FR2487369A1 - Composition acrylique elastomere contenant un terpolymere d'une diolefine conjuguee, d'un nitrile insature et d'un ester carboxylique insature - Google Patents
Composition acrylique elastomere contenant un terpolymere d'une diolefine conjuguee, d'un nitrile insature et d'un ester carboxylique insature Download PDFInfo
- Publication number
- FR2487369A1 FR2487369A1 FR8114162A FR8114162A FR2487369A1 FR 2487369 A1 FR2487369 A1 FR 2487369A1 FR 8114162 A FR8114162 A FR 8114162A FR 8114162 A FR8114162 A FR 8114162A FR 2487369 A1 FR2487369 A1 FR 2487369A1
- Authority
- FR
- France
- Prior art keywords
- sep
- weight
- acrylate
- composition according
- alpha
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 58
- 229920001897 terpolymer Polymers 0.000 title claims abstract description 30
- 150000002825 nitriles Chemical class 0.000 title claims abstract description 21
- 150000001993 dienes Chemical class 0.000 title claims abstract description 15
- 150000001733 carboxylic acid esters Chemical class 0.000 title claims description 8
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 29
- 229920000800 acrylic rubber Polymers 0.000 claims abstract description 25
- 229920001577 copolymer Polymers 0.000 claims abstract description 24
- 229920001971 elastomer Polymers 0.000 claims abstract description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 18
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 14
- -1 beta-unsaturated carboxyl ester Chemical class 0.000 claims description 13
- 238000004073 vulcanization Methods 0.000 claims description 9
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 claims description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 8
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 8
- 239000000806 elastomer Substances 0.000 claims description 8
- 229920000459 Nitrile rubber Polymers 0.000 claims description 7
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims description 5
- KLAWFKRMCIXRFS-UHFFFAOYSA-N 5-ethenylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C=C)CC1C=C2 KLAWFKRMCIXRFS-UHFFFAOYSA-N 0.000 claims description 4
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 4
- COXYCFKHVQFUPA-UHFFFAOYSA-N but-2-enyl prop-2-enoate Chemical compound CC=CCOC(=O)C=C COXYCFKHVQFUPA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- OXUKGAGPJSQCDS-UHFFFAOYSA-N 3-methylbut-2-enyl prop-2-enoate Chemical compound CC(C)=CCOC(=O)C=C OXUKGAGPJSQCDS-UHFFFAOYSA-N 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004902 Softening Agent Substances 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims 1
- 229920001651 Cyanoacrylate Polymers 0.000 claims 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract description 17
- 238000007906 compression Methods 0.000 abstract description 11
- 230000006835 compression Effects 0.000 abstract description 11
- 239000005060 rubber Substances 0.000 abstract description 4
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 abstract 2
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 238000011109 contamination Methods 0.000 description 7
- 238000007720 emulsion polymerization reaction Methods 0.000 description 6
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- AJJCQYIECZAJBB-UHFFFAOYSA-N 2-ethylsulfanylethyl prop-2-enoate Chemical compound CCSCCOC(=O)C=C AJJCQYIECZAJBB-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- KAGWLGUCGNNPFW-UHFFFAOYSA-N 2-methylsulfanylethyl prop-2-enoate Chemical compound CSCCOC(=O)C=C KAGWLGUCGNNPFW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical compound C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 description 1
- 238000010059 sulfur vulcanization Methods 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/02—Copolymers with acrylonitrile
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/18—Homopolymers or copolymers of nitriles
- C08L33/20—Homopolymers or copolymers of acrylonitrile
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F04—POSITIVE - DISPLACEMENT MACHINES FOR LIQUIDS; PUMPS FOR LIQUIDS OR ELASTIC FLUIDS
- F04C—ROTARY-PISTON, OR OSCILLATING-PISTON, POSITIVE-DISPLACEMENT MACHINES FOR LIQUIDS; ROTARY-PISTON, OR OSCILLATING-PISTON, POSITIVE-DISPLACEMENT PUMPS
- F04C2210/00—Fluid
- F04C2210/26—Refrigerants with particular properties, e.g. HFC-134a
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9941980A JPS5725342A (en) | 1980-07-22 | 1980-07-22 | Rubber composition |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2487369A1 true FR2487369A1 (fr) | 1982-01-29 |
FR2487369B1 FR2487369B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-02-10 |
Family
ID=14246944
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR8114162A Granted FR2487369A1 (fr) | 1980-07-22 | 1981-07-21 | Composition acrylique elastomere contenant un terpolymere d'une diolefine conjuguee, d'un nitrile insature et d'un ester carboxylique insature |
Country Status (5)
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2532245A1 (fr) * | 1982-08-27 | 1984-03-02 | Nippon Zeon Co | Courroie constituee d'un caoutchouc polymere et renforcee par des fibres |
EP0424348A1 (en) * | 1989-10-16 | 1991-04-24 | Monsanto Company | Elastomeric blends |
EP0424347A1 (en) * | 1989-10-16 | 1991-04-24 | Monsanto Company | Elastomer compositions |
EP1462482A4 (en) * | 2001-11-30 | 2005-01-12 | Zeon Corp | RUBBER VULCANISATE, MANUFACTURING METHOD, POLYMER COMPOSITION, RUBBER COMPOSITION, AND VULCANIZABLE RUBBER COMPOSITION USED IN THIS PROCESS |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58167604A (ja) * | 1982-03-27 | 1983-10-03 | Nippon Zeon Co Ltd | 耐油劣化性ゴム部材 |
JPH0736538Y2 (ja) * | 1990-11-30 | 1995-08-23 | 多喜子 君島 | コップ保持具 |
JPH06327549A (ja) * | 1993-05-20 | 1994-11-29 | J Seven:Kk | ジョッキ型保冷保温シート |
JP2003026861A (ja) * | 2001-07-13 | 2003-01-29 | Jsr Corp | 耐油耐候性ゴム用組成物及び耐油耐候性ゴム |
US7550536B2 (en) | 2001-12-25 | 2009-06-23 | Jsr Corporation | Acrylic rubber, process for its production, and rubber compositions, oil-and weather-resistant rubber compositions, and oil-and weather -resistant rubbers, containing the same |
US8080486B1 (en) | 2010-07-28 | 2011-12-20 | Honeywell International Inc. | Ballistic shield composites with enhanced fragment resistance |
WO2024005060A1 (ja) * | 2022-07-01 | 2024-01-04 | 日本ゼオン株式会社 | ジエン系重合体ゴム |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5420091A (en) * | 1977-07-18 | 1979-02-15 | Japan Synthetic Rubber Co Ltd | Preparation of heat-resistant, flexing-resistant rubber |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3790646A (en) * | 1971-05-01 | 1974-02-05 | H Fukuda | Oil-resistant polymer composition |
DE2249322A1 (de) * | 1972-10-07 | 1974-04-11 | Bosch Gmbh Robert | Elektronisch gesteuerte zuendanlage |
-
1980
- 1980-07-22 JP JP9941980A patent/JPS5725342A/ja active Granted
-
1981
- 1981-07-21 FR FR8114162A patent/FR2487369A1/fr active Granted
- 1981-07-21 CA CA000382103A patent/CA1190343A/en not_active Expired
- 1981-07-21 IT IT48937/81A patent/IT1171404B/it active
- 1981-07-22 DE DE3128993A patent/DE3128993C2/de not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5420091A (en) * | 1977-07-18 | 1979-02-15 | Japan Synthetic Rubber Co Ltd | Preparation of heat-resistant, flexing-resistant rubber |
Non-Patent Citations (2)
Title |
---|
CHEMICAL ABSTRACTS, vol. 80, no. 24, 17 juin 1974, réf. no. 134508g, page 53, Columbus Ohio (US) * |
PATENTS ABSTRACTS OF JAPAN, vol. 3, no. 46, 18 avril 1979, page 37 C-43 & JP - A - 54 20 091 (NIPPON GOSEI GOMU K.K.) (15.02.1979) * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2532245A1 (fr) * | 1982-08-27 | 1984-03-02 | Nippon Zeon Co | Courroie constituee d'un caoutchouc polymere et renforcee par des fibres |
EP0424348A1 (en) * | 1989-10-16 | 1991-04-24 | Monsanto Company | Elastomeric blends |
EP0424347A1 (en) * | 1989-10-16 | 1991-04-24 | Monsanto Company | Elastomer compositions |
US5051480A (en) * | 1989-10-16 | 1991-09-24 | Monsanto Company | Elastomeric blends |
US5053450A (en) * | 1989-10-16 | 1991-10-01 | Monsanto Company | Elastomer compositions |
EP1462482A4 (en) * | 2001-11-30 | 2005-01-12 | Zeon Corp | RUBBER VULCANISATE, MANUFACTURING METHOD, POLYMER COMPOSITION, RUBBER COMPOSITION, AND VULCANIZABLE RUBBER COMPOSITION USED IN THIS PROCESS |
Also Published As
Publication number | Publication date |
---|---|
JPS5725342A (en) | 1982-02-10 |
JPS6123935B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-06-09 |
FR2487369B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-02-10 |
IT1171404B (it) | 1987-06-10 |
CA1190343A (en) | 1985-07-09 |
IT8148937A0 (it) | 1981-07-21 |
DE3128993C2 (de) | 1984-04-05 |
DE3128993A1 (de) | 1982-04-08 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |