CA1102965A - Fat-liquoring process - Google Patents
Fat-liquoring processInfo
- Publication number
- CA1102965A CA1102965A CA312,481A CA312481A CA1102965A CA 1102965 A CA1102965 A CA 1102965A CA 312481 A CA312481 A CA 312481A CA 1102965 A CA1102965 A CA 1102965A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- oil
- hydroxylated
- phosphatide
- leather
- 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
Links
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
- C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
- C14C9/02—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes using fatty or oily materials, e.g. fat liquoring
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
Abstract
Abstract of the Invention Hydroxylated phosphatides are used as component in or as the sole fattening agent in fat-liquoring.
The hydroxylated phosphatide penetrates throughout the whole thickness of the leather, as opposed to non-modified phosphatides, giving the leather suppleness and softness. Rest fat content in the liquoring bath is low.
The hydroxylated phosphatide penetrates throughout the whole thickness of the leather, as opposed to non-modified phosphatides, giving the leather suppleness and softness. Rest fat content in the liquoring bath is low.
Description
Z 25~ ~R~
6~i The invention relates to a process for fat-liquoring tanned leather. In the technical process for converting hides and skin to leather, one of the steps is the fat-liquoring step. In this step the tanned leather is contacted with an aqueous emulsion of a fatty substance. After tanning, which serves to remove all undesirable substances from the leather, the leather is hard and stiff. The fat-liquoring serves to introduce a fatty substance into the fibre structure of the leather. The fatty substance has lubricating properties which impart to the leather suppleness, elasticity, strength and feel.
To fulfil the above functions, the fatty substance must be able to penetrate throughout the whole thickness of the leather and moreover be chemically or physically bound in the leather to prevent sweating out. To obtain this fixation, the fatty substance should contain polar groups.
The most used method for introducing the fatty substance is fat-liquoring. In this method the leather is contacted with an aqueous emulsion of the fatty substance. From an economical point of view it is also important that the leather should take up most of the fatty substance from the liquoring bath, i.e. the residual fat content of the liquor should be as low as possible to avoid undesirable losses.
As fatty substahces sulphonated mineral, vegetable and animal oils are mostly used, often in admixture with non~
.~
sulphonated oils. Examples of such oils are Turkey red oil, sulphonated train oil, sulphonated sperm oil, neatsfoot oil, sulphonated fatty alcohols and also partially chlorinated,
6~i The invention relates to a process for fat-liquoring tanned leather. In the technical process for converting hides and skin to leather, one of the steps is the fat-liquoring step. In this step the tanned leather is contacted with an aqueous emulsion of a fatty substance. After tanning, which serves to remove all undesirable substances from the leather, the leather is hard and stiff. The fat-liquoring serves to introduce a fatty substance into the fibre structure of the leather. The fatty substance has lubricating properties which impart to the leather suppleness, elasticity, strength and feel.
To fulfil the above functions, the fatty substance must be able to penetrate throughout the whole thickness of the leather and moreover be chemically or physically bound in the leather to prevent sweating out. To obtain this fixation, the fatty substance should contain polar groups.
The most used method for introducing the fatty substance is fat-liquoring. In this method the leather is contacted with an aqueous emulsion of the fatty substance. From an economical point of view it is also important that the leather should take up most of the fatty substance from the liquoring bath, i.e. the residual fat content of the liquor should be as low as possible to avoid undesirable losses.
As fatty substahces sulphonated mineral, vegetable and animal oils are mostly used, often in admixture with non~
.~
sulphonated oils. Examples of such oils are Turkey red oil, sulphonated train oil, sulphonated sperm oil, neatsfoot oil, sulphonated fatty alcohols and also partially chlorinated,
- 2 -.
: ' ' ' ' '' ' ' ' ' ' `
, ' ` , , . ' .
Z 254 (R~
~2~
sulphonated or oxidised fats and fatty oils.
In carrying out the fat-liquoring the leather is contacted at about 30 to 60C with 100 to 200% by weight of water containing 5 to 10% by weight of the fat, both percentages being calculated on the weight of the leather. The liquoring is continued until the maximum amount of fat has be-en taken up by the leather, which usually takes about 40 to 60 minutes.
