DE2942786C2 - - Google Patents
Info
- Publication number
- DE2942786C2 DE2942786C2 DE2942786A DE2942786A DE2942786C2 DE 2942786 C2 DE2942786 C2 DE 2942786C2 DE 2942786 A DE2942786 A DE 2942786A DE 2942786 A DE2942786 A DE 2942786A DE 2942786 C2 DE2942786 C2 DE 2942786C2
- Authority
- DE
- Germany
- Prior art keywords
- siloxane
- polydiorganosiloxane
- carbon atoms
- parts
- preparation
- 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
- 238000002360 preparation method Methods 0.000 claims description 29
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 22
- 239000000839 emulsion Substances 0.000 claims description 14
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 10
- 229910000077 silane Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000005375 organosiloxane group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000004753 textile Substances 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- -1 2,4,4-trimethylpentyl Chemical group 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- 210000002268 wool Anatomy 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000000835 fiber Substances 0.000 description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 6
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IHEDBVUTTQXGSJ-UHFFFAOYSA-M 2-[bis(2-oxidoethyl)amino]ethanolate;titanium(4+);hydroxide Chemical compound [OH-].[Ti+4].[O-]CCN(CC[O-])CC[O-] IHEDBVUTTQXGSJ-UHFFFAOYSA-M 0.000 description 2
- MWRSABPHNREIIX-UHFFFAOYSA-N 9,9-dimethyldecan-1-ol Chemical compound CC(C)(C)CCCCCCCCO MWRSABPHNREIIX-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- 102000011782 Keratins Human genes 0.000 description 2
- 108010076876 Keratins Proteins 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012875 nonionic emulsifier Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 description 1
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- ZNZBASDDVBURLC-UHFFFAOYSA-N dibutyl(diethoxy)stannane Chemical compound CCCC[Sn](OCC)(OCC)CCCC ZNZBASDDVBURLC-UHFFFAOYSA-N 0.000 description 1
- MACVNMKPAKPZQG-UHFFFAOYSA-N dioctyltin(2+);methanolate Chemical compound CCCCCCCC[Sn](OC)(OC)CCCCCCCC MACVNMKPAKPZQG-UHFFFAOYSA-N 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 229960005082 etohexadiol Drugs 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001843 polymethylhydrosiloxane Chemical group 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- 230000037303 wrinkles Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7843757 | 1978-11-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2942786A1 DE2942786A1 (de) | 1980-05-22 |
| DE2942786C2 true DE2942786C2 (enrdf_load_stackoverflow) | 1989-06-29 |
Family
ID=10500896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792942786 Granted DE2942786A1 (de) | 1978-11-08 | 1979-10-23 | Verfahren zur herstellung eines polydiorganosiloxans |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS586731B2 (enrdf_load_stackoverflow) |
| AU (1) | AU528039B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1134986A (enrdf_load_stackoverflow) |
| DE (1) | DE2942786A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2440961A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2036052B (enrdf_load_stackoverflow) |
| IT (1) | IT1165361B (enrdf_load_stackoverflow) |
| ZA (1) | ZA795749B (enrdf_load_stackoverflow) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57111354A (en) * | 1980-12-29 | 1982-07-10 | Toray Silicone Co Ltd | Organopolysiloxane composition |
