GB1017697A

GB1017697A – New phosphite esters
– Google Patents

GB1017697A – New phosphite esters
– Google Patents
New phosphite esters

Info

Publication number
GB1017697A

GB1017697A
GB35151/62A
GB3515162A
GB1017697A
GB 1017697 A
GB1017697 A
GB 1017697A
GB 35151/62 A
GB35151/62 A
GB 35151/62A
GB 3515162 A
GB3515162 A
GB 3515162A
GB 1017697 A
GB1017697 A
GB 1017697A
Authority
GB
United Kingdom
Prior art keywords
formula
group
alkyl
aralkyl
alkaryl
Prior art date
1961-09-14
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
GB35151/62A
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.)

ADVANCE PROD GmbH

Deutsche Advance Produktion GmbH

Original Assignee
ADVANCE PROD GmbH
Deutsche Advance Produktion GmbH
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.)
1961-09-14
Filing date
1962-09-14
Publication date
1966-01-19

1962-09-14
Application filed by ADVANCE PROD GmbH, Deutsche Advance Produktion GmbH
filed
Critical
ADVANCE PROD GmbH

1966-01-19
Publication of GB1017697A
publication
Critical
patent/GB1017697A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

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

C08K5/49—Phosphorus-containing compounds

C08K5/51—Phosphorus bound to oxygen

C08K5/52—Phosphorus bound to oxygen only

C08K5/529—Esters containing heterocyclic rings not representing cyclic esters of phosphoric or phosphorous acids

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System

C07F9/02—Phosphorus compounds

C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom

C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms

C07F9/6551—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System

C07F9/02—Phosphorus compounds

C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom

C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System

C07F9/02—Phosphorus compounds

C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom

C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms

C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms

C07F9/6574—Esters of oxyacids of phosphorus

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

C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen

C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes

C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds

C08G12/043—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with at least two compounds covered by more than one of the groups C08G12/06 – C08G12/24

C08G12/046—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with at least two compounds covered by more than one of the groups C08G12/06 – C08G12/24 one being urea or thiourea

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

C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen

C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes

C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds

C08G12/34—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds and acyclic or carbocyclic compounds

