CA1076727A - Modified phenolic tackifier - Google Patents
Modified phenolic tackifierInfo
- Publication number
- CA1076727A CA1076727A CA263,965A CA263965A CA1076727A CA 1076727 A CA1076727 A CA 1076727A CA 263965 A CA263965 A CA 263965A CA 1076727 A CA1076727 A CA 1076727A
- Authority
- CA
- Canada
- Prior art keywords
- alkylphenol
- tackifying
- octylphenol
- alkyl
- rubber
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 19
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 61
- 229920001971 elastomer Polymers 0.000 claims abstract description 46
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000000806 elastomer Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000007859 condensation product Substances 0.000 claims abstract description 9
- -1 methylol groups Chemical group 0.000 claims abstract description 6
- 239000012783 reinforcing fiber Substances 0.000 claims abstract description 6
- 239000000047 product Substances 0.000 claims abstract description 4
- 239000005060 rubber Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 9
- 150000003335 secondary amines Chemical class 0.000 claims description 9
- 230000014759 maintenance of location Effects 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 229920003052 natural elastomer Polymers 0.000 claims description 6
- 229920001194 natural rubber Polymers 0.000 claims description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 5
- 229920001568 phenolic resin Polymers 0.000 claims description 5
- 238000004073 vulcanization Methods 0.000 claims description 5
- 229910000831 Steel Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000006229 carbon black Substances 0.000 claims description 3
- 239000010959 steel Substances 0.000 claims description 3
- 229920003051 synthetic elastomer Polymers 0.000 claims description 3
- 239000005061 synthetic rubber Substances 0.000 claims description 3
- 229910001369 Brass Inorganic materials 0.000 claims description 2
- 239000010951 brass Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000004636 vulcanized rubber Substances 0.000 claims description 2
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 claims 8
- 229910052739 hydrogen Chemical group 0.000 claims 4
- 239000001257 hydrogen Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000004606 Fillers/Extenders Substances 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 150000008430 aromatic amides Chemical class 0.000 claims 1
- 229940043237 diethanolamine Drugs 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- SEBNPZMOBUCYCA-UHFFFAOYSA-N morpholin-4-ylmethanol Chemical compound OCN1CCOCC1 SEBNPZMOBUCYCA-UHFFFAOYSA-N 0.000 claims 1
- 230000003014 reinforcing effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229960004279 formaldehyde Drugs 0.000 description 20
- 235000019256 formaldehyde Nutrition 0.000 description 15
- 235000013824 polyphenols Nutrition 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000306 component Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 244000043261 Hevea brasiliensis Species 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 229960003742 phenol Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000013032 Hydrocarbon resin Substances 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229920006270 hydrocarbon resin Polymers 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000007281 aminoalkylation reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000003490 calendering Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920013730 reactive polymer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 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 description 2
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
- UHBUPDFDZHLGCC-UHFFFAOYSA-N 2-[7-(2-hydroxyphenyl)heptyl]propane-1,3-diol Chemical compound OCC(CO)CCCCCCCC1=CC=CC=C1O UHBUPDFDZHLGCC-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RQKIKLZYXDAGRZ-UHFFFAOYSA-N CC(C)=C.CC(C)=C.CCCCCCCCC1=CC=CC=C1O Chemical compound CC(C)=C.CC(C)=C.CCCCCCCCC1=CC=CC=C1O RQKIKLZYXDAGRZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- BXPKUWCGNFTTBX-UHFFFAOYSA-N OC1C=CC=CC1=CN1CCOCC1 Chemical class OC1C=CC=CC1=CN1CCOCC1 BXPKUWCGNFTTBX-UHFFFAOYSA-N 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229940113083 morpholine Drugs 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005120 petroleum cracking Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Reinforced Plastic Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66943476A | 1976-03-22 | 1976-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1076727A true CA1076727A (en) | 1980-04-29 |
Family
ID=24686313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA263,965A Expired CA1076727A (en) | 1976-03-22 | 1976-10-22 | Modified phenolic tackifier |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US4146512A (enExample) |
| JP (1) | JPS52114641A (enExample) |
| AU (1) | AU498486B2 (enExample) |
| BR (1) | BR7607812A (enExample) |
| CA (1) | CA1076727A (enExample) |
| DE (1) | DE2652727C3 (enExample) |
| ES (3) | ES457099A1 (enExample) |
| FR (1) | FR2345481A1 (enExample) |
| GB (1) | GB1532115A (enExample) |
| IT (1) | IT1070930B (enExample) |
