NO151203B - Myknet vinylkloridharpiks. - Google Patents
Myknet vinylkloridharpiks. Download PDFInfo
- Publication number
- NO151203B NO151203B NO793433A NO793433A NO151203B NO 151203 B NO151203 B NO 151203B NO 793433 A NO793433 A NO 793433A NO 793433 A NO793433 A NO 793433A NO 151203 B NO151203 B NO 151203B
- Authority
- NO
- Norway
- Prior art keywords
- vinyl chloride
- chloride resin
- cumylphenol
- soft vinyl
- weight
- Prior art date
Links
- 239000011347 resin Substances 0.000 title claims description 10
- 229920005989 resin Polymers 0.000 title claims description 10
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title claims description 5
- CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 claims description 10
- 239000004014 plasticizer Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- -1 benzoate ester Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- AHSGHEXYEABOKT-UHFFFAOYSA-N 2-[2-(2-benzoyloxyethoxy)ethoxy]ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOCCOC(=O)C1=CC=CC=C1 AHSGHEXYEABOKT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- IKYNDBQJTHKDIL-UHFFFAOYSA-N [4-(2-phenylpropan-2-yl)phenyl] benzoate Chemical compound C=1C=C(OC(=O)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 IKYNDBQJTHKDIL-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1444—Monoalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/145—Compounds containing one epoxy group
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/105—Esters; Ether-esters of monocarboxylic acids with phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Epoxy Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Materials For Medical Uses (AREA)
Description
Foreliggende oppfinnelse angår en myknet vinylkloridharpiks som som ikke-reaktivt mykningsmiddel inneholder cumylderi-vater. Mere spesielt angår oppfinnelsen myknet vinylkloridharpiks inneholdende en benzyl- eller høyere alkylester av cumylfenol.
Ifølge oppfinnelsen har man som nevnt funnet at estere av cumylfenol, særlig benzoat og høyere acylestere, er egnet som ikke-reaktive mykningsmidler i hård polyvinylklorid.
Man oppnår ved dette bl.a. at den ferdige plastens pris her vesentlig kan reduseres.
Cumylfenolderivater kan generelt ha følgende formel:
0
ii
hvor R betegner en acylgruppe, C-R', hvor R" betegner alkyl, aryl eller aralkyl med 1-12 C-atomer, eller en glycidylgruppe med 3-6 C-atomer. Fortrinnsvis er R' metyl, etyl eller en langkjedet alkyl, og glycidylgruppen er CI^Cfl-cJH. Noen av disse forbindelser er kjent på området. Acetylderivatet er beskrevet av Tsivunin og medarbeidere i Biol. Akliv. Soldin., 1968, 172-175 (Russisk). Imidlertid er en del nye forbindelser, nemlig glycidyleteren, benzoatesteren og høyere acetylestere av cumylfenol. I sistnevnte gruppe er de viktigste estere hvor R<1> har fra 6-10 C-atomer.
I henhold til dette angår foreliggende oppfinnelse en myknet vinylkloridharpiks som karakteriseres ved at den som mykningsmiddel inneholder 15 til 60 vekt-% av en benzyl- eller høyere alkylester av cumylfenol der alkylgruppen har fra 6 til 10 karbonatomer.
Ved anvendelser i henhold til oppfinnelsen hvor cumylfenol-estere brukes som ikke-reaktive mykningsmidler, blir cumyl-fenolforbindelsen først blandet med harpiksen samt andre ønskede bestanddeler. Blandingen tilføres polymerisasjons-reaktoren, og harpiksen polymeriseres på kjent måte.
Harpiksen som benyttes i forbindelse med foreliggende oppfinnelse er som nevnt polyvinylklorid.
Hårde polyvinylkloridharpikser inneholder eventuelt drøy-ningsmidler, pigmenter, stabiliseringsmidler og en liten del mykningsmiddel hvor mengden av mykningsmiddel er util-strekkelig til å redusere strekkfastheten til under ca.
2
140 kg/cm .
Eksempel 1
Eksemplet viser anvendelse av p-cumylfenylbenzoat som be-arbeidelseshjelpestoff og smøremiddel for ekstrudering av stiv PVC.
Del I
Man fremstilte cumylbenzylbenzoat på følgende måte: 1 mol cumylfenol ble oppløst i 600 ml benzen inneholdende 1,2 mol trietylamin i en 2-liters glassbeholder forsynt med utstyr for ytre oppvarming og avkjøling. Reaksjonsblandingen ble avkjølt til 15-20°C og holdt på dette nivå under tilsetning av 1,1 mol benzoylklorid i løpet av 1,5 timer. Etter, avsluttet tilsetning ble den dannede oppslemming oppvarmet til 40-45°C
i 1 time og derpå avkjølt til romtemperatur og filtrert. Filterkaken ble vasket med 200 ml toluen, og de samlede vaske-og filtratvæsker ble destillert og ga 214,9 g (69 mol-%) lysegul olje med kokepunkt 261-265°C/0,5 mm Hg, spesifikk vekt ved 55°C lik 1,082 og viskositet ved 55°C lik 215 eps. Ved h Gn.sta.nd stivnet oljen til et hvitt fast stoff med smelte-punkt 43-46,5°C.
Del II
Man forblandet de følgende sammensetninger i en hurtigrører ("Disona") ved romtemperatur og ekstruderte dem gjennom en vanlig 10 cm rørdyse ved 180 + 10°C under fast matnings-effekt. Ekstrudatets fysikalske egenskaper og ekstruderings-hastighet fremgår også av tabellen.
Tilsetning av benzoatesteren ga en 24% økning av ekstruder-ingshastigheten og 18% bedring av bøyningsstivheten uten redu-sert slagfasthet. Andre eksperimenter viser at benzoatesteren er enestående på denne måte og at lignende forbedringer ikke oppnås med andre cumylfenolderivater.
Eksempel 2
Eksemplet viser bruk av høyere alkylestere av cumylfenol som ikke-reaktivt mykningsmiddel i polyvinylklorid.
Del I
Cumylfenol-2-etylheksanoat ble fremstilt etter følgende frem-gangsmåte: en 2-liters kolbe forsynt med mekanisk rører, de-stillasjonskolonne med 10 teoretiske trinn, automatisk tilbake-løpseparator, damptermometere og effektregulator, kjøler, mot-takerbeholdere og utvendige oppvarmings- og avkjølingsorganer ble påfylt 2 mol cumylfenylacetat, 5 mol 2-etylheksansyre og 5g 98% svovelsyre. Man oppvarmet utenfra og oppsamlet destil-latet ved et tilbakeløpsforhold lik 20:1 og en damptemperatur under 120°C ved atmosfæretrykk. Man fikk ialt 64 ml destillat etter 24 timer. Gjenværende bestanddeler ble avkjølt til romtemperatur og ekstrahert fem ganger med 2 liter 8% natrium-bikarbonat, tørket over vannfri Na2S04 og destillert og ga 408 g (58 mol-%) lysegul olje. Oljen hadde et kokepunkt på 252-257°C/0,2 mm Hg, spesifikk vekt 20/20°C lik 1,045 og et forsåpningstall på 2,82 mekv./g. Cumylfenyl-2-etylheksanoat-esteren har et teoretisk forsåpningstall på 2,85 mekv./g.
Del II
For å vise virkningen av 2-etylheksanoatester som mykningsmiddel for myk polyvinylklorid, ble 100 deler PVC-harpiks med midlere molvekt blandet med 4 0 vektdeler 5 ym kalsiumkarbonat og 2 vektdeler stabiliseringsmiddel "Thermozard S". Man laget tre sammensetninger. Den første inneholdt 30 vektdeler tri-etylenglykoldibenzoat, den andre 30 vektdeler dioktylftalat og den tredje 30 vektdeler cumylfenyl-2-etylheksanoat i henhold til oppfinnelsen. Nedenstående tabell viser de fysikalske egenskaper for blandingen etter herding:
Ovenstående tabell viser klart at forbindelsen i henhold til oppfinnelsen effektivt reduserer sammensetningens strekkmodul. Sammenlignet med andre mykningsmidler hadde sammensetningen inneholdende 2-etylheksanoatester den beste strekkfasthet og bruddforlengelse.
Claims (1)
- Myknet vinylkloridharpiks, karakterisert ved at den som mykningsmiddel inneholder 15-60 vekt-% av en benzyl- eller høyere alkylester av cumylfenol der alkylgruppen har fra 6-10 karbonatomer.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/672,425 US4102862A (en) | 1976-03-31 | 1976-03-31 | Application of cumylphenol and derivatives thereof in plastic compositions |
Publications (3)
Publication Number | Publication Date |
---|---|
NO793433L NO793433L (no) | 1977-10-03 |
NO151203B true NO151203B (no) | 1984-11-19 |
NO151203C NO151203C (no) | 1985-02-27 |
Family
ID=24698493
Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO770984A NO145723C (no) | 1976-03-31 | 1977-03-21 | Derivater av cumylfenol til anvendelse som additiver i plast |
NO793431A NO153008C (no) | 1976-03-31 | 1979-10-25 | Polymeriserbar harpiksblanding. |
NO793433A NO151203C (no) | 1976-03-31 | 1979-10-25 | Myknet vinylkloridharpiks |
NO793430A NO145797C (no) | 1976-03-31 | 1979-10-25 | Herdbar blanding omfattende epoksyharpiks, alifatisk polyamin og substituert fenol |
NO793432A NO152513C (no) | 1976-03-31 | 1979-10-25 | Polymeriserbar polyuretanblanding. |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO770984A NO145723C (no) | 1976-03-31 | 1977-03-21 | Derivater av cumylfenol til anvendelse som additiver i plast |
NO793431A NO153008C (no) | 1976-03-31 | 1979-10-25 | Polymeriserbar harpiksblanding. |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO793430A NO145797C (no) | 1976-03-31 | 1979-10-25 | Herdbar blanding omfattende epoksyharpiks, alifatisk polyamin og substituert fenol |
NO793432A NO152513C (no) | 1976-03-31 | 1979-10-25 | Polymeriserbar polyuretanblanding. |
Country Status (17)
Country | Link |
---|---|
US (1) | US4102862A (no) |
JP (6) | JPS5928541B2 (no) |
AU (2) | AU504583B2 (no) |
BE (1) | BE853049A (no) |
CA (1) | CA1087346A (no) |
CH (1) | CH628075A5 (no) |
DE (2) | DE2623473C2 (no) |
FR (1) | FR2353593A1 (no) |
GB (5) | GB1553113A (no) |
IN (1) | IN145557B (no) |
IT (1) | IT1073499B (no) |
LU (1) | LU76928A1 (no) |
MX (1) | MX146590A (no) |
NL (1) | NL185352C (no) |
NO (5) | NO145723C (no) |
SE (1) | SE432106B (no) |
ZA (1) | ZA762956B (no) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1153770A (en) * | 1978-07-20 | 1983-09-13 | Salvatore J. Monte | Cumylphenol derivatives |
US4341678A (en) * | 1979-09-17 | 1982-07-27 | Inmont Corporation | Water-borne epoxy-phenolic coating compositions |
GB2140017B (en) * | 1983-03-08 | 1986-11-19 | Borden Inc | Phenolic resin binder compositions exhibiting low fume evolution in use |
US4668757A (en) * | 1984-03-26 | 1987-05-26 | Gus Nichols | Use of aromatic amines for setting epoxide resins |
US4522747A (en) * | 1984-06-26 | 1985-06-11 | Rca Corporation | Capacitance electronic disc molding compositions |
JPS61102651U (no) * | 1984-12-07 | 1986-06-30 | ||
GB8529496D0 (en) * | 1985-11-29 | 1986-01-08 | Scott Bader Co | Resurfacing of paths &c |
JPS62184452U (no) * | 1986-05-09 | 1987-11-24 | ||
US4683283A (en) * | 1986-06-23 | 1987-07-28 | Ashland Oil, Inc. | Latent accelerators for epoxide curing |
JPS63226542A (ja) * | 1987-03-17 | 1988-09-21 | Matsushita Electric Ind Co Ltd | 床置型複合加熱装置 |
US4994505A (en) * | 1988-11-15 | 1991-02-19 | Borden, Inc. | Binder compositions comprising low molecular weight poly(orthomethylolated) phenolic compound and novolac resin |
US20040101681A1 (en) * | 2002-11-21 | 2004-05-27 | Campbell Richard Vest | Filler potting cable termination system and process |
US7294684B2 (en) * | 2005-11-11 | 2007-11-13 | Dover Chemical Corporation | Dimeric and polymeric alkylphenol polysulfides |
US9090547B2 (en) | 2009-05-19 | 2015-07-28 | Honshu Chemical Industry Co., Ltd. | Method for producing trisphenols and monoester-substituted products thereof, and 4-acylaralkylphenol derivatives |
DE102011015193A1 (de) * | 2011-03-25 | 2012-09-27 | Momentive Specialty Chemicals Gmbh | Epoxidierte Arylalkylphenole |
US20160075890A1 (en) * | 2014-09-16 | 2016-03-17 | Eastman Chemical Company | Polymeric compositions with improved noise suppression |
US20160075857A1 (en) | 2014-09-16 | 2016-03-17 | Eastman Chemical Company | Polymeric compositions with improved noise suppression |
CN111116369B (zh) * | 2019-10-10 | 2020-11-24 | 苏州巨峰新材料科技有限公司 | 一种活性酯化合物及其制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE495431A (no) * | 1949-04-29 | |||
NL95050C (no) * | 1953-07-29 | |||
US3637902A (en) * | 1969-08-26 | 1972-01-25 | Celanese Coatings Co | Epoxide resins cured with amine-glycidyl ester adducts in admixture with a phenolic accelerator |
CH545289A (de) * | 1970-03-23 | 1973-12-15 | Ciba Geigy Ag | Verfahren zur Herstellung eines Piperidinderivates und seine Anwendung |
US3763102A (en) * | 1972-05-03 | 1973-10-02 | Basf Ag | Production of moldings and coatings by the reaction of a polyepoxide and a polyamine |
-
1976
- 1976-03-31 US US05/672,425 patent/US4102862A/en not_active Expired - Lifetime
- 1976-05-13 GB GB42964/78A patent/GB1553113A/en not_active Expired
- 1976-05-13 GB GB19695/76A patent/GB1553111A/en not_active Expired
- 1976-05-13 GB GB42965/78A patent/GB1553114A/en not_active Expired
- 1976-05-13 GB GB42897/78A patent/GB1553112A/en not_active Expired
- 1976-05-13 GB GB43056/78A patent/GB1553115A/en not_active Expired
- 1976-05-14 AU AU13956/76A patent/AU504583B2/en not_active Expired
- 1976-05-15 IN IN853/CAL/76A patent/IN145557B/en unknown
- 1976-05-18 ZA ZA762956A patent/ZA762956B/xx unknown
- 1976-05-25 DE DE2623473A patent/DE2623473C2/de not_active Expired
- 1976-05-25 DE DE2660982A patent/DE2660982C2/de not_active Expired
- 1976-05-31 JP JP51063451A patent/JPS5928541B2/ja not_active Expired
-
1977
- 1977-02-24 CA CA272,525A patent/CA1087346A/en not_active Expired
- 1977-03-08 FR FR7706792A patent/FR2353593A1/fr active Granted
- 1977-03-10 LU LU76928A patent/LU76928A1/xx unknown
- 1977-03-11 SE SE7702794A patent/SE432106B/xx not_active IP Right Cessation
- 1977-03-21 NO NO770984A patent/NO145723C/no unknown
- 1977-03-28 CH CH388977A patent/CH628075A5/de not_active IP Right Cessation
- 1977-03-29 NL NLAANVRAGE7703357,A patent/NL185352C/xx not_active IP Right Cessation
- 1977-03-30 MX MX168570A patent/MX146590A/es unknown
- 1977-03-30 BE BE176263A patent/BE853049A/xx not_active IP Right Cessation
- 1977-03-30 IT IT67693/77A patent/IT1073499B/it active
-
1978
- 1978-11-02 JP JP13462878A patent/JPS5488998A/ja active Granted
- 1978-11-02 JP JP13462978A patent/JPS5488958A/ja active Granted
- 1978-11-02 JP JP53134627A patent/JPS6040452B2/ja not_active Expired
- 1978-11-02 JP JP53134630A patent/JPS6028308B2/ja not_active Expired
-
1979
- 1979-05-31 AU AU47665/79A patent/AU515300B2/en not_active Expired
- 1979-10-25 NO NO793431A patent/NO153008C/no unknown
- 1979-10-25 NO NO793433A patent/NO151203C/no unknown
- 1979-10-25 NO NO793430A patent/NO145797C/no unknown
- 1979-10-25 NO NO793432A patent/NO152513C/no unknown
-
1986
- 1986-06-25 JP JP61149332A patent/JPS627760A/ja active Granted
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