It has been proposed (~rench Patent Specification 647,Ll56) to use phosphatides in fat-liquoring because of its 10 emulsifying properties and it was claimed that said phosphatides would assist in the penetration of the fat into the leather and would increase its fat uptake.
However, in practice the use of phosphatides in fat-liquoring has been very restricted~ due to the fact that 15 they are insufficiently taken up by the leather, leading to insufficient fattening of the interîor of the leather. Such insufficient fattening leaves the leather too hard and too stiff. Moreover the poor fat uptake leads to high rest contents of fat in the liquor and hence to high fat losses.
It has now been found that hydroxylated phosphatides are eminently suitable ~or use as the fatty substance in fat liquors ~for fattening leather. In contrast to non-modified phosphatides, the hydroxylated phosphatides penetratethrough-out the thlckness of the leather and they are almost 25 completely taken up by the leather from the fat-liquor, making the rest content in the iiquorine bath very low.
Therefore~the present invention provides a process for fat-liquoring tanned leather with an aqueous emulsion of a '''
: ' ' ' ' '' ' ' ' ' ' `
, ' ` , , . ' .
Z 254 (R~
~2~
sulphonated or oxidised fats and fatty oils.
In carrying out the fat-liquoring the leather is contacted at about 30 to 60C with 100 to 200% by weight of water containing 5 to 10% by weight of the fat, both percentages being calculated on the weight of the leather. The liquoring is continued until the maximum amount of fat has be-en taken up by the leather, which usually takes about 40 to 60 minutes.
It has been proposed (~rench Patent Specification 647,Ll56) to use phosphatides in fat-liquoring because of its 10 emulsifying properties and it was claimed that said phosphatides would assist in the penetration of the fat into the leather and would increase its fat uptake.
However, in practice the use of phosphatides in fat-liquoring has been very restricted~ due to the fact that 15 they are insufficiently taken up by the leather, leading to insufficient fattening of the interîor of the leather. Such insufficient fattening leaves the leather too hard and too stiff. Moreover the poor fat uptake leads to high rest contents of fat in the liquor and hence to high fat losses.
It has now been found that hydroxylated phosphatides are eminently suitable ~or use as the fatty substance in fat liquors ~for fattening leather. In contrast to non-modified phosphatides, the hydroxylated phosphatides penetratethrough-out the thlckness of the leather and they are almost 25 completely taken up by the leather from the fat-liquor, making the rest content in the iiquorine bath very low.
Therefore~the present invention provides a process for fat-liquoring tanned leather with an aqueous emulsion of a '''
- 3 "- , - . : ~, . ,, .
' ~' ' '' ' ' ' ', ~ , '' .: : -~ Z 25~ (P) fatty substance comprising a phosphatide, which process is characterized in that as the phosphatide a hydroxylated phosphatide is used. Preferably, the fatty substance comprises 30 to 100% by weight, more preferably 70 to 100% by weight of the hydroxylated phosphatide.
- Preferably as the fatty substance a mixture of hydroxy-lated phosphatides is used, as obtained by hydroxylating a vegetable phosphatide mixture, separated from a vegetable oil, such as soyabean oil, peanut oil, rapeseed oil, cottonseed oil, etc. by a suitable degumming process; for instance by treatment of the oil with water or steam. Especially soyabean --phosphatides are being preferred because of their general availability.
Further, phosphatides which before or after the hydroxy-lation have been modified in other ways can be used. Especi-ally useful in this respect are phosphatides which before or after the hydroxylation have been subjected to a partial hydrolysis by treatment with an acid, a base or an enzyme such as phospholipase A. Preferably, hydroxylated phosphatides are used which have been hydroxylated until the iodine value has decreased by 5 to 25%.
: Also phosphatide fractions obtained by fractionation of crude or modified phosphatide mixtures with a solvent or a mixture of solvents may be used as the starting material for the hydroxylation; also the hydroxylated phosphatide mixture can be fractionated, and one or both of the fractions be used as the fattening agent of the invention.
The fatty substance additionally may comprise oils which are custo-marily used in the art of fat-liquoring, such as neatsfoot oil, sperm oil, and/or sulphonated sperm oil. Alternatively the fatty substance may contain soyabean oil.
