CA1076289A - Methode de preparation de resines de phenylamine - Google Patents

Methode de preparation de resines de phenylamine

Info

Publication number: CA1076289A
Authority: CA; Canada
Prior art keywords: phenol; carbon atoms; alkyl radical; resin; resins
Prior art date: 1974-12-09
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

Application number

CA236,136A

Other languages

English (en)

Other versions

CA236136S (en

Inventor

Vladimir V. Moiseev

Alexandr N. Polukhin

Tamara I. Esina

Galina P. Kolesnikova

Vladimir V. Kosovtsev

Viktor A. Zimnukhov

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1974-12-09

Filing date

1975-09-23

Publication date

1980-04-22

1975-09-23 Application filed by Individual filed Critical Individual

1980-04-22 Application granted granted Critical

1980-04-22 Publication of CA1076289A publication Critical patent/CA1076289A/fr

Status Expired legal-status Critical Current

Links

229920005989 resin Polymers 0.000 title claims abstract description 72
239000011347 resin Substances 0.000 title claims abstract description 72
238000000034 method Methods 0.000 title claims description 10
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 51
239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 25
235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 25
229960004011 methenamine Drugs 0.000 claims abstract description 25
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 24
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 12
150000002989 phenols Chemical class 0.000 claims abstract description 12
239000000047 product Substances 0.000 claims abstract description 12
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 abstract description 10
-1 alkyl radical Chemical class 0.000 claims abstract description 9
239000007859 condensation product Substances 0.000 claims abstract description 9
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 7
239000000203 mixture Substances 0.000 claims description 23
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 17
238000009833 condensation Methods 0.000 claims description 11
230000005494 condensation Effects 0.000 claims description 11
229960004889 salicylic acid Drugs 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
150000005165 hydroxybenzoic acids Chemical class 0.000 claims description 2
239000012634 fragment Substances 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
229920001971 elastomer Polymers 0.000 abstract description 20
239000005060 rubber Substances 0.000 abstract description 20
238000006482 condensation reaction Methods 0.000 abstract description 3
239000003381 stabilizer Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
229910021529 ammonia Inorganic materials 0.000 description 8
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical class C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 7
KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
229910052573 porcelain Inorganic materials 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
230000000717 retained effect Effects 0.000 description 6
239000003963 antioxidant agent Substances 0.000 description 5
230000003078 antioxidant effect Effects 0.000 description 5
238000005096 rolling process Methods 0.000 description 5
241000698776 Duma Species 0.000 description 4
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
230000032683 aging Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 4
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 4
229920001568 phenolic resin Polymers 0.000 description 4
238000003756 stirring Methods 0.000 description 4
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 3
CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 2
ABMULKFGWTYIIK-UHFFFAOYSA-N 2-hexylphenol Chemical class CCCCCCC1=CC=CC=C1O ABMULKFGWTYIIK-UHFFFAOYSA-N 0.000 description 2
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000010692 aromatic oil Substances 0.000 description 2
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
229930003836 cresol Natural products 0.000 description 2
229940013361 cresol Drugs 0.000 description 2
HASGOCLZFTZSTN-UHFFFAOYSA-N cyclohexane;hexane Chemical compound CCCCCC.C1CCCCC1 HASGOCLZFTZSTN-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229920003986 novolac Polymers 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
230000000930 thermomechanical effect Effects 0.000 description 2
150000003739 xylenols Chemical class 0.000 description 2
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
DMAXMXPDVWTIRV-UHFFFAOYSA-N 2-(2-phenylethyl)phenol Chemical class OC1=CC=CC=C1CCC1=CC=CC=C1 DMAXMXPDVWTIRV-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
241001441571 Hiodontidae Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
QSYBDNNHWODCCJ-UHFFFAOYSA-N buta-1,3-diene;prop-1-en-2-ylbenzene Chemical compound C=CC=C.CC(=C)C1=CC=CC=C1 QSYBDNNHWODCCJ-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000013329 compounding Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000013068 control sample Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000010354 integration Effects 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229950004864 olamine Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
HLCHESOMJVGDSJ-UHFFFAOYSA-N thiq Chemical compound C1=CC(Cl)=CC=C1CC(C(=O)N1CCC(CN2N=CN=C2)(CC1)C1CCCCC1)NC(=O)C1NCC2=CC=CC=C2C1 HLCHESOMJVGDSJ-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000002351 wastewater Substances 0.000 description 1

Classifications

- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- 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
- C08K5/05—Alcohols; Metal alcoholates
- 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
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/06—Copolymers with styrene

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)
Paints Or Removers (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

CA236,136A 1974-12-09 1975-09-23 Methode de preparation de resines de phenylamine Expired CA1076289A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SU2081749A SU550405A1 (ru)	1974-12-09	1974-12-09	Способ получени феноламинных смол

Publications (1)

Publication Number	Publication Date
CA1076289A true CA1076289A (fr)	1980-04-22

Family

ID=20602782

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA236,136A Expired CA1076289A (fr)	1974-12-09	1975-09-23	Methode de preparation de resines de phenylamine

Country Status (7)

Country	Link
JP (1)	JPS5270000A (fr)
CA (1)	CA1076289A (fr)
CS (1)	CS184981B1 (fr)
DE (1)	DE2543649B2 (fr)
FR (1)	FR2294204A1 (fr)
RO (1)	RO71676A (fr)
SU (1)	SU550405A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8841485B2 (en)	2010-07-27	2014-09-23	Sumitomo Bakelite Co., Ltd.	Liquid phenol resin and method of preparing the same
US9657139B2 (en)	2011-01-14	2017-05-23	Sumitomo Bakelite Co., Ltd.	Liquid resol-type phenolic resin

