfonation reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- STIVVCHBLMGYSL-ZYNAIFEFSA-N abietane Chemical compound CC1(C)CCC[C@]2(C)[C@H]3CC[C@H](C(C)C)C[C@@H]3CC[C@H]21 STIVVCHBLMGYSL-ZYNAIFEFSA-N 0.000 description 6
- 229930000074 abietane Natural products 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 3
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920013683 Celanese Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001397173 Kali <angiosperm> Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/17—Natural resins, resinous alcohols, resinous acids, or derivatives thereof
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/693—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural or synthetic rubber, or derivatives thereof
-
- 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
- Y10S516/03—Organic sulfoxy compound containing
Definitions
- This invention is applica Is to the wet treatmentof textile fibers in substantially all cases where it is advantageous that a quick watt-in and penetrating effect of the treating liqui be obtained.
- sulfonated products which may be derived from sulfonation of the products obtainable by the pyrogenic decomposition of rosin, abietic acid orv abiet l chloride have in aqueous .olution remar able wetting and penetra'mg properties.
- the sulfonic acids of the above roducts may be transformed into water solu 1e salts suc as potassium, sodium and ammonium and in any of these forms may be used as assistants in acid, neutral or alkaline treating baths.
- Example 1 an t ' sugar and Violet BNX as follows.
- a dye bath is made up by vatting 1 part of Anthrene Violet BNX double paste (Color Index 1163)- in 25 parts of water and 0.6 parts of a 10% solution of NaOH and 0.6 parts of sodium hydrosulfite at 60 C.
- the dye vat is then diluted to a total volume of 200 parts with water at 60 C. and then 20 parts of a 10% solution of Glaubers salt are added.
- the cotton yarn is now immersed.
- the dyeing operation exhausts the dye bath. U on oxidation of the skein in air, followed y rinsing and soaping,
- the abietene sulfonic acid so 'um salt may be incorporated directly in the dye vat, thus eliminatin the extra step of treating the fiber outsi e the dye bath. This latter method gives practically the same results as the first method.
- Example 2 The procedure is the same as in Example 1' except that abietane sulfonic acid is used instead of abietene sulfonic acid. The results are substantially the same.
- the process of treating fibrous material which comprises subjecting fibrous material to an aqueous treating bath containing water soluble sulfonatio'n products of a member of the group consisting of abietene, abietine and abietane.
- an aqueous treating ba for fibrous material containing a sulfonation product of a member of the group consisting of abietene, abietine and abietane.
- an aqueous treating bath for fibrous material containing. a water soluble sulfonation derivative of a rosin decomposition roduct ob v tainable by refluxing rosin in t e presence of iron until its acidity has been substantially reduced and distillin to recover a fraction boiling below 4.50 o'.
- an aqueous treatin bat for fibrous material containing an a kali metal salt of abietene sulfonic acid As a new com osition of matter, an aqueous treatin bat for fibrous material containing an a kali metal salt of abietene sulfonic acid.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Description
Evans ANN,
Bo wing.
ciency of aqueous baths for treating textile fibers inconjunction with a variety of treatmg operations of which the following are typical: dyeing of fabrics or fibrous materials, both animal andvegetable; washing and scouring offibers preliminary to the dyeing operation; dyeing of leather; carbonlzing,
iulling and softening of wool; sizing, dressin and the like. This invention is applica Is to the wet treatmentof textile fibers in substantially all cases where it is advantageous that a quick watt-in and penetrating effect of the treating liqui be obtained.
Other and further important objects of this invention will become apparent from the following description and appended claims.
We have found that sulfonated products which may be derived from sulfonation of the products obtainable by the pyrogenic decomposition of rosin, abietic acid orv abiet l chloride have in aqueous .olution remar able wetting and penetra'mg properties.
Due to variations in the source of the abietic acid containing material gosin), the resulting roduct produced t erefrom will vary slig tly in its composition, but we believe that, independent of the source of the abietic acid containing material, the roduct obtained will contain-a large proportion of a specifie hydrocarbon, abietene or abietine. A number of these various products are described by Ruzicka, Helvetica Chimica Acta, volume 6, pages 838 to 840. We have sulfonated many of these products and find that they are. all useful for our purpose. However, exceptionally outstandin respect is the sulfonation product o a rosindecom osition product obtainable according to U. Patent No. 1,853,353 issued April 12, 1932. This procedure, briefly, consists of refiuxing r'bsin in the presence of iron and at a temperature of about 350 to 375 C. until its acidity has been practically destroyed, and
a. 13am rnoonss or TREATING 'rnxmn 1 it in this v 1. J. WEILAND, AND CLYDE o. HENKE, 01? SOUTH WAU a: m, ASSIGNO msnn ASSIGNMENTS, T0 E. I. no PONT DE m, A coma more or nmaw Application filed February 26, 1980. Serial N0. 481,629.
these sulfonic treating the above defined hydrocarbons of the abietene family with strong sulfonating agents, such as, sulfuric acid monohydrate, at temperatures between about 0,170 50 C.