~ -4-~" `
,;, Z 254 (R) ~or use with chromium-tanned leather it is desirable that the fattening mixture of the invention should contain a substance which increases its chromium resistance. ~s such substances ethoxylated alkyl phenols may be used, such as an ethoxylated nonyl phenol, availab]e under the trade name Arkopal -N 150 ~ from ~arbwer~e ~loechst, ~ermany. When used, the amount of the chromium resistance lncreasing agent added is usually about 3 to 15% by weight, pre~erably 3 to 10%, and more preferably about 4 to 6%, calculated on the total fattening mixture. Also the salt stability of the fattening mixture is increased by such agents. Opt;ionally an emulsifier may be added.
Process for hydroxylating phosphatides are described in USP 2,445,948 and in USP 2,629,662. In said process the phosphatides are reacted with an oxidising agent, preferably hydrogen peroxide, optionally in the presence of an acid, such as acetic acid, however preferably lactic acid, serving as a catalyst. By the reaction double bonds contained in the fatty acid chains of the phosphatides are converted to glycolic hydroxyl groups,some of which may be esterified with acylgroups. By this pxocess the iodine value of the phosphatides, which for scyabean phosphatides ls originally about 95 to 100, is decreased by 5 to 25%.
The phosphatide fattening agents of the invention are used in substantially the same way as the fattening agents customarily used in fat-liquoring of leather, viz. in a rotating container the leather is contacted at 40 to 69C
with 100 to 200~ by weight of water containing 5 to 10% by ~ 5 -. .
.
Z ~54 (R) weight of the phosphatide fattening agent ufftil the desired degree of fattening is reached.
The fattening agent of the invention can be used for fat-liquoring ali kinds of leather, such as buckskin, split upper leather, vegetable tanned leather~ grain leather, suède etc.
Example A number of chromium-tanned wet-blue cow hides were shaved to a thickness of 1.6 mm. The hides contained 5.9%
Cr203g calculated on the dry matter, and their pH was 3.3.
The hides were brought into a rotating container and 200%
by weight of water of 55C was added. Then 2% by weight, calculated on the hides, of Tanigan PC ~ (a tanning agent Bayer, Germany) was added. Af`ter 10 minutes o.8% by weight of Luganilbraun NT ~ (a dyestuff of BASF, Germany) dissol~ed in 15 times its weight of water was added, followed, after a further 10 minutes~ by 6.3% by weight of a hydroxylated soyabean phosphatide mixture (iodine value 87.6 and containing 5% by weight of Arkopal-N 150,*an ethoxylated nonyl phenol of Farbwerke Hoechst, Germany), dispersed in 7 times its weight of water. The temperature .
of the liquoring bath was 38C and its pH 4.72. After 20 minutes a mixture of 2% by weight of wattle3 2% by weight of Tanigan PR ~ (a tanning agent of Bayer, Germany) and 2%
by weight of P.etingan R7 ~ (a kanning agent of Bayer, Germany) was added to the bathO After 15 minutes 0.15~ by weight of formic acid was added, and after a further 15 minutes the liquor was drained off. Next the hides were * trade mark Z 254 (P) washed with 400% by weight of water at 25C for 10 minutes, whereafter the hides were allowed to drip dry overnight.
Then the hides were pressed, vacuum-dried at 85C for 2.5 minutes and post~dried at 25-30C for 1.5 hours.
After a few days the hides were staked.
After the fattening step the liquor contained only 0.95 g/l of the phosphatides. In view of the fact that 50% of the 200% of water added had been taken up by the hides, this means that 98% of the phosphatides had been taken up by the leather. The fattened hides contained 8.5% by weight of the phosphatides, ca]culated on the dry leather (determined by extraction with methylenechloride).
The physical properties of the fattened hides ful-filled all the requirements of a good quality sides leather.
~ : .
,
' ~' ' '' ' ' ' ', ~ , '' .: : -~ Z 25~ (P) fatty substance comprising a phosphatide, which process is characterized in that as the phosphatide a hydroxylated phosphatide is used. Preferably, the fatty substance comprises 30 to 100% by weight, more preferably 70 to 100% by weight of the hydroxylated phosphatide.
- Preferably as the fatty substance a mixture of hydroxy-lated phosphatides is used, as obtained by hydroxylating a vegetable phosphatide mixture, separated from a vegetable oil, such as soyabean oil, peanut oil, rapeseed oil, cottonseed oil, etc. by a suitable degumming process; for instance by treatment of the oil with water or steam. Especially soyabean --phosphatides are being preferred because of their general availability.
Further, phosphatides which before or after the hydroxy-lation have been modified in other ways can be used. Especi-ally useful in this respect are phosphatides which before or after the hydroxylation have been subjected to a partial hydrolysis by treatment with an acid, a base or an enzyme such as phospholipase A. Preferably, hydroxylated phosphatides are used which have been hydroxylated until the iodine value has decreased by 5 to 25%.
: Also phosphatide fractions obtained by fractionation of crude or modified phosphatide mixtures with a solvent or a mixture of solvents may be used as the starting material for the hydroxylation; also the hydroxylated phosphatide mixture can be fractionated, and one or both of the fractions be used as the fattening agent of the invention.
The fatty substance additionally may comprise oils which are custo-marily used in the art of fat-liquoring, such as neatsfoot oil, sperm oil, and/or sulphonated sperm oil. Alternatively the fatty substance may contain soyabean oil.
~ -4-~" `
,;, Z 254 (R) ~or use with chromium-tanned leather it is desirable that the fattening mixture of the invention should contain a substance which increases its chromium resistance. ~s such substances ethoxylated alkyl phenols may be used, such as an ethoxylated nonyl phenol, availab]e under the trade name Arkopal -N 150 ~ from ~arbwer~e ~loechst, ~ermany. When used, the amount of the chromium resistance lncreasing agent added is usually about 3 to 15% by weight, pre~erably 3 to 10%, and more preferably about 4 to 6%, calculated on the total fattening mixture. Also the salt stability of the fattening mixture is increased by such agents. Opt;ionally an emulsifier may be added.
Process for hydroxylating phosphatides are described in USP 2,445,948 and in USP 2,629,662. In said process the phosphatides are reacted with an oxidising agent, preferably hydrogen peroxide, optionally in the presence of an acid, such as acetic acid, however preferably lactic acid, serving as a catalyst. By the reaction double bonds contained in the fatty acid chains of the phosphatides are converted to glycolic hydroxyl groups,some of which may be esterified with acylgroups. By this pxocess the iodine value of the phosphatides, which for scyabean phosphatides ls originally about 95 to 100, is decreased by 5 to 25%.
The phosphatide fattening agents of the invention are used in substantially the same way as the fattening agents customarily used in fat-liquoring of leather, viz. in a rotating container the leather is contacted at 40 to 69C
with 100 to 200~ by weight of water containing 5 to 10% by ~ 5 -. .
.
Z ~54 (R) weight of the phosphatide fattening agent ufftil the desired degree of fattening is reached.
The fattening agent of the invention can be used for fat-liquoring ali kinds of leather, such as buckskin, split upper leather, vegetable tanned leather~ grain leather, suède etc.
Example A number of chromium-tanned wet-blue cow hides were shaved to a thickness of 1.6 mm. The hides contained 5.9%
Cr203g calculated on the dry matter, and their pH was 3.3.
The hides were brought into a rotating container and 200%
by weight of water of 55C was added. Then 2% by weight, calculated on the hides, of Tanigan PC ~ (a tanning agent Bayer, Germany) was added. Af`ter 10 minutes o.8% by weight of Luganilbraun NT ~ (a dyestuff of BASF, Germany) dissol~ed in 15 times its weight of water was added, followed, after a further 10 minutes~ by 6.3% by weight of a hydroxylated soyabean phosphatide mixture (iodine value 87.6 and containing 5% by weight of Arkopal-N 150,*an ethoxylated nonyl phenol of Farbwerke Hoechst, Germany), dispersed in 7 times its weight of water. The temperature .
of the liquoring bath was 38C and its pH 4.72. After 20 minutes a mixture of 2% by weight of wattle3 2% by weight of Tanigan PR ~ (a tanning agent of Bayer, Germany) and 2%
by weight of P.etingan R7 ~ (a kanning agent of Bayer, Germany) was added to the bathO After 15 minutes 0.15~ by weight of formic acid was added, and after a further 15 minutes the liquor was drained off. Next the hides were * trade mark Z 254 (P) washed with 400% by weight of water at 25C for 10 minutes, whereafter the hides were allowed to drip dry overnight.
