Novel Gelling Catalyst for Non-Emission Flexible Polyurethane
Foam
TAKAO SUZUKITOSOH CORPORATION
4560 Kaisei-cho, Shunan-city, Yamaguchi
746-8501, JapanYOSHIHIRO TAKAHASHITOSOH CORPORATION
4560 Kaisei-cho, Shunan-city, Yamaguchi
746-8501, Japan

HIROYUKI KISOTOSOH CORPORATION
4560 Kaisei-cho, Shunan-city, Yamaguchi
746-8501, Japan

JEFF TUCKERTOSOH Specialty Chemicals USA, Inc.
4080 McGinnis Ferry Road, Suite 1303
Alpharetta, GA 30005, USA

ABSTRACT
Flexible and semi-rigid polyurethane foams have been widely used in automotive interior parts, residential upholstered
furniture and bedding. In these, as well as other end use industries, a reduction of Volatile Organic Compounds (VOCs)
emissions from polyurethane foams continues to be an important issue [1, 2].
To address this challenge, reactive amine catalysts, which have an active hydrogen group, have been developed, evaluated,
and used for the purpose of reducing VOC emissions. Unfortunately, many of these reactive catalysts tend to lose theircatalytic activity during the latter stages of the foaming process resulting in decreased performance during the curing function.
TOSOH Corporation has continued to research the next-generation of non-fugitive catalysts for polyurethane systems, andrecently developed a novel gelling catalyst that provides improved performance in overall catalytic activity. This catalyst has
a similar function as TEDA and exhibits better durability performance compare to other non-fugitive catalysts.
TOSOH Corporation will review this work and propose solutions for reduced VOC systems with low or non-emission
catalyst.
INTRODUCTION
Polyurethane foam is made from polyols, isocyanates and additives such as catalysts, silicone surfactants, flame retardants,
anti-oxidants, chain-extenders, crosslinkers, release agents, etc. In general, the automotive and furniture industries are
sensitive to VOCs due to customer specifications and regulations.
Tertiary amine catalysts such as TEDA have been used for many years in the production of polyurethane foam. Their usage,
however, is targeted for reduction due to emissions from the finished foam and associated unpleasant odor. In order toovercome the emission problems, a wide variety of non-fugitive amines containing hydroxyl, amino and urea groups havebeen proposed and evaluated[3-9], because such catalysts can react with isocyanate group during the foaming process andbecome part of polymer network. However, a fully adequate replacement catalyst system has not been found yet. The catalytic
activity of these non-fugitive catalysts is lower than conventional catalysts and the foam properties, curing function anddurability performance, tend to worsen due to the lack of gelling activity. For this reason, amine catalysts that have highgelling activity such as TEDA and exhibit low-emissions are a consistent demand from the market.
Previously, Tosoh has reported the gelling properties and potential of reactive TEDA (RTEDA) by using computational
chemistry [10]. To establish this result, RTEDA was synthesized and evaluated by comparison of various kinds of reactive
amines. In this paper, the characteristics of RTEDA are discussed. In addition, novel amine catalysts systems are proposed for
Flexible and semi-rigid polyurethane foams.

EXPIRIMENTAL

Catalysts
The lists of amine catalysts evaluated in this paper and their abbreviation are shown in Table 1. TEDA (L33) and
TOYOCAT-ET are standard tertiary amine catalysts for flexible and semi-rigid polyurethane foams. L33 is a liquid type ofTEDA and shows strong gelling catalytic activity. RTEDA, which has a hydroxylmethyl substituent in TEDA structure, isdiluted by 33.3% with DPG like L33 to compare the reactivity. TOYOCAT-RX24 and catalysts A-E are conventional reactive
amine catalysts used in PUR production.
Table 1. Amine Catalysts
Abbreviation

Chemical Structure

Abbreviation

TEDA

N
N

Catalyst-A

N

33.3%
in DPG 66.7%

Catalyst-B

N

N

Catalyst-C

N

N

N
N

TEDA-L33

N
N

RTEDA

TOYOCAT-ETTOYOCAT-RX24

N

O

OH

N

70%
in DPG 30%

Special Reactive Amine

Chemical Structure
OH

OH

N

Catalyst-D

Catalyst-E

N

O

N

N

OH
OH

OH

Formulation and Foam Preparation
Flexible slabstock and molded foam formulations were evaluated in this study, shown in Table 2 and 3. Forming conditions
are given in Table 4.
The slabstock foams were prepared using an aluminum open mold (25x25x25 cm) at 23°C by hand mixing methods. The
concentration of stannous dioctoate (SDO) was varied from 0.10 to 0.25 in order to investigate process latitude of the amine
catalysts. The concentration of amine catalyst was adjusted to give similar rise times (100 seconds) in order to evaluate eachcatalyst system on the same criteria.
Molded foams were prepared using an aluminum mold (25 x 25 x 8 cm) which was preheated in an oven prior to molding(from 60 ± 1oC). Over-all foam density was adjusted to 52 kg/m3. All chemical components were conditioned at a temperatureof 20 ± 1oC. The concentration of each catalyst was adjusted to give an identical gelling time of 60 seconds. The demold time
was fixed at 8 minutes.
Table 2. Formulations for Flexible slabstock foam
OHv(mgKOH/g)
Tri-functional Polyether Polyol
57.5
Water
Silicon Surfactant
SDO
Amine Catalysts
NCO content(wt%)
Isocyanate(TDI、T-80)
48.2

pbw
92.6
5
1
variedvariedIndex
110

Table 3. Formulations for HR molded foam
OHv(mgKOH/g)
Tri-functional Polyether Polyol
33.6
Cell Openner
34.6
Water
Diethanolamine
Silicon Surfactant
Amine Catalysts
NCO content(wt%)
Isocyanate(MDI)
31.7

Table 4. Forming Conditions
Liquid Temp.
Mixing speed
Mold Temp.
Mold

Slabstock
20oC
3,000rpm（10sec.)
23oC
25 x 25 x 25cm

HR molded
20oC
6,000rpm (5sec)
60oC
25 x 25 x 8cm

pbw
92.6
1.9
3.2
0.65
1
variedIndex
100

Measurement of Rise Profiles
The evaluation of rise profile during foaming has been considered an important parameter for the development ofpolyurethane systems as well as quality control for the production. The rise profiles were measured by using the long-range
laser displacement apparatus (LF-2510, KEYENCE Corp.). The profile data was collected every second.
Measurement of Foam Physical Properties
After 7days at ambient conditions (23±0.3°C and 50±2%RH), physical foam properties such as foam density, CLD(compression load deflection), air flow, tensile strength, elongation and tear strength were measured according to thefollowing test method (CLD: ISO 2439, Tensile strength and Elongation: ISO 1798, Tear strength: ISO 8067).
Durability Tests
Different static compression set and load loss tests were performed for durability testing. Dry compression sets wereconducted with A method (70°C, 22hrs, 50% compression), B method (70°C, 72hrs, 50% compression) and C method (after
90°C /100% RH x 200hr aging, 70°C, 22hrs, 50% compression).
Wet compression set was conditioned at 50°C, 95% RH, 22hrs, at 50% compression.
Amine Emission Tests
Two different methods were used to trace the remaining free amine in the foam and determine the emission value of theindividual catalyst compounds.
FOAM EXTRACTION
The total amount of free amine catalysts in the foam was measured via the solvent extraction method. 2.0grams of foam wereplaced into a 30 milliliter vial with 14.0 grams of methanol. The vial was sealed and placed into shaker with heated water at
50°C for 72 hours and allowed to cool. The methanol was compressed out of the foam completely, and then the extracts wereidentified by gas chromatographic determination.
EMISSION TESTING
Volatile emission from the foam was determined through a dynamic headspace test utilizing thermal desorption method(VDA278 method). VDA 278 is used as a standard emission test in the automotive industry to evaluate emissions frompolyurethane foam under aggressive conditions [9]. Small section of material placed inside of a headspace vial. The vial was
analyzed by the VOC GC–MS headspace method which was heated at 90oC for 30 minutes. The vial was then re-analyzed by
the FOGGING headspace method which was heated at 120oC for 60minutes.
PVC Staining Measurements
Accelerated aging tests were carried out in closed containers in the presence of a PVC film according to VW PVC3937. A
foam sample of 70 × 70 × 30 mm, cut from the top part of the foam, was placed at the bottom of a 2 liter glass separable flask.
A piece of gray PVC soft sheet (VW sun visor sheet) was hung by the lid of the flask, which was then sealed. Aging was
carried out at 100°C for 72 hours. After cooling, the PVC sheet discoloration was measured using a colorimeter. Smallerchanges in color result in a lower ∆E measurement.
RESULTS AND DISCUSSION
To investigate characteristics of various reactive amine catalysts (RACs) including non-fugitive amine catalyst,
hand-mixing was carried out. As a reference, TEDA-L33 and/or TEDA-L33/TOYOCAT-ET combination (=4/1(wt/wt)) wereused. Catalyst-A (Cat.A) was used as blowing catalysts to improve closed cell foam. The formulations and properties of thefoams are summarized in Table 6 and 7.

1. Slabstock Foam
1-1. Reactivity
In general, an amine catalyst is combined with a tin compound for flexible polyether slabstock foams. The amine catalyst
used in producing flexible slabstock foams plays a very important role, from a technical and economical standpoint, because it
accelerates both urethane and urea reactions and directly affects the foam physical properties. L33 is widely used as a standard
amine catalyst for flexible polyether slabstock foams.
As shown in Figure 1, RTEDA exhibited an almost identical foam height to TEDA (L33), although RTEDA provided afaster initial reaction. In addition, the RTEDA-foams were observed health-bubble, which is an indication open/closed cell,and no-settling in all SDO ranges. In contrast, TEDA-foams were confirmed settling phenomena at low SDO amount. Thissuggests that RTEDA exhibits a wide process range of foam reaction owing to low catalytic activity and blowing ability
compared with TEDA and supports our past computational study.
Regarding catalytic activity, RTEDA required about twice the dosage as TEDA. The introduction of hydroxymethyl group
into the TEDA skeleton is thought to reduce the catalytic activity of adjacent nitrogen site by steric hindrance.
2.0

30

RTEDA(33.3% in DPG)
Cat. Dosage (pbw)

Rise Height (cm)25
20
RTEDA/SDO(0.15)

15

RTEDA/SDO(0.20)

10TEDA/SDO(0.15)
5TEDA(L33)

1.5

1.0

0.5

TEDA/SDO(0.20)

0

0.0
0

60

120

180

Time (min.)

0.05

0.10

0.15
0.20
SDO (pbw)

Figure1. Rise profiles

Figure2. Catalytic Activity

0.25

1-2. Foam Formability
Table 5 shows the result of foam formability compared with L33 under several different SDO dosages. RTEDA provided
excellent formability regardless of SDO. In case of TEDA, cracks in the foam were observed at low amount of SDO usage.
Table5. Foam Formabilities under several different SDO dosages
SDO=0.10pbw
SDO=0.15pbw

RTEDA

crack
TEDA

SDO=0.20pbw

SDO=0.25pbw

0.30

1-3. Foam Physical Properties
Table 6 shows the reaction profiles and foam properties of RTEDA and TEDA. RTEDA exhibited better physical properties
at reduced SDO level; particularly air flow, tensile strength and elongation properties.
As for durability performance, RTEDA showed slightly inferior performance compared with TEDA (L33), owing toreactive amine. However, we feel the values will be permissive.
Table6. Reaction profiles and physical properties by Hand mixing (H 2 O=5pbw)
RTEDA(33.3%,DPG)

Catalyst

L33(33.3%,DPG)

(pbw)

1.30

0.96

0.77

0.58

0.54

0.45

0.36

0.27

(pbw)

0.10

0.15

0.20

0.25

0.10

0.15

0.20

0.25

Mold Free Foam (Al mold:25*25*25(cm ))CT(sec.)
20

20

20

20

26

25

24

22

RT

SnOct(SDO)

3

Core Density(sec.)

104

102

93

89

105

100

97

95

3

22.3

21.6

21.8

21.6

23.2

21.8

21.7

21.0

2

3.1

3.2

3.7

4.3

3.3

3.4

3.6

3.8

2

3.7

3.7

4.5

5.0

4.1

3.9

4.2

4.4

2

6.4

7.0

8.4

9.2

7.2

6.6

7.2

7.4

273

247

156

102

135

203

186

178

171

178

61

37

47

98

83

95

(kg/m )
(kN/m )

CLD 25%compression(kN/m )

40%compression(kN/m )
65%compression
3
Air Flow (Upper)(cm /(cm 2 /s))
(Lower)3

2(cm /(cm /s))
2

(kN/m )

100

90

87

97

86

91

92

95

Elongation

(%)

139

127

112

113

101

115

112

118

Tear strength(kN/m)

0.59

0.57

0.55

0.52

0.41

0.46

0.48

0.55

50% Dry-CS (A)

(%)

5.8

3.8

4.2

3.8

4.9

3.2

2.9

2.5

Tensile strength

2. HR Molded Foam
2-1. Foam Physical Properties
Foam Hardness
Considering core density and foam hardness in each catalyst, it can be said L33/ET (=4/1) and RTEDA/Cat.A provided thehardest foam in all evaluated catalysts (Shown in Figure 3). RTEDA showed high synergy effect with blowing catalysts like
Cat.A as well as TEDA.
Tear Strength
Tear strength basically exhibited the same tendency as foam hardness. The results are shown in Figure 4. RTEDA/Cat-A
and LE41 exhibited the highest tear strength in all evaluated catalysts.
Tensile Strength and Elongation
The relationship between tensile strength and elongation was investigated. The results are shown in Figure 5. RTEDA
showed relatively high values among all catalysts. This result indicates that RTEDA may have crosslinking abilities comparedwith TEDA.

48

6

46

Cat.D

Cat.C

Cat.B

Cat.E

42
RX24

TEDA

L33/ET(4/1)

5

RTEDA/Cat.A(4/1)

44

Density (kg/m3)

50
CLD(40%compression)
Core Density

RTEDA

CLD (kN/m2)

7

Figure3. Effect of Various Amine Catalysts on CLD Value

2

Figure4. Effect of Various Amine Catalysts on Tear strength

Cat.E

60
Cat.D

100

Cat.C

70

Cat.B

110

RX24

Cat.C

Cat.B

80

RTEDA/Cat.A

42

90

120

L33/ET(4/1)

0.3

Elongation

130

Cat.E

44

Cat.D

0.4

RX24

46

RTEDA/Cat.A

0.5

3

48

Density (kg/m )Core Density

0.6

100
TB

Elongation at break (%)

140
Tensile strength (kN/m )50
TR

L33/ET(4/1)

Tear strength (kN/m)

0.7

Figure5. Effect of Various Amine Catalysts on Tensile
strength and Elongation

2-2. Foam Durability Performance
Dry Compression Set (DCS) A and B methods
The influence of various RACs on DCS was investigated. The results are shown in Figure 6. As for DCS-A, L33/ET
exhibited the best result in all evaluated catalysts. Among RACs, RTEDA/Cat.A exhibited the best values.
As for DCS-B, there is significant difference between L33/ET and RACs. All DCS-B of RACs became worse resultscompared with L33/ET. However, RTEDA/Cat.A exhibited permissible values.
Dry-CS (A)Dry-CS (B)15

10Figure 6. Effect of Various Amine
Catalysts on DCS

Cat.E

Cat.D

Cat.C

Cat.B

RX24

0

RTEDA/Cat.A

5

L33/ET(4/1)

Compression set ( % )20Wet Compression Set (WCS)The influence of various RACs on WCS was investigated. The result is shown in Figure 7. However, Wet Compression Set(WCS) testing did not show a significant difference among RACs except for Cat.D. There is a proportional relationshipbetween catalyst dosage (mol equivalent) and Humid aging test such as WCS and HACS. The more catalyst loaded, the worse
durability performances become. (Shown in Figure 8)
Compression set (Wet)
35
30

15

25
CS (%)

10

5

20
15

RTEDA/Cat.A

Cat.E

Cat.D

Cat.C

5
Cat.B

RX24

0

RTEDA/Cat.A

10
L33/ET(4/1)

Compression set ( % )

20

0
0

10

20

30

40

50

Dosage (mmol)

Figure7. Effect of Various Amine Catalysts on WCS

Figure8. The relationship between Catalyst dosage and WCS

Humid Aged Compression Set (HACS)
It is well known that HACS is most severe test for RACs to pass specification. This is because PUR polymer structure
derived from RACs and NCO reaction is less stable when compared to those derived from standard non-reactive tertiaryamine catalysts. To pass this specification by using RACs, modification of formulation itself also becomes an importantfactor.
The results of HACS are shown in Figure 9.
L33/ET exhibited the best results in all evaluated catalysts. Among RACs, RTEDA/Cat.A and Cat B exhibited permissible
values.

15

10

Cat.E

Cat.D

Cat.C

Cat.B

RX24

0

RTEDA/Cat.A

5

L33/ET(4/1)

Compression set ( % )20

Figure9. Effect of Various Amine Catalysts on HACS
2-3. Amine Emissions
Figure 10 shows the extraction results as an eluted rate for the theoretical amount of catalyst in the foam. Test samples weretaken at the surface part of foams (incl. skin layer). The conventional catalysts, TEDA and ETS, show extremely high values.

This result, which exceeds the theoretical value, is thought to be due to the shift of the amine catalyst from core to surface ofthe foam. Among RACs, significant differences were not been observed.
Figure 11 shows amine emission results by VDA278. Test pieces were also used the surface part of foams. As for L33/ET,
it indicates that high levels of residual free amine remains in the foam and under VOC method condition (90oC for 30minutes).
Meanwhile, RX24, Cat.B, D and E were not detected under VOC method, but under FOG method condition (120oC for
60minutes after VOC method). Secondary hydroxyl group like Cat.B forms strong linkage with isocyanate [12], but has low
reactivity compared to primary hydroxyl group. So unreacted catalysts remain in the foam, Cat.B shows higher emission than
Cat.D or E under fogging method.
However, RTEDA/Cat.A was not detected under both conditions, RTEDA showed better performance.
300

L33/ET(4/1)
L41=0.62pbw RTEDA/Cat-A(4/1)=1.69pbw

40
20

1.05pbw

1.25pbw

1.65pbw

0

250
200

231ppm60

VOC
477ppm80

Amine Emission (ppm)

150

Fog

240ppm

100

61ppm

50

0ppm

32ppm

20ppm

t. E
Ca

t. D
Ca

t. B
Ca

24
RX

t. A
Ca

RT

ED

D
TE

Figure 10. Eluted catalysts by methanol extraction

A

S

A

Ca
t. D

Ca
t. C

Ca
t. B

t- A
Ca

A
RT

ED

S
ET

TE

DA

0
ET

Extraction Rate (%)

100

Figure 11. Amine Emissions by VDA278 method

2-4. PVC staining
The influence of various amine catalysts on PVC staining test was investigated as shown in Figure 12.
When a gray color of PVC sheet was used, there does not appear to be a significant difference among RACs. But in case ofa white color of PVC sheet, PVC staining was observed in all of test samples. Among them, a combination of RTEDA and
Cat.A exhibited relatively lower values.
These results (incl. Amine emissions) suggest RTEDA reacts with isocyanates and forms a strong linkage. Since unreacted
RTEDA decreases without limit, amount of migration to PVC can be reduced. Regarding Cat.D, it volatilized out of foam
immediately while or after foaming because of low molecular weight.

White sheet
Gray sheet

50
40
30
20

Cat.D

Cat.C

Cat.B

RTEDA/Cat.A

0

L33/ET(4/1)

10
Original

Color change (delta E)

60

Figure 12. Effect of various amine catalysts on PVC staining

Table 7. Reaction profiles and physical properties by Hand mixing (All-MDI)
RTEDA/
Catalyst
LE41
RX24
CatB
CatA
(pbw)
0.62
1.45/0.24
1.46
1.05(mmol)
2.02
4.68
8.59
4.28
Cup Free foam (Hand mixing)CT(sec.)
10.2
12.2
13.3
13.8
GT
(sec.)
60
60
61
59
RT
(sec.)
85
80
82
75
3
Core Density
38.8
38.1
37.4
37.8
(kg/m )
3
Mold pack foam (Al mold:25*25*8(cm ))Overall Foam weight
(g)
257.8
259.3
259.4
258.7
3
Overall Density
51.6
51.9
51.9
51.7
(kg/m )ILD 25%compression (kN/m 2 )
7.0
6.6
6.3
6.1
65%compression (kN/m 2 )
20.8
19.5
18.4
17.3
3
Core Foam Density
45.8
45.1
44.4
44.8
(kg/m )
CLD 40%compression (kN/m 2 )
6.9
6.5
6.2
6.1
(%)
Hysteresis Loss (65%)
33.0
33.1
33.6
31.8
2
(kN/m )
126
136
126
120
Tensile strength(%)
Elongation
76
79
76
77
(kN/m)
Tear strength
0.50
0.54
0.47
0.46
(%)
50% Dry-CS (A)
6.0
6.5
6.6
7.2
(%)
50% Dry-CS (B)
7.1
8.7
9.7
10.4
(%)
Wet-CS
12.3
14.3
16.4
14.9
(%)
HACS
5.9
9.1
12.6
9.5

CatC

CatD

CatE

1.20
7.49

1.64
18.40

1.33
9.16

13.1
62
83
37.6

9.2
59
84
37.5

13.0
60
79
37.2

258.9
51.8
5.9
16.9
45.1
6.0
30.6
116
73
0.45
7.5
12.9
14.6
11.1

259.8
52.0
6.3
18.5
45.6
6.1
33.1
106
76
0.51
8.8
12.0
17.5
15.0

259.6
51.9
6.0
17.0
45.1
5.9
26.6
119
76
0.42
7.3
11.1
15.4
13.4

CONCLUSIONSTOSOH developed a novel gelling reactive catalyst we call RTEDA. Various kinds of amine catalysts were evaluated in
flexible slabstock and HR molded systems. As a result, RTEDA exhibited better durability performance as well as better
physical properties.
1. RTEDA, which has a hydroxylmethyl substituent in TEDA structure, can be used to reduce amine emissions.
2. In the slabstock test system, unlike TEDA, RTEDA provides improved physical properties at low SDO amount.
RTEDA exhibits wide process range owing to low catalytic activity and blowing ability compared with TEDA.
3. In the HR molded test system, RTEDA exhibits high synergy effect with blowing catalysts. Combination use improves
not only catalytic activity but also physical properties and durability performances.
We hope this catalyst and catalyst system will contribute to polyurethane industry.

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BIOGRAPHIES
Takao Suzuki
Takao Suzuki joined TOSOH Corporation in 1999 after receiving B.S. and M.S. degree in Organic
Chemistry from Tohoku University in 1997 and 1999 respectivly. After development work inorganic polymer chemistry, he has been engaged in development of amine catalysts and otherrelated materials for polyurethanes.

Yoshihiro Takahashi
Yoshihiro Takahashi joined TOSOH Corporation in 1979. After development work in rubber
chemical products, he has been engaged in development of amine catalysts and other relatedmaterials for polyurethanes.

Hiroyuki Kiso
Hiroyuki Kiso joined TOSOH Corporation in 1993 after receiving B.S. and M.S. degree in Organic
Chemistry from Hiroshima University in 1991 and 1993 respectively. After development work inorganic chemicals, he has been engaged in development of amine catalysts and other relatedmaterials for polyurethanes.

Jeff Tucker
Jeff Tucker joined Tosoh Specialty Chemicals USA in February 2009 and is the Technical SalesManager of TEDA & TOYOCAT polyurethane catalysts for the Americas. He holds a B.S. Degreein Chemistry from Berry College and a M.B.A from Kennesaw State University. Since joining thepolyurethane industry in 1998, he has worked in various capacities including Research andDevelopment, Operations Management, and Sales and Marketing.