US4030933A
Expired / Lapsed
US
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Phosphorus and halogen containing polymers of bis-hydroxyethyl terephthalate as flame retardant additives
Assignee: Celanese Corp
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Filing: 1975-04-07
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Granted: 1977-06-21
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Expires: 1995-04-07
Abstract
Abstract The present invention provides a process for preparing phosphorus and halogen containing polymers useful as flame retardant additives in cellulose acetate or cellulose triacetate fibers or films. The phosphorus and halogen containing polymers may be prepared by reacting a halogenated derivative of bis-hydroxyethyl terephthalate with a halogen containing phosphorus monomer having the formula ##STR1## wherein R represents a radical selected from the group consisting of (a) alkyl, (b) bromoalkyl, (c) chloroalkyl, (d) alkylamido and (e) dialkylamido radicals, wherein the alkyl substituents of the foregoing may contain from 1 to 10 carbon atoms, (f) cyclohexyl, (g) phenyl, (h) benzyl, (i) tolyl, and (j) xylyl, and X represents a halogen atom (preferably chlorine or bromine). Cellulose acetate and cellulose triacetate fibers and films containing as little as two percent by weight of the polymeric flame retardant additives are rendered both non-burning and resistant to loss of the polymeric flame retardant additive during use.
Inventors
- 👤 Anthony B. Conciatori
- 👤 Robert W. Stackman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 02:26
CPC Classifications
C; C08; C08G; C08G79/00; C08G79/02; C08G79/04; C08L; C08L1/00; C08L1/08; C08L1/10; C08L1/12
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
145 words
A process for preparing phosphorus and halogen containing polymers useful as flame retardant additives which process comprises reacting a halogenated derivative of bis-hydroxyethyl terephthalate with a halogen containing phosphorus monomer having the formula ##STR8## wherein R represents a radical selected from the group consisting of (a) alkyl, (b) bromoalkyl, (c) chloroalkyl, (d) alkylamido and (e) dialkylamido radicals, wherein the alkyl substituents of the foregoing may contain from 1 to 10 carbon atoms, (f) cyclohexyl, (g) phenyl, (h) benzyl, (i) tolyl and (j) xylyl, and X represents a halogen atom wherein said reaction is carried out in a molar ratio of halogenated derivative of bis-hydroxyethyl terephthalate to halogen containing phosphorus monomer of from about 0.33 to 1 to about 3 to 1, and at a temperature of from about -40° to about 200° C. and at a pressure of from about 0.01 to about 100 atmospheres.
Claim 2
Dependent Claim
145 words
A process for preparing phosphorus and halogen containing polymers useful as flame retardant additives which process comprises reacting a halogenated derivative of bis-hydroxyethyl terephthalate with a halogen containing phosphorus monomer having the formula ##STR8## wherein R represents a radical selected from the group consisting of (a) alkyl, (b) bromoalkyl, (c) chloroalkyl, (d) alkylamido and (e) dialkylamido radicals, wherein the alkyl substituents of the foregoing may contain from 1 to 10 carbon atoms, (f) cyclohexyl, (g) phenyl, (h) benzyl, (i) tolyl and (j) xylyl, and X represents a halogen atom wherein said reaction is carried out in a molar ratio of halogenated derivative of bis-hydroxyethyl terephthalate to halogen containing phosphorus monomer of from about 0.33 to 1 to about 3 to 1, and at a temperature of from about -40° to about 200° C. and at a pressure of from about 0.01 to about 100 atmospheres.
Claim 3
Dependent Claim
31 words
The process of claim 1 wherein said halogenated derivative of bis-hydroxyethyl terephthalate is selected from the group consisting of tetrachloro bis-hydroxyethyl terephthalate, dichloro bis-hydroxyethyl terephthalate, dibromo bis-hydroxyethyl terephthalate, and mixtures thereof.
Claim 4
Dependent Claim
18 words
The process of claim 1 wherein said reaction is carried out in the presence of a basic solvent.