| MX (1) | MX145316A (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2651172C2 (de) * | 1976-11-10 | 1982-11-18 | Basf Ag, 6700 Ludwigshafen | Als Klebrigmacher für Kautschuk verwendete Aldehyd-Kondensate |
| US4359502A (en) * | 1978-10-23 | 1982-11-16 | Raychem Corporation | Method for joining heat-recoverable sheet material and resulting article |
| ZA84192B (en) * | 1983-05-12 | 1984-08-29 | Firestone Tire & Rubber Co | Rubber compositions and articles thereof having improved metal adhesion and metal adhesion retention |
| US4435477A (en) | 1983-07-25 | 1984-03-06 | The Firestone Tire & Rubber Company | Rubber compositions and articles thereof having improved metal adhesion and metal adhesion retention |
| JPS60139729A (ja) * | 1983-12-27 | 1985-07-24 | Ube Ind Ltd | 強化ゴム組成物の製造法 |
| US5626705A (en) * | 1995-06-07 | 1997-05-06 | Weyerhaeuser Company | Rapid setting adhesive and method of its use |
| JP4502569B2 (ja) * | 2002-07-12 | 2010-07-14 | ダイセル・エボニック株式会社 | ゴム補強構造体 |
| FR2842815B1 (fr) * | 2002-07-25 | 2007-06-22 | Saint Gobain Isover | Solution aqueuse de resine compose phenolique-formaldhehyde- aminoalcool, procede de preparation, composition d'encollage de fibres minerales renfermant ladite resine et produits resultants |
| US20040127652A1 (en) * | 2002-12-27 | 2004-07-01 | Majumdar Ramendra Nath | Rubber composition which contains a tack retention additive and tire with component thereof |
| ATE458764T1 (de) * | 2006-09-05 | 2010-03-15 | Si Group Inc | Modifizierte hydrocarbylphenol-aldehydharze als klebrigmacher und diese enthaltende kautschukzusammensetzungen |
| CN102295621B (zh) * | 2010-07-29 | 2013-12-18 | 武汉径河化工有限公司 | 吗啉改性对叔丁基酚醛树脂及其制备方法 |
| FR2969620B1 (fr) * | 2010-12-23 | 2013-01-11 | Total Raffinage Marketing | Resines alkylphenol-aldehyde modifiees, leur utilisation comme additifs ameliorant les proprietes a froid de carburants et combustibles hydrocarbones liquides |
| WO2014040300A1 (zh) | 2012-09-17 | 2014-03-20 | 华奇（张家港）化工有限公司 | 烷基酚醛树脂及其制备方法 |
| CN103172814A (zh) * | 2013-04-10 | 2013-06-26 | 徐川大 | 一种共聚缩合树脂的制备方法 |
| US9932436B2 (en) | 2013-10-17 | 2018-04-03 | Si Group, Inc. | Modified alkylphenol-aldehyde resins stabilized by a salicylic acid |
| WO2015057879A1 (en) | 2013-10-17 | 2015-04-23 | Si Group, Inc. | In-situ alkylphenol-aldehyde resins |
| EP3283543A4 (en) * | 2015-04-15 | 2018-12-12 | Agency For Science, Technology And Research | Modified porous hypercrosslinked polymers for co2 capture and conversion |
| CN107686544B (zh) * | 2016-08-04 | 2020-01-21 | 彤程化学（中国）有限公司 | 一种有机碱催化合成烷基酚甲醛硫化树脂的方法 |
| US12331165B2 (en) * | 2018-03-06 | 2025-06-17 | Bakelite UK Holding Ltd. | Catalyst system for curing phenolic resole resins |
| CN109575205B (zh) * | 2018-11-20 | 2021-06-15 | 山东阳谷华泰化工股份有限公司 | 一种4-叔烷基苯酚-（吗啉基）甲醛树脂及其制备方法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2649432A (en) * | 1951-03-05 | 1953-08-18 | Us Rubber Co | Vulcanization with alkyl dimethylolphenol and alknaolamine |
| US3001999A (en) * | 1955-12-01 | 1961-09-26 | Geschickter Fund Med Res | Products of phenol derivatives with formaldehyde and amines |
| US2997455A (en) * | 1956-11-09 | 1961-08-22 | Huels Chemische Werke Ag | Process of stabilizing polyolefins, and product |
| US3173952A (en) * | 1959-12-24 | 1965-03-16 | Monsanto Co | Tris-(3, 5-dialkyl-4-hydroxybenzyl) amines |
| US3462382A (en) * | 1966-07-15 | 1969-08-19 | Koppers Co Inc | Tris - substituted resorcinol compound and the modification of rubber therewith |
| US3962156A (en) * | 1974-07-15 | 1976-06-08 | Rohm And Haas Company | Tackifier for rubber |
-
1976
- 1976-10-22 CA CA263,965A patent/CA1076727A/en not_active Expired
- 1976-10-29 IT IT28925/76A patent/IT1070930B/it active
- 1976-11-10 JP JP13427676A patent/JPS52114641A/ja active Granted
- 1976-11-18 MX MX167076A patent/MX145316A/es unknown
- 1976-11-19 DE DE2652727A patent/DE2652727C3/de not_active Expired
- 1976-11-22 AU AU19867/76A patent/AU498486B2/en not_active Expired
- 1976-11-22 BR BR7607812A patent/BR7607812A/pt unknown
-
1977
- 1977-03-21 GB GB11912/77A patent/GB1532115A/en not_active Expired
- 1977-03-22 ES ES457099A patent/ES457099A1/es not_active Expired
- 1977-03-22 FR FR7708550A patent/FR2345481A1/fr active Granted
- 1977-03-22 ES ES457098A patent/ES457098A1/es not_active Expired
- 1977-03-22 ES ES457100A patent/ES457100A1/es not_active Expired
- 1977-08-29 US US05/828,573 patent/US4146512A/en not_active Expired - Lifetime
- 1977-10-13 US US05/841,624 patent/US4146513A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2652727B2 (de) | 1979-02-15 |
| US4146513A (en) | 1979-03-27 |
| ES457100A1 (es) | 1978-03-01 |
| FR2345481A1 (fr) | 1977-10-21 |
| US4146512A (en) | 1979-03-27 |
| AU1986776A (en) | 1978-06-01 |
| AU498486B2 (en) | 1979-03-15 |
| FR2345481B1 (enExample) | 1979-03-23 |
| ES457099A1 (es) | 1978-03-01 |
| IT1070930B (it) | 1985-04-02 |
| GB1532115A (en) | 1978-11-15 |
| JPS5515496B2 (enExample) | 1980-04-24 |
| ES457098A1 (es) | 1978-03-01 |
| DE2652727C3 (de) | 1979-10-18 |
| MX145316A (es) | 1982-01-27 |
| DE2652727A1 (de) | 1977-09-29 |
| BR7607812A (pt) | 1977-10-11 |
| JPS52114641A (en) | 1977-09-26 |
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