We have also found that the sulfonation products of abietane, which are more s ecifically described and claimed in U. S. atent' N 0. 1,853,348 can be used in the same way as the sulfonation products, of. abietene. 5W9 believe the general ring structure of abietene and abietane to be the same, the specific difference bein that part of the unsaturation linkages of a ietene are absent in abietane.
The sulfonic acids of the above roducts ma be transformed into water solu 1e salts suc as potassium, sodium and ammonium and in any of these forms may be used as assistants in acid, neutral or alkaline treating baths.
These newprodu'cts even in dilute aqueous I solutions exhibit remarkable wetting and penetrating effects upon fibrous materials. Our preferred concentrations for use are from 0.1% up to about 5% of the treating bath, the latter concentration being sufiiciently highfor most purposes Without waste of material.
The following examples, given in parts by weight, serve to illustrate thenature of our invention.
Example 1 an t ' sugar and Violet BNX as follows. A dye bath is made up by vatting 1 part of Anthrene Violet BNX double paste (Color Index 1163)- in 25 parts of water and 0.6 parts of a 10% solution of NaOH and 0.6 parts of sodium hydrosulfite at 60 C. The dye vat is then diluted to a total volume of 200 parts with water at 60 C. and then 20 parts of a 10% solution of Glaubers salt are added. The cotton yarn is now immersed. The dyeing operation exhausts the dye bath. U on oxidation of the skein in air, followed y rinsing and soaping,
obtained. In case a similar dyeing is made upon untreated cotton the shades obtained are uneven and weak. As an alternative method in the d eing process, the abietene sulfonic acid so 'um salt may be incorporated directly in the dye vat, thus eliminatin the extra step of treating the fiber outsi e the dye bath. This latter method gives practically the same results as the first method.
Enample 2 Example 3 The procedure is the same as in Example 1' except that abietane sulfonic acid is used instead of abietene sulfonic acid. The results are substantially the same.
E p w 2.5 parts of a dyestufi mixture containing 20% of 1-amino-2-methyl-anthraquinone, 5% abietene-sulfonic acid sodium salt are added to 3000 parts of Water at 60 C. The dyestufi is immediately dispersed. 100 parts of celanese silk are then immersed in the dyebath and dyed in the usual manner. The silk is dyed in an even and clear orange shade. 1
We are aware that numerous details of the process may be varied through a wide range without departin from the principles of this invention, an we, therefore, do not purpose limiting the patent granted hereon otherwise than necessitated by the prior art.
We claim as our invention:
1. The process of treating fibrous material, which comprises subjecting fibrous material to an aqueous treating bath containing water soluble sulfonatio'n products of a member of the group consisting of abietene, abietine and abietane.
2. The process of treating fibrous material,
which comprises subjecting fibrous material clear, even, deep shades areto an aqueous treating bath containingwater soluble sulfonation products of abietene.
3. The process of treating fibrous material, which comprises subjecting fibrous material to an aqueous treatin bath containing an alkali metal salt of abletene sulfonic acid.
4. The process of, treating fibrous material which comprises subjecting such material to an aqueous treating bath containing ,a water soluble sulfonation derivative of a rosin decomposition product obtainable by refluxing rosin in the presence of iron until its acidity has been substantiall reduced and distilling to recover a fraction boiling below 450 C.
5. As a new com osition of matter, an aqueous treating ba for fibrous material containing a sulfonation product of a member of the group consisting of abietene, abietine and abietane.
6. As a new com aqueous treating bat containing a sul onation product of abietene.
7. As a new composition of matter, an aqueous treating bath for fibrous material containing. a water soluble sulfonation derivative of a rosin decomposition roduct ob v tainable by refluxing rosin in t e presence of iron until its acidity has been substantially reduced and distillin to recover a fraction boiling below 4.50 o'.
8.1 As a new com osition of matter, an aqueous treatin bat for fibrous material containing an a kali metal salt of abietene sulfonic acid. 1
In testimony whereof, we have hereunto subscribed our names at Carrollville, -Milwaukee County, Wisconsin.
IVAN GUBELMANN. HENRY J. WEILAND. CLYDE O. HENKE.
sition of matter an for fibrous material I
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1897120A true US1897120A (en) | 1933-02-14 |
Family
ID=3424946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1897120D Expired - Lifetime US1897120A (en) | hbtot |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1897120A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3074447A (en) * | 1961-04-17 | 1963-01-22 | Bombardler Joseph Armand | Motor vehicle for cutting, loading and transporting trees |
-
0
- US US1897120D patent/US1897120A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3074447A (en) * | 1961-04-17 | 1963-01-22 | Bombardler Joseph Armand | Motor vehicle for cutting, loading and transporting trees |
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