Claim 5
Dependent Claim
34 words
The process of claim 1 wherein said reaction is carried out in the presence of a solvent and at least two moles of an acid acceptor for every mole of halogen containing phosphorus monomer.
Claim 6
Dependent Claim
144 words
A process for preparing phosphorus and halogen containing polymers useful as flame retardant additives which comprises reacting a halogenated derivative of bis-hydroxyethyl terephthalate with a halogen containing phosphorus monomer having the formula ##STR9## wherein R represents a radical selected from the group consisting of (a) alkyl, (b) bromoalkyl, (c) chloroalkyl, (d) alkylamido and (e) dialkylamido radicals wherein the alkyl substituents of the foregoing may contain from 1 to 10 carbon atoms, (f) cyclohexyl, (g) phenyl, (h) benzyl, (i) tolyl and (j) xylyl, and X represents a halogen atom wherein said reaction is carried out in a molar ratio of halogenated derivative of bis-hydroxyethyl terephthalate to halogen containing phosphorus monomer of from about 0.66 to 1 to about 1.5 to 1 and at a temperature of from about 0° to about 100° C and at a pressure of from about 0.1 to about 10 atmospheres.
Claim 7
Dependent Claim
144 words
A process for preparing phosphorus and halogen containing polymers useful as flame retardant additives which comprises reacting a halogenated derivative of bis-hydroxyethyl terephthalate with a halogen containing phosphorus monomer having the formula ##STR9## wherein R represents a radical selected from the group consisting of (a) alkyl, (b) bromoalkyl, (c) chloroalkyl, (d) alkylamido and (e) dialkylamido radicals wherein the alkyl substituents of the foregoing may contain from 1 to 10 carbon atoms, (f) cyclohexyl, (g) phenyl, (h) benzyl, (i) tolyl and (j) xylyl, and X represents a halogen atom wherein said reaction is carried out in a molar ratio of halogenated derivative of bis-hydroxyethyl terephthalate to halogen containing phosphorus monomer of from about 0.66 to 1 to about 1.5 to 1 and at a temperature of from about 0° to about 100° C and at a pressure of from about 0.1 to about 10 atmospheres.
Claim 8
Dependent Claim
37 words
The process of claim 5 wherein said halogenated derivative of bis-hydroxyethyl terephthalate is tetrachloro bis-hydroxyethyl terephthalate and said halogen containing phosphorus monomer is selected from the group consisting essentially of phenyl phosphonyl dichloride and chloromethyl phosphonyl dichloride.
Claim 9
Dependent Claim
18 words
The process of claim 6 wherein said reaction is carried out in the presence of a basic solvent.
Claim 10
Dependent Claim
106 words
A process for preparing phosphorus and halogen containing polymers useful as flame retardant additives which process comprises reacting tetrachloro bis-hydroxyethyl terephthalate with a halogen containing phosphorus monomer selected from the group consisting essentially of phenyl phosphonyl dichloride and chloromethyl phosphonyl dichloride in a molar ratio of tetrachloro bis-hydroxyethyl terephthalate to halogen containing phosphorus monomer of from about 0.90 to 1 to about 1.1 to 1, in the presence of at least two moles of a tertiary amine per mole of halogen containing phosphorus monomer at a temperature of from about 15° to about 65° C and a pressure of from about 0.8 to about 1.2 atmospheres.
Claim 11
Dependent Claim
106 words
A process for preparing phosphorus and halogen containing polymers useful as flame retardant additives which process comprises reacting tetrachloro bis-hydroxyethyl terephthalate with a halogen containing phosphorus monomer selected from the group consisting essentially of phenyl phosphonyl dichloride and chloromethyl phosphonyl dichloride in a molar ratio of tetrachloro bis-hydroxyethyl terephthalate to halogen containing phosphorus monomer of from about 0.90 to 1 to about 1.1 to 1, in the presence of at least two moles of a tertiary amine per mole of halogen containing phosphorus monomer at a temperature of from about 15° to about 65° C and a pressure of from about 0.8 to about 1.2 atmospheres.
Claim 12
Dependent Claim
81 words
A phosphorus and halogen containing polymer of the formula ##STR10## wherein the Y attached to the aromatic ring represents 1 to 4 halogen atoms; the R represents a radical selected from the group consisting of (a) alkyl, (b) bromoalkyl, (c) chloroalkyl, (d) alkylamido and (e) dialkylamido radicals, wherein the alkyl substituents of the foregoing may contain from 1 to 10 carbon atoms, (f) cyclohexyl, (g) phenyl, (h) benzyl, (i) tolyl and (j) xylyl; and n is an integer greater than 1.
Claim 13
Dependent Claim
81 words
A phosphorus and halogen containing polymer of the formula ##STR10## wherein the Y attached to the aromatic ring represents 1 to 4 halogen atoms; the R represents a radical selected from the group consisting of (a) alkyl, (b) bromoalkyl, (c) chloroalkyl, (d) alkylamido and (e) dialkylamido radicals, wherein the alkyl substituents of the foregoing may contain from 1 to 10 carbon atoms, (f) cyclohexyl, (g) phenyl, (h) benzyl, (i) tolyl and (j) xylyl; and n is an integer greater than 1.
Claim 14
Dependent Claim
46 words
The phosphorus and halogen containing polymer of claim 9 wherein said polymer contains from about 8 to about 60 percent by weight halogen, and from about 3 to about 10 percent by weight phosphorus, and n is an integer of from about 3 to about 50.
Claim 15
Dependent Claim
36 words
The phosphorus and halogen containing polymer of claim 10 wherein Y is selected from the group consisting of chlorine, bromine, and mixtures thereof, and R is selected from the group consisting essentially of phenyl or chloromethyl.
Claim 16
Dependent Claim
36 words
A phosphorus and halogen containing polymer of the formula ##STR11## wherein Y represents four chlorine atoms, R is selected from the group consisting essentially of phenyl and chloromethyl, and n is an integer greater than 1.
Claim 17
Dependent Claim
36 words
A phosphorus and halogen containing polymer of the formula ##STR11## wherein Y represents four chlorine atoms, R is selected from the group consisting essentially of phenyl and chloromethyl, and n is an integer greater than 1.
Claim 18
Dependent Claim
62 words
The phosphorus and halogen containing polymer of claim 12 wherein said polymer contains from about 10 to about 40 percent by weight chlorine, and from about 4 to about 9 percent by weight phosphorus, n is an integer of from about 5 to about 10, and wherein said polymer has a weight average molecular weight of from about 500 to about 20,000.
Claim 19
Dependent Claim
22 words
A flame retardant composition of matter comprising the phosphorus and halogen containing polymer of claim 9 and an acetate ester of cellulose.
Claim 20
Dependent Claim
30 words
The flame retardant composition of claim 14, wherein said composition is either a fiber or a film and said phosphorus and halogen containing polymer is not substantially removed by washing.
Claim 21
Dependent Claim
37 words
The flame retardant composition of claim 15 which comprises from about 2 to about 40 percent by weight phosphorus and halogen containing polymer and from about 60 to about 98 percent by weight acetate ester of cellulose.
Claim 22
Dependent Claim
22 words
A flame retardant composition of matter comprising the phosphorus and halogen containing polymer of claim 12 and an acetate ester of cellulose.
Claim 23
Dependent Claim
37 words
The flame retardant composition of claim 17 which comprises from about 4 to about 20 percent by weight phosphorus and halogen containing polymer and from about 80 to about 96 percent by weight acetate ester of cellulose.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-06-20 | 1980-12-20 | 1981-06-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-20 | 1984-12-20 | 1985-06-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-20 | 1988-12-20 | 1989-06-21 | $7700.00 | Window Closed / Lapsed |