NO152513B - Polymeriserbar polyuretanblanding - Google Patents
Polymeriserbar polyuretanblanding Download PDFInfo
- Publication number
- NO152513B NO152513B NO793432A NO793432A NO152513B NO 152513 B NO152513 B NO 152513B NO 793432 A NO793432 A NO 793432A NO 793432 A NO793432 A NO 793432A NO 152513 B NO152513 B NO 152513B
- Authority
- NO
- Norway
- Prior art keywords
- cumylphenyl
- mixture
- parts
- polymerizable
- polyuretan
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 13
- JUOYFQPDLANFBJ-UHFFFAOYSA-N 2-[[2-(2-phenylpropan-2-yl)phenoxy]methyl]oxirane Chemical compound C=1C=CC=C(OCC2OC2)C=1C(C)(C)C1=CC=CC=C1 JUOYFQPDLANFBJ-UHFFFAOYSA-N 0.000 claims description 9
- 229920002635 polyurethane Polymers 0.000 claims description 8
- 239000004814 polyurethane Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 239000004014 plasticizer Substances 0.000 description 10
- 239000003085 diluting agent Substances 0.000 description 4
- -1 glycidyl ethers Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- KGUOKRPZKAUXBR-UHFFFAOYSA-N 1-[2-hydroxy-5-(2-phenylpropan-2-yl)phenyl]ethanone Chemical compound C1=C(O)C(C(=O)C)=CC(C(C)(C)C=2C=CC=CC=2)=C1 KGUOKRPZKAUXBR-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
- 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)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
- Materials For Medical Uses (AREA)
Description
Foreliggende oppfinnelse angår en polymeriserbar blanding inneholdende cumylfenyl-glycidyleter eller cumylfenyl-ester som ikke reaktive mykningsmidler.
Det er således nu funnet at cumylfenyl-glycidyl-etere og cumylfenyl-estere er egnet som ikke-reaktive mykningsmidler for polyuretaner og i h.h.t. dette angår oppfinnelsen polymeriser-bare blandinger som karakteriseres ved at de består av 10 - 100 vektdeler cumylfenyl-glycidyl-eter eller cumylfenyl-ester med formelen
9
der R betyr en acylgruppe, C-R' der R' betyr alkyl, aryl eller aralkyl med 1-12 karbonatomer, eller en glycidylgruppe med 3-6 karbonatomer, og 100 deler uretanharpiks.
Fortrinnsvis er R<1> metyl^ etyl eller en langkjedet alkyl, og glycidylgruppen er CH^CH-fcH. Noen av disse forbindelser er kjent på området. Acetylderivatet er beskrevet Tsivuning og medarbeidere i "Biol.Akliv. Soldin.", 1968, 172-175 (Russisk)-. Imidlertid er en del nye forbindelser, nemlig glycidyletere, benzoatesteren og høyere acylestere av cumylfenol. I sist-nevnte gruppe er de viktigste estere hvor R' har fra 6-10 C-atomer.
Som ikkereaktive mykningsmidler brukes fra 15-60 vekt-%, fortrinnsvis fra 20-40 vekt-% av den egnede cumylfenolester, basert på harpiksens totalvekt.
Ved anvendelser i henhold til oppfinnelsen hvor cumylfenoler brukes som ikkereaktive mykningsmidler, blir cumylfenolfor-bindelsen først blandet med harpiksen samt andre ønskede bestanddeler. Blandingen tilføres polymerisasjonsreaktoren,
og harpiksen polymeriseres på kjent måte.
De harpikser som herdes og formes ved utførelse av oppfinnelsen kan generelt kalles "flytende termoherdende harpikser".
Med dette menes harpikser som er i væskeform under bruksbeting-elsene og omfatter støpeharpikser, d.v.s. flytende monomerer eller ufullstendig polymeriserte polymerer, vanligvis inneholdende katalysatorer eller herdemidler, og som blir hårde etter at de støpes i former, og belegningsharpikser, d.v.s. flytende monomerer eller ufullstendig polymeriserte polymerer, eventulet i oppløsningsmiddel eller ikke-oppløsende drøynings-middel og som anvendes ved støping, dreiing, børsting, rulling, sprøyting eller dypping. Disse omfatter lakker og malinger, emaljer, samt støpe- og "potting"-harpikser.
Harpiksene som finner anvendelse i forbindelse med foreliggende oppfinnelse er polyuretaner, og disse kan kort beskrives slik: Polyuretaner er en familie av harpikser som fremstilles ved å omsette diisocyanater med organiske forbindelser som innehold-er to eller flere aktive atomer under dannelse av polymerer med frie isocyanatgrupper. En detaljert beskrivelse av disse harpikser finnes i US-PS 3 060 137. Disse grupper vil under påvirkning av varme eller katalysator reagere med hverandre eller med vann, glykoler etc. under dannelse av termoherdende stoffer.
Eksempel 1.
Eksemplet viser bruk av cumylfenylglycidyl-eter som ikkereaktivt fortynningsmiddel for polyuretan.
Del 1
Det ble laget cumylfenylglycidyleter som følger:
En 3-liters kolbe utstyrt med mekanisk rører, termometer,
dråpetrakt og ytre oppvarming og avkjøling ble påfylt i rekke-følge: 1 liter benzen, 1 liter 4,5 vekt-% vandig natriumhyd-
roksyd og 1 mol cumylfenol. Cumylfenolbenzendispersjonen som dannet seg etter blanding, ble avkjølt til 10-15°C, blandet og holdt ved 10-15°C under tilsetning av 1,1 mol epiklorhydrin i løpet av 4 timer. Etter tilsetning av klorhydrinet ble reak-sjonsblandingen oppvarmet til 50°C i 8 timer. De to faser som dannet seg, ble separert og vannfasen kastet. Den organiske fase ble vasket tre ganger med kaldt vann og gjenværende organ-isk stoff fraskilt. 190 g (76 mol-%) lysegul olje med koke-
punkt 258-263°C/5 mm Hg ble fremstilt. Oljen hadde et epoksyd-
tall målt ved MgC12~HC1-titrering lik 3,72 mekv/g, mens det teoretiske epoksydtall for cumylfenylglycidyleter er 3,73 mekv/g.
Del II
Fem polyuretanblandinger inneholdende 100 deler polyuretan
("Adiprene CM"), et reaksjonsprodukt mellom diisocyanat og polyalkylenterglykol, 30 deler HAF sotsvart, 1 del merkaptobenzo-tiazol, 4 deler 2,2<1->benzotiazyldisulfid, 0,5 deler sinkklorid-2,2'-benzotiadisulfid, 0,75 deler svovel og 0,5 deler kadmium-
stearat ble fremstilt. Den første blanding inneholdt intet mykningsmiddel eller reaktivt fortynningsmiddel. Andre, tredje og fjerde sammensetning inneholdt dioktylftalat (DOP), dioktyl-sebacat (DOS) og en tyngre aromatisk naftaolje som fortynningsmiddel ("Sunex 790"), respektivt. De første to tilsetninger er vanlige ikkereaktive plastiseringsmidler, mens det fjerde er et reaktivt mykningsmiddel. Til en femte blanding settes 15 vektdeler cumylfenylglycidyleter (CGE) i henhold til oppfinnelsen. Preparatene ble herdet 60 min. ved 140°C og de fysikal-
ske egenskapene prøvet. Resultatene fremgår av følgende tabell:
Ovenstående tabell viser klart at cumylfenylglycidyleter
ifølge oppfinnelsen effektivt reduserer polyuretanpreparatets strekkmodul. De viser videre at eteren er vesentlig bedre enn andre mykningsmidler siden de herdede blandinger hadde mye bedre strekkfasthet og oppnådde minste tap av hårdhet av de prøvede blandinger. Denne kombinasjon av egenskaper er særlig egnet, hvdlket fagfolk lett vil innse og høyst over-raskende og uventet. Selv for naftaolje, det andre reaktive fortynningsmiddel, var strekkfastheten mye bedre. Dette kan tilskrives glycidyleteren som forbedrer herdeprosessen.
Eksempel 2.,
Eksemplet viser bruk av acetyl-p-cumylfenol som ikkereaktivt mykningsmiddel for uretanharpiks. Man laget følgende blandinger:
Ovenstående tall viser at acetyl-p-cumylfenol gir en kombinasjon av høyere forlengelse og bedre strekkfasthet og lignende strekkmodul som de kjente mykningsmidler for uretaner.
Claims (2)
1. Polymeriserbar polyuretanblanding, karakterisert ved at den består av 10 - 100 vektdeler cumylfenyl-glycidyl-eter eller cumylfenyl-ester med formelen
9
hvor R betyr en acylgruppe, C-R' der R' betyr alkyl, aryl eller aralkyl med 1-12 karbonatomer, eller en glycidylgruppe med 3-6 karbonatomer, og 100 deler uretanharpiks.
2. Blanding ifølge krav 1,karakterisert ved at R i formelen for cumylfenyl—forbindelsen betegn-er gruppen
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 |
|---|---|
| NO793432L NO793432L (no) | 1977-10-03 |
| NO152513B true NO152513B (no) | 1985-07-01 |
| NO152513C NO152513C (no) | 1985-10-09 |
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 |
| NO793432A NO152513C (no) | 1976-03-31 | 1979-10-25 | Polymeriserbar polyuretanblanding. |
| 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 |
Family Applications Before (1)
| 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 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
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) | DE2660982C2 (no) |
| FR (1) | FR2353593A1 (no) |
| GB (5) | GB1553112A (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 |
| CN102428061B (zh) * | 2009-05-19 | 2015-09-30 | 本州化学工业株式会社 | 三苯酚类及其单酯取代物的制造方法及4-酰基芳烷基苯酚衍生物 |
| DE102011015193A1 (de) * | 2011-03-25 | 2012-09-27 | Momentive Specialty Chemicals Gmbh | Epoxidierte Arylalkylphenole |
| US20160075891A1 (en) * | 2014-09-16 | 2016-03-17 | Eastman Chemical Company | Polymeric compositions with improved noise suppression |
| US20160075855A1 (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 | |||
| BE530703A (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 GB42897/78A patent/GB1553112A/en not_active Expired
- 1976-05-13 GB GB42965/78A patent/GB1553114A/en not_active Expired
- 1976-05-13 GB GB43056/78A patent/GB1553115A/en not_active Expired
- 1976-05-13 GB GB42964/78A patent/GB1553113A/en not_active Expired
- 1976-05-13 GB GB19695/76A patent/GB1553111A/en not_active Expired
- 1976-05-14 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 DE2660982A patent/DE2660982C2/de not_active Expired
- 1976-05-25 DE DE2623473A patent/DE2623473C2/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 IT IT67693/77A patent/IT1073499B/it active
- 1977-03-30 BE BE176263A patent/BE853049A/xx not_active IP Right Cessation
-
1978
- 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
- 1978-11-02 JP JP13462878A patent/JPS5488998A/ja active Granted
-
1979
- 1979-05-31 AU AU47665/79A patent/AU515300B2/en not_active Expired
- 1979-10-25 NO NO793432A patent/NO152513C/no unknown
- 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
-
1986
- 1986-06-25 JP JP61149332A patent/JPS627760A/ja active Granted
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