GB1331558A

GB1331558A – Method of forming a heat resistant film
– Google Patents

GB1331558A – Method of forming a heat resistant film
– Google Patents
Method of forming a heat resistant film

Info

Publication number
GB1331558A

GB1331558A
GB3822971A
GB3822971A
GB1331558A
GB 1331558 A
GB1331558 A
GB 1331558A
GB 3822971 A
GB3822971 A
GB 3822971A
GB 3822971 A
GB3822971 A
GB 3822971A
GB 1331558 A
GB1331558 A
GB 1331558A
Authority
GB
United Kingdom
Prior art keywords
vinyl
xylylene
bis
methyl
acrylamide
Prior art date
1970-08-17
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
GB3822971A
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.)

Toyota Motor Corp

Original Assignee
Toyota Motor Corp
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.)
1970-08-17
Filing date
1971-08-13
Publication date
1973-09-26

1971-08-13
Application filed by Toyota Motor Corp
filed
Critical
Toyota Motor Corp

1973-09-26
Publication of GB1331558A
publication
Critical
patent/GB1331558A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

WEVYAHXRMPXWCK-UHFFFAOYSA-N
Acetonitrile
Chemical compound

CC#N
WEVYAHXRMPXWCK-UHFFFAOYSA-N
0.000
abstract
3

ZMXDDKWLCZADIW-UHFFFAOYSA-N
N,N-Dimethylformamide
Chemical compound

CN(C)C=O
ZMXDDKWLCZADIW-UHFFFAOYSA-N
0.000
abstract
3

238000000576
coating method
Methods

0.000
abstract
3

239000000178
monomer
Substances

0.000
abstract
3

MYRTYDVEIRVNKP-UHFFFAOYSA-N
1,2-Divinylbenzene
Chemical compound

C=CC1=CC=CC=C1C=C
MYRTYDVEIRVNKP-UHFFFAOYSA-N
0.000
abstract
2

HGINCPLSRVDWNT-UHFFFAOYSA-N
Acrolein
Chemical compound

C=CC=O
HGINCPLSRVDWNT-UHFFFAOYSA-N
0.000
abstract
2

KAKZBPTYRLMSJV-UHFFFAOYSA-N
Butadiene
Chemical compound

C=CC=C
KAKZBPTYRLMSJV-UHFFFAOYSA-N
0.000
abstract
2

ZHNUHDYFZUAESO-UHFFFAOYSA-N
Formamide
Chemical compound

NC=O
ZHNUHDYFZUAESO-UHFFFAOYSA-N
0.000
abstract
2

XEEYBQQBJWHFJM-UHFFFAOYSA-N
Iron
Chemical compound

[Fe]
XEEYBQQBJWHFJM-UHFFFAOYSA-N
0.000
abstract
2

JUJWROOIHBZHMG-UHFFFAOYSA-N
Pyridine
Chemical compound

C1=CC=NC=C1
JUJWROOIHBZHMG-UHFFFAOYSA-N
0.000
abstract
2

PPBRXRYQALVLMV-UHFFFAOYSA-N
Styrene
Chemical compound

C=CC1=CC=CC=C1
PPBRXRYQALVLMV-UHFFFAOYSA-N
0.000
abstract
2

FUSUHKVFWTUUBE-UHFFFAOYSA-N
buten-2-one
Chemical compound

CC(=O)C=C
FUSUHKVFWTUUBE-UHFFFAOYSA-N
0.000
abstract
2

239000011248
coating agent
Substances

0.000
abstract
2

239000003792
electrolyte
Substances

0.000
abstract
2

LQNUZADURLCDLV-UHFFFAOYSA-N
nitrobenzene
Chemical compound

[O-][N+](=O)C1=CC=CC=C1
LQNUZADURLCDLV-UHFFFAOYSA-N
0.000
abstract
2

BASFCYQUMIYNBI-UHFFFAOYSA-N
platinum
Chemical compound

[Pt]
BASFCYQUMIYNBI-UHFFFAOYSA-N
0.000
abstract
2

239000003495
polar organic solvent
Substances

0.000
abstract
2

125000000391
vinyl group
Chemical group

[H]C([*])=C([H])[H]

0.000
abstract
2

229920002554
vinyl polymer
Polymers

0.000
abstract
2

125000006839
xylylene group
Chemical group

0.000
abstract
2

UZKWTJUDCOPSNM-UHFFFAOYSA-N
1-ethenoxybutane
Chemical compound

CCCCOC=C
UZKWTJUDCOPSNM-UHFFFAOYSA-N
0.000
abstract
1

PAWQVTBBRAZDMG-UHFFFAOYSA-N
2-(3-bromo-2-fluorophenyl)acetic acid
Chemical compound

OC(=O)CC1=CC=CC(Br)=C1F
PAWQVTBBRAZDMG-UHFFFAOYSA-N
0.000
abstract
1

DBCAQXHNJOFNGC-UHFFFAOYSA-N
4-bromo-1,1,1-trifluorobutane
Chemical compound

FC(F)(F)CCCBr
DBCAQXHNJOFNGC-UHFFFAOYSA-N
0.000
abstract
1

HRPVXLWXLXDGHG-UHFFFAOYSA-N
Acrylamide
Chemical compound

NC(=O)C=C
HRPVXLWXLXDGHG-UHFFFAOYSA-N
0.000
abstract
1

NLHHRLWOUZZQLW-UHFFFAOYSA-N
Acrylonitrile
Chemical compound

C=CC#N
NLHHRLWOUZZQLW-UHFFFAOYSA-N
0.000
abstract
1

CPELXLSAUQHCOX-UHFFFAOYSA-M
Bromide
Chemical compound

[Br-]
CPELXLSAUQHCOX-UHFFFAOYSA-M
0.000
abstract
1

RYGMFSIKBFXOCR-UHFFFAOYSA-N
Copper
Chemical compound

[Cu]
RYGMFSIKBFXOCR-UHFFFAOYSA-N
0.000
abstract
1

IAZDPXIOMUYVGZ-UHFFFAOYSA-N
Dimethylsulphoxide
Chemical compound

CS(C)=O
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
0.000
abstract
1

CERQOIWHTDAKMF-UHFFFAOYSA-M
Methacrylate
Chemical compound

CC(=C)C([O-])=O
CERQOIWHTDAKMF-UHFFFAOYSA-M
0.000
abstract
1

VVQNEPGJFQJSBK-UHFFFAOYSA-N
Methyl methacrylate
Chemical compound

COC(=O)C(C)=C
VVQNEPGJFQJSBK-UHFFFAOYSA-N
0.000
abstract
1

GYCMBHHDWRMZGG-UHFFFAOYSA-N
Methylacrylonitrile
Chemical compound

CC(=C)C#N
GYCMBHHDWRMZGG-UHFFFAOYSA-N
0.000
abstract
1

FXHOOIRPVKKKFG-UHFFFAOYSA-N
N,N-Dimethylacetamide
Chemical compound

CN(C)C(C)=O
FXHOOIRPVKKKFG-UHFFFAOYSA-N
0.000
abstract
1

XTXRWKRVRITETP-UHFFFAOYSA-N
Vinyl acetate
Chemical compound

CC(=O)OC=C
XTXRWKRVRITETP-UHFFFAOYSA-N
0.000
abstract
1

XYLMUPLGERFSHI-UHFFFAOYSA-N
alpha-Methylstyrene
Chemical compound

CC(=C)C1=CC=CC=C1
XYLMUPLGERFSHI-UHFFFAOYSA-N
0.000
abstract
1

239000004411
aluminium
Substances

0.000
abstract
1

XAGFODPZIPBFFR-UHFFFAOYSA-N
aluminium
Chemical compound

[Al]
XAGFODPZIPBFFR-UHFFFAOYSA-N
0.000
abstract
1

229910052782
aluminium
Inorganic materials

0.000
abstract
1

229910052802
copper
Inorganic materials

0.000
abstract
1

239000010949
copper
Substances

0.000
abstract
1

229960001760
dimethyl sulfoxide
Drugs

0.000
abstract
1

AFOSIXZFDONLBT-UHFFFAOYSA-N
divinyl sulfone
Chemical compound

C=CS(=O)(=O)C=C
AFOSIXZFDONLBT-UHFFFAOYSA-N
0.000
abstract
1

238000005868
electrolysis reaction
Methods

0.000
abstract
1

STVZJERGLQHEKB-UHFFFAOYSA-N
ethylene glycol dimethacrylate
Substances

CC(=C)C(=O)OCCOC(=O)C(C)=C
STVZJERGLQHEKB-UHFFFAOYSA-N
0.000
abstract
1

229910052742
iron
Inorganic materials

0.000
abstract
1

229910052757
nitrogen
Inorganic materials

0.000
abstract
1

239000012299
nitrogen atmosphere
Substances

0.000
abstract
1

RPQRDASANLAFCM-UHFFFAOYSA-N
oxiran-2-ylmethyl prop-2-enoate
Chemical compound

C=CC(=O)OCC1CO1
RPQRDASANLAFCM-UHFFFAOYSA-N
0.000
abstract
1

229910052697
platinum
Inorganic materials

0.000
abstract
1

229920000642
polymer
Polymers

0.000
abstract
1

238000006116
polymerization reaction
Methods

0.000
abstract
1

HJWLCRVIBGQPNF-UHFFFAOYSA-N
prop-2-enylbenzene
Chemical compound

C=CCC1=CC=CC=C1
HJWLCRVIBGQPNF-UHFFFAOYSA-N
0.000
abstract
1

UMJSCPRVCHMLSP-UHFFFAOYSA-N
pyridine
Natural products

COC1=CC=CN=C1
UMJSCPRVCHMLSP-UHFFFAOYSA-N
0.000
abstract
1

