JPS5928213B2 - 樹脂質縮合物の製法 - Google Patents

樹脂質縮合物の製法

Info

Publication number: JPS5928213B2
Authority: JP; Japan
Prior art keywords: friction; phenol; particles; resin; aldehyde
Prior art date: 1974-11-14
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

JP13572975A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5171393A (ja

Inventor

エーガーデイナーロバート

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.)

3M Co

Original Assignee

Minnesota Mining and Manufacturing Co

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.)

1974-11-14

Filing date

1975-11-13

Publication date

1984-07-11

1975-11-13 Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co

1976-06-21 Publication of JPS5171393A publication Critical patent/JPS5171393A/ja

1984-07-11 Publication of JPS5928213B2 publication Critical patent/JPS5928213B2/ja

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
244000226021 Anacardium occidentale Species 0.000 claims description 8
235000020226 cashew nut Nutrition 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
238000006596 Alder-ene reaction Methods 0.000 claims description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
239000002245 particle Substances 0.000 description 37
150000002989 phenols Chemical class 0.000 description 31
239000000203 mixture Substances 0.000 description 25
229920005989 resin Polymers 0.000 description 24
239000011347 resin Substances 0.000 description 24
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 23
150000001299 aldehydes Chemical class 0.000 description 19
238000012360 testing method Methods 0.000 description 19
239000000047 product Substances 0.000 description 13
229920001568 phenolic resin Polymers 0.000 description 12
239000002253 acid Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000005011 phenolic resin Substances 0.000 description 9
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
238000009472 formulation Methods 0.000 description 8
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 8
239000007788 liquid Substances 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
235000013824 polyphenols Nutrition 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
238000011156 evaluation Methods 0.000 description 5
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
-1 phenolic aldehyde Chemical class 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
239000010425 asbestos Substances 0.000 description 4
238000004132 cross linking Methods 0.000 description 4
239000004312 hexamethylene tetramine Substances 0.000 description 4
235000010299 hexamethylene tetramine Nutrition 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
229920003986 novolac Polymers 0.000 description 4
229910052895 riebeckite Inorganic materials 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000005977 Ethylene Substances 0.000 description 3
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
239000000920 calcium hydroxide Substances 0.000 description 3
229910001861 calcium hydroxide Inorganic materials 0.000 description 3
125000005019 carboxyalkenyl group Chemical group 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
238000010276 construction Methods 0.000 description 3
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000000034 method Methods 0.000 description 3
229920002866 paraformaldehyde Polymers 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
230000004580 weight loss Effects 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
239000002585 base Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
239000000292 calcium oxide Substances 0.000 description 2
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000009826 distribution Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000012535 impurity Substances 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
239000005445 natural material Substances 0.000 description 2
150000008442 polyphenolic compounds Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000000859 sublimation Methods 0.000 description 2
230000008022 sublimation Effects 0.000 description 2
238000010998 test method Methods 0.000 description 2
229920001187 thermosetting polymer Polymers 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
XRFYZEHRLUNWIJ-UHFFFAOYSA-N 3-pentadec-1-enylphenol Chemical compound CCCCCCCCCCCCCC=CC1=CC=CC(O)=C1 XRFYZEHRLUNWIJ-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
238000005698 Diels-Alder reaction Methods 0.000 description 1
241000790917 Dioxys <bee> Species 0.000 description 1
229910006069 SO3H Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
230000004913 activation Effects 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229940023913 cation exchange resins Drugs 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012612 commercial material Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
210000001723 extracellular space Anatomy 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000010954 inorganic particle Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
239000002923 metal particle Substances 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
238000003801 milling Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000003607 modifier Substances 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
238000011417 postcuring Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000009738 saturating Methods 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000012546 transfer Methods 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
- 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
- C08G8/18—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenols substituted by carboxylic or sulfonic acid groups
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D69/00—Friction linings; Attachment thereof; Selection of coacting friction substances or surfaces
- F16D69/02—Composition of linings ; Methods of manufacturing
- F16D69/025—Compositions based on an organic binder