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

C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen

C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes

C08G12/40—Chemically modified polycondensates

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

C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule

C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring

C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only

C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring

C08G65/16—Cyclic ethers having four or more ring atoms

C08G65/18—Oxetanes

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

C08K5/49—Phosphorus-containing compounds

C08K5/51—Phosphorus bound to oxygen

C08K5/52—Phosphorus bound to oxygen only

Abstract

A halogen-containing synthetic resin is stabilized by incorporating therewith a phosphite ester of the formulae: or wherein n is 0 or 1, R1 is an aryl, aralkyl or alkaryl group or an alkyl group which may be substituted with a halogen atom, a cyano group or a group -OR in which R is alkyl, alkenyl, aryl, alkaryl, aralkyl, acyl or abietyl group and R2, R3 and R4 which may be the same or different are groups of the formula:- or alkyl, cycloalkyl, alkaryl, aralkyl or aryl groups which may be substituted by halogen (see Division C2). The resin may be chlorinated polyethylene, or polyvinylidene chloride but is preferably a vinyl halide resin or a copolymer of vinyl chloride with an ethylenically unsaturated compound, e.g. a copolymer of vinyl chloride with vinyl-acetate, -propionate, -butyrate or -benzoate, vinylidene chloride, diethyl fumarate, diethyl maleate or other alkyl fumarate or maleate, an alkyl acrylate or methacrylate, methyl a -chloroacrylate, styrene, trichloroethylene, a vinyl ether, a vinyl ketone, 1-fluoro-1-chloroethylene, acrylonitrile, chloroacrylonitrile, allylidene- and chloroallylidene diacetate, or a copolymer of vinyl chloride, vinyl acetate and maleic anhydride (86:13:1). Conventional resin additives, e.g. plasticizers, pigments, fillers, dyes, U.V. light absorbing agents and densifying agents may also be present and specified additional additives are di-2-ethylhexyl phthalate, dibutyl and dihexyl sebacates, tricresyl phosphate, barium and cadmium laurates, calcium stearate, cadmium octoate, barium octoate and barium octyl phenolate. The oxetane ring-containing phosphites of Formulae I, II and III may be polymerized, e.g. by contacting with boron fluoride or its complexes to form flameproof oxetane polymers and may also be used as cross-linking agents with 3,3-bis-(chloromethyl) oxetane.ALSO:The invention comprises compounds of the general formulae in which n is 0 or 1, R1 is an aryl, aralkyl or alkaryl group or an alkyl group which may be substituted with a halogen atom, a cyano group or a group -OR in which R is an alkyl, alkenyl, aryl, alkaryl, aralkyl, acyl or abietyl group and the groups R2, R3 and R4 which may be the same or different represent a group of the formula in which n is 0 or 1, or an alkyl, cycloalkyl, alkaryl, aralkyl or aryl group which may be substituted by halogen. The compounds of Formulae I and II may be obtained by reacting as appropriate 1 to 3 moles of an oxetane ring-containing alcohol of the formula or 1 mole of an oxetane ring-containing alcohol of the formula or 1 mole of each of the alcohols IV and (V) with 1 mole of a trisubstituted phosphite of the formula (R4O)P(OR2)(OR3) in the presence of an alkaline catalyst. Compounds of Formula (III) may be obtained by reacting 3 moles of an alcohol of Formula V with 2 moles of a phosphite of the formula (R4O)-P(OR2)(OR3) in the presence of an alkaline catalyst. Also, compounds of Formula I and III may be obtained by reacting the alcohol of Formula IV or V with one or two moles, respectively, of PCl3 in the presence of 3 or 6 moles, respectively, of a hydrogen chloride acceptor, e.g. a tertiary amine such as pyridine or triethylamine. Suitable alkaline catalysts in the transesterification reaction are sodium-phenolate, -methylate, -decylate, and -cresylate, sodium hydroxide, sodium and alcohol, or potassium phenolate and suitable trisubstituted phosphites for use as starting materials are triphenyl, tri-p-tolyl, tri-p-chlorophenyl, tridecyl, tricyclohexyl, trimethyl, tribenzyl and diphenyl decyl phosphites. The phenol or alkanol formed is suitably removed by vacuum distillation. Compounds of Formula II in which R4 is the oxetane ring-containing group may also be obtained by reacting a compound of Formula II, in which R4 is other than the oxetane ring-containing group with an oxetane ring-containing mono-alcohol. Several examples are given and the products are useful as stabilizers for halogen-containing synthetic resins and may be polymerized to form flame-proof polymers (see Division C3). Specification 758,450 is referred to.

GB35151/62A
1961-09-14
1962-09-14
New phosphite esters

Expired

GB1017697A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US137997A

US3209013A
(en)

1961-09-14
1961-09-14
Oxetane ring containing phosphites

Publications (1)

Publication Number
Publication Date

GB1017697A
true

GB1017697A
(en)

1966-01-19

Family
ID=22479977
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB35151/62A
Expired

GB1017697A
(en)

1961-09-14
1962-09-14
New phosphite esters

Country Status (5)

Country
Link

US
(1)

US3209013A
(en)

BE
(1)

BE622418A
(en)

GB
(1)

GB1017697A
(en)

NL
(2)

NL283094A
(en)

SE
(1)

SE305742B
(en)

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

JP2000327673A
(en)

*

1999-03-12
2000-11-28
Ube Ind Ltd
Preservation of oxetane compound

Families Citing this family (15)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3287328A
(en)

*

1959-09-10
1966-11-22
Eastman Kodak Co
Organophosphorus compounds derived from bis (halomethyl) oxetanes and thietanes

US3354155A
(en)

*

1963-10-14
1967-11-21
Pfizer & Co C
Aminoalkylphosphonium compounds and process for the use thereof

US3449369A
(en)

*

1965-11-22
1969-06-10
Du Pont
Oxetane derivatives

US4323501A
(en)

*

1971-08-11
1982-04-06
Bayer Aktiengesellschaft
Esters of phosphorous acid

US4073769A
(en)

*

1971-08-11
1978-02-14
Bayer Aktiengesellschaft
Esters of phosphorous acid

DE2510463C2
(en)

*

1975-03-11
1986-04-03
Bayer Ag, 5090 Leverkusen

Stabilizer mixtures and use of stabilizer mixtures to stabilize polycarbonates

US4102859A
(en)

*

1975-03-11
1978-07-25
Bayer Aktiengesellschaft
Stabilizer mixtures

US4335039A
(en)

*

1978-11-02
1982-06-15
General Electric Company
Thermally stable polycarbonate compositions

DE4029536A1
(en)

*

1990-09-18
1992-03-19
Bayer Ag

POLYMERISATE MIXTURES WITH IMPROVED THERMOSTABILITY II

DE19544675A1
(en)

*

1995-11-30
1997-06-05
Bayer Ag

Polymer molding compounds stabilized with phosphorous acid esters

AU2013211125A1
(en)

2012-01-19
2014-08-07
Bayer Intellectual Property Gmbh
Plastic film for printing by dye diffusion thermal transfer printing

CN104039562A
(en)

2012-01-19
2014-09-10
拜耳知识产权有限责任公司
Plastic film for printing by dye diffusion thermal transfer printing

CN107621752B
(en)

2016-07-13
2019-11-12
常州强力先端电子材料有限公司
One specific admixture type photosensitive resin and preparation method thereof

CN107619399B
(en)

2016-07-13
2021-04-27
常州强力先端电子材料有限公司
Polyfunctional oxetane compound and preparation method thereof

JPWO2022176964A1
(en)

2021-02-18
2022-08-25

Family Cites Families (11)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US2594322A
(en)

*

1950-06-09
1952-04-29
Phillips Petroleum Co
Substituted oxacycloalkanes

NL180786B
(en)

*

1951-08-22

Nat Res Dev

DEVICE FOR EXAMINATION OF SAMPLES.

US2770610A
(en)

*

1952-10-30
1956-11-13
Monsanto Chemicals
Esters of epoxidized phosphonic acids and halogenated organic materials stabilized therewith

US2856369A
(en)

*

1953-05-08
1958-10-14
Shell Dev
Epoxy-substituted esters of phosphoruscontaining acid and their polymers

US2913464A
(en)

*

1956-07-13
1959-11-17
Hercules Powder Co Ltd
Method of improving monomeric material for preparation of oxetane polymers

US3006929A
(en)

*

1957-09-24
1961-10-31
Searle & Co
1-methyl-17-alkyl-19-nortestosterones

US3093660A
(en)

*

1959-01-15
1963-06-11
Du Pont
Polymeric products of decaborane and cyclic ethers and their preparation

US2997454A
(en)

*

1959-05-18
1961-08-22
Argus Chem
Polyvinyl chloride stabilizer combinations of phosphorus acid with triphosphites andheavy metal salts

US3041350A
(en)

*

1959-09-10
1962-06-26
Eastman Kodak Co
New organophosphorus compounds derived from bis(halomethyl)oxetanes and thietanes

US3157675A
(en)

*

1960-07-19
1964-11-17
Celanese Corp
Esters of thionophosphoric acid with acetal-alcohols

GB1047426A
(en)

*

1962-08-03

0

BE
BE622418D
patent/BE622418A/xx
unknown

NL
NL134940D
patent/NL134940C/xx
active

NL
NL283094D
patent/NL283094A/xx
unknown

1961

1961-09-14
US
US137997A
patent/US3209013A/en
not_active
Expired – Lifetime

1962

1962-09-13
SE
SE9909/62A
patent/SE305742B/xx
unknown

1962-09-14
GB
GB35151/62A
patent/GB1017697A/en
not_active
Expired

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

JP2000327673A
(en)

*

1999-03-12
2000-11-28
Ube Ind Ltd
Preservation of oxetane compound

Also Published As

Publication number
Publication date

NL283094A
(en)

US3209013A
(en)

1965-09-28

NL134940C
(en)

SE305742B
(en)

1968-11-04

BE622418A
(en)

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