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2224769C2 (ru) *	2002-05-06	2004-02-27	Федеральное государственное унитарное предприятие "Научно-исследовательский институт синтетического каучука им. акад. С.В. Лебедева"	Способ получения стабилизатора и полиизопреновая композиция, его содержащая
EP2694312B1 (fr)	2011-04-04	2015-03-04	Schaeffler Technologies AG & Co. KG	Dispositif pour la transmission d'un couple

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3228899A (en) *	1961-07-10	1966-01-11	Monsanto Co	Phenolic resins from styrene, phenol and a vegetable drying oil
US3321434A (en) *	1966-06-16	1967-05-23	Minnesota Mining & Mfg	Saturation of porous material with solution of phenolic compound and hexamethylenetetramine in solvent containing acetic acid, propionic acid or mixtures thereof
CH579602A5 (fr) *	1972-06-21	1976-09-15	Hoechst Ag

1974
- 1974-12-09 SU SU2081749A patent/SU550405A1/ru active
1975
- 1975-09-23 CA CA236,136A patent/CA1076289A/fr not_active Expired
- 1975-09-30 DE DE2543649A patent/DE2543649B2/de not_active Withdrawn
- 1975-09-30 RO RO7583486A patent/RO71676A/fr unknown
- 1975-10-08 FR FR7530821A patent/FR2294204A1/fr active Granted
- 1975-10-14 CS CS7500006930A patent/CS184981B1/cs unknown
- 1975-12-08 JP JP50145184A patent/JPS5270000A/ja active Pending

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8841485B2 (en)	2010-07-27	2014-09-23	Sumitomo Bakelite Co., Ltd.	Liquid phenol resin and method of preparing the same
US9657139B2 (en)	2011-01-14	2017-05-23	Sumitomo Bakelite Co., Ltd.	Liquid resol-type phenolic resin

Also Published As

Publication number	Publication date
FR2294204B1 (fr)	1981-09-18
SU550405A1 (ru)	1977-03-15
RO71676A (fr)	1982-09-09
FR2294204A1 (fr)	1976-07-09
CS184981B1 (en)	1978-09-15
DE2543649B2 (de)	1981-02-26
JPS5270000A (en)	1977-06-10
DE2543649A1 (de)	1976-06-10

Legal Events

Date	Code	Title	Description
1997-04-22	MKEX	Expiry

Publication	Publication Date	Title
CA1223693A (fr)	1987-06-30	Resines de melamine phenolique pour promouvoir l'adherence entre metaux et caoutchoucs
US5030692A (en)	1991-07-09	Rubber compounding resorcinolic resins and process for making the same
US3576788A (en)	1971-04-27	Polymeric compositions prepared by reacting aralkyl ethers with phenols and curing said compositions with hexamethylenetetramine
CA2110789A1 (fr)	1994-06-18	Produit de co-condensation et composition de caoutchouc renfermant ce produit
US2954360A (en)	1960-09-27	Process for producing oxygen-containing condensation resins from aromatic hydrocarbons and product produced thereby
US2211048A (en)	1940-08-13	Rubberlike products and process of making them
CA1076289A (fr)	1980-04-22	Methode de preparation de resines de phenylamine
CA1156784A (fr)	1983-11-08	Novolaques modifiees au siloxane, leur obtention et leur utilisation pour la fabrication de garnitures de frottement
US4107141A (en)	1978-08-15	Method of preparing phenolamine resins
US2813843A (en)	1957-11-19	Product of and process for the vulcanization of butadiene rubbers
US3817890A (en)	1974-06-18	Adhesive composition and process
US5132349A (en)	1992-07-21	Preparation process of resin composition having phenolic hydroxyl groups
US20210139686A1 (en)	2021-05-13	Resins having a high methylol to dibenzyl ether ratio and methods of making the same
WO2017164293A1 (fr)	2017-09-28	Composition d'agent antivieillissement
US4013605A (en)	1977-03-22	Phenolic resins from alkyl substituted dimethylolphenols
CA1066448A (fr)	1979-11-13	Resines durcissables a teneur de bore pour le renforcement du caoutchouc
JP3190071B2 (ja)	2001-07-16	ポリアリーレンチオエーテル組成物
US2898322A (en)	1959-08-04	Vulcanization of butadiene rubbers with phenol-aldehyde reaction products and product obtained thereby
US3370023A (en)	1968-02-20	Curable composition comprising rubber and the co-condensation product of an aromatic hydrocarbon-aldehyde resin and a terpene phenol
CA1068436A (fr)	1979-12-18	Methode de stabilisation des caoutchoucs et de produits vulcanises
CA2025242A1 (fr)	1991-05-21	Catalyseurs aprotiques polaires et formation de fluorosilicones liquides
US2200715A (en)	1940-05-14	Conversion products of rubber
US3668258A (en)	1972-06-06	Sulfur-containing polyaryl polyphenolic compounds and process
US2634250A (en)	1953-04-07	Composition of matter comprising a butadiene-vinyl-pyriding copolymer and a novolac
US4075166A (en)	1978-02-21	Method of stabilization of rubbers and vulcanizates

CA1076289A - Methode de preparation de resines de phenylamine - Google Patents

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