Landscapes

Chemical & Material Sciences (AREA)
General Engineering & Computer Science (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Mechanical Engineering (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Manufacture Of Macromolecular Shaped Articles (AREA)
Braking Arrangements (AREA)
Reinforced Plastic Materials (AREA)
Phenolic Resins Or Amino Resins (AREA)

JP13572975A 1974-11-14 1975-11-13 樹脂質縮合物の製法 Expired JPS5928213B2 (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US52382474A	1974-11-14	1974-11-14

Publications (2)

Publication Number	Publication Date
JPS5171393A JPS5171393A (ja)	1976-06-21
JPS5928213B2 true JPS5928213B2 (ja)	1984-07-11

Family

ID=24086593

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP13572975A Expired JPS5928213B2 (ja)	1974-11-14	1975-11-13	樹脂質縮合物の製法

Country Status (3)

Country	Link
JP (1)	JPS5928213B2 (fr)
CA (1)	CA1055191A (fr)
GB (1)	GB1524689A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4131590A (en) *	1977-08-18	1978-12-26	Raybestos-Manhattan, Inc.	Epoxy-rubber based friction material
JP5797428B2 (ja) *	2010-04-23	2015-10-21	日清紡ブレーキ株式会社	ディスクブレーキパッド

1975
- 1975-10-07 CA CA237,167A patent/CA1055191A/fr not_active Expired
- 1975-10-27 GB GB4418875A patent/GB1524689A/en not_active Expired
- 1975-11-13 JP JP13572975A patent/JPS5928213B2/ja not_active Expired

Also Published As

Publication number	Publication date
JPS5171393A (ja)	1976-06-21
CA1055191A (fr)	1979-05-22
GB1524689A (en)	1978-09-13

Publication	Publication Date	Title
US4268657A (en)	1981-05-19	Friction element containing phenol-formaldehyde-alkylphenol binder
US4026867A (en)	1977-05-31	Acid modified phenol-aldehyde resinous condensation products and friction particles therefrom
US3966670A (en)	1976-06-29	Friction particle for brake lining
CA2012052C (fr)	2000-01-11	Compositions de resines phenoliques
US4831067A (en)	1989-05-16	Process for the manufacture of frictional elements and frictional elements produced thereby
US4395498A (en)	1983-07-26	High temperature phenolic resins and friction elements prepared therefrom
US4316827A (en)	1982-02-23	Rubber modified phenolic friction particles
US4101500A (en)	1978-07-18	Brake lining compositions having friction particles of an aromatic amine modified novolac resin and an aromatic carboxylic compound
JP3138751B2 (ja)	2001-02-26	摩擦要素の為の組成物
JPS5928213B2 (ja)	1984-07-11	樹脂質縮合物の製法
US4420571A (en)	1983-12-13	Phenolic friction particles
US3879338A (en)	1975-04-22	Friction element composition
US3767612A (en)	1973-10-23	Friction element composition
JPH0649159A (ja)	1994-02-22	摩擦材用ノボラック型フェノール樹脂組成物
US3878160A (en)	1975-04-15	Friction element composition
CA1159597A (fr)	1983-12-27	Procede de fabrication des particules de resine phenolique et elements de frottement com poses de ce materiau
EP0038689B1 (fr)	1986-01-08	Elément de friction
JPS61152717A (ja)	1986-07-11	硼酸変性フエノ−ル樹脂組成物
US3850874A (en)	1974-11-26	Friction element composition
US3864304A (en)	1975-02-04	Friction particle for brake lining
JPH0828617A (ja)	1996-02-02	摩擦材用フェノール樹脂組成物
US3781241A (en)	1973-12-25	Friction particle for brake lining
CA1312401C (fr)	1993-01-05	Procede de fabrication d'elements de frottement, et element ainsi fabrique
JPH0881615A (ja)	1996-03-26	レジノイド砥石
JPH0874904A (ja)	1996-03-19	摩擦材用樹脂組成物