DE2255731C2 - 1,3,5-Tris-(4-tert.-butyl-3-hydroxy-2,6-dimethylbenzyl)-s-triazin-2,4,6-(1H,3H,5H)-trion und seine Verwendung als Oxidationshemmer - Google Patents
1,3,5-Tris-(4-tert.-butyl-3-hydroxy-2,6-dimethylbenzyl)-s-triazin-2,4,6-(1H,3H,5H)-trion und seine Verwendung als OxidationshemmerInfo
- Publication number
- DE2255731C2 DE2255731C2 DE2255731A DE2255731A DE2255731C2 DE 2255731 C2 DE2255731 C2 DE 2255731C2 DE 2255731 A DE2255731 A DE 2255731A DE 2255731 A DE2255731 A DE 2255731A DE 2255731 C2 DE2255731 C2 DE 2255731C2
- Authority
- DE
- Germany
- Prior art keywords
- tert
- compound
- antioxidants
- triazine
- butyl
- 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
- 239000003963 antioxidant agent Substances 0.000 title claims description 15
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 28
- 230000003078 antioxidant effect Effects 0.000 claims description 15
- -1 thiodipropionic acid ester Chemical class 0.000 claims description 13
- 239000003490 Thiodipropionic acid Substances 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 235000019303 thiodipropionic acid Nutrition 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000004743 Polypropylene Substances 0.000 description 11
- 229920001155 polypropylene Polymers 0.000 description 11
- 238000012545 processing Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 5
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 4
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000010525 oxidative degradation reaction Methods 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
- RKBBHKDUTIUASU-UHFFFAOYSA-N 3-(1-chloro-2,2-dimethylpropyl)-2,4-dimethylphenol Chemical compound C(C)(C)(C)C(C1=C(C(=CC=C1C)O)C)Cl RKBBHKDUTIUASU-UHFFFAOYSA-N 0.000 description 1
- WODZSHMAILHEGD-UHFFFAOYSA-N 6-tert-butyl-3-(chloromethyl)-2,4-dimethylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CCl WODZSHMAILHEGD-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19934071A | 1971-11-16 | 1971-11-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2255731A1 DE2255731A1 (de) | 1973-05-24 |
| DE2255731C2 true DE2255731C2 (de) | 1982-04-01 |
Family
ID=22737129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2255731A Expired DE2255731C2 (de) | 1971-11-16 | 1972-11-14 | 1,3,5-Tris-(4-tert.-butyl-3-hydroxy-2,6-dimethylbenzyl)-s-triazin-2,4,6-(1H,3H,5H)-trion und seine Verwendung als Oxidationshemmer |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3723427A (OSRAM) |
| JP (2) | JPS5644070B2 (OSRAM) |
| AR (1) | AR193135A1 (OSRAM) |
| AU (1) | AU468813B2 (OSRAM) |
| BE (1) | BE791369A (OSRAM) |
| BR (1) | BR7207663D0 (OSRAM) |
| CA (1) | CA981266A (OSRAM) |
| CH (1) | CH574431A5 (OSRAM) |
| DE (1) | DE2255731C2 (OSRAM) |
| FR (1) | FR2162923A5 (OSRAM) |
| GB (1) | GB1368371A (OSRAM) |
| HK (1) | HK27978A (OSRAM) |
| IT (1) | IT966377B (OSRAM) |
| NL (1) | NL179379C (OSRAM) |
| ZA (1) | ZA726175B (OSRAM) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7388029B2 (en) | 2000-03-31 | 2008-06-17 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| USRE43372E1 (en) | 1999-03-05 | 2012-05-08 | Duke University | C16 unsaturated FP-selective prostaglandins analogs |
| US8618086B2 (en) | 2000-03-31 | 2013-12-31 | Duke University | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| US8623918B2 (en) | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US8722739B2 (en) | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US9346837B2 (en) | 2000-03-31 | 2016-05-24 | Duke University | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4049654A (en) * | 1973-09-25 | 1977-09-20 | Ciba-Geigy Corporation | 2,3,5-Trialkylsubstituted hydroxybenzyl isocyanurates |
| US3966675A (en) * | 1974-11-11 | 1976-06-29 | American Cyanamid Company | Thermal stabilizers for polypropylene |
| JPS56152863A (en) * | 1980-04-28 | 1981-11-26 | Adeka Argus Chem Co Ltd | Synthetic resin composition |
| JPS573842A (en) * | 1980-06-10 | 1982-01-09 | Sumitomo Chem Co Ltd | Stabilized polyolefin composition |
| US4826983A (en) * | 1985-11-21 | 1989-05-02 | Ici Americas Inc. | N-2,2-dimethyl-2-(2-hydroxy-alkylphenyl) heterocycles and stabilized compositions |
| JPS6371751U (OSRAM) * | 1986-10-27 | 1988-05-13 | ||
| US5229445A (en) * | 1988-02-10 | 1993-07-20 | Shell Oil Company | Stabilized olefin/carbon monoxide copolymers |
| US4925938A (en) * | 1988-12-20 | 1990-05-15 | Ici Americas Inc. | N-2,2-dimethyl-2-(2-hydroxy-alkylphenyl) heterocycles and stabilized compositions |
| DE69927372T2 (de) | 1998-06-22 | 2006-07-13 | Cytec Technology Corp., Wilmington | In den roten Bereich verschobene Trisaryl-1,3,5-Triazin-Ultraviolettlicht-Absorptionsmittel |
| US20020146439A1 (en) * | 2000-03-31 | 2002-10-10 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using oximyl and hydroxylamino prostaglandins |
| KR100646654B1 (ko) * | 2005-03-09 | 2006-11-23 | 주식회사 코오롱 | 굴곡특성이 우수한 열가소성 폴리에테르에스테르 엘라스토머 수지조성물 및 이로부터 제조된 차량용 에어백 장치용커버 |
| KR101379619B1 (ko) | 2011-01-20 | 2014-04-01 | 코오롱플라스틱 주식회사 | 열가소성 폴리에테르에스테르 엘라스토머 수지 조성물 및 이로부터 제조된 탄성 모노 필라멘트 |
| CN103420932B (zh) * | 2013-08-26 | 2016-02-17 | 天津利安隆新材料股份有限公司 | 1，3，5-三（4-叔丁基-3-羟基-2，6-二甲基苄基）异氰尿酸酯的制备方法 |
| CN103483283A (zh) * | 2013-09-13 | 2014-01-01 | 天津利安隆新材料股份有限公司 | 一种抗氧化剂1790的合成方法 |
| CN104557752B (zh) * | 2013-10-09 | 2017-07-25 | 华东师范大学 | 1,3,5‑三(4‑叔丁基‑3‑羟基‑2,6‑二甲基苄基)‑1,3,5‑三嗪‑2,4,6(1h,3h,5h)‑三酮化合物的合成方法 |
| GB201604235D0 (en) | 2016-03-11 | 2016-04-27 | Ucl Business Plc | Lipids and complexes for the delivery of biologically-active material to cells |
| KR102572631B1 (ko) * | 2016-10-07 | 2023-08-31 | 주식회사 에이치엘클레무브 | 차량의 충돌 완충 장치 및 방법 |
| CN109912524A (zh) * | 2019-04-05 | 2019-06-21 | 南通大学 | 一种受阻酚类抗氧化剂的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3531483A (en) * | 1968-10-25 | 1970-09-29 | Goodrich Co B F | Hydroxyphenylalkyleneyl isocyanurates |
-
0
- BE BE791369D patent/BE791369A/xx not_active IP Right Cessation
-
1971
- 1971-11-16 US US00199340A patent/US3723427A/en not_active Expired - Lifetime
-
1972
- 1972-09-11 ZA ZA726175A patent/ZA726175B/xx unknown
- 1972-09-14 AU AU46682/72A patent/AU468813B2/en not_active Expired
- 1972-09-14 GB GB4271872A patent/GB1368371A/en not_active Expired
- 1972-09-14 CA CA151,746A patent/CA981266A/en not_active Expired
- 1972-10-04 NL NLAANVRAGE7213427,A patent/NL179379C/xx not_active IP Right Cessation
- 1972-10-17 IT IT53424/72A patent/IT966377B/it active
- 1972-10-19 AR AR244701A patent/AR193135A1/es active
- 1972-10-31 BR BR007663/72A patent/BR7207663D0/pt unknown
- 1972-11-14 DE DE2255731A patent/DE2255731C2/de not_active Expired
- 1972-11-14 FR FR7240400A patent/FR2162923A5/fr not_active Expired
- 1972-11-16 JP JP11432272A patent/JPS5644070B2/ja not_active Expired
- 1972-11-16 CH CH1667872A patent/CH574431A5/xx not_active IP Right Cessation
-
1978
- 1978-06-01 HK HK279/78A patent/HK27978A/xx unknown
-
1981
- 1981-02-07 JP JP56017366A patent/JPS5910753B2/ja not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE43372E1 (en) | 1999-03-05 | 2012-05-08 | Duke University | C16 unsaturated FP-selective prostaglandins analogs |
| US7388029B2 (en) | 2000-03-31 | 2008-06-17 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US8541466B2 (en) | 2000-03-31 | 2013-09-24 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US8618086B2 (en) | 2000-03-31 | 2013-12-31 | Duke University | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| US8906962B2 (en) | 2000-03-31 | 2014-12-09 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US9346837B2 (en) | 2000-03-31 | 2016-05-24 | Duke University | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
| US9579270B2 (en) | 2000-03-31 | 2017-02-28 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US8623918B2 (en) | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US8722739B2 (en) | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
Also Published As
| Publication number | Publication date |
|---|---|
| US3723427A (en) | 1973-03-27 |
| JPS5644070B2 (OSRAM) | 1981-10-16 |
| DE2255731A1 (de) | 1973-05-24 |
| CH574431A5 (OSRAM) | 1976-04-15 |
| CA981266A (en) | 1976-01-06 |
| IT966377B (it) | 1974-02-11 |
| NL7213427A (OSRAM) | 1973-05-18 |
| AR193135A1 (es) | 1973-03-30 |
| GB1368371A (en) | 1974-09-25 |
| JPS5910753B2 (ja) | 1984-03-10 |
| FR2162923A5 (OSRAM) | 1973-07-20 |
| JPS4861487A (OSRAM) | 1973-08-28 |
| NL179379C (nl) | 1986-09-01 |
| AU468813B2 (en) | 1976-01-22 |
| ZA726175B (en) | 1973-06-27 |
| AU4668272A (en) | 1974-03-21 |
| JPS56167785A (en) | 1981-12-23 |
| BE791369A (fr) | 1973-05-14 |
| BR7207663D0 (pt) | 1973-08-23 |
| HK27978A (en) | 1978-06-09 |
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