| DE3104582A1 (de) * | 1981-02-10 | 1982-09-02 | Wacker-Chemie GmbH, 8000 München | "verfahren zur impraegnierung von textilen flaechengebilden" |
| GB2107725B (en) * | 1981-10-03 | 1985-02-27 | Dow Corning | Siloxane quaternary ammonium salt preparation |
| US4620878A (en) * | 1983-10-17 | 1986-11-04 | Dow Corning Corporation | Method of preparing polyorganosiloxane emulsions having small particle size |
| JPS60185880A (ja) * | 1984-02-29 | 1985-09-21 | 竹本油脂株式会社 | 炭素繊維製造用油剤 |
| GB8725921D0 (en) * | 1987-11-05 | 1987-12-09 | Precision Proc Textiles Ltd | Treatment of wool |
| GB8819569D0 (en) * | 1988-08-17 | 1988-09-21 | Dow Corning Ltd | Emulsions for treating fibrous materials |
| GB8828414D0 (en) * | 1988-12-06 | 1989-01-05 | Precision Proc Textiles Ltd | Method for treatment of cellulosic fibres |
| DE4007136A1 (de) * | 1989-08-05 | 1991-09-12 | Pfersee Chem Fab | Zusammensetzung in form einer waessrigen dispersion und verfahren zur behandlung von fasermaterialien |
| GB9311509D0 (en) * | 1993-06-03 | 1993-07-21 | Dow Corning | Process for the preparation of organopolysiloxanes |
| DE19506396A1 (de) * | 1995-02-23 | 1996-08-29 | Wacker Chemie Gmbh | Optisch klare Aminosiliconzusammensetzungen |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1294235A (fr) * | 1960-05-13 | 1962-05-26 | Dow Corning | Procédé de préparation de copolymères aminoalkylsiloxanes |
| US3418162A (en) * | 1963-12-07 | 1968-12-24 | Shinetsu Chem Ind Co | Composition of waterproof agent and process for manufacture of waterproof cloth using the same |
| US3355424A (en) * | 1964-07-29 | 1967-11-28 | Dow Corning | Method for the preparation of aminoalkylsiloxane copolymers |
| GB1434017A (en) * | 1972-07-15 | 1976-04-28 | Dow Corning Ltd | Treatment of fibres |
| JPS5137996B2 (enrdf_load_stackoverflow) * | 1973-04-26 | 1976-10-19 | ||
| GB1543157A (en) * | 1975-05-17 | 1979-03-28 | Dow Corning Ltd | Treatment of fibres |
| DE2615078C2 (de) * | 1976-04-07 | 1983-01-27 | Wacker-Chemie GmbH, 8000 München | Verfahren zur Behandlung von organischen Fasern und dabei verwendete Organopolysiloxanzusammensetzungen |
| GB1572397A (en) * | 1976-06-11 | 1980-07-30 | Dow Corning Ltd | Fibre treatment composition and process |
| GB1565241A (en) * | 1976-07-21 | 1980-04-16 | Goldschmidt Ag Th | Process for rendering wool shrink-resistant |
-
1979
- 1979-10-12 CA CA000337498A patent/CA1134986A/en not_active Expired
- 1979-10-23 DE DE19792942786 patent/DE2942786A1/de active Granted
- 1979-10-26 ZA ZA00795749A patent/ZA795749B/xx unknown
- 1979-10-29 GB GB7937383A patent/GB2036052B/en not_active Expired
- 1979-10-31 FR FR7927017A patent/FR2440961A1/fr active Granted
- 1979-11-05 AU AU52527/79A patent/AU528039B2/en not_active Ceased
- 1979-11-07 IT IT27102/79A patent/IT1165361B/it active
- 1979-11-07 JP JP54144294A patent/JPS586731B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2440961A1 (fr) | 1980-06-06 |
| CA1134986A (en) | 1982-11-02 |
| GB2036052A (en) | 1980-06-25 |
| JPS586731B2 (ja) | 1983-02-05 |
| AU528039B2 (en) | 1983-04-14 |
| JPS5566928A (en) | 1980-05-20 |
| DE2942786A1 (de) | 1980-05-22 |
| IT7927102A0 (it) | 1979-11-07 |
| GB2036052B (en) | 1983-03-23 |
| IT1165361B (it) | 1987-04-22 |
| FR2440961B1 (enrdf_load_stackoverflow) | 1984-10-05 |
| AU5252779A (en) | 1980-05-15 |
| ZA795749B (en) | 1980-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |
|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C08L 83/05 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |