GB1061022A - Creación de Inventos y Patentes con Inteligencia Artificial

GB1061022A – Salts of esters of sulpho-carboxylic acids and polymers thereof with acrylonitrile
– Google Patents

GB1061022A – Salts of esters of sulpho-carboxylic acids and polymers thereof with acrylonitrile
– Google Patents
Salts of esters of sulpho-carboxylic acids and polymers thereof with acrylonitrile

Info

Publication number
GB1061022A

GB1061022A
GB42012/63A
GB4201263A
GB1061022A
GB 1061022 A
GB1061022 A
GB 1061022A
GB 42012/63 A
GB42012/63 A
GB 42012/63A
GB 4201263 A
GB4201263 A
GB 4201263A
GB 1061022 A
GB1061022 A
GB 1061022A
Authority
GB
United Kingdom
Prior art keywords
compound
tertiary amine
formula
alkali metal
acrylonitrile
Prior art date
1962-10-24
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
GB42012/63A
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.)

Eastman Kodak Co

Original Assignee
Eastman Kodak 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.)
1962-10-24
Filing date
1963-10-24
Publication date
1967-03-08

1963-10-24
Application filed by Eastman Kodak Co
filed
Critical
Eastman Kodak Co

1967-03-08
Publication of GB1061022A
publication
Critical
patent/GB1061022A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

NLHHRLWOUZZQLW-UHFFFAOYSA-N
Acrylonitrile
Chemical compound

C=CC#N
NLHHRLWOUZZQLW-UHFFFAOYSA-N
0.000
title
abstract
6

229920000642
polymer
Polymers

0.000
title
abstract
6

150000002148
esters
Chemical class

0.000
title
abstract
3

150000003839
salts
Chemical class

0.000
title
abstract
3

DIORMHZUUKOISG-UHFFFAOYSA-N
sulfoformic acid
Chemical class

OC(=O)S(O)(=O)=O
DIORMHZUUKOISG-UHFFFAOYSA-N
0.000
title
1

-1
aliphatic tertiary amine
Chemical class

0.000
abstract
16

150000001875
compounds
Chemical class

0.000
abstract
14

229910052783
alkali metal
Inorganic materials

0.000
abstract
8

150000001340
alkali metals
Chemical group

0.000
abstract
8

125000004432
carbon atom
Chemical group

0.000
abstract
6

125000004435
hydrogen atom
Chemical group

[H]*

0.000
abstract
4

125000000217
alkyl group
Chemical group

0.000
abstract
3

150000001408
amides
Chemical class

0.000
abstract
3

229920001577
copolymer
Polymers

0.000
abstract
3

125000002496
methyl group
Chemical group

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

0.000
abstract
3

239000000203
mixture
Chemical class

0.000
abstract
3

239000000178
monomer
Substances

0.000
abstract
3

150000003512
tertiary amines
Chemical class

0.000
abstract
3

OZAIFHULBGXAKX-UHFFFAOYSA-N
2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile
Chemical class

N#CC(C)(C)N=NC(C)(C)C#N
OZAIFHULBGXAKX-UHFFFAOYSA-N
0.000
abstract
2

JUJWROOIHBZHMG-UHFFFAOYSA-N
Pyridine
Chemical compound

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

KAESVJOAVNADME-UHFFFAOYSA-N
Pyrrole
Chemical compound

C=1C=CNC=1
KAESVJOAVNADME-UHFFFAOYSA-N
0.000
abstract
2

125000001931
aliphatic group
Chemical group

0.000
abstract
2

239000003054
catalyst
Substances

0.000
abstract
2

239000000975
dye
Substances

0.000
abstract
2

SNVLJLYUUXKWOJ-UHFFFAOYSA-N
methylidenecarbene
Chemical group

C=[C]
SNVLJLYUUXKWOJ-UHFFFAOYSA-N
0.000
abstract
2

239000002685
polymerization catalyst
Substances

0.000
abstract
2

238000006116
polymerization reaction
Methods

0.000
abstract
2

229920001897
terpolymer
Polymers

0.000
abstract
2

GETQZCLCWQTVFV-UHFFFAOYSA-N
trimethylamine
Chemical compound

CN(C)C
GETQZCLCWQTVFV-UHFFFAOYSA-N
0.000
abstract
2

229920002554
vinyl polymer
Polymers

0.000
abstract
2

SMZOUWXMTYCWNB-UHFFFAOYSA-N
2-(2-methoxy-5-methylphenyl)ethanamine
Chemical compound

COC1=CC=C(C)C=C1CCN
SMZOUWXMTYCWNB-UHFFFAOYSA-N
0.000
abstract
1

NIXOWILDQLNWCW-UHFFFAOYSA-N
2-Propenoic acid
Natural products

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

FCYVWWWTHPPJII-UHFFFAOYSA-N
2-methylidenepropanedinitrile
Chemical compound

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

NJIRSTSECXKPCO-UHFFFAOYSA-M
3-[n-methyl-4-[2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]anilino]propanenitrile;chloride
Chemical compound

[Cl-].C1=CC(N(CCC#N)C)=CC=C1\C=C\C1=[N+](C)C2=CC=CC=C2C1(C)C
NJIRSTSECXKPCO-UHFFFAOYSA-M
0.000
abstract
1

125000002373
5 membered heterocyclic group
Chemical group

0.000
abstract
1

HRPVXLWXLXDGHG-UHFFFAOYSA-N
Acrylamide
Chemical compound

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

CERQOIWHTDAKMF-UHFFFAOYSA-N
Methacrylic acid
Chemical compound

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

DWAQJAXMDSEUJJ-UHFFFAOYSA-M
Sodium bisulfite
Chemical compound

[Na+].OS([O-])=O
DWAQJAXMDSEUJJ-UHFFFAOYSA-M
0.000
abstract
1

WLKAMFOFXYCYDK-UHFFFAOYSA-N
[5-amino-4-[[3-[(2-amino-4-azaniumyl-5-methylphenyl)diazenyl]-4-methylphenyl]diazenyl]-2-methylphenyl]azanium;dichloride
Chemical compound

[Cl-].[Cl-].CC1=CC=C(N=NC=2C(=CC([NH3+])=C(C)C=2)N)C=C1N=NC1=CC(C)=C([NH3+])C=C1N
WLKAMFOFXYCYDK-UHFFFAOYSA-N
0.000
abstract
1

239000002253
acid
Substances

0.000
abstract
1

150000007513
acids
Chemical class

0.000
abstract
1

150000003926
acrylamides
Chemical class

0.000
abstract
1

230000003213
activating effect
Effects

0.000
abstract
1

125000005907
alkyl ester group
Chemical group

0.000
abstract
1

125000005037
alkyl phenyl group
Chemical group

0.000
abstract
1

KSCQDDRPFHTIRL-UHFFFAOYSA-N
auramine O
Chemical compound

[H+].[Cl-].C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1
KSCQDDRPFHTIRL-UHFFFAOYSA-N
0.000
abstract
1

239000000981
basic dye
Substances

0.000
abstract
1

125000001797
benzyl group
Chemical group

[H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])*

0.000
abstract
1

MMCOUVMKNAHQOY-UHFFFAOYSA-N
carbonoperoxoic acid
Chemical class

OOC(O)=O
MMCOUVMKNAHQOY-UHFFFAOYSA-N
0.000
abstract
1

125000003178
carboxy group
Chemical group

[H]OC(*)=O

0.000
abstract
1

150000001735
carboxylic acids
Chemical class

0.000
abstract
1

239000003153
chemical reaction reagent
Substances

0.000
abstract
1

239000003795
chemical substances by application
Substances

0.000
abstract
1

ZXJXZNDDNMQXFV-UHFFFAOYSA-M
crystal violet
Chemical compound

[Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1
ZXJXZNDDNMQXFV-UHFFFAOYSA-M
0.000
abstract
1

JOXWSDNHLSQKCC-UHFFFAOYSA-N
ethenesulfonamide
Chemical class

NS(=O)(=O)C=C
JOXWSDNHLSQKCC-UHFFFAOYSA-N
0.000
abstract
1

125000005670
ethenylalkyl group
Chemical group

0.000
abstract
1

239000000945
filler
Substances

0.000
abstract
1

125000003187
heptyl group
Chemical group

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

0.000
abstract
1

SYGRIMFNUFCHJC-UHFFFAOYSA-N
hydron;4-methyl-6-phenyldiazenylbenzene-1,3-diamine;chloride
Chemical compound

Cl.C1=C(N)C(C)=CC(N=NC=2C=CC=CC=2)=C1N
SYGRIMFNUFCHJC-UHFFFAOYSA-N
0.000
abstract
1

150000003949
imides
Chemical class

0.000
abstract
1

150000002505
iron
Chemical class

0.000
abstract
1

125000000555
isopropenyl group
Chemical group

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

0.000
abstract
1

239000000314
lubricant
Substances

0.000
abstract
1

150000002825
nitriles
Chemical class

0.000
abstract
1

150000002978
peroxides
Chemical class

0.000
abstract
1

JRKICGRDRMAZLK-UHFFFAOYSA-L
persulfate group
Chemical group

S(=O)(=O)([O-])OOS(=O)(=O)[O-]
JRKICGRDRMAZLK-UHFFFAOYSA-L
0.000
abstract
1

239000000049
pigment
Substances

0.000
abstract
1

239000004014
plasticizer
Substances

0.000
abstract
1

UMJSCPRVCHMLSP-UHFFFAOYSA-N
pyridine
Natural products

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

150000003222
pyridines
Chemical class

0.000
abstract
1

PYWVYCXTNDRMGF-UHFFFAOYSA-N
rhodamine B
Chemical compound

[Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O
PYWVYCXTNDRMGF-UHFFFAOYSA-N
0.000
abstract
1

235000010267
sodium hydrogen sulphite
Nutrition

0.000
abstract
1

239000004289
sodium hydrogen sulphite
Substances

0.000
abstract
1

159000000000
sodium salts
Chemical class

0.000
abstract
1

239000002904
solvent
Substances

0.000
abstract
1

150000003440
styrenes
Chemical class

0.000
abstract
1

LSNNMFCWUKXFEE-UHFFFAOYSA-L
sulfite
Chemical compound

[O-]S([O-])=O
LSNNMFCWUKXFEE-UHFFFAOYSA-L
0.000
abstract
1

BDHFUVZGWQCTTF-UHFFFAOYSA-N
sulfonic acid
Chemical group

OS(=O)=O
BDHFUVZGWQCTTF-UHFFFAOYSA-N
0.000
abstract
1

239000004094
surface-active agent
Substances

0.000
abstract
1

IMFACGCPASFAPR-UHFFFAOYSA-N
tributylamine
Chemical compound

CCCCN(CCCC)CCCC
IMFACGCPASFAPR-UHFFFAOYSA-N
0.000
abstract
1

125000000391
vinyl group
Chemical group

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

0.000
abstract
1

XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
Substances

O
XLYOFNOQVPJJNP-UHFFFAOYSA-N
0.000
abstract
1

Classifications

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

C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof

C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof

C08F220/42—Nitriles

C08F220/44—Acrylonitrile

C08F220/46—Acrylonitrile with carboxylic acids, sulfonic acids or salts thereof

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof

C07C309/01—Sulfonic acids

C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms

C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton

C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton

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

C08F28/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur

Abstract

The invention comprises compounds of the general formula where R represents a hydrogen atom or a methyl group, R1 represents a hydrogen atom or a straight or branched chain alkyl group of from 1 to 7 carbon atoms, and M represents an alkali metal atom or an aliphatic tertiary amine of from 3 to 12 carbon atoms or a heterocyclic tertiary amine, n being zero when M is an alkali metal atom and 1 when M is a tertiary amine. The tertiary amine may be trimethylamine or tributylamine or a 5- or 6-membered heterocyclic tertiary amine e.g. pyrrole or pyridine. They may be prepared by esterifying the carboxylic group of a compound of formula HOOC-CH(R1)-SO3-(H)n-M with a compound of formula CH2 = C(R)-CH2-OH using an alkyl sulphonic acid as a catalyst. Compounds in which M is an alkali metal may also be prepared by esterifying a compound of formula Cl.CH(R1)-COOH with a compound of Formula III to form a compound of the formula Cl.CH(R1)-COOCH2-C(R) = CH2 and then reacting this compound with an alkali metal sulphite to give the compound of Formula I. Examples are given for the preparation of the pyridine salts of allyl sulphoacetate and methallyl sulphoacetate, and of the sodium salt of allyl sulphoacetate. The compounds of Formula I are useful for the preparation of copolymers and terpolymers with acrylonitrile (see Division C3).ALSO:The invention comprises copolymers containing units of acrylonitrile and units of a compound of the general formula CH2=CR-CH2OCOCH(R1)-SO3(H)nM where R represents a hydrogen atom or a methyl group, R1 represents a hydrogen atom or a straight or branched chain alkyl group of from 1 to 7 carbon atoms, and M represents an alkali metal atom or an aliphatic tertiary amine of from 3 to 12 carbon atoms or heterocyclic tertiary amine, n being zero when M is an alkali metal atom and 1 when M is a tertiary amine (see Division C2). The polymer may be a binary copolymer containing from 85 to 96% by weight of units derived from acrylonitrile, or a terpolymer containing from 50 to 93% of units derived from acrylonitrile, from 2 to 20% of units derived from the compound of formula I and from 3 to 48% of units derived from a different compound containing a -CH=C< or CH2=C< group. The preparation of the polymers is accelerated by heat, by actinic light and by polymerization catalysts such as peroxides, persulphates, perborates, the water-soluble salts of percarbonic acid, azo-bis-isobutyronitrile and mixtures of one or more of these catalysts. An activating agent such as sodium bisulphite or an iron salt can be used in conjunction with the polymerization catalysts in aqueous systems. Chain regulators such a alkyl mercaptans can also be added to the polymerization mixtures. The polymerization can be carried out in mass, in solution, or in a non-solvent for the monomers or polymers, e.g. water. In aqueous systems a surfactant can be used in amount not exceeding about 5% of the starting monomers. Suitable copolymerizable monomers containing a -CH=C< or CH2=C< group include styrenes, vinyl and isopropenyl esters of saturated aliphatic or aromatic carboxylic acids containing from 2 to 17 carbon atoms, vinyl alkyl ethers and vinyl alkyl ketones wherein the alkyl group contains from 1 to 4 carbon atoms, vinyl sulphonamides, vinyl halides, vinylidene halides, vinylidene cyanide, acrylic acid and its derivatives, e.g. acrylamide, N-alkyl acrylamides or N,N-dialkyl acrylamides, alkyl esters, benzyl and phenyl esters and methacrylic acid and its corresponding amides and nitriles and esters; and monomeric amides, amides, imides and esters of bicyclo-[2,2,1]-5-heptene carboxylic acids. The polymers can be readily converted from the salt forms to the free acids which can then be further converted to derivatives thereof by treatment with reagents capable of reacting with free sulphonic acid groups. The interpolymers of the invention can be used for forming fibres and can also be formed into flexible sheets from their solutions or doses. Such solutions may have incorporated therein suitable fillers, dyes, pigments, lubricants or plasticizers.ALSO:Basic dyes are used to colour interpolymer compositions or fibres derived from polymers comprising units derived from acrylonitrile and units derived from a compound of the formula:- wherein R represents H or CH3, R1 represents H or a straight or branched chain C1 to C7 alkyl group, and M represents an alkali metal atom or an C3-C12 aliphatic tertiary amine or a heterocyclic tertiary amine, n being zero when M is an alkali metal atom and 1 when M is an aliphatic or heterocyclic tertiary amine (see Divisions C2 and C3 for preparation). Specified dyes are Sevron Blue B, Sevron Brilliant Red 4G, Sevron Green B, Sevron Yellow L, Auramine SP, Calcozine Orange Rs, Rhodamine 5G, Bismarck Brown and Methyl Violet.

GB42012/63A
1962-10-24
1963-10-24
Salts of esters of sulpho-carboxylic acids and polymers thereof with acrylonitrile

Expired

GB1061022A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US232900A

US3260707A
(en)

1962-10-24
1962-10-24
Allyl and methallyl esters of sulfoaliphatic acids, and interpolymers thereof with acrylonitrile

Publications (1)

Publication Number
Publication Date

GB1061022A
true

GB1061022A
(en)

1967-03-08

Family
ID=22875055
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB42012/63A
Expired

GB1061022A
(en)

1962-10-24
1963-10-24
Salts of esters of sulpho-carboxylic acids and polymers thereof with acrylonitrile

Country Status (2)

Country
Link

US
(1)

US3260707A
(en)

GB
(1)

GB1061022A
(en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

DE1595590A1
(en)

1966-02-02
1970-05-21
Bayer Ag

Process for the production of acrylonitrile copolymers

DE1595589A1
(en)

1966-02-02
1970-04-30
Bayer Ag

Process for the production of acrylonitrile copolymers

US3475364A
(en)

1966-10-17
1969-10-28
Celanese Corp
Art of producing dyeable acrylonitrile copolymer compositions and articles

US3666722A
(en)

1971-03-25
1972-05-30
Bayer Ag
Acrylonitrile copolymers containing sulfonic acid groups

US4136078A
(en)

1971-05-21
1979-01-23
The Lubrizol Corporation
Compositions comprising a plasticizer and an n-sulfohydrocarbon-substituted acrylamide polymer

US3923755A
(en)

1972-03-01
1975-12-02
Firestone Tire & Rubber Co
Amine sulfonates as dye sites in suspension polymers

CS170387B1
(en)

1973-08-15
1976-08-27

US4698413A
(en)

1979-08-01
1987-10-06
E. I. Du Pont De Nemours And Company
Acrylic fiber suitable for preparing carbon or graphite fibers

US4336022A
(en)

1979-08-01
1982-06-22
E. I. Du Pont De Nemours And Company
Acrylic precursor fibers suitable for preparing carbon or graphite fibers

US5273750A
(en)

1988-05-02
1993-12-28
Institute National De La Sante Et De La Recherche Medicale- Inserm
Uncrosslinked hydrogel, process for its preparation and its uses as an article for medical and/or surgical purposes such as tubes, films, joints, implants and the like, particularly in ophthalmology

DE102006055397B3
(en)

2006-11-22
2008-05-15
Heraeus Quarzglas Gmbh & Co. Kg

Method and device for the production of a cylindrical profile element made of quartz glass and use thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US2496275A
(en)

1945-08-17
1950-02-07
Eastman Kodak Co
Polymers and copolymers of unsaturated amides

BE523059A
(en)

1950-10-27
1953-10-15

1962

1962-10-24
US
US232900A
patent/US3260707A/en
not_active
Expired – Lifetime

1963

1963-10-24
GB
GB42012/63A
patent/GB1061022A/en
not_active
Expired

Also Published As

Publication number
Publication date

US3260707A
(en)

1966-07-12

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