150000003839
salts
Chemical class

0.000
abstract
1

YSXXGOKILPYXSH-UHFFFAOYSA-O
trimethylazanium;nitrate
Chemical compound

C[NH+](C)C.[O-][N+]([O-])=O
YSXXGOKILPYXSH-UHFFFAOYSA-O
0.000
abstract
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

C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule

C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes

C—CHEMISTRY; METALLURGY

C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON

C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

C08F2/00—Processes of polymerisation

C08F2/46—Polymerisation initiated by wave energy or particle radiation

C08F2/52—Polymerisation initiated by wave energy or particle radiation by electric discharge, e.g. voltolisation

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

C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule

C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes

C08G61/025—Polyxylylenes

C—CHEMISTRY; METALLURGY

C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR

C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR

C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes

C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications

C09D5/4407—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained by polymerisation reactions involving only carbon-to-carbon unsaturated bonds

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

C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule

C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain

C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain

C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms

C08G2261/3424—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms non-conjugated, e.g. paracyclophanes or xylenes

Abstract

1331558 Electrolytic polymerization/coating TOYOTA JIDOSHA KOGYO KK 13 Aug 1971 [17 Aug 1970] 38229/71 Heading C3P [Also in Division C7] Heat-resistant polymer coatings are formed on, for example metallic objects, by electrolyzing a solution of a vinyl monomer and an α,α1-pxylene derivative salt in a polar organic solvent, using the object to be coated as one of the electrodes, thereby causing the monomers to copolymerize and form the desired coating. Vinyl monomers disclosed are styrene, α-methyl styrene, methyl methacrylate, acrylonitrile, methacrylonitrile, glycidyl acrylate and methacrylate, acrylamide, acrolein, methyl vinyl ketone, n-butyl vinyl ether, vinyl acetate, vinyl toluene, N,N1-methylene-bis-acrylamide, divinyl sulfone, divinylbenzene, ethylene glycol dimethacrylate, and butadiene. Para xylylene derivative salts specified are p-xylylene-bis trimethyl ammonium nitrate, (i.e. NO 3 -(CH 3 ) 3 – #N–-CH 2 -C 6 H 4 -CH 2 -#N–(CH 3 ) 3 NO 3 –), pxylylene-bis-triphenyl phosphonium chloride or bromide, and 2,3,5,6-tetrachloro-p-xylylene-bistrimethyl ammonium nitrate. Polar organic solvents specified are dimethyl sulphoxide, dimethylformamide, acetonitrile, pyridine, formamide, dimethylacetamide and nitrobenzene. The para xylylene salt acts both as comonomer and electrolyte. The preferred current density used in the D.C. electrolysis is 2-40 mA/cm2. In the examples, cathodes of aluminium, iron, and copper are coated in a nitrogen atmosphere at 25 C. using platinum anodes, the components of the electrolyte used being selected from those specified above.

GB3822971A
1970-08-17
1971-08-13
Method of forming a heat resistant film

Expired

GB1331558A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

JP45071602A

JPS4924968B1
(en)

1970-08-17
1970-08-17

Publications (1)

Publication Number
Publication Date

GB1331558A
true

GB1331558A
(en)

1973-09-26

Family
ID=13465355
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB3822971A
Expired

GB1331558A
(en)

1970-08-17
1971-08-13
Method of forming a heat resistant film

Country Status (5)

Country
Link

US
(1)

US3720589A
(en)

JP
(1)

JPS4924968B1
(en)

CA
(1)

CA949015A
(en)

DE
(1)

DE2140848C3
(en)

GB
(1)

GB1331558A
(en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4017404A
(en)

*

1976-03-11
1977-04-12
The United States Of America As Represented By The Secretary Of The Department Of Health, Education And Welfare
Apparatus for low temperature ashing using radio frequency excited gas plasma

JPS5452077U
(en)

*

1977-09-19
1979-04-11

US4180442A
(en)

*

1978-06-14
1979-12-25
Mcdonnell Douglas Corporation
Electrodeposition of coatings on metals to enhance adhesive bonding

JPS55152596U
(en)

*

1979-04-17
1980-11-04

CA1258313A
(en)

*

1983-09-26
1989-08-08
Branimir Simic-Glavaski
Molecular electro-optical transistor and switch

AU2002228957A1
(en)

2000-12-11
2002-06-24
Branimir Simic-Glavaski
Molecular electro-optical switching or memory device, and method of making the same

Family Cites Families (4)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3175964A
(en)

*

1960-01-23
1965-03-30
Yawata Iron & Steel Co
Surface treatment of metal article by water-soluble (film-forming) material

US3546016A
(en)

*

1965-06-15
1970-12-08
Gulf Oil Corp
Method of coating a metal article with polymeric material

DE2024695A1
(en)

*

1969-06-11
1970-12-17
Reichold-Albert-Chemie Ag, 2000 Hamburg

Process for the production of water-thinnable, vinyl-modified synthetic resins based on polyether esters

BE759022A
(en)

*

1969-11-17
1971-04-30
Reichhold Albert Chemie Ag

PROCESS FOR THE PREPARATION OF BINDERS FOR AQUEOUS COATING MASSES

1970

1970-08-17
JP
JP45071602A
patent/JPS4924968B1/ja
active
Pending

1971

1971-08-06
US
US00169721A
patent/US3720589A/en
not_active
Expired – Lifetime

1971-08-13
GB
GB3822971A
patent/GB1331558A/en
not_active
Expired

1971-08-14
DE
DE2140848A
patent/DE2140848C3/en
not_active
Expired

1971-08-16
CA
CA120,646A
patent/CA949015A/en
not_active
Expired

Also Published As

Publication number
Publication date

US3720589A
(en)

1973-03-13

DE2140848B2
(en)

1973-07-12

DE2140848A1
(en)

1972-02-24

DE2140848C3
(en)

1974-02-07

JPS4924968B1
(en)

1974-06-26

CA949015A
(en)

1974-06-11

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Legal Events

Date
Code
Title
Description

1974-02-06
PS
Patent sealed [section 19, patents act 1949]

1990-04-11
PCNP
Patent ceased through non-payment of renewal fee

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