FI112247B - Framställning av en talloljehartsester med låg luktnivå - Google Patents
Framställning av en talloljehartsester med låg luktnivå Download PDFInfo
- Publication number
- FI112247B FI112247B FI971663A FI971663A FI112247B FI 112247 B FI112247 B FI 112247B FI 971663 A FI971663 A FI 971663A FI 971663 A FI971663 A FI 971663A FI 112247 B FI112247 B FI 112247B
- Authority
- FI
- Finland
- Prior art keywords
- resin
- tall oil
- approx
- product
- ester
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 42
- 239000003784 tall oil Substances 0.000 title claims abstract description 24
- 229920005989 resin Polymers 0.000 title claims description 74
- 239000011347 resin Substances 0.000 title claims description 74
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 33
- 238000001704 evaporation Methods 0.000 claims abstract description 20
- 230000008569 process Effects 0.000 claims abstract description 20
- 230000032050 esterification Effects 0.000 claims abstract description 19
- 238000005886 esterification reaction Methods 0.000 claims abstract description 19
- 230000008020 evaporation Effects 0.000 claims abstract description 16
- 229920005862 polyol Polymers 0.000 claims abstract description 11
- 150000003077 polyols Chemical class 0.000 claims abstract description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 11
- 230000007935 neutral effect Effects 0.000 claims description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 239000003990 capacitor Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract description 11
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 abstract description 10
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 abstract description 10
- 235000019645 odor Nutrition 0.000 description 27
- 239000000047 product Substances 0.000 description 23
- -1 C20 monocarboxylic acid acids Chemical class 0.000 description 21
- 229940059574 pentaerithrityl Drugs 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000012855 volatile organic compound Substances 0.000 description 4
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 3
- 235000011613 Pinus brutia Nutrition 0.000 description 3
- 241000018646 Pinus brutia Species 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004831 Hot glue Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004840 adhesive resin Substances 0.000 description 2
- 229920006223 adhesive resin Polymers 0.000 description 2
- SJEZDMHBMZPMME-UHFFFAOYSA-L calcium;(3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinate Chemical compound [Ca+2].CCOP([O-])(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CCOP([O-])(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SJEZDMHBMZPMME-UHFFFAOYSA-L 0.000 description 2
- 229940112822 chewing gum Drugs 0.000 description 2
- 235000015218 chewing gum Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002314 glycerols Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002898 organic sulfur compounds Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- DYHSBBDFFBVQSS-UHFFFAOYSA-J dicalcium;2,6-ditert-butyl-4-(1-phosphonatopropyl)phenol Chemical compound [Ca+2].[Ca+2].CCC(P([O-])([O-])=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CCC(P([O-])([O-])=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 DYHSBBDFFBVQSS-UHFFFAOYSA-J 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000005337 ground glass Substances 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 230000021317 sensory perception Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000002087 whitening effect Effects 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
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Organic Insulating Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Claims (8)
1. Förfarande för framställning av en talloljehartsester med lag luktnivä, vilket förfarande omfattar ett förestringssteg där ett talloljeharts förestras med en polyol för bildande av en produkt innehällande en talloljehartsester, kännetecknat av att 5 den frän förestringen erhällna produkten utsätts för indunstning för avdrivning av luktförorsakande komponenter och andra flyktiga komponenter frän produkten, vilken indunstning utförs i en kortvägsevaporator uppvisande en avdunstningsyta och en i dess närhet befintlig kondensator väri de avdunstade komponentema, som skall avdrivas, kondenseras, varvid en talloljehartsester med lag luktnivä utvinns ur 10 evaporatom.
2. Förfarande enligt patentkrav 1, kännetecknat av att man i evaporatom använder ett tryck pä mellan ca. 0,1-20 mbar, företrädesvis ca. 0,2-4 mbar, och att temperaturen hos avdunstningsytan är mellan ca. 150-280°C, företrädesvis ca. 220-260°C. 15
3. Förfarande enligt patentkrav 1 eller 2, kännetecknat av att man som hartset som skall förestras använder ett talloljeharts som sädant eller modifierat medelst i och för sig kända sätt.
4. Förfarande enligt patentkrav 3, kännetecknat av att hartset har en uppmjukningspunkt pä ca. 55-75°C, företrädesvis ca. 65-70°C. > ·' 20
5. Förfarande enligt nägot av föregäende patentkrav, kännetecknat av att den vid . *’ förestringen använda polyolen utgörs av glycerol eller pentaerytritol. * 1 ' · »
6. Förfarande enligt nägot av föregäende patentkrav, kännetecknat av att , : ·, mängden av den vid förestringen använda polyolen i förhällande tili mängden harts * * * är ca. 0,9-1,1:1 och att syratalet hos produkten under förestringen sjunker tili en 25 nivä av ca. 35-15, företrädesvis ca. 28-20. * »
7. Förfarande enligt nägot av föregäende patentkrav, kännetecknat av att det , ‘ , under indunstningssteget frän produkten avdrivs ca. 5-20 vikt-% av en substans som ‘ ; » . huvudsakligen bestär av en blandning av neutralämnen, fettsyra och harts.
: 8. Förfarande enligt nägot av föregäende patentkrav, kännetecknat av att , 30 syratalet hos den frän indunstningen erhällna talloljehartsestem är ca. 0,2-10, företrädesvis ca. 2-6.
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI971663A FI112247B (sv) | 1997-04-18 | 1997-04-18 | Framställning av en talloljehartsester med låg luktnivå |
| NZ330181A NZ330181A (en) | 1997-04-18 | 1998-04-09 | Preparation of a tall oil rosin ester (typically from sulphate pulping of paper) with a low odour level using a short path evaporator |
| RU98107006/04A RU2208621C2 (ru) | 1997-04-18 | 1998-04-09 | Способ получения сложного эфира талловой канифоли с низким уровнем запаха |
| CA002234911A CA2234911A1 (en) | 1997-04-18 | 1998-04-16 | Preparation of a tall oil rosin ester with a low odor level |
| DE69828328T DE69828328T2 (de) | 1997-04-18 | 1998-04-17 | Herstellung von Tallöl Kolophonium Ester mit verringertem Geruch |
| EP98660033A EP0872528B1 (en) | 1997-04-18 | 1998-04-17 | Preparation of a tall oil rosin ester with a low odor level |
| ES98660033T ES2236885T3 (es) | 1997-04-18 | 1998-04-17 | Preparacion de ester de colofonia de aceite de tall con un bajo nivel de olor. |
| JP10108110A JPH10298496A (ja) | 1997-04-18 | 1998-04-17 | 悪臭レベルの低いタル油ロジンエステルの作成方法 |
| AT98660033T ATE286098T1 (de) | 1997-04-18 | 1998-04-17 | Herstellung von tallöl kolophonium ester mit verringertem geruch |
| CN98106654A CN1113944C (zh) | 1997-04-18 | 1998-04-17 | 气味水平低的妥尔油松香酯的制备方法 |
| US09/063,665 US5969092A (en) | 1997-04-18 | 1998-04-21 | Preparation of a tall oil rosin ester with a low odor level |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI971663 | 1997-04-18 | ||
| FI971663A FI112247B (sv) | 1997-04-18 | 1997-04-18 | Framställning av en talloljehartsester med låg luktnivå |
| US6366598 | 1998-04-21 | ||
| US09/063,665 US5969092A (en) | 1997-04-18 | 1998-04-21 | Preparation of a tall oil rosin ester with a low odor level |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI971663A0 FI971663A0 (sv) | 1997-04-18 |
| FI971663A FI971663A (sv) | 1998-10-19 |
| FI112247B true FI112247B (sv) | 2003-11-14 |
Family
ID=26160374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI971663A FI112247B (sv) | 1997-04-18 | 1997-04-18 | Framställning av en talloljehartsester med låg luktnivå |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5969092A (sv) |
| EP (1) | EP0872528B1 (sv) |
| JP (1) | JPH10298496A (sv) |
| CN (1) | CN1113944C (sv) |
| AT (1) | ATE286098T1 (sv) |
| CA (1) | CA2234911A1 (sv) |
| DE (1) | DE69828328T2 (sv) |
| ES (1) | ES2236885T3 (sv) |
| FI (1) | FI112247B (sv) |
| NZ (1) | NZ330181A (sv) |
| RU (1) | RU2208621C2 (sv) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA02002226A (es) * | 2001-03-14 | 2002-09-30 | Rohm & Haas | Metodo para preparar prepolimeros con funcionalidad de isocianato con baja concentracion de monomeros de isocianato residual. |
| US20060122309A1 (en) * | 2004-12-02 | 2006-06-08 | Grah Michael D | Intercalated layered silicate |
| AU2006283679B2 (en) * | 2005-08-19 | 2011-05-19 | Cryovac, Inc. | Film comprising silicate platelets exfoliated from phospholipid-intercalated layered silicate |
| EP1951852B1 (en) * | 2005-10-26 | 2016-04-13 | SunPine AB | Automotive fuels and fine chemicals from crude tall oil |
| EP2012185B1 (en) * | 2006-04-21 | 2013-06-05 | Kao Corporation | Toner |
| US20110213120A1 (en) * | 2010-03-01 | 2011-09-01 | Arizona Chemical Company | Rosin esters for non-woven applications, methods of making and using and products therefrom |
| FI20106252A0 (sv) | 2010-11-26 | 2010-11-26 | Upm Kymmene Corp | Förfarande och system för framställning av bränslekomponenter |
| RU2569081C2 (ru) * | 2011-04-11 | 2015-11-20 | Аризона Кемикал Компани, Ллс | Сложные эфиры канифоли для нетканых материалов |
| CN102337078B (zh) * | 2011-07-07 | 2013-10-16 | 景东力奥林产集团林业化工有限公司 | 松香树脂生产工艺 |
| WO2014200567A1 (en) | 2013-06-14 | 2014-12-18 | Arizona Chemical Company, Llc | Rosin ester tackifiers for pressure-sensitive adhesives |
| CN103436176A (zh) * | 2013-08-28 | 2013-12-11 | 梧州市嘉盈树胶有限公司 | 高软化点松香甘油酯的制备方法 |
| KR102167583B1 (ko) * | 2014-06-30 | 2020-10-19 | 코오롱인더스트리 주식회사 | 냄새가 개선된 석유수지의 제조방법 |
| KR102464692B1 (ko) * | 2015-03-26 | 2022-11-09 | 크라톤 케미칼, 엘엘씨 | 로진 에스테르와 에틸렌 중합체를 포함하는 조성물 |
| KR102219073B1 (ko) * | 2015-03-31 | 2021-02-23 | 코오롱인더스트리 주식회사 | 석유 수지의 제조방법 및 상기 방법으로 제조된 핫멜트용 조성물 |
| KR101868052B1 (ko) * | 2016-05-09 | 2018-06-18 | 주식회사 엘에스켐코리아 | 로진 에스테르 조성물의 제조 방법, 로진 에스테르 조성물 및 상기 로진 에스테르 조성물을 포함한 화장품용 조성물 |
| EP3587528B1 (en) | 2018-06-22 | 2021-05-26 | 3M Innovative Properties Company | Process of manufacturing a pressure sensitive adhesive having low voc characteristics |
| US11041095B2 (en) | 2019-05-22 | 2021-06-22 | Kraton Polymers Llc | Desulfurized tall oil and derivatives thereof |
| US11279849B2 (en) | 2020-05-21 | 2022-03-22 | Kraton Polymers Llc | Deodorized rosin ester and methods for making |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3709793A (en) * | 1969-07-10 | 1973-01-09 | Foster Wheeler Corp | Control of environmental pollution in tall oil fractionation |
| GB1296480A (sv) * | 1970-08-10 | 1972-11-15 | ||
| US3780013A (en) * | 1972-12-18 | 1973-12-18 | Arizona Chem | Preparation of color improved tall oil rosin pentaerythritol esters |
| US4548746A (en) * | 1984-05-14 | 1985-10-22 | Westvaco Corporation | Rosin pentaerythritol ester preparation improvement |
| US4659514A (en) * | 1986-01-27 | 1987-04-21 | Ciba-Geigy Corporation | Esterification of rosin acid with calcium hydroxybenzyl phosphonate catalyst |
| US4775497A (en) * | 1986-10-24 | 1988-10-04 | Ciba-Geigy Corporation | Esterification process with calcium hydroxyaryl phosphonate-organosilicon heterocycle catalyst system |
| US4962186A (en) * | 1989-07-10 | 1990-10-09 | Union Camp Corporation | Method of improving the color of tall oil rosin esters by recrystallizing and distilling rosin followed by esterifying |
| US5084554A (en) * | 1990-01-22 | 1992-01-28 | Hercules Incorporated | Treating polymerized rosin with sodium hydroxy methane sulfonate to improve color stability |
| DE4308109A1 (de) * | 1993-03-15 | 1994-09-22 | Hoechst Ag | Mit Phenolharz modifizierte Naturharzsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung in Druckfarben |
| DE4330337A1 (de) * | 1993-09-08 | 1995-03-09 | Hoechst Ag | Verfahren zur Herstellung von modifizierten Naturharzsäureestern |
-
1997
- 1997-04-18 FI FI971663A patent/FI112247B/sv not_active IP Right Cessation
-
1998
- 1998-04-09 NZ NZ330181A patent/NZ330181A/en not_active IP Right Cessation
- 1998-04-09 RU RU98107006/04A patent/RU2208621C2/ru not_active IP Right Cessation
- 1998-04-16 CA CA002234911A patent/CA2234911A1/en not_active Abandoned
- 1998-04-17 CN CN98106654A patent/CN1113944C/zh not_active Expired - Fee Related
- 1998-04-17 EP EP98660033A patent/EP0872528B1/en not_active Expired - Lifetime
- 1998-04-17 ES ES98660033T patent/ES2236885T3/es not_active Expired - Lifetime
- 1998-04-17 JP JP10108110A patent/JPH10298496A/ja active Pending
- 1998-04-17 DE DE69828328T patent/DE69828328T2/de not_active Expired - Lifetime
- 1998-04-17 AT AT98660033T patent/ATE286098T1/de not_active IP Right Cessation
- 1998-04-21 US US09/063,665 patent/US5969092A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69828328T2 (de) | 2005-12-08 |
| FI971663A0 (sv) | 1997-04-18 |
| EP0872528B1 (en) | 2004-12-29 |
| NZ330181A (en) | 1998-06-26 |
| US5969092A (en) | 1999-10-19 |
| ES2236885T3 (es) | 2005-07-16 |
| CN1197097A (zh) | 1998-10-28 |
| DE69828328D1 (de) | 2005-02-03 |
| CA2234911A1 (en) | 1998-10-18 |
| JPH10298496A (ja) | 1998-11-10 |
| RU2208621C2 (ru) | 2003-07-20 |
| ATE286098T1 (de) | 2005-01-15 |
| FI971663A (sv) | 1998-10-19 |
| EP0872528A3 (fr) | 1998-12-02 |
| CN1113944C (zh) | 2003-07-09 |
| EP0872528A2 (en) | 1998-10-21 |
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