# US 10,308,759 B2 · Aliphatic polycarbonate polyol compositions

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- Number: US 10,308,759 B2
- Document ID: US10308759B2
- Status: Granted
- Kind: B2
- Application number: 15/301,095
- Filed: 2015-04-03
- Published: 2017-01-26
- Granted: 2019-06-04
- Earliest claimed: 2014-04-03
- Assignees: Saudi Aramco Technologies Company
- Applicants: Saudi Aramco Technologies Company
- Inventors: Christopher A. Simoneau
- Web page: https://patentgrep.com/patent/US10308759B2

## CPC

- C08G 63/64: Polyesters containing both carboxylic ester groups and carbonate groups
- C08G 18/44: Polycarbonates
- C08G 18/72: Polyisocyanates or polyisothiocyanates
- C08G 64/0216: {containing a chain-terminating or -crosslinking agent}
- C08G 64/42: Chemical after-treatment
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present invention encompasses CO2-based polycarbonate polyols that do not degrade from the chain ends to form cyclic carbonate. Importantly, the inventive polyol compositions retain —OH end group functionality desirable for thermoset applications.

## Claims

### Claim 1

A method comprising the steps of:
i) reacting a polycarbonate polyol of formula P1-OH,
with a cyclic acid anhydride having a formula
to provide a polycarbonate polyol of formula P1-CO2H,
and
ii) further treating this polyol with an epoxide of formula
to yield a polymer composition of formula P1,
wherein:
is a multivalent moiety;
R1, R2, R3, and R4 are at each occurrence, independently selected from the group consisting of —H, fluorine, an optionally substituted C1-40 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, and an optionally substituted aryl group, where any two or more of R1, R2, R3, and R4 may optionally be taken together with intervening atoms to form one or more optionally substituted rings optionally containing one or more heteroatoms;
R1′, R2′, R3′, and R4′ are at each occurrence, independently selected from the group consisting of —H, fluorine, an optionally substituted C1-40 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, and an optionally substituted aryl group, where any two or more of R1′, R2′, R3′ and R4′ may optionally be taken together with intervening atoms to form one or more optionally substituted rings optionally containing one or more heteroatoms;
each n is independently, on average in the composition, within a range from about 2 to about 200;
Q is an optionally substituted bivalent moiety; and
x and y are each independently an integer from 0 to 6, where the sum of x and y is between 2 and 6.

### Claim 2 (depends on 1)

The method of claim 1, wherein the moiety
at each occurrence in the aliphatic polycarbonate chains is independently selected from the group consisting of:
wherein each Rx is independently selected from the group consisting of: optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl and optionally substituted heteroaryl.

### Claim 3 (depends on 1)

The method of claim 1, wherein the moiety
at each occurrence in the aliphatic polycarbonate chains is independently selected from the group consisting of:
wherein each Rx is independently selected from the group consisting of: optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl and optionally substituted heteroaryl.

### Claim 4 (depends on 1)

The method of claim 1, wherein the moiety
at each occurrence in the aliphatic polycarbonate chains is

### Claim 5 (depends on 1)

The method of claim 1, wherein Q is an optionally substituted bivalent moiety selected from the group consisting of:
where Ra and Rb are each independently selected from the group consisting of: —H, halogen, optionally substituted C1-8 aliphatic, and optionally substituted C1-8 heteroaliphatic, where two or more Ra and/or Rb groups (whether on the same or different carbon atoms) may be taken together with intervening atoms to form one or more optionally substituted, optionally unsaturated rings, optionally containing one or more heteroatoms, and where two Ra and Rb groups on the same carbon atom or on adjacent carbon atoms may optionally be taken together to form an alkene or, if on the same carbon atom, an oxo group;
q is an integer from 1 to 10;
Rd is optionally present, and if present are, independently at each occurrence selected from the group consisting of: halogen, —OR, —NR2, —SR, —CN, —NO2, —SO2R, —SOR, —SO2NR2, —CNO, —NRSO2R, —NCO, —N3, —SiR3; or an optionally substituted group selected from the group consisting of C1-20 aliphatic; C1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 6-10-membered aryl; 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and 4-7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; and
R is independently hydrogen, an optionally substituted C1-20 aliphatic group, or an optionally substituted aryl group.

### Claim 6 (depends on 1)

The method of claim 1, wherein Q is an optionally substituted bivalent moiety selected from the group consisting of:
where Rd is independently at each occurrence selected from the group consisting of: halogen, —OR, —NR2, —SR, —CN, —NO2, —SO2R, —SOR, —SO2NR2, —CNO, —NRSO2R, —NCO, —N3, —SiR3; or
an optionally substituted group selected from the group consisting of C1-20 aliphatic; C1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 6-10-membered aryl; 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and 4-7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; and
R is independently hydrogen, an optionally substituted C1-20 aliphatic group, or an optionally substituted aryl group.

### Claim 7 (depends on 1)

The method of claim 1, wherein Q is:

### Claim 8 (depends on 1)

The method of claim 1, wherein Q is:

### Claim 9 (depends on 1)

The method of claim 1, wherein:
R3′ is selected from the group consisting of an optionally substituted C1-40 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, and an optionally substituted aryl group; and
R1′, R2′, and R4′ are at each occurrence, independently selected from the group consisting of —H, fluorine, an optionally substituted C1-40 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, and an optionally substituted aryl group, where any two or more of R1′, R2′, R3′ and R4′ may optionally be taken together with intervening atoms to form one or more optionally substituted rings optionally containing one or more heteroatoms.

### Claim 10 (depends on 1)

The method of claim 1, wherein the moiety
is at each occurrence in the aliphatic polycarbonate chains is:

### Claim 11 (depends on 1)

The method of claim 1, wherein the moiety
is at each occurrence in the aliphatic polycarbonate chains is:

### Claim 12 (depends on 1)

The method of claim 1, further comprising in step (i) the use of one or more catalysts.

### Claim 13 (depends on 1)

The method of claim 1, further comprising in step (ii) the use of one or more catalysts.

### Claim 14 (depends on 13)

The method of claim 13, wherein at least one catalyst is selected from the group consisting of: (salcy)MX (salcy=N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2 diaminocyclohexane; M=Al, Co, Cr, Mn; X=halide or carboxylate), zinc glutarate, TPPM-X (TPP=tetraphenylphorphyrin; M=Al, Co, Cr; X=halide or alkoxide), and (beta-diiminate)zinc acetate.

### Claim 15 (depends on 13)

The method of claim 13, wherein at least one catalyst is cobalt(III) salcy (salcy=N,N′-bis(3,5-di-tert-butylsalicylidene).

### Claim 16 (depends on 1)

A composition made by the method of claim 1, wherein the composition comprises a polymer having formula P1,

### Claim 17 (depends on 16)

The composition of claim 16, wherein comprises one or more atoms selected from the group consisting of carbon, nitrogen, phosphorus, sulfur, and boron.

### Claim 18 (depends on 16)

The composition of claim 16, wherein comprises one or more carbon atoms.

### Claim 19 (depends on 16)

The composition of claim 16, wherein is:

### Claim 20 (depends on 16)

The composition of claim 16, wherein is derived from a polyfunctional chain transfer agent.

### Claim 21 (depends on 16)

The composition of claim 16, wherein the moiety
is at each occurrence in the aliphatic polycarbonate chains independently selected from the group consisting of:
wherein each Rx is independently selected from the group consisting of: optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl and optionally substituted heteroaryl.

### Claim 22 (depends on 16)

The composition of claim 16, wherein the moiety
at each occurrence in the aliphatic polycarbonate chains is independently selected from the group consisting of:
wherein each Rx is independently selected from the group consisting of: optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl and optionally substituted heteroaryl.

### Claim 23 (depends on 16)

The composition of claim 16, wherein the moiety
at each occurrence in the aliphatic polycarbonate chains is

### Claim 24 (depends on 16)

The composition of claim 16, wherein Q is an optionally substituted bivalent moiety selected from the group consisting of:
where Ra and Rb are each independently selected from the group consisting of: —H, halogen, optionally substituted C1-8 aliphatic, and optionally substituted C1-8 heteroaliphatic, where two or more Ra and/or Rb groups (whether on the same or different carbon atoms) may be taken together with intervening atoms to form one or more optionally substituted, optionally unsaturated rings, optionally containing one or more heteroatoms, and where two Ra and Rb groups on the same carbon atom or on adjacent carbon atoms may optionally be taken together to form an alkene or, if on the same carbon atom, an oxo group;
q is an integer from 1 to 10; and
Rd is optionally present, and if present are, independently at each occurrence selected from the group consisting of: halogen, —OR, —NR2, —SR, —CN, —NO2, —SO2R, —SOR, —SO2NR2, —CNO, —NRSO2R, —NCO, —N3, —SiR3; or an optionally substituted group selected from the group consisting of C1-20 aliphatic; C1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 6-10-membered aryl; 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and 4-7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; and
R is independently hydrogen, an optionally substituted C1-20 aliphatic group, or an optionally substituted aryl group.

### Claim 25 (depends on 16)

The composition of claim 16, wherein Q is an optionally substituted bivalent moiety selected from the group consisting of:
where Rd is independently at each occurrence selected from the group consisting of: halogen, —OR, —NR2, —SR, —CN, —NO2, —SO2R, —SOR, —SO2NR2, —CNO, —NRSO2R, —NCO, —N3, —SiR3; or an optionally substituted group selected from the group consisting of C1-20 aliphatic; C1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 6-10-membered aryl; 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and 4-7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; and
R is independently hydrogen, an optionally substituted C1-20 aliphatic group, or an optionally substituted aryl group.

### Claim 26 (depends on 16)

The composition of claim 16, wherein Q is:

### Claim 27 (depends on 16)

The composition of claim 16, wherein Q is:

### Claim 28 (depends on 16)

The composition of claim 16, wherein:
R3′ is selected from the group consisting of an optionally substituted C1-40 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, and an optionally substituted aryl group; and
R1′, R2′, and R4′ are at each occurrence, independently selected from the group consisting of —H, fluorine, an optionally substituted C1-40 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, and an optionally substituted aryl group, where any two or more of R1′, R2′, R3′ and R4′ may optionally be taken together with intervening atoms to form one or more optionally substituted rings optionally containing one or more heteroatoms.

### Claim 29 (depends on 16)

The composition of claim 16, wherein the moiety
at each occurrence in the aliphatic polycarbonate chains is:

### Claim 30 (depends on 16)

The composition of claim 16, wherein the moiety
at each occurrence in the aliphatic polycarbonate chains is:

### Claim 31 (depends on 16)

The composition of claim 16, comprising an aliphatic polycarbonate polyol selected from the group consisting of Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, and mixtures of any two or more of these:
wherein each n is, on average in the composition, within a range from about 2 to about 200, and t is from 0 to 10.

### Claim 32 (depends on 31)

The composition of claim 31, wherein the composition comprises:
Poly(propylene carbonate) of any of formulae Q1 through Q8 having an average molecular weight number of between about 500 g/mol and about 3,000 g/mol (e.g. each n is between about 3 and about 15), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups;
Poly(propylene carbonate) of any of formulae Q1 through Q8 having an average molecular weight number of about 500 g/mol (e.g. n is on average between about 3.5 and about 4.5), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups;
Poly(propylene carbonate) of any of formulae Q1 through Q8 having an average molecular weight number of about 1,000 g/mol (e.g. n is on average between about 3.5 and about 4.5), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups;
Poly(propylene carbonate) of any of formulae Q1 through Q8 having an average molecular weight number of about 2,000 g/mol (e.g. n is on average between about 8 and about 9.5), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups; or
Poly(propylene carbonate) of any of formulae Q1 through Q8 having an average molecular weight number of about 3,000 g/mol (e.g. n is on average between about 13 and about 15), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups.

### Claim 33 (depends on 16)

The composition of claim 16, comprising an aliphatic polycarbonate polyol selected from the group consisting of Q9, Q10, Q11, Q12, Q13, Q14, and mixtures of any two or more of these:
wherein each n is, on average in the composition, within a range from about 2 to about 200, and t is from 0 to 10.

### Claim 34 (depends on 33)

The composition of claim 33, wherein the composition comprises:
Poly(ethylene carbonate) of any of formulae Q9 through Q14 having an average molecular weight number of between about 500 g/mol and about 3,000 g/mol (e.g. each n is between about 4 and about 16), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups;
Poly(ethylene carbonate) of any of formulae Q9 through Q14 having an average molecular weight number of about 500 g/mol (e.g. n is on average between about 4 and about 5), a polydisperisty index less than about 1.25, at least 85% carbonate linkages, and at least 98% —OH end groups;
Poly(ethylene carbonate) of any of formulae Q9 through Q14 having an average molecular weight number of about 1,000 g/mol (e.g. n is on average between about 4 and about 5), a polydisperisty index less than about 1.25, at least 85% carbonate linkages, and at least 98% —OH end groups;
Poly(ethylene carbonate) of any of formulae Q9 through Q14 having an average molecular weight number of about 2,000 g/mol (e.g. n is on average between about 10 and about 11), a polydisperisty index less than about 1.25, at least 85% carbonate linkages, and at least 98% —OH end groups; or
Poly(ethylene carbonate) of any of formulae Q9 through Q14 having an average molecular weight number of about 3,000 g/mol (e.g. n is on average between about 15 and about 17), a polydisperisty index less than about 1.25, at least 85% carbonate linkages, and at least 98% —OH end groups.

### Claim 35 (depends on 16)

The composition of claim 16, comprising an aliphatic polycarbonate polyol represented by the formula:

### Claim 36

An aliphatic epoxide-CO2 based polycarbonate polyol composition comprising polymer chains of formula P1:
wherein:
is a multivalent moiety;
R1, R2, R3, and R4 are at each occurrence, independently selected from the group consisting of —H, fluorine, an optionally substituted C1-40 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, and an optionally substituted aryl group, where any two or more of R1, R2, R3, and R4 may optionally be taken together with intervening atoms to form one or more optionally substituted rings optionally containing one or more heteroatoms;
R1′, R2′, R3′, and R4′ are at each occurrence, independently selected from the group consisting of —H, fluorine, an optionally substituted C1-40 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, and an optionally substituted aryl group, where any two or more of R1′, R2′, R3′ and R4′ may optionally be taken together with intervening atoms to form one or more optionally substituted rings optionally containing one or more heteroatoms;
each n is independently, on average in the composition, within a range from about 2 to about 200;
Q is an optionally substituted bivalent moiety; and
x and y are each independently an integer from 0 to 6, where the sum of x and y is between 2 and 6.

### Claim 37 (depends on 36)

The composition of claim 36, wherein comprises one or more atoms selected from the group consisting of carbon, nitrogen, phosphorus, sulfur, and boron.

### Claim 38 (depends on 36)

The composition of claim 36, wherein comprises one or more carbon atoms.

### Claim 39 (depends on 36)

The composition of claim 36, wherein is:

### Claim 40 (depends on 36)

The composition of claim 36, wherein is derived from a polyfunctional chain transfer agent.

### Claim 41 (depends on 36)

The composition of claim 36, wherein the moiety
is at each occurrence in the aliphatic polycarbonate chains independently selected from the group consisting of:
wherein each Rx is independently selected from the group consisting of: optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl and optionally substituted heteroaryl.

### Claim 42 (depends on 36)

The composition of claim 36, wherein the moiety
at each occurrence in the aliphatic polycarbonate chains is independently selected from the group consisting of:
wherein each Rx is independently selected from the group consisting of: optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl and optionally substituted heteroaryl.

### Claim 43 (depends on 36)

The composition of claim 36, wherein the moiety
at each occurrence in the aliphatic polycarbonate chains is

### Claim 44 (depends on 36)

The composition of claim 36, wherein Q is an optionally substituted bivalent moiety selected from the group consisting of:
where Ra and Rb are each independently selected from the group consisting of: —H, halogen, optionally substituted C1-8 aliphatic, and optionally substituted C1-8 heteroaliphatic, where two or more Ra and/or Rb groups (whether on the same or different carbon atoms) may be taken together with intervening atoms to form one or more optionally substituted, optionally unsaturated rings, optionally containing one or more heteroatoms, and where two Ra and Rb groups on the same carbon atom or on adjacent carbon atoms may optionally be taken together to form an alkene or, if on the same carbon atom, an oxo group;
q is an integer from 1 to 10; and
Rd is optionally present, and if present are, independently at each occurrence selected from the group consisting of: halogen, —OR, —NR2, —SR, —CN, —NO2, —SO2R, —SOR, —SO2NR2, —CNO, —NRSO2R, —NCO, —N3, —SiR3; or an optionally substituted group selected from the group consisting of C1-20 aliphatic; C1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 6-10-membered aryl; 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and 4-7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; and
R is independently hydrogen, an optionally substituted C1-20 aliphatic group, or an optionally substituted aryl group.

### Claim 45 (depends on 36)

The composition of claim 36, wherein Q is an optionally substituted bivalent moiety selected from the group consisting of:
where Rd is independently at each occurrence selected from the group consisting of: halogen, —OR, —NR2, —SR, —CN, —NO2, —SO2R, —SOR, —SO2NR2, —CNO, —NRSO2R, —NCO, —N3, —SiR3; or an optionally substituted group selected from the group consisting of C1-20 aliphatic; C1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 6-10-membered aryl; 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and 4-7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; and
R is independently hydrogen, an optionally substituted C1-20 aliphatic group, or an optionally substituted aryl group.

### Claim 46 (depends on 36)

The composition of claim 36, wherein Q is:

### Claim 47 (depends on 36)

The composition of claim 36, wherein Q is:

### Claim 48 (depends on 36)

The composition of claim 36, wherein:
R3′ is selected from the group consisting of an optionally substituted C1-40 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, and an optionally substituted aryl group; and
R1′, R2′, and R4′ are at each occurrence, independently selected from the group consisting of —H, fluorine, an optionally substituted C1-40 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, and an optionally substituted aryl group, where any two or more of R1′, R2′, R3′ and R4′ may optionally be taken together with intervening atoms to form one or more optionally substituted rings optionally containing one or more heteroatoms.

### Claim 49 (depends on 36)

The composition of claim 36, wherein the moiety
at each occurrence in the aliphatic polycarbonate chains is:

### Claim 50 (depends on 36)

The composition of claim 36, wherein the moiety
at each occurrence in the aliphatic polycarbonate chains is:

### Claim 51 (depends on 36)

The composition of claim 36, comprising an aliphatic polycarbonate polyol selected from the group consisting of Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, and mixtures of any two or more of these:
wherein each n is, on average in the composition, within a range from about 2 to about 200, and t is from 0 to 10.

### Claim 52 (depends on 51)

The composition of claim 51, wherein the composition comprises:
Poly(propylene carbonate) of any of formulae Q1 through Q8 having an average molecular weight number of between about 500 g/mol and about 3,000 g/mol (e.g. each n is between about 3 and about 15), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups;
Poly(propylene carbonate) of any of formulae Q1 through Q8 having an average molecular weight number of about 500 g/mol (e.g. n is on average between about 3.5 and about 4.5), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups;
Poly(propylene carbonate) of any of formulae Q1 through Q8 having an average molecular weight number of about 1,000 g/mol (e.g. n is on average between about 3.5 and about 4.5), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups;
Poly(propylene carbonate) of any of formulae Q1 through Q8 having an average molecular weight number of about 2,000 g/mol (e.g. n is on average between about 8 and about 9.5), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups; or
Poly(propylene carbonate) of any of formulae Q1 through Q8 having an average molecular weight number of about 3,000 g/mol (e.g. n is on average between about 13 and about 15), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups.

### Claim 53 (depends on 36)

The composition of claim 36, comprising an aliphatic polycarbonate polyol selected from the group consisting of Q9, Q10, Q11, Q12, Q13, Q14, and mixtures of any two or more of these:
wherein each n is, on average in the composition, within a range from about 2 to about 200, and t is from 0 to 10.

### Claim 54 (depends on 53)

The composition of claim 53, wherein the composition comprises:
Poly(ethylene carbonate) of any of formulae Q9 through Q14 having an average molecular weight number of between about 500 g/mol and about 3,000 g/mol (e.g. each n is between about 4 and about 16), a polydisperisty index less than about 1.25, at least 95% carbonate linkages, and at least 98% —OH end groups;
Poly(ethylene carbonate) of any of formulae Q9 through Q14 having an average molecular weight number of about 500 g/mol (e.g. n is on average between about 4 and about 5), a polydisperisty index less than about 1.25, at least 85% carbonate linkages, and at least 98% —OH end groups;
Poly(ethylene carbonate) of any of formulae Q9 through Q14 having an average molecular weight number of about 1,000 g/mol (e.g. n is on average between about 4 and about 5), a polydisperisty index less than about 1.25, at least 85% carbonate linkages, and at least 98% —OH end groups;
Poly(ethylene carbonate) of any of formulae Q9 through Q14 having an average molecular weight number of about 2,000 g/mol (e.g. n is on average between about 10 and about 11), a polydisperisty index less than about 1.25, at least 85% carbonate linkages, and at least 98% —OH end groups; or
Poly(ethylene carbonate) of any of formulae Q9 through Q14 having an average molecular weight number of about 3,000 g/mol (e.g. n is on average between about 15 and about 17), a polydisperisty index less than about 1.25, at least 85% carbonate linkages, and at least 98% —OH end groups.

### Claim 55 (depends on 36)

The composition of claim 36, comprising an aliphatic polycarbonate polyol represented by the formula: