US2351338A - Tanning with d'-methoxy-d-hydroxymethyl diglycollic aldehyde - Google Patents
Tanning with d'-methoxy-d-hydroxymethyl diglycollic aldehyde Download PDFInfo
- Publication number
- US2351338A US2351338A US497058A US49705843A US2351338A US 2351338 A US2351338 A US 2351338A US 497058 A US497058 A US 497058A US 49705843 A US49705843 A US 49705843A US 2351338 A US2351338 A US 2351338A
- Authority
- US
- United States
- Prior art keywords
- tanning
- diglycollic
- aldehyde
- methoxy
- hydroxymethyl
- 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
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C3/00—Tanning; Compositions for tanning
- C14C3/02—Chemical tanning
- C14C3/08—Chemical tanning by organic agents
- C14C3/16—Chemical tanning by organic agents using aliphatic aldehydes
Definitions
- This invention relates to the taming of hides and skins for the production of leather by the application thereto of a new taming agent.
- the invention deals with the degras or with sulfonated vegetable oils to pro prise soft and well-tanned leather.
- My invention is particularly well suited for the production of lightleathers from calf skins, kid, sheep and other hides of relatively light weight.
- the tanning is carried out simply by contacting the hides or skins, preferably in an unhaired and bated condition, with an aqueous solution of the tanning agent for a sufilcient time to complete the tanning.
- D methoxy D-hydroxymethyl diglycollic aldehyde has the structural formula:
- Example Depickled kid skins having a. pH of 4.0-6.5 were immersed in solutions containing 200% of water, 6% of salt and 7-15% of D'-methoxy- D-hydroxymethyl diglycollic aldehyde, all based on the weight of the skins. The skins were agitated in this solution for 8 hours, or until the tannage was complete, after which they were washed with water and dried. The dried leather was a light pink in color, but upon storage for several days this became a light tan.
- the D-methoxy- D-hydroxymethyl diglycollic aldehyde was prepared by the following process: 250 parts by weight of dextrose were heated with 440 parts by weight of benzene in a dehydrating apparatus for 2.5 hours, which resulted in the removal of 21.8 parts of water. After removing the benzene the dry residue was dissolved in 360 parts by weight of absolute methanol to which 15 parts of dry hydrogen chloride had been added and heated under a reflux condenser for 6 parts of decolorizing carbon were then added and the boiling continued minutes longer. The solution was filtered hot, cooled to 5 C., and the alpha-methyl glucopyranoside recovered by crystallization.
- a method of tanning hides and skins which comprises impregnating them with a solution containing D'-methoxy-D-hydroxymethyl diglycollic aldehyde.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
Description
Patented June 13, 1944 OFFICE TANNING WITH D -METHOXY-D-HYDROXY- METHYL DIGLYCOLLIC ALDEHYDE Kenneth L. Howard, Old Greenwich. Conn. as-
signor to American Cyanamid Company, New York, N. Y.. a corporation of Maine No Drawing. Application August 2, 1943, Serial No. 497,058
1 Claim. (Cl. 8-94.33)
This invention relates to the taming of hides and skins for the production of leather by the application thereto of a new taming agent.
More particularly, the invention deals with the degras or with sulfonated vegetable oils to pro duce soft and well-tanned leather. My invention is particularly well suited for the production of lightleathers from calf skins, kid, sheep and other hides of relatively light weight. The tanning is carried out simply by contacting the hides or skins, preferably in an unhaired and bated condition, with an aqueous solution of the tanning agent for a sufilcient time to complete the tanning.
D methoxy D-hydroxymethyl diglycollic aldehyde has the structural formula:
To the best of my knowledge, it is the first sugar dialdehyde that has shown satisfactory tanning properties. It is prepared according to known methods by the oxidation of alpha-methyl glucopyranoside with lead tetraacetate, and since the alpha-methyl glucopyranoside is readily obtainable from dextrose by the addition of methyl alcohol it is evident that the tanning agent is four hours.
readily obtainable in large quantities from relatively cheap raw materials.
My invention will be further illustrated by the following specific example to which, however, it is not limited.
Example Depickled kid skins having a. pH of 4.0-6.5 were immersed in solutions containing 200% of water, 6% of salt and 7-15% of D'-methoxy- D-hydroxymethyl diglycollic aldehyde, all based on the weight of the skins. The skins were agitated in this solution for 8 hours, or until the tannage was complete, after which they were washed with water and dried. The dried leather was a light pink in color, but upon storage for several days this became a light tan.
The D-methoxy- D-hydroxymethyl diglycollic aldehyde was prepared by the following process: 250 parts by weight of dextrose were heated with 440 parts by weight of benzene in a dehydrating apparatus for 2.5 hours, which resulted in the removal of 21.8 parts of water. After removing the benzene the dry residue was dissolved in 360 parts by weight of absolute methanol to which 15 parts of dry hydrogen chloride had been added and heated under a reflux condenser for 6 parts of decolorizing carbon were then added and the boiling continued minutes longer. The solution was filtered hot, cooled to 5 C., and the alpha-methyl glucopyranoside recovered by crystallization.
25 parts by weight of the glucopyranoside were dissolved in parts of water and 22 parts of lead tetraacetate in 52 parts of glacial acetic acid were added while maintaining the temperature below 40 C. An additional parts of lead tetraacetate were then added over a 45 minute period'after which the solution was stirred for one hour. The solution was decanted and treated with sulfuric acid to precipitate lead, filtered, and the filtrate evaporated under reduced pressure at 40-50 C.
Equally good results were obtained by oxidizing the alpha-methyl glucopyranoside with Pb3o-i in glacial acetic acid.
What I claim is:
A method of tanning hides and skins which comprises impregnating them with a solution containing D'-methoxy-D-hydroxymethyl diglycollic aldehyde.
KENNETH L. HOWARD.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US497058A US2351338A (en) | 1943-08-02 | 1943-08-02 | Tanning with d'-methoxy-d-hydroxymethyl diglycollic aldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US497058A US2351338A (en) | 1943-08-02 | 1943-08-02 | Tanning with d'-methoxy-d-hydroxymethyl diglycollic aldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2351338A true US2351338A (en) | 1944-06-13 |
Family
ID=23975292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US497058A Expired - Lifetime US2351338A (en) | 1943-08-02 | 1943-08-02 | Tanning with d'-methoxy-d-hydroxymethyl diglycollic aldehyde |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2351338A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2516283A (en) * | 1947-03-20 | 1950-07-25 | Adolph H Winheim | Resin impregnation of a dialdehyde tanned hide |
| US2581512A (en) * | 1948-07-10 | 1952-01-08 | Earl Hovey C | Soil scarifier |
| US3027221A (en) * | 1959-09-16 | 1962-03-27 | Clarence W Beebe | Rapid tannage of sole leather |
| WO1992013105A1 (en) * | 1991-01-29 | 1992-08-06 | Basf Aktiengesellschaft | Method of self-tanning, pre-tanning and co-tanning skins and hides and for retanning leather and hides |
-
1943
- 1943-08-02 US US497058A patent/US2351338A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2516283A (en) * | 1947-03-20 | 1950-07-25 | Adolph H Winheim | Resin impregnation of a dialdehyde tanned hide |
| US2581512A (en) * | 1948-07-10 | 1952-01-08 | Earl Hovey C | Soil scarifier |
| US3027221A (en) * | 1959-09-16 | 1962-03-27 | Clarence W Beebe | Rapid tannage of sole leather |
| WO1992013105A1 (en) * | 1991-01-29 | 1992-08-06 | Basf Aktiengesellschaft | Method of self-tanning, pre-tanning and co-tanning skins and hides and for retanning leather and hides |
| US5372609A (en) * | 1991-01-29 | 1994-12-13 | Basf Aktiengesellschaft | Self-tanning, pretanning and assist tanning of pelts and skin pelts and retanning of leather and skin |
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