JPS6024129B2 - グリオキサ−ル変性ポリ（β−アラニン）の製造方法 - Google Patents
グリオキサ−ル変性ポリ（β−アラニン）の製造方法Info
- Publication number
- JPS6024129B2 JPS6024129B2 JP52013096A JP1309677A JPS6024129B2 JP S6024129 B2 JPS6024129 B2 JP S6024129B2 JP 52013096 A JP52013096 A JP 52013096A JP 1309677 A JP1309677 A JP 1309677A JP S6024129 B2 JPS6024129 B2 JP S6024129B2
- Authority
- JP
- Japan
- Prior art keywords
- alanine
- poly
- glyoxal
- water
- modified
- 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
- -1 poly(β-alanine) Polymers 0.000 title claims description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 34
- 229920000642 polymer Polymers 0.000 claims description 28
- 239000007864 aqueous solution Substances 0.000 claims description 24
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 23
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
- 229940015043 glyoxal Drugs 0.000 claims description 17
- 125000000129 anionic group Chemical group 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 11
- 125000002091 cationic group Chemical group 0.000 claims description 11
- 239000003112 inhibitor Substances 0.000 claims description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 150000001408 amides Chemical group 0.000 claims 5
- 229920005989 resin Polymers 0.000 description 48
- 239000011347 resin Substances 0.000 description 48
- 239000000123 paper Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000003368 amide group Chemical group 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 229920003043 Cellulose fiber Polymers 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 230000003014 reinforcing effect Effects 0.000 description 5
- 238000005728 strengthening Methods 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000001749 primary amide group Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- TXPKUUXHNFRBPS-UHFFFAOYSA-N 3-(2-carboxyethylamino)propanoic acid Chemical compound OC(=O)CCNCCC(O)=O TXPKUUXHNFRBPS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000002655 kraft paper Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003140 primary amides Chemical group 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920001744 Polyaldehyde Polymers 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229920006321 anionic cellulose Polymers 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000006886 vinylation reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
- C08G69/50—Polymers modified by chemical after-treatment with aldehydes
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyamides (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/657,673 US4079043A (en) | 1974-11-04 | 1976-02-12 | Glyoxal modified poly(beta-alanine) strengthening resins for use in paper |
| US657673 | 1976-02-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5298794A JPS5298794A (en) | 1977-08-18 |
| JPS6024129B2 true JPS6024129B2 (ja) | 1985-06-11 |
Family
ID=24638177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52013096A Expired JPS6024129B2 (ja) | 1976-02-12 | 1977-02-10 | グリオキサ−ル変性ポリ（β−アラニン）の製造方法 |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS6024129B2 (enExample) |
| AT (1) | AT356899B (enExample) |
| AU (1) | AU511470B2 (enExample) |
| BE (1) | BE851011A (enExample) |
| BR (1) | BR7700825A (enExample) |
| CA (1) | CA1096540A (enExample) |
| CH (1) | CH618993A5 (enExample) |
| DE (1) | DE2705873A1 (enExample) |
| DK (1) | DK61377A (enExample) |
| ES (1) | ES455850A1 (enExample) |
| FI (1) | FI63431C (enExample) |
| FR (1) | FR2352019A1 (enExample) |
| GB (1) | GB1575951A (enExample) |
| IT (1) | IT1075563B (enExample) |
| NL (1) | NL172748C (enExample) |
| NO (1) | NO146866C (enExample) |
| SE (1) | SE432940B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60160027U (ja) * | 1984-03-30 | 1985-10-24 | 朝日金属精工株式会社 | 振動防止型ジヤンパ装置 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6017113A (ja) * | 1983-07-07 | 1985-01-29 | Teijin Ltd | 芳香族ポリアミド繊維の製造法 |
| FR2624866B1 (fr) * | 1987-12-16 | 1991-11-29 | Oreal | Procede de preparation de poly i2b-alanine reticulee sous forme de microspheres |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3329657A (en) * | 1963-05-17 | 1967-07-04 | American Cyanamid Co | Water soluble cross linked cationic polyamide polyamines |
| US3320215A (en) * | 1963-10-24 | 1967-05-16 | Scott Paper Co | Water-soluble nylon-type resins |
| US3607622A (en) * | 1968-07-24 | 1971-09-21 | Hercules Inc | Aminopolyamide-acrylamide-polyaldehyde resins having utility as wet and dry strength agents, retention aids and flocculants and a process of making and using them and paper made therefrom |
| US3728215A (en) * | 1971-03-12 | 1973-04-17 | Hercules Inc | Aminopalyamide{13 acrylamide{13 polyaldehyde resins employing an alpha, beta-unsaturated monobasic carboxylic acid or ester to make the aminopolyamide and their utility as wet and dry strengthening agents in papermaking |
-
1977
- 1977-01-11 CA CA269,445A patent/CA1096540A/en not_active Expired
- 1977-01-28 NO NO770295A patent/NO146866C/no unknown
- 1977-01-28 FI FI770300A patent/FI63431C/fi not_active IP Right Cessation
- 1977-02-01 FR FR7702745A patent/FR2352019A1/fr active Granted
- 1977-02-02 BE BE174596A patent/BE851011A/xx not_active IP Right Cessation
- 1977-02-08 NL NLAANVRAGE7701281,A patent/NL172748C/xx not_active IP Right Cessation
- 1977-02-10 BR BR7700825A patent/BR7700825A/pt unknown
- 1977-02-10 SE SE7701515A patent/SE432940B/xx not_active IP Right Cessation
- 1977-02-10 JP JP52013096A patent/JPS6024129B2/ja not_active Expired
- 1977-02-11 ES ES455850A patent/ES455850A1/es not_active Expired
- 1977-02-11 DE DE19772705873 patent/DE2705873A1/de not_active Withdrawn
- 1977-02-11 DK DK61377A patent/DK61377A/da not_active Application Discontinuation
- 1977-02-11 AT AT94077A patent/AT356899B/de not_active IP Right Cessation
- 1977-02-11 AU AU22203/77A patent/AU511470B2/en not_active Expired
- 1977-02-11 CH CH170277A patent/CH618993A5/fr not_active IP Right Cessation
- 1977-02-11 GB GB5715/77A patent/GB1575951A/en not_active Expired
- 1977-02-11 IT IT20211/77A patent/IT1075563B/it active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60160027U (ja) * | 1984-03-30 | 1985-10-24 | 朝日金属精工株式会社 | 振動防止型ジヤンパ装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL172748C (nl) | 1983-10-17 |
| IT1075563B (it) | 1985-04-22 |
| NO146866B (no) | 1982-09-13 |
| NO146866C (no) | 1982-12-22 |
| ATA94077A (de) | 1979-10-15 |
| AT356899B (de) | 1980-05-27 |
| NL7701281A (nl) | 1977-08-16 |
| DE2705873A1 (de) | 1977-08-18 |
| JPS5298794A (en) | 1977-08-18 |
| FI770300A7 (enExample) | 1977-08-13 |
| NO770295L (no) | 1977-08-15 |
| FI63431C (fi) | 1983-06-10 |
| CH618993A5 (en) | 1980-08-29 |
| FR2352019A1 (fr) | 1977-12-16 |
| ES455850A1 (es) | 1978-01-16 |
| FR2352019B1 (enExample) | 1984-12-07 |
| FI63431B (fi) | 1983-02-28 |
| CA1096540A (en) | 1981-02-24 |
| AU2220377A (en) | 1978-08-17 |
| SE432940B (sv) | 1984-04-30 |
| AU511470B2 (en) | 1980-08-21 |
| BE851011A (fr) | 1977-05-31 |
| BR7700825A (pt) | 1977-10-18 |
| GB1575951A (en) | 1980-10-01 |
| SE7701515L (sv) | 1977-08-13 |
| DK61377A (da) | 1977-08-13 |
| NL172748B (nl) | 1983-05-16 |
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