US3716063A - Selective gas phase filter material - Google Patents
Selective gas phase filter material Download PDFInfo
- Publication number
- US3716063A US3716063A US00075773A US3716063DA US3716063A US 3716063 A US3716063 A US 3716063A US 00075773 A US00075773 A US 00075773A US 3716063D A US3716063D A US 3716063DA US 3716063 A US3716063 A US 3716063A
- Authority
- US
- United States
- Prior art keywords
- carrier
- poly
- buffered
- per gram
- alkyleneimine
- 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
Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/06—Use of materials for tobacco smoke filters
- A24D3/14—Use of materials for tobacco smoke filters of organic materials as additive
Definitions
- the invention is related to a tobacco smoke filter material.
- a porous particulate material for selectively removing smoke acidsand aldehydes.
- disperse 1 various materials such as amines and/or amine salts, on conventional filter tows (see U.S. Pat. No. 3,410,282) to selectively remove smoke acids from tobacco smoke.
- U.S. Pat. No. 3,410,282 See U.S. Pat. No. 3,410,282
- an improved tobacco smoke filter material which comprises a porous particulate carrier impregnated with an additive having an affinity for volatile smoke acids and aldehydes, wherein each of the said carrier particles has a pore' diameter of from about 0.l to 2.0 microns, a surfacearea offrom about I to square meters per gram and a pore volume no less than -about0.3 cubic'centimeterper gram. It has been should be no less than about 0.3 cubic centimeter per gram (cc/gm). Below this level selective removal of smoke stream acids and, particularly, aldehydes is significantly diminished.
- the porous carrier should have a pore volume of no less than 0.3 cubic centimeter per gram, when sufficient loadings of additive are incorporated on the carrier to effectively reduce smoke acids and aldehydes.
- Porous carriers with the above pore sizes and pore volumes have surface areas in the range from about I to 15 square meters per gram (m /gm). This is to be contrasted with conventional commercial adsorbent materials with surface areas of greater than 200 square meters per gram. Such commercial materials have been found to be relatively poor substrates for the additive described herein.
- the additive employed should have an affinity for volatile acids and aldehydes entrained in a tobacco smoke stream.
- the additive may be an amine at least partially buffered by a carboxylic' acid.
- the carboxylic acid salts are prepared by reacting primary or secondary alkyl and hydroxyalkyl amines with the acid. Some amines which have been found particularly effective include: ethylamine, dibutylamine, ethylenediamine,
- buffered poly(alkylcneimines) supported on i a porous alumina substrate having the aforesaid physical characteristics provide highly efficient filter m' ateri- 'als for the selective removal of volatile aldehydes, such as acetaldehyde and, acrolein, from cigarette smoke.
- the pore volume of the substrate preparation of the amine salts can be aliphatic or aromatic monoor polycarboxylic acids including the following: acetic, itaconic, lactict succinic, benzoic and cinnamic acids.
- carbonyl reactive materials which may be employed'as additives include phenylhydrazine, semicarbazide, thiosemicarbaz ide and the like.
- the porous car-rier for the additive can be any solid substrate capable of supporting the additive provided that the carrier has the previously specified dimensionalparameters.
- organic and inorganic materials may be employed.
- Typical carriers, also referred toherein as substrates, include: magnesite, zeolites, fullers earth diatomaceous earth, polyethylene granules, silica gel, and the like.
- Examplesof the filter material of the invention are produced by at least partially neutralizing each of the following organic bases with any of the following acids and,'thereafter, depositing the buffered additive on any of the following substrates:
- poly(alkyleneimines) are disclosed in U.S. Pat. No. 3,340,879 and, accordingly, the disclosure of the aforesaid patent is expressly incorporated herein.
- the poly(alkyleneimines) are at least partially neutralized or buffered with a carboxylic acid. Generally, alkanoic acids are preferred for this purpose.
- poly(ethyleneimine), at least partially buffered with acetic acid, is employed.
- the pH range of the additive is between about 6.0-and 7.6.
- poly(ethyleneimine) buffered with acetic acid it has been found that the optimum pH is 7.4.
- a particularly preferred alumina is produced by calcining the trihydrate at high temperatures (usually between about l,100 to 1,300 Centigrade).
- the particularly preferred filter materials of the invention are formed by buffering to a pH in the range from about 6.0 to 7.6 any of the following poly(alkyleneimines) V having the general formula: NH (CR CRC NH),.l-l where each R is individually selected from the class consisting of hydrogen, lower alkyl radicals free from aliphatic unsaturationand havingfrom one to six carbon atoms and n is a'whole number greater than 12, with any one ofthe following 'alkanoic acids and ,then.
- V having the general formula: NH (CR CRC NH),.l-l where each R is individually selected from the class consisting of hydrogen, lower alkyl radicals free from aliphatic unsaturationand havingfrom one to six carbon atoms and n is a'whole number greater than 12, with any one ofthe following 'alkanoic acids and ,then.
- caproic glutaric dimethyl- 3-n-pr0- pylaziridine) succinic Generally, for effective selective treatment of tobacco smoke according to the invention, at least about 2 percent by weight of additive based on the weight of the carrier is deposited on the carrier. Usually no more than about 6 percent by weight of additive is employed. Increasing the loading of additive has the effect of filling the pores of the carrier, thereby reducing selective removal of smoke stream components.
- the buffered additives are deposited on the above porous substrates by conventional techniques, for example, by immersing the carrier in the solution in which the additive has been prepared and, thereafter, evaporating the solvent. The substrate is then dried and formed into a filter.
- the filter material can be made in situ by at leastpartially neutralizing one of the above compounds with one of the above acids in the presence of a porous carrier.
- a filter is prepared by encasing the filter material of the invention in an outer wrapper.
- the resulting filter may be employed alone or in combination with conventional cellulose acetate filters.
- Triple filters employing, sequentially, the following filter sections: cellulose acetate, the filter material of the invention and cellulose acetate, have proven particularly workable.
- the filter material may be used in conjunction with perforated cigarette paper, if desired, or filter ventilation means may be employed.
- the filter material may be dispersed, in granular form, either on paper or cellulose acetate tow and encased in an outer wrapper.
- EXAMPLE I In order to illustrate the effectiveness of the filter material of the invention, an additive was prepared by buffering poly(ethyleneimine) with acetic acid to pH of 7.4. The amount of aceticacid used for this adjustment was 1.5 milliequivalents of acidv per gram of poly(ethyleneimine).
- the resulting buffered additive was deposited on selected porius aluminas. Their physical charac-. I
- sample A percent by weight of the buffered additive was deposited on the porous alumina substrate.
- Filter material was prepared fromsample B by depositing, respectively, 2 and 5 percent by weight of the additive on the porous alumina.
- sample C 2 percent by weight of additive was deposited on the porous alumina Predetermined quantities of the filter material were packed into 8 millimeter cavities between 7 and 6 millimeter lengths of conventional cellulose acetate filters of 84 millimeter cigarettes (tobacco sections 63 millimeters in length). The resulting cigarettes were smoked to 28 millimeter butt lengths on a constant vacuum smoking machine taking 35 milliliter puffs of 2 seconds duration at one minute intervals.
- the weight of the, filter 'material is expressed in .milligrams.
- the filter efficiency represents the weight percent of component trapped by the filter materials based on the total amount of the component enteringthe cigarette filter.
- any of the additive materials having an affinity for'vapor phase acids and aldehydes may bedeposited upon any of the porous carriers having the aforesaidphysical characteristics to form the filter material of the invention, with similar results.
- results set forth in the following table illustrate filter efficiencies of four different'porous aluminas, each deposited with 5 percent by weight of the above additive, wherein the mean pore diameter of the alumina carriers was in the range of from 0.1 to L8 microns. Pore volume and surface area were within the critical ranges.
- Filter material prepared from buffered PEI and deposited on conventional paper, sections ofqdual paper-cellulose acetate filters was also tested for vapor phase component removal. It was found that only about 25 percent acetaldehyde was selectively removedfrom cigarette smoke employing the dispersed additive.
- An improved tobacco smoke filter material comprising at least mg. of a porous particulate carrier impregnated with a poly(alkyleneimine) alkanoate, wherein from about 2 to 6 percent by weight alkanoate is deposited on the carrier based on the total weight-of the alkanoate and carrier, said poly(alkyleneimine) alkanoate having a pH from about 6.0 to 7.6, and wherein each of said carrier particles has a pore diameter of from about 0.1 to 2.0 microns, a surface area of from about 1 to 15 square meters per gram and a pore volume no less than about 0.3 cubic centimeter per' gram.
- An improved filter adapted to be affixed to a cigarette and comprising, in combination: a filter outer wrap having a tubular configuration and an inner filler formed from a .plurality of particles formed from a porous particulate carrier impregnated with an alkanoic acid buffered poly(alkyleneimine) additive, said additive buffered to a pH from about 6.0 to 7.6, from about 2 to 6 percent by weightadditive deposited on the 'carrier based on the total weight of carrier and additive, wherein from about 100 to milligrams of filler are employed in said filter and wherein the carrier particles each'have a pore diameter fromabout 0.1 to 2.0 microns, a surface area of from about 1 to 15 square meters per gram and a pore volume no less than about 0.3 cubic centimeter per gram.
- An improved tobacco smoke filter material comprising at least 100 mg. of a porous particulate carrier impregnated-with a poly(alkyleneimine) buffered with an alkanoic acid to a pH from about 6.0 to 7.6, wherein from about 2 m6 percent by weight buffered poly(alkyleneimine) is deposited on the carrier based on the total weight of the buffered poly(alkyleneimine) and carrier and wherein the carrier particles each have a pore diameter from about 0.1 to 2.0 microns, a surface area of from about 1 to 15 square meters per gram and a pore volume no less than about 0.3 cubic centimeter per gram.
- An improved tobacco smoke filter material adapted to be affixed to a cigarette and comprising: at least 100 milligrams of a porous alumina impregnated with poly(ethyleneimine) buffered to a pH of 7.4 with acetic acid, wherein the porous alumina has a pore diameter of from about 0.1 to 2.0 microns, a surface area of from about 1 to square meters per gram, a pore volume of from 0.3 to 0.8 cubic centimeter per gram and wherein from about 4 to 6 percent by weight buffered poly(ethyleneimine) is deposited on the porous alumina.
- An improved filter adapted to be affixed to a cigarette and comprising, in combination: a filter outer wrap having a tubular configuration and an inner filler formed from a plurality of particles formed from at least 100 milligrams of a porous particulate carrier impregnated with a poly(alkyleneimine) buffered with an alkanoic acid wherein from about 2 to 6 percent by weight acid buffered poly(alkyleneimine) is deposited on the carrier base on the total weight of the poly(alkyleneimine) and carrier, said poly(alkyleneimine) being buffered to a pH from about 6.0 to 7.6 and having an affinity for volatile smoke aldehydes and acids, wherein the carrier particles each have a pore diameter from about 0.1 to 2.0 microns, a surface area of from about 1 to 15 square meters per gram and a pore volume no less than about 0.3 cubic centimeter per gram.
- line 40 "NI-I (CR CRC NH) H" should be --NH (CR CR NH) H7 Col. 5, second chart, there should be a space between the third and fourth lines and a space between the fifth and sixth lines;
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Cigarettes, Filters, And Manufacturing Of Filters (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Filtering Materials (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7577370A | 1970-09-25 | 1970-09-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3716063A true US3716063A (en) | 1973-02-13 |
Family
ID=22127888
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00075773A Expired - Lifetime US3716063A (en) | 1970-09-25 | 1970-09-25 | Selective gas phase filter material |
Country Status (14)
Country | Link |
---|---|
US (1) | US3716063A (nl) |
AR (1) | AR192895A1 (nl) |
AU (1) | AU446175B2 (nl) |
BE (1) | BE773077A (nl) |
BR (1) | BR7106323D0 (nl) |
CA (1) | CA944249A (nl) |
DE (1) | DE2148035C3 (nl) |
DK (1) | DK133456B (nl) |
FI (1) | FI52166C (nl) |
GB (1) | GB1313259A (nl) |
MY (1) | MY7300479A (nl) |
NL (1) | NL152443B (nl) |
SE (1) | SE376541B (nl) |
ZA (1) | ZA716419B (nl) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4091822A (en) * | 1975-04-25 | 1978-05-30 | Loews Theatres, Inc. | Article for the selective removal of hydrogen cyanide from tobacco smoke |
US5009239A (en) * | 1988-12-20 | 1991-04-23 | Hoechst Celanese Corporation | Selective delivery and retention of aldehyde and nicotine by-product from cigarette smoke |
US5423336A (en) * | 1992-02-25 | 1995-06-13 | H.F. & Ph.F. Reemtsma Gmbh & Co. | Ventilated filter cigarette |
US6209547B1 (en) | 1998-10-29 | 2001-04-03 | Philip Morris Incorporated | Cigarette filter |
US6289898B1 (en) | 1999-07-28 | 2001-09-18 | Philip Morris Incorporated | Smoking article wrapper with improved filler |
US6481442B1 (en) * | 2000-11-28 | 2002-11-19 | Lorillard Licensing Company, Llc | Smoking article including a filter for selectively removing carbonyls |
US20040016436A1 (en) * | 2002-07-26 | 2004-01-29 | Charles Thomas | Adsorbents for smoking articles comprising a non-volatile organic compound applied using a supercritical fluid |
US20040173227A1 (en) * | 2003-02-18 | 2004-09-09 | Von Borstel Reid | Filter containing a metal phthalocyanine and a polycationic polymer |
US6848450B2 (en) * | 2000-02-07 | 2005-02-01 | Philip Morris Usa Inc. | Cigarette filter using intermetallic compounds |
US6911189B1 (en) | 1999-10-29 | 2005-06-28 | Philip Morris Usa Inc. | Filter for selective removal of a gaseous component |
US20050205102A1 (en) * | 2004-01-30 | 2005-09-22 | Philip Morris Usa Inc. | Method of making surface modified silica gel |
US7216652B1 (en) | 1999-07-28 | 2007-05-15 | Philip Morris Usa Inc. | Smoking article wrapper with improved filler |
WO2007121439A2 (en) * | 2006-04-17 | 2007-10-25 | Filligent Limited | Method and device for making tobacco smoke filters |
CN101433371B (zh) * | 2008-12-19 | 2011-10-12 | 湖南中烟工业有限责任公司 | 一种降低卷烟烟气中醛类物质的纸质过滤嘴及其制备方法 |
CN102948925A (zh) * | 2012-11-27 | 2013-03-06 | 湖南中烟工业有限责任公司 | 一种卷烟烟气重金属吸附剂的应用方法 |
CN102960860A (zh) * | 2012-11-27 | 2013-03-13 | 湖南中烟工业有限责任公司 | 一种通过化学交联得到的卷烟烟气重金属吸附剂的应用方法 |
CN104116133A (zh) * | 2014-07-31 | 2014-10-29 | 云南中烟工业有限责任公司 | 一种富含氨基基团的聚合物在纸质滤棒中的应用 |
CN106954891A (zh) * | 2017-04-10 | 2017-07-18 | 滁州卷烟材料厂 | 一种用于吸附卷烟烟气中重金属的滤嘴 |
WO2018089968A1 (en) * | 2016-11-14 | 2018-05-17 | Georgia Tech Research Corporation | Pcstructures including supported polyamines and methods of making the supported polyamines |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA792187B (en) * | 1978-05-16 | 1980-05-28 | British American Tobacco Co | Tobacco smoke filters |
FR2905628B1 (fr) * | 2006-09-13 | 2011-01-21 | Rhodia Recherches & Tech | Materiau composite de cohesion elevee, procede de preparation et utilisations, notamment dans les filtres a cigarettes. |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3340879A (en) * | 1967-01-16 | 1967-09-12 | Brown & Williamson Tobacco | Cigarette filters |
US3410282A (en) * | 1967-03-13 | 1968-11-12 | Eastman Kodak Co | Filter medium for removing hydrogen cyanide from tobacco smoke |
US3434479A (en) * | 1966-09-15 | 1969-03-25 | Liggett & Myers Tobacco Co | Permanganate tobacco smoke filter |
-
1970
- 1970-09-25 US US00075773A patent/US3716063A/en not_active Expired - Lifetime
-
1971
- 1971-07-30 CA CA119,545A patent/CA944249A/en not_active Expired
- 1971-08-24 GB GB3969071A patent/GB1313259A/en not_active Expired
- 1971-09-20 FI FI712620A patent/FI52166C/fi active
- 1971-09-23 NL NL717113122A patent/NL152443B/nl not_active IP Right Cessation
- 1971-09-23 AU AU33840/71A patent/AU446175B2/en not_active Expired
- 1971-09-23 AR AR238125A patent/AR192895A1/es active
- 1971-09-24 SE SE7112145A patent/SE376541B/xx unknown
- 1971-09-24 BR BR6323/71A patent/BR7106323D0/pt unknown
- 1971-09-24 BE BE773077A patent/BE773077A/xx not_active IP Right Cessation
- 1971-09-24 DK DK466971AA patent/DK133456B/da not_active IP Right Cessation
- 1971-09-24 ZA ZA716419A patent/ZA716419B/xx unknown
- 1971-09-25 DE DE2148035A patent/DE2148035C3/de not_active Expired
-
1973
- 1973-12-30 MY MY479/73A patent/MY7300479A/xx unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3434479A (en) * | 1966-09-15 | 1969-03-25 | Liggett & Myers Tobacco Co | Permanganate tobacco smoke filter |
US3340879A (en) * | 1967-01-16 | 1967-09-12 | Brown & Williamson Tobacco | Cigarette filters |
US3410282A (en) * | 1967-03-13 | 1968-11-12 | Eastman Kodak Co | Filter medium for removing hydrogen cyanide from tobacco smoke |
Cited By (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4091822A (en) * | 1975-04-25 | 1978-05-30 | Loews Theatres, Inc. | Article for the selective removal of hydrogen cyanide from tobacco smoke |
US5009239A (en) * | 1988-12-20 | 1991-04-23 | Hoechst Celanese Corporation | Selective delivery and retention of aldehyde and nicotine by-product from cigarette smoke |
US5423336A (en) * | 1992-02-25 | 1995-06-13 | H.F. & Ph.F. Reemtsma Gmbh & Co. | Ventilated filter cigarette |
US6209547B1 (en) | 1998-10-29 | 2001-04-03 | Philip Morris Incorporated | Cigarette filter |
US6595218B1 (en) | 1998-10-29 | 2003-07-22 | Philip Morris Incorporated | Cigarette filter |
US6289898B1 (en) | 1999-07-28 | 2001-09-18 | Philip Morris Incorporated | Smoking article wrapper with improved filler |
US7216652B1 (en) | 1999-07-28 | 2007-05-15 | Philip Morris Usa Inc. | Smoking article wrapper with improved filler |
US6911189B1 (en) | 1999-10-29 | 2005-06-28 | Philip Morris Usa Inc. | Filter for selective removal of a gaseous component |
US6848450B2 (en) * | 2000-02-07 | 2005-02-01 | Philip Morris Usa Inc. | Cigarette filter using intermetallic compounds |
US6481442B1 (en) * | 2000-11-28 | 2002-11-19 | Lorillard Licensing Company, Llc | Smoking article including a filter for selectively removing carbonyls |
US20040016436A1 (en) * | 2002-07-26 | 2004-01-29 | Charles Thomas | Adsorbents for smoking articles comprising a non-volatile organic compound applied using a supercritical fluid |
US20090272391A1 (en) * | 2002-07-26 | 2009-11-05 | Charles Thomas | Adsorbents for smoking articles comprising a non-volatile organic compound applied using a supercritical fluid |
US8114475B2 (en) | 2002-07-26 | 2012-02-14 | Philip Morris Usa Inc. | Adsorbents for smoking articles comprising a non-volatile organic compound applied using a supercritical fluid |
EP1594376A2 (en) * | 2003-02-18 | 2005-11-16 | Filligent Limited | Filter containing a metal phthalocyanine and a polycationic polymer |
EP1594376A4 (en) * | 2003-02-18 | 2006-01-18 | Filligent Ltd | FILTER CONTAINS A METAL PHTHALOCYANINE AND A POLYMER POLYMER |
US20040173227A1 (en) * | 2003-02-18 | 2004-09-09 | Von Borstel Reid | Filter containing a metal phthalocyanine and a polycationic polymer |
US20050205102A1 (en) * | 2004-01-30 | 2005-09-22 | Philip Morris Usa Inc. | Method of making surface modified silica gel |
AU2007237935B2 (en) * | 2006-04-17 | 2012-03-15 | Filligent Limited | Method and device for making tobacco smoke filters |
US20090025736A1 (en) * | 2006-04-17 | 2009-01-29 | Filligent Limited | Method and device for making tobacco smoke filters |
WO2007121439A3 (en) * | 2006-04-17 | 2008-10-23 | Filligent Ltd | Method and device for making tobacco smoke filters |
WO2007121439A2 (en) * | 2006-04-17 | 2007-10-25 | Filligent Limited | Method and device for making tobacco smoke filters |
CN101433371B (zh) * | 2008-12-19 | 2011-10-12 | 湖南中烟工业有限责任公司 | 一种降低卷烟烟气中醛类物质的纸质过滤嘴及其制备方法 |
CN102960860B (zh) * | 2012-11-27 | 2014-04-16 | 湖南中烟工业有限责任公司 | 一种通过化学交联得到的卷烟烟气重金属吸附剂的应用方法 |
CN102960860A (zh) * | 2012-11-27 | 2013-03-13 | 湖南中烟工业有限责任公司 | 一种通过化学交联得到的卷烟烟气重金属吸附剂的应用方法 |
CN102948925A (zh) * | 2012-11-27 | 2013-03-06 | 湖南中烟工业有限责任公司 | 一种卷烟烟气重金属吸附剂的应用方法 |
CN102948925B (zh) * | 2012-11-27 | 2014-06-11 | 湖南中烟工业有限责任公司 | 一种卷烟烟气重金属吸附剂的应用方法 |
CN104116133A (zh) * | 2014-07-31 | 2014-10-29 | 云南中烟工业有限责任公司 | 一种富含氨基基团的聚合物在纸质滤棒中的应用 |
WO2018089968A1 (en) * | 2016-11-14 | 2018-05-17 | Georgia Tech Research Corporation | Pcstructures including supported polyamines and methods of making the supported polyamines |
US11446634B2 (en) | 2016-11-14 | 2022-09-20 | Georgia Tech Research Corporation | Pcstructures including supported polyamines and methods of making the supported polyamines |
US11794164B2 (en) | 2016-11-14 | 2023-10-24 | Georgia Tech Research Corporation | Pcstructures including supported polyamines and methods of making the supported polyamines |
CN106954891A (zh) * | 2017-04-10 | 2017-07-18 | 滁州卷烟材料厂 | 一种用于吸附卷烟烟气中重金属的滤嘴 |
Also Published As
Publication number | Publication date |
---|---|
DK133456C (nl) | 1976-10-18 |
SE376541B (nl) | 1975-06-02 |
DE2148035B2 (de) | 1980-06-12 |
DE2148035C3 (de) | 1981-02-19 |
AU446175B2 (en) | 1974-03-14 |
CA944249A (en) | 1974-03-26 |
FI52166C (fi) | 1977-07-11 |
ZA716419B (en) | 1972-05-31 |
DE2148035A1 (de) | 1972-03-30 |
FI52166B (nl) | 1977-03-31 |
GB1313259A (en) | 1973-04-11 |
BR7106323D0 (pt) | 1973-05-08 |
BE773077A (fr) | 1972-03-24 |
AU3384071A (en) | 1973-03-29 |
NL152443B (nl) | 1977-03-15 |
AR192895A1 (es) | 1973-03-21 |
MY7300479A (en) | 1973-12-31 |
NL7113122A (nl) | 1972-03-28 |
DK133456B (da) | 1976-05-24 |
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