CA2489570A1 - Novel phase change solvents - Google Patents

Novel phase change solvents Download PDF

Info

Publication number
CA2489570A1
CA2489570A1 CA002489570A CA2489570A CA2489570A1 CA 2489570 A1 CA2489570 A1 CA 2489570A1 CA 002489570 A CA002489570 A CA 002489570A CA 2489570 A CA2489570 A CA 2489570A CA 2489570 A1 CA2489570 A1 CA 2489570A1
Authority
CA
Canada
Prior art keywords
phase change
formula
difunctional
change solvent
solvent
Prior art date
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.)
Granted
Application number
CA002489570A
Other languages
French (fr)
Other versions
CA2489570C (en
Inventor
Steven Daryl Smith
Mark William Hamersky
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.)
Procter and Gamble Co
Original Assignee
Individual
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.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2489570A1 publication Critical patent/CA2489570A1/en
Application granted granted Critical
Publication of CA2489570C publication Critical patent/CA2489570C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated
    • C08G64/0216—Aliphatic polycarbonates saturated containing a chain-terminating or -crosslinking agent
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/02—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from isocyanates with formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/164—Unsaturated ethers containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • C07C69/82—Terephthalic acid esters
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0847—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers
    • C08G18/0852—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers the solvents being organic
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/22—General preparatory processes using carbonyl halides
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • 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
    • C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0016—Plasticisers
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/205—Compounds containing groups, e.g. carbamates

Abstract

Phase change solvents for thermoplastic polymers to provide blended compositions. Above the phase change temperature of the solvent, the phase change solvent solubilizes or intimately mixes with the thermoplastic polyme r. Below the phase change temperature of the solvent, the phase change solvent solidifies or crystallizes within the thermoplastic matrix. The phase change behavior of these materials produce blended compositions that exhibit lowere d shear viscosity and lowered processing temperature without substantially compromising mechanical properties of the thermoplastic polymer. The present invention also relates to a method of improving the processability of a thermoplastic polymer using the phase change solvent.

Claims (19)

1. A composition comprising: a phase change solvent having the general formula:
(I) R' - P y - (Q - P x)n-1 - Q - P y - R;
(II) R' - P y - (Q - P x)n - R; or (IV-a) R' - (Q - P x)n-1 - Q - P y- R
wherein Q is a substituted or unsubstituted difunctional aromatic moiety;
P is CH2;
R and R' are independently selected from the group consisting of H, CH3, COOH, CONHR1, CONR1R2, NHR3, NR3R4, hydroxy, and C1-C30 alkoxy; wherein R1, R2, R3 and R4 are independently H or linear or branched alkyl from C1-C30;
x and y are independently an integer from 1 to 30, and x .noteq.y;
n is an integer from 1 to 7 when the solvent has the formula (II); and n is an integer from 2 to 8 when the solvent has the formula (I) or (IV), wherein the phase change solvent has a phase change in a temperature range from 40°C to 250°C.
2. A composition comprising: a phase change solvent having the general formula:
(V) R' - P y - (W - R")n-1 - W - P y - R
(VI) R' - P y - (W - R")n - R or (VII) R' - (W - R")n-1 - W - P y- R
wherein W is selected from the group consisting of -C(=O)-O-, -O-C(=O)-, -O-C(=O)-O-, -C(=O)-NH-, -NH-C(=O)-, imide, -O-, -NR9-C(=O)-O-, and -NR9-C(=O)-NR10-, wherein R9 and R10 are independently H or linear or branched alkyl from C1-C30;
P is CH2;
R and R' are independently selected from the group consisting of H, CH3, COOH, CONHR1, CONR1R2, NHR3, NR3R4, hydroxy, and C1-C30 alkoxy; wherein R1, R2, R3 and R4 are independently H or linear or branched alkyl from C1-C30;
R" is linear or branched C1-C30 alkyl and R" .noteq. P y;
y is an integer from 1 to 30;

n is an integer from 1 to 7 when the solvent has the formula (VI); and n is an integer from 2 to 8 when the solvent has the formula (V) or (VII) wherein the phase change solvent has a phase change in a temperature range from 40°C to 250°C.
3. A composition comprising: a phase change solvent having the general formula:
(VIII) R' - P y - (W - R'' - W' - R''')n-1 - W - P y - R, or (IX) R' - P y - (W - R'' - W' - R''')n - R
(X) R' - (W - R'' - W' - R''')n-1 - W - P y - R
wherein W and W' are independently selected from the group consisting of -C(=O)-O-, -O-C(=O)-, -O-C(=O)-O-, -C(=O)-NH-, -NH-C(=O)-, imide, -O-, -N R9-C(=O)-O-, -O-C(=O)-NR9-, -NR9-C(=O)-N R10-, and -NR10-C(=O)-NR9-; wherein when W and W' are the same, R" and R"' are not the same; and wherein R9 and R10 are independently H or linear or branched alkyl from C1-C30;
P is CH2;
R and R' are independently selected from the group consisting of H, CH3, COOH, CONHR1, CONR1R2, NHR3, NR3R4, hydroxy, and C1-C30 alkoxy; wherein R1, R2, R3 and R4 are independently H or linear or branched alkyl from C1-C30;
R" and R"' are independently linear or branched C1-C30 alkyl;
when R" = P y, R"' .noteq. P y;
when R" .noteq. P y, R"' may be the same as or different than P y;
y is an integer from 1 to 30;
n is an integer from 1 to 7 when the solvent has formula (IX); and n is an integer from 2 to 8 when the solvent has formula (VIII) or (X) wherein the phase change solvent has a phase change in a temperature range from 40°C to 250°C.
4. The composition of Claim 1 wherein the phase change solvent has a number-average molecular weight from 150 to 5,000.
5. The composition of Claim 2 wherein the phase change solvent has a number-average molecular weight from 150 to 5,000.
6. The composition of Claim 3 wherein the phase change solvent has a number-average molecular weight from 150 to 5,000.
7. The composition of Claim 1 wherein an AA ratio (C aliphatic to C aromatic) of the phase change solvent ranges from 0.25 to 4.
8. The composition of Claim 2 wherein an AP ratio (number of aliphatic carbons to number of polar groups) of the phase change solvent ranges from 1 to 25.
9. The composition of Claim 2 wherein an AP ratio (number of aliphatic carbons to number of polar groups) of the phase change solvent ranges from 1 to 25.
10. The composition of Claim 1 wherein Q is substituted with one or more substituents selected from the group consisting of H, C1-C30 alkyl, COOH, CONHR5, CONR5R6, NHR7, NR7R8, hydroxy, C1-C30 alkoxy, SO3H, and halogen; wherein R5, R6, R7 and R8 are independently H or linear or branched alkyl from C1-C30.
11. A process for preparing the phase change solvent having formula (I) or (II) of Claim 1;
comprising:
combining A) a monofunctional aliphatic alcohol or monofunctional aliphatic amine having y carbons;
B) a difunctional aromatic diacid, difunctional aromatic acid salt, difunctional aromatic ester, or difunctional aromatic isocyanate; and C) a difunctional aliphatic diol or a difunctional aliphatic diamine having x carbons;
in a molar ratio of A:B:C of 2 : n : n-1 where 2<= n <= 8 and under conditions to produce the phase change solvent having formula (I);
in a molar ratio of A:B:C of 1 : n : n where 1<= n <= 7) and under conditions to produce the phase change solvent having formula (II).
12. A process for preparing the phase change solvent having formula (I) or (IV-a) of Claim 1, comprising:

combining D) a monofunctional aliphatic acid, monofunctional aliphatic acid salt, monofunctional aliphatic ester, or monofunctional aliphatic isocyanate;
E) a difunctional aromatic diol, or difunctional aromatic diamine; and F) a difunctional aliphatic diacid, difunctional aliphatic acid salt, difunctional aliphatic ester, or difunctional aliphatic isocyanate having x carbons;
in a molar ratio of D:E:F of 2 : n : n-1 where 2<=n <= 8 and under conditions to produce the phase change solvent having formula (I); or in a molar ratio of D:E:F of 1 : n : n-1 where 2<= n <= 8 and under conditions to produce the phase change solvent having formula (IV).
13. A process for preparing the phase change solvent having formula (V) or (VI) of Claim 2, comprising:
combining A) a monofunctional aliphatic amine having y carbons;
B) a difunctional di-isocyanate; and C) an aliphatic difunctional diamine having x carbons;
in a molar ratio of A:B:C of 2 : n : n-1 where 2<= n <= 8 and under conditions to produce the phase change solvent having formula (V); or in a molar ratio of A:B:C of 1 : n : n where 1<= n <= 7 and under conditions to produce the phase change solvent having formula (VI).
14. A process for preparing the phase change solvent having formula (V) or (VII) of Claim 2, comprising:
combining D) a monofunctional aliphatic acid salt having y carbons;
E) a difunctional diol; and F) phosgene;
in a molar ratio of D:E:F of 2 : n : n-1 where 2<= n <=8 and under conditions to produce the phase change solvent having formula (V); or in a molar ratio of D:E:F of 1 : n : n-1 where 2<= n <= 8 and under conditions to produce the phase change solvent having formula (VII).
15. A process for preparing the phase change solvent having formula (V) or (VII) of Claim Z, comprising:

combining G) a monofunctional aliphatic isocyanate having y carbons;
H) a difunctional diamine; and I) a difunctional aliphatic di-isocyanate having x carbons;
in a molar ratio of G:H:I of 2 : n : n-1 where 2<= n <= 8 and under conditions to produce the phase change solvent having formula (V); and in a molar ratio of G:H:I of 1 : n : n-1 where 2<= n <= 8 and under conditions to produce the phase change solvent having formula (VII).
16. A process for preparing the phase change solvent having formula (V) or (VI) of Claim 2, comprising:
combining J) a monofunctional aliphatic alcohol having y carbons;
K) phosgene; and L) a difunctional aliphatic diol having x carbons;
in a molar ratio of J:K:L of 2 : n : n-1 where 2<= n <= 8 and under conditions to produce the phase change solvent having formula (V); or in a molar ratio of J:K:L of 1 : n : n where 1<= n <= 7 and under conditions to produce the phase change solvent having formula (VI).
17. A process for preparing the phase change solvent having formula (VIII) or (IX) of Claim 3, comprising:
combining A) a monofunctional aliphatic alcohol or monofunctional aliphatic amine having y carbons;
B) a difunctional diacid, difunctional acid salt, difunctional ester, difunctional isocyanate, or difunctional phosgene; and C) a difunctional aliphatic diol or difunctional aliphatic diamine having x carbons;
in a molar ratio of A:B:C of 2 : n : n-1 where 2<= n <= 8 and under conditions to produce the phase change solvent having formula (VIII);
in a molar ratio of A:B:C of 1 : n : n where 1<= n <= 7 and under conditions to produce the phase change solvent having formula (IX).
18. A process for preparing the phase change solvent having formula (VIII) or (X) of Claim 3, comprising:

combining D) a monofunctional aliphatic acid, monofunctional aliphatic acid salt, monofunctional aliphatic ester, or monofunctional aliphatic isocyanate;
E) a difunctional diol, or difunctional diamine; and F) a difunctional aliphatic diacid, difunctional aliphatic acid salt, difunctional aliphatic ester, difunctional aliphatic isocyanate, or phosgene;
in a molar ratio of D:E:F of 2 : n : n-1 where 2<= n <= 8 and under conditions to produce the phase change solvent having formula (VIII); and in a molar ratio of D:E:F of 1 : n : n-1 where 2<= n <= 8 and under conditions to produce the phase change solvent having formula (X).
19. A phase change solvent having a phase change in a temperature range from 40°C to 250°C and, when blended with a thermoplastic polymer at 20% solvent and 80% polymer, the blend has a viscosity less than 50% of a viscosity of the thermoplastic polymer absent the phase change solvent, and has a tensile strength at least 70% of a tensile strength of the thermoplastic polymer absent the phase change solvent, and wherein viscosity is measured at a temperature of 50° above a softening point of the polymer, and tensile strength is measured at ambient temperature.
CA2489570A 2002-07-31 2003-07-14 Novel phase change solvents Expired - Fee Related CA2489570C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US39996302P 2002-07-31 2002-07-31
US60/399,963 2002-07-31
PCT/US2003/022036 WO2004011523A2 (en) 2002-07-31 2003-07-14 Novel phase change solvents

Publications (2)

Publication Number Publication Date
CA2489570A1 true CA2489570A1 (en) 2004-02-05
CA2489570C CA2489570C (en) 2010-12-21

Family

ID=31188650

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2489570A Expired - Fee Related CA2489570C (en) 2002-07-31 2003-07-14 Novel phase change solvents

Country Status (9)

Country Link
US (1) US7524984B2 (en)
EP (2) EP1562998B1 (en)
JP (1) JP2005533905A (en)
CN (1) CN100532421C (en)
AT (2) ATE473205T1 (en)
AU (1) AU2003253917A1 (en)
CA (1) CA2489570C (en)
DE (2) DE60332550D1 (en)
WO (1) WO2004011523A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006118906A2 (en) * 2005-04-29 2006-11-09 The Procter & Gamble Company Polymeric film exhibiting improved anti-blocking characteristics and process of making
EP2251372B1 (en) 2005-04-29 2013-07-17 The Procter & Gamble Company Polymeric film exhibiting improved anti-blocking characteristics and process of making
US8968265B2 (en) * 2005-09-30 2015-03-03 The Procter & Gamble Company Absorbent article fastening device having stiffness changing characteristics
US20200002591A1 (en) * 2017-03-03 2020-01-02 Nissan Chemical Corporation Heat-storage material comprising metal salt of cyanuric acid
CN108645890B (en) * 2018-07-20 2023-09-19 四川建筑职业技术学院 Testing device and testing method for testing temperature regulating performance of phase-change material
CN109942431A (en) * 2019-04-02 2019-06-28 苏州湘园新材料股份有限公司 A kind of aromatic diol class compound and preparation method thereof
WO2023119299A1 (en) * 2021-12-22 2023-06-29 Nostromo Ltd. Nucleation agent

Family Cites Families (69)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US849086A (en) * 1906-05-16 1907-04-02 William W Rosenfield Phonograph.
US2075107A (en) * 1931-12-10 1937-03-30 Union Carbide & Carbon Corp Mixed esters and process for making the same
GB568571A (en) * 1941-09-19 1945-04-11 Ici Ltd Improved preparation of plasticised compositions comprising synthetic linear polyamides
US2453264A (en) * 1944-09-28 1948-11-09 Chessle E Rehberg Cellulose ester or ether plasticized with ethyl alpha-carbethoxyethoxyethyl carbonate
US2777871A (en) * 1952-08-05 1957-01-15 Columbia Southern Chem Corp Bis nu-substituted carbamic acid esters of polyhydric alcohols and process
GB849086A (en) * 1956-08-06 1960-09-21 Pennsylvania Ind Chemical Corp Mastic tile resin
NL301908A (en) * 1962-12-22
NL297228A (en) * 1963-02-11
US3459832A (en) * 1965-09-24 1969-08-05 Monsanto Co Crystalline polystyrene having activity as a polymerization catalyst
DE1260132B (en) 1966-07-27 1968-02-01 Basf Ag Process for the production of magnetogram carriers
GB1181807A (en) 1966-10-18 1970-02-18 Dunlop Co Ltd Improvements in or relating to Adhesives, Metal Primers and Protective Coatings
GB1193626A (en) 1966-10-18 1970-06-03 Dunlop Co Ltd Improvements in or relating to Adhesives and Sealants.
GB1193627A (en) 1966-10-18 1970-06-03 Dunlop Co Ltd Improvements in or relating to Adhesive Compositions.
US4111888A (en) * 1970-10-27 1978-09-05 Ciba Geigy Ag Plasticized polymers of vinyl acetate
US3734891A (en) * 1971-05-24 1973-05-22 Fmc Corp Transesterification catalysts for production of poly (c4 to c12 alkyleneterephthalate
BE787079A (en) * 1971-08-03 1973-02-02 Polymer Corp CURING LIQUID COMPOSITION AND ITS APPLICATIONS TO COATING SURFACES
US3852096A (en) * 1972-02-25 1974-12-03 Exxon Research Engineering Co Process for fabricating an article from a multiphase copolymer composition
US3870841A (en) * 1972-10-02 1975-03-11 Exxon Research Engineering Co Flexible polymeric compositions comprising a normally plastic polymer sulfonated to about 0.2 to about 10 mole % sulfonate
US3981838A (en) * 1974-10-16 1976-09-21 Standard Oil Company (Indiana) Lubricant for polyvinyl chloride
JPS5950113B2 (en) * 1975-11-05 1984-12-06 株式会社東芝 semiconductor equipment
US4098751A (en) * 1976-12-08 1978-07-04 General Electric Company Organic carbonate plasticized polycarbonate composition
US4131581A (en) * 1976-12-13 1978-12-26 E. I. Du Pont De Nemours And Company Adhesive compositions consisting essentially of a vinyl alcohol polymer, a crystalline solvent and a viscosity reducing diluent
US4123413A (en) * 1976-12-16 1978-10-31 General Electric Company Polycarbonate composition containing urethane plasticizer
US4146522A (en) * 1977-02-04 1979-03-27 Armstrong Cork Company Smoke suppressant composition
US4210568A (en) * 1978-04-20 1980-07-01 Exxon Research & Engineering Co. Plasticization of neutralized sulfonated elastomeric polymer with organic carbamates
US4325903A (en) 1980-07-15 1982-04-20 Celanese Corporation Processing of melt processible liquid crystal polymer by control of thermal history
US4293473A (en) * 1980-07-25 1981-10-06 E. I. Du Pont De Nemours And Company Polyvinyl alcohol - crystalline solvent system based compositions modified with ethylene polymer
DE3030014C2 (en) 1980-08-08 1983-08-11 Fa. Carl Freudenberg, 6940 Weinheim Elastomer composition
US4500662A (en) * 1981-04-03 1985-02-19 The B. F. Goodrich Company Polysubstituted α-aminoacetamides
US4387214A (en) * 1981-06-29 1983-06-07 Eastman Kodak Company Thermosetting powder coating compositions
US4442270A (en) * 1981-06-29 1984-04-10 Eastman Kodak Company Thermosetting powder coating compositions
US4618630A (en) * 1984-08-27 1986-10-21 The Dow Chemical Co. Organic polymer composition containing an antistatic agent comprising a nonvolatile ionizable metal salt and a salt or ester of a carboxylic acid
US4578302A (en) * 1985-06-27 1986-03-25 National Starch And Chemical Corporation Reinforced tape laminates
GB8531685D0 (en) * 1985-12-23 1986-02-05 Boc Group Plc Liquid-vapour contact apparatus
US4745026A (en) * 1986-03-03 1988-05-17 Mitsubishi Paper Mills, Ltd. Thermal delayed tack sheets
US4704110A (en) * 1986-06-20 1987-11-03 National Starch And Chemical Corporation Hot melt pressure sensitive positioning adhesives
JPS63182349A (en) 1987-01-26 1988-07-27 Mitsui Petrochem Ind Ltd Production of ultrahigh molecular weight polyolefin composition
JPS63227658A (en) 1987-03-17 1988-09-21 Mitsubishi Rayon Co Ltd Polyester polymer composition
US5627229A (en) * 1992-07-25 1997-05-06 H.B. Fuller Licensing & Financing, Inc. Hot melt adhesive having controlled property change
US5624986A (en) * 1988-06-30 1997-04-29 H. B. Fuller Licensing & Financing Inc. Hot melt adhesive having controlled property change
US4882375A (en) * 1988-09-01 1989-11-21 General Electric Company Polyesters with modified melt viscosity
JPH02189348A (en) 1989-01-19 1990-07-25 Kao Corp Melt viscosity depressant for polyester resin
JPH02196844A (en) 1989-01-25 1990-08-03 Sanken Kako Kk New plasticized polymer composition
JPH03229751A (en) * 1990-02-02 1991-10-11 Polyplastics Co Polyester resin composition and molding
US5389711A (en) * 1990-02-14 1995-02-14 Shell Oil Company Plasticisers for salt functionalized polyvinyl aromatics
US6117176A (en) * 1993-11-15 2000-09-12 Applied Elastomerics, Inc. Elastic-crystal gel
US5352531A (en) * 1990-12-20 1994-10-04 Ozko, Inc. Coating solution for treating basement walls
US5310814A (en) * 1991-03-15 1994-05-10 Exxon Chemical Patents Inc. Viscosity modifier polybutadiene polymers
JPH05125240A (en) 1991-11-05 1993-05-21 Sanken Kako Kk Heat-resistant chlorinated vinyl resin composition
CA2112781A1 (en) * 1993-01-13 1994-07-14 Paul C. Yung Blends of liquid crystalline polymers and poly(arylene sulfide)s having reduced viscosities
IT1272002B (en) * 1993-03-10 1997-06-10 Enichem Sintesi VULCNIZABLE COMPOSITIONS OF NITRILE RUBBER.
US5342858A (en) * 1993-06-30 1994-08-30 The Procter & Gamble Company Elastomeric adhesive foam
US5714254A (en) * 1993-12-15 1998-02-03 Exxon Chemical Patents Inc. Low viscosity hot melt pressure sensitive adhesive compositions
ATE180816T1 (en) * 1994-03-25 1999-06-15 Shell Int Research CONVEYOR BELTS DERIVED FROM COMPOSITIONS BASED ON VINYL AROMATIC MONOMER CONJUGATE DIENE BLOCK COPOLYMERS
US5910527A (en) * 1994-04-28 1999-06-08 Ato Findley, Inc. Hot melt adhesive having a high acid number for disposable soft goods
WO1996005253A1 (en) 1994-08-15 1996-02-22 Akzo Nobel Nv Melt viscosity reduction of polycarbonate containing liquid crystalline block copolymer
US5853874A (en) * 1994-11-28 1998-12-29 Exxon Chemical Patents, Inc. Low viscosity hot melt pressure sensitive ashesive compositions
JP3103832B2 (en) * 1995-09-25 2000-10-30 東洋インキ製造株式会社 Delayed tack adhesive composition
US5633319A (en) * 1996-01-16 1997-05-27 General Electric Company Compatibilized blends of polyetherimides and liquid crystalline polyesters
CA2202693A1 (en) * 1996-04-19 1997-10-19 Tsutomu Tomatsu Thermoplastic resin compositions and temperature-dependent shape-transformable/fixable products making use of the same
US5939483A (en) * 1996-07-12 1999-08-17 H.B. Fuller Licensing & Financing, Inc. Low application temperature hot melt with excellent heat and cold resistance
US6187425B1 (en) * 1996-12-30 2001-02-13 Kimberly-Clark Worldwide, Inc. Elastic materials with improved performance at body temperature
EP0989162A4 (en) 1998-03-31 2002-11-06 Daicel Chem Thermoplastic resin composition, water-based composition, heat-sensitive pressure-sensitive adhesive, and heat-sensitive sheet
JP3327840B2 (en) * 1998-07-06 2002-09-24 三洋化成工業株式会社 Polyurethane resin slush molding materials
US6476122B1 (en) 1998-08-20 2002-11-05 Vantico Inc. Selective deposition modeling material
US6828017B2 (en) 2000-09-29 2004-12-07 Ricoh Company, Ltd. Heat-sensitive adhesive material, method of preparing same and method of using same
DE10064373A1 (en) * 2000-12-21 2002-06-27 Huels Troisdorf Film containing plasticizer and amide wax, useful as an intermediate layer for laminated safety glass plates, is based on partially acetylated polyvinyl alcohol
US6703115B2 (en) * 2001-05-01 2004-03-09 Eastman Chemical Company Multilayer films
JP2004020950A (en) * 2002-06-17 2004-01-22 Fuji Xerox Co Ltd Image recording body and image display body using the same

Also Published As

Publication number Publication date
CN100532421C (en) 2009-08-26
WO2004011523A3 (en) 2004-05-27
DE60333317D1 (en) 2010-08-19
WO2004011523A2 (en) 2004-02-05
EP1832570B1 (en) 2010-07-07
EP1832570A2 (en) 2007-09-12
JP2005533905A (en) 2005-11-10
CN1777630A (en) 2006-05-24
US7524984B2 (en) 2009-04-28
DE60332550D1 (en) 2010-06-24
EP1832570A3 (en) 2008-03-05
CA2489570C (en) 2010-12-21
EP1562998B1 (en) 2010-05-12
ATE467653T1 (en) 2010-05-15
AU2003253917A1 (en) 2004-02-16
EP1562998A2 (en) 2005-08-17
ATE473205T1 (en) 2010-07-15
US20040021130A1 (en) 2004-02-05
AU2003253917A8 (en) 2004-02-16

Similar Documents

Publication Publication Date Title
DE102012208602B4 (en) Solid phase change ink
KR100335545B1 (en) Polyester, polyester whitening method, toner composition for polyester and articles comprising polyester
JP2966086B2 (en) Rich pigment and colored semi-crystalline powder
US5281659A (en) Colored polyester compositions
US4403092A (en) Polyesters containing copolymerized, anthraquinone colorant compounds containing sulfonamido groups
US20110193016A1 (en) Polyimide precursor solution composition
US4937315A (en) Transparent amorphous polyamide having high Tg from hindered aromatic diamine and branched chain aliphatic diamine
CA2489571A1 (en) Phase change solvents for thermoplastic polymers
CA2489570A1 (en) Novel phase change solvents
CA1325307C (en) Polyamide compositions comprising a thermoplastically processible aromatic polyamide and useful as molding compounds
JP2003335971A (en) Method for producing n,n&#39;-disubstituted 1,4- diaminoanthraquinone
JP2619043B2 (en) Copolymer composition
KR101999864B1 (en) Phase change ink comprising a modified polysaccharide composition
US5955564A (en) 1,5(8)-bis (substituted-N-propylamino)-4,8(5)-bis(arylthio)anthraquinone compounds
US3491057A (en) Saturated polyesters stabilized with nitrogen-containing compounds
US4810770A (en) Elastomers
JP6483481B2 (en) Torxic acid based polymer and its production intermediate
JPS583498B2 (en) Anti Casareta Polyurethane Elastomer Soseibutsu
US4833214A (en) Soluble heat-resistant aromatic polyamide terminated with aromatic amido moieties
US4792597A (en) Melt-processable polyesteramides having para-linked, substituted-phenylene radicals
US5420225A (en) Aramid compositions of improved solubility and flame retardancy
CN109206611B (en) PEG (polyethylene glycol) thioxanthone photoinitiator and photosensitive resin composition
US3789048A (en) Oligomer polyimide precursors
US8492462B2 (en) Colour stable thermoplastic composition
KR100641904B1 (en) Composition of thermoplastic elastomer resin having a low hardness

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20160714