Then the hides were pressed, vacuum-dried at 85C for 2.5 minutes and post~dried at 25-30C for 1.5 hours.
After a few days the hides were staked.
After the fattening step the liquor contained only 0.95 g/l of the phosphatides. In view of the fact that 50% of the 200% of water added had been taken up by the hides, this means that 98% of the phosphatides had been taken up by the leather. The fattened hides contained 8.5% by weight of the phosphatides, ca]culated on the dry leather (determined by extraction with methylenechloride).
The physical properties of the fattened hides ful-filled all the requirements of a good quality sides leather.
~ : .
,
Claims (13)
AN EXCLUSIVE PROPERTY OR PRIVILEGE IS CLAIMED
ARE DEFINED AS FOLLOWS:
1. Process for fat-liquoring tanned leather with an aqueous emulsion of a fatty substance comprising a phosphatide, characterized in that as the phosphatide a hydroxylated phos-phatide is used.
2. Process according to claim 1, characterized in that the fatty substance comprises 30 to 100% by weight of the hydroxylated phosphatide.
3. Process according to claim 1, characterized in that a hydroxylated vegetable phosphatide mixture is used.
4. Process according to claims 1 to 3, characterized in that hydroxylated soyabean phosphatides are used.
5. Process according to claims l to 3, characterized in that a phosphatide is used which has been hydroxylated until the iodine value has decreased by 5 to 25%.
6. Process according to claims 1 to 3, characterized in that a partially hydrolysed, hydroxylated phosphatide is used.
7. Process according to claim 1, characterized in that additionally a fatty oil and/or sulphonated oil is used in the liquoring bath.
8. Process according to claim 7, characterized in that as the fatty oil soyabean oil is used.
9. Process according to claim 7, characterized in that as the sulphonated oil neatsfoot oil, sperm oil or sulphonated sperm oil is used.
10. Process according to claim 1, characterized in that a chromium resistance improving agent is added.
11. Process according to claim 10, characterized in that as the chromium resistance improving agent an ethoxylated alkylphenol is used.
12. Process according to claim 11, characterized in that as the chromium resistance improving agent 3 to 15% by weight of an ethoxylated nonylphenol is used, calculated on the fatty substance.
13. Process according to claims 1 to 3, characterized in that the liquoring bath contains an emulsifier.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB41,668/77 | 1977-10-06 | ||
| GB4166877 | 1977-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1102965A true CA1102965A (en) | 1981-06-16 |
Family
ID=10420760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA312,481A Expired CA1102965A (en) | 1977-10-06 | 1978-10-02 | Fat-liquoring process |
Country Status (12)
| Country | Link |
|---|---|
| AR (1) | AR214590A1 (en) |
| BE (1) | BE871072A (en) |
| BR (1) | BR7806651A (en) |
| CA (1) | CA1102965A (en) |
| DE (1) | DE2843755C3 (en) |
| DK (1) | DK443578A (en) |
| FR (1) | FR2405302A1 (en) |
| IE (1) | IE47293B1 (en) |
| IT (1) | IT1109569B (en) |
| NL (1) | NL176277C (en) |
| SE (1) | SE430793B (en) |
| ZA (1) | ZA785627B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3238180C1 (en) * | 1982-10-15 | 1984-04-19 | Schill & Seilacher GmbH & Co, 7030 Böblingen | Process for greasing leather and furs |
| DE3529073A1 (en) * | 1984-08-22 | 1986-02-27 | Sandoz-Patent-GmbH, 7850 Lörrach | Preparations containing phosphoric acid partial esters, their preparation and their use |
| DE10207277A1 (en) * | 2002-02-21 | 2003-09-04 | Basf Ag | Low-VOC greasing agents, their use in the production and / or treatment of leather and skins, and processes for the production and / or treatment of leather and skins with these greasing agents |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR642682A (en) * | 1927-03-22 | 1928-09-01 | Process for the preparation of special oils for buffing hides, wringing leathers, preparing rubble stone, etc. | |
| DE514399C (en) * | 1927-07-17 | 1930-12-11 | Bruno Rewald Dr | Preparations for greasing leather |
| FR647456A (en) * | 1927-09-06 | 1928-11-24 | Process for the manufacture of an ingredient which facilitates the tanning of leather | |
| DE516187C (en) * | 1927-09-07 | 1931-01-19 | Bruno Rewald Dr | Preparations for greasing leather |
| DE516188C (en) * | 1927-10-25 | 1931-01-19 | Bruno Rewald Dr | Preparations for greasing leather |
| DE522041C (en) * | 1927-12-06 | 1931-03-30 | Bruno Rewald Dr | Emulsifier for the production of an agent for greasing leather |
| DE516189C (en) * | 1927-12-25 | 1931-01-19 | Bruno Rewald Dr | Preparations for greasing leather |
| GB306672A (en) * | 1928-01-23 | 1929-02-28 | Hanseatische Muehlenwerke Ag | Improvements in or relating to processes for dressing leather, skins and the like |
| DE596576C (en) * | 1928-08-21 | 1934-05-05 | Oranienburger Chem Fab Akt Ges | Fatliquor for leather |
| GB464100A (en) * | 1935-10-08 | 1937-04-08 | Bruno Rewald | Improvements in and relating to phosphatide compositions |
| FR827822A (en) * | 1936-10-21 | 1938-05-04 | Chem Fab Gru Nau Landshoff & M | Process and product for feeding leather |
| GB643403A (en) * | 1940-05-11 | 1950-09-20 | Nopco Chem Co | Improvements relating to the production of blown fatty materials |
| US2445948A (en) * | 1944-12-04 | 1948-07-27 | Gen Mills Inc | Hydroxyphosphatides |
| US2629662A (en) * | 1948-06-17 | 1953-02-24 | Glidden Co | Process of treating phosphatides and product |
-
1978
- 1978-10-02 CA CA312,481A patent/CA1102965A/en not_active Expired
- 1978-10-02 IE IE1969/78A patent/IE47293B1/en unknown
- 1978-10-05 DK DK443578A patent/DK443578A/en not_active Application Discontinuation
- 1978-10-05 FR FR7828509A patent/FR2405302A1/en active Pending
- 1978-10-05 SE SE7810454A patent/SE430793B/en unknown
- 1978-10-05 ZA ZA785627A patent/ZA785627B/en unknown
- 1978-10-06 NL NLAANVRAGE7810085,A patent/NL176277C/en not_active IP Right Cessation
- 1978-10-06 IT IT69326/78A patent/IT1109569B/en active
- 1978-10-06 BR BR7806651A patent/BR7806651A/en unknown
- 1978-10-06 AR AR273982A patent/AR214590A1/en active
- 1978-10-06 BE BE190960A patent/BE871072A/en not_active IP Right Cessation
- 1978-10-06 DE DE2843755A patent/DE2843755C3/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2405302A1 (en) | 1979-05-04 |
| IE47293B1 (en) | 1984-02-08 |
| NL176277C (en) | 1985-03-18 |
| IT1109569B (en) | 1985-12-23 |
| DE2843755B2 (en) | 1980-07-31 |
| IT7869326A0 (en) | 1978-10-06 |
| DE2843755A1 (en) | 1979-04-12 |
| NL176277B (en) | 1984-10-16 |
| BE871072A (en) | 1979-04-06 |
| SE430793B (en) | 1983-12-12 |
| SE7810454L (en) | 1979-04-07 |
| DK443578A (en) | 1979-04-07 |
| ZA785627B (en) | 1980-05-28 |
| DE2843755C3 (en) | 1981-03-12 |
| NL7810085A (en) | 1979-04-10 |
| IE781969L (en) | 1979-04-06 |
| AR214590A1 (en) | 1979-06-29 |
| BR7806651A (en) | 1979-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |