DE3637467A1 - Bicyclische acrylmonomere - Google Patents
Bicyclische acrylmonomereInfo
- Publication number
- DE3637467A1 DE3637467A1 DE19863637467 DE3637467A DE3637467A1 DE 3637467 A1 DE3637467 A1 DE 3637467A1 DE 19863637467 DE19863637467 DE 19863637467 DE 3637467 A DE3637467 A DE 3637467A DE 3637467 A1 DE3637467 A1 DE 3637467A1
- Authority
- DE
- Germany
- Prior art keywords
- bicyclic
- polymerization
- monomers
- alkylene
- ethyl
- 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.)
- Withdrawn
Links
- 239000000178 monomer Substances 0.000 title claims description 32
- 229920000642 polymer Polymers 0.000 claims description 16
- -1 Bicyclic aryl compound Chemical class 0.000 claims description 15
- 238000010526 radical polymerization reaction Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000012656 cationic ring opening polymerization Methods 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001924 cycloalkanes Chemical class 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 125000002619 bicyclic group Chemical group 0.000 description 11
- 239000000126 substance Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 238000010538 cationic polymerization reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 150000002905 orthoesters Chemical class 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- IQJVBAIESAQUKR-UHFFFAOYSA-N isocyanic acid;prop-2-enoic acid Chemical compound N=C=O.OC(=O)C=C IQJVBAIESAQUKR-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DMQYPVOQAARSNF-UHFFFAOYSA-N 3-[2,3-bis(3-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OCCCOCC(OCCCOC(=O)C=C)COCCCOC(=O)C=C DMQYPVOQAARSNF-UHFFFAOYSA-N 0.000 description 1
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 102000003745 Hepatocyte Growth Factor Human genes 0.000 description 1
- 108090000100 Hepatocyte Growth Factor Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000005520 diaryliodonium group Chemical group 0.000 description 1
- CHNPVIBKPFVVQK-UHFFFAOYSA-L dibutyltin(2+);2-octyl-2-sulfanyldecanoate Chemical compound CCCC[Sn+2]CCCC.CCCCCCCCC(S)(C([O-])=O)CCCCCCCC.CCCCCCCCC(S)(C([O-])=O)CCCCCCCC CHNPVIBKPFVVQK-UHFFFAOYSA-L 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000011038 discontinuous diafiltration by volume reduction Methods 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- IIQWTZQWBGDRQG-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C(C)=C IIQWTZQWBGDRQG-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79552385A | 1985-11-06 | 1985-11-06 | |
| US06/912,538 US4672098A (en) | 1985-11-06 | 1986-10-01 | Bicyclic acrylic monomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3637467A1 true DE3637467A1 (de) | 1987-05-07 |
Family
ID=27121624
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863637467 Withdrawn DE3637467A1 (de) | 1985-11-06 | 1986-11-04 | Bicyclische acrylmonomere |
| DE3644981A Expired - Lifetime DE3644981C2 (enExample) | 1985-11-06 | 1986-11-04 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3644981A Expired - Lifetime DE3644981C2 (enExample) | 1985-11-06 | 1986-11-04 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4672098A (enExample) |
| AU (1) | AU586046B2 (enExample) |
| BE (1) | BE905691A (enExample) |
| CA (1) | CA1256445A (enExample) |
| DE (2) | DE3637467A1 (enExample) |
| FR (1) | FR2589471B1 (enExample) |
| GB (1) | GB2182661B (enExample) |
| LU (1) | LU86646A1 (enExample) |
| NL (1) | NL185922C (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5360836A (en) * | 1986-10-02 | 1994-11-01 | Societe Nationale Des Poudres Et Explosifs | Process for the production of coatings by radiation cross-linking |
| US4859780A (en) * | 1988-02-26 | 1989-08-22 | Ciba-Geigy Corporation | Hydrophilic modifier monomers |
| KR960015375B1 (ko) * | 1994-06-08 | 1996-11-11 | 현대전자산업 주식회사 | 강유전체 박막 제조장치 및 그를 사용한 강유전체 박막 제조방법 |
| CA2300997A1 (en) * | 1997-08-22 | 1999-03-04 | Akzo Nobel Nv | Coating composition comprising a compound comprising at least one bicyclo-orthoester group and at least one other functional group |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4425473A (en) * | 1980-02-04 | 1984-01-10 | Toagosei Chemical Industry Co., Ltd. | Polymerizable bicyclic orthoester compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686224A (en) * | 1970-02-24 | 1972-08-22 | Gulf Research Development Co | 2,6,7-trioxabicyclo(2.2.2)octane compounds |
| US4405798A (en) * | 1981-03-30 | 1983-09-20 | Celanese Corporation | Acrylate and methacrylate monoesters of pentaerythritol and pentaerythritol orthoesters and polymers and copolymers derived therefrom |
| US4526949A (en) * | 1981-03-30 | 1985-07-02 | Celanese Corporation | Acrylate and methacrylate monoesters of pentaerythritol and pentaerythritol orthoesters and polymers and copolymers derived therefrom |
| JPS60233114A (ja) * | 1984-05-07 | 1985-11-19 | Mitsui Toatsu Chem Inc | 架橋性重合体 |
| JPS60233108A (ja) * | 1984-05-07 | 1985-11-19 | Mitsui Toatsu Chem Inc | 樹脂形成用組成物 |
| IL79532A0 (en) * | 1985-07-30 | 1986-10-31 | Wellcome Found | Substituted trioxabicyclooctanes,their preparation and their use as pesticides |
| JPH117538A (ja) * | 1997-06-17 | 1999-01-12 | Minolta Co Ltd | 画像処理装置及び記憶媒体 |
-
1986
- 1986-10-01 US US06/912,538 patent/US4672098A/en not_active Expired - Fee Related
- 1986-10-17 CA CA000520782A patent/CA1256445A/en not_active Expired
- 1986-10-29 NL NLAANVRAGE8602723,A patent/NL185922C/xx not_active IP Right Cessation
- 1986-11-03 AU AU64651/86A patent/AU586046B2/en not_active Ceased
- 1986-11-04 DE DE19863637467 patent/DE3637467A1/de not_active Withdrawn
- 1986-11-04 FR FR868615359A patent/FR2589471B1/fr not_active Expired - Lifetime
- 1986-11-04 DE DE3644981A patent/DE3644981C2/de not_active Expired - Lifetime
- 1986-11-04 BE BE0/217359A patent/BE905691A/fr not_active IP Right Cessation
- 1986-11-05 LU LU86646A patent/LU86646A1/de unknown
- 1986-11-06 GB GB8626579A patent/GB2182661B/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4425473A (en) * | 1980-02-04 | 1984-01-10 | Toagosei Chemical Industry Co., Ltd. | Polymerizable bicyclic orthoester compounds |
Non-Patent Citations (3)
| Title |
|---|
| JP 60-233108 ref. in CA 104:187067h und Patent Abstracts of Japan C 340, 18.04.86, Nr.103 * |
| POLYMER J.: 13/7 (1981), S. 715-718 * |
| POLYMER J.: 14/11 (1982), S. 927-930 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6465186A (en) | 1987-05-14 |
| GB2182661A (en) | 1987-05-20 |
| NL185922B (nl) | 1990-03-16 |
| NL8602723A (nl) | 1987-06-01 |
| NL185922C (nl) | 1990-08-16 |
| DE3644981C2 (enExample) | 1990-04-19 |
| CA1256445A (en) | 1989-06-27 |
| LU86646A1 (fr) | 1987-05-04 |
| BE905691A (fr) | 1987-05-04 |
| AU586046B2 (en) | 1989-06-29 |
| GB8626579D0 (en) | 1986-12-10 |
| FR2589471B1 (fr) | 1990-03-02 |
| GB2182661B (en) | 1989-11-22 |
| FR2589471A1 (fr) | 1987-05-07 |
| US4672098A (en) | 1987-06-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8172 | Supplementary division/partition in: |
Ref country code: DE Ref document number: 3644981 Format of ref document f/p: P |
|
| Q171 | Divided out to: |
Ref country code: DE Ref document number: